Co-Authors:
Kirson, I., Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot, Israel
Abraham, A., Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot, Israel
Lavie, D., Department of Organic Chemistry, The Weizmann Institute of Science, Rehovot, Israel
Abstract:
Reciprocal crossbreeding between Withania somnifera chemotype III (Israel) and chemotype Indian I (Delhi) were performed. The F1 offspring of this cross was characterized by significant changes in the main steroidal lactone constituents of the parent plants. From the withaferin A (9) and the withanone (2) both present as major constituents in the parent Indian I, the former had disappeared in the hybrid and was replaced by withanolide D (10), whereas the latter was still present, though in about one third of the original quantity. It was accompanied by 17‐deoxy‐20‐hydroxy withanone (2) and by withanolide T (1); the enzymatic system leading to hydroxylation at C20 (20αF‐OH) has a dominant character. Two new withanolides have been isolated from this F1 offspring, namely withanolide T (1) (20αF‐hydroxy withanone) and withanolide U (5) (4β‐hydroxy‐withanolide G). The structures assigned to these two new compounds are based on spectral evidence (NMR, IR and UV) and analysis of their fragmentation under electron impact. Copyright © 1977 WILEY‐VCH Verlag GmbH & Co. KGaA, Weinheim