Language：English   Publishing type：Research paper (scientific journal)  

The soon spoiled strawberries need to be classified from healthy fruits in an early stage. In this research, a machine vision system is proposed for inspecting the quality of strawberries using ultraviolet (UV) light based on the excitation-emission matrix (EEM) results. Among the 100 fruits which were harvested and stored under 10 °C condition for 7 days, 7 fruits were confirmed to be spoiled by using a firmness meter. The EEM results show the fluorescence compound contributes to a whitish surface on the spoiled fruits. Based on the EEM results, UV fluorescence images from the bottom view of strawberries were used to classify the spoiled fruits and healthy fruits within 1 day after harvest. These results demonstrate the UV fluorescence imaging can be a fast, non-destructive, and low-cost method for inspecting the soon spoiled fruits. The proposed index related to the spoiling time can be a new indicator for qualifying strawberry.

DOI： 10.1016/j.foodchem.2021.130776

Scopus

PubMed

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：IOP Publishing  

Japanese tomato cultivar ‘Rinka 409’ is suitable for harvesting at a fully ripe stage since it remains firm at the stage, resulting in longer shelf life. However, it is difficult to estimate the quality change because its color does not change after the fully ripe stage. For ‘Momotaro,’ we previously proposed a fluorescence-based indicator of overripening; however, its suitability for another cultivar, ‘Rinka 409’, and its relationship with temperature and quality were unclear. Therefore, in this study, we investigated the appropriateness of this fluorescence-based index for the above purposes. In 2021, 45 tomato seedlings planted in 2020 were harvested at the fully ripe stage and used for experiments. Weight loss and firmness were evaluated to determine the quality of the tomatoes. The post-harvest temperatures were set as 10, 17, and 25 °C. The results showed that the rate of weight loss increased linearly, whereas the firmness decreased exponentially. For non-destructive estimation of these properties, the excitation-emission matrix (EEM) was measured in the range of 250–460 nm and 280–750 nm for the excitation and emission, respectively. ‘Rinka 409’ showed a strong fluorescence emission at 400 nm/620 nm of the excitation/emission, respectively, regardless of days and temperature. The fluorescence intensity, as well as the firmness, decreased exponentially. Thus, a linear relationship was observed between them. The firmness of ‘Rinka 409’ can be estimated using a simpler linear regression model using this method than previous researches.

DOI： 10.1088/1755-1315/924/1/012020

researchmap

Other Link： https://iopscience.iop.org/article/10.1088/1755-1315/924/1/012020/pdf

Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER  

This research aimed at providing a quick, and non-destructive method for estimating freshness of intact Japanese dace (Tribolodon hakonensis) fish refrigerated below 5 degrees C using multispectral imaging technique coupled with multivariate analysis techniques. The fluorescence excitation-emission matrices (EEMs) for outside parts of the fish (eyeball, scales) were taken to establish the proper excitation wavelengths. Afterwards, four lighting devices; white, 395 nm, 365 nm and 280 nm LEDs were used to illuminate the sample for capturing images using both the UV camera and a common color camera. Biochemical analysis (electrophoresis measurement) was carried out to examine fish freshness and then expressed using a reference method as K values. Both EEM and imaging data were modelled with the measured K value using partial least square (PLS) regression. A novel algorithm based on multispectral imaging data was proposed as a potential fish freshness indicator during storage. From the results, R2 of 0.94 and RMSE of 2.42% were achieved. This research demonstrated that the fluorescence multispectral imaging technique is a powerful tool with great potential in non-destructive monitoring and examining fish freshness during storage.

DOI： 10.1016/j.lwt.2021.112207

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCI LTD  

To investigate the potential of fluorescence spectroscopy in evaluating soybean protein and oil content, excitation emission matrix (EEM) was measured on 34 samples of soybean flours using a front-face measurement, and the accuracy of the protein and oil content prediction was evaluated. The EEM showed four main peaks at excitation/emission (Ex/Em) wavelengths of 230/335, 285/335, 365/475, and 435/495 nm. Furthermore, second derivative synchronous fluorescence (SDSF) spectra were extracted from the EEMs, and partial least square regression and support vector machine models were developed on each of the EEMs and SDSF spectra. The R2 values reached 0.86 and 0.74 for protein and oil, respectively. From the loading spectra, fluorescence at Ex/Em of 230-285/335 nm and 350/500 nm mainly contribute to the protein and oil content prediction, respectively. Those results revealed the potential of fluorescence spectroscopy as a tool for a rapid prediction of soybean protein and oil content.

DOI： 10.1016/j.foodchem.2021.130403

Web of Science

Scopus

PubMed

researchmap

Publishing type：Research paper (international conference proceedings)  

After harvesting, the evaluation of tomato characteristics is essential to decide a correct postharvest handling process, maturity stages, and shelf-life prediction. Previous research shows that fluorescence imaging could be used to enhance the maturity level detection after the red stage. However, the correlation between external appearance and internal fluorescence change has not been studied well. In this research, tomato surface has been classified into two parts i.e. skin and flesh. The parts have been extracted, and the fluorescence characteristic has been monitored from red-stages to over-ripening. The fluorescence image changes are confirmed during the storages and correlated with the weight loss as a freshness index. The results show that the fluorescence characteristic of tomato skin and flesh is different. The highest fluorescence emission peak for excitation of 370 nm is 520 nm for the skin and 490 nm for the flesh. Both fluorescence intensity of skin and flesh changed during storage. Although both changes could affect the fluorescence images, confirming the previous result, the changes of the skin fluorescence are strong enough to be observed with an imaging method. Classification of fresh and spoilage tomato samples using weight loss and images were also conducted using a Partial Least Square-Discriminant Analysis (PLS-DA) model with 92% accuracy. These results demonstrate the potential of fluorescence imaging to monitor tomato freshness during storage.

DOI： 10.1088/1755-1315/733/1/012016

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier BV  

Conventionally, biochemical analysis is used to estimate the freshness of fish products, but this method is destructive, technically demanding and time consuming. In this study, the fluorescence properties of raw fisheyes of Japanese dace (Tribolodon hakonensis) fish were investigated using spectrofluorometer during 4 degrees C storage. Subsequently, according to the results of the spectrofluommeter, fluorescence imaging system was established with 365 nm UV LED to capture the fluorescence images using a common color camera. The color components from fluorescence images of pupil and iris were extracted to establish a prediction model for a 'standard freshness index' of K value which was acquired by using biochemical analysis using partial least square regression method. From the results, RMSECV of 3.5% and R-2 of 0.92 was realized. This study demonstrated that the UV-fluorescence imaging technique has a potential to estimate the fish freshness non-destructively during storage.

DOI： 10.1016/j.jfoodeng.2020.110111

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Royal Society of Chemistry (RSC)  

<p>We investigated the autofluorescence of tomato surface tissues during overripening. Microscopic images and fluorescence spectra of tissues were examined, revealing that the autofluorescence changes were related to the epidermis and the cuticle.</p>

DOI： 10.1039/d0pp00125b

Scopus

PubMed

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER  

The timing of harvest date for 'Hayward' kiwifruit (Actinidia deliciosa (A.Chev.) C.F.Liang & A.R.Ferguson. cv. 'Hayward') affects its storage life and eating quality. The common method for determination of maturity (Harvest Index) is the soluble solid content (SSC), with a minimum standard of 6.2 %. Measurement of SSC, using a hand-held refractometer, is simple and cheap, but it is destructive and laborious. In this study, we explore the potential for color and fluorescence image features to provide the basis for fast, non-destructive, and portable means of determining the Harvest Index. The most prominent fruit fluorescence excitations and emissions during fruit maturation were identified using excitation-emission matrices (Ex: 280-720 nm, Em: 300-750 nm) measured with Front Face Fluorescence Spectroscopy. The most sensitive excitation-emission wavelengths (Ex: 370 nm, Em: 400-600 nm) that correlated with SSCs were selected using partial least squares regression and were used to develop a double lighting imaging system which captures color and UV-fluorescence images. A SSC prediction model was established based on color and UV-fluorescence images. The results from this system had a root mean square error of validation and correlation coefficient relationship with standard SSCs of 0.39 and 0.94, respectively. This study demonstrated that the developed double lighting imaging system has the potential to non-destructively monitor kiwifruit maturation and determine optimum harvest by using the Harvest Index.

DOI： 10.1016/j.postharvbio.2019.111113

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER  

The potential of UV-induced fluorescence imaging was investigated as a non-destructive tool to monitor postharvest quality degradation of tomatoes harvested at the red stage and stored at 25 degrees C. The fluorescence images (excitation at 365 nm) were found to be a better indicator of tomato quality degradation than color images after color saturation. Tomatoes were stored at 25 degrees C for 9 d. The changes in color and fluorescence of tomato were evaluated by two types of images: Color and fluorescence images. A conventional colorimeter was also used for as a reference. Changes in the RGB ratio for these two types of images were opposite. In the color images, the G ratio decreased rapidly for the initial 3 or 5 d and then stabilized afterwards. On the other hand, in the fluorescence images, the G ratio increased continuously up to 9 d. Given that temperature conditions during transportation and storage of tomatoes is not always ideal, the results from this research provide the foundation for developing a postharvest monitoring system of mature tomato quality degradation.

DOI： 10.1016/j.postharvbio.2019.111031

Web of Science

Scopus

researchmap

Publishing type：Research paper (scientific journal)  

Determining the index for monitoring the freshness of green pepper during storage is still a challenge to be solved in research to avoid food loss, linked to the economical loss. The aim of the present study was to investigate the potentiality of fluorescence spectroscopy for the determination of the freshness index. Time series fluorescence characteristics from different parts of green pepper (Capsicum annuum L.) at different temperatures of storage were determined. Three replicate measurements of Excitation and Emission Matrix (EEM) fluorescence were conducted on every single evaluation during 20 days of storage with a 1-day interval starting from day 4 after harvest. Physical evaluation of color change, firmness, and weight loss were observed to have a correlation with the EEM fluorescence intensity. It was observed that fluorescence components could be extracted from green pepper, the intensity of chlorophyll-a EEM significantly dropped after day 16th from 2822 a.u and 2810 a.u to 2038 a.u and 2106 a.u in day 20th stored at 20 °C and 4 °C respectively as well as the color change behaved the same as the R/G value increased from 0.541 and 0.535 to 0.655 and 0.610 at 20 °C and 4 °C respectively. Finally, it is suggested that two suspected flavonoids substances with EEM 230-nm/310 nm and 270-nm/310 nm are potential to be a probe for freshness index in green pepper as the ratio of these EEMs increased linearly during storage with R2 0.96 and R2 0.91 for both temperatures 20 °C and 4 °C respectively.

