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Structures and Synthesis of Hitoyopodins: Bioactive Aromatic Sesquiterpenoids Produced by the Mushroom Coprinopsis
Junnosuke Otaka1, Takeshi Shimizu1, Yushi Futamura1
1Chemical Biology Research Group , RIKEN Center for Sustainable Resource Science , 2-1 Hirosawa, Wako-shi , Saitama 351-0198 , Japan.
Abstract:
The structures of sesquiterpenoids hitoyopodin A (1) and its hydroxy derivatives 2 and 3 from the mushroom Coprinopsis cinerea are reported. Their absolute structures (1-3) with a benzoxabicyclo[3.2.1]octane core were determined by spectroscopy, X-ray crystallography, and total synthesis of 1. Compound 1 displays antiproliferative activity against HL-60 cancer cells and the malarial parasite Plasmodium falciparum. It is proposed that 1 acts as a crucial precursor in the biosynthesis of 2, 3, and lagopodins.
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