Arbolodinines A−C, biologically-active aspidofractinine-aspidofractinine, aspidofractinine-strychnan, and kopsine-strychnan bisindole alkaloids from Kopsia arborea

Wong, Soon Kit and Yeap, Joanne Soon Yee and Tan, Chun Hoe and Sim, Kae Shin and Lim, Siew Huah and Low, Yun Yee and Kam, Toh Seok (2021) Arbolodinines A−C, biologically-active aspidofractinine-aspidofractinine, aspidofractinine-strychnan, and kopsine-strychnan bisindole alkaloids from Kopsia arborea. Tetrahedron, 78. p. 131802. ISSN 0040-4020

Full text not available from this repository.
Official URL: https://doi.org/10.1016/j.tet.2020.131802

Abstract

Three new bisindole alkaloids, arbolodinines A−C, comprising aspidofractinine-aspidofractinine, aspidofractinine-strychnan, and kopsine-strychnan alkaloids, respectively, were isolated from the stem bark extract of the Malayan Kopsia arborea. The structures of the alkaloids were elucidated based on analysis of the spectroscopic data while the absolute configurations were established based on experimental and calculated ECD data. Arbolodinine A is characterized by the union of two aspidofractinine halves with rare and unusual branching from C-5′ of an iminium/carboxylate zwitterion of one aspidofractinine half to the olefinic C-14 of the other aspidofractinine half, while arbolodinines B and C represent first examples of aspidofractinine-strychnan and kopsine-strychnan bisindoles, respectively. Arbolodinine B displayed pronounced cytotoxic effects against an array of human cancer cell lines, including KB, vincristine-resistant KB, PC-3, HCT 116, HT-29, MDA-MB-231, MCF7 and A549 cells with IC50 values ranging from 1.3 to 9.6 μM. © 2020 Elsevier Ltd

Item Type: Article
Uncontrolled Keywords: Kopsia arborea; Bisindole alkaloids; NMR; DFT; ECD; Cytotoxicity
Subjects: Q Science > QD Chemistry
Q Science > QH Natural history
Divisions: Faculty of Science > Dept of Chemistry
Faculty of Science > Institute of Biological Sciences
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 03 May 2021 07:28
Last Modified: 03 May 2021 07:28
URI: http://eprints.um.edu.my/id/eprint/25929

Actions (login required)

View Item View Item