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AIM: Previous research has shown that bovine herpesvirus-1 (BHV-1) in Indonesia was closely related to subtype-1 based on glycoprotein D genes. This study aimed to analyze the genetic variability of the BHV-1 isolated from the recent case in Indonesia not only based on gD but also other genes such as gB and gM and to study the homology and similarity of the sample to other BHV-1 isolated in other countries or regions. MATERIALS AND METHODS: Samples were drawn from the tracheal organ in recent field case and prepared for DNA extraction. The gB, gD, and gM were amplified using nested polymerase chain reaction (nPCR) with our specifically designed primer pair and based on the specified bands of 350 bp gB, 325 bp gD, and 734 bp gM confirmed as BHV-1. The PCR product was ligated into pGEM-T and transformed into competent Escherichia coli. The purified plasmid was subsequently sequenced. RESULTS: The virus sample isolated from the recent field case of infectious bovine rhinotracheitis (IBR) from Indonesia showed variability based on the gB, gD, and gM sequences. However, all of the genes had high similarity (98-100%) to BHV-1.2. CONCLUSION: The recent field case of IBR in Indonesia was similar to BHV-1.2.

DOI： 10.14202/vetworld.2018.1255-1261

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The new lignano-9,9'-lactones (alpha,beta-dibenzyl-y-butyrolactone lignans), which showed the higher cytotoxicity than arctigenin, were synthesized. The well-known cytotoxic arctigenin showed activity against HL-60 cells (EC50 =12 IA/I), however, it was inactive against HeLa cells (EC50 > 100 mu M). The synthesized (3,4-dichloro, 2'-butoxy)-derivative 55 and (3,4-dichloro, 4'-butyl)-derivative 66 bearing the lignano9,9'-lactone structures showed the EC50 values of 10 mu M and 9.4 mu M against HL-60 cells, respectively. Against HeLa cells, the EC50 value of the derivative 66 was 27 mu M. By comparing the activities with the corresponding 9,9'-epoxy structure (tetrahydrofuran compounds), the importance of the lactone structure of 55 and 66 for the higher activities was shown. The substituents on the aromatic ring of the lignano-9,9'-lactones affected the cytotoxicity level, observing more than 10-fold difference. (C) 2017 Published by Elsevier Ltd.

DOI： 10.1016/j.bmcl.2017.06.070

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The structure-activity relationship of the antifungal fluorinated dihydroguaiaretic acid derivatives was evaluated. Some of the newly synthesized lignan compounds were found to show higher antifungal activity against phytopathogenic fungi such as Alternaria alternata (Japanese pear and apple pathotypes) and A. citri than the lead compound, 3-fluoro-3'-methoxylignan-4'-ol (3). The broad antifungal spectrum of 3'-hydroxyphenyl derivative 16 was observed, and the 3'-fluoro-4'-hydroxyphenyl derivative 38 was found to show the highest activity against the A. alternata Japanese pear pathotype, with an EC50 value of 11 mu M. The preventive effect of the potent lignan on the infection of A. alternata in the Japanese pears leaves was also shown.

DOI： 10.1021/acs.jafc.7b01896

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To estimate the effect of methyl group of dihydroguaiaretic acid, which shows many kinds of biological activities, on biological activity, both enantiomers of 9'-dehydroxyimperanene (5, 6) and 7,8-dihydro-9'-dehydroxyimperanene (7, 8) lacking one of the methyl groups of dihydroguaiaretic acid were synthesized. (S)-7,8-Dihydro-9'-dehydroxyimperanene (7) showed 4-6-fold higher cytotoxic activity than all stereoisomers of dihydroguaiaretic acid (2-4). The IC50 values of (S)-7,8-dihydro-9'-dehydroxyimperanene (7) against HL-60 and HeLa cells were 6.1 mu M and 5.6 mu M, respectively. Though only one of three stereoisomers of dihydroguaiaretic acid showed antibacterial activity against a gram negative bacterium, both enantiomers of 5-8 showed antibacterial activity against a gram negative bacterium. This is a Letter on biological activity of 9-norlignan, in which one of methyl groups of lignan is absent. (C) 2016 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2016.05.020

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DOI： 10.1080/09168451.2015.1123603

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In the vacuolar basic amino acid (VBA) transporter family of Saccharomyces cerevisiae, VBA4 encodes a vacuolar membrane protein with 14 putative transmembrane helices. Transport experiments with isolated vacuolar membrane vesicles and estimation of the amino acid contents in vacuoles showed that Vba4p is not likely involved in the transport of amino acids. We found that the vba4 cells, as well as vba1 and vba2 cells, showed increased susceptibility to several drugs, particularly to azoles. Although disruption of the VBA4 gene did not affect the salt tolerance of the cells, vacuolar fragmentation observed under high salt conditions was less prominent in vba4 cells than in wild type, vba1, and vba2 cells. Vba4p differs from Vba1p and Vba2p as a vacuolar transporter but is important for the drug resistance and vacuolar morphology of S. cerevisiae.

DOI： 10.1080/09168451.2015.1083401

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Avt3p, a vacuolar amino acid exporter (656 amino acid residues) that is important for vacuolar amino acid compartmentalization as well as spore formation in Schizosaccharomyces pombe, has an extremely long hydrophilic region (approximately 290 amino acid residues) at its N-terminus. Because known functional domains have not been found in this region, its functional role was examined with a deletion mutant avt3((1-270)) expressed in S. pombe avt3 cells. The deletion of this region did not affect its intracellular localization or vacuolar contents of basic amino acids as well as neutral ones. The defect of avt3 cells in spore formation was rescued by the expression of avt3(+) but was not completely rescued by the expression of avt3((1-270)). The N-terminal region is thus dispensable for the function of Avt3p as an amino acid exporter, but it is likely to be involved in the role of Avt3p under nutritional starvation conditions.

DOI： 10.1080/09168451.2016.1220819

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Fusarium oxysporum causes wilt disease in many plant families, and many genes are involved in its development or growth in host plants. A recent study revealed that vacuolar amino acid transporters play an important role in spore formation in Schizosaccharomyces pombe and Saccharomyces cerevisiae. To investigate the role of vacuolar amino acid transporters of this phytopathogenic fungus, the FOXG_11334 (FoAVT3) gene from F. oxysporum was isolated and its function was characterized. Transcription of FoAVT3 was upregulated after rapamycin treatment. A green fluorescent protein fusion of FoAvt3p was localized to vacuolar membranes in both S. cerevisiae and F. oxysporum. Analysis of the amino acid content of the vacuolar fraction and amino acid transport activities using vacuolar membrane vesicles from S. cerevisiae cells heterologously expressing FoAVT3 revealed that FoAvt3p functions as a vacuolar amino acid transporter, exporting neutral amino acids. We conclude that the FoAVT3 gene encodes a vacuolar neutral amino acid transporter.

DOI： 10.1080/09168451.2015.1058703

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In Saccharomyces cerevisiae, Avt3p and Avt4p mediate the extrusion of several amino acids from the vacuolar lumen into the cytosol. SpAvt3p of Schizosaccharomyces pombe, a homologue of these vacuolar amino acid transporters, has been indicated to be involved in spore formation. In this study, we confirmed that GFP-SpAvt3p localized to the vacuolar membrane in S. pombe. The amounts of various amino acids increased significantly in the vacuolar pool of avt3 Delta cells, but decreased in that of avt3(+)-overexpressing avt3. cells. These results suggest that SpAvt3p participates in the vacuolar compartmentalization of amino acids in S. pombe. To examine the export activity of SpAvt3p, we expressed the avt3(+) gene in S. cerevisiae cells. We found that the heterologously overproduced GFP-SpAvt3p localized to the vacuolar membrane in S. cerevisiae. Using the vacuolar membrane vesicles isolated from avt3+-overexpressing S. cerevisiae cells, we detected the export activities of alanine and tyrosine in an ATP-dependent manner. These activities were inhibited by the addition of a V-ATPase inhibitor, concanamycin A, thereby suggesting that the activity of SpAvt3p is dependent on a proton electrochemical gradient generated by the action of V-ATPase. In addition, the amounts of various amino acids in the vacuolar pools of S. cerevisiae cells were decreased by the overproduction of SpAvt3p, which indicated that SpAvt3p was functional in S. cerevisiae cells. Thus, SpAvt3p is a vacuolar transporter that is involved in the export of amino acids from S. pombe vacuoles.

