title: Cycloartane Triterpenes from the Aerial Parts of Actaea racemosa.
abstract: Investigating the phytochemical equivalence of the aerial parts of Actaea racemosa (syn. Cimicifuga racemosa) relative to the widely used roots/rhizomes, this study provides a perspective for the potential use of renewable ("green") plant parts as a source of black cohosh botanical preparations. In addition to the characterization of Nω-methylserotonin as one representative marker of the Actaea alkaloids, nine cycloartane triterpenes were isolated and characterized, including the two new triterpene glycosides (1S,15R)-1,15,25-trihydroxy-3-O-β-d-xylopyranosyl-acta-(16S,23R,24R)-16,23;16,24-binoxoside (1) and 3-O-α-l-arabinopyranosyl-(1S,24R)-1,24,25-trihydroxy-15-oxo-acta-(16R,23R)-16,23-monoxoside (2). Their structures were elucidated by spectroscopic data interpretation. The relative configuration of 1 was deduced by (1)H iterative full-spin analysis (HiFSA), making it the first example of the complete analysis of the complex (1)H NMR spectrum of a triterpene glycoside. In addition to the new compounds 1 and 2, the aerial plant parts were shown to contain the previously known binoxosides 3, 4, 6, and 7, the monoxoside 8, and the binoxols 5 and 9. Overall, the metabolome of the aerial plant parts consists of a variety of Actaea triterpenes, similar to those found in roots/rhizomes, a tendency toward C-1 and C-7 hydroxylation of the cycloartanol skeleton, a greater abundance of aglycones, and the presence of comparable amounts of Nω-methylserotonin.
authors.affiliation: UIC/NIH Center for Botanical Dietary Supplements Research and ‡Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , Chicago, Illinois 60612, United States.
authors.forename: Ayano
authors.initials: A
authors.lastname: Imai
authors.affiliation: UIC/NIH Center for Botanical Dietary Supplements Research and ‡Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , Chicago, Illinois 60612, United States.
authors.forename: David C
authors.initials: DC
authors.lastname: Lankin
authors.affiliation: UIC/NIH Center for Botanical Dietary Supplements Research and ‡Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , Chicago, Illinois 60612, United States.
authors.forename: Dejan
authors.initials: D
authors.lastname: Nikolić
authors.affiliation: UIC/NIH Center for Botanical Dietary Supplements Research and ‡Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , Chicago, Illinois 60612, United States.
authors.forename: Soyoun
authors.initials: S
authors.lastname: Ahn
authors.affiliation: UIC/NIH Center for Botanical Dietary Supplements Research and ‡Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , Chicago, Illinois 60612, United States.
authors.forename: Richard B
authors.initials: RB
authors.lastname: van Breemen
authors.affiliation: UIC/NIH Center for Botanical Dietary Supplements Research and ‡Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , Chicago, Illinois 60612, United States.
authors.forename: Norman R
authors.initials: NR
authors.lastname: Farnsworth
authors.affiliation: UIC/NIH Center for Botanical Dietary Supplements Research and ‡Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , Chicago, Illinois 60612, United States.
authors.forename: James B
authors.initials: JB
authors.lastname: McAlpine
authors.affiliation: UIC/NIH Center for Botanical Dietary Supplements Research and ‡Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , Chicago, Illinois 60612, United States.
authors.forename: Shao-Nong
authors.initials: SN
authors.lastname: Chen
authors.affiliation: UIC/NIH Center for Botanical Dietary Supplements Research and ‡Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago , Chicago, Illinois 60612, United States.
authors.forename: Guido F
authors.initials: GF
authors.lastname: Pauli
mesh_terms: D031842:Actaea / Q000737:chemistry; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D031885:Cimicifuga / Q000737:chemistry*; D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D035261:Plant Components, Aerial / Q000737:chemistry*; D027343:Rhizome / Q000737:chemistry; D012701:Serotonin / Q000031:analogs & derivatives / Q000032:analysis; D013237:Stereoisomerism; D013714:Tennessee; D014315:Triterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology
chemical_list: C000610165:(1S,15R)-1,15,25-trihydroxy-3-O-beta-d-xylopyranosyl-acta-(16S,23R,24R)-16,23;16,24-binoxoside; C000610166:3-O-alpha-l-arabinopyranosyl-(1S,24R)-1,24,25-trihydroxy-15-oxo-acta-(16R,23R)-16,23-monoxoside; D000470:Alkaloids; D006027:Glycosides; D014315:Triterpenes; C008494:N-methylserotonin; D012701:Serotonin; C085352:cycloartane