Leucophyllidine, a cytotoxic bisindole alkaloid constituted from the union of an eburnan and a new vinylquinoline alkaloid

Chew-Yan Gan; Ward T Robinson; Tadahiro Etoh; Masahiko Hayashi; Kanki Komiyama; Toh-Seok Kam

doi:10.1021/ol9016172

Leucophyllidine, a cytotoxic bisindole alkaloid constituted from the union of an eburnan and a new vinylquinoline alkaloid

Org Lett. 2009 Sep 3;11(17):3962-5. doi: 10.1021/ol9016172.

Authors

Chew-Yan Gan¹, Ward T Robinson, Tadahiro Etoh, Masahiko Hayashi, Kanki Komiyama, Toh-Seok Kam

Affiliation

¹ Department of Chemistry, University of Malaya, 50603 Kuala Lumpur, Malaysia.

PMID: 19708704
DOI: 10.1021/ol9016172

Abstract

A cytotoxic bisindole alkaloid possessing an unprecedented structure constituted from the union of an eburnan half and a novel vinylquinoline alkaloid has been isolated from Leuconotis griffithii. The structure was established by analysis of the spectroscopic data and confirmed by X-ray diffraction analysis. A possible biogenetic pathway to the novel quinolinic coupling partner is presented from an Aspidosperma precursor.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Antineoplastic Agents, Phytogenic / chemical synthesis*
Antineoplastic Agents, Phytogenic / chemistry
Antineoplastic Agents, Phytogenic / isolation & purification
Antineoplastic Agents, Phytogenic / pharmacology*
Apocynaceae / chemistry*
Drug Resistance, Neoplasm / drug effects
Drug Screening Assays, Antitumor
Humans
Indole Alkaloids / chemical synthesis*
Indole Alkaloids / chemistry
Indole Alkaloids / isolation & purification
Indole Alkaloids / pharmacology*
KB Cells
Molecular Conformation
Molecular Structure
Nuclear Magnetic Resonance, Biomolecular
Plant Bark / chemistry
Plants, Medicinal / chemistry*
Vincristine / pharmacology
X-Ray Diffraction

Substances

Antineoplastic Agents, Phytogenic
Indole Alkaloids
leucophyllidine
Vincristine