DOI： 10.1016/j.compag.2020.105850

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：UNIV PUTRA MALAYSIA PRESS  

The potential of fluorescence technology for monitoring Miyauchi Iyokan citrus during post-harvest treatment was investigated in this research. Citrus fruits were harvested when still a greenish-yellow color with a low soluble solids (SS)/acid ratio. Dark storage of fruits at 80-90% of RH and 6-10 degrees C for sixty days is expected to increase the quality of the fruits (becoming reddish orange in color and having a high SS/acid ratio). However, monitoring the quality during the treatment is substantial. In general, farmers monitored the quality by seeing the appearance, however, this way is subjective. Thus, the fluorescence technique was proposed since it was objective, relatively cheap and easy to apply. Two main fluorescence compounds from peel, polymethoxylated flavones (PMFs) (Ex. 370 nm/Em. 540 nm) and tryptophan-like (Ex. 260 nm/Em. 330 nm) compounds were found, and PMFs were used in this research since it is an essential constituent for the fruit quality. This work demonstrated that during treatment bright yellow color (suspected PMF compounds) had appeared when excited under 365 nm with UV-light from the beginning of storage period until day eighty, however, day fifty and sixty showed stronger intensity. Furthermore, SS/acid ratio reached the highest peak in day sixty. In addition, on day sixty an unpleasant odor appeared, which might be related to the off-flavor condition of metabolic excess. These results demonstrate the potential of fluorescence to monitor citrus fruit quality changes during postharvest treatment

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier B.V.  

The main fluorescent compounds in Japanese dace fish (Tribolodon hakonensis) eye fluid associated with freshness were distinguished and their time-dependent changes with storage were observed. For this experiment 95 fish were stored at 20 °C for 36 h, meat from the dorsal part was sampled at different storage times and used to measure K value, a standard freshness index. At the same time eye fluid was collected from the fish for fluorescence spectra acquisition and biochemical analysis. K value results showed the fish remained fresh up until 18 h of storage, and then deteriorated quickly thereafter. While aromatic proteins and amino acids were confirmed to be the main fluorescent compounds in eye fluid, they showed a complicated change during storage. Fluorescent compounds of uric acid, closely associated with freshness, had low intensity values at the start of storage, with values raising sharply later in storage
showing an exponential increase during storage. Dityrosine was found to be present only at a very late stage of storage. These results indicate the connection between specific fluorescent compound changes and the progression of storage could be employed as a meaningful predictor of fish freshness.

DOI： 10.1016/j.eaef.2018.01.001

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：TAYLOR & FRANCIS INC  

Fluorescence characteristics of uric acid in Red Sea bream (Pagrus major) eye fluid was explored as a potential rapid and simple assessment for fish freshness. To investigate this, eye fluid samples were collected during storage at 22 +/- 2 degrees C for standard uric acid measurements by high-performance liquid chromatography at 12h intervals up until 36h storage. Simultaneously, uric acid fluorescence spectroscopy measurements by fluorophotometer at 3h intervals up until 36h storage were made. High-performance liquid chromatography results showed the concentration of uric acid increased with storage time in the Red Sea bream eye fluid; changes similar to those observed in Japanese dace eye fluid, only differing in concentration and rate of accumulation. The fluorescence signals of uric acid in Red Sea bream eye fluid increased with storage time, which the high-performance liquid chromatography results confirmed. To further explore this, uric acid fluorescence signals were plotted against a standard fish freshness indicator K value, which is calculated from the concentration of adenosine triphosphate and its breakdown products using paper electrophoresis method. A good exponential relationship between these two parameters (determination coefficient of 0.94). A high linear correlation between the predicted K value from the uric acid fluorescence signals and the measured K value (determination coefficient of 0.94 and root mean square error of prediction of 6.37%) indicate uric acid fluorescence characteristics in fish eye fluid has a high potential to be employed as a new, fast and simple method to assess fish freshness.

DOI： 10.1080/00387010.2018.1501395

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：MDPI  

Monitoring the maturation process of Satsuma mandarin (Citrus unshiu Marc.) by determining the soluble solids (SS) and acid content non-destructively is needed. Fluorescence components potentially offer such means of accessing fruit maturity characteristics in the orchard. The aim of this study was to determine the potential of fluorescence spectroscopy for monitoring the stage of citrus maturity. Four major fluorescent components in peel and/or flesh were found including chlorophyll-a (excitation (Ex) 410 nm, emission (Em) 675 nm) and chlorophyll-b (Ex 460 nm, Em 650 nm),polymethoxyflavones (PMFs) (Ex 260 nm and 370 nm, Em 540 nm), coumarin (Ex 330 nm, Em 400 nm), and a tryptophan-like compound (Ex 260 nm, Em 330 nm). Our results indicated a significant (R-2 = 0.9554) logarithmic ratio between tryptophan-like compoundsExEm and chlorophyll-aExEm with the SS:acid ratio. Also, the log of the ratio of PMFs from the peel (ExExEm was significantly correlated with the SS:acid ratio (R-2 = 0.8207). While the latter correlation was not as strong as the former, it does demonstrate the opportunity to develop a non-destructive field measurement of fluorescent peel compounds as an indirect index of fruit maturity.

DOI： 10.3390/horticulturae3040051

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：MDPI  

© 2017 by the authors. Licensee MDPI, Basel, Switzerland. Red sea bream (Pagrus major) scale fluorescence characteristics were identified as a potential rapid and non-destructive means for assessing the fish’s freshness. To investigate this, live red sea breams were purchased, slaughtered, and prior to measurement, stored at 22 ± 2◦C for 27 h. During subsequent storage, the K value of the dorsal meat—as a standard freshness indicator—along with front-face fluorescence spectra of representative dorsal scales, were measured simultaneously at 3 h intervals. Two major fluorescent peaks, A and B, were identified with excitation and emission wavelength pairs of 280/310 nm and 340/420 nm, which were mainly contributed to by tyrosine and collagen, respectively. Subsequent analysis showed that the fluorescence intensity ratio of peak B to A (IB/IA) increased linearly during storage (R2 = 0.95) and is proposed as a potential non-destructive index of fish freshness. Thus, our results suggest that the fluorescence characteristics of fish scales can be used to assess fish carcass freshness during storage.

DOI： 10.3390/fishes2030010

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CERAMIC SOC JAPAN-NIPPON SERAMIKKUSU KYOKAI  

Bimodal porous alumina was prepared from the solution with aluminum chloride and 1,2-propylene oxide by adding propylene glycol oligomers (PPG). Because of hydrophobic nature of PPG, the addition of PPG induces phase separation during sol-gel reaction, and macroporous morphologies are formed by fixing transitional structure of phase separation. Since ethanol works as a co-solvent, the macropore size of the obtained gel can be increased by decreasing ethanol content. Change in the concentration of other constituents such as PPG has also an effect to control morphologies through changing the timing of phase separation and sol-gel transition. (C) 2017 The Ceramic Society of Japan. All rights reserved.

DOI： 10.2109/jcersj2.17062

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (international conference proceedings)   Publisher：American Society of Agricultural and Biological Engineers  

This study aims to develop an accurate estimation model of fish freshness during storage using fluorescence excitation-emission matrix (EEM) spectroscopy of fish eye fluid combined with multivariate analysis. The fluorescence EEM data from the eye fluid of 52 fish (Japanese Dace) were collected during storage at 20°C. Simultaneously, standard fish freshness K values were measured using a paper electrophoresis technique. The normalized fluorescence EEM spectra and the K values were then modeled using a three-way partial least square regression method. The regression model had a determination coefficient of calibration (R2 cal) of 0.93, prediction (R2pred) of 0.92, a root mean square error of cross validation (RMSECV) of 8.68%, and a root mean square error of prediction (RMSEP) of 6.63%. These results confirm fish freshness can be accurately estimated by fluorescence excitation-emission matrix (EEM) spectroscopy combined with multivariate analysis.

DOI： 10.13031/aim.20162456450

Scopus

researchmap

Language：English   Publishing type：Research paper (international conference proceedings)  

Fluorescence imaging has been used to detect fruit surface damage, but has not yet been applied to vegetables, such as green pepper. In this report, we extract and identify fluorescent components from the exocarp (skin) of green pepper. The fluorescence excitation and emission wavelengths of these extracted compounds were determined using a fluorescence spectrophotometer and identified using nuclear magnetic resonance spectroscopy and mass spectrometry. Red and blue fluorescent components with excitation and emission wavelengths 667-685 nm and 400-438 nm respectively, were found. In subsequent research, the red fluorescent compounds were targeted, as these compounds have a higher fluorescence intensity, around 97 a.u. Pheophytin a is one of these red fluorescent compounds, appearing in the mass spectrum at 871 m/z. Furthermore, when a fluorescence imaging system was set up, with halogen illumination, it was shown that this system could successfully detect surface damage in green pepper.

Scopus

researchmap

Language：Japanese   Publishing type：Research paper (bulletin of university, research institution)   Publisher：愛媛大学教育・学生支援機構  

CiNii Books

researchmap

Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：水産増殖談話会  

Akoya oyster disease (A.O.D.) induces high mortality and discolors the soft tissue of Japanese pearl oysters. To examine the mechanism of these phenomena, soft tissues from healthy and diseased pearl oysters were ground, and components were extracted using ethyl alcohol. The homogenate was stored for one month in a dark and cool environment, and then filtered. The extract from diseased pearl oysters exhibited significant cytotoxicity to pearl oyster hemocytes. Furthermore, extraction of the diseased pearl oyster tissue yielded significant amounts of phytosterols and cholesterol compared to healthy pearl oysters. Thus, our results suggest that the disease disrupts the synthesis pathway between cholesterol and sex hormones. We conclude that cytotoxins induce metabolic abnormalities like sterol metabolic abnormalities, which may play a role in sexual maturation.

DOI： 10.11233/aquaculturesci.61.183

J-GLOBAL

researchmap

Language：Japanese   Publishing type：Research paper (bulletin of university, research institution)  

J-GLOBAL

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier B.V.  

Fluorescence imaging has been used to detect peel defects in many citrus varieties, but not in lemon and yuzu. In this study, we extract and identify fluorescent components from the peel of lemon and yuzu. The characteristics of excitation and fluorescence of these extracted components were determined, and their identity clarified using NMR spectroscopy. Extracted fluorescent components for both lemon and yuzu have a coumarin structure. Two coumarins (5-7-dimethoxycoumarin,5-geranyloxy-7-methoxycoumarin)were identified in lemon and one(5-geranyloxycoumarin)in yuzu. Their excitation and fluorescence wavelength were observed at 320-330nm and 380-400nm,respectively. Moreover, when a fluorescence imaging system was set-up with UV-A illumination, it was shown that this system can detect peel defects in lemon, and to a lesser extent in yuzu.

