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

Authors

T.S. KamFollow
Y.Y. Low
K.H. Lim
Y.M. Choo
H.S. Pang
T. Etoh
M. Hayashi
K. Komiyama

Document Type

Article (Restricted)

Publication Date

1-1-2010

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).

Keywords

Alkaloids, NMR, Partial synthesis, Biological activity, Tabernaemontana.

Divisions

CHEMISTRY

Publication Title

Tetrahedron Letters

Volume

51

Publisher

Elsevier

Additional Information

Department of Chemistry, University of Malaya