Strychnan and Secoangustilobine A Type Alkaloids from Alstonia spatulata. Revision of the C-20 Configuration of Scholaricine

A total of 25 alkaloids were isolated from the leaf and stem-bark extracts of Alstonia spatulata, of which five are new alkaloids of the strychnan type (alstolucines A−E, 1−5) and the other, a new alkaloid of the secoangustilobine A type (alstolobine A, 6). The structures of these alkaloids were est...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2010-11, Vol.73 (11), p.1891-1897
Main Authors: Tan, Shin-Jowl, Low, Yun-Yee, Choo, Yeun-Mun, Abdullah, Zanariah, Etoh, Tadahiro, Hayashi, Masahiko, Komiyama, Kanki, Kam, Toh-Seok
Format: Article
Language:English
Subjects:
Alstonia - chemistry
Biological and medical sciences
Crystallography, X-Ray
Drug Resistance, Neoplasm - drug effects
General pharmacology
Humans
Indole Alkaloids - chemistry
Indole Alkaloids - isolation & purification
Indole Alkaloids - pharmacology
KB Cells
Malaysia
Medical sciences
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plant Bark - chemistry
Plant Leaves - chemistry
Vincristine - pharmacology
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Summary:A total of 25 alkaloids were isolated from the leaf and stem-bark extracts of Alstonia spatulata, of which five are new alkaloids of the strychnan type (alstolucines A−E, 1−5) and the other, a new alkaloid of the secoangustilobine A type (alstolobine A, 6). The structures of these alkaloids were established using NMR and MS analysis and, in the case of alstolucine B (2), also confirmed by X-ray diffraction analysis. A reinvestigation of the stereochemical assignment of scholaricine (13) by NMR and X-ray analyses indicated that the configuration at C-20 required revision. Alkaloids 1, 2, 6, 7, 9, 10, and 13 reversed multidrug resistance in vincristine-resistant KB cells.
ISSN:0163-3864
1520-6025
DOI:10.1021/np100552b