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.

Publication Title

Tetrahedron Letters

ISSN

0040-4039

Recommended Citation

Kam, T.S.; Low, Y.Y.; Lim, K.H.; Choo, Y.M.; Pang, H.S.; Etoh, T.; Hayashi, M.; and Komiyama, K., "Structure, biological activity, and a biomimetic partial synthesis of the lirofolines, novel pentacylic indole alkaloids from Tabernaemontana" (2010). Research Publications (2006 to 2010). 4546.
https://knova.um.edu.my/research_publications_2006_2010/4546

Divisions

CHEMISTRY

Volume

51

Publisher

Elsevier

Additional Information

Department of Chemistry, University of Malaya