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Journal Article
Research Support, N.I.H., Extramural
Research Support, Non-U.S. Gov't
Synthesis of (-)-11-O-Debenzoyltashironin: Neurotrophic Sesquiterpenes Cause Hyperexcitation.
Journal of the American Chemical Society 2017 July 20
11-O-Debenzoyltashironin (1) is a member of the neurotrophic sesquiterpenes, trace plant metabolites that enhance neurite outgrowth in cultured neurons. We report its synthesis in six steps from a butenolide heterodimer via its likely biosynthetic precursor, 3,6-dideoxy-10-hydroxypseudoanisatin, here identified as the chain tautomer of 1. Access to the tashironin chemotype fills a gap in a comparison set of convulsive and neurotrophic sesquiterpenes, which we hypothesized to share a common target. Here we show that both classes mutually hyperexcite rat cortical neurons, consistent with antagonism of inhibitory channels and a mechanism of depolarization-induced neurite outgrowth.
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