Journal
JOURNAL OF NATURAL PRODUCTS
Volume 72, Issue 3, Pages 433-437Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np8006952
Keywords
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Funding
- NIH [P50AT00155]
- National Center for Complementary and Alternative Medicine (NCCAM)
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As an extension of work on the recently discovered nitrogenous metabolites from Cimicifuga/Actaea species, three new guanidine alkaloids have been isolated and characterized from C. racemosa (syn. A. racemosa) roots. Of these, cyclo-cimipronidine (1) and cimipronidine methyl ester (2) are congeners of cimipronidine (3), whereas dopargine (5) is a derivative of dopamine. By employing NMR- and MS-guided chemodiversity profiling of a polar serotonergic (5-HT gamma) fraction, the guanidine alkaloids were initially detected in a clinical extract of black cohosh and were isolated along with a congener of salsolinol 4, 5, and 3-hydroxytyrosol 3-O-glucoside (7). The structures of 1, 2, and 5 were confirmed by 1D and 2D NMR spectroscopy as well as LC-MS and HRMS spectroscopy. A plausible biosynthetic relationship may be inferred between the homoproline-analogue cimipronidines and the dopamine-derived Cimicifuga alkaloids. These strongly basic and frequently zwitterionic nitrogenous metabolites contribute considerable chemical diversity to the polar serotonergic fraction of black cohosh.
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