DOI： 10.1016/S1881-8366(13)80004-3

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier B.V.  

A study was conducted to investigate the best wavelengths for fluorescence excitation and the resulting fluorescence wavelengths in the range of 300-700 nm with citrus peels taken from 15 varieties, which are concerned with detection of surface defects of citrus fruits. Characteristics of UV absorbance, excitation and fluorescence spectra were observed by variety, and principle components analysis (PCA) and discriminate analysis (DA) were used to categorize the citrus varieties by fluorescence intensity levels in order to give some tips for optimizing the fluorescence imaging based machine vision system. The observed proper excitation wavelength for best fluorescence emmision and resulting peak fluorescence wavelength varied variety to variety and ranged from 350 to 380 nm and 490 to 540 nm respectively. The selected varieties of citrus were categorized successfully into four groups of known fluorescence level, namely strong, medium, weak and no fluorescence groups.

DOI： 10.1016/S1881-8366(12)80008-5

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：水産増殖談話会  

アコヤガイ赤変病が発生以来、収穫された真珠にレンガ色の真珠（濁り玉）の割合が増加した。この真珠は収穫された真珠の有機物を除去する脱色作業でも除去されないことが多いため、真珠生産者では商品価値のある真珠の収量は激減した。そこで、レンガ色の正体を明らかにするため、濁り珠を破砕し抽出した真珠の色素のNMR分析と、電子顕微鏡による正常な真珠との結晶構造を比較した。色素のNMR分析では、これまで報告されたメラニンのほかに、アコヤガイ体内のラジカル損傷産物である過酸化脂質が検出された。一方、電子顕微鏡観察では、濁り珠は正常な真珠に比べ稜柱層が有意に厚いことがわかった。抽出された色素は、真珠加工会社の脱色過程で除去されることから、レンガ色の正体は厚く形成された稜柱層にあると考えられた。

DOI： 10.11233/aquaculturesci.59.573

CiNii Books

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：WORLD SCI PUBL CO INC  

Facing zinc bisporphyrins connected with diethanoanthracene and diethanonaphthacene (syn-1 and syn-2) are prepared by double [3+1] porphyrin synthesis of tripyrranedicarbaldehyde with syn-5,11-dimethoxy-4,6,10,12-tetrahydro-4,12;6,10-diethanoanthracene[2,3-c;7,8-c']dipyrrole and syn-4,7,11,14-tetrahydro-4,14;7,11-diethanonaphthacene[2,3-c;8,9-c']dipyrrole. These bisporphyrins contain large clefts with different sizes capable for complexation with fullerenes such as C-60 and C-70. These designed syn-oriented bisporphyrins serve as effective and selective molecular tweezers for C-70. Binding affinity of the zinc bisporphyrins, namely, syn-1 and syn-2, towards C-60 and C-70 in solution is determined by employing UV-vis spectrophotometric technique. Values of binding constants (K) in toluene for the non-covalent complexes of syn-1 with C-60 and C-70 are estimated to be 3.1(4) x 10(4) and 5.0(2) x 10(5) M-1, respectively, and those of syn-2 with C-60 and C-70 are enumerated to be 2.1(4) x 10(4) and 1.70(13) x 10(5) M-1, respectively. Binding of C-60 and C-70 in the clefts of syn-1 and syn-2 is clearly demonstrated by the crystal structures of C-60/syn-1, C-70/syn-1, C-60/syn-2, and C-70/syn-2 complexes. In the crystal structures with C-70, the directions of the long axis of C-70 are found to be quite different: in the case of C-70/syn-1 complex the axis lies perpendicularly to the line connecting two zinc atoms; however, for the C-70/syn-2 complex, the axis occupies in-plane to the same line. Both the clefts of syn-1 and syn-2 are induced to fit the included fullerenes by domed out-of-plane distortion of porphyrin rings. Moreover, the bicyclo[2.2.2]octadiene moieties of syn-1 are widened by complexation with the fullerenes, while the same moieties of syn-2 are narrowed by the complexation. Therefore, syn-1 catches the fullerenes at the shallow part of the cleft. On the other hand, syn-2 catches the fullerenes at the bottom part of the cleft. NMR experiments of the complexes in THF-d(8) also support these orientations even in solution.

DOI： 10.1142/S1088424611003872

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：IOP PUBLISHING LTD  

A radio frequency plasma was generated and maintained in water over a wide range of water conductivities (0.2-7000 mS m(-1)). The conductivity of water was changed by adding NaCl to it. The size of the plasma increased with conductivity. Although the intensity of the OH (A-X) line monotonically decreased with increasing conductivity, the generation of hydrogen peroxide and the degradation of methylene blue suggested that the number of generated OH radicals decreased with increasing conductivity in the range 0.2-80 mS m(-1) and increased in the range 80-7000 mS m(-1). Ultraviolet irradiation was found to enhance the degradation of methylene blue not only in pure water but also in high-conductivity water (similar or equal to 5000 mS m(-1)).

DOI： 10.1088/0963-0252/20/3/034016

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：IOP PUBLISHING LTD  

A radio frequency plasma was generated and maintained in water over a wide range of water conductivities (0.2-7000 mS m(-1)). The conductivity of water was changed by adding NaCl to it. The size of the plasma increased with conductivity. Although the intensity of the OH (A-X) line monotonically decreased with increasing conductivity, the generation of hydrogen peroxide and the degradation of methylene blue suggested that the number of generated OH radicals decreased with increasing conductivity in the range 0.2-80 mS m(-1) and increased in the range 80-7000 mS m(-1). Ultraviolet irradiation was found to enhance the degradation of methylene blue not only in pure water but also in high-conductivity water (similar or equal to 5000 mS m(-1)).

DOI： 10.1088/0963-0252/20/3/034016

Web of Science

Scopus

researchmap

Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：The Laser Society of Japan  

The fluorescent substances in citrus fruit peels were investigated by NMR analysis and excitation, and

DOI： 10.2184/lsj.39.255

CiNii Books

J-GLOBAL

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

A new cytotoxic imidazole alkaloid, stellettazole D, containing norsesquiterpene and aminopropylimidazolium units, has been isolated from the marine sponge Jaspis duoaster. The structure of stellettazole D was assigned on the basis of NMR, mass spectrometry, and IR spectral data. Stellettazole D has moderate cytotoxicity against a limited number of tumor cells.

DOI： 10.1246/cl.2011.186

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (international conference proceedings)   Publisher：SPIE-INT SOC OPTICAL ENGINEERING  

Defective unshu oranges (Citrus reticulate Blanco var. unshu) were sorted based on fluorescent imaging technique in a commercial packinghouse but fresh appearing unshu were rejected due to fluorescence appearing on their peel. We studied the various visible patterns based on colour, fluorescence and microscopic images, where even areas of the peel that are not obviously damaged can have fluorescence, to provide a categorization of fluorescence reasons. The categorization corresponded to: 1) hole and flow; 2) influenced by damaged or rotten fruits that have released peel oil onto it; 3) immature or poor peel quality; 4) whitish fluorescence due to agro-chemicals and 5) variation of the growing season. The identification of such patterns of fluorescence might be useful for citrus grading industry to take some initiatives to make the entire automated system more efficient.

DOI： 10.1117/12.890118

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (international conference proceedings)   Publisher：SPIE-INT SOC OPTICAL ENGINEERING  

Research was conducted to acquire knowledge of the ultraviolet and visible spectrums from 300 - 800 nm of some common varieties of Japanese citrus, to investigate the best wave-lengths for fluorescence excitation and the resulting fluorescence wave-lengths and to provide a scientific background for the best quality fluorescent imaging technique for detecting surface defects of citrus. A Hitachi U-4000 PC-based microprocessor controlled spectrophotometer was used to measure the absorption spectrum and a Hitachi F-4500 spectrophotometer was used for the fluorescence and excitation spectrums. We analyzed the spectrums and the selected varieties of citrus were categorized into four groups of known fluorescence level, namely strong, medium, weak and no fluorescence. The level of fluorescence of each variety was also examined by using machine vision system. We found that around 340-380 nm LEDs or UV lamps are appropriate as lighting devices for acquiring the best quality fluorescent image of the citrus varieties to examine their fluorescence intensity. Therefore an image acquisition device was constructed with three different lighting panels with UV LED at peak 365 nm, Blacklight blue lamps (BLB) peak at 350 nm and UV-B lamps at peak 306 nm. The results from fluorescent images also revealed that the findings of the measured spectrums worked properly and can be used for practical applications such as for detecting rotten, injured or damaged parts of a wide variety of citrus.

DOI： 10.1117/12.885640

Web of Science

Scopus

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCIENCE BV  

The degradation of methylene blue by radio frequency (RF) plasmas in water under ultraviolet (UV) irradiation was studied experimentally. When the methylene blue solution was exposed to RF plasma, UV irradiation from a mercury vapor lamp enhanced degradation significantly. A lamp without power supply also enhanced degradation since weak UV light was emitted weakly from the lamp due to the excitation of mercury vapor by stray RF power. Such an enhancement is explained by the fact that after hydrogen peroxide is produced via the recombination process of OH radicals around the plasma, OH radicals reproduced from hydrogen peroxide via the photolysis process degrade methylene blue. (C) 2009 Elsevier B.V. All rights reserved.

DOI： 10.1016/j.jhazmat.2009.09.076

Web of Science

Scopus

PubMed

researchmap

Language：English   Publisher：SPRINGER  

DOI： 10.1007/s11274-009-0137-9

Web of Science

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：SPRINGER  

We isolated and elucidated the structure of several stimulants for arbuscular mycorrhizal fungi (AMF) in water-stressed bahia grass roots. We could isolate some compounds that promoted the growth of Gigaspora margarita Becker and Hall and Glomus caledonium (Nicol. and Gerd.) Trappe and Gerd. In these compounds, tryptophan dimer (Trp-Trp) was elucidated the structure. Trp-Trp was abundantly produced in water-stressed bahia grass roots and exuded to the soil, although it was scarcely detected in non-stressed root exudates. Interestingly, this peptide strongly attracted the hyphae of Gi. margarita and G. caledonium and promoted their hyphal growth in vitro (1.8 x longer than the control). Tryptophan, however, had no effect on hyphal growth and attraction. Thus, Trp-Trp exuded from water-stressed roots would play an important role as a major signal for AMF.

DOI： 10.1007/s11274-009-0003-9

Web of Science

Scopus

researchmap

Language：English  

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier B.V.  

