Absolute Configuration of L-Methionine Sulfoximine as a Toxic Principle in Cnestis palala (LOUR.) MERR.

Murakoshi, Isamu; Sekine, Toshikazu; Maeshima, Kiyomi; Ikegami, Fumio; Yoshinaga, Koichiro; Fujii, Yuichi; Okonogi, Siriporn

doi:10.1248/cpb.41.388

Cited by 19 publications

(11 citation statements)

References 1 publication

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“…These seeds also contain high concentrations of MSO and their acute toxicity to dogs has been confirmed experimentally. Oral administration of the ground seed (347mg/kg) was fatal within 24-25 hr [168].…”

Section: L-methylcysteine Sulphoxide (Smco); Methiinmentioning

confidence: 99%

Toxicity of Non-protein Amino Acids to Humans and Domestic Animals

Nunn

Bell

Watson

et al. 2010

Natural Product Communications

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Non-protein amino acids are common in plants and are present in widely consumed animal feeds and human foods such as alfalfa ( Medicago sativa), which contains canavanine, and lentil ( Lens culinaris), which contains homoarginine. Some occur in wild species that are inadvertently harvested with crop species. Some nonprotein amino acids and metabolites can be toxic to humans, e.g. Lathyrus species contain a neurotoxic oxalyl-amino acid. Some potential toxins may be passed along a food chain via animal intermediates. The increased interest in herbal medicines in the Western countries will increase exposure to such compounds.

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Section: L-methylcysteine Sulphoxide (Smco); Methiinmentioning

confidence: 99%

Toxicity of Non-protein Amino Acids to Humans and Domestic Animals

Nunn

Bell

Watson

et al. 2010

Natural Product Communications

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“…Moreover, some plants of the Cnestis genus, from Madagascar and Asia, were used to kill running dogs by causing severe convulsions. The active compound in the seeds of Cnestis palada [ 162 ], and in the roots of Cnestis glabra and Cnestis polyphylla [ 163 ], was identified as MSO.…”

Section: Mso-induced Epilepsymentioning

confidence: 99%

Epilepsy, Regulation of Brain Energy Metabolism and Neurotransmission

Cloix

Hevor

2009

CMC

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Seizures are the result of a sudden and temporary synchronization of neuronal activity, the reason for which is not clearly understood. Astrocytes participate in the control of neurotransmitter storage and neurotransmission efficacy. They provide fuel to neurons, which need a high level of energy to sustain normal and pathological neuronal activities, such as during epilepsy. Various genetic or induced animal models have been developed and used to study epileptogenic mechanisms. Methionine sulfoximine induces both seizures and the accumulation of brain glycogen, which might be considered as a putative energy store to neurons in various animals. Animals subjected to methionine sulfoximine develop seizures similar to the most striking form of human epilepsy, with a long pre-convulsive period of several hours, a long convulsive period during up to 48 hours and a post convulsive period during which they recover normal behavior. The accumulation of brain glycogen has been demonstrated in both the cortex and cerebellum as early as the pre-convulsive period, indicating that this accumulation is not a consequence of seizures. The accumulation results from an activation of gluconeogenesis specifically localized to astrocytes, both in vivo and in vitro. Both seizures and brain glycogen accumulation vary when using different inbred strains of mice. C57BL/6J is the most “resistant” strain to methionine sulfoximine, while CBA/J is the most “sensitive” one. The present review describes the data obtained on methionine sulfoximine dependent seizures and brain glycogen in the light of neurotransmission, highlighting the relevance of brain glycogen content in epilepsies.

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“…The isolated material was toxic to beagles. 95 (S c S s )-Methionine sulfoximine inhibits both glutamine synthetase and c-glutamylcysteine synthetase; the latter enzyme is the first in the glutathione biosynthetic pathway. Glutamine synthetase using ATP adds a phosphate to the sulfoximine nitrogen atom; both methionine sulfoximine phosphate and ADP are tightly bound to the enzyme.…”

Section: Sulfoximinesmentioning

confidence: 99%

Role of sulfur chirality in the chemical processes of biology

2005

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Chiral structures profoundly influence chemical and biological processes. While chiral carbon biomolecules have received much attention, chirality is also possible in certain sulfur compounds; just as with carbon, there can be differences in the physiological behavior of chiral sulfur compounds. For instance, one drug enantiomer, Nexium (esomeprazole, a chiral sulfoxide), is used for its superior clinical properties as a proton pump inhibitor over the racemic mixture, Prilosec (Losec, omeprazole). This critical review introduces sulfur stereochemistry and nomenclature, and provides a comprehensive approach to chiral sulfur compounds and their enzymatic reactions in general and secondary metabolism. The major structural types of biological interest are sulfonium salts, sulfoxides, and sulfoximines. (103 references).

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Absolute Configuration of L-Methionine Sulfoximine as a Toxic Principle in Cnestis palala (LOUR.) MERR.

Cited by 19 publications

References 1 publication

Toxicity of Non-protein Amino Acids to Humans and Domestic Animals

Toxicity of Non-protein Amino Acids to Humans and Domestic Animals

Epilepsy, Regulation of Brain Energy Metabolism and Neurotransmission

Role of sulfur chirality in the chemical processes of biology

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