Identification and Phytotoxicity of a New Glucosinolate Breakdown Product from Meadowfoam (Limnanthes alba) Seed Meal

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...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 2014-07, Vol.62 (30), p.7423-7429
Main Authors: Intanon, Suphannika, Reed, Ralph L, Stevens, Jan F, Hulting, Andrew G, Mallory-Smith, Carol A
Format: Article
Language:English
Subjects:
Biodegradation, Environmental
Biological Assay
biopesticides
Chromatography, Liquid
germination
glucosinolates
Glucosinolates - chemistry
Glucosinolates - pharmacology
Glycoside Hydrolases - metabolism
herbicidal properties
Herbicides - pharmacology
Isothiocyanates - metabolism
lettuce
Limnanthes alba
liquid chromatography
Magnoliopsida - chemistry
metabolites
oils
oilseed crops
phytotoxicity
seeds
Seeds - chemistry
Tandem Mass Spectrometry
Thiocyanates - pharmacology
Thioglucosides - pharmacology
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Summary: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.
ISSN:0021-8561
1520-5118
DOI:10.1021/jf5018687