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The root parasitic weed broomrapes, Phelipanche spp., cause severe damage to agriculture all over the world. They have a special host-dependent lifecycle and their seeds can germinate only when they receive chemical signals released from host roots. Our previous study demonstrated that 2-phenylethyl isothiocyanate is an active germination stimulant for P. ramosa in root exudates of oilseed rape. In the present study, 21 commercially available ITCs were examined for P. ramosa seed germination stimulation, and some important structural features of ITCs for exhibiting P. ramosa seed germination stimulation have been uncovered. Structural optimization of ITC for germination stimulation resulted in ITCs that are highly active to P. ramosa. Interestingly, these ITCs induced germination of P. aegyptiaca but not Orobanche minor or Striga hermonthica. P. aegyptiaca seeds collected from mature plants parasitizing different hosts responded to these ITCs with different levels of sensitivity. ITCs have the potential to be used as inducers of suicidal germination of Phelipanche seeds.

DOI： 10.3390/plants11050606

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In the course of our research on the structure-activity relationship of 5,6-dihydro-2H-pyran-2-one, (S)-6-[(R)-2-hydroxy-6-(4-fluorophenyl)hexyl]-5,6-dihydro-2H-pyran-2-one was found to show 2-3-fold more potent plant growth inhibitory activity against Italian ryegrass shoots (IC50 = 95 µm) and roots (IC50 = 17 µm) than compound bearing unsubstituted phenyl group. The small and electron withdrawing atom at 4-position of the benzene ring caused the higher activity.

DOI： 10.1093/bbb/zbab185

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The effect of the stereochemistry of 9,9′-epoxylignan, 7,9′-epoxylignan, and 7,7′-epoxylignan bearing the 4-hydroxy-3-methoxyphenyl group on their antifungal activity was estimated by employing stereoisomers of these compounds. The results suggest that the (7S,7′R,8R,8′R)-stereoisomers of 7,7′-epoxylignan are the most potent. (-)-Verrucosin (16) had an EC50 value of 89 μM against the Alternaria alternata Japanese pear pathotype, whereas the most effective derivative against the A. alternata Japanese pear pathotype was (7S,7′R,8R,8′R)-3-(trifluoromethyl)-4-hydroxy-3′-fluoro-7,7′-epoxylignan derivative 38, which was found to be ∼124 times more potent (EC50 = 0.72 μM) than natural (-)-verrucosin (16). The presence of both hydroxy and electron-withdrawing groups on the 7-aromatic ring enhanced the activity. Compared with that of butane type structure 42, the activity of 7,7′-epoxylignan structure 38, which is fixed between positions 7 and 7′, was 38 times higher.

DOI： 10.1021/acsagscitech.1c00117

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Strigolactones (SLs) regulate important aspects of plant growth and stress responses. Many diverse types of SL occur in plants, but a complete picture of biosynthesis remains unclear. In Arabidopsis thaliana, we have demonstrated that MAX1, a cytochrome P450 monooxygenase, converts carlactone (CL) into carlactonoic acid (CLA) and that LBO, a 2-oxoglutarate-dependent dioxygenase, can convert methyl carlactonoate (MeCLA) into a metabolite called [MeCLA + 16 Da]. In the present study, feeding experiments with deuterated MeCLAs revealed that [MeCLA + 16 Da] is hydroxymethyl carlactonoate (1'-HO-MeCLA). Importantly, this LBO metabolite was detected in plants. Interestingly, other related compounds, methyl 4-hydroxycarlactonoate (4-HO-MeCLA) and methyl 16-hydroxycarlactonoate (16-HO-MeCLA), were also found to accumulate in lbo mutants. 3-HO-, 4-HO-, and 16-HO-CL were detected in plants, but their expected corresponding metabolites, HO-CLAs, were absent in max1 mutants. These results suggest that HO-CL derivatives may be predominant SLs in Arabidopsis, produced through MAX1 and LBO.

DOI： 10.1002/pld3.219

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Ficifolidione, a natural insecticidal compound isolated from the essential oils of Myetaceae species, is a spiro phloroglucinol with an isobutyl group at the C-4 position. We found that ficifolidione showed cytotoxicity against cancer cells via apoptosis. Replacement of the isobutyl group by n-propyl group did not influence the potency, but the effect of the replacement of this group by a shorter or longer alkyl group on the biological activity remains unknown. In this study, ficifolidione derivatives with alkyl groups such as methyl, n-pentyl, and n-heptyl group-instead of the isobutyl group at the C-4 position-were synthesized to evaluate their cytotoxicity against the human promyelocytic leukaemia cell line HL60 and their insecticidal activity against mosquito larvae. The biological activities of their corresponding 4-epimers were also evaluated. As a result, the conversion of the isobutyl group to another alkyl group did not significantly influence the cytotoxicity or insecticidal activity. In HL60 cells treated with the n-heptyl-ficifolidione derivative, the activation of caspase 3/7 and the early stages of apoptosis were detected by using immunofluorescence and flow cytometric techniques, respectively, suggesting that the cytotoxicity should be induced by apoptosis even though the alkyl group was changed.

