Neurotoxins in a Vetch Food:  Stability to Cooking and Removal of γ-Glutamyl-β-cyanoalanine and β-Cyanoalanine and Acute Toxicity from Common Vetch (<i>Vicia sativa</i> L.) Legumes

Ressler, Charlotte; Tatake, Jayant G.; Kaizer, Ellen; Putnam, Daniel H.

doi:10.1021/jf9603745

Cited by 38 publications

(41 citation statements)

References 15 publications

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“…CNAla is known to be a simple and physiologically stable amino acid (28). The production of this compound by the marine bacterium C-979 of 0.26 g/liter, estimated by 1 H-NMR spectroscopy, was quite high.…”

Section: Discussionmentioning

confidence: 99%

β-Cyanoalanine Production by Marine Bacteria on Cyanide-Free Medium and Its Specific Inhibitory Activity toward Cyanobacteria

Yoshikawa

Adachi

Nishijima

et al. 2000

Appl Environ Microbiol

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In screening the culture broth of marine bacteria collected at Yap (Micronesia), Palau (Belau), and Okinawa (the southwest islands of Japan) for antimicroalgal activity, 37 out of 2,594 bacterial isolates tested were found to produce anticyanobacterial substances against Oscillatoria amphibia NIES-361. One strain, C-979, identified as a Vibrio sp., was selected and cultured in 2.4 liters of marine broth 2216 to identify the bioactive compound produced by the strain. The purified very hydrophilic compound (16.4 mg) was determined to be ␤-cyano-L-alanine (LCNAla) by instrumental analyses and the application of the advanced Marfey method. L-CNAla did not inhibit the growth of bacteria, yeast, or eukaryotic microalgae, but some cyanobacteria were found to be sensitive to L-CNAla at a concentration of 0.4 to 25 g/ml. The effect of L-CNAla on some other environmental organisms, including invertebrates and a macroalgae, is discussed. CNAla production in marine broth was examined by thin-layer chromatography for the 37 bacterial isolates which produced an anticyanobacterial substance. The broth of 36 of these strains contained CNAla, suggesting the wide distribution of CNAla production by marine bacteria. This is the first report on bacteria that produce CNAla without a supply of the cyanide ion in the medium.Research studies of inhibitors of bacteria, fungi, and cultured cells have accumulated, and many effective drugs have appeared for clinical use. However, the number of reports of antimicroalgal compounds is relatively small, although these organisms cause such problems as blooms by cyanobacteria, red tide and the production of marine toxins by dinoflagellates, and biofilm formation on marine structures by diatoms. In particular, some bloom-forming cyanobacteria are known to produce toxic metabolites such as anatoxins (8) and microcystins (3). The mechanism by which the cyanobacteria form blooms remains to be investigated, but the threat and damage to human and animal life and to industry are serious. In the present study, we screened strains for antimicroalgal compounds against one cyanobacterium and three eukaryotic microalgae. A culture broth of each of 2,594 marine bacterial strains was examined in this screening, and among them, 37 strains were found to produce anticyanobacterial substances in the culture on marine broth 2216 (MB). Interestingly, no inhibitory activity toward the three eukaryotic microalgae tested was apparent in the broths of any of these bacterial strains.We purified the anticyanobacterial compound from C-979, which showed the highest anticyanobacterial activity. The chemical structure was determined for the compound, and the bioactivity profile was examined. Furthermore, we examined if the above-mentioned 37 strains produce the same anticyanobacterial compound that C-979 produces. MATERIALS AND METHODSMicroalgae and cultivation medium. All the microalgal strains and the media used in this study are listed in Table 1. F/2, K ϩ ESM, MC, SOT, and CT media have been described elsewhere by Guilla...

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Section: Discussionmentioning

confidence: 99%

β-Cyanoalanine Production by Marine Bacteria on Cyanide-Free Medium and Its Specific Inhibitory Activity toward Cyanobacteria

Yoshikawa

Adachi

Nishijima

et al. 2000

Appl Environ Microbiol

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“…As compared to other HPLC methods previously reported for determination of BCA and GCA [7, 8], the major advantages of this method are its simplicity and the stability of reagents and derivatized amino compounds. This allows for accurate, easy determination of BCA and GCA in a large number of samples using unsophisticated equipment such as a basic HPLC system with an UV detector.…”