As basic research to develop a machine vision system to detect rotten mandarin orange, the extraction and identification of fluorescent substances contained in rotten parts of mandarin orange were conducted, and the excitation and fluorescence wavelengths of the substance were determined. Although it has been reported that damaged orange fruit skins are often fluoresced by UV light, it was suggested that fluorescent substances exist not only in the rotten parts of skins but also the normal parts of skins from this research. The fluorescent substances were extracted from 1kg of mandarin peel, and NMR analysis and mass spectrometry were conducted. From this experiment, it was found that the fluorescent substance was quite possibly heptamethylflavone and that the excitation and fluorescent wavelengths of one of the substances were 360 to 375nm and 530 to 550nm, respectively.

DOI： 10.1016/S1881-8366(09)80016-5

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Elsevier B.V.  

As basic research to develop a machine vision system to detect rotten mandarin orange, the extraction and identification of fluorescent substances contained in rotten parts of mandarin orange were conducted, and the excitation and fluorescence wavelengths of the substance were determined. Although it has been reported that damaged orange fruit skins are often fluoresced by UV light, it was suggested that fluorescent substances exist not only in the rotten parts of skins but also the normal parts of skins from this research. The fluorescent substances were extracted from 1kg of mandarin peel, and NMR analysis and mass spectrometry were conducted. From this experiment, it was found that the fluorescent substance was quite possibly heptamethylflavone and that the excitation and fluorescent wavelengths of one of the substances were 360 to 375nm and 530 to 550nm, respectively.

DOI： 10.1016/S1881-8366(09)80016-5

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

The novel alkaloids cylindradines A and B were isolated from Axinella cylindratus, and their structures were elucidated by spectroscopic analyses. Stereochemistries of these compounds were determined by X-ray analysis. Cylindradines showed moderate inhibitory activity against the murine leukemia cell line P388.

DOI： 10.1021/ol802263j

Web of Science

Scopus

PubMed

researchmap

Language：English   Publishing type：Research paper (scientific journal)  

There are many types of citrus fruit grading machine with machine vision capability. While most of them sort fruit by size, shape, and color, detection of rotten fruit remains challenging because their appearances are similar to normal parts. Objectives of this research were to investigate if fluorescence would be a good indicator of the fruit rot, and to develop an economical solution to add the rot inspection capability to an existing machine vision fruit inspection station. A machine vision system consisting of a pair of white and ultra violet (UV) LED lighting devices and a color CCD camera was proposed for the citrus fruit grading task. Since the time lag between the color and fluorescence image captures was short (14ms), it was possible to inspect color, shape, size, and rot of a fruit on the move before it leaves an existing industrial inspection chamber.

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

X-Ray crystallographic analysis and structure-activity relationship of okadaic acid revealed that the flexible cavity structure stabilized by intramolecular hydrogen bonds is important for its potent cytotoxicity.

DOI： 10.3987/COM-08-S(N)88

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：SPRINGER  

Radio frequency (RF) plasma in water was used for the degradation of methylene blue. The fraction of decomposition of methylene blue and the intensity of the spectral line from OH radical increased with RF power. RF plasma in water also produced hydrogen peroxide. The density of hydrogen peroxide increased with RF power and exposure time. When pure water (300 mL) is exposed to plasma at 310 W for 15 min, density of hydrogen peroxide reaches to 120 mg/L. Methylene blue after exposed to plasma degraded gradually for three weeks. This degradation may be due to chemical processes via hydrogen peroxide and tungsten. The comparison between the experimental and calculated spectral lines of OH radical (A-X) shows that the temperature of the radical is around 3,500 K. Electron density is evaluated to be similar or equal to 3.5 x 10(20) m(-3) from the stark broadening of the H(beta) line.

DOI： 10.1007/s11090-008-9142-2

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：MARY ANN LIEBERT, INC  

Red ginseng root (Panax Ginseng CA Meyer) has been used clinically by many Asian people for thousands of years without any detrimental effects. One of the major components of Red ginseng root is ginsenoside Rb-1 (gRb1). Previously, we showed that intravenous infusion of gRb1 ameliorated ischemic brain damage through upregulation of an anti-apoptotic factor, BCI-X-L and that topical application of gRb1 to burn wound lesion facilitated wound healing through upregulation of vascular endothelial growth factor (VEGF). In the present study, we produced dihydroginsenoside Rb1 (dgRb1), a stable chemical derivative of gRb1, and showed that intravenous infusion of dgRb1 improved spinal cord injury (SCI) as well as ischemic brain damage. As we expected, the effective dose of dgRb1 was ten times lower than that of gRb1. Intravenous infusion of dgRb1 at this effective dose did not affect brain temperature, blood pressure or cerebral blood flow, suggesting that dgRb1 rescued damaged neurons without affecting systemic parameters. In subsequent in vitro studies that focused on dgRb1-induced expression of gene products responsible for neuronal death or survival, we showed that dgRb1 could upregulate the expression of not only BCI-XL, but also a potent angiogenic and neurotrophic factor, VEGF. We also showed that dgRb1-induced expression of bcl-X-L and VEGF mRNA was HRE (hypoxia response element) and STRE (signal transducers and activators of transcription 5 (Stat5) response element) dependent, respectively.

DOI： 10.1089/neu.2006.0182

Web of Science

Scopus

PubMed

researchmap

Language：Japanese   Publisher：The Japan Society of Mechanical Engineers  

It is known that rotten parts of orange fruit fluoresce when they are excited by UV light. From an analysis of orange fruit skin, it was found that one of the major fluorescent substances was flavonoid methyl ether group whose exciting wavelength was 365nm and fluorescence wavelength was about 530nm. Based on the result, a lighting device with 120365nm-wavelength LEDs was manufactured and fluorescence images of rotten citrus fruit were acquired by a machine vision system with the three lighting devices. In this paper, a machine vision system with a pair of white and UV LED lighting devices and a color TV camera was proposed for the orange fruit grading system which could automatically detect rotten fruits.

DOI： 10.1299/jsmemecjo.2007.5.0_471

CiNii Books

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：SPRINGER  

Arbuscular Mycorrhizal (AM) fungi enhance terrestrial plant growth by forming a symbiotic relationship with the roots of its host plant. A growth stimulant for AM fungi was isolated from a brown alga Laminaria japonica Areschoug. The active substance for in vitro AM hyphal growth was isolated from 75% methanol extracts of L. japonica using a succession of chromatographic procedures, including flash chromatography equipped with an octa decyl silane (ODS) column, gel filtration chromatography and HPLC using an ODS column. Spores of Gigaspora margarita Becker & Hall, an AM fungus, were exposed to the compound in vitro, and hyphal growth of G. margarita was measured after two weeks of incubation. At 40 mg L-1, the compound significantly stimulated the in vitro hyphal growth of G. margarita, compared to the control. This compound was elucidated as 5'-deoxy-5'-methylamino-adenosine by EIMS and NMR spectrum.

DOI： 10.1007/s10811-006-9095-x

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：INST PURE APPLIED PHYSICS  

We generate a radio frequency (RF) plasma in water at an atmospheric pressure by applying an RF power of 13.56 MHz from an electrode. The plasma is in a bubble formed in water. On the basis of hydrogen spectral lines under the assumption of thermal equilibrium, the temperature of the plasma is estimated to be 4000-4500K. Spectroscopic measurements show that hydrogen and oxygen are excited in the plasma. The plasma is also obtained in tap water or NaCl solution with a high conductivity. In the solution, sodium spectral lines are observed. Colored water containing methylene blue is exposed to the plasma. The absorbence spectra of the colored water before and after exposure to the plasma suggest the decomposition of organic matter due to chemical reactions involving active species, such as OH-radicals.

DOI： 10.1143/JJAP.45.8864

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Ircinamine B was isolated from the marine sponge Dactylia sp., which was collected at Cape Sada in Japan. Based on extensive spectral analysis, the structures of the isolated metabolites were established. This novel compound showed moderate activity against the murine leukemia cell line P388 (IC50 0.28 mu g/mL). (c) 2006 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.tetlet.2006.09.020

Web of Science

Scopus

researchmap

Language：English   Publisher：Symposium on the chemistry of natural products  

DOI： 10.24496/intnaturalprod.2006.0__P-257_

CiNii Books

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PHARMACEUTICAL SOC JAPAN  

A method was developed for determining illudin S, a naturally occurring toxin in the mushroom Lampteromyces japonicus in food samples with the use of gas chromatography-mass spectrometry (GC-MS). Samples of a model food, 'Ton-jiru' (miso soup), were spiked with authentic illudin S, which was then extracted from the samples by a two-step solvent extraction with ethyl acetate and acetonitrile-n-hexane, followed by solid phase extraction using a normal phase Bond Elut SI cartridge. The recovery of illudin S from the samples was in the range of 61-74%. Illudin S was identified by its GC retention time and both electron and chemical ionization mass spectra. In the splitless injection mode, the calibration curves for peak area ratio of illudin S to anthracene (internal standard) were linear, in the range from 150 pg to 150 ng with correlation coefficients exceeding 0.997, and the detection limit was 36 pg per injection volume (1 mu l).

DOI： 10.1248/jhs.52.237

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：AMER INST PHYSICS  

The generation of microwave plasma in liquid with vapor bubbles has been achieved and will soon be applied to high-speed chemical vapor deposition. Vapor bubbles are induced from an electrode by heating. The deposition rate of diamondlike carbon films depends on the pressure and the power of the microwave supply. Polycrystalline silicon carbide is synthesized on a silicon substrate in a mixture of n-dodecane and silicone oil. The dispersion of water droplets in liquid creates many pores on the silicon carbide films. The synthesis of carbon nanotubes can be achieved in liquid benzene. (c) 2006 American Institute of Physics.

DOI： 10.1063/1.2208167

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：SPRINGER  

A compound that stimulated the growth of an arbuscular mycorrhizal (AM) fungus was isolated from 75% methyl alcohol (MeOH) extracts of a brown alga, Laminaria japonica Areschoug, using high-pressure liquid chromatography (HPLC). This compound (Compound 1) was identified as mannitol by HPLC and nuclear magnetic resonance (NMR) spectroscopy. Compound 1 and purchased polysaccharides (alginic acid, fucoidan, carrageenan and mannan from marine algae) were tested for in vitro hyphal growth of an AM fungus, Gigaspora margarita Becker and Hall. Compound 1 (50-500 mg L-1) and carrageenan (1000 mg L-1) significantly stimulated the hyphal growth of germinating spores of Gi. margarita. The application of 100 mg L-1 of Compound 1 to trifoliate orange (Poncirus trifoliata Raf.) inoculated with Gi. margarita promoted root colonization and increased plant growth. These results suggest low concentrations of mannitol are among the reasons for enhanced hyphal growth and root colonization by the application of algal extracts. Other sugar alcohols (100-300 mg L-1 of xylitol, sorbitol and meso-erythritol) also increased the hyphal growth of Gi. margarita.

