Confirmation of the structure of oxystemokerrin by single crystal x-ray structural analysis and a proposed biosynthesis

Authors

Pitchaya Mungkornasawakul, University of WollongongFollow
Hayden Matthews, University of WollongongFollow
Alison T. Ung, University of WollongongFollow
Stephen G. Pyne, University of WollongongFollow
Araya Jatisatienr, Chiang Mai University
Wilford Lie, University of WollongongFollow
Brian W. Skelton, University of Western Australia
Allan H. White, University of Western Australia

RIS ID

12665

Publication Details

Mungkornasawakul, P., Matthews, H., Ung, A. T., Pyne, S. G., Lie, W., Jatisatienr, A., Skelton, B. W. & White, A. H. (2005). Confirmation of the structure of oxystemokerrin by single crystal x-ray structural analysis and a proposed biosynthesis. ACGC Chemical Research Communications, 19 30-33.

Abstract

The crystal structure of the pentacyclic Stemona alkaloid oxystemokerrin (2), isolated from the roots of Stemona kerrii, is reported, confirming the structure proposed for this compound in a contemporaneous spectroscopic study. This compound is a diastereomer of stemocurtisinol (3), whose structure we have recently reported from S. curtisii, also confirmed by a single-crystal X-ray study. These alkaloids have opposite configurations at C-4 and C-19. A possible biosynthetic pathway for the biosynthesis of 2 and 3 is proposed.