Fate of the 16β-hydrogen atom of cholesterol in the biosynthesis of tomatidine and solanidine

Abstract
During the biosynthesis of tomatidine (1) in Lycopersicon pimpinellifolium, the 16β-hydrogen atom of cholesterol is inverted to the 16α-position; the same hydrogen atom is lost during the biosynthesis of solanidine (2) in Solanum tuberosum.

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