DOI： 10.1007/s11104-005-4985-2

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (international conference proceedings)   Publisher：INTERNATIONAL SOCIETY HORTICULTURAL SCIENCE  

Non-gaseous growth stimulatory substances for vesicular-arbuscular mycorrhizal (VAM) fungi in 45 day-fermented bahiagrass (Paspalum notatum Flugge.) shoots and leaves were isolated and identified. The VAM growth stimulants were eupalitin and 2, 3-dihydroeupalitin. Eupalitin at concentrations high enough to stimulate the hyphal growth of VAM fungi was detected in this composted bahiagrass shoots and leaves. The results suggest that some flavonoids such as eupalitin and 2, 3-dihydroeupalitin remain even in the composted organic matter or its water extract. We indicate that the effectiveness of composted organic matter application that stimulates the growth of mycorrhizal fungi will result from not only the evolution of gaseous mycorrhizal growth stimulants from the composted organic matter but also the presence of non-gaseous ones such as flavonoids.

DOI： 10.17660/ActaHortic.2004.638.39

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：TAYLOR & FRANCIS LTD  

Increased blood-DNA breakage was observed in diseased pearl oysters. They showed significant formation of 8-hydroxydeoxyguanosine (8-OHdG) and malondialdehyde (MDA), whereas the oysters that had a low mortality rate from the disease had high activity of superoxide dismutase (SOD) and low amounts of 8-OHdG and MDA. These results suggest that radical damage had occurred only in the diseased pearl oysters with the cytolysis of their haemocytes, which was related to the mass mortality of the Japanese pearl oysters.

DOI： 10.1271/bbb.67.2470

Web of Science

Scopus

PubMed

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：SOC SYNTHETIC ORGANIC CHEM JPN  

In our continuing search for bioactive substances from marine organisms, novel alkaloids were isolated. The structures and functions of these marine alkaloids are described here.
Pinnatoxins and pteriatoxins, potent shellfish poisons, were purified from the Okinawan bivalve Pinna muricata. Pinnatoxins activate Ca2+ channels. Halichlorine was isolated from the marine sponge Halichondria okadai. This compound inhibits the induction of VCAM-1. Drugs that block VCAM-I may be useful for treating coronary artery diseases, angina, and noncardiovascular inflammatory diseases. Pinnaic acids, which are cPLA(2) inhibitors, were also obtained from R muricata. Interestingly, the structures of pinnaic acids are closely related to that of halichlorine. Norzoanthamine hydrochloride, isolated from the colonial zoanthid Zoanthus sp., suppresses decreases in bone weight and strength in ovariectomized mice, and could be a good candidate for an osteoporotic drug. Aburatubolactams, inhibitors of superoxide anion generation, were isolated from Streptomyces sp.

DOI： 10.5059/yukigoseikyokaishi.61.1099

Web of Science

Scopus

researchmap

Language：Japanese   Publisher：(一社)日本神経精神薬理学会  

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Ircinamine was isolated from the marine sponge Ircinia sp.. and its structure was elucidated by detailed spectroscopic analysis. This novel compound showed moderate activity against the murine leukemia cell line P388.

DOI： 10.1246/cl.2002.464

Web of Science

Scopus

researchmap

Language：Japanese   Publisher：日本皮膚科学会-西部支部  

researchmap

Language：Japanese   Publisher：Symposium on the chemistry of natural products  

Ehime Prefecture was surrounded in the sea, and the fishery was popular from a past. Especially, many marine organisms are got around Sada Cape by the effect of the tide. Though in the Misaki town, the fishing using the network is carried out, seaweed and sponge are large obtained with the fish. However, sponge and seaweed without the value as goods are being discarded without utilizing. In our continuing search for biologically active substances from such marine organisms, three furanoterpenes (1, 2, 3) and novel alkaloid (4) were isolated from the marine sponge Ircinia sp. collected at Sada Cape. The methanolic extract of Ircinia sp. was extracted with ethyl acetate. The ethyl acetate extraction showed cytotoxic activity (IC_<50> 0.02 μg/ml) against the murine leukemia cell line P388. The residue was purified by hexane extraction, SiO_2 column chromatography, and HPLC to give cytotoxic compounds (1-4). The structures of these compounds were elucidated mainly by detailed analysis of NMR data and MS spectral data. Some kind of brown alga has also given the damage to other organism in order to put the acid out, when it is injured, while self it discolors to the green. This property seems to be the prey aversion for the predator. Polyhalogenated monoterpenes (5, 6) were isolated from such brown alga Desmarestia ligurata. The structure of 5 was deduced by the detailed comparison with known compounds. Interestingly, the result of the optical rotation estimated that 5 was an enantiomer of known compound. These compound showed weak activity against the murine leukemia cell line P388. We reported here the isolation and structural elucidation of these compounds.

DOI： 10.24496/tennenyuki.43.0_473

CiNii Books

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：園芸学会  

The isolation and identification of growth stimulants for vesicular-arbuscular mycorrhizal (VAM) fungi in the 25% methanol (MeOH) extracts of satsuma mandarin (Citrus unshiu Marc.) pomace extracts were carried out. Three compounds were isolated from the eluates by using a high pressure liquid chromatograph (HPLC). When the effect of the three compounds was tested on the in vitro hyphal growth of a VAM fungus, Gigaspora margarita, two compounds had a stimulatory effect. The two stimulants were identified as hesperidin (hesperetin-7-β-rutinoside) and narirutin (naringenin-7-β-rutinoside). Narirutin at 1 to 30 ppm and hesperidin at 1 to 10 ppm significantly stimulated the hyphal growth of G. margarita.

DOI： 10.2503/jjshs.69.385

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：JAPAN SOC HORTICULTURAL SCI  

The isolation and identification of growth stimulants for vesicular-arbuscular mycorrhizal (VAM) fungi in the 25% methanol (MeOH) extracts of satsuma mandarin (Citrus unshiu Mere.) pomace extracts were carried out. Three compounds were isolated from the eluates by using a high pressure liquid chromatograph (HPLC). When the effect of the three compounds was tested on the in vitro hyphal growth of a VAM fungus, Gigaspora margarita, two compounds had a stimulatory effect. The two stimulants were identified as hesperidin (hesperetin-7-beta-rutinoside) and narirutin (naringenin-7-beta-rutinoside). Narirutin at 1 to 30 ppm and hesperidin at 1 to 10 ppm significantly stimulated the hyphal growth of G. margarita.

Web of Science

researchmap

DOI： 10.2503/jjshs.69.385

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PHARMACEUTICAL SOC JAPAN  

Norzoanthamine is an alkaloid isolated from a colonial zoanthid, We examined the effects of norzoanthamine hydrochloride on bone weight, strength and morphology in ovariectomized mice, a postmenopausal osteoporosis model. Norzoanthamine hydrochloride significantly suppressed the decrease in femoral weight and bone biomechanical parameters caused by ovariectomy without an increase in uterine weight, This means that norzoanthamine hydrochloride does not have an estrogen-like effect on reproductive organs. Morphological observations of longitudinally ground sections of the humeri showed that norzoanthamine hydrochloride administration (2 mg/kg/d, p.o.) completely suppressed the loss of trabecular bone. Furthermore, norzoanthamine hydrochloride thickened the cortical bone. Based on these results, norzoanthamine hydrochloride may act as both a suppressor of bone resorption and an enhancer of bone formation in vivo.

DOI： 10.1248/bpb.22.920

Web of Science

Scopus

PubMed

researchmap

Language：Japanese   Publishing type：Research paper (scientific journal)   Publisher：SOC SYNTHETIC ORGANIC CHEM JPN  

In our continuing search for bioactive substances from marine organisms, four novel alkaloids, pinnatoxins, halichlorine, pinnaic acids and norzoanthamine were isolated. The structures and functions of these marine alkaloids are described here.
Pinnatoxins, potent shellfish poison, were purified form the Okinawan bivalve Pinna muricata. Pinnatoxins activate Ca2+ channel. Especially, toxicity of pinnatoxins B, C is as significant as that of tetrodotoxin. Halichlorine was isolated from the marine sponge Halichondria okadai. This compound inhibits the induction of VCAM-1 at IC50 7 mu g/ml. Drugs that block VCAM-1 may be useful for treating coronary artery diseases, angina and noncardiovascular inflammatory diseases. Pinnaic acids, cPLA(2) inhibitor, were also obtained from the Pinna muricata. Interestingly, the structures of pinnaic acids are closely related to that of halichlorine. Norzoanthamine hydrochloride, isolated from the colonial zoanthid Zoanthus sp. which suppresses the decrease in bone weight and strength in ovariectomized mice, could be a good candidate for an osteoporotic drug.

DOI： 10.5059/yukigoseikyokaishi.57.105

Web of Science

Scopus

J-GLOBAL

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：Chemical Society of Japan  

Neoilludins A and B were isolated from Lampteromyces japonicus, and their structures were elucidated by spectroscopic analysis. Their relative stereochemistries were also clarified by detailed analysis of proton-proton coupling constants and NOE experiments. These compounds are cytotoxic and exhibit antibacterial activity.

DOI： 10.1246/cl.1999.1113

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

The first total synthesis of tanzawaic acid A(GS-1302-3) is described. The stereocontrolled synthetic route allowes the absolute stereochemistry to be determined. One key transformation in the sequence involves a Stille coupling with a highly hindered aryl triflate. Examples and results of several coupling reactions are also included. (C) 1998 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(98)02226-6

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Norzoanthamine is a zoanthamine-type alkaloid from the colonial zoanthid Zoanthus sp. Norzoanthamine hydrochloride, which suppresses the decrease in bone weight and strength in ovariectomized mice, could be a good candidate for an osteoporotic drug. Although the relative configuration of norzoanthamine was established based on an X-ray crystallographic analysis, the absolute stereochemistry of norzoanthamine remains unclear. To investigate their biogenesis and mechanisms of biological action, we conducted chemical and spectroscopic studies to determine the absolute configuration of norzoanthamines.

DOI： 10.1246/bcsj.71.771

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

The absolute stereochemistry of a marine alkaloid halichlorine, which significantly inhibits VCAM-1 induction in HUVE cells, was established by synthesis of a degradation product of natural product. (C) 1998 Elsevier Science Ltd. All rights reserved.

