title: Cimipronidine, a cyclic guanidine alkaloid from Cimicifuga racemosa.
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.
authors.affiliation: Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
authors.forename: Daniel S
authors.initials: DS
authors.lastname: Fabricant
authors.forename: Dejan
authors.initials: D
authors.lastname: Nikolic
authors.forename: David C
authors.initials: DC
authors.lastname: Lankin
authors.forename: Shao-Nong
authors.initials: SN
authors.lastname: Chen
authors.forename: Birgit U
authors.initials: BU
authors.lastname: Jaki
authors.forename: Aleksej
authors.initials: A
authors.lastname: Krunic
authors.forename: Richard B
authors.initials: RB
authors.lastname: van Breemen
authors.forename: Harry H S
authors.initials: HH
authors.lastname: Fong
authors.forename: Norman R
authors.initials: NR
authors.lastname: Farnsworth
authors.forename: Guido F
authors.initials: GF
authors.lastname: Pauli
mesh_terms: D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002109:Caffeic Acids; D031885:Cimicifuga / Q000737:chemistry*; D006146:Guanidines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D010648:Phenylacetates; D018517:Plant Roots / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D011759:Pyrrolidines / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D011985:Receptors, Serotonin / Q000187:drug effects*; D014768:Virginia
chemical_list: D000470:Alkaloids; D002109:Caffeic Acids; D006146:Guanidines; D010648:Phenylacetates; D011759:Pyrrolidines; D011985:Receptors, Serotonin; C504638:cimipronidine; C104425:serotonin 7 receptor; C116090:fukinolic acid