Hypatulins A and B, Meroterpenes from Hypericum patulum

  • Org Lett. 2016 Oct 21;18(20):5360-5363. doi: 10.1021/acs.orglett.6b02725.
Naonobu Tanaka  1  2 ,  Yuki Yano  1 ,  Yutaka Tatano  3 ,  Yoshiki Kashiwada  1
Affiliations
  • 1. Graduate School of Pharmaceutical Sciences, Tokushima University , Tokushima 770-8505, Japan.
  • 2. Graduate School of Bioscience and Bioindustry, Tokushima University , Tokushima 770-8513, Japan.
  • 3. Faculty of Pharmaceutical Sciences, International University of Health and Welfare , Ohtawara 324-8501, Japan.
PMID: 27682178 DOI: 10.1021/acs.orglett.6b02725
Abstract

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.

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