DOI： 10.3390/molecules24224081

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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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BACKGROUND: Equol is a metabolite of daidzein that is produced by intestinal microbiota. The oestrogenic activity of equol is stronger than daidzein. Equol-producing bacteria are believed to play an important role in the gut. The rod-shaped and Gram-positive anaerobic equol-producing intestinal bacterium Slackia TM-30 was isolated from healthy human faeces and its effects on urinary phyto-oestrogen, plasma and faecal lipids were assessed in adultmice.
RESULTS: The urinary amounts of equol in urine were significantly higher in mice receiving the equol-producing bacterium TM-30 (BAC) group than in the control (CO) group (P<0.05). However, no significant differences were observed between the urinary amounts of daidzein, dihydrodaidzein, enterodiol, and enterolactone between the BAC and CO groups. No significant differences in the plasma lipids were observed between the two groups. The lipid content (% dry weight) in the faeces sampled on the final day of the experiment tended to be higher in the BAC group than in the CO group (P= 0.07).
CONCLUSION: Administration of equol-producing bacterium TM-30 affected the urinary amounts of phyto-oestrogens and the faecal lipid contents of mice. The equol-producing bacterium TM-30 likely influences the metabolism of phyto-oestrogen via changes in the gastrointestinal environment. (C) 2015 Society of Chemical Industry

DOI： 10.1002/jsfa.7490

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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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The plant growth regulatory activity of furofuran lignan (7,9':7',9-diepoxylignan) was evaluated by employing optically pure synthesized (+)- and (-)-enantiomers. (+)-Sesamin possessing a 3,4-methylenedioxy group on the aromatic rings and 7-aryl structure showed growth promotion activity against lettuce roots (EC50 = 0.50 mM); on the other hand, growth inhibitory activity was observed against lettuce shoots (EC50 = 0.38 mM). Against ryegrass shoots, (-)-sesamolin, which has 3,4-methylenedioxy groups on the aromatic rings and a 7-acetal structure, was effective in showing growth inhibitory activity (EC50 = 0.23 mM). Different activity levels were observed between (+)- and (-)-enantiomers. It was assumed that the 3,4-methylenedioxy group on the aromatic ring was more potent for the plant growth regulatory activity.

DOI： 10.1021/acs.jafc.5b01090

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(-)-Dihydroguaiaretic acid (DGA) and its derivatives having 3-hydroxyphenyl (3-OH-DGA) and variously substituted phenyl groups instead of 3-hydroxy-4-methoxyphenyl groups were synthesized to measure their larvicidal activity against the mosquito Culex pipiens Linnaeus, 1758 (Diptera: Culicidae). Compared with DGA and 3-OH-DGA (LC50 (M), 3.52 x 10(-5) and 4.57 x 10(-5), respectively), (8R,8'R)-lignan-3-ol (3) and its 3-Me (10), 2-OH (12), 3-OH (13), and 2-OMe (15) derivatives showed low potency (ca. 6-8 x 10(-5) M). The 4-Me derivative (11) showed the lowest potency (12.1 x 10(-5) M), and the 2-F derivative (4) showed the highest (2.01 x 10(-5) M). All of the synthesized compounds induced an acute toxic symptom against mosquito larvae, with potency varying with the type and position of the substituents. The 4-F derivative (6), which killed larvae almost completely within 45 min, suppressed the O-2 consumption of the mitochondrial fraction, demonstrating that this compound inhibited mitochondrial O-2 consumption contributing to a respiratory inhibitory activity.

DOI： 10.1021/jf504816a

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DOI： 10.1016/j.bmc.2014.12.058

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Cryptocarya diacetate and each of its stereoisomers were stereoselectively synthesized in 8-16 steps. One of the three chiral carbons was converted from the chiral center of a yeast-reduction product. The other two chiral carbons were constructed by employing stereoselective allylation and syn-and anti-1,3-reductions. The enantiomeric excesses of the synthesized cryptocarya diacetate and its stereoisomers were determined to be more than 99%ee using a chiral column.

DOI： 10.1080/09168451.2014.962476

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DOI： 10.1021/np5006746

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The synthesized 7-aryl derivatives of (7R,7'S,8S,8'S)-(+)-verrucosin were applied to growth inhibitory activity test against ryegrass at 1 mM. 7-(3-Ethoxy-4-hydroxyphenyl) derivative 12 and 7-(2-hydroxyphenyl) derivative 4 showed comparable activity to those of (+)-verrucosin against the root (-95%) and the shoot (-60%), respectively. The growth inhibitory activity test against lettuce using synthesized 7-aryl derivatives of (7S,7'R,8R,8'R) () verrucosin at 1 mM showed that the activities of 7-(3-hydroxyphenyl) derivative 20 and 7-(3-ethoxy-4-hydroxyphenyl) derivative 28 are similar to that of (-)-verrucosin against the root (-95%). Against the shoot, 7-(3-hydroxyphenyl) derivative 20 showed higher activity (-80%) than that of ()-verrucosin (-60%). As the next step, (7S,7'R,8R,8'R)-7-(3-hydroxyphenyl) 7' aryl () verrucosin derivatives, in which the most effective 3-hydroxyphenyl group is employed as 7-aromatic ring, were synthesized for the assay against lettuce. In this experiment, 7'-(2-hydroxyphenyl) derivative 37 and 7'-(3-hydroxyphenyl) derivative 38 showed similar activity to that of derivative 20. The effect of 7- and 7'-aryl structures of 7,7'-epoxylignanes on the plant growth inhibitory activity was clarified. The 7- and 7'-aryl structures were simplified to show comparable activity to or higher activity than that of (-)-verrucosin. The plant growth inhibitory activity of a nutmeg component, (+)-fragransin C3b, was estimated as 80% inhibition at 1 mM against ryegrass roots. (C) 2014 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmcl.2014.09.006