DOI： 10.1016/S0040-4039(97)10714-6

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

The chemical substances which regulate biofilm formation were examined, and a bioassay system which uses marine bacteria with adhering properties was developed. This bioassay system is suitable for screening crude extracts from marine organisms. Using this system, those substances which regulate biofilm formation were isolated from marine organisms. For example, bis(deacetyl)solenolide D was obtained from the marine sponge Psammaplysilla; purpurea. Novel nitroalkanes were also isolated from the Okinawan sponge Callyspongia sp. Ethyl N-(2-phenylethyl)carbamate isolated from the marine bacteria SCRC3P79 (Cytophaga sp.) inhibited biofilm formation. Furthermore; the N,N-dichloro, isocyanide, isothiocyanate, and dithiocarbamate derivatives of 2-(4-nitrophenyl)ethylamine, significantly inhibited the growth of marine attaching bacteria. Interestingly, most of the marine sponges examined contained anti-biofilm compounds, such as benzoic acid, aeroplysinin-I, and bromoageliferin.

DOI： 10.1246/bcsj.70.3061

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

The chemical substances which regulate biofilm formation were examined, and a bioassay system which uses marine bacteria with adhering properties was developed. This bioassay system is suitable for screening crude extracts from marine organisms. Using this system, those substances which regulate biofilm formation were isolated from marine organisms. For example, bis(deacetyl)solenolide D was obtained from the marine sponge Psammaplysilla; purpurea. Novel nitroalkanes were also isolated from the Okinawan sponge Callyspongia sp. Ethyl N-(2-phenylethyl)carbamate isolated from the marine bacteria SCRC3P79 (Cytophaga sp.) inhibited biofilm formation. Furthermore; the N,N-dichloro, isocyanide, isothiocyanate, and dithiocarbamate derivatives of 2-(4-nitrophenyl)ethylamine, significantly inhibited the growth of marine attaching bacteria. Interestingly, most of the marine sponges examined contained anti-biofilm compounds, such as benzoic acid, aeroplysinin-I, and bromoageliferin.

DOI： 10.1246/bcsj.70.3061

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

The absolute configuration of norzoanthamine (1) was determined to be 2R, 4S, 6S, 9S, 10R, 12R, 13R, 18S, 21S, and 22S based on H-1 NMR spectral data of the MTPA esters of norzoanthamine derivatives. The possible biogenesis of zoanthamines is also proposed. (C) 1997 Elsevier Science Ltd.

DOI： 10.1016/S0040-4039(97)01238-0

Web of Science

Scopus

researchmap

Language：Japanese   Publisher：Symposium on the chemistry of natural products  

Norzoanthamine (1), is a zoanthamine-type alkaloid isolated from the colonial zoanthid Zoanthus sp. Norzoanthamines inhibit IL-6 production. Furthermore, norzoanthamine hydrochloride, which suppresses the decrease in bone weight and strength in ovariectomized mice, could be a good candidate for an osteoporotic drug. Although the relative configuration of norzoanthamine was established based on an X-ray crystallographic analysis, the absolute conformation of norzoanthamines, including zoanthamines which have been reported previously, remains unclear. To investigate their biogenesis and mechanism of biologocal action, we conducted chemical and spectroscopic studies to determine the absolute configuration of norzoanthamines. We report here the absolute stereochemistry, a proposed biogenesis and bioactivities of norzoanthamines.

DOI： 10.24496/tennenyuki.39.0_619

CiNii Books

researchmap

Language：Japanese   Publisher：静岡大学  

CiNii Books

J-GLOBAL

researchmap

Language：Japanese   Publisher：静岡大学  

CiNii Books

J-GLOBAL

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Tanzawaic acids have been isolated from Penicillium citrinum and their structures were elucidated by spectroscopic analysis. Their relative stereochemistries were also clarified by detailed analyses of H-1-H-1 coupling constants and NOE data. Tanzawaic acid B (GS-1302-1) significantly inhibits superoxide anion production in human neutrophils.

DOI： 10.1246/cl.1997.885

Web of Science

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Tanzawaic acids have been isolated from Penicillium citrinum and their structures were elucidated by spectroscopic analysis. Their relative stereochemistries were also clarified by detailed analyses of H-1-H-1 coupling constants and NOE data. Tanzawaic acid B (GS-1302-1) significantly inhibits superoxide anion production in human neutrophils.

DOI： 10.1246/cl.1997.885

Web of Science

Scopus

researchmap

Language：Japanese   Publisher：Symposium on the chemistry of natural products  

In our continuing search for biologically active substances from marine organisms, three novel alkaloids halichlorine (1), pinnaic acid (2) and norzoanthamine (4) were isolated. The structures of these alkaloids were elucidated mainly by detailed analysis of NMR data and MS spectral data. Halichlorine (1) was isolated from the marine sponge Halichondria okadai Kadota. This compound inhibits the induction of VCAM-1 (vascular cell adhesion molecule-1) at IC_<50> 7μg/ml. Drugs that block the induced expression of VCAM-1 may be useful for treating atherosclerosis, coronary artery diseases, angina and noncardiovascular inflammatory diseases. We report here the isolation and structural elucidation of 1. A cytosolic 85-kDa phospholipase (cPLA_2) exhibits specificity for the release of arachidonic acid from membrane phospholipids. Therefore, compounds that inhibit cPLA_2 activity have been targeted as anti-inflammatory agents. Pinnaic acid (2) isolated from the Okinawan bivalve Pinna muricata, inhibits the cPLA_2 activity at 0.2mM. Interestingly, the structure of 1 is closely related to that of 2. Therefore, each carbon atom has been tentatively numbered under biogenetic consideration of formation of the N-C23 bond. Further studies on chemistry of halichlorine, including its absolute configuration, biogenetic pathway and structure-activity relationships, are currently in progress in our laboratory. Biogenetic pathway of zoanthamine and norzoanthamines (4) exhibiting inhibitory effect of IL-6 production will be described here.

DOI： 10.24496/tennenyuki.38.0_79

CiNii Books

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

A new shellfish poison, pinnatoxin D, has been isolated from the Okinawan bivalve Pinna muricata. The planar structure was elucidated by extensive 2D NMR experiments, and the relative stereochemistry was deduced by NOESY data and (3)J(H-H) coupling constants. Pinnatoxin D is a novel amphoteric carbocyclic compound which is composed of a 6,7-spiro ring, a 5,6-bicyclo ring and a 6,5,6-trispiro ketal involving 15 chiral centers. (C) 1996 Elsevier Science Ltd.

DOI： 10.1016/0040-4039(96)00753-8

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

The novel alkaloid halichlorine was isolated from Halichondria okadai Kadota and its structure was elucidated by spectroscopic analysis. The relative stereochemistry was clarified by a detailed analysis of coupling constants and the NOESY spectrum. Halichlorine significantly inhibits VCAM-1 induction in cultured HUVE (human umbilical vein endothelial) cells. Copyright (C) 1996 Elsevier Science Ltd

DOI： 10.1016/0040-4039(96)00703-4

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Two novel fatty acids with cPLA(2) inhibitory activity, pinnaic acid and tauro-pinnaic acid, were isolated from the Okinawan bivalve Pinna muricata. Their structures, including the relative stereochemistry at C5, C9, C13 and C14, were elucidated by extensive 2D NMR spectroscopic analysis. Copyright (C) 1996 Elsevier Science Ltd

DOI： 10.1016/0040-4039(96)00704-6

Web of Science

Scopus

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：PERGAMON-ELSEVIER SCIENCE LTD  

Three novel nitroalkyl pyridine alkaloids, untenines A, B and C, with anti-microfouling activity. were first isolated from the Okinawan marine sponge Callyspongia sp. Their structures were elucidated on the basis of spectroscopic methods. The synthesis of untenine A was also carried out.

DOI： 10.1016/0040-4039(96)00125-6

Web of Science

Scopus

researchmap

Language：Japanese   Publisher：Symposium on the chemistry of natural products  

Search for chemical substances regulating the biofilm formation has been carried out. The assay system has been developed by using the marine bacterium possessing the attaching properties (Rhodospirillum salexigens SCRC 113). This bioassay system in laboratory is suitable for screening the crude extracts from marine organisms and the synthetic compounds. First, the adhesion inhibitory of samples was determined by monitoring amounts of polysaccharide produced by the bacteria as evaluation of the biofilm formation. Substances regulating the biofilm formation have been isolated from marine organisms. For example, bisdeacetylsolenolide D, a biofilm formation inhibitor and butenolide derivative (Hateramine), a biofilm formation accelator have been obtained from marine sponges, respectively. Ethyl N-(2-phenethyl) carbamate (1) isolated from the marine bacterium SCRC3P79 (Cytophaga sp.), remarkably inhibited the biofilm formation. The synthetic compound p-nitro derivative (2), exhibited significant inhibition of the biofilm formation. Furthermore, (2) exhibited antibacterial activity. However this assay system was replaced to new method, because procedure described here did not afford enough reproducibility of the data. Secondly, growth inhibition with tested samples against the attaching bacteria was indicated by measurement of absorbance of the culture medium and the biofilm formation was estimated. Aeroplysinin-I isolated from marine sponge Pssamaplysilla purpurea, exhibited inhibition of the biofilm formation. New nitroalkanes, (3) and (4), have been obtained from an unidentified marine sponge. The synthetic compounds (5), (6), (7) and (8) exhibited significant inhibition of the biofilm formation. As expected, the compounds (5), (6), (7) and (8) exhibited remarkable inhibition of the biofilm formation in the field experiment.

DOI： 10.24496/tennenyuki.37.0_224

CiNii Books

researchmap

Language：English   Publishing type：Research paper (scientific journal)   Publisher：CHEMICAL SOC JAPAN  

Homocereulide (1) and cereulide (2), isolated from the marine bacterium Bacillus cereus SCRC, showed extremely potent cytotoxicity. Their structures were elucidated by spectroscopic analysis and chemical degradation.

