Two new pyridine monoterpene alkaloids by chemical conversion of a commercial extract of harpagophytum procumbens |
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Authors: | Baghdikian Ollivier Faure Debrauwer Rathelot Balansard |
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Institution: | Laboratory of Pharmacognosy and Laboratory of Organic Chemistry, Faculty of Pharmacy, 27 Boulevard Jean Moulin, University Aix-Marseille II, 13385 Marseille Cedex 5, France, ESA 6009, University Aix-Marseille III, Avenue Escadrill. |
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Abstract: | The treatment of harpagide (1), harpagoside (2), or 8-O-p-coumaroylharpagide (3), the main iridoids of Harpagophytum procumbens and Harpagophytum zeyheri, with NH3 and HCl led to aucubinine B(4), a pyridine monoterpene alkaloid (PMTA). A similar procedure applied to a commercial extract of H. procumbens yielded 4 and two new PMTAs named beatrine A (5) and beatrine B (6). The structures of these new PMTAs were established using ESIMS and 2D NMR. Their semisynthesis was analyzed in terms of reaction mechanisms. |
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