Identification and Phytotoxicity of a New Glucosinolate Breakdown Product from Meadowfoam (Limnanthes alba) Seed Meal
| Autor: | Andrew G. Hulting, Suphannika Intanon, Jan F. Stevens, Carol A. Mallory-Smith, Ralph L. Reed |
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| Rok vydání: | 2014 |
| Předmět: |
Glycoside Hydrolases
Thioglucosides Metabolite Glucosinolates Crop Magnoliopsida chemistry.chemical_compound food Isothiocyanates Tandem Mass Spectrometry Food science Herbicides Chemistry General Chemistry Limnanthes alba food.food Biodegradation Environmental Agronomy Germination Glucosinolate Seeds Isothiocyanate Biological Assay Phytotoxicity General Agricultural and Biological Sciences Bioherbicide Thiocyanates Chromatography Liquid |
| Zdroj: | Journal of Agricultural and Food Chemistry. 62:7423-7429 |
| ISSN: | 1520-5118 0021-8561 |
| DOI: | 10.1021/jf5018687 |
| Popis: | 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. |
| Databáze: | OpenAIRE |
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