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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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All stereoisomers of 3,3'-dimethoxy-7,7'-epoxylignane-4,4'-diol were synthesized to examine the effect of stereochemistry on their plant growth inhibitory activity using lettuce and Italian ryegrass. The effect of structural modifications such as dehydroxylation, methoxylation and hydroxylation at the 9- and 9'-positions of the lignans on the activity was also studied. Most of the epoxylignanes showed higher plant growth inhibitory potency against ryegrass than against lettuce, and the inhibitory activity varied depending on the configurations of each position of the tetrahydrofuran ring (7-, 7'-, 8-, and 8'-positions of the epoxylignanes). Among the 9,9'-position-modified derivatives, the dehydroxy derivatives showed the highest potency. These results suggested that the plant growth inhibitory activity should be influenced by the structure of the epoxylignanes.

DOI： 10.1021/jf4046396

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All the stereoisomers of butanol type 1,7-seco-2,7 '-cyclolignane were stereoselectively synthesized by employing (S)- and (R)-Evans' auxiliaries to construct the stereochemistry. (+)- and (-)-Kadangustin J and their diastereomers were also prepared. The optical purity of the synthesized butanol type 1,7-seco-2,7 '-cyclolignane was more than 99%ee.

DOI： 10.1080/09168451.2014.877833

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The syntheses of 55 lariciresinol derivatives containing derivatives on the 9-position and an aryl group at both 7- and 7'-positions were successful to examine the effect of structure of (-)-lariciresinol (1) on plant growth regulatory activity. (-)-(7R,8R,8'S)-9-Dehydroxylariciresinol 9 showed activity 2-fold more potent than that of natural (-)-lariciresinol (1) and -95% growth inhibitory activity to negative control against rye grass root at 1 mM. The derivatives bearing hydrophobic and smaller groups at the 9-position showed higher activity. The importance of 4- and 4'-hydroxy groups and 3- and 3'-small hydrophobic groups on 7- and 7'-phenyl groups for higher activity was also suggested.

DOI： 10.1021/jf404292w

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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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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 insecticidal activity of (-)-(8R,8'R)-3,3'-dimethoxy-9,9'-epoxylignane-4,4'-diol (1) against houseflies was clarified for the first time. The activities of other stereoisomers were weaker than that of the (8R,8'R)-stereoisomer. In the course of research into structure activity relationships involving 30 newly synthesized (8R,8'R)-derivatives, 5-fold higher activity (ED50 = 0.91 nmol/fly) was observed for (-)-(8R,8'R)-3,3',4-trimethoicy-9,9'-epoxylignan-4'-ol (21) than for the naturally occurring compound (1). The activity of I was weaker than that of (-)-(8R,8'R)-dihydroguaiaretic acid ((-)-DGA) (4); however, compound 21 showed almost the same level of activity as 4.

DOI： 10.1021/jf400300n

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Effects of various plant phenolics, including polyphenols, on the oxidation of oxymyoglobin were investigated. Most phenolics promoted the oxidation of oxymyoglobin at both pH 5.4 and 7.4. Potent oxidation-promoting activity was observed by several efficient antioxidant polyphenols with a catechol moiety. Therefore, effects of the catechol structure were investigated using dihydrocaffeic acid analogues. The results clarified that ortho- or para-substituted diphenol structures were important for promoting the oxidation of oxymyoglobin. Inhibition of such prooxidant activity for oxymyoglobin by dihydrocaffeic acid was also investigated. Although the required concentration was relatively higher than that of dihydrocaffeic acid, several amino acids inhibited the oxidation. Among these, cysteine was the most potent. Although cysteine alone completely inhibited oxidation at a concentration above I mmol/L, 0.1 mmol/L cysteine showed oxidation-promoting activity. In the presence of 0.1 mmol/L dihydrocaffeic acid, in the range of 0.01 mmol/L to 1 mmol/L cysteine, 0.1 mmol/L cysteine showed the most efficient inhibition. These results suggest the possibility of the formation of some equimolar complexes of dihydrocaffeic acid and cysteine such as 5'-cysteinyl dihydrocaffeic acid, which may be produced during the prooxidation of dihydrocaffeic acid, contributing to the inhibition of the oxidation of oxymyoglobin.

DOI： 10.1021/jf304775x

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DOI： 10.1016/j.bmcl.2012.08.078

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A series of imidacloprid (IMI) derivatives with an alkylated imidazolidine ring were asymmetrically synthesized to evaluate their insecticidal activity against adult female housefly, Musca domestica, and affinity to the nicotinic acetylcholine receptor of the flies. The bulkier the alkyl group, the lower was the receptor affinity, but the derivatives methylated and ethylated at the R-5-position of the imidazolidine ring were equipotent to the unsubstituted compound. Quantitative structure-activity relationship (QSAR) analysis of the receptor affinity demonstrated that the introduction of a substituent into the imidazolidine ring was fundamentally disadvantageous, but the introduction of a substituent at the R-5-position was permissible in the case of its small size. The binding model of the synthesized derivatives with the receptor supported the QSAR analysis, indicating the existence of space for a short alkyl group around the R-5-position in the ligand-binding site. In addition, positive correlation was observed between the insecticidal activity and receptor affinity, suggesting that the receptor affinity was the primary factor in influencing the insecticidal activity even if the imidazolidine ring was modified. (C) 2012 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.bmc.2012.09.007

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DOI： 10.1039/c1fo10166h

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Language：English   Publisher：Japan Society for Bioscience, Biotechnology, and Agrochemistry  

Four imidacloprid derivatives with an asymmetrically methylated imidazolidine ring were synthesized. Their affinity to the nicotinic acetylcholine receptor of housefly <I>Musca domestica</I> and insecticidal activity against the housefly were measured. The compound with a 5<I>R</I>-methylated imidazolidine ring demonstrated intrinsic activity comparable to that of the unsubstituted compound. Most of the compounds were synergized by oxygenase inhibitors.

