Iboga-Type Alkaloids from Ervatamia officinalis.
Ben-Qin Tang, Wen-Jing Wang, Xiao-Jun Huang, Guo-Qiang Li, Lei Wang, Ren-Wang Jiang, Ting-Ting Yang, Lei Shi, Xiao-Qi Zhang, Wen-Cai Ye
Journal of Natural Products August 22, 2014 DOI: 10.1021/np500240b (opens in new tab)
Study at a glance
AI-extracted from the abstract| Characteristics | Phytochemical isolation and structural elucidation Peer reviewed |
|---|---|
| Population | Ervatamia officinalis plant material |
| Topics | Ibogaine |
| Key points | Seven new iboga-type alkaloids were isolated from Ervatamia officinalis, and their absolute configurations were determined by X-ray diffraction and ECD. Ervaoffines A and B are described as the first iboga-type pseudoindoxyl alkaloids with a C-2 spiro carbon configuration opposite to that of other members such as iboluteine. The authors report a link between spiro carbon configuration and the Cotton effect in ECD spectra and propose a biogenetic pathway. |
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.
Citations in the library
Cited by 5
- Bioinspired Collective Syntheses of Iboga-Type Indole Alkaloids. Organic Letters May 20, 2016
- Cytochrome P450 and O-methyltransferase catalyze the final steps in the biosynthesis of the anti-addictive alkaloid ibogaine from Tabernanthe iboga Journal of Biological Chemistry July 20, 2018
- The Iboga Alkaloids. Progress in the chemistry of organic natural products 2017
- Reactivity of the Iboga Skeleton: Oxidation Study of Ibogaine and Voacangine. Journal of Natural Products June 23, 2023
- The iboga enigma: the chemistry and neuropharmacology of iboga alkaloids and related analogs. Natural Product Reports March 4, 2021