title: New C20-diterpenoid alkaloids from Aconitum vilmorrianum and structural revision of 2-O-acetylorochrine and orochrine.
abstract: Three new C20-diterpenoid alkaloids vilmorrianines E (1), F (2), and G (3) were isolated from the whole plants of Aconitum vilmorrianum, along with one artifact N-chloromethyl vilmorrianine E hydrochloride (4), as well as two known alkaloids hemsleyaconitines F (5) and G (6). The structures of 1-4 were established by HR-ESI-MS, 1D-, 2D-NMR (HMQC, HMBC, and NOESY), and single-crystal X-ray diffraction analysis. In addition, the structures of naturally occurring 2-O-acetylorochrine (7) and orochrine (8) were revised to be the known alkaloids heterophylloidine (9) and deacetyl heterophylloidine (10), respectively, on the basis of consideration of transannular effect and chemical correlations.
authors.affiliation: a Department of Chemistry of Medicinal Natural Products , West China College of Pharmacy, Sichuan University , Chengdu 610041 , China.
authors.forename: Tian-Xing
authors.initials: TX
authors.lastname: Tang
authors.affiliation: a Department of Chemistry of Medicinal Natural Products , West China College of Pharmacy, Sichuan University , Chengdu 610041 , China.
authors.forename: Qi-Feng
authors.initials: QF
authors.lastname: Chen
authors.affiliation: a Department of Chemistry of Medicinal Natural Products , West China College of Pharmacy, Sichuan University , Chengdu 610041 , China.
authors.forename: Xiao-Yu
authors.initials: XY
authors.lastname: Liu
authors.affiliation: a Department of Chemistry of Medicinal Natural Products , West China College of Pharmacy, Sichuan University , Chengdu 610041 , China.
authors.forename: Xi-Xian
authors.initials: XX
authors.lastname: Jian
authors.affiliation: a Department of Chemistry of Medicinal Natural Products , West China College of Pharmacy, Sichuan University , Chengdu 610041 , China.
authors.forename: Feng-Peng
authors.initials: FP
authors.lastname: Wang
mesh_terms: D031841:Aconitum / Q000737:chemistry*; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification*; D015394:Molecular Structure; D018517:Plant Roots / Q000737:chemistry
chemical_list: C525474:2-O-acetylorochrine; D000470:Alkaloids; D004224:Diterpenes; C525473:orochrine; C000610013:vilmorrianine E; C000610014:vilmorrianine F; C000610015:vilmorrianine G
keywords: Aconitum vilmorrianum; diterpenoid alkaloid; structural revision; transannular effect; vilmorrianine