1972
DOI: 10.1021/bi00772a007
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Specificity of the neurotoxin from Lathyrus sativus as an amino acid antagonist

Abstract: This paper reports evidence that a neurotoxin from the pulse Lathyrus sativus behaves as a potent amino acid antagonist in certain microorganisms. The toxin was isolated in 1963 from Lathyrus sativus seeds. Consumption of these seeds as a major calorie source has long been associated with outbreaks of the paralytic human disease known as neurolathyrism. The toxin was assigned the structure ß-oxalyl-L-a,/3-diaminopropionic acid. This paper describes work to confirm the structure of the toxin and to determine it… Show more

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Cited by 35 publications
(7 citation statements)
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“…The production and susceptibility to ODAP may be linked to Zn deficiency in plants and humans, respectively (Lambein et al, 1994;Lambein and Kuo, 1997). ODAP has also been found to inhibit growth of some insects and yeasts (Rao et al, 1964;Mehta et al, 1972) [62,52] , and so may have a plant protective role.…”
Section: Odap Toxicitymentioning
confidence: 99%
“…The production and susceptibility to ODAP may be linked to Zn deficiency in plants and humans, respectively (Lambein et al, 1994;Lambein and Kuo, 1997). ODAP has also been found to inhibit growth of some insects and yeasts (Rao et al, 1964;Mehta et al, 1972) [62,52] , and so may have a plant protective role.…”
Section: Odap Toxicitymentioning
confidence: 99%
“…500 mg) was stirred overnight with 50 ml of methanolic hydrogen chloride (1.25 N). The solvent was removed and the residue was crystallized from dichloromethanepetroleum ether (bp 30-60°) to afford the dimethyl ester: mp 113-114.5°; NMR 7.5 (center of AA'BB' pattern, 5 H, aryl and amide H), 5.77 (d, 1 H, J = 7.5 Hz, sulfonamide ), 4.07 (m, 1 H), 3.88 (s, 3 H), 3.68 (m, 2 H), 3.62 (s, 3 H), and 2.40 ppm (s, 3 H).…”
Section: Experimental Section14mentioning
confidence: 99%
“…The product was eluted with 2.5% formic acid; the ninhydrin-positive fractions were pooled and lyophilized. The residue was washed with a small amount of chilled water and acetone, and was air dried to give 1.70 g (49%) of the desired product as the hydrate, mp 206°( dec with gas evolution), [a]24D -19.5°[ c 2.72 (anhydrous basis), 4 N HC1] [lit.2 [a]27D -36.9°(c 0.66,4 N HC1)].…”
Section: Experimental Section14mentioning
confidence: 99%
“…/3-N-Oxalyl-L-av@-diaminopropionic acid (L-ODAP) is a potent neurotoxic amino acid isolated nearly 3 decades ago from the seeds of Lathyrus sativus (khesari dal, guaya, grass pea, chickling pea) whose consumption by humans is responsible for the disease neurolathyrism prevalent in several parts of Ethiopia and the Indian subcontinent (Rao et al, 1964;Spencer et al, 1986). Molecular mechanisms proposed for the neurotoxicity of L-ODAP generally emphasize its pharmacological and structural analogies to the excitatory amino acid glutamate (Mehta et al, 1972;Lakshmanan and Padmanaban, 1974;Ross et al, 1987Ross et al, , 1989. Ligand displacement (Bridges et al, 1988;Ross et al, 1989) and electrophysiological (MacDonald and Morris, 1984) data show that L-ODAP can interact selectively at the AMPA receptors in the CNS and suggest a possible excitotoxic mechanism for its neurotoxicity.…”
mentioning
confidence: 99%