Mimosine

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Mimosine
Structural formula of L-mimosine
Ball-and-stick model of the L-mimosine zwitterion
Names
IUPAC name
(2S)-2-Amino-3-(3-hydroxy-4-oxopyridin-1-yl)propanoic acid
Other names
leucenol
Identifiers
3D model (
JSmol
)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard
 100.007.187 Edit this at Wikidata
UNII
  • InChI=1S/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14) checkY
    Key: WZNJWVWKTVETCG-UHFFFAOYSA-N checkY
  • InChI=1/C8H10N2O4/c9-5(8(13)14)3-10-2-1-6(11)7(12)4-10/h1-2,4-5,12H,3,9H2,(H,13,14)
    Key: WZNJWVWKTVETCG-UHFFFAOYAK
  • O=C(O)C(N)CN/1/C=C\C(=O)C(\O)=C\1
Properties
C8H10N2O4
Molar mass 198.178 g·mol−1
Melting point 291 °C (556 °F; 564 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

Mimosine or leucenol is a toxic non-protein amino acid chemically similar to tyrosine. It occurs in some Mimosa spp. (including M. pudica) and all members of the closely related genus Leucaena.

This compound, also known as leucenol, was first isolated from the seeds of

Leucaena glauca Benth.,[1][2] and was later investigated by Adams and coworkers.[3][2]

Properties

Mimosine melts with decomposition. The hydrochloride salt 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

Mimosine arrests dividing cells in the late G1 phase by inhibiting DNA replication initiation.[4] In ruminants, mimosine is degraded to 3,4- and 2,3-dihydroxypyridone (3,4- and 2,3-DHP).

Although

microbes
tolerant 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

Leucaena glauca seeds, 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 of Klebsiella pneumoniae that can degrade mimosine.[7]
Besides, Moe Thida Htun, from Myanmar also found another new sub-species of Baccilus aureus that can degrade mimosine.

Some

pyruvate, and ammonium.[8] A similar enzyme, mimosinase, is produced by Leucaena leucocephala.[9]

See also

References

  1. ^ Mascré, Marcel (1937). "Le leucaenol, principe défini retiré des graines de Leucaena glauca Benth. (Légumineuses Papilionacées)". Comptes Rendus. 204: 890–891.
  2. ^ a b c Henry, Thomas Anderson (1949). "Leucenol". The Plant Alkaloids (4th ed.). The Blakiston Company. pp. 2–3.
  3. doi:10.1021/ja01217a032
    .
  4. ^ T. Krude Exp. Cell Res. Volume 247, Issue 1, 1999, Pages 148-159
  5. ^ Rec. Trav. Chim., 1946, 65 65; Wibaut, Helv. Chim. Acta, 1946, 29 1669; (with Kleipol), Rec. Trav. Chim., 1947, 66 24, 459.
  6. ^ Mascré; Ottenwälder (1941). Bull. Sci. Pharmacol. 3 (3): 65. {{cite journal}}: Missing or empty |title= (help)
  7. doi:10.17138/TGFT(1)45-47
    .
  8. S2CID 18592674
    .
  9. PMID 24351687
    .
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