Bioorganic & Medicinal Chemistry 1997-07-01

The preparation and bioactivities of (-)-isovelleral.

M Jonassohn, R Hjertberg, H Anke, K Dekermendjian, A Szallasi, E Thines, R Witt, O Sterner

Index: Bioorg. Med. Chem. 5(7) , 1363-7, (1997)

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Abstract

The resolution of synthetic (+/-)-isovelleral (1), via chromatographic separation of the two diastereomers of the (-)-menthoxyacetic acid diester of the corresponding (+/-)-diol (3), yielded both enantiomers of the bioactive fungal metabolite (+)-isovelleral (1). While the antimicrobial and cytotoxic activities of the two enantiomers are comparable, natural (+)-1 is approximately 10 times more mutagenic towards Ames' tester strain TA98 than (-)-1. The two enantiomers of the cyclopropane ring isomer 2 also possess negligible mutagenicity compared to (+)-1. Both (+)-1 and (-)-1 have the same affinity for the vanilloid receptor, but significant different affinity for the dopamine D1 receptor.