Mimosine
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| IUPAC name
(2S)-2-Amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid
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| Other names
leucenol
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| Identifiers | |
3D model (JSmol)
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| DrugBank | |
| ECHA InfoCard | 100.007.187 |
PubChemCID
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| UNII | |
CompTox Dashboard(EPA)
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| Properties | |
| C8H10N2O4 | |
| Molar mass | 198.178g·mol−1 |
| Melting point | 291 °C (556 °F; 564 K) |
Except where otherwise noted, data are given for materials in theirstandard state(at 25 °C [77 °F], 100 kPa).
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Mimosineorleucenolis a toxicnon-protein amino acidchemically similar totyrosine.It occurs in someMimosaspp.(includingM. pudica) and all members of the closely relatedgenusLeucaena.
This compound, also known as leucenol, was first isolated from the seeds ofLeucaena glaucaBenth.,[1][2]and was later investigated by Adams and coworkers.[3][2]
Properties
[edit]Mimosine melts with decomposition. Thehydrochloridesalt melts at 174.5–175.0 °C with decomposition; the hydrobromide decomposes at 179.5 °C, and the hydroiodide decomposes at 183–183.5 °C.[2]Mimosine only forms monobasic acids, but the methyl ester forms a dihydrochloride, C7H9O2N2(COOMe)•2 HCl•½ H2O, mp. 175–6 °C.[citation needed]
Biological effects
[edit]Mimosine arrests dividing cells in the late G1 phase by inhibiting DNA replication initiation.[4]Inruminants,mimosine is degraded to 3,4- and 2,3-dihydroxypyridone (3,4- and 2,3-DHP).
Althoughtoxicosishas occurred inAustralia,Papua New Guinea,AfricaandFlorida,it has not been recorded in any othertropicaland subtropical regions.GoatsinBurmalost hairwhen fed a diet containing 50% ofLeucaena.Goats andcattleinHawaiiare able to degrade the 3,4-DHPruminally.Tolerance might be related to the presence or absence ofmicrobestolerant to mimosine and 3,4-DHP. It is known that at least Australian goats do not share the abilities of their Hawaiian counterparts.
Bickel and Wibaut[5]found in feeding experiments with rats and mice that leucenol is probably the toxic constituent ofLeucaena glaucaseeds, but they did not observe with these animals the loss of hair that seems to occur when these seeds are fed to cattle.[6]Aung from Myanmar isolated the new subspecies ofKlebsiella pneumoniaethat can degrade mimosine.[7]Besides, Moe Thida Htun, from Myanmar also found another new sub-species of Bacillus aureus that can degrade mimosine.[citation needed]
Somerhizobiaare known to producerhizomimosinase,which consumespyridoxal 5′-phosphateto degrade mimosine into 3,4 dihydroxypyridine,pyruvate,andammonium.[8]A similar enzyme,mimosinase,is produced byLeucaena leucocephala.[9]
See also
[edit]References
[edit]- ^Mascré, Marcel (1937)."Le leucaenol, principe défini retiré des graines deLeucaena glaucaBenth. (Légumineuses Papilionacées) ".Comptes Rendus.204:890–891.
- ^abcHenry, Thomas Anderson (1949). "Leucenol".The Plant Alkaloids(4th ed.). The Blakiston Company. pp. 2–3.
- ^Adams, Roger; Cristol, Stanley J.; Anderson, Arthur A.; Albert, Alfred A. (1945). "The Structure of Leucenol. I".J. Am. Chem. Soc.67:89–92.doi:10.1021/ja01217a032.
- ^T. Krude Exp. Cell Res. Volume 247, Issue 1, 1999, Pages 148-159
- ^Rec. Trav. Chim.,1946,6565; Wibaut,Helv. Chim. Acta,1946,291669; (with Kleipol),Rec. Trav. Chim.,1947,6624, 459.
- ^Mascré; Ottenwälder (1941).Bull. Sci. Pharmacol.3(3): 65.
{{cite journal}}:Missing or empty|title=(help) - ^Aung, A.; ter Meulen, U.; Gessler, F.; Böhnel, H. (2013)."Development, isolation and characterization of a new non-virulent mimosine-degrading Klebsiella pneumoniae strain from the rumen liquor of German steers by using IBT-Göttinger bioreactor".Tropical Grasslands – Forrajes Tropicales.1(1): 45.doi:10.17138/TGFT(1)45-47.
- ^Negi VS, Bingham JP, Li QX, Borthakur D (2013). "midD-encoded 'rhizomimosinase' fromRhizobiumsp. strain TAL1145 is a C–N lyase that catabolizes L-mimosine into 3-hydroxy-4-pyridone, pyruvate, and ammonia ".Amino Acids.44(6): 1537–47.doi:10.1007/s00726-013-1479-z.PMID23462928.S2CID18592674.
- ^Negi VS, Bingham JP, Li QX, Borthakur D (2014)."A Carbon–Nitrogen Lyase fromLeucaena leucocephalaCatalyzes the First Step of Mimosine Degradation ".Plant Physiology.164(2): 922–934.doi:10.1104/pp.113.230870.PMC3912116.PMID24351687.