DOI： 10.1271/bbb.100846

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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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Language：English   Publishing type：Research paper (scientific journal)   Publisher：Japan Society for Bioscience, Biotechnology, and Agrochemistry  

Matairesinol is one of the lignan compounds found in a variety of plant foodstuffs. We investigated the immunomodulatory effects of (−)-matairesinol <I>in vivo</I> and <I>ex vivo</I> 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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Language：English   Publishing type：Research paper (scientific journal)   Publisher：ELSEVIER SCI LTD  

The chain-breaking antioxidation reaction mechanism of a phenolic lignan in a lipid oxidation system was investigated. The 2,2&apos;-azobis(isobutyronitrile) (AIBN)-induced radical oxidation reaction in a large amount of ethyl linoleate in the presence of secoisolariciresinol, one of the potent antioxidative lignans widely distributed in edible plants, produced two types of peroxides as radical termination products, as well as a cyclic derivative. The isolation and structure determination of the peroxides revealed that they have a peroxide linkage with ethyl linoleate or isobutyronitrile at the 1-position of the benzene ring of secoisolariciresinol. The cyclic derivative was also identified as lariciresinol by spectroscopic analysis. Based on the chemical structures of these products, a reaction pathway for the antioxidation reaction of secoisolariciresinol in oxidising lipid media was proposed. (C) 2010 Elsevier Ltd. All rights reserved.

DOI： 10.1016/j.foodchem.2010.04.065

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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   Publishing type：Research paper (international conference proceedings)  

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The first diastereoselective construction of butane-type and butyrolactone-type secocyclolignanes was achieved by the application of a high-valency heterobimetallic Ir-Sn complex to benzyl alcohols prepared from an Evans's anti-aldol product. The elimination of an acetoxymethyl group to give a cinnamyl structure by using a high-valency heterobimetallic Ir-Sn complex was also observed in this study.

DOI： 10.1271/bbb.90401

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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 inhibitory effect of (-)-, (+)-matairesinol and (-)-, (+)-secoisolariciresinol on the discoloration of dark muscle (chiai in Japanese) of two-year-old yellow-tail (hamachi in Japanese) was evaluated by measuring the X and a* values. (-)-Matairesinol was most effective for retaining the red color of dark muscle in this experiment.

DOI： 10.1271/bbb.80830

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

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

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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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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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：English   Publishing type：Research paper (scientific journal)   Publisher：Japan Society for Bioscience, Biotechnology, and Agrochemistry  

The relationship between the antibacterial activity and structure of 9-<I>O</I>,9′-<I>O</I>-demethyl (+)-virgatusin (<B>Virg 3</B>) 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 4′-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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Language：English   Publishing type：Research paper (scientific journal)   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   Publishing type：Research paper (scientific journal)   Publisher：AMER CHEMICAL SOC  

The optically pure trisubstituted 7'-oxotetrahydrofuran lignans (-)- and (+)-magnolone (1) were synthesized by employing stereoselective S(N)1 intramolecular cyclization as a key reaction. The absolute configuration of naturally occurring (-)- magnolone was determined as (7S,8R,8'S).

DOI： 10.1021/np070300v

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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 &gt;&gt; 99%.

DOI： 10.1271/bbb.70236

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

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.

DOI： 10.1021/np060461j

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Tetrahydrofuran aminolignans bearing an amino group at the 8 position were synthesized via an N,O-heterocyclic compound that had been obtained by silylnitronate cycloaddition.

DOI： 10.1271/bbb.60575

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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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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   Publishing type：Research paper (scientific journal)   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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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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A glandular secretion of the civet cat, (2S,6S)-(6methyltetrahydropyran-2-yl)acetic acid 1 and its enantiomer, were synthesized from the Yeast-reduction product and recovered substrate from yeast reduction.

DOI： 10.1271/bbb.70.712

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

It has been clarified in the present investigation that a high degree of oxidation at the benzylic position of phenolic lignans bearing a 4-hydroxy-3-methoxybenzyl group reduces their antioxidant activity and that the antioxidant activity of the bis(4-hydroxy-3-methoxybenzyl)tetrahydrofuran lignan 2 is higher than that of the corresponding gamma-butyrolactone lignan 1. This was demonstrated by comparing the antioxidant activities of compounds 1 and 2 with those of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4, the bis(hydroxybenzyl)tetrahydrofurans 7 and 8, the (benzoyl)(benzyl)tetrahydrofuran 6, and the dibenzoyltetrahydrofuran 9. The activity level of compound 2 was approximately the same potency as that of the tetrahydronaphthalene-tetrahydrofuran 5. These compounds possess either a 4-hydroxy3-methoxybenzyl group or a 4-hydroxy-3-methoxybenzoyl group as the benzyl or benzoyl group. An examination of radical scavenging activity showed differences of activity between diastereomers. To make this comparison possible, compounds 1-9 were synthesized using new synthetic routes for several of these lignans. In this investigation, stereoisomers of the (benzyl)(hydroxybenzyl)tetrahydrofurans 3 and 4 and liovils 7 and 8 were synthesized for the first time.

