Cytoprotective Activity of Minor Constituents ofArtemisia Douglasiana

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Abstract
3α-Hydroxycarvotagenone and its epimer 3β-hydroxy carvotagenone were isolated as a minor mixture and its structure determined by spectral means. The mixture was then used in cytoprotection experiments. The mixture, in spite of possessing a Michael acceptor, did not show cytoprotective activity. The lack of activity was attributed to the presence of a -OH group next to the β-carbon of the Michael acceptor. This -OH group could react in a intramolecular way yielding an epoxide which would produce the inhibition of the Michael acceptor. In order to confirm this, the mixture was acetylated and the mixture of acetates used in our cytoprotection experiments. The mixture of acetates showed a moderate but significant cytoprotection probing the existence of some kind of stereoelectronic interaction between the acceptor and the nucleophile.