Cycasin

Title: Cycasin
CAS Registry Number: 14901-08-7
CAS Name: (Methyl-ONN-azoxy)methyl b-D-glucopyranoside
Additional Names: methylazoxymethanol b-D-glucoside; b-D-glucosyloxyazoxymethane
Molecular Formula: C8H16N2O7
Molecular Weight: 252.22
Percent Composition: C 38.10%, H 6.39%, N 11.11%, O 44.40%
Literature References: Toxic substance from seeds of Cycas revoluta Thumb. and C. circinalis L., Cycadaceae from Guam: Nishida et al., Bull. Agric. Chem. Soc. Jpn. 19, 77 (1955), C.A. 50, 13756g (1956); Riggs, Chem. Ind. (London) 1956, 926; Matsumoto, Strong, Arch. Biochem. Biophys. 101, 299 (1963). Biological effects, metabolism and mechanism of action of cycasin and its aglycone, methylazoxymethanol: Spatz, Ann. N.Y. Acad. Sci. 163, 848 (1969). Structure: Korsch, Riggs, Tetrahedron Lett. 1964, 523. Toxicology: Laqueur, Spatz, Cancer Res. 28, 2262 (1968). Carcinogenicity and neurotoxicity studies: I. Hirono, Fed. Proc. 31, 1493 (1972). Review of carcinogenicity studies: IARC Monographs 10, 121-138 (1976).
Properties: Needles from water + acetone + ether, dec 154°. [a]D18 -44° (c = 0.62). uv max (0.4M H2SO4): 217 nm. LD50 in rats, mice, hamsters, rabbits, guinea pigs (mg/kg): 562, 500, <250, ~30, <20 orally (Hirono).
Optical Rotation: [a]D18 -44° (c = 0.62)
Absorption maximum: uv max (0.4M H2SO4): 217 nm
Toxicity data: LD50 in rats, mice, hamsters, rabbits, guinea pigs (mg/kg): 562, 500, <250, ~30, <20 orally (Hirono)
Derivative Type: Tetraacetate
Molecular Formula: C16H24N2O11
Molecular Weight: 420.37
Percent Composition: C 45.71%, H 5.75%, N 6.66%, O 41.87%
Properties: Plates from acetone + petr ether, mp 137°. [a]D18 -27° (c = 0.98 in CHCl3).
Melting point: mp 137°
Optical Rotation: [a]D18 -27° (c = 0.98 in CHCl3)
CAUTION: Cycasin has been listed as reasonably anticipated to be a carcinogen: Fourth Annual Report on Carcinogens (NTP 85-002, 1985) p 64; delisted because no U.S. residents exposed: Fifth Annual Report on Carcinogens (NTP 89-239, 1989) p 340.
Cyclacillin Cyclamic Acid Cyclarbamate Cyclethrin Cyclexanone

Cycasin
Chemical structure of cycasin
Identifiers
CAS number 14901-08-7
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]