Alstorisine A, a nor-monoterpenoid indole alkaloid from cecidogenous leaves of Alstonia scholaris

• Published in: Tetrahedron letters Vol. 57; no. 16; pp. 1754 - 1757
• Main Authors: Chen, Ying-Ying, Yang, Jing, Yang, Xing-Wei, Khan, Afsar, Liu, Lu, Wang, Bei, Zhao, Yun-Li, Liu, Ya-Ping, Ding, Zhong-Tao, Luo, Xiao-Dong
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 20.04.2016; Elsevier
• Subjects: Absolute configuration; Alkaloids; Alstonia scholaris; Chemistry; Chemistry, Organic; Galls; Indoles; Mathematical analysis; Monoterpenoid indole alkaloid; Physical Sciences; Science & Technology; Spectroscopic analysis; Tetrahedrons; Monoterpenoid indole alkaloid; Alstonia scholaris; Absolute configuration; Galls; RHAZINILAM; RHAZYA-STRICTA; IDENTIFICATION; MELODININE E; LEUCONODINES; LEUCONOXINE; FLIGHT MASS-SPECTROMETRY; (-)-LEUCONOXINE; CONTINUUM; A-G
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2016.03.022

[Display omitted] •A nor-monoterpenoid indole alkaloid was isolated from A. scholaris.•A plausible biogenesis of the isolated alkaloid was postulated.•Alstorisine A appeared equally in galls and normal part of cecidogenous leaves.•It was present at 3μg/g as indicated by LC–MS quantitative analysis. Alstorisine A (1), a novel nor-monoterpenoid indole alkaloid with 6/5/6/6 fused-ring system, regarded as a key intermediate from melodinine E to mersicarpine, was isolated from the cecidogenous leaves of Alstonia scholaris. Its structure was identified on the basis of extensive spectroscopic analysis and the comparison of experimental and calculated ECDs. A plausible biogenesis was also postulated.