DOI： 10.1021/np050089s

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Optically pure (S)- and (R)-vinylpiperidine 2 and (S)-and (R)-(hydroxyethyl)piperidine 3, which were key intermediates for the synthesis of aloperine, were synthesized from yeast-reductive products.

DOI： 10.1271/bbb.69.1589

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

Olivil-type lignans, an enantiomeric type of natural olivil, were synthesized for the first time to evaluate the relationship between the structure of olivil and its antioxidant activity. A comparison of the antioxidant activity with that of other synthesized tetrahydrofuran lignans indicated reduced activity with the tertiary hydroxy group. A different effect of the two phenolic groups of olivil on the antioxidant activity was also observed.

DOI： 10.1271/bbb.69.113

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(+) and (-)-Dihydropinidine and (+)- and (-)-epidihydropinidine were synthesized from hydroxy esters 1 and 2 which had been prepared by yeast reduction of methyl (2-oxocyclohexyl)acetate. The enantiomeric excess at the C-1 positions of 1 and 2 were both determined as more than 99% ee.

DOI： 10.1271/bbb.68.676

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Nine furofuran compounds having a different type of oxidation were synthesized from one common intermediate in a short series of steps, and the antioxidant activity was evaluated. It was found that the tertiary hydroxy group on the furofuran ring affected the degree of antioxidant activity and that the structure, except for the phenolic part, was important for the antioxidant activity.

DOI： 10.1271/bbb.68.183

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(R) and (S)-Aldehydes 2, which are intermediates for the synthesis of (5R) and (5S)-HETE, were respectively synthesized from the yeast-mediated reductive products, hydroxy ester 3 and cis-lactone 4, through Baeyer-Villiger oxidation with complete retention of enantiomeric excess.

DOI： 10.1271/bbb.67.1959

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The 4-oxofurofuran lignan, (+)-aptosimon (1), was synthesized from gamma-butyrolactone (9). To construct the two benzylic chiral center of (+)-aptosimon (1), highly erythro selective aldol condensation and stereoconvergent SN1 intramolecular cyclization were used as the key reactions.

DOI： 10.1271/bbb.67.838

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

Morinol C and morinol D are neolignans isolated from the Chinese medicinal herb Morina chinensis as racemates. (1R,2R)-Morinol C and (1S,2R)-morinol D were synthesized from (+)-(3R,4R)-4-(3,4-dimethoxyphenyl)-3-pivaloyloxymethyl-4-butanolide 4. On the other hand, (1S,2S)-morinol C and (1R,2S)-morinol D were synthesized from anti-aldol product 8.

DOI： 10.1039/b211801g

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(1S,2S,5R,6S)-6-(3,4-Methylenedioxyphenyl)-3,7dioxabicyclo[3.3.0]octan-1,2-diol ((+)-1-hydroxysamin 1) was synthesized, starting from olefin 8. Stereoselective alpha-hydroxylation was achieved after converting 8 to aldehyde 13. Resulting unstable alpha-hydroxy aldehyde 14 was then transformed to (+)-1-hydroxysamin (1). This is a new efficient synthetic route to 1,2-oxygenated 6-arylfurofuran lignans.

DOI： 10.1271/bbb.66.1495

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

Novel yeast reduction which gave (1R, 2S)-hydroxy ester 10 and (1S, 5S)-lactone 11 from racemic ketoester 12 was discovered. After 10 and 11 were converted to lactone 15 and 17, enantiomeric excesses were determined as 99% and 95%, respectively. This novel yeast reduction was applied to synthetic study of metabolites of 5-oxo-ETE 1. (R)-6,7-Dihydro- 5-HETE lactone 5 and (S)-6,7-dihydro-5-HETE lactone 6 were synthesized from 15 and 17, respectively.

DOI： 10.1039/b206843p

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

A 2,3,4-tri-substituted tetrahydrofuran-type lignan, (+)-dihydrosesamin 2, was stereoselectively synthesized by using erythro-selective aldol condensation of the potassium enolate from (3R)-3-(3,4-methylenedioxyphenyl)-4-butanolide 3 with piperonal as a key reaction. This is the first stereoselective synthesis of (+)-dihydrosesamin, which is the enantiomer of the natural product.

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As a model synthesis on cis-2,3-dibenzyl-4-butanolide lignan, cis-(2S,3R)-parabenzlactone bearing a chiral benzyl alcohol moiety was stereoselectively synthesized from L-arabinose.

DOI： 10.1271/bbb.65.1669

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(+)-Magnostellin C, which is a tetrahydrofuran type of lignan bearing a chiral secondary benzylic hydroxy group, was stereoselectively synthesized from L-arabinose by using threo selective aldol condensation.

DOI： 10.1271/bbb.65.1559

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The three-selective aldol condensation of (3R, 4S)-3-hydroxy-5-trityloxy-4-pentanolide, which was prepared from L-arabinose, with piperonal was applied to the stereoselective synthesis of the olivil type of lignan, (2R, 3R, 4R)-4-benzyl-4-hydroxy-3-hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran.

DOI： 10.1271/bbb.64.2320

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(3R)-3-[(1R)-1-(tert-Butyldimethylsilyl)oxy-1-(2-methoxy-4,5- methylenedioxyphenyl) methyl]-2-methylene-4-butanolide, which is a key intermediate for the synthesis of 1,2-oxidized furofuran lignan, was stereoselectively synthesized from L-glutamic acid by applying direct methylenation to butanolide.

