Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla

Yeap, Joanne Soon Yee and Tan, Chun Hoe and Yong, Kien Thai and Lim, Kuan Hon and Lim, Siew Huah and Low, Yun Yee and Kam, Toh Seok (2020) Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla. Phytochemistry, 176. p. 112391. ISSN 0031-9422, DOI https://doi.org/10.1016/j.phytochem.2020.112391.

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Official URL: https://doi.org/10.1016/j.phytochem.2020.112391

Abstract

Fourteen previously undescribed alkaloids comprising two N-1-hydroxymethylmacroline alkaloids, one talpinine-type oxindole acetal, a pair of equilibrating talpinine-type oxindole hemiacetals, eight oxidized derivatives of sarpagine- and akuammiline-type indole alkaloids, in addition to alstochalotine a diastereomer of gelsochalotine recently isolated from Gelsemium elegans, were isolated from the leaf and stem-bark extracts of Alstonia penangiana. The structures and relative configurations of these alkaloids were established using NMR, MS, and in one instance, confirmed by X-ray diffraction analysis. An NMR-based method is described as a useful chemotaxonomic tool for differentiating between A. penangiana and A. macrophylla. Several of the alkaloids isolated showed appreciable growth inhibitory effects when tested against a number of human cancer cell lines. © 2020 Elsevier Ltd

Item Type: Article
Funders: University of Malaya ( UMRG-RP036-17AFR ), MOHE , Malaysia ( FRGS/1/2019/STG01/UM/02/23 )
Uncontrolled Keywords: Alstonia penangiana; Apocynaceae; Indole alkaloids; NMR; X-ray crystallography; Cytotoxicity
Subjects: Q Science > QD Chemistry
Q Science > QH Natural history
Divisions: Faculty of Science > Department of Chemistry
Faculty of Science > Institute of Biological Sciences
Depositing User: Ms. Juhaida Abd Rahim
Date Deposited: 04 Jun 2020 04:18
Last Modified: 04 Jun 2020 04:18
URI: http://eprints.um.edu.my/id/eprint/24656

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