Semisynthesis and biological activity of stemofoline alkaloids

Authors

Morwenna C. Baird, University of Wollongong
Stephen G. Pyne, University of WollongongFollow
Alison T. Ung, University of Wollongong
Wilford Lie, University of Wollongong
Thanapat Sastraruji, Chiang Mai University
Araya Jatisatienr, Chiang Mai University
Chaiwat Jatisatienr, Chiang Mai University
Srisulak Dheeranupattana, Chiang Mai University
Jaturong Lowlam, Chiang Mai University
Sukanya Boonchalermkit, Department of Environmental Quality Promotion, Thailand

RIS ID

30830

Publication Details

Baird, M. C., Pyne, S. G., Ung, A. T., Lie, W., Sastraruji, T., Jatisatienr, A., Jatisatienr, C., Dheeranupattana, S., Lowlam, J. & Boonchalermkit, S. (2009).Semisynthesis and biological activity of stemofoline alkaloids. Journal of Natural Products, 72 (4), 679-684.

Abstract

The semisynthesis of the Stemona alkaloids (3′R)-stemofolenol (1), (3′S)-stemofolenol (2), methylstemofoline (3), and (3′S)-hydroxystemofoline (5) and the unnatural analogues (11E)-methylstemofoline (15) and 3′R-hydroxystemofoline (11) has been achieved starting from (11Z)-1′,2′-didehydrostemofoline (4). This synthesis allowed, for the first time, access to diastereomerically enriched samples of 1 and 2 and the assignment of their absolute configurations at C-3′. These compounds were obtained in sufficient quantities to allow for their biological testing. In a quantitative assay as AChE inhibitors, (11Z)-1′,2′-didehydrostemofoline (4) and (3′S)-hydroxystemofoline (5) were found to be the most active.