Highly Enantioselective Semisynthesis of (+)/(-)-Gossypol Schiff Base Derivatives from Ground Plant Material.

We have recently developed a one-pot process for simultaneous extraction and chemical modification (SECheM) on , a Mauritanian called locally "Izide". On the basis of this innovative methodology that consisted of using ground plant roots as starting material in gossypol Schiff base semisynthesis, we now report how this concept can be used to access enantiomerically pure Schiff base atropisomer derivatives of gossypol in only two steps. This study has been envisioned since enantiomerically pure Schiff base atropisomer derivatives of gossypol are generally more potent biologically when compared to racemic gossypol Schiff bases.

Development of SECheM Concept for Isolation and Chemical Modification of Gossypol Directly from Cienfuegosia digitata.

Introduction: Gossypol is an axially chiral natural polyphenol classically extracted from the Malavaceae family. Nevertheless, its extraction and isolation from a plant can be quite complicated and extremely time-consuming since gossypol is known to be sensitive to degradation under solvents, high temperature and light action. Moreover, its purification over column chromatography is a challenging problem due to its ability to oxidise and the existence of various tautomer forms.