Cimipronidine, a cyclic guanidine alkaloid from Cimicifuga racemosa |
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Authors: | Fabricant Daniel S Nikolic Dejan Lankin David C Chen Shao-Nong Jaki Birgit U Krunic Aleksej van Breemen Richard B Fong Harry H S Farnsworth Norman R Pauli Guido F |
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Institution: | Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, USA. |
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Abstract: | A new cyclic guanidine alkaloid, cimipronidine (1), together with the known compound fukinolic acid (2), was isolated from the n-BuOH-soluble fraction of Cimicifuga racemosa roots that showed 5-HT7 receptor binding activity. Structure elucidation of 1, a minor constituent, presented unique challenges based on its polarity, but was accomplished with the use of a combination of one- and two-dimensional NMR as well as MS analyses. The relative configuration was established by analyzing the H,H-coupling constants and the results of the 2-D gradient NOESY spectrum. The previously reported serotonergic (5-HT7), highly polar, n-BuOH-soluble fraction was characterized by HPLC-ELSD and was shown to be a mixture containing the following compounds: cimicifugic acids A, B, and F, fukinolic acid, ferulic acid, isoferulic acid, and compound 1, potentially significant as a marker compound of C. racemosa. |
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