DOI： 10.1271/bbb.64.2209

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The olivil type of lignan, (2S,3R,4R)-4-benzyI-4-hydroxy-3- hydroxymethyl-2-(3,4-methylenedioxyphenyl)tetrahydrofuran, was stereoselectively synthesized from D-xylose.

DOI： 10.1271/bbb.64.1563

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The optically active samin type of lignan, (1R,2S,5R, 6S)-6-(2-methoxy-4,5-methylenedioxyphenyl)-3,7-dioxabicyclo[3.3.0]octan-2-ol, was stereoselectively synthesized from L-glutamic acid via (2R,3R)-2-[(1S and R)-1-[( tert - butyldimethylsilyl)oxy] - 1 - (2 - methoxy - 4,5-methylenedioxyphenyl)methyl] -3-[(tert - butyldiphenylsilyl)oxy]methyl-1,4-butanediol.

DOI： 10.1271/bbb.64.878

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The synthesis of methyl (S)-( -)-6,8-dihydroxyoctanoate as a precursor of (R)-(+)-alpha-lipoic acid was accomplished by using methyl (S)-(-)-(2-oxocyclohexyl)acetate, which had been obtained from baker's yeast reduction, as a chiral starting material.

DOI： 10.1271/bbb.63.2025

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(4R)-[(1S)-1-[(tert-Butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]-3-methylenedihydro-2(3H)-furanone and (4R)-[(1R)-1-[(tert-butyldimethylsilyl)oxy]-1-(2-methoxy-4,5-methylenedioxyphenyl)methyl]3-methylenedihydro-2(3H)-furanone, which are key intermediates for the synthesis of 1,2-oxidized furofuran lignan, were each stereoselectively synthesized from L-glutamic acid.

DOI： 10.1271/bbb.63.1605

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(-)-Podorhizol (1) was stereoselectively synthesized by erythro preferential aldol condensation of 3,4,5-trimethoxybenzaldehyde with potassium enolate from (+)-(R)-3-(3,4-methylene dioxybenzyl)-4-butanolide (2) (erythro: threo = 85:15). Erythro selectivity was observed in the aldol condensation of many alkoxybenzaldehydes with potassium enolate from(+)-gamma-butyrolactone 2. However, benzaldehydes having methoxy groups at both the 2 and 6 positions gave three selectivity in the aldol condensation with potassium enolate from (+)-gamma-butyrolactone 2.

DOI： 10.1271/bbb.63.1453

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

As a model experiment for the stereoselective synthesis of optically active cis-alpha beta-dibenzyl-alpha-hydroxy-gamma-butyrolactone, (2R, 3S)-2-benzyl-2-hydroxy-3-(3,4-methylenedioxybenzyl)-gamma-butyrolactone (3) was stereoselectively synthesized from L-(+)-arabinose.

DOI： 10.1271/bbb.62.1726

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Stereoselectivity in the Michael addition of (Me2C=CH)(2)CuMgBr and (Me2C=CH)(2)CuLi to 3-alkyl/H-4-[(tert-butoxycarbonyl)alkyl]-2-cyclohexenone was studied. (Me2C=CH)(2)CuMgBr showed stereoselectivity in all eases (3-H, Me: anti; 3-n-Bu: syn), This stereoselectivity disappeared in the reaction of (Me2C=CH)(2)CuLi with 4-[(tert-butoxycarbonyl)methyl]-3-butyl-2-cyclohexenone However, the stereoselectivity was recovered by elongating the 4-alkyl chain of 2-cyclohexenone to show the same selectivity as that of (Me2C=CH)(2)CuMgBr.

DOI： 10.1271/bbb.62.764

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As a model experiment for the synthesis of optically active alpha,beta-dibenzyl-alpha-hydroxy-gamma-butyrolactone (1), (2S,3S)-2-benzyl-2-hydroxy-3-(3 ,4-methylenedioxybenzyl)-gamma-butyrolactone (3) was stereoselectively synthesized from L-(+)-arabinose via the carissanol-type of lignan, (2R/S,3S,4S)-3-benzyl-2,3-dihydroxy-4-(3,4-methylenedioxybenzyl)tetrahydrofuran (4).

DOI： 10.1271/bbb.62.521

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Baker's yeast reduction of methyl and ethyl (2-oxocyclohexyl)acetates proceeded with enantio-and diastereo-selectivity, affording the corresponding (2S)-trans-alcohols (major), (2S)-cis-alcohols (minor), and the unaltered (1S)-ketones with high optical purity.

DOI： 10.1271/bbb.62.181

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As a model for the synthesis of optically active 6-aryl-2-aryloxy-1-hydroxy-3,7-dioxabicyclo-[3.3.0]octanes, which are 1,2-dioxygenated furofuran lignans, the most important intermediate, (+)-(1S,2S,5R,6S)-1-hydroxysamin(1), was synthesized from L-(+)-arabinose.

DOI： 10.1271/bbb.61.1342

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(+)-Abscisyl beta-D-glucopyranoside was isolated from mature Citrus unshu peelings as a germination inhibitor component. This is the first report of the direct isolation of (+)-abscisyl beta-D-glucopyranoside from this source.

