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

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posted on 2010-11-29, 00:00 authored by Shin-Jowl Tan, Yun-Yee Low, Yeun-Mun Choo, Zanariah Abdullah, Tadahiro Etoh, Masahiko Hayashi, Kanki Komiyama, Toh-Seok Kam
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, 15) 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.

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