Glucolimnanthin

Genes affecting novel seed constituents in Limnanthes alba Benth: transcriptome analysis of developing embryos and a new genetic map of meadowfoam.[Pubmed:26038713]

PeerJ. 2015 May 19;3:e915.

The seed oil of meadowfoam, a new crop in the Limnanthaceae family, is highly enriched in very long chain fatty acids that are desaturated at the Delta5 position. The unusual oil is desirable for cosmetics and innovative industrial applications and the seed meal remaining after oil extraction contains Glucolimnanthin, a methoxylated benzylglucosinolate whose degradation products are herbicidal and anti-microbial. Here we describe EST analysis of the developing seed transcriptome that identified major genes involved in biosynthesis and assembly of the seed oil and in glucosinolate metabolic pathways. mRNAs encoding acyl-CoA Delta5 desaturase were notably abundant. The library was searched for simple sequence repeats (SSRs) and single nucleotide polymorphisms (SNPs). Fifty-four new SSR markers and eight candidate gene markers were developed and combined with previously developed SSRs to construct a new genetic map for Limnanthes alba. Mapped genes in the lipid biosynthetic pathway encode 3-ketoacyl-CoA synthase (KCS), Delta5 desaturase (Delta5DS), lysophosphatidylacyl-acyl transferase (LPAT), and acyl-CoA diacylglycerol acyl transferase (DGAT). Mapped genes in glucosinolate biosynthetic and degradation pathways encode CYP79A, myrosinase (TGG), and epithiospecifier modifier protein (ESM). The resources developed in this study will further the domestication and improvement of meadowfoam as an oilseed crop.

Identifying Rates of Meadowfoam (Limnanthes alba) Seed Meal Needed for Suppression of Meloidogyne hapla and Pythium irregulare in Soil.[Pubmed:30699611]

Plant Dis. 2014 Sep;98(9):1253-1260.

Meadowfoam (Limnanthes alba) is a commercial oilseed annual crop grown in Oregon. After extracting oil from seed, the remaining seed meal is rich in the secondary plant metabolite Glucolimnanthin, which can be converted into pesticidal compounds such as 3-methoxybenzyl isothiocyanate (ITC) and 3-methoxyphenylacetonitrile (nitrile) in the presence of the enzyme myrosinase. In previous studies, we demonstrated that ITC and nitrile, produced by mixing freshly ground meadowfoam seed with meadowfoam seed meal, are toxic to the plant-parasitic nematode Meloidogyne hapla and the plant pathogen Pythium irregulare. In this study, we evaluated factors that might influence the implementation of meadowfoam seed meal into agricultural production systems for soilborne pathogen and nematode control. Rate-finding experiments demonstrated that a minimum 1.0% seed/seed meal formulation (wt/wt) was necessary to achieve nematode and pathogen suppression; seed meal alone was insufficient for complete control of M. hapla and stimulated the growth of P. irregulare. When this 1.0% seed/seed meal formulation was used, a greater soil amendment rate was required to cause 100% mortality of P. irregulare (1.0% wt/wt) than for M. hapla (0.5% wt/wt). In phytotoxicity experiments, soil amended with the 1.0% seed/seed meal formulation was consistently phytotoxic to wheat, cucumber, and tomato. However, phytotoxic effects were mitigated by a delayed planting into the amended soil. A final assay to monitor concentrations of ITC and nitrile in conjunction with assessing M. hapla and P. irregulare mortality was conducted over a 6-day period in soils amended at 0.5 and 1.0% (wt/wt) with the 1.0% seed/seed meal formulation. The response was rapid, with 100% mortality of both organisms within 2 h after exposure to amended soil. Concentrations of nitrile remained relatively constant over the 6-day period (approximately 0.017 and 0.032 mg/ml at 0.5 and 1.0% amendment rates, respectively), whereas ITC production increased rapidly and peaked 12 to 24 h after amendment (0.083 and 0.171 mg/ml at 0.5 and 1.0% amendment rates, respectively) before returning to near undetectable levels.

Identification and phytotoxicity of a new glucosinolate breakdown product from Meadowfoam (Limnanthes alba) seed meal.[Pubmed:24998843]

J Agric Food Chem. 2014 Jul 30;62(30):7423-9.

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.

Activity of meadowfoam (Limnanthes alba) seed meal glucolimnanthin degradation products against soilborne pathogens.[Pubmed:22142246]

J Agric Food Chem. 2012 Jan 11;60(1):339-45.

Meadowfoam (Limnanthes alba L.) is a herbaceous winter-spring annual grown as a commercial oilseed crop. The meal remaining after oil extraction from the seed contains up to 4% of the glucosinolate Glucolimnanthin. Degradation of Glucolimnanthin yields toxic breakdown products, and therefore the meal may have potential in the management of soilborne pathogens. To maximize the pest-suppressive potential of meadowfoam seed meal, it would be beneficial to know the toxicity of individual Glucolimnanthin degradation products against specific soilborne pathogens. Meloidogyne hapla second-stage juveniles (J2) and Pythium irregulare and Verticillium dahliae mycelial cultures were exposed to Glucolimnanthin as well as its degradation products. Glucolimnanthin and its degradation product, 2-(3-methoxyphenyl)acetamide, were not toxic to any of the soilborne pathogens at concentrations up to 1.0 mg/mL. Two other degradation products, 2-(3-methoxymethyl)ethanethioamide and 3-methoxyphenylacetonitrile, were toxic to M. hapla and P. irregulare but not V. dahliae. The predominant enzyme degradation product, 3-methoxybenzyl isothiocyanate, was the most toxic compound against all of the soilborne pathogens, with M. hapla being the most sensitive with EC(50) values (0.0025 +/- 0.0001 to 0.0027 +/- 0.0001 mg/mL) 20-40 times lower than estimated EC(50) mortality values generated for P. irregulare and V. dahliae (0.05 and 0.1 mg/mL, respectively). The potential exists to manipulate meadowfoam seed meal to promote the production of specific degradation products. The conversion of Glucolimnanthin into its corresponding isothiocyanate should optimize the biopesticidal properties of meadowfoam seed meal against M. hapla, P. irregulare, and V. dahliae.

