Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana

Kam, T.S. and Low, Y.Y. and Lim, K.H. and Choo, Y.M. and Pang, H.S. and Etoh, T. and Hayashi, M. and Komiyama, K. (2010) Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana. Tetrahedron Letters, 51. pp. 269-272. ISSN 0040-4039

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Abstract

Two new pentacyclic indole alkaloids, lirofolines A and B, possessing a novel rearranged ibogan ring system, are obtained from two Malayan Tabernaemontana species ( Tabernaemontana corymbosa and Tabernaemontana divaricata) and the structures are established by analysis of the spectroscopic data. A biomimetic partial synthesis of lirofoline A from ibogaine via the Polonovski reaction is carried out. Lirofolines A and B showed significant activity in reversing multidrug resistance in vincristine-resistant KB cells (IC50 3.4 and 7.5 µg/ml, respectively).

Item Type: Article
Additional Information: Department of Chemistry, University of Malaya
Uncontrolled Keywords: Alkaloids; NMR; Partial synthesis; Biological activity; Tabernaemontana.
Subjects: Q Science > QD Chemistry
Divisions: Faculty of Science > Dept of Chemistry
Depositing User: Ms. Suhaila Syakila Alby
Date Deposited: 15 Oct 2014 01:42
Last Modified: 15 Oct 2014 01:42
URI: http://eprints.um.edu.my/id/eprint/10396

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