NDLI: Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan Tabernaemontana corymbosa: Iboga Alkaloids with C-20α Substitution.

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Ibogan, Aspidosperman, Vincamine, and Bisindole Alkaloids from a Malayan Tabernaemontana corymbosa: Iboga Alkaloids with C-20α Substitution.

Content Provider	Semantic Scholar
Author	Nge, Choy-Eng Chong, Kam-Weng Thomas, Noel Francis Lim, Siew-Huah Low, Yun-Yee Kam, Toh-Seok
Copyright Year	2016
Abstract	Ten new indole alkaloids (1-10) comprising five ibogan, two aspidosperman, one vincamine, and two bisindole alkaloids, in addition to 32 known alkaloids, were isolated from the stem-bark extract of a Malayan Tabernaemontana corymbosa. The structures of these alkaloids were determined based on analysis of the NMR and MS data and, in five instances (1, 3, 5, 6, 8), confirmed by X-ray diffraction analysis. Two of the iboga alkaloids, conodusines B (2) and C (3), and the iboga-containing bisindole tabernamidine B (10) are notable for the presence of an α-substituted acetyl group at C-20 of the iboga carbon skeleton. The iboga alkaloid (+)-conodusine E (5) had MS and NMR data that were identical to those of (-)-ervatamine I, recently isolated from Ervatamia hainanensis. Establishment of the absolute configuration of (+)-conodusine E (5) was based on analysis of the ECD data, correlation with (-)-heyneanine, and X-ray analysis, which showed that (+)-5 belongs to the same enantiomeric series as exemplified by (-)-coronaridine. The configuration at C-20' of the previously reported Tabernaemontana bisindole alkaloid 19'-oxotabernamine (renamed tabernamidine B) required revision based on the present results. Several of the bisindoles showed pronounced in vitro growth inhibitory activity against drug-sensitive and vincristine-resistant KB cells.
File Format	PDF HTM / HTML
DOI	10.1021/acs.jnatprod.6b00129
PubMed reference number	27077800
Journal	Medline
Volume Number	79
Issue Number	5
Alternate Webpage(s)	https://s3-eu-west-1.amazonaws.com/pstorage-acs-6854636/4949116/np6b00129_si_001.pdf
Alternate Webpage(s)	https://umexpert.um.edu.my/file/publication/00007913_136987_66045.pdf
Alternate Webpage(s)	https://doi.org/10.1021/acs.jnatprod.6b00129
Journal	Journal of natural products
Language	English
Access Restriction	Open
Content Type	Text
Resource Type	Article

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