DOI： 10.1371/journal.pone.0130542

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All stereoisomers of methoxybutane and fluorobutane type of 1,7-seco-2,7'-cyclolignane were synthesized and cytotoxic activities of these compounds were compared with those of all stereoisomers of butane and butanol type compounds. Both enantiomers of butane type secocyclolignane showed higher cytotoxic activity (IC50 = 16-20 mu M) than methoxy type compounds, whereas none was observed for all the stereoisomers of butanol type secocyclolignane, however, (-)-Kadangustin J showed stereospecific cytotoxic activity (IC50 = 47-67 mu M). Since (R)-9'-fluoro derivative 23 was most potent (IC50 = 19 mu M) among the corresponding fluoro stereoisomers, (R)-9'-alkyl derivatives were synthesized, hydrophobic 9'-heptyl derivative 27 showing highest activity (IC50 = 3.7 mu M against HL-60, IC50 = 3.1 mu M against HeLa) in this experiment. Apoptosis induction caused by Caspase 3 and 9 for (R)-9'-heptyl derivative 27 was observed in the research on the mechanism. A degradation of DNA into small fragments was also shown by DNA ladder assay. (C) 2014 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2014.07.033

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Cytotoxic activities of synthesized lignan derivatives were estimated by WST-8 reduction assay against HL-60 and HeLa cells to show the structure-activity relationship. The activities of some effective compounds were examined against Colon 26 and Vero cells. Dietary secoisolariciresinol (SECO, 1) and its metabolite, 9,9'-anhydrosecoisolariciresinol (2), did not show the cytotoxic activity. On the other hand, all stereoisomers of dihydroguaiaretic acid (DGA, 9,9'-dehydroxysecoisolariciresinol, 3-5) exhibited the activity (IC50: around 30 mu M). The IC50 value of (8R,8'R)-9-butyl DGA derivative 13 was around 6 mu M. This fact means that the hydrophobic group was advantageous for higher activity at 9- and 9'-positions. By the evaluation of the effect of 7and 7'-aryl group on the activity, we discovered the highest activity of (8R,8'R)-7-(3-hydroxy-4-methoxyphenyl)-7'-(2-ethoxyphenyl) DGA derivative 47 showing around 1 mu M of IC50 value, which is about 24-fold higher activity than that of natural (8R,8'R)-DGA. The derivative of dietary lignan showed the high cytotoxic activity.

DOI： 10.1021/jf5010572

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Tributyltin (TBT) has long been recognized as a major environmental pollutant that can cause significant damage to the cellular functions as well as disruption of endocrine homeostasis. TBT induces apoptosis accompanied by production of reactive oxygen species (ROS) in mammalian and yeast cells. We observed that the budding yeast cells exposed to this compound at low concentrations exhibited cell growth arrest, but not cell death. Flow cytometric analysis of yeast cells without synchronization and morphological assessment of cells synchronized at M phase by nocodazole treatment indicated that TBT-exposed Saccharomyces cerevisiae cells were arrested at G1 phase of the cell cycle. This arrest was recovered by the addition of N-acetylcysteine, suggesting the involvement of ROS production by TBT. This is the first study to evaluate the action of TBT on cell cycle events.

DOI： 10.2131/jts.39.311

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Tributyltin (TBT) has long been recognized as a major environmental pollutant that can cause significant damage to the cellular functions as well as disruption of endocrine homeostasis. TBT induces apoptosis accompanied by production of reactive oxygen species (ROS) in mammalian and yeast cells. We observed that the budding yeast cells exposed to this compound at low concentrations exhibited cell growth arrest, but not cell death. Flow cytometric analysis of yeast cells without synchronization and morphological assessment of cells synchronized at M phase by nocodazole treatment indicated that TBT-exposed Saccharomyces cerevisiae cells were arrested at G1 phase of the cell cycle. This arrest was recovered by the addition of N-acetylcysteine, suggesting the involvement of ROS production by TBT. This is the first study to evaluate the action of TBT on cell cycle events.

DOI： 10.2131/jts.39.311

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The cytotoxic activities of sesquilignans, (7S,8S,7'R,8'R)- and (7R,8R,7'S,8'S)-morinol A and (7S,8S,7'S,8'S)- and (7R,8R,7'R,8'R)-morinol B were compared, showing no significant difference between stereoisomers (IC50=24-35 mu M). As a next stage, the effect of substituents at 7, 7', and 7 ''-aromatic ring on the activity was evaluated to find out the higher activity of (7S,8S,7'R,8'R)-7,7',7 ''-phenyl derivative 18 (IC50 = 6-7 mu M). In the research on the structure-activity relationship of 7 ''-position of (7S,8S,7'R,8'R)-7,7',7 ''-phenyl derivative 18, the most potent compounds were 7,7',7 ''-phenyl derivative 18 (IC50 = 6 mu M) against HeLa cells. Against HL-60 cells, 7 ''-(4-nitrophenyl)-7,7'-phenyl derivative 33 and 7 ''-hexyl-7,7'-phenyl derivative 37 (IC50=5 mu M) showed highest activity. We discovered the compounds showed four to sevenfold potent activity than that of natural (7S,8S,7'R,8'R)-morinol A. It was also confirmed that the 7'-benzylic hydroxy group have an important role for exhibiting activity, on the other hand, the resonance system of cinnamyl structure is not crucial for the potent activity. (C) 2013 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2013.06.067

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The relationship between antifungal activity against Alternaria alternata and structure on the 7-phenyl group of (+)-dihydroguaiaretic acid ((+)-DGA) was clarified by employing 38 synthesized (+)-DGA derivatives. The results were identified by quantitative structure activity relationship (QSAR) analysis employing the Hansch-Fujita method. Some compounds showed higher activity than (+)-DGA. The compound showing highest activity was 3,5-difluorophenyl derivative 37. It was suggested that the small electron-withdrawing group at the meta-position of the 7-phenyl group is important for the higher activity by antifungal test and Hansch-Fujita analysis. The whitening activity of 3-hydroxy-4-methoxyphenyl derivative 28, 3-hydroxy-4-methoxyphenyl derivative 29, and 3-hydroxy-4-isopropoxyphenyl derivative 30 against A. alternata Japanese pear pathotype was also discovered.

DOI： 10.1021/jf4015526

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A vacuolar membrane protein, Vba2p of Schizosaccharomyces pombe, is involved in basic amino acid uptake by intact cells. Here we found evidence that Vba2p mediated ATP-dependent lysine uptake by vacuolar membrane vesicles of Saccharomyces cerevisiae. Vba2p was also responsible for quinidine sensitivity, and the addition of lysine improved cell growth on quinidine-containing media. These findings should be useful for further characterization of Vba2p.

DOI： 10.1271/bbb.130387

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Using 21 newly synthesized 7,7'-dioxo-9,9'-epoxylignane derivatives having a modified 7-phenyl group, we examined the relationship between their structure and antifungal activity against plant pathogens such as Bipolaris oryzae to determine the effects of various substituents on the antifungal activity. Compared with the lead compound having a 4-OH-3-CH3O-phenyl moiety, several analogs showed higher antifungal activity against B. oryzae, including the compound having an unsubstituted phenyl group and those having either of the following phenyl substituents: 2-OH, 4-CH3O, 4-C2H5O, 4-n-C3H7O, 4-n-C4H9O, 4-CF3O, 4-C2H5, or 4-Cl. On the other hand, the activity of compounds having a branched substituent, such as 4-i-C3H7O or 4-i-C3H7, on the 7-phenyl group or a multi-substituted phenyl group was equipotent or inferior to that of the lead compound. These results as well as correlations between the antifungal activity of the test compounds and the physicochemical parameters of the varied substituents suggest that the position of substitution on the 7-phenyl group and the incorporation of substituents with optimal physicochemical properties are important for exerting the antifungal activity. (C) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2012.08.078

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ROYAL SOC CHEMISTRY  

Flaxseed lignan, secoisolariciresinol has been reported to possess health benefits. We previously synthesized each stereoisomer of secoisolariciresinol and found that (-)-secoisolariciresinol reduces lipid accumulation and induces adiponectin production in 3T3-L1 adipocytes. Here we show the effects of (-)-secoisolariciresinol on high-fat diet-induced obesity in C57BL/6 male mice. Oral administration of (-)-secoisolariciresinol for 28 consecutive days significantly suppressed the gain of body weight. Increased serum adiponectin level and decreased gene expression of fatty acid synthase and sterol regulatory element-binding protein-1c in liver, which are related to fatty acid synthesis, were observed in the mice orally administered with (-)-secoisolariciresinol. In addition, subcutaneous injection of (-)-secoisolariciresinol also significantly suppressed the gain of body weight. Serum leptin levels were significantly increased by treating with (-)-secoisolariciresinol or (-)-enterolactone. Subcutaneous injection of (-)-secoisolariciresinol, (-)-enterolactone, or (-)-enterodiol promoted gene expression of acyl-CoA oxidase, carnitine palmitoyl transferase-1, and peroxisome proliferator-activated receptor alpha, which are related to beta-oxidation. Overall results suggest that (-)-secoisolariciresinol exerts a suppressive effect on the gain of body weight of mice fed a high-fat diet by inducing gene expression of adiponectin, resulting in the altered expression of various genes related to the synthesis and beta-oxidation of fatty acids.

DOI： 10.1039/c1fo10166h

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We have found that (-)-virgatusin and related compounds have antimicrobial and antifungal activity. To identify further biological activities of these compounds, we tested the activity of acridine orange efflux, which shows ionophore-like disruption of cellular ion homeostasis activity. After testing 31 compounds, we found that verrucosin and a related compound had disruption activity.

