The Variability of Free Amino Acids and Related Compounds in Legume Seeds

Bell, E. A.; Qureshi, M.Yasin; Charlwood, B. V.; Pilbeam, David J.; Evans, Christine S.

doi:10.1007/978-1-4684-2886-5_35

Cited by 3 publications

(7 citation statements)

References 9 publications

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“…l -canavanine (2-amino-4-guanidinooxybutyric acid) is a nonprotein amino acid synthesized by leguminous plants that are members of the Lotoidea, a subfamily of the Leguminosae [13],[14],[16]. l -Canavanine has a structural analogy to l -arginine in that the terminal methylene group of arginine is replaced with oxygen.…”

Section: Supporting Informationmentioning

confidence: 99%

“…A number of such toxic compounds are nonprotein amino acids [11],[12]. The best-characterized example of nonprotein amino acid that plays a defensive role is l -canavanine (2-amino-4-guanidinooxybutyric acid) [13]–[15], which is massively accumulated in the seeds of many legumes (up to 143 mM in Medicago sativa [16]). l -Canavanine is a natural insecticide because it is structurally similar enough to l -arginine (Figure S1) to interfere with l -arginine metabolism and to be incorporated by arginyl-tRNA synthase in de novo proteins resulting in dysfunctional proteins [17]–[19].…”

Section: Introductionmentioning

confidence: 99%

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Plant Insecticide L-Canavanine Repels Drosophila via the Insect Orphan GPCR DmX

et al. 2009

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Section: Supporting Informationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Plant Insecticide L-Canavanine Repels Drosophila via the Insect Orphan GPCR DmX

et al. 2009

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“…This finding was consistent with the view of many taxonomists that these two species should, on morphological grounds, be placed in Vigna. It was also reported [74] that the seeds of 13 Phaseolus species analyzed contained high concentrations of γ-glutamyl-S-methylcysteine, as did 16 out of 20 species of Vigna (Table 2).…”

Section: Withinmentioning

confidence: 67%

“…This finding was consistent with the view of many taxonomists that these two species should, on morphological grounds, be placed in Vigna. It was also reported [74] that the seeds of A survey of the seeds of 120 species of Astragalus [75] showed that the genus could be broadly divided into species that accumulated canavanine (56) and species that accumulated S-methylcysteine (59) and its γ-glutamyl derivative. Many species also contained γ-hydroxynorvaline (60), δ-hydroxynorvaline (61), homoserine (17) and δ-acetylornithine (62), but their distributions appeared to be random.…”

Section: Taxa Characterised By the Presence Of Specific Nonprotein Amino Acids Or Associations Of Non-protein Amino Acidsmentioning

confidence: 97%

“…The Hippocastanaceae: Branched-chain C 6 and C 7 cyclopropane-containing amino acids are found in species of all three of the closely related families Aceraceae, Sapindaceae and Hippocastanaceae [90]. In a study of 13 species of Aesculus (Hippocastanaceae) belonging to 5 sections [91] it was shown that seed of A. californica in the section Calothyrus contained major concentrations of 2-amino-4-methylhex-4-enoic acid (74), together with lower concentrations of its glutamyl and 6-hydroxy derivatives, the corresponding saturated compound homoisoleucine (75) and a β-methyl derivative of hypoglycin A (76). All these compounds were absent from other species, except for A. indica, the other representative of Calothyrus whose seeds contained glutamyl-74 and 75.…”

Section: N 4 -Methylasparaginementioning

confidence: 99%

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Non-Protein Amino Acids: A Review of the Biosynthesis and Taxonomic Significance

Bell¹,

Nash

Watson

2008

Natural Product Communications

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The non-protein amino acids, with which we are concerned here, are not incorporated into the proteins of the organisms that synthesize them nor are their residues formed by the post-translational modification of protein amino acid residues. Nonprotein amino acids are of value in the study of relationships between species and higher taxa of organisms because most of them are of restricted distribution. If a particular non-protein amino acid is only known to occur in a limited group of species which are related in other respects then it is probable that these species have all arisen from a common ancestral form in which the biosynthetic pathway to that particular non-protein amino acid already existed.

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L-Canavanine, a Root Exudate From Hairy Vetch (Vicia villosa) Drastically Affecting the Soil Microbial Community and Metabolite Pathways

et al. 2021

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L-Canavanine, a conditionally essential non-proteinogenic amino acid analog to L-arginine, plays important roles in cell division, wound healing, immune function, the release of hormones, and a precursor for the synthesis of nitric oxide (NO). In this report, we found that the L-canavanine is released into the soil from the roots of hairy vetch (Vicia villosa) and declines several weeks after growth, while it was absent in bulk proxy. Hairy vetch root was able to exudate L-canavanine in both pots and in vitro conditions in an agar-based medium. The content of the L-canavanine in pots and agar conditions was higher than the field condition. It was also observed that the addition of L-canavanine significantly altered the microbial community composition and diversity in soil. Firmicutes and Actinobacteria became more abundant in the soil after the application of L-canavanine. In contrast, Proteobacteria and Acidobacteria populations were decreased by higher L-canavanine concentration (500 nmol/g soil). Prediction of the soil metabolic pathways using PICRUSt2 estimated that the L-arginine degradation pathway was enriched 1.3-fold when L-canavanine was added to the soil. Results indicated that carbon metabolism-related pathways were altered and the degradation of nitrogen-rich compounds (i.e., amino acids) enriched. The findings of this research showed that secretion of the allelochemical L-canavanine from the root of hairy vetch may alter the soil microbial community and soil metabolite pathways to increase the survival chance of hairy vetch seedlings. This is the first report that L-canavanine acts as an allelochemical that affects the biodiversity of soil microbial community.

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The Variability of Free Amino Acids and Related Compounds in Legume Seeds

Cited by 3 publications

References 9 publications

Plant Insecticide L-Canavanine Repels Drosophila via the Insect Orphan GPCR DmX

Plant Insecticide L-Canavanine Repels Drosophila via the Insect Orphan GPCR DmX

Non-Protein Amino Acids: A Review of the Biosynthesis and Taxonomic Significance

L-Canavanine, a Root Exudate From Hairy Vetch (Vicia villosa) Drastically Affecting the Soil Microbial Community and Metabolite Pathways

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