Cycasin

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Cycasin
Chemical structure of cycasin
Identifiers
CAS number 14901-08-7
PubChem 5459896
ChemSpider 4573631
KEGG C01418
MeSH D003492
ChEBI CHEBI:CHEBI:17074
Jmol-3D images Image 1
Properties
Molecular formula C8H16N2O7
Molar mass 252.22 g mol−1
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Cycasin is a phytotoxin found in cycads such as Cycas revoluta and Zamia pumila. Both plants are used to produce sago. The butterfly Eumaeus atala, whose larvae feed on Z. pumila, also contains the compound. The seeds of C. revoluta contain the highest level of the toxin.

It induces hepatotoxicity and Zamia staggers, a fatal nervous disease affecting cattle where they browse on the leaves or fruit of cycads.

The enzyme methyl-ONN-azoxymethanol beta-D-glucosyltransferase uses the two substrates UDP-glucose and methyl-ONN-azoxymethanol to produce UDP and cycasin.[2]

See also[edit]

References[edit]

  1. ^ b-D-Glucosyloxyazoxymethane, ChemSpider
  2. ^ Tadera K, Yagi F, Arima M and Kobayashi A (1985). "Formation of cycasin from methylazoxymethanol by UDP-glucosyltransferase from leaves of Japanese cycad". Agric. Biol. Chem. 49 (9): 2827–2828. doi:10.1271/bbb1961.49.2827.