DOI： 10.1271/bbb.110004

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Matairesinol is one of the lignan compounds found in a variety of plant foodstuffs. We investigated the immunomodulatory effects of (-)-matairesinol in vivo and ex vivo by using mice. Although we found no significant differences in the IgG, IgA and IgM levels in the serum, the IgE level was strongly suppressed by the uptake of (-)-matairesinol in both intact and ovalbumin-immunized mice. The immunoglobulin produced by lymphocytes from the spleen was not activated by the intake of (-)-matairesinol. However, lymphocytes in such gut-associated lymphatic tissues as Peyer's patches and mesenteric lymph nodes were activated by the administration of (-)-matairesinol.

DOI： 10.1271/bbb.100781

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Paraquat (PQ) is one of the most frequently used pesticides in worldwide. In most countries, PQ is used without restrictions. To investigate the effect of PQ on myogenesis, cultures of C2C12, a useful model to study differentiation of myoblasts into myotubes, were exposed to various concentrations of PQ. Myotube formation did not occur in the presence of 50 mu M PQ. Although cell death was not observed at this concentration, growth inhibition was evident in the growth medium. Production of myosin heavy chain, a myogenesis marker protein, decreased dose dependently with the concentration of PQ, which was added to the C2C12 cell culture during differentiation. Inhibition of myogenesis by PQ was not reversed by the addition of ascorbic acid. These results show that PQ is a strong inhibitor of muscle differentiation in vitro.

DOI： 10.2131/jts.36.243

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The lectin Eucheuma serra agglutinin (ESA) is known from previous studies to specifically bind to high-mannose type N-glycans and to induce apoptotic cancer cell death in vitro. In this study, Span 80 vesicles, with an average diameter between about 200 and 400 nm, containing immobilized ESA were prepared from the nonionic surfactant Span 80, also known as sorbitan monooleate. The vesicles were investigated in vitro and in vivo to evaluate the vesicles's potential applicability as novel drug delivery system. The results obtained arepromising since the following was observed: (i)vesicular ESAhad the same hemagglutinating activity as free ESA, demonstrating its biological activity when bound to the vesicles; (ii) vesicles containing immobilized ESA decreased the viability of Colo201 cancer cells in vitro while the growth of normal cells was not affected; (iii) the vesicles showed binding to Colo201 cells in vitro and caused inhibition of cancer cell growth in nude mice to which the vesicle-treated cells were added; (iv) the vesicles diminished tumor growth after intravenous administration to nude mice which contained an implanted Colo201 tumor; (v) the vesicles showed a tendency to

DOI： 10.1016/j.ijpharm.2010.01.033

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Paraquat is one of the most widely used herbicides in the world and has been known to injure lungs, liver and skin in animals and human. Hence, it is important to understand the manner of paraquat in mammals. We studied the effect of paraquat on the immune function of mouse in vitro and in vivo. When splenocytes were cultured in vitro with various concentrations of paraquat, IgA productivity was not affected while IgG and IgM productivity decreased. On the other hand, Oral administration of paraquat for 1,2 or 3 weeks increased IgA level but decreased IgM levels in serum of mice. Similarly IgA productivity increased while IgM productivity decreased. These results suggest that paraquat perturbs the lymphocytes immunoglobulin productivity in an immunoglobulin class-dependent manner.

DOI： 10.2131/jts.35.257

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DOI： 10.1007/978-90-481-38920_35

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DOI： 10.1007/978-90-481-3892-0_62

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It is well known that heavy oil pollution results ill various negative impacts on the marine environment. Although there is a low possibility of direct exposure to heavy oil, the chemical substances contained in heavy oil may be released into the environment and accumulated by marine organisms which in turn can be taken by humans via the food chain. In this study, we examined the biological risk of heavy oil extract using the common mouse, whose genetic backgrounds and immune system are well known and relatively homologous to humans. Water-soluble fraction (WSF) was extracted from heavy oil with water and the extract orally administrated to female or male mice for 7 days. In the WSF administrated group, cystoma-like formation was observed in the ovary in approximately 80% of female mice. On the other hand, we found that the prostate gland size in male mice was markedly reduced in comparison with male control mice. Continuous administration of WSF for 28 days resulted in continued hypertrophy of the cystoma around the ovary and atrophy ill the prostate gland. In addition, it was revealed that chemical substances within WSF have estrogenic activity. A major component of heavy oil, polycyclic aromatic hydrocarbons (PAHs), is known to present estrogenic activity. It is likely that the cystoma-like formation in female mice and atrophy of prostate gland in male resulted of estrogenic substances present in the WSF which might be the PAHs.

DOI： 10.2131/jts.34.239

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DOI： 10.11491/scej.2009.0.716.0

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The antioxidant activity of butane-type lignans was evaluated. Secoisolariciresinol (SECO) and dihydroguaiaretic acid (DGA) showed higher radical scavenging activity than that of 7,7'-dioxodihydroguaiaretic acid (ODGA). SECO and DGA inhibited the oxidation of unsaturated fatty acid. Both enantiomers of DGA were also lipoxygenase inhibitors, but neither enantiomer of SECO inhibited the lipoxygenase activity.

DOI： 10.1271/bbb.80461

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We have previously demonstrated that collagen from jellyfish simulated immunoglobulin and cytokine production by human-human hybridoma line HB4C5 cells and by human peripheral blood lymphocytes (hPBL). The mode of action of the collagen as an immunostimulatory factor was investigated. The expression levels of immunoglobulin mRNAs in HB4C5 cells, and those of tumor necrosis factor (TNF)-alpha, interferon (IFN)-gamma, and transforming growth factor (TGF)-beta in hPBL were up-regulated by jellyfish collagen. In addition, this collagen activated IgM production by transcription-suppressed HB4C5 cells that had been treated with actinomycin D. This collagen also enhanced IgM production by translation-suppressed HB4C5 cells that had been treated with sodium fluoride, but was ineffective in accelerating IgM production by HB4C5 cells treated with cycloheximide. Moreover, the intracellular IgM level in HB4C5 cells treated with the post-translation inhibitor, monensin, was increased by this collagen. These results suggest that collagen from jellyfish stimulated not only the transcription activity, but also the translation activity for enhanced immunoglobulin and cytokine production.

DOI： 10.1271/bbb.80154

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All stereoisomers of goniodiol were synthesized from yeast-reduction products. The C-6 chiral centers were converted from the chiral centers of the yeast-reduction products. Stereoselective conversion of the alkene, which had been prepared from the yeast-reduction product, to glycol constructed the C-7 and C-8 stereochemistry. (+)-Goniodiol and 7-epi-(+)-goniodiol showed the highest antibacterial activity (MIC, 3.1 mM) against Yersinia intermedia.

DOI： 10.1271/bbb.80262

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The relationship between the antibacterial activity and structure of 9-O,9'-O-demethyl (+)-virgatusin (Virg 3) was examined. The conversion of hydroxy groups on the 9 and 9' positions to amino groups increased the activity. It was found that the 3'-methoxy group was more important for higher activity than the X-methoxy group on the 7'-phenyl group, and that the 3,4-methylenedioxy group on the 7-phenyl group was necessary for activity.

DOI： 10.1271/bbb.70783

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Tetra-substituted tetrahydrofuran compounds were stereoselectively prepared from benzylic hemiacetal in the neutral condition by employing the simple reagent, H-2, and a Pd catalyst. The stereoselective conversion of benzylic hemiacetal to two different stereoisomers of the tetrasubstituted tetrahydrofuran compound was observed. One of these tetrahydrofuran compounds was converted to the virgatusin stereoisomer to estimate its antimicrobiological activity.

DOI： 10.1271/bbb.70554

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Language：Japanese   Publisher：公益社団法人 化学工学会  

DOI： 10.11491/scej.2008.0.629.0

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The effect of the benzylic structure of lignan on antioxidant activity was evaluated. Secoisolariciresinol (1) and 3,4-bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran (2), which have two secondary benzylic positions without oxygen, showed the highest antioxidant activity. Optically active verrucosin (4) was synthesized for the first time in this experiment.

DOI： 10.1271/bbb.70275

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

The benzyl mesylate was employed to construct the tetrasubstituted tetrahydrofuran lignan with avoiding Friedel-Crafts type of reaction. The optically pure 7,8-trans, 7 ',8 '-trans, 7,7 '-cis, and 8,8 '-cis-virgatusin stereoisomers were synthesized. The enantiomeric excess was >> 99%.

DOI： 10.1271/bbb.70236

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

The effect of oxidation degree at the benzylic position of 2,3-dibenzyl-4-butanolide and 3,4-dibenzyltetrahydrofuran lignans on the antimicrobiological activity was examined. The highest oxidation degree at the benzylic position of 2,3-dibenzyl-4-butanolide gave the greatest activity, and 3,4-dibenzoyltetrahydrofuran showed the highest antifungal activity. The relationship between stereochemistry and activity was also examined. Both enantiomers of cis-matairesinol were synthesized for the first time, one of the cis-matairesinols showing antibacterial activity.

