Biogenetic Conversion of Wyerone and Dihydrowyerone into Wyerone Epoxide in Vicia faba Cotyledons and Screening of Antibacterial Activity

Abstract EN

Background.

Vicia faba is a plant that belongs to the family Fabaceae.

Cotyledons of this plant produce compounds called phytoalexins as a result of fungal and bacterial infection or stress factors.

The phytoalexins are furanoacetylenic compounds.

They include wyerone, wyerol, wyerone acid, their dihydro derivatives, and wyerone epoxide.

These compounds have antimicrobial activities mainly against fungi.

Objective.

The purpose of this study was to elucidate the biogenetic conversion of wyerone and dihydrowyerone to wyerone epoxide in V.

faba and to investigate the antibacterial activities of some of these phytoalexins.

Materials and Methods.

Seeds of Vicia faba were used.

Labelled wyerone and dihydrowyerone were obtained by treating CuCl2-induced cotyledons with sodium (2-14C) acetate and separated by TLC and HPLC.

Labelled wyerone and dihydrowyerone were then applied to induced bean cotyledons to establish any possible interconversion to wyerone epoxide.

Antibacterial activity of wyerone, wyerone acid, and wyerone epoxide was investigated by disc diffusion test against a panel of microorganisms.

Zones of inhibition were reported.

Results.

The radiolabeling studies showed that 12.4% of 14C-wyerone, and 6.01% of 14C-dihydrowyerone were incorporated into wyerone epoxide.

This indicates that wyerone epoxide was most probably derived from wyerone and dihydrowyerone.

In addition, a new compound, 11-hydroxywyerone was isolated for the first time.

Additionally, this study showed that wyerone, wyerone epoxide, and wyerone acid had no antibacterial activity against Gram-negative bacteria but were active against Gram-positive bacteria.