Identification and phytotoxicity of a new glucosinolate breakdown product from Meadowfoam (Limnanthes alba) seed meal

J Agric Food Chem. 2014 Jul 30;62(30):7423-9. doi: 10.1021/jf5018687. Epub 2014 Jul 16.

Abstract

Meadowfoam (Limnanthes alba Hartw. ex Benth.) is an oilseed crop grown in the Willamette Valley of Oregon. Meadowfoam seed meal (MSM), a byproduct after oil extraction, contains 2-4% glucosinolate (glucolimnanthin). Activated MSM, produced by adding freshly ground myrosinase-active meadowfoam seeds to MSM, facilitates myrosinase-mediated formation of glucosinolate-derived degradation products with herbicidal activity. In the activated MSM, glucolimnanthin was converted into 3-methoxybenzyl isothiocyanate ("isothiocyanate") within 24 h and was degraded by day three. 3-Methoxyphenylacetonitrile ("nitrile") persisted for at least 6 days. Methoxyphenylacetic acid (MPAA), a previously unknown metabolite of glucolimnanthin, appeared at day three. Its identity was confirmed by LC-UV and high resolution LC-MS/MS comparisons with a standard of MPAA. Isothiocyanate inhibited lettuce germination 8.5- and 14.4-fold more effectively than MPAA and nitrile, respectively. Activated MSM inhibited lettuce germination by 58% and growth by 72% compared with the control. Results of the study suggest that MSM has potential uses as a pre-emergence bioherbicide.

MeSH terms

  • Biodegradation, Environmental
  • Biological Assay
  • Chromatography, Liquid
  • Glucosinolates / chemistry*
  • Glucosinolates / pharmacology*
  • Glycoside Hydrolases / metabolism
  • Herbicides / pharmacology
  • Isothiocyanates / metabolism
  • Magnoliopsida / chemistry*
  • Seeds / chemistry*
  • Tandem Mass Spectrometry
  • Thiocyanates / pharmacology
  • Thioglucosides / pharmacology

Substances

  • Glucosinolates
  • Herbicides
  • Isothiocyanates
  • Thiocyanates
  • Thioglucosides
  • glucolimnanthin
  • 3-methoxybenzyl isothiocyanate
  • Glycoside Hydrolases
  • thioglucosidase