DOI： 10.1271/bbb.59.1968

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Two haedoxan-analogs, (+/-)-(1S*,2R*,5R*,6S*)-2-(2,6-dimethoxyphenoxy)-1-hydroxy-6-[(+/-)-(2S*,3R*)-7/6-methoxy-3/2-methoxymethyl-2/3-(3,4-methylenedioxyphenyl)-3,4-dihydro-2H-chromen-6/7-yl]-3,7-dioxabicyclo[3.3.0]octanes, were synthesized. They both had chromanyl groups instead of the (2R,3R)-6-methoxy-2-methoxymethyl-3-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl group of the haedoxan molecule. In the synthesis, a (+/-)-(1S*,2R*,5R*,6R*)-isomer was obtained. An assay of these chromans indicated that the 1-oxygen atom of the 1,4-benzodioxane ring of haedoxans significantly contributed to their insecticidal activity.

DOI： 10.1271/bbb.57.884

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

Five analogs of the insecticidal lignan of the Phryma were synthesized by modifying its 3,4-methylenedioxyphenyl group with a phenyl, 4-methoxyphenyl, 3-methoxyphenyl, 3,4-dimethoxyphenyl, or 4-chlorophenyl group to evaluate the contribution of the methylenedioxy function to the activity. The assay results revealed that the 4-oxymethylene part of the 3,4-methylenedioxyphenyl group collaborated more for strengthening the insecticidal activity than the 3-oxymethylene part did. Unexpectedly, the 3,4-dimethoxyphenyl analog was totally inactive, even at a high dose level.

DOI： 10.1271/bbb.56.1760

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The methoxymethyl group of the 6-methoxy-2-methoxymethyl-3-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl moiety of insecticidal lignans of Phryma was modified with several alkyl groups to evaluate the effect on activity of the substituents. The assay results make it evident that this activity was significantly modified by the chain length or bulkiness of the alkyl groups and that the oxygen atom of the methoxymethyl group was fairly important for enhancing the activity.

DOI： 10.1271/bbb.56.1751

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The influence on the insecticidal activity of haedoxan A of its 3-(3,4-methylenedioxyphenyl) group in the 1,4-benzodioxanyl moiety was examined with two (+/-)-(1S*,2R*,5R*,6S*)-6-[(2R*,3R*)-3-alkyl-6-methoxy-2-methoxymethyl-1,4-benzodioxan-7-yl]-2-(2,6-dimethoxyphenoxy)-1-hydroxy-3,7-dioxabicyclo-[3.3.0]octanes. Replacement of the methylenedioxyphenyl group of haedoxan by methyl and n-butyl group resulted in a large decrease in the activity, indicating the importance of the 3-aryl group for the potent insecticidal activity of haedoxan.

DOI： 10.1271/bbb.56.1744

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The haedoxan analog, (+/-)-2-(2,6-dimethoxyphenoxy)-1-hydroxy-6-(6-methoxy-1,4-benzodioxan-7-yl)3,7,-dioxabicyclo[3.3.0]octane, and its congeners with 2-alkoxymethyl, 2-hydroxymethyl, 2-chloromethyl and 3-(3,4-methylenedioxyphenyl) substituents on the 1,4-benzodioxanyl group were synthesized from 6-methoxy-1,4-benzodioxan-7-carbaldehyde and its (+/-)-2- and 3-substituted derivatives, respectively. Some analogs were considerably insecticidal, although much less active than natural haedoxan A. The assay results suggest that 2,3-disubstitution on the 1,4-benzodioxanyl group was necessary to intensify the insecticidal activity.

DOI： 10.1271/bbb.56.1193

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Five 2-substituted 6/7-methoxy-1,4-benzodioxan-7/6-carbaldehydes and 6-methoxy-1,4-benzodioxan-7-carbaldehyde available for the syntheses of insecticidal neolignan analogs were prepared from 4/3-benzyloxy-3/4-hydroxybenzaldehydes and 1,4-benzodioxan-6-carbaldehyde, respectively.

DOI： 10.1271/bbb.56.630

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Ten haedoxan analogs with the bond split between 2C and 3C of the 6-methoxy-2-methoxymethyl-3-(3,4-methylenedioxy)phenyl-1,4-benzodioxan-7-yl group of haedoxans were synthesized, and their insecticidal activity was assessed on the housefly. The inactivity of an analog having a 2-methoxy-5-(2-methoxyethoxy)-4-(3,4-methylenedioxybenzyloxy)phenyl instead of the 1,4-benzodioxan-7-yl group made it evident that the benzodioxane framework is essential for the activity of haedoxans.

DOI： 10.1271/bbb.56.418

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The influence of the 6-methoxy-2-methoxymethyl-3-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl group on the insecticidal activity of haedoxans was studied by synthesizing an analog without the (methoxymethyl)methinoxy moiety of the benzodioxanyl group to test for its activity on the housefly. The inactivity of the analog and its satellite compounds implies that the (methoxymethyl)methinoxy moiety is essential for the biological activity of haedoxans.

DOI： 10.1271/bbb.56.412

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Language：English   Publishing type：Research paper (scientific journal)   Publisher：JAPAN SOC BIOSCI BIOTECHN AGROCHEM  

Several analogs modifying the 6-methoxy-2-methoxymethyl-3-(3,4-methylenedioxyphenyl)-1,4-benzodioxan-7-yl group of haedoxans were synthesized and their insecticidal activity was examined. 2-(2,6-Dimethoxyphenoxy)-1-hydroxy-6-(2-methoxy-5-methoxyethoxyphenyl)-3,7-dioxabicyclo-[3.3.0]octane, which lacked the 3-(3,4-methylenedioxybenzyloxy) moiety of the benzodioxanyl group, was not insecticidal, but caused prolonged paralysis of the housefly. A compound replacing the 6-(2-methoxy-5-methoxyethoxyphenyl) by 6-(5-butoxy-2-methoxyphenyl) exhibited insecticidal activity comparable to one thirty-thousandth of that of haedosan A. It became evident that the 1,4-benzodioxane framework charging the 3-(3,4-methylenedioxy)phenyl group is important for the insecticidal activity of haedoxans.