Section: Resultsmentioning

confidence: 99%

“…These include quantification by diffuse reflectance infrared spectrometry [6] and two high-performance liquid chromatography (HPLC) methods [7, 8]. The goal of this research was to determine whether HPLC chromatography of the ethoxymethylenemalonate (DEEMM) derivatives of free amino acids can be used for determination of BCA and GCA as well as other free amino acids in the seeds of V. sativa .…”

Section: Introductionmentioning

confidence: 99%

Determination ofβ-Cyano-L-alanine,γ-Glutamyl-β-cyano-L-alanine, and Common Free Amino Acids inVicia sativa(Fabaceae) Seeds by Reversed-Phase High-Performance Liquid Chromatography

Megı́as

Cortés-Giraldo

Girón‐Calle

et al. 2014

Journal of Analytical Methods in Chemistry

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A method for determination of β-cyano-L-alanine, γ-glutamyl-β-cyano-L-alanine and other free amino acids in Vicia sativa is presented. Seed extracts were derivatized by reaction with diethyl ethoxymethylenemalonate and analyzed by reverse-phase high-performance liquid chromatography. Calibration curves showed very good linearity of the response. The limit of detection and quantification was 0.15 and 0.50 μM, respectively. The method has high intra- (RSD = 0.28–0.31%) and interrepeatability (RSD = 2.76–3.08%) and remarkable accuracy with a 99% recovery in spiked samples. The method is very easy to carry out and allows for ready analysis of large number of samples using very basic HPLC equipment because the derivatized samples are very stable and have very good chromatographic properties. The method has been applied to the determination of γ-glutamyl-β-cyano-L-alanine, β-cyano-L-alanine, and common free amino acids in eight wild populations of V. sativa from southwestern Spain.

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“…For many decades, the inability to remove the γ-glutamyl-β-cyano-alanine (GBCA) seed toxin has 45 hindered common vetch's use in agriculture (Pfeffer and Ressler, 1967;Roy et al, 1996), leaving this 46 resilient plant as an "orphan" legume. We envisage that the development of a zero-toxin vetch variety 47 would facilitate its use for animal feed, specifically chickens and pigs, and human consumption 48 (Ressler et al, 1997;Collins et al, 2002). As the production costs of common vetch are approximately 49 50% less than competing legumes such as lentils (unpublished data), we predict that zero-toxin 50 varieties would rapidly surpass lentil in pig and poultry production.…”

Section: Introduction 25mentioning

confidence: 99%

Common Vetch: a drought tolerant, high protein neglected leguminous crop with potential as a sustainable food source

Nguyen

Riley

Nagel

et al. 2020

Preprint

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13• Global demand for protein is predicted to increase by 50% by 2050. To meet the increasing demand 14 whilst ensuring sustainability, protein sources that generate low-greenhouse gas emissions are required 15 and protein-rich legume seeds have the potential to make a significant contribution. Legumes like 16 common vetch (Vicia sativa) that grow in marginal cropping zones and are drought tolerant and 17 resilient to changeable annual weather patterns, will be in high demand as the climate changes. In 18 common vetch, the inability to eliminate the γ-glutamyl-β-cyano-alanine (GBCA) toxin present in the 19 seed has hindered its utility as a human and animal food for many decades, leaving this highly resilient 20 species an "orphan" legume. However, the availability of the vetch genome and transcriptome data 21 together with the application of CRISPR-Cas genome editing technologies lay the foundations to 22 eliminate the GBCA toxin constraint. In the near future, we anticipate that a zero-toxin vetch variety 23 will become a significant contributor to global protein demand. 24

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Neurotoxins in a Vetch Food: Stability to Cooking and Removal of γ-Glutamyl-β-cyanoalanine and β-Cyanoalanine and Acute Toxicity from Common Vetch (Vicia sativa L.) Legumes

Cited by 38 publications

References 15 publications

β-Cyanoalanine Production by Marine Bacteria on Cyanide-Free Medium and Its Specific Inhibitory Activity toward Cyanobacteria

β-Cyanoalanine Production by Marine Bacteria on Cyanide-Free Medium and Its Specific Inhibitory Activity toward Cyanobacteria

Determination ofβ-Cyano-L-alanine,γ-Glutamyl-β-cyano-L-alanine, and Common Free Amino Acids inVicia sativa(Fabaceae) Seeds by Reversed-Phase High-Performance Liquid Chromatography

Common Vetch: a drought tolerant, high protein neglected leguminous crop with potential as a sustainable food source

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