Mimosine

There still remains to be settled the point of attachment of the a-aminopropionic acid side-chain in leucenol. As the latter is unaffected by boiling hydrobromic or hydriodic acid, an ether linkage at C in 3-hydroxypyridone-4 is unlikely and as the side-chain is eliminated by either pyrolysis or the action of alkali C for the location, as suggested by Kostermanns see mimosine below) is improbable. The balance of evidence seems to be in favour of attachment to the N-atom and additional data supporting this view have been provided by Adams and Jones. ... 

Mimosine, C8H30O4N2, was isolated by Renz from Mimosa pudica L. and Leuccena glauca Benth. It has m.p. 231° dec) [a] , °-21° (H2O) and yields a copper salt, C8H8O4N2, Cu, 2II2O. Nienburg and Taubock ... 

Pyridine Group. Piperine, Piperovatine, Leucenol, Mimosine, Alkaloids of Ricinus communis, Foenugrec, vy eca Nut, Hemlock, Lobelia, Tobacco (Nicotiana spp.). Anabasis aphylla, Pomegranate Root Bark. ... 

Sabinic acid Juniperus sabina Mimosine Leucen glauca... 

Awaya JD, PM Fox, D Borthakur (2005) pyd genes of Rhizobium sp. strain TALI 145 are required for degradation of 3-hydroxy-4-pyridone, an aromatic intermediate in mimosine metabolism. J Bacterial 187 4480-4487. 

Degradation of the toxin mimosine, which is produced by Leucaena glauca and Mimosa pudica, is initiated by the formation of 3-hydroxypyrid-4-one, plausibly by the activity of... 

Table 1 The tyrosinase inhibitory activities of compounds 3-7, as compared to the standard inhibitors (kojic acid and L-mimosine) [43]...

M. Soedario, and D. Borthakur, Mimosine, a toxin produced by tree-legume Leit-caena provides a nodulation competition advantage to mimose-degrading Rluzohium strains. Soil Biol. Biochem. 30 1695 (1998). 

Logi i — 10.2 for the complex of mimosine (226) shows that this mimosine complex is, like the and complexes of this ligand,... 

Hydrox5rpyranones and hydroxypyridinones give a range of colors, from orange through red to violet, with iron(III)-containing solutions (27). Early applications of the use of kojic acid for the colorimetric determination of iron (280), e.g., in iron ores (281), followed and complemented the recommendation, in 1930, that iron(III) be used for the determination of kojic acid - iron(III) was later used for the colorimetric determination of mimosine (282). Other early colorimetric analyses included methods developed for the determination of... 

The use of iron(II) sulfate as a detoxicant for mimosine-affected sheep is an unusual example of iron supplementation (7). It provides an interesting complement and link to the following paragraphs on the use of hydroxypyridinones as detoxicants for iron-burdened humans. 

MImosIne - cytotoxicity and teratogenic activity In rats and thyrotoxic... 

Leucaena spp. contain mimosine, which is degraded to 3-hydroxy-4(l//)-pyridone (3,4-DHP see Section 2.2.4 for more detail). Leucaena, while toxic to unadapted ruminants, is a good source of protein and minerals for many livestock species in some countries. However, if Leucaena is ingested as 50% or more of the diet it will depress growth, cause hair loss, and reduce reproductive performance. Mimosine is a toxin that animals may become adapted to. Ruminal adaptation can be transferred from animal to animal, suggesting a specific set of rumen organisms are capable of detoxifying this amine. 

Mimosine toxicoses include hair loss in horses, cattle, and laboratory animals and fleece loss in sheep. Cataracts and reproductive problems have also been reported in rodent models. Prolonged ingestion of Leucaena by cattle in northern Australia resulted in low weight gains, hair loss and goiter. 

The effects of leucaena and mimosine on nonruminants can be reduced to some extent by diet supplementation with ferrous sulfates. Mimosine forms a complex with iron, which is excreted in the feces. Zinc supplementation has reduced the toxicity in cattle and it is believed that copper and zinc ions bind more strongly to mimosine than most other amino acids. 

Non-protein amino acids Phytohemagglutinins (lectins) Selenocystathionin, L-mimosine... 

Heterocyclic compoimds such as L-mimosine (Fig. 11.10) cause hair loss in mules, horses, and sheep. Mimosine interferes with the enzyme that forms cysteine from methionine. Cysteine, in turn, is needed in growing hair follicles. Mimosine has been tried as a defleecing agent in sheep. After 2 days of intravenous infusion of mimosine, it takes 15 days for a sheep to drop its entire fleece (Reis etal., 1975). However, it has not yet proven practical in sheep ranching. 

Reis, P. J., Tunks, D. A., and Chapman, R. E. (1975). Effects of mimosine, a potential chemical defleecing agent, on wool growth and the skin of sheep. Australian Journal of Biological Sciences 1,69-84. 

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