DOI： 10.1246/cl.1995.791

Web of Science

researchmap

J-GLOBAL

researchmap

J-GLOBAL

researchmap

researchmap

researchmap

J-GLOBAL

researchmap

J-GLOBAL

researchmap

J-GLOBAL

researchmap

J-GLOBAL

researchmap

Language：English   Publishing type：Research paper, summary (national, other academic conference)  

CiNii Books

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：English   Publishing type：Research paper, summary (national, other academic conference)  

researchmap

Language：English   Publishing type：Research paper, summary (international conference)  

researchmap

Language：Japanese   Publishing type：Rapid communication, short report, research note, etc. (scientific journal)  

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese   Publisher：日本皮膚科学会-西部支部  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese   Publisher：(株)協和企画  

皮膚科受診患者に健康食品・サプリメント摂取に関するアンケート調査を行い、6928名から回答を得られた。年代別利用率は19歳以下が男7%、女25%、20歳代がそれぞれ15%、51%、30歳代が18%、55%、40歳代が22%、58%、50歳代が12%、62%、60歳代が15%、62%、70歳以上が22%、65%であった。利用目的は女性では5割強が「美容」で、他は男女とも「健康保持」「疾患予防」「血液系効果」などであった。継続利用は男女とも2割弱であった。その後の経過を確認できた575名において、健康食品・サプリメントによると考えられた皮膚疾患または原疾患の増悪は46例(A群)、皮膚症状以外の訴えは77例(B群)であった。いずれも摂取中止により改善・軽快・消失した。A群のうちパッチテストなどで陽性反応を示したのは湿疹型8例、多形紅斑1例、丘疹紅斑7例、扁平苔癬型1例の合計11例であった。B群の症状は消化器症状32例、循環器系6例、頭痛6例、不眠4例、頻尿2例、その他28例であった。

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese   Publisher：The Japan Society of Mechanical Engineers  

There are many types of orange fruit grading machines with machine vision systems, but it is still difficult to detect rotten parts, because their colors are similar with normal parts. Objectives of this research are to investigate the excitation wavelengths of the substances for determination of lighting device specification, and to construct an inspection system for fruit grading by color image and for the rotten part detection by UV lighting device. From an analysis of orange fruit skins, it was found one of major fluorescent substances was flavonoid methyl whose exciting wavelength was 365nm and fluorescence wavelength was about 530nm. A machine vision system consisting of a pair of white and UV LED lighting devices and a color CCD camera was proposed for orange fruit grading. Since the time between color and fluorescence image inputs was short enough (14ms), it was considered that UV LEDs addition to white LEDs-color TV camera system installed in fruit grading lines made rotten fruit detection possible.

CiNii Books

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

CiNii Books

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

Language：Japanese   Publisher：The Physical Society of Japan  

DOI： 10.11316/jpsgaiyo.61.1.2.0_217_3

CiNii Books

researchmap

Language：Japanese  

CiNii Books

researchmap

Language：Japanese  

CiNii Books

researchmap

Language：Japanese   Publishing type：Article, review, commentary, editorial, etc. (scientific journal)  

In our ongoing search for bioactive substances from marine organisms, novel alkaloids have been isolated. Pinnatoxins and pinnamine, potent shellfish poisons, were purified from the Okinawan bivalve Pinna muricata. Pinnatoxins activate Ca2+ channels. Halichlorine was isolated from the marine sponge Halichondria okadai. This compound inhibits the induction of VCAM-1. Drugs that block VCAM-1 may be useful for treating coronary artery diseases, angina, and noncardiovascular inflammatory diseases. Pinnaic acids, which are cPLA2 inhibitors, were also obtained from P. muricata. Interestingly, the structures of pinnaic acids are closely related to that of halichlorine. Norzoanthamine hydrochloride, isolated from the colonial zoanthid Zoanthus sp., suppresses decreases in bone weight and strength in ovariectomized mice, and could be a good candidate for an osteoporotic drug. Ircinamine, purified from the marine sponge Ircinia sp., has a reactive thioester. Aburatubolactams, inhibitors of superoxide anion generation, were isolated from Streptomyces sp. This article covers the bioactive marine alkaloids that have been recently isolated by this research group.

DOI： 10.3390/md201039

Scopus

researchmap

J-GLOBAL

researchmap

Language：Japanese  

CiNii Books

J-GLOBAL

researchmap

Language：Japanese  

J-GLOBAL

researchmap

J-GLOBAL

researchmap

Language：Japanese   Publisher：The Society of Synthetic Organic Chemistry, Japan  

DOI： 10.5059/yukigoseikyokaishi.57.141

researchmap

Language：Japanese  

J-GLOBAL

researchmap

researchmap

Language：Japanese  

researchmap

Language：Japanese  

In our continuing search for biologically active substances from marine organisms, three novel alkaloids halichlorine (1), pinnaic acid (2) and norzoanthamine (4) were isolated. The structures of these alkaloids were elucidated mainly by detailed analysis of NMR data and MS spectral data. Halichlorine (1) was isolated from the marine sponge Halichondria okadai Kadota. This compound inhibits the induction of VCAM-1 (vascular cell adhesion molecule-1) at IC_<50> 7μg/ml. Drugs that block the induced expression of VCAM-1 may be useful for treating atherosclerosis, coronary artery diseases, angina and noncardiovascular inflammatory diseases. We report here the isolation and structural elucidation of 1. A cytosolic 85-kDa phospholipase (cPLA_2) exhibits specificity for the release of arachidonic acid from membrane phospholipids. Therefore, compounds that inhibit cPLA_2 activity have been targeted as anti-inflammatory agents. Pinnaic acid (2) isolated from the Okinawan bivalve Pinna muricata, inhibits the cPLA_2 activity at 0.2mM. Interestingly, the structure of 1 is closely related to that of 2. Therefore, each carbon atom has been tentatively numbered under biogenetic consideration of formation of the N-C23 bond. Further studies on chemistry of halichlorine, including its absolute configuration, biogenetic pathway and structure-activity relationships, are currently in progress in our laboratory. Biogenetic pathway of zoanthamine and norzoanthamines (4) exhibiting inhibitory effect of IL-6 production will be described here.

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

In our continuing search for biologically active substances from marine organisms, three novel alkaloids halichlorine (1), pinnaic acid (2) and norzoanthamine (4) were isolated. The structures of these alkaloids were elucidated mainly by detailed analysis of NMR data and MS spectral data. Halichlorine (1) was isolated from the marine sponge Halichondria okadai Kadota. This compound inhibits the induction of VCAM-1 (vascular cell adhesion molecule-1) at IC_<50> 7μg/ml. Drugs that block the induced expression of VCAM-1 may be useful for treating atherosclerosis, coronary artery diseases, angina and noncardiovascular inflammatory diseases. We report here the isolation and structural elucidation of 1. A cytosolic 85-kDa phospholipase (cPLA_2) exhibits specificity for the release of arachidonic acid from membrane phospholipids. Therefore, compounds that inhibit cPLA_2 activity have been targeted as anti-inflammatory agents. Pinnaic acid (2) isolated from the Okinawan bivalve Pinna muricata, inhibits the cPLA_2 activity at 0.2mM. Interestingly, the structure of 1 is closely related to that of 2. Therefore, each carbon atom has been tentatively numbered under biogenetic consideration of formation of the N-C23 bond. Further studies on chemistry of halichlorine, including its absolute configuration, biogenetic pathway and structure-activity relationships, are currently in progress in our laboratory. Biogenetic pathway of zoanthamine and norzoanthamines (4) exhibiting inhibitory effect of IL-6 production will be described here.

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

Norzoanthamine (1), is a zoanthamine-type alkaloid isolated from the colonial zoanthid Zoanthus sp. Norzoanthamines inhibit IL-6 production. Furthermore, norzoanthamine hydrochloride, which suppresses the decrease in bone weight and strength in ovariectomized mice, could be a good candidate for an osteoporotic drug. Although the relative configuration of norzoanthamine was established based on an X-ray crystallographic analysis, the absolute conformation of norzoanthamines, including zoanthamines which have been reported previously, remains unclear. To investigate their biogenesis and mechanism of biologocal action, we conducted chemical and spectroscopic studies to determine the absolute configuration of norzoanthamines. We report here the absolute stereochemistry, a proposed biogenesis and bioactivities of norzoanthamines.

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：English   Presentation type：Symposium, workshop panel (nominated)  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

Marine organisms produce novel compounds with remarkable biological activitites. Our studies have been carried out in order to clarify function-fine structure interrelationship of the super-carbon-chain compounds such as okadaic acid (2). This super-carbon-chain compound exhibits marked in vitro cytotoxicity and causes diarrhetic shellfish poisoning. Interestingly, okadaic acid is a potent inhibitor of protein phosphatases 1 and 2A. Then, the conjugated form of okadaic acid with glycine, glycookadaic acid was proved to be an anticachexia substance. Our study toward elucidation of interrelationship between fine structure and activity was started. By the NMR data analysis, we proposed importance of the formation of a flexible cavity between C1 carboxyl group and C24 hydroxyl group. Based on the flexible cavity hypothesis (Fig. 1), C24 hydroxyl group was epimerized by reaction sequencing. Epimerization at C24 was reduced the cytotoxicity of okadaic acid by two orders of magnitude. Two corresponding epimers at C27 and C7 were obtained by chemical reactions. Experiment for cytotoxicity of these epimers is currently under way. Our flexible caivity hypothesis will be supported by the fact that two epimers does not work against L1210 tumor cells.

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

It is known that rotten parts of orange fruit fluoresce when they are excited by UV light. From an analysis of orange fruit skin, it was found that one of the major fluorescent substances was flavonoid methyl ether group whose exciting wavelength was 365nm and fluorescence wavelength was about 530nm. Based on the result, a lighting device with 120365nm-wavelength LEDs was manufactured and fluorescence images of rotten citrus fruit were acquired by a machine vision system with the three lighting devices. In this paper, a machine vision system with a pair of white and UV LED lighting devices and a color TV camera was proposed for the orange fruit grading system which could automatically detect rotten fruits.

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

It is known that rotten parts of orange fruit fluoresce when they are excited by UV light. From an analysis of orange fruit skin, it was found that one of the major fluorescent substances was flavonoid methyl ether group whose exciting wavelength was 365nm and fluorescence wavelength was about 530nm. Based on the result, a lighting device with 120365nm-wavelength LEDs was manufactured and fluorescence images of rotten citrus fruit were acquired by a machine vision system with the three lighting devices. In this paper, a machine vision system with a pair of white and UV LED lighting devices and a color TV camera was proposed for the orange fruit grading system which could automatically detect rotten fruits.

