Journal
TETRAHEDRON LETTERS
Volume 51, Issue 2, Pages 269-272Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2009.10.122
Keywords
Alkaloids; NMR; Partial synthesis; Biological activity; Tabernaemontana
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Funding
- University of Malaya (UMRG)
- MOSTI, Malaysia (ScienceFund)
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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 mu g/ml, respectively). (C) 2009 Elsevier Ltd. All rights reserved.
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