A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea

Wong, Soon Kit and Wong, Suet Pick and Sim, Kae Shin and Lim, Siew Huah and Low, Yun Yee and Kam, Toh Seok (2019) A Cytotoxic Indole Characterized by Incorporation of a Unique Carbon–Nitrogen Skeleton and Two Pentacyclic Corynanthean Alkaloids Incorporating a Substituted Tetrahydrofuranone Ring from Kopsia arborea. Journal of Natural Products, 82 (7). pp. 1902-1907. ISSN 0163-3864

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Official URL: https://doi.org/10.1021/acs.jnatprod.9b00255

Abstract

Three new alkaloids were isolated from the bark extract of the Malayan Kopsia arborea, viz., arbophyllidine (1), an unusual pentacyclic, monoterpenoid indole characterized by an absence of oxygen atoms and incorporating a new carbon-nitrogen skeleton, and arbophyllinines A (2) and B (3), two pentacyclic corynanthean alkaloids incorporating a hydroxyethyl-substituted tetrahydrofuranone ring. The structures of the alkaloids were deduced based on analysis of the MS and NMR data and confirmed by X-ray diffraction analyses. The absolute configuration of arbophyllidine (1) was established based on experimental and calculated ECD data, while that of arbophyllinine A was based on X-ray diffraction analysis (Cu Kα). A reasonable biosynthetic route to arbophyllidine (1) from a pericine precursor is presented. Arbophyllidine (1) showed pronounced in vitro growth inhibitory activity against the HT-29 human cancer cell line with IC50 6.2 μM. © 2019 American Chemical Society and American Society of Pharmacognosy.

Item Type: Article
Uncontrolled Keywords: Alkaloids; Indole Alkaloids; Bisindole alkaloids
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Q Science > QH Natural history
Q Science > QR Microbiology
Divisions: Faculty of Science > Dept of Chemistry
Faculty of Science > Institute of Biological Sciences
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 29 Nov 2019 05:09
Last Modified: 29 Nov 2019 05:09
URI: http://eprints.um.edu.my/id/eprint/23156

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