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

There are many types of orange fruit grading machines with machine vision systems, but it is still difficult to detect rotten parts, because their colors are similar with normal parts. Objectives of this research are to investigate the excitation wavelengths of the substances for determination of lighting device specification, and to construct an inspection system for fruit grading by color image and for the rotten part detection by UV lighting device. From an analysis of orange fruit skins, it was found one of major fluorescent substances was flavonoid methyl whose exciting wavelength was 365nm and fluorescence wavelength was about 530nm. A machine vision system consisting of a pair of white and UV LED lighting devices and a color CCD camera was proposed for orange fruit grading. Since the time between color and fluorescence image inputs was short enough (14ms), it was considered that UV LEDs addition to white LEDs-color TV camera system installed in fruit grading lines made rotten fruit detection possible.

researchmap

Radio frequency (RF) plasma in water was used for the degradation of methylene blue. The fraction of decomposition of methylene blue and the intensity of the spectral line from OH radical increased with RF power. RF plasma in water also produced hydrogen peroxide. The density of hydrogen peroxide increased with RF power and exposure time. When pure water (300 mL) is exposed to plasma at 310 W for 15 min, density of hydrogen peroxide reaches to 120 mg/L. Methylene blue after exposed to plasma degraded gradually for three weeks. This degradation may be due to chemical processes via hydrogen peroxide and tungsten. The comparison between the experimental and calculated spectral lines of OH radical (A-X) shows that the temperature of the radical is around 3,500 K. Electron density is evaluated to be 3.5 × 10 20 m -3 from the stark broadening of the H β line. © 2008 Springer Science+Business Media, LLC.

researchmap

Language：Japanese  

researchmap

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

Marine organisms produce novel compounds with remarkable biological activitites. Our studies have been carried out in order to clarify function-fine structure interrelationship of the super-carbon-chain compounds such as okadaic acid (2). This super-carbon-chain compound exhibits marked in vitro cytotoxicity and causes diarrhetic shellfish poisoning. Interestingly, okadaic acid is a potent inhibitor of protein phosphatases 1 and 2A. Then, the conjugated form of okadaic acid with glycine, glycookadaic acid was proved to be an anticachexia substance. Our study toward elucidation of interrelationship between fine structure and activity was started. By the NMR data analysis, we proposed importance of the formation of a flexible cavity between C1 carboxyl group and C24 hydroxyl group. Based on the flexible cavity hypothesis (Fig. 1), C24 hydroxyl group was epimerized by reaction sequencing. Epimerization at C24 was reduced the cytotoxicity of okadaic acid by two orders of magnitude. Two corresponding epimers at C27 and C7 were obtained by chemical reactions. Experiment for cytotoxicity of these epimers is currently under way. Our flexible caivity hypothesis will be supported by the fact that two epimers does not work against L1210 tumor cells.

researchmap

Language：Japanese  

researchmap

Language：Japanese  

Search for chemical substances regulating the biofilm formation has been carried out. The assay system has been developed by using the marine bacterium possessing the attaching properties (Rhodospirillum salexigens SCRC 113). This bioassay system in laboratory is suitable for screening the crude extracts from marine organisms and the synthetic compounds. First, the adhesion inhibitory of samples was determined by monitoring amounts of polysaccharide produced by the bacteria as evaluation of the biofilm formation. Substances regulating the biofilm formation have been isolated from marine organisms. For example, bisdeacetylsolenolide D, a biofilm formation inhibitor and butenolide derivative (Hateramine), a biofilm formation accelator have been obtained from marine sponges, respectively. Ethyl N-(2-phenethyl) carbamate (1) isolated from the marine bacterium SCRC3P79 (Cytophaga sp.), remarkably inhibited the biofilm formation. The synthetic compound p-nitro derivative (2), exhibited significant inhibition of the biofilm formation. Furthermore, (2) exhibited antibacterial activity. However this assay system was replaced to new method, because procedure described here did not afford enough reproducibility of the data. Secondly, growth inhibition with tested samples against the attaching bacteria was indicated by measurement of absorbance of the culture medium and the biofilm formation was estimated. Aeroplysinin-I isolated from marine sponge Pssamaplysilla purpurea, exhibited inhibition of the biofilm formation. New nitroalkanes, (3) and (4), have been obtained from an unidentified marine sponge. The synthetic compounds (5), (6), (7) and (8) exhibited significant inhibition of the biofilm formation. As expected, the compounds (5), (6), (7) and (8) exhibited remarkable inhibition of the biofilm formation in the field experiment.

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Language：Japanese  

Search for chemical substances regulating the biofilm formation has been carried out. The assay system has been developed by using the marine bacterium possessing the attaching properties (Rhodospirillum salexigens SCRC 113). This bioassay system in laboratory is suitable for screening the crude extracts from marine organisms and the synthetic compounds. First, the adhesion inhibitory of samples was determined by monitoring amounts of polysaccharide produced by the bacteria as evaluation of the biofilm formation. Substances regulating the biofilm formation have been isolated from marine organisms. For example, bisdeacetylsolenolide D, a biofilm formation inhibitor and butenolide derivative (Hateramine), a biofilm formation accelator have been obtained from marine sponges, respectively. Ethyl N-(2-phenethyl) carbamate (1) isolated from the marine bacterium SCRC3P79 (Cytophaga sp.), remarkably inhibited the biofilm formation. The synthetic compound p-nitro derivative (2), exhibited significant inhibition of the biofilm formation. Furthermore, (2) exhibited antibacterial activity. However this assay system was replaced to new method, because procedure described here did not afford enough reproducibility of the data. Secondly, growth inhibition with tested samples against the attaching bacteria was indicated by measurement of absorbance of the culture medium and the biofilm formation was estimated. Aeroplysinin-I isolated from marine sponge Pssamaplysilla purpurea, exhibited inhibition of the biofilm formation. New nitroalkanes, (3) and (4), have been obtained from an unidentified marine sponge. The synthetic compounds (5), (6), (7) and (8) exhibited significant inhibition of the biofilm formation. As expected, the compounds (5), (6), (7) and (8) exhibited remarkable inhibition of the biofilm formation in the field experiment.

researchmap

Language：Japanese  

Ehime Prefecture was surrounded in the sea, and the fishery was popular from a past. Especially, many marine organisms are got around Sada Cape by the effect of the tide. Though in the Misaki town, the fishing using the network is carried out, seaweed and sponge are large obtained with the fish. However, sponge and seaweed without the value as goods are being discarded without utilizing. In our continuing search for biologically active substances from such marine organisms, three furanoterpenes (1, 2, 3) and novel alkaloid (4) were isolated from the marine sponge Ircinia sp. collected at Sada Cape. The methanolic extract of Ircinia sp. was extracted with ethyl acetate. The ethyl acetate extraction showed cytotoxic activity (IC_<50> 0.02 μg/ml) against the murine leukemia cell line P388. The residue was purified by hexane extraction, SiO_2 column chromatography, and HPLC to give cytotoxic compounds (1-4). The structures of these compounds were elucidated mainly by detailed analysis of NMR data and MS spectral data. Some kind of brown alga has also given the damage to other organism in order to put the acid out, when it is injured, while self it discolors to the green. This property seems to be the prey aversion for the predator. Polyhalogenated monoterpenes (5, 6) were isolated from such brown alga Desmarestia ligurata. The structure of 5 was deduced by the detailed comparison with known compounds. Interestingly, the result of the optical rotation estimated that 5 was an enantiomer of known compound. These compound showed weak activity against the murine leukemia cell line P388. We reported here the isolation and structural elucidation of these compounds.

researchmap

Language：Japanese  

researchmap

Language：Japanese  

researchmap

Applicant：国立大学法人愛媛大学

Application no：特願2005-514423  Date applied：2004.9

Patent/Registration no：特許第4674304号  Date issued：2011.2

特許第4674304号

J-GLOBAL

researchmap

Applicant：国立大学法人愛媛大学

Application no：JP2004014094  Date applied：2004.9

Announcement no：WO2005-033007  Date announced：2005.4

J-GLOBAL

researchmap

Applicant：株式会社テクノネットワーク四国, 三浦工業株式会社

Application no：特願2004-090106  Date applied：2004.3

Announcement no：特開2004-306029  Date announced：2004.11

J-GLOBAL

researchmap

Applicant：国立大学法人愛媛大学

Application no：特願2004-045547  Date applied：2004.2

Announcement no：特開2005-232556  Date announced：2005.9

Patent/Registration no：特許第4406692号  Date issued：2009.11

特許第4406692号

J-GLOBAL

researchmap

Applicant：株式会社テクノネットワーク四国, 田中科学機器製作株式会社

Application no：特願2004-045547  Date applied：2004.2

Announcement no：特開2005-232556  Date announced：2005.9

J-GLOBAL

researchmap

Applicant：国立大学法人愛媛大学

Application no：特願2003-340892  Date applied：2003.9

Announcement no：特開2005-105465  Date announced：2005.4

Patent/Registration no：特許第4452775号  Date issued：2010.2

J-GLOBAL

researchmap

Applicant：株式会社テクノネットワーク四国, 東レ株式会社

Application no：特願2003-340892  Date applied：2003.9

Announcement no：特開2005-105465  Date announced：2005.4

J-GLOBAL

researchmap

Applicant：株式会社山田養蜂場

Application no：特願2002-296555  Date applied：2002.10

Announcement no：特開2004-131407  Date announced：2004.4

J-GLOBAL

researchmap

Applicant：吉村 裕之

Application no：特願2002-293730  Date applied：2002.10

Announcement no：特開2004-123667  Date announced：2004.4

J-GLOBAL

researchmap

Applicant：阪中 雅広

Application no：特願2002-288637  Date applied：2002.10

Announcement no：特開2004-077456  Date announced：2004.3

J-GLOBAL

researchmap

Applicant：科学技術振興事業団

Application no：特願2001-374509  Date applied：2001.12

Announcement no：特開2003-225084  Date announced：2003.8

J-GLOBAL

researchmap

Applicant：科学技術振興事業団, 阪中 雅広, 橋本 公二

Application no：特願2001-365282  Date applied：2001.11

Announcement no：特開2002-322068  Date announced：2002.11

J-GLOBAL

researchmap

Applicant：科学技術振興事業団, 阪中 雅広

Application no：特願2001-044818  Date applied：2001.2

Announcement no：特開2002-249498  Date announced：2002.9

J-GLOBAL

researchmap

Applicant：ヤマキ株式会社

Application no：特願平10-061386  Date applied：1998.3

Announcement no：特開平11-255795  Date announced：1999.9

J-GLOBAL

researchmap

Applicant：ヤマキ株式会社

Application no：特願平10-061386  Date applied：1998.3

Announcement no：特開平11-255795  Date announced：1999.9

Patent/Registration no：特許第4236016号  Date issued：2008.12

J-GLOBAL

researchmap

Applicant：財団法人相模中央化学研究所

Application no：特願平9-125198  Date applied：1997.5

Announcement no：特開平10-147551  Date announced：1998.6

J-GLOBAL

researchmap

Applicant：財団法人相模中央化学研究所

Application no：特願平8-022199  Date applied：1996.2

Announcement no：特開平9-208587  Date announced：1997.8

J-GLOBAL

researchmap

Applicant：上村 大輔

Application no：特願平8-022200  Date applied：1996.2

Announcement no：特開平9-208588  Date announced：1997.8

Patent/Registration no：特許第3879088号  Date issued：2006.11

J-GLOBAL

researchmap

Applicant：財団法人相模中央化学研究所

Application no：特願平8-022200  Date applied：1996.2

Announcement no：特開平9-208588  Date announced：1997.8

J-GLOBAL

researchmap