title: Iboga-Type Alkaloids from Ervatamia officinalis.
abstract: Seven new iboga-type alkaloids, ervaoffines A-D (1-4), (7S)-3-oxoibogaine hydroxyindolenine (5), ibogaine-5,6-dione (6), and 19-epi-5-oxovoacristine (7), and 10 known alkaloids were isolated from Ervatamia officinalis. The absolute configurations of 1-7 were determined through X-ray diffraction and electronic circular dichroism (ECD) analyses. Ervaoffines A and B represent the first iboga-type pseudoindoxyl alkaloids in which the C-2 spiro carbon configuration is opposite to that of other members of this class, such as iboluteine (8). The relationship between the absolute configuration of the spiro carbons and the Cotton effect in the ECD spectrum is established for the first time for iboga-type pseudoindoxyl and oxindole alkaloids. Additionally, a plausible biogenetic pathway for these alkaloids is proposed.
authors.affiliation: Department of Natural Medicinal Chemistry, China Pharmaceutical University , Nanjing 210009, People's Republic of China.|Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, People's Republic of China.
authors.forename: Ben-Qin
authors.initials: BQ
authors.lastname: Tang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, People's Republic of China.
authors.forename: Wen-Jing
authors.initials: WJ
authors.lastname: Wang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, People's Republic of China.
authors.forename: Xiao-Jun
authors.initials: XJ
authors.lastname: Huang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, People's Republic of China.
authors.forename: Guo-Qiang
authors.initials: GQ
authors.lastname: Li
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, People's Republic of China.
authors.forename: Lei
authors.initials: L
authors.lastname: Wang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, People's Republic of China.
authors.forename: Ren-Wang
authors.initials: RW
authors.lastname: Jiang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, People's Republic of China.
authors.forename: Ting-Ting
authors.initials: TT
authors.lastname: Yang
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, People's Republic of China.
authors.forename: Lei
authors.initials: L
authors.lastname: Shi
authors.affiliation: Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, People's Republic of China.
authors.forename: Xiao-Qi
authors.initials: XQ
authors.lastname: Zhang
authors.affiliation: Department of Natural Medicinal Chemistry, China Pharmaceutical University , Nanjing 210009, People's Republic of China.|Institute of Traditional Chinese Medicine and Natural Products, College of Pharmacy, Jinan University , Guangzhou 510632, People's Republic of China.
authors.forename: Wen-Cai
authors.initials: WC
authors.lastname: Ye
mesh_terms: D002942:Circular Dichroism; D018360:Crystallography, X-Ray; D004365:Drugs, Chinese Herbal / Q000737:chemistry / Q000302:isolation & purification*; D007050:Ibogaine / Q000737:chemistry / Q000302:isolation & purification*; D026121:Indole Alkaloids / Q000737:chemistry / Q000302:isolation & purification*; D008968:Molecular Conformation; D015394:Molecular Structure; D030014:Tabernaemontana / Q000737:chemistry*
chemical_list: D004365:Drugs, Chinese Herbal; D026121:Indole Alkaloids; D007050:Ibogaine