Strychnan and secoangustilobine A type alkaloids from alstonia spatulata. Revision of the C-20 configuration of scholaricine

Kam, T.S. and Tan, S.J. and Low, Y.Y. and Choo, Y.M. and Abdullah, Z. and Etoh, T. and Hayashi, M. and Komiyama, K. (2010) Strychnan and secoangustilobine A type alkaloids from alstonia spatulata. Revision of the C-20 configuration of scholaricine. Journal of Natural Products, 73. pp. 1891-1897. ISSN 0163-3864,

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Abstract

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.

Item Type: Article
Funders: UNSPECIFIED
Additional Information: Department of Chemistry, University of Malaya --- doi: 10.1021/np100552b
Uncontrolled Keywords: Alkaloids; NMR; Alstonia spatulata; Alstolucine.
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Department of Chemistry
Depositing User: Ms. Suhaila Syakila Alby
Date Deposited: 04 Nov 2014 06:31
Last Modified: 04 Nov 2014 06:31
URI: http://eprints.um.edu.my/id/eprint/10400

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