Co-Authors:
Glotter, E., Faculty of Agriculture, Hebrew University of Jerusalem, Rehovot, Israel
Abraham, A., Agricultural Research Organization, Volcani Center, Bet Dagon, Israel
Günzberg, G., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, Israel
Kirson, I., Department of Organic Chemistry, Weizmann Institute of Science, Rehovot, Israel
Abstract:
Four related steroidal lactones of the withanolide group possessing a 17α-oriented side chain have been characterised as (17S,20S,22R)-5β, 6β-epoxy-14α,17,20-trihydroxy-1-oxowitha-2,24-dienolide [withanolide E (1)], (17S,20S,22R)-14α,17,20-trihydroxy-1-oxowitha-2,5,24-trienolide [withanolide F (2)], (17S,20S,22R)-5α,6β,-14α,17,20- pentahydroxy-1-oxowitha-2,24-dienolide [withanolide S (3)], and (17R,20R,22R)-14α,17-dihydroxy-1-oxowitha-2,5,24-trienolide [withanolide P (4)]. The structure of withanolide E deduced here has been confirmed by X-ray analysis (reported elsewhere); those of withanolide F and S are related to that of withanolide E on the basis of common degradation products. The identification of withanolide P is based on spectral analysis.