DOI： 10.1271/bbb.70168

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

A tabletop, frequency-agile terahertz-wave spectrometer was developed based on an injection-seeded terahertz-wave parametric generator. High-resolution (< 100 MHz) spectra of polar gases can be measured in a wide frequency region (0.6-2.4 THz) within a short time (several minutes) with this spectrometer. To demonstrate the potential of this system, the authors performed real-time detection of the absorption line due to rotational transitions of the water molecule and determined their pressure-broadening coefficient. (c) 2007 American Institute of Physics.

DOI： 10.1063/1.2716146

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The relationship between antibacterial activity of tetra-substituted tetrahydrofuran lignans (1-4) and their absolute configurations was tested. Only compound 4 among two virgatusins and two related compounds exhibited growth inhibitory activity against the Gram-positive bacteria Bacillus subtilis, Staphylococcus aureas and Listeria denitrificans. Compound 4 affected the growth of B. subtilis in a bactericidic manner, and its ability to dissipate the cytoplasmic membrane potential was investigated using the fluorescence probe 3,3'-dipropylthiadicarbocyanine iodide. These results suggested that compound 4 damages cells by causing the loss of the proton motive force and disruption of the cellular integrity of the membrane, leading to cell death. In addition, it was shown that the antibacterial activity of a lignan was closely related to its absolute configuration and functional groups.

DOI： 10.1271/bbb.60429

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Language：Japanese   Publisher：公益社団法人 化学工学会  

DOI： 10.11491/scej.2007f.0.993.0

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

A spectroscopy and imaging system using a ring cavity terahertz (THz) wave parametric oscillator was developed. We demonstrate the differentiation of tissue types in a watery microtomed biological section using differences of water concentration. The contrast of differentiation for watery tissues was improved over that of the dried tissue.

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Language：Japanese   Publisher：公益社団法人 化学工学会  

DOI： 10.11491/scej.2007.0.392.0

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：LIPPINCOTT WILLIAMS & WILKINS  

Eucheuma serra agglutinin (ESA) is a lectin derived from a marine red alga E. serra and binds specifically to mannose-rich sugar chains. Previous reports have indicated that ESA associates with several cancer cells via sugar chains on cell surfaces and induces apoptotic cell death. In this study, we investigated the effect of ESA on Colon26 mouse colon adenocarcinoma cells both in vitro and in vivo. ESA induced cell death against Colon26 cells in vitro, and the expression of caspase-3 and the translocation of phosphatidylserine in ESA-treated Colon26 cells suggested that this cell death was induced through apoptosis. An intravenous injection of ESA significantly inhibited the growth of Colon26 tumors in BALB/c mice; moreover, DNA fragmentation was detected in tumor cells following ESA treatment. These results indicated that ESA is effective as an anti-cancer drug not only in vitro but also in vivo. The side-effects of ESA were not considered to be serious because the decrease in body weight of the mice injected with it was negligible. These observations suggest that ESA has the potential to be an effective anti-tumor drug.

DOI： 10.1097/01.cad.0000224458.13651.b4

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：JAPANESE BIOCHEMICAL SOC  

For high-throughput protein structural analyses, it is essential to develop a reliable protein overexpression system. Although many protein overexpression systems, such as ones involving Escherichia coli cells, have been developed, the number of overexpressed proteins exhibiting the same biological activities as those of the native ones is limited. A novel wheat germ cell-free protein synthesis system was developed recently, and most of the synthesized proteins that should function in solution were found to be in soluble forms. This suggests the applicability of this protein synthesis method to determination of the functional structures of soluble proteins. In our previous work, we developed a selective labeling technique for amino acids having amide functional groups (other than proline residues) involving the use of several inhibitors for transaminases. This paper in turn describes a proline-selective labeling technique. Based on our results, we have succeeded in constructing a complete amino acid selective labeling technique for the wheat germ cell-free protein synthesis system.

DOI： 10.1093/jb/mvj174

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

The radical and superoxide scavenging activities of oxidized matairesinols were examined. It could be assumed that the free benzylic position was important for higher radical scavenging activity. The different level of activity was observed between 7'-oxomatairesinol (Mat 2) and 7-oxomatairesinol (Mat 3). The activity of 8-hydroxymatairesinol was lower than that of matairesinol (Mat 1). The superoxide scavenging activity of the oxidized matairesinols was also demonstrated for the first time. It is assumed that the pKa value of phenol in the oxidized matairesinols affected this activity.

DOI： 10.1271/bbb.60096

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Language：Japanese   Publisher：公益社団法人 化学工学会  

DOI： 10.11491/scej.2006f.0.434.0

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

A compact, tabletop, high-resolution THz-wave spectrometer for trace gases was developed based on an injection-seeded THz-wave parametric generator. The chambers were purged with pure nitrogen gas to avoid strong absorption of THz-wave by water vapor. THz wave spectra were measured over the wide frequency range of 0.8 to 2.4 THz with a resolution better than 100 MHz. Monitoring of sub-ppm H2O concentrations in real time was demonstrated.

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Language：Japanese   Publisher：公益社団法人 化学工学会  

DOI： 10.11491/scej.2006f.0.435.0

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Fat-free bovine milk fermented by 12 kinds of lactic acid bacteria and yeast enhanced monoclonal antibody production of human hybridoma HB4C5 cells 2.8-fold in serum-free medium. Immunoglobulin production of human peripheral blood lymphocytes (PBL) was also stimulated in vitro. IgM and IgG production of human PBL was accelerated up to 2.8-fold and 5.4-fold, respectively. Interferon-gamma production of human PBL was also accelerated 6.0-fold by 50 microg/ml of the fermented milk. However, interleukin-4 production of PBL was not affected, and tumor necrosis factor-alpha production was suppressed. The activity was enhanced 2.5-fold by the thermal treatment for 30 min at 65 degrees C and was completely lost by trypsin digestion. The findings suggested that the active substance in the fermented milk was heat stable protein. Gel-filtration and the SDS-PAGE analysis revealed that the molecular weight of the active substance was estimated as 19.0 kDa, which was not detected in fat-free bovine milk before fermentation. N-terminal amino acid sequence of the 19.0 kDa protein was highly homologous to proteose-peptone component 3 (PP3). Since molecular weight of PP3 is 28 kDa, it is suggested that the 19.0 kDa protein is derived from degradation of PP3 during fermentation of fat-free milk. Moreover, PP3 purified from fat-free milk also enhanced IgM production of HB4C5 cells.

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Language：Japanese   Publisher：公益社団法人 化学工学会  

DOI： 10.11491/scej.2005.0.207.0

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Language：Japanese   Publisher：公益社団法人 化学工学会  

DOI： 10.11491/scej.2005.0.208.0

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Language：English   Publisher：The Society of Chemical Engineers, Japan  

We will report a targeting and an anti-cancer effect of a lipid vesicle, to which <I>Euchuma Serra Agglutinin (ESA)</I> immobilized, to human colon cancer cell (Colo201) in mouse xenopathic model. The lipid vesicles were mainly composed of Span80 (sorbitan monooleate). First, the specific binding between the lipid vesicle and the cancer cell was studied for the application of the vesicle to DDS. It was preliminary confirmed that the vesicle flew smoothly in superior artery of a rabbit. As a targeting ligand (combined with the vesicle) at a Colo201, <I>Euchuma Serra Agglutinin (ESA)</I> was chosen. The ESA is a new lectin derived from a marine red alga and specifically combines with mannose-rich carbohydrate-chain, which often exists on the surface of cancer cells abundantly. <I>ESA</I> was found to specifically combine with many cancer cells, especially to colon adenocarcinoma (Colo201) and induce an apoptosis to the cancer cell. Secondly, the <I>in vivo</I> experiments toward to colon cancer therapy were carried out administrating the <I>ESA-immobilized</I> vesicles into nude mice in which human colon cancer-cell Colo201 had been implanted. Preliminary autoradiogram experiments showed the free <I>ESA</I> selectively accumulated in the tumor of the mice. Then, we prepared either <I>ESA-immobilized</I> vesicle or the vesicle entrapping anti-tumor drug (Taxotere) for using colon-cancer xenopathic model in nude mouse. Autoradiograms also showed the <I>ESA-immobilized</I> vesicles were specifically accumulated into the tumor rather than the other organ. The most effective anti-tumor effect was observed in using the <I>ESA-immobilized</I> vesicle entrapping Taxotere.

