Phytochemistry 2000-09-01

Transformation of jervine by Cunninghamella elegans ATCC 9245.

K A El Sayed, A F Halim, A M Zaghloul, D C Dunbar, J D McChesney, Khalid A El Sayed, Ahmed F Halim, Ahmed M Zaghloul, D.Chuck Dunbar, James D McChesney

Index: Phytochemistry 55(1) , 19-22, (2000)

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Abstract

Preparative-scale fermentation of the known C-nor-D-homosteroidal jerveratrum alkaloid jervine with Cunninghamella elegans (ATCC 9245) has resulted in the isolation of (-)-jervinone as the major metabolite. In addition, C. elegans ATCC 9245 was able to epimerize C-3 of jervine, producing 3-epi-jervine. This epimerization reaction was similar to that reported for tomatidine, the known spirosolane-type Solanum alkaloid. The structure elucidation of both metabolites was based primarily on 1D- and 2D-NMR analyses.