Natural occurrence of methionine sulfoximine in the connaraceae family

Jeannoda, Victor; Rakoto-Ranoromalala, D.A.D.; Valisolalao, Jocelyne; Creppy, E. E.; Dirheimer, G.

doi:10.1016/0378-8741(85)90023-6

Cited by 19 publications

(12 citation statements)

References 22 publications

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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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Section: Mso-induced Epilepsymentioning

confidence: 99%

Epilepsy, Regulation of Brain Energy Metabolism and Neurotransmission

Cloix

Hevor

2009

CMC

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“…This result suggested that the active constituents should be non-polarity compounds. Although several members of the Cnestis genus have already been reported as having cytotoxic activity in methanol, ethanol and aqueous extracts (Jeannoda et al, 1985a;Garon et al, 2007). It was found that the L-methionine sulfoximine was the potent cytotoxic compound in Cnestis (Jeannoda et al, 1985b;Garon et al, 2007).…”

Section: Screening Of Cytotoxic Activitymentioning

confidence: 97%

“…In addition, some plants in Cnestis genus presented with methionine sulfoximine (i.e. C. glabra, C. polyphylla and C. ferruginea), exhibited poisoning in various organism (Jeannoda et al, 1985a;Garon et al, 2007).…”

Section: Introductionmentioning

confidence: 99%

Bio-activities and phytochemical investigation of <i>Cnestis palala</i> (Lour.) Merr.

Dej-adisai¹,

Tinpun²,

Wattanapiromsakul³

et al. 2015

Afr. J. Trad. Compl. Alt. Med.

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Background: In traditional medicines, the root of Cnestis palala was used for the treatment of stomach ache, malaria, urinary track disorders and snakebite. The seed was used for poisoning rat and stray dogs. However, the bioactivities and chemical constituents have not been reported. So, this will be the first report. Results:The results showed that the ethanol leaf and bark extracts were active against S. aureus and S. epidermidis. The hexane leaf and seed extracts and petroleum ether bark and root extracts showed strongly inhibition values against MCF-7. Moreover, the petroleum ether bark extract exhibited high inhibition value against HT-29. Seven compounds were isolated as β-sitosterol-glucoside (CP1), hydroquinone (CP2), β-sitosterol (CP3), mixture of fatty acids (CP4) and ethyl caffeate (CP5), scopoletin (CP6) and 2-nonenal (CP7). The CP2 was strongly active against S. aureus and S. epidermidis, the MIC was showed 30.10 µg/ml and 15.05 µg/ml and the MBC was showed 15 µg/ml and 7.5 µg/ml, respectively. Conclusion: These results suggested that C. palala is a great potential source of anti-microbial agents. Hence, this is the first study, which will be the database for chemical constituents and bioactivities of C. palala.

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“…MSX has been identified in processed foods (in the 1940s) and occurs naturally in the roots and stems of some plant species (25). It is also possible that these compounds are produced as a consequence of the host response and reactive nitrogen or oxygen species (61) or are synthesized endogenously as a by-product of a normal metabolic process (62), which would not be unprecedented for S. enterica.…”

Section: Discussionmentioning

confidence: 99%

“…MSX is found in the roots and seeds of members of the Connaraceae family of plant species and has been determined to be a toxic component of these plants (25). While this is the only example of naturally occurring MSX, in the late 1940s, MSX was identified as a toxic by-product in bleached flour (26)(27)(28).…”

mentioning

confidence: 99%

In Salmonella enterica, the Gcn5-Related Acetyltransferase MddA (Formerly YncA) Acetylates Methionine Sulfoximine and Methionine Sulfone, Blocking Their Toxic Effects

Hentchel¹,

Escalante‐Semerena²

2014

J. Bacteriol.

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Protein and small-molecule acylation reactions are widespread in nature. Many of the enzymes catalyzing acylation reactions belong to the Gcn5-related N-acetyltransferase (GNAT; PF00583) family, named after the yeast Gcn5 protein. The genome of Salmonella enterica serovar Typhimurium LT2 encodes 26 GNATs, 11 of which have no known physiological role. Here, we provide in vivo and in vitro evidence for the role of the MddA (methionine derivative detoxifier; formerly YncA) GNAT in the detoxification of oxidized forms of methionine, including methionine sulfoximine (MSX) and methionine sulfone (MSO). MSX and MSO inhibited the growth of an S. enterica ⌬mddA strain unless glutamine or methionine was present in the medium. We used an in vitro spectrophotometric assay and mass spectrometry to show that MddA acetylated MSX and MSO. An mddA ؉ strain displayed biphasic growth kinetics in the presence of MSX and glutamine. Deletion of two amino acid transporters (GlnHPQ and MetNIQ) in a ⌬mddA strain restored growth in the presence of MSX. Notably, MSO was transported by GlnHPQ but not by MetNIQ. In summary, MddA is the mechanism used by S. enterica to respond to oxidized forms of methionine, which MddA detoxifies by acetyl coenzyme A-dependent acetylation.T he Gcn5-related N-acetyltransferase (GNAT; PF00583) superfamily of proteins (Ͼ10,000 members) is present in all domains of life. GNATs transfer the acetyl group from acetyl coenzyme A (acetyl-CoA) to proteins or small molecules (for reviews, see references 1 and 2). The acetylation targets of GNATs include the N termini of proteins (3, 4), aminoglycoside antibiotics (5), glutamate (6), spermidine (7), aminoalkylphosphonic acid (8), dTDP-fucosamine (9), and tRNAs (10). Some of the first bacterial GNATs characterized were the aminoglycoside N-acetyltransferases from Enterococcus faecium (5) and Serratia marcescens (11), demonstrating GNAT-dependent acetylation and inactivation of antibiotics.GNATs provide protection against a myriad of cellular stressors (5,11,12), and it is possible that the diversity of stressors controlled by GNATs correlates with the environment encountered by the cell. Therefore, the relevance of GNAT function to cell physiology varies among organisms, with respect to not only cellular stressors but metabolic pathways as well. For example, Salmonella enterica (13) and Escherichia coli (14) each contain ϳ26 GNATs, yet actinomycetes, such as Streptomyces lividans (15), encode up to ϳ70 putative GNATs. This suggests that S. lividans occupies a more diverse environment while also maintaining a more complex metabolism.At present, there is limited to no information available on the cellular processes several putative S. enterica GNATs may affect. Not surprisingly, the signals that trigger the synthesis of GNATs, the transcription factors involved in sensing such signals, and the determinants of GNAT substrate specificity remain unknown.In S. enterica, MddA (methionine derivative detoxifier A; formerly YncA [STM1590]) is a putative GNAT with no characterized...

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Natural occurrence of methionine sulfoximine in the connaraceae family

Cited by 19 publications

References 22 publications

Epilepsy, Regulation of Brain Energy Metabolism and Neurotransmission

Epilepsy, Regulation of Brain Energy Metabolism and Neurotransmission

Bio-activities and phytochemical investigation of <i>Cnestis palala</i> (Lour.) Merr.

In Salmonella enterica, the Gcn5-Related Acetyltransferase MddA (Formerly YncA) Acetylates Methionine Sulfoximine and Methionine Sulfone, Blocking Their Toxic Effects

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