DOI： 10.11491/apcche.2004.0.500.0

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Language：English   Publisher：The Society of Chemical Engineers, Japan  

The purpose of this work is a construction of the basic manner of a human brain-tumor therapy by using an immunovesicle (antibody-immobilized vesicle) in DDS. The ERM5-1 cell was applied as a model cell of human brain-tumor, which was a mouse cell made by transgenic technology. The human brain-tumor cell was found to have a specific antigen of EGFR (Epidermal Growth Factor Receptor). The ERM5-1 cell has the antigen EGFR and the cell can be applied as a model cell of human brain-tumor cell. Anti-EGFR antibody was immobilized on the surface of the vesicle as follows. The human anti-EGFR antibody (IgG) was preliminary immobilized to a protein A, which has a binding site to Fc fragment of IgG. The EGFR-protein A complex was immobilized to a vesicle by means of the two-step emulsification. Thus, the human anti-EGFR antibody was successfully immobilized orientated to the outer direction of the vesicle surface. It was fluorometrically confirmed that the specific antigen-antibody affinity between the antibody of the vesicle and EGFR on the ERM5-1 cell well functioned <I>in vitro</I> experiments. In the vesicle, Taxsotere of anti-tumor drug was entrapped for increasing the anti-tumor effect of the vesicle. It was also confirmed from <I>in vitro</I> experiments that anti-tumor effect of the immunovesicle to the ERM5-1 cell was superior to a normal vesicle (non-immunovesicle). Moreover, the <I>in vivo</I> experiments of anti-tumor effect to the ERM5-1 cell were carried out administrating the Taxotere-entrapped immunovesicle into nude mice to which ERM5-1 cell was implanted. Superior anti-tumor effect to the ERM5-1 cell in the mice could be observed to that of the normal vesicle.

DOI： 10.11491/apcche.2004.0.501.0

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

The cloning of fgb1, the gene encoding a heterotrimeric G protein beta subunit FGB1 in Fusarium oxysporum, was performed by standard PCR techniques to evaluate the role of G protein signaling in this fungus. The full-length open reading frame spanned 1,077 nucleotides and the deduced primary structure of the protein (359 amino acid residues) showed high identity with Gbeta subunits from other organisms. Disruption of fgb1 led to decreased intracellular cAMP levels, reduced pathogenicity, and alterations in physiological characteristics, including heat resistance, colony morphology, conidia formation and germination frequency. We previously showed that most of these alterations (except germination frequency) were also observed in the disruptants of fga1, the gene for Galpha subunit FGA1 in F. oxysporum. These results suggest that FGA1 and FGB1 have partially overlapping functions in the regulation of development and pathogenicity in F. oxysporum.

DOI： 10.1007/s00294-003-0372-9

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Language：Japanese   Publisher：公益社団法人 化学工学会  

DOI： 10.11491/scej.2003f.0.1050.0

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Society of Fermentation and Bioengineering  

Pz-peptidase is an endopeptidase that cleaves the synthetic substrate Pz-peptide (4-phenylazobenzyloxycarbonyl-Pro-Leu-Gly-Pro-Arg), which was originally developed for the assay of collagenase. The Pz-peptidase gene of Bacillus licheniformis N22 was cloned and sequenced. The gene consists of 628 amino acids with a motif for zinc-dependent metalloprotease, and shares 42% amino acid identity with the oligoendopeptidase of Lactococcus lactis. This is the first report on the gene structure of a Pz-peptidase.

DOI： 10.1016/S1389-1723(99)89018-5

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Language：English   Publisher：The Phytopathological Society of Japan (PSJ)  

DOI： 10.3186/jjphytopath.63.385

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Other Link： https://jlc.jst.go.jp/DN/JALC/00084347329?from=CiNii

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

Pz-peptidase is an endopeptidase that cleaves the synthetic substrate, 4-phenylazobenzyloxycarbonyl-Pro-Leu-Gly-Pro-Arg (Pz-peptide), which was originally developed for the assay of Clostridium histolyticum collagenase (Wünsch and Heidrich, Hoppe-Seyler's Z. Physiol. Chem., 333, 149-151, 1963
Morales and Woessner, J. Biol. Chem., 252, 4855-4860, 1977). Pz-peptidase was purified from the culture filtrate of Bacillus licheniformis N22. The purified Pz-peptidase showed a molecular weight of 70,000 in SDS-polyacryl-amide gel electrophoresis and 150,000 in gel filtration. Optimal pH for cleavage of Pz-peptide was 7.8. The Pz-peptidase activity was strongly inhibited by metal chelators such as EDTA and O-phenanthroline. Substrate specificity studies indicated that Pz-peptidase cleaved oligopeptides at the Xaa-Gly site in Xaa-Gly-Pro. However, Pz-peptidase failed to hydrolyze native collage, denatured collagen, hemoglobin and casein. © 1995.

DOI： 10.1016/0922-338X(95)90603-W

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A bacterium having collagenolytic activity was isolated from soil and identified as Bacillus licheniformis. The collagenolytic enzyme was obtained in a medium containing gelatin and purified to apparent homogeneity on the basis of SDS-polyacrylamide gel electrophoresis. The purified enzyme had a molecular weight of approximately 29,000, and hydrolyzed native, insoluble collagen. In addition, the enzyme hydrolyzed soluble collagen, gelatin, hemoglobin and casein, but not synthetic oligopeptides, usually used as substrates for collagenase assay. © 1994.

DOI： 10.1016/0922-338X(94)90358-1

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The primary transcript of pnp, the gene encoding polynucleotide phosphorylase in Escherichia coli, is processed in the 5′ end region by ribonuclease III (RNase III). The unprocessed transcript shows enhanced stability compared with the processed transcript. We report here that, unlike the processed transcript, the unprocessed pnp transcript did not accept endonucleolytic attack at, at least, five cleavage sites. Sequencing analysis of the four cleavage products shows no sequence specific to all these sites, but AU rich stretches were observed at three sites. © 1992 IRL Press at Oxford University Press.

DOI： 10.1093/nar/20.4.847

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Language：English   Publishing type：Research paper (international conference proceedings)   Publisher：KLUWER ACADEMIC PUBL  

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Language：Japanese  

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Language：English   Publisher：JAPANESE SOC TOXICOLOGICAL SCIENCES  

Heavy oil is one of the most serious pollutants in marine ecosystem. The poisonous influences of the chemical substances contained in heavy oil on many kinds of marine organisms are widely studied. However, the influence of the chemical compounds in heavy oil on our health has not been cleared yet. In order to reveal the poisonous influences of these chemical compounds on mammalian reproductive system, water-soluble fraction (WSF) extracted from heavy oil was administrated to mice for 2 weeks. WSF-administrated mice were crossed with either WSF- or distilled water-administrated group for mating experiment. When WSF-administrated male mice were used as a father, it reduced not only mating ratio, but also neonatal male ratio. The numbers of sperms of WSF-administrated male mice were decreased. In addition, abnormality of sperms such as bent or twisted tail was increased approximately 6-fold by WSF intake. The level of testosterone in serum from WSF-administrated mice was lower than that from control mice. Testosterone is the most important for the spermatogenesis in vertebrate. It is supposed from these findings, the decrease in the number of sperms may relate with the reduction of sex hormone level in serum. It is suggested from these results that the chemical substances in WSF affected the sperm function in reproductive system of male mice.

DOI： 10.2131/jts.36.487

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Language：English   Publisher：JAPANESE SOC TOXICOLOGICAL SCIENCES  

ATP-binding cassette (ABC) transporter plays an important role for resistance against xenobiotics. There are eleven ABC transporter genes in the genome of fission yeast Schizosaccharomyces pombe. We examined the role of ABC transporter against the toxicity of tributyltin chloride (TBT), a widespread environmental pollutant, in cell growth. Among individual ABC transporter mutants, the growth of a mutant deficient in Bfr1p, a plasma membrane-embedded transporter, was extremely sensitive to TBT. The lethal TBT concentration inducing 50% of cell death (LC50) was 25 mu M for the parent strain and 10.2 mu m for the bfr1 Delta mutant. Thus, Bfr1p was responsible for TBT resistance in S. pombe.

DOI： 10.2131/jts.36.117

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Language：English   Publishing type：Research paper, summary (international conference)   Publisher：ELSEVIER SCIENCE BV  

DOI： 10.1016/j.jbiotec.2010.09.106

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Language：English   Publishing type：Research paper, summary (international conference)   Publisher：ELSEVIER SCIENCE BV  

DOI： 10.1016/j.jbiotec.2010.09.652

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Language：English   Publishing type：Research paper, summary (international conference)   Publisher：ELSEVIER SCIENCE BV  

DOI： 10.1016/j.jbiotec.2010.09.300

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Language：English   Publisher：TAYLOR & FRANCIS LTD  

The relationship between the structure of naturally occurring (7R,7'R,8R,8'R)-morinol B and its antifungal activity was examined. 3-Demethoxy morinol B showed much higher activity than the natural compound. The activity of the 4-butoxy-3-demethoxy derivative was higher than that of 3-demethoxy morinol B.

DOI： 10.1271/bbb.100422

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The IgE-suppressive activity of (-)-matairesinol is demonstrated, and the structure-activity relationship of (-)-matairesinol clarified. 3',4-Dihydroxy-3,4'-dimethoxylignano-9,9'-lactone showed higher IgE-suppressive activity than (-)-matairesinol without any cytotoxic activity. Some derivatives bearing a longer and more bulky alkoxy group at the 3 or 4 position showed IgE-accelerative activity.