Profile and quantification of glucosinolates in Pentadiplandra brazzeana Baillon.[Pubmed:21993210]

Phytochemistry. 2012 Jan;73(1):51-6.

Glucosinolates (GLs) present in root, seed, and leaf extracts of Pentadiplandra brazzeana Baillon were characterized and quantified according to the ISO 9167-1 method based on the HPLC analysis of desulfo-GLs. The analyses were complemented by GC-MS analyses of the isothiocyanates (ITCs) generated from GL degradation by myrosinase. Glucotropaeolin (1a), Glucolimnanthin (2a), and glucoaubrietin (3a) were shown to be present in the root extract, whereas the seed mainly contained 3a. 3,4-Dimethoxybenzyl GL (4a), glucobrassicin (5a) and traces of 1a were detected in the leaf extract. The products were fully characterized as their desulfo-counterparts by spectroscopic techniques.

Herbicidal activity of glucosinolate degradation products in fermented meadowfoam ( Limnanthes alba ) seed meal.[Pubmed:19170637]

J Agric Food Chem. 2009 Mar 11;57(5):1821-6.

Meadowfoam ( Limnanthes alba ) is an oilseed crop grown in western Oregon. After extraction of the oil from the seeds, the remaining seed meal contains 2-4% of the glucosinolate Glucolimnanthin. This study investigated the effect of fermentation of seed meal on its chemical composition and the effect of the altered composition on downy brome ( Bromus tectorum ) coleoptile emergence. Incubation of enzyme-inactive seed meal with enzyme-active seeds (1% by weight) resulted in complete degradation of Glucolimnanthin and formation of 3-methoxybenzyl isothiocyanate in 28% yield. Fermentation in the presence of an aqueous solution of FeSO(4) (10 mM) resulted in the formation of 3-methoxyphenylacetonitrile and 2-(3-methoxyphenyl)ethanethioamide, a novel natural product. The formation of the isothiocyanate, the nitrile, and the thioamide, as a total, correlated with an increase of herbicidal potency of the seed meal (r(2) = 0.96). The results of this study open new possibilities for the refinement of glucosinolate-containing seed meals for use as bioherbicides.

Isolation and identification of (3-methoxyphenyl)acetonitrile as a phytotoxin from meadowfoam (Limnanthes alba) seedmeal.[Pubmed:24227117]

J Chem Ecol. 1996 Oct;22(10):1939-49.

Ethyl ether, ethanol, and water extracts of meadowfoam (Limnanthes alba Hartweg ex. Benth.) seedmeal were prepared and bioassayed against velvetleaf (Abutilon theophrasti Medicus) and wheat (Triticum aestivum L. "Cardinal"). Both the ethyl ether and ethanol fractions, but not the water extract, inhibited velvetleaf and wheat radicle elongation. Fractionation of the extracts indicated that (3-methoxyphenyl)acetonitrile (3-MPAN) was the active compound from both extracts, comprising >97% of the active ethanol fraction. 3-Methoxybenzyl isothiocyanate, which had been previously shown to be the major breakdown product of Glucolimnanthin, the majorL. alba glucosinolate, was not detected in either extract. Radicle elongation of velvetleaf and wheat were inhibited by 3-MPAN with I50 (the concentration required to inhibit growth by 50%) values of approximately 4 x 10(-4) M (velvetleaf) and 7x10(-4) M (wheat).

Glucolimnanthin, a plant glucosinolate, increases the metabolism and DNA binding of benzo[a]pyrene in hamster embryo cell cultures.[Pubmed:3356070]

Carcinogenesis. 1988 Apr;9(4):657-60.

Glucosinolates are common components of cruciferous vegetables that can be hydrolyzed during food processing to yield isothiocyanates, some of which have been shown to inhibit the induction of mammary tumors in rats by 7,12-dimethyl-benz[a]anthracene. To determine how intact glucosinolates affect the metabolism of benzo[a]pyrene (B[a]P) in mammalian cells in culture, the effects of a series of glucosinolates on the metabolism and DNA binding of B[a]P were investigated in early passage Syrian hamster embryo cell cultures. Glucolimnanthin, a glucosinolate from Limnanthes douglasii increased the amount of B[a]P metabolized by the hamster embryo cell cultures during a 24 h exposure. The Glucolimnanthin-treated cultures contained a higher proportion of B[a]P-phenol glucuronides and other water-soluble metabolites than control cultures. Cotreatment with glucolimnanthan and [3H]B[a]P for 24 h resulted in a greater than 2-fold increase in the amount of B[a]P bound to DNA and a 3-fold increase in the amount of deoxyguanosine adduct formed by reaction of 7R,8S-dihydroxy-9S,10R-epoxy-7,8,9,10-tetrahydroB[a]P [(+)-anti-B[a]PDE]. The Glucolimnanthin was metabolized essentially completely within 24 h. An increase in B[a]P metabolism similar to that caused by Glucolimnanthin was induced by cotreatment of hamster embryo cell cultures with m-methoxybenzyl isothiocyanate, a metabolite that can be formed from Glucolimnanthin by enzymatic hydrolysis. These results indicate that the glucosinolate Glucolimnanthin can increase the metabolic activation of B[a]P in mammalian cells in culture.