7-Oxoorobanchyl acetate and 7-Oxoorobanchol as germination stimulants for root parasitic plants from flax (Linum usitatissimum)

Biosci Biotechnol Biochem. 2009 Jun;73(6):1367-70. doi: 10.1271/bbb.90021. Epub 2009 Jun 7.

Abstract

Germination stimulants for root parasitic plants produced by flax (Linum usitatissimum L.) were purified and characterized. The root exudate of flax contained at least 8 active fractions, and liquid chromatography-tandem mass spectrometry (LC-MS/MS) and gas chromatography mass spectrometry (GC-MS) analyses suggested that there were 6 strigolactones. Two of them were identified as orobanchol and orobanchyl acetate by comparing NMR and GC-MS and LC-MS/MS data with those of synthetic standards. One of the two novel strigolactones was purified and determined as 7-oxoorobanchyl acetate [((3aS,4S,8bS,E)-8,8-dimethyl-3-(((R)-4-methyl-5-oxo-2,5-dihydrofuran-2-yloxy)methylene)-2,7-dioxo-3,3a,4,5,6,7,8,8b-octahydro-2H-indeno[1,2-b]furan-4-yl acetate) by 1D and 2D NMR spectroscopic, and ESI- and EI-MS spectrometric analyses. The other one was also purified and identified as 7-oxoorobanchol. The remaining two compounds could not been characterized due to their scarcity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chromatography, Liquid
  • Flax / chemistry*
  • Furans / pharmacology*
  • Gas Chromatography-Mass Spectrometry
  • Germination / drug effects*
  • Indenes / pharmacology*
  • Magnetic Resonance Spectroscopy
  • Plant Extracts / pharmacology*
  • Plant Roots / drug effects*
  • Tandem Mass Spectrometry

Substances

  • 7-oxoorobanchol
  • 7-oxoorobanchyl acetate
  • Furans
  • Indenes
  • Plant Extracts