Cimipronidine, a cyclic guanidine alkaloid from Cimicifuga racemosa.
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.
Fabricant
Daniel S
DS
Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, Chicago, Illinois 60612, USA.
Nikolic
Dejan
D
Lankin
David C
DC
Chen
Shao-Nong
SN
Jaki
Birgit U
BU
Krunic
Aleksej
A
van Breemen
Richard B
RB
Fong
Harry H S
HH
Farnsworth
Norman R
NR
Pauli
Guido F
GF
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
D000470:Alkaloids; D002109:Caffeic Acids; D006146:Guanidines; D010648:Phenylacetates; D011759:Pyrrolidines; D011985:Receptors, Serotonin; C504638:cimipronidine; C104425:serotonin 7 receptor; C116090:fukinolic acid