Title

Semisynthesis and biological activity of stemofoline alkaloids

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.

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Link to publisher version (DOI)

http://dx.doi.org/10.1021/np800806b