DOI： 10.1271/bbb1961.55.3075

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

The analytical and insecticidal assays with the extract of the herbaceous perennial plant, Phryma leptostachya L., have been conducted, including the isolation, structure elucidation and total syntheses of the active plant components, as well as derivation of congeners and analysis of structural requirements for the biological activity. So far, novel insecticidal sesquilignans such as HAEDOXAN A, C-acetate, D, F-acetate, G-acetate, and H-acetate, of which content totally below 5% of the extract, were revealed to be responsible for the peculiar flaccid paralysis followed by the insect death. In association with piperonyl butoxide, haedoxan A showed very high insecticidal activity against housefly as comparable with deltamethrin. The synthetic studies clarified the activity is tightly linked with the absolute configuration (1S, 2R, 5R, 6S, 2"R, 3"R) among the 32 stereoisomers. The molecule could take a conformation as the opened 15-crown-5, suggesting the ability to chelate with metal ions such as Ca^<+2>, Mg^<+2>, and Na^<+1> in the nervous system of insects. The discussions will be focused on the total synthesis and absolute configuration of (+)-haedoxan D as well as the structure-activity relationship concerning with about 50 congeners of haedoxan obtained by the isolation and syntheses. The previous assignment of the absolute configuration of (1S, 2S, 5R, 6S)-(+)-phrymarolin I and (1S, 2S, 5R, 6S,2"R,3"R)-(+)-haedoxan D, depending on the large acetylation shift of 2-H in their molecules, have been revised to (1S, 2R, 5R, 6S) and (1S, 2R, 5R, 6S, 2"R, 3"R), respectively, based on their NOESY spectra.

DOI： 10.24496/tennenyuki.30.0_1

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Language：English   Publishing type：Research paper, summary (international conference)   Publisher：AMER CHEMICAL SOC  

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Language：Japanese   Publisher：Pesticide Science Society of Japan  

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Language：English   Publisher：Japan Society for Bioscience, Biotechnology, and Agrochemistry  

Optically pure (+)- and (-)-boronolides were stereoselectively synthesized from yeast reductive products which had been obtained by yeast reduction of one common racemic substrate. The lactone structure of boronolide was constructed by Baeyer-Villiger oxidation. The stereochemistry of the yeast reduction products was studied to obtain the stereocenters at 5 positions of the dodecanolides of (+)- and (-)-boronolides. The stereochemistry of the 6 and 7 positions was obtained by AD-mix-α or β oxidation. The chiral center at the 8 position was constructed by employing (R)-(+)- or (S)-(-)-2-methyl-CBS- oxazaborolidine reduction or the Mitsunobu reaction. The plant growth-inhibitory activity against Echinochloa crusgalli L. of naturally occurring (+)-boronolide was higher than that of the (-)-boronolide.

DOI： 10.1271/bbb.120317

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Language：Japanese   Publisher：Pesticide Science Society of Japan  

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Language：Japanese   Publisher：Pesticide Science Society of Japan  

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All stereoisomers of lariciresinol were synthesized to examine the effect of stereochemistry on plant growth. Configuration of benzylic 7-positions was constructed through S N 1 or S N 2 intramolecular etherification. 8- and 8′-position configurations were established from the starting material except for all cis stereoisomers, the 8-position configurations of which were achieved by employing stereoselective hydroboration. (-)-Lariciresinol and its 7S,8S,8′R stereoisomer inhibited the root growth of Italian ryegrass to 51-55% relative to the negative control, whereas other stereoisomers had less effect. These results demonstrate that the stereochemistry of lignans is one of the important factors influencing their inhibitory activity. © 2011 American Chemical Society.

DOI： 10.1021/jf203222w

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Language：English   Publisher：Japan Society for Bioscience, Biotechnology, and Agrochemistry  

The larvicidal activity against Culex pipiens of all stereoisomers of dihydroguaiaretic acid (DGA) and secoisolariciresinol was measured, and these DGAs were found to be potent. Sixteen (-)-DGA derivatives were then newly synthesized to analyze their structureactivity relationship. Two derivatives monohydroxylated at the 3- or 4-position of the 7-phenyl group of DGA induced acute paralytic activity in the mosquitoes. Derivatives with several hydroxyl groups had lower activity than the natural compound, suggesting that hydrophobicity was probably an important factor for their insecticidal activity.

DOI： 10.1271/bbb.110269

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Language：English   Publisher：Japan Society for Bioscience, Biotechnology, and Agrochemistry  

The antioxidative activity of secocyclolignanes was compared with that of the corresponding dibenzyl lignans for the first time. The radical scavenging activity of the secocyclolignanes was weaker than that of the corresponding dibenzyl lignans, the butane diol type showing the highest activity. The butane type of secocyclolignane exhibited the highest antioxidant activity of the unsaturated fatty acid.

DOI： 10.1271/bbb.100912

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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：Japanese   Publisher：Pesticide Science Society of Japan  

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Language：English   Publisher：TAYLOR & FRANCIS LTD  

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