DOI： 10.1271/bbb.100275

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Improved syntheses of optically pure (-)- and (+)-morinol C, and (-)- and (+)-morinol D were achieved by employing the Mizoroki-Heck reaction to construct the cinnamyl moiety. The protective group of the alkene substrate affected the yield of this key reaction. The reaction with a combination of the acetate-protected olefin and 4-methoxyphenylboronic acid gave the best result producing morinol C and D. All stereoisomers of morinol C and D showed cytotoxic activity, with (R,R)morinol C showing the highest antibacterial activity.

DOI： 10.1271/bbb.100255

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Language：English   Publisher：ELSEVIER SCIENCE BV  

The lectin Eucheuma serra agglutinin (ESA) is known from previous studies to specifically bind to high-mannose type N-glycans and to induce apoptotic cancer cell death in vitro. In this study, Span 80 vesicles, with an average diameter between about 200 and 400 nm, containing immobilized ESA were prepared from the nonionic surfactant Span 80, also known as sorbitan monooleate. The vesicles were investigated in vitro and in vivo to evaluate the vesicles's potential applicability as novel drug delivery system. The results obtained are promising since the following was observed: (i) vesicular ESA had the same hemagglutinating activity as free ESA, demonstrating its biological activity when bound to the vesicles; (ii) vesicles containing immobilized ESA decreased the viability of Colo201 cancer cells in vitro while the growth of normal cells was not affected; (iii) the vesicles showed binding to Colo201 cells in vitro and caused inhibition of cancer cell growth in nude mice to which the vesicle-treated cells were added; (iv) the vesicles diminished tumor growth after intravenous administration to nude mice which contained an implanted Colo201 tumor; (v) the vesicles showed a tendency to accumulate at the site of the tumor 6 h after iv. administration to nude mice. Thus, all measurements carried out indicate that this type of Span 80 vesicle can be considered as promising alternatives to conventional phospholipid-based vesicles. (C) 2010 Elsevier B.V. All rights reserved.

DOI： 10.1016/j.ijpharm.2010.01.033

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Language：English   Publisher：JAPANESE SOC TOXICOLOGICAL SCIENCES  

It is well known that heavy oil such as pollutant caused serious influences on the marine ecosystem. We may suffer from various disorders in our body via intake of marine foods polluted with heavy oil. However the influences of heavy oil on our immune system have not yet been clarified. Here we show the effects of heavy oil extracts, water-soluble fraction (WSF), methanol-soluble fraction (MSF) and ethanol-soluble fraction (ESF), on immunoglobulin production of mouse splenocytes. All extracts increased IgA productivity of splenocytes. In oral administration, shrinkage of the immune organs such as spleen or thymus was observed in only WSF-administrated mice at least during 7 days. The amount of IgG production level in splenocytes cultured medium and sera were reduced by each extract administration. A flowcytometry method, to monitor splenocytes of WSF-administrated mice, has been set up using double staining with B and T cell-specific surface antibody. The results from cell population analysis indicated that B cells, including plasma cells producing antibody were reduced. The decrease in IgG level in sera was caused by reduction of plasma cells in spleen. Hence, it is suggested that reduction of Ig production was affected by the chemical compounds contained in WSF possibly such as polycyclic aromatic hydrocarbons (PAHs) through the estrogen receptor expressed in lymphocytes.

DOI： 10.2131/jts.34.459

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Language：English   Publisher：JAPANESE SOC TOXICOLOGICAL SCIENCES  

Tributyltin chloride (TBT), an environmental Pollutant, is toxic to a variety of eukaryotic and prokaryotic organisms. Although it has been reported that TBT induces apoptotic cell death in mammalian, the action of TBT on eukaryotic microorganisms has not yet been fully investigated. In this study we examined the mechanism involved in cell death caused by TBT exposure in Saccharomyces cerevisiae. The median lethal concentration of TBT was 10 mu M for the parent strain BY4741 and 3 mu M for the pdr5A mutant defective in a major multidrug transporter, respectively. Fluorescence microscopic observations revealed nuclear condensation and chromatin fragmentation in cells treated with TBT indicating that cells underwent an apoptosis-like cell dearth. TBT-induced cell death was suppressed by deletion of the ycal gene encoding a homologue of the mammalian caspase. In parallel, reactive oxygen species (ROS) were produced by TBT. These results suggest that TBT induces apoptosis-like cell death in yeast via an Yca1 p-dependent pathway possibly downstream of the ROS production. This is the first report on TBT-induced apoptotic cell death in yeast.

DOI： 10.2131/jts.34.541

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Language：English   Publisher：TAYLOR & FRANCIS LTD  

The relationship between the stereochemistry and antimicrobial activity of butane-type lignans was clarified. All stereoisomers; of dihydroguaiaretic acid (DGA) showed both antibacterial and antifungal activity. The (+)- and (-)-7,7'-dioxodihydroguaiaretic acid (ODGA) also showed both antibacterial and antifungal activity, while meso-ODGA did not show antibacterial activity, but showed antifungal activity. No activity of any stereoisomer of secoisolariciresinol (SECO) was apparent.

DOI： 10.1271/bbb.90167

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The syntheses of all stereoisomers of tetrasubstituted tetrahydrofuran lignan were accomplished, and the antimicrobial activity was examined. The 9,9'-diol compound bearing (7R,7'R,8R,8'R) and (7R,7'S,8R,8'R) stereochemistry showed the strongest antibacterial activity against Listeria denitrificans and Bacillus subtilis, respectively. It was also found that (-)-virgatusin bearing (7S,7'R,8S,8'S) stereochemistry had strongest antifungal activity.

DOI： 10.1271/bbb.90107

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Language：English   Publisher：JAPANESE SOC TOXICOLOGICAL SCIENCES  

It is well known that heavy oil pollution results ill various negative impacts on the marine environment. Although there is a low possibility of direct exposure to heavy oil, the chemical substances contained in heavy oil may be released into the environment and accumulated by marine organisms which in turn can be taken by humans via the food chain. In this study, we examined the biological risk of heavy oil extract using the common mouse, whose genetic backgrounds and immune system are well known and relatively homologous to humans. Water-soluble fraction (WSF) was extracted from heavy oil with water and the extract orally administrated to female or male mice for 7 days. In the WSF administrated group, cystoma-like formation was observed in the ovary in approximately 80% of female mice. On the other hand, we found that the prostate gland size in male mice was markedly reduced in comparison with male control mice. Continuous administration of WSF for 28 days resulted in continued hypertrophy of the cystoma around the ovary and atrophy ill the prostate gland. In addition, it was revealed that chemical substances within WSF have estrogenic activity. A major component of heavy oil, polycyclic aromatic hydrocarbons (PAHs), is known to present estrogenic activity. It is likely that the cystoma-like formation in female mice and atrophy of prostate gland in male resulted of estrogenic substances present in the WSF which might be the PAHs.

DOI： 10.2131/jts.34.239

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The antimicrobial activity of all stereoisomers of morinols A and B was tested. All stereoisomers of morinols A and B showed antifungal activity against Alternaria alternata, especially (-)-morinol B which showed the strongest activity. The natural component, (+)-morinol A, and unnatural stereoisomer, (7S,7'S,8R,8'R)-morinol B, showed antibacterial activity against the gram-positive bacteria, Bacillus subtilis and Listeria denitrificans.

DOI： 10.1271/bbb.80536

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Language：English   Publisher：TAYLOR & FRANCIS LTD  

As we have reported, flaxseed lignan, (+)-secoisolariciresinol (SECO), (-)-SECO, and meso-SECO were stereoselectively synthesized and their biological functions were evaluated. In the present study, we focused on the effects of SECOs on the regulation of 3T3-L1 adipocytes, and identified the structure-activity relationships. Optically active SECO and meso-SECO were tested for their effects on lipid metabolism in 3T3-L1 adipocytes. (-)-SECO accelerated adiponectin production of 3T3-L1 adipocytes. On the other hand, (+)- and meso-SECO suppressed the production of adiponectin. In addition, triglyceride (TG) accumulation in 3T3-L1 adipocytes was significantly suppressed by all three SECOs tested here, as was 17 beta-estradiol, when the SECOs were added to the medium during induction of 3T3-L1 preadipocytes to adipocytes. Especially, (-)-SECO strongly reduced TG accumulation. It is well-known that SECO has estrogen-like activity. Hence the estrogen-like activity of each SECO compound was assessed. Only (-)-SECO had estrogen-like activity.

DOI： 10.1271/bbb.80393

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The antimicrobial activity of all stereoisomers of morinols A and B was tested. All stereoisomers of morinols A and B showed antifungal activity against Alternaria alternata, especially (-)-morinol B which showed the strongest activity. The natural component, (+)-morinol A, and unnatural stereoisomer, (7S,70S,8R,80R)-morinol B, showed antibacterial activity against the gram-positive bacteria, Bacillus subtilis and Listeria denitrificans.

