Antimicrobiological Activity of Lignan: Effect of Benzylic Oxygen and Stereochemistry of 2,3-Dibenzyl-4-butanolide and 3,4-Dibenzyltetrahydrofuran Lignans on Activity

Abstract

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.

Antimicrobial Activity of Stereoisomers of Morinols A and B, Tetrahydropyran Sesquineolignans

“…The antibacterial activity of the tetrahydropyran sesquineolignans, morinols A and B and their stereoisomers, was clarified for the first time. In our previous study, the tetra-substituted tetrahydrofuran lignan, 10) di-substituted tetrahydrofuran lignan, and di-substituted -butyrolactone lignan 11) showed antibacterial activity against gram-positive bacteria, but not against gram-negative bacteria. In this study of the tetrahydropyran sesquineolignan, the same result was apparent, showing activity against gram-positive bacteria.…”

“…Since (À)-virgatusin, which is a tetra-substituted tetrahydrofuran lignan, and 3,4-dibenzoyltetrahydrofuran have respectively shown antifungal activity against Colletotrichum lagenarium and Bipolaris oryzae, 9,11) these fungal strains were included for this test. All stereoisomers showed antifungal activity against only Alternaria alternata at 0.5 mM.…”

“…11) Morinols A and B have a unique tetrahydropyran structure. The inhibition of cytokines has been reported by using enantiomeric mixtures, 2) although there is no report on the biological activity of optically pure morinols A and B.…”

IgE-Suppressive Activity of (−)-Matairesinol and Its Structure-Activity Relationship

“…12) All stereoisomers and derivatives were prepared by the previously described method. [7][8][9][10] The enantiomeric excess of all stereoisomers of matairesinol prepared by the previous method was determined as more than 99%ee by using a chiral column. Assay of the IgM productive activity.…”

“…The stereoisomers of matairesinol and derivatives were synthesized by the previously described method. [7][8][9][10] Since IgE is an antibody for allergy, suppressing the activity of IgE-production would decrease the allergic symptoms, while promotive compounds would contribute to research into allergy. The IgM-and IgE-productive activities of secoisolariciresinol, which is a butanediol type of lignan contained in food plant, were examined in our previous study, and the IgM-accelerative production of (À)-and (þ)-secoisolariciresinol was observed; however, none of the stereoisomers of secoisolariciresinol affected the IgE-productive activity.…”