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Hypatulins A and B, Meroterpenes from Hypericum patulum

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journal contribution
posted on 28.09.2016, 19:25 by Naonobu Tanaka, Yuki Yano, Yutaka Tatano, Yoshiki Kashiwada
Two novel prenylated benzophenone related meroterpenes, hypatulins A (1) and B (2), were isolated from the leaves of Hypericum patulum. The structures of 1 and 2 were assigned by spectroscopic analysis, chemical conversion, and calculations of the ECD (electron circular dichroism) spectra. Hypatulin A (1) had a unique densely substituted tricyclic octahydro-1,5-methanopentalene core, while hypatulin B (2) possessed a bicyclo­[3.2.1]­octane moiety. Hypatulin A (1) exhibited antimicrobacterial activity against Bacillus subtilis. A possible biogenetic pathway of the new meroterpenes 1 and 2 from a prenylated benzophenone was presented.