DOI： 10.1271/bbb.80536

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Language：Japanese   Publisher：公益社団法人 化学工学会  

DOI： 10.11491/scej.2009.0.724.0

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The jellyfish extract enhanced IgM production of human hybridoma HB4C5 cells 34-fold. IgM and IgG production of human peripheral blood lymphocytes (hPBL) were also accelerated 2.8- and 1.4-fold, respectively. Moreover, IFN-gamma and TNF-alpha production by hPBL Were stimulated 100- and 17-fold, respectively. Collagenase treatment inactivated the immunostimulation activity of the jellyfish extract. In addition, purified collagen from bovine Achilles' tendon accelerated IgM production of hybridoma cells. These facts mean that collagen has immunostimulation effect, and the active substance in jellyfish extract is collagen. As the result of the investigation about the mode of action, colla-en stimulates both transcription and translation activities to enhance Ig production.

DOI： 10.1007/978-1-4020-9646-4_45

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Language：English   Publisher：ELSEVIER SCIENCE BV  

We have identified the Schizosaccharonvees pombe SPBC3E7.06c gene (fnx2(+)) from a homology search with the fiix1(+) gene involving in G(0) arrest upon nitrogen starvation. Green fluorescent protein-fused Fnx1p and Fnx2p localized exclusively to the vacuolar membrane. Uptake of histidine or isoleucine by S. pombe cells was inhibited by concanamycin A, a specific inhibitor of the vacuolar H+-ATPase. Amino acid uptake was also defective in the vacuolar ATPase mutant, suggesting that vacuolar compartmentalization is critical for amino acid uptake by whole cells. In both Delta fnx1 and Delta fnx2 mutant cells, uptake of lysine, isoleucine or asparagine was impaired. These results suggest that Jnx1(+) and fnx2(+) are involved in vacuolar amino acid uptake in S. pombe. (C) 2008 Federation of European Biochemical Societies. Published by Elsevier B.V. All rights reserved.

DOI： 10.1016/j.febslet.2008.05.017

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Language：English   Publisher：TAYLOR & FRANCIS LTD  

The first stereoselective synthesis of meso-secoisolariciresinol is reported. A comparison of the cytotoxic and immunosuppressive activity between meso-secoisolariciresinol and optically active secoisolariciresinols was similarly performed for the first time. Both enantiomers of secoisolariciresinol accelerated IgM production, although meso-secoisolariciresinol did not affect IgM production. Only meso-secoisolariciresinol showed cytotoxic activity.

DOI： 10.1271/bbb.70358

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Language：English   Publisher：JAPANESE SOC PLANT CELL & MOLECULAR BIOLOGY  

It is well known that DNA methylation is involved in the control of transposable elements in eukaryotic cells. Recent studies indicate that demethylation of DNA in a mutant of Chlamydomonas and Arabidopsis causes transcriptional activation and mobilization of transposons. In this report, transposition of a retrotransposon was investigated in the phytopathogenic fungus Fusarium oxysporum treated with 5-azacytidine (5azaC), a reagent that causes reduction in the DNA methylation level. The results showed elevated transposition frequency in 5azaC-treated isolates when they were incubated for a long time. However, increase of retrotransposon transcripts was not observed, suggesting that the retrotransposon was mobilized by a mechanism other than its transcriptional activation.

DOI： 10.5511/plantbiotechnology.24.345

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The 7′,8′-stereochemistry of the tetrahydropyran sesquineolignans morinols A and B was determined as threo via synthetic studies and by comparison of NMR data of 7′,8′-threo-morinol and 7′,8′-erythro-morinol. This study also confirmed that the biosynthetic process produces enantiomeric mixtures of morinols A and B. This was ascertained by comparing the specific rotations of synthesized morinols A and B with those of naturally occurring morinols A and B. © 2007 American Chemical Society and American Society of Pharmacognosy.

DOI： 10.1021/np060461j

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Language：English   Publisher：TAYLOR & FRANCIS LTD  

Antifungal activities of the optically pure (&gt; 99%ee) (-)- and (+)-virgatusin, a tetra-substituted tetrahydrofuran lignan, were tested. (-)-Virgatusin, which is a natural product, showed highest antifungal activity against Colletotrichum lagenarium. Research on its structure-activity relationship was also performed. It was shown that two methoxy groups on 9 and 9' positions and a 3,4-methylenedioxyphenyl group on the 7 position of virgatusin were essential for high fungal growth inhibition. The part on 7'-phenyl group was not essential for activity. The 7'-(4-methoxyphenyl) derivative showed higher activity than that of (-)-virgatusin.

DOI： 10.1271/bbb.60696

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DOI： 10.1271/bbb.60429

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DOI： 10.1021/np060461j

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Language：English   Publisher：TAYLOR & FRANCIS LTD  

The cytotoxic activity for colon 26 cell line of matairesinol, oxidized matairesinol, 9,9'-epoxylignan and oxidized 9,9'-epoxylignan were examined. (-)Matairesinol (Mat 1) showed greatest cytotoxic activity (LC50 = 9 mu g/ml) of the lactone-type lignans. 7,7'-Oxomatairesinol having same steric configuration as that of (-)-matairesinol showed greater activity (LC50 = 25 mu g/ml) than hydroxy or mono-oxomatairesinol. The activities of 9,9'-epoxylignan and 7,7-oxo-9,9'-epoxylignan having same steric configurations as (-)-matairesinol were weaker than that of corresponding matairesinols. Different activity levels were observed between enantiomers.

DOI： 10.1271/bbb.60353

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Language：English   Publisher：LIPPINCOTT WILLIAMS & WILKINS  

Eucheuma serra agglutinin (ESA) is a lectin derived from a marine red alga E. serra and binds specifically to mannose-rich sugar chains. Previous reports have indicated that ESA associates with several cancer cells via sugar chains on cell surfaces and induces apoptotic cell death. In this study, we investigated the effect of ESA on Colon26 mouse colon adenocarcinoma cells both in vitro and in vivo. ESA induced cell death against Colon26 cells in vitro, and the expression of caspase-3 and the translocation of phosphatidylserine in ESA-treated Colon26 cells suggested that this cell death was induced through apoptosis. An intravenous injection of ESA significantly inhibited the growth of Colon26 tumors in BALB/c mice; moreover, DNA fragmentation was detected in tumor cells following ESA treatment. These results indicated that ESA is effective as an anti-cancer drug not only in vitro but also in vivo. The side-effects of ESA were not considered to be serious because the decrease in body weight of the mice injected with it was negligible. These observations suggest that ESA has the potential to be an effective anti-tumor drug.

DOI： 10.1097/01.cad.0000224458.13651.b4

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Language：English   Publisher：TAYLOR & FRANCIS LTD  

Certain edible large jellyfishes belonging to the order Rhizostomeae are consumed in large quantities in China and Japan. The exumbrella part of the edible jellyfish Stomolophus nomurai was cut and soaked in dilute hydrochloric acid solution (pH 3.0) for 12 h, and heated at 121 degrees C for 20 min. The immunostimulation effects of the jellyfish extract were examined. The jellyfish extract enhanced IgM production of human hybridoma HB4C5 cells 34-fold. IgM and IgG production of human peripheral blood lymphocytes (PBL) were also accelerated, 2.8- and 1.4-fold respectively. Moreover, production of interferon (IFN)-gamma and tumor necrosis factor (TNF)-alpha by human PBL was stimulated 100- and 17-fold respectively. Collagenase treatment inactivated the immunostimulation activity of the jellyfish extract. In addition, purified collagen from bovine Achilles' tendon accelerated IgM production of hybridoma cells. These facts mean that collagen has an immunostimulation effect, and that the active substance in jellyfish extract is collagen.

DOI： 10.1271/bbb.60076

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Language：English   Publisher：TAYLOR & FRANCIS LTD  

The radical and superoxide scavenging activities of oxidized matairesinols were examined. It could be assumed that the free benzylic position was important for higher radical scavenging activity. The different level of activity was observed between 7'-oxomatairesinol (Mat 2) and 7-oxomatairesinol (Mat 3). The activity of 8-hydroxymatairesinol was lower than that of matairesinol (Mat 1). The superoxide scavenging activity of the oxidized matairesinols was also demonstrated for the first time. It is assumed that the pKa value of phenol in the oxidized matairesinols affected this activity.

DOI： 10.1271/bbb.60096

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Language：Japanese  

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Language：English   Publisher：TAYLOR & FRANCIS INC  

The molecular compositions of the commercial nonionic surfactants Span 80 and Span 85 were analyzed by reversed phase high performance liquid chromatography (HPLC). Both surfactants are mixtures of fatty acid esters, containing monoesters, diesters, triesters, and tetraesters. While diesters dominate in the case of Span 80, Span 85 contains mainly tetraesters. Vesicles were prepared from Span 80 (or Span 85) by a two-step emulsification method that involved homogenization and separation steps in which a portion of the surfactants was removed. The composition of the vesicles was analyzed by HPLC with respect to the different esters present. Although commercial Span 80 and Span 85 differ considerably in their molecular compositions, the ester profiles of the vesicles formed were in both cases rather similar and dominated by diesters. Therefore, the particular vesicle preparation method leads to a molecular selection of mainly those components that are prone to form bilayers.

