cycasin
Identification
| Name | cycasin |
| IUPAC | (Z)-methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azanium |
| CAS Number | 14901-08-7 |
| FDA UNII | 9H51HL0E1D |
| Molecular Formula | C8 H16 N2 O7 |
| Molecular Weight | 252.22392000 |
| Beilstein | 0025396 |
| XlogP3 | -2.60 (est) |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Soluble in | water, 1e+006 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | oral-guinea pig LD50 20 mg/kg |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | toxic natural substances |
| Recommendation for cycasin usage levels up to | not for fragrance use. |
| Recommendation for cycasin flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
beta-D-
glucopyranoside, (methyl-ONN-azoxy)methyl-
beta-D-
glucosyloxyazoxymethane
methyl-ONN-azoxy)-methyl-beta-D-glucopyranoside
(Z)-
methyl-oxido-[[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethylimino]azanium
methylazoxymethanolbeta-D-glucoside
PubMed:
Toxic phytochemicals and their potential risks for human cancer.
PubMed:
Relative seed and fruit toxicity of the Australian cycads Macrozamia miquelii and Cycas ophiolitica: further evidence for a megafaunal seed dispersal syndrome in cycads, and its possible antiquity.
PubMed:
Effect of methanolic extract of Vernonia amygdalina (common bitter leaf) on lipid peroxidation and antioxidant enzymes in rats exposed to cycasin.
PubMed:
Animal models of brain maldevelopment induced by cycad plant genotoxins.
PubMed:
Cycads and their association with certain neurodegenerative diseases.
PubMed:
Unraveling 50-Year-Old Clues Linking Neurodegeneration and Cancer to Cycad Toxins: Are microRNAs Common Mediators?
PubMed:
Does the cycad genotoxin MAM implicated in Guam ALS-PDC induce disease-relevant changes in mouse brain that includes olfaction?
PubMed:
Is neurodegenerative disease a long-latency response to early-life genotoxin exposure?
PubMed:
Antileishmanial, antitrypanosomal, and cytotoxic screening of ethnopharmacologically selected Peruvian plants.
PubMed:
The cycad genotoxin MAM modulates brain cellular pathways involved in neurodegenerative disease and cancer in a DNA damage-linked manner.
PubMed:
Two genera of Aulacoscelinae beetles reflexively bleed azoxyglycosides found in their host cycads.
PubMed:
A survey of phytotoxic microbial and plant metabolites as potential natural products for pest management.
PubMed:
[Studies on the chemical constituents of the roots of Anemone altaica].
PubMed:
Return of the cycad hypothesis - does the amyotrophic lateral sclerosis/parkinsonism dementia complex (ALS/PDC) of Guam have new implications for global health?
PubMed:
Molecular networks perturbed in a developmental animal model of brain injury.
PubMed:
Azoxyglycoside content and beta-glycosidase activities in leaves of various cycads.
PubMed:
Acute Cycas seed poisoning in Taiwan.
PubMed:
Western Pacific ALS/PDC and flying foxes: What's next?
PubMed:
Cycads: their evolution, toxins, herbivores and insect pollinators.
PubMