Discovery of a P450-catalyzed step in vindoline biosynthesis: a link between the aspidosperma and eburnamine alkaloids.

Abstract

Here we report the discovery of a cytochrome P450 that is required for the biosynthesis of vindoline, a plant-derived natural product used for semi-synthesis of several anti-cancer drugs. This enzyme catalyzes the formation of an epoxide that can undergo rearrangement to yield the vincamine-eburnamine backbone, thereby providing evidence for the long-standing hypothesis that the aspidosperma- and eburnamine-type alkaloids are biosynthetically related.

• Authors: Franziska Kellner, Fernando Geu-Flores, Nathaniel H Sherden, Stephanie Brown, Emilien Foureau, Vincent Courdavault, Sarah E O'Connor
• Journal: Chemical communications (Cambridge, England) (Chem Commun (Camb)) Vol. 51 Issue 36 Pg. 7626-8 (May 04 2015) ISSN: 1364-548X [Electronic] England
• PMID: 25850027 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Vinca Alkaloids
• vindoline
• Vinblastine
• Cytochrome P-450 Enzyme System
• eburnamonine

Topics

• Aspidosperma (chemistry, metabolism)
• Biocatalysis
• Cytochrome P-450 Enzyme System (metabolism)
• Molecular Conformation
• Vinblastine (analogs & derivatives, biosynthesis, chemistry)
• Vinca Alkaloids (chemistry, metabolism)