DOI： 10.1080/01932690600859903

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Language：English   Publisher：ELSEVIER SCIENCE BV  

Fat-free bovine milk fermented by 12 kinds of lactic acid bacteria and yeast enhanced monoclonal antibody production of human hybridoma HB4C5 cells 2.8-fold in serum-free medium. Immunoglobulin production of human peripheral blood lymphocytes (PBL) was also stimulated in vitro. IgM and IgG production of human PBL was accelerated up to 2.8-fold and 5.4-fold, respectively. Interferon-gamma production of human PBL was also accelerated 6.0-fold by 50 mu g/ml of the fermented milk. However, interleukin-4 production of PBL was not affected, and tumor necrosis factor-alpha production was suppressed. The activity was enhanced 2.5-fold by the thermal treatment for 30 min at 65 degrees C and was completely lost by trypsin digestion. The findings suggested that the active substance in the fermented milk was heat stable protein. Gel-filtration and the SDS-PAGE analysis revealed that the molecular weight of the active substance was estimated as 19.0 kDa, which was not detected in fat-free bovine milk before fermentation. N-terminal amino acid sequence of the 19.0 kDa protein was highly homologous to proteose-peptone component 3 (PP3). Since molecular weight of PP3 is 28 kDa, it is suggested that the 19.0 kDa protein is derived from degradation of PP3 during fermentation of fat-free milk. Moreover, PP3 purified from fat-free milk also enhanced IgM production of HB4C5 cells. (c) 2005 Elsevier B.V. All rights reserved.

DOI： 10.1016/j.bbagen.2005.05.008

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The first highly enantioselective syntheses of tetra-substituted tetrahydrofuran lignan, (-)- and (+)-virgatusin, were achieved. Hemiacetal 15 was stereoselectively obtained from Evans's syn-aldol product 8 as a single isomer. This hemiacetal 15 was converted to (-)-virgatusin via hydrogenolysis. (+)-Virgatusin was also synthesized through the same process. The enantiomeric excess of the both enantiomers was determined as more than 99% ee. © The Royal Society of Chemistry 2005.

DOI： 10.1039/b501151e

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Language：Japanese   Publisher：The Phytopathological Society of Japan (PSJ)  

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Language：Japanese   Publisher：The Phytopathological Society of Japan (PSJ)  

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Language：English   Publisher：OXFORD UNIV PRESS  

Cloning and disruption offigal, the gene encoding the G protein a subunit FGA1 in phytopathogenic fungus Fitsarium oxysporum, has been reported previously, and the fgal disruptants showed altered colony morphology, increased heat resistance, reduced conidiation and pathogenicity. To further evaluate the role of G protein signaling in this fungus, cloning of fga2, which encodes the second Galpha protein FGA2, was performed by PCR methods. The deduced primary structure of FGA2 (355 amino acid residues) showed high identity with other Galpha proteins, which belong to class III of fungal Got proteins. Disruption offg(12 led to higher heat resistance, similar to the fgal disruptants, but pathogenicity was completely lost, unlike the fgal disruptants. Alteration of colony morphology and conidiation, which was observed in the fgal disruptants, was not observed in the fga2 disruptants. The figal/fga2 double disruptants showed phenotypic alterations similar to the fgal or fga2 single disruptants, but increase of heat resistance was much more pronounced than in each single disruptant. (C) 2004 Federation of European Microbiological Societies. Published by Elsevier B.V. All rights reserved.

DOI： 10.1016/j.femsle.2004.12.009

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Language：English   Publisher：AMER SOC BIOCHEMISTRY MOLECULAR BIOLOGY INC  

Among the members of the major facilitator superfamily of Saccharomyces cerevisiae, we identified genes involved in the transport into vacuoles of the basic amino acids histidine, lysine, and arginine. ATP-dependent uptake of histidine and lysine by isolated vacuolar membrane vesicles was impaired in YMR088c, a vacuolar basic amino acid transporter 1 (VBA1)-deleted strain, whereas uptake of tyrosine or calcium was little affacted. This defect in histidine and lysine uptake was complemented fully by introducing the VBA1 gene and partially by a gene encoding Vba1p fused with green fluorescent protein, which was determined to localize exclusively to the vacuolar membrane. A defect in the uptake of histidine, lysine, or arginine was also observed in the vacuolar membrane vesicles of mutants YBR293w (VBA2) and YCLO69w (VBA3). These three VBA genes are closely related phylogenetically and constitute a new family of basic amino acid transporters in the yeast vacuole.

DOI： 10.1074/jbc.M412617200

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Language：English   Publisher：OXFORD UNIV PRESS  

Cloning and disruption offigal, the gene encoding the G protein a subunit FGA1 in phytopathogenic fungus Fitsarium oxysporum, has been reported previously, and the fgal disruptants showed altered colony morphology, increased heat resistance, reduced conidiation and pathogenicity. To further evaluate the role of G protein signaling in this fungus, cloning of fga2, which encodes the second Galpha protein FGA2, was performed by PCR methods. The deduced primary structure of FGA2 (355 amino acid residues) showed high identity with other Galpha proteins, which belong to class III of fungal Got proteins. Disruption offg(12 led to higher heat resistance, similar to the fgal disruptants, but pathogenicity was completely lost, unlike the fgal disruptants. Alteration of colony morphology and conidiation, which was observed in the fgal disruptants, was not observed in the fga2 disruptants. The figal/fga2 double disruptants showed phenotypic alterations similar to the fgal or fga2 single disruptants, but increase of heat resistance was much more pronounced than in each single disruptant. (C) 2004 Federation of European Microbiological Societies. Published by Elsevier B.V. All rights reserved.

DOI： 10.1016/j.femsle.2004.12.009

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Other Link： http://search.jamas.or.jp/link/ui/2006284378

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Language：English   Publisher：SPRINGER-VERLAG  

The cloning of fga1, the gene encoding a G protein a subunit, was performed by standard PCR techniques and by screening a Fusarium oxysporum genomic library, using the PCR product as a probe. The full-length open reading frame spanned 1,059 nucleotides and the deduced primary structure of the protein (353 amino acid residues) showed high identity to those of G protein alpha(i) family proteins from other filamentous fungi. Disruption of fga1 had no effect on vegetative growth, but reduced the conidiation and pathogenicity of the fungus. Disruptants also showed a decreased level of intracellular cAMP and increased resistance to heat shock at 45 degreesC. These results suggest that the Galpha subunit encoded by fga1 is involved in a signal transduction pathway in F. oxysporum that controls conidiation, heat resistance and pathogenicity.

DOI： 10.1007/s00294-002-0322-y

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Language：Japanese   Publisher：The Phytopathological Society of Japan (PSJ)  

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Language：Japanese   Publisher：The Phytopathological Society of Japan (PSJ)  

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Language：English   Publisher：SPRINGER-VERLAG  

sti35 is one of the heat-shock genes in Fusarium oxysporum, which is a fungal pathogen for wilt disease in plants. We have isolated a genomic clone of sti35 and used it to create disruption mutations. Disruption of the sti35 coding region resulted in the loss of a 32-kDa protein present in heat-shocked cells. The disruption had no detectable effect on growth and development at various temperatures, nor on the ability to acquire thermotolerance in nutrient medium. But the sti35 disruptants showed increased thermotolerance, relative to the wild-type strain, when incubated in minimal medium after heat treatment.

DOI： 10.1007/s002840010135

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Language：English   Publisher：SOC BIOSCIENCE BIOENGINEERING JAPAN  

Treatment of Fusarium oxysporum with 5-azacytidine, a potent inhibitor of DNA methylation, induced nonpathogenic mutants. Analysis of the protein expression pattern by two-dimensional gel electrophoresis revealed a protein that is present in yeast-form cells of the mutants but absent in those of the wild-type strain. N-terminal amino acid analysis indicated that this protein is identical to a region of a polypeptide encoded by a cDNA clone, sti35, previously identified as a heat shock gene in F. oxysporum. A genomic clone for sti35 was isolated and sequence analysis revealed an intron and two heat shock elements upstream of sti35. The analysis also revealed the presence of a leader sequence composed of 27 amino acid residues, which shares a common amino acid composition with leader sequences of the proteins located in the mitochondrial matrix. Different expression patterns of sti35 in the mutants and wild-type strain were demonstrated.

DOI： 10.1263/jbb.90.302

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Language：Japanese   Publisher：The Phytopathological Society of Japan (PSJ)  

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Language：Japanese   Publisher：The Phytopathological Society of Japan (PSJ)  

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Language：Japanese   Publisher：The Phytopathological Society of Japan (PSJ)  

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Language：Japanese   Publisher：The Phytopathological Society of Japan (PSJ)  

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Language：Japanese   Publisher：The Phytopathological Society of Japan (PSJ)  

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