Novel Cassane and Cleistanthane Diterpenes from Myrospermum f rutescens:  Absolute Stereochemistry of the Cassane Diterpene Series

Four new diterpenes (1−4) were isolated from the leaves of Myrospermum frutescens as minor constituents. Chagresnol (1), 6β,18-diacetoxycassan-13,15-diene (2), and chagreslactone (3) possess cassane skeletons, while chagresnone (4) exhibits a cleistanthane skeleton. Molecular structures and their re...

Full description

Saved in:
Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2004-10, Vol.67 (10), p.1711-1715
Main Authors: Torres-Mendoza, Daniel, Ureña González, Luis David, Ortega-Barría, Eduardo, Coley, Phyllis D, Kursar, Thomas A, Capson, Todd L, McPhail, Kerry, Cubilla-Rios, Luis
Format: Article
Language:English
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:Four new diterpenes (1−4) were isolated from the leaves of Myrospermum frutescens as minor constituents. Chagresnol (1), 6β,18-diacetoxycassan-13,15-diene (2), and chagreslactone (3) possess cassane skeletons, while chagresnone (4) exhibits a cleistanthane skeleton. Molecular structures and their relative stereochemistries were elucidated using NMR spectroscopy in combination with UV, IR, and MS spectral data. Although compound 2 was previously reported as a synthetic product, we report its first isolation as a natural product. Derivative products (10−13) were obtained to test their activities against Chagas's disease. In addition, the absolute stereochemistry of the previously isolated cassane diterpene 5 from M. frutescens is presented.
ISSN:0163-3864
1520-6025
DOI:10.1021/np049890c