Rearranged vibsane-type diterpenes from Viburnum awabuki and photochemical reaction of vibsanin B

Chem Pharm Bull (Tokyo). 2005 Jan;53(1):72-80. doi: 10.1248/cpb.53.72.

Abstract

Nine new diterpenes, neovibsanin D (1), 7-epi-neovibsanin D (2), 15-O-methylneovibsanin F (3), 14-epi-15-O-methylneovibsanin F (4), 15-O-methyl-18-oxoneovibsanin F (5), 2-O-methylneovibsanin H (6), 2-O-methylneovibsanin I (7), neovibsanin G (8), and 14-epi-neovibsanin G (9), were isolated from a methanol extract of the leaves of Viburnum awabuki. Their structures were elucidated to be uniquely rearranged vibsane-type diterpenes by spectroscopic analyses and comparison of NMR data with those of previously reported vibsane-type diterpenes. In addition, irradiation of vibsanin B (12) in methanol with a high-pressure Hg lump led to the direct formation of neovibsanins A (14) and B (15). These results gave a clue to understanding of the biogenetic interconversion of 11-membered vibsanins into neovibsanins.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Diterpenes / chemistry*
  • Diterpenes / isolation & purification
  • Photochemistry
  • Plant Extracts / chemistry
  • Plant Extracts / isolation & purification
  • Plant Leaves
  • Viburnum*

Substances

  • Diterpenes
  • Plant Extracts
  • vibsanol B