Structure-activity relationships of new phytotoxic metabolites with the botryane skeleton from Botrytis cinerea.

The fungal antibiotic botrydial (1) and related compounds constitute an imp ortant group of metabolites whose biological activity was not previously kn own in depth. The isolation, in addition to known compounds, of three new e pimer metabolites with the botryane structure has allowed us to study the s tructure-activity relationships. The results suggest that, in addition to t he presence of the dialdehyde functionality, the antibiotic, phytotoxic and cytostatic activities shown by some of these compounds are strongly correl ated with the stereochemistry of the C-1/C-8 dialdehyde moieties. The relat ive configuration (S) of the C-l substituent seems to play a critical role in the binding of the substrate to the chemoreceptor. (C) 1999 Elsevier Sci ence Ltd. All rights reserved.