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The Preparation and Bioactivities of (-)-Isovelleral

The Preparation and Bioactivities of (-)-Isovelleral

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

Bioorg Med Chem. 1997 Jul;5(7):1363-7.

PMID: 9377096

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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP37841911	Isovelleral		37841-91-1	Price

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