Flavonoid Biocides: Structure/Activity Relations of Flavonoid Phytoalexin Analogues

Document Type

Article

Publication Date

1989

Department

College of Forest Resources and Environmental Science

Abstract

Two sets of semisynthetic flavonoid phytoalexin analogues were synthesized and their lipophilicity (RM) correlated with their antifungal and antibacterial activity. Two natural phytoalexins, pisatin and maackiain, were also tested under these same conditions, and their RM's determined. The observed structure/activity relationships suggest that these analogues, and the phytoalexins, function primarily as uncouplers of oxidative phosphorylation. The relative acidity and number of hydroxyl groups per molecule appear to be the main factors affecting the antifungal activity of flavonoids. with the bacterium, Streptococcus faecium, there is not the same simple correlation between lipophilicity and antibacterial activity for the two sets of analogues, implying they have different modes of action.

Publisher's Statement

© 1989

Publication Title

Phytochemistry

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