Absolute configuration of myrobotinol, new fused-hexacyclic alkaloid skeleton from Myrioneuron nutans

Van Cuong Pham; Akino Jossang; Thierry Sévenet; Van Hung Nguyen; Bernard Bodo

doi:10.1021/jo7017203

Absolute configuration of myrobotinol, new fused-hexacyclic alkaloid skeleton from Myrioneuron nutans

J Org Chem. 2007 Dec 7;72(25):9826-9. doi: 10.1021/jo7017203. Epub 2007 Nov 14.

Authors

Van Cuong Pham¹, Akino Jossang, Thierry Sévenet, Van Hung Nguyen, Bernard Bodo

Affiliation

¹ Laboratoire de Chimie et Biochimie des Substances Naturelles-CNRS, Muséum National d'Histoire Naturelle, 63 rue Buffon, 75005 Paris, France. phamvc@ich.vast.ac.vn

PMID: 17999527
DOI: 10.1021/jo7017203

Abstract

Myrobotinol (1) was isolated from the leaves of Myrioneuron nutans (Rubiaceae) and its structure determined from spectral data, including mass spectrometry and 2D NMR. This compound presents a new hexacyclic alkaloid skeleton including a 1,3-oxazine and aminal functionality. The absolute configuration of myrobotinol was established by using Mosher's method. A plausible biosynthetic pathway starting from L-lysine via Delta-piperideine was proposed for this hexacyclic alkaloid.

Publication types

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

MeSH terms

Alkaloids / biosynthesis
Alkaloids / chemistry
Alkaloids / isolation & purification*
Heterocyclic Compounds, 4 or More Rings / chemical synthesis
Heterocyclic Compounds, 4 or More Rings / chemistry*
Heterocyclic Compounds, 4 or More Rings / isolation & purification
Magnetic Resonance Spectroscopy / methods
Magnetic Resonance Spectroscopy / standards
Molecular Conformation
Plant Leaves / chemistry*
Plant Leaves / metabolism
Reference Standards
Rubiaceae / chemistry*

Substances

Alkaloids
Heterocyclic Compounds, 4 or More Rings
myrobotinol