Macroline, talpinine, and sarpagine alkaloids from Alstonia penangiana. An NMR-based method for differentiating between A. penangiana and A. macrophylla.
Alstonia penangiana
Apocynaceae
Cytotoxicity
Indole alkaloids
NMR
X-ray crystallography
Journal
Phytochemistry
ISSN: 1873-3700
Titre abrégé: Phytochemistry
Pays: England
ID NLM: 0151434
Informations de publication
Date de publication:
Aug 2020
Aug 2020
Historique:
received:
20
01
2020
revised:
13
04
2020
accepted:
15
04
2020
pubmed:
11
5
2020
medline:
4
8
2020
entrez:
11
5
2020
Statut:
ppublish
Résumé
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.
Identifiants
pubmed: 32387883
pii: S0031-9422(20)30073-X
doi: 10.1016/j.phytochem.2020.112391
pii:
doi:
Substances chimiques
Alkaloids
0
Indole Alkaloids
0
Oxindoles
0
macroline
0
sarpagine
XD54MPV6VQ
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
112391Informations de copyright
Copyright © 2020 Elsevier Ltd. All rights reserved.
Déclaration de conflit d'intérêts
Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.