Ervaoffines E–G, three iboga-type alkaloids featuring ring C cleavage and rearrangement from Ervatamia officinalis. Issue 35 (19th April 2017)

• Record Type: Journal Article
• Authors: Liu, Zhi-Wen; Tang, Ben-Qin; Zhang, Qing-Hua; Wang, Wen-Jing; Huang, Xiao-Jun; Zhang, Jian; Shi, Lei; Zhang, Xiao-Qi; Ye, Wen-Cai
• Is Part Of: RSC advances. Volume 7:Issue 35(2017)
• Page Start: 21883
• Page End: 21889
• Publication Date: 2017-04-19
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c7ra03411c
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : Three novel alkaloids (1–3 ) reveal the high structural plasticity of ring C in iboga-type alkaloids. Abstract : Ervaoffine E (1 ), a new pseudoindoxyl alkaloid possessing a unique rearranged 1, 4-diazacycloheptane skeleton, ervaoffine F (2 ), the first 5, 6-seco-6-nor iboga-type alkaloid featuring ring C cleavage, and ervaoffine G (3 ), bearing an unusual contracted valerolactam ring, together with six known alkaloids were isolated from Ervatamia officinalis . Their structures and absolute configurations were determined by extensive spectroscopic analysis, single-crystal X-ray diffraction and quantum chemical ECD calculations. Plausible biogenetic pathways of these new alkaloids were also proposed and provided new insights into the structural plasticity of ring C in iboga-type alkaloids. Compound3 exhibited a significant neuroprotective effect against oxygen-glucose deprivation (OGD)-induced damage of cultured cortical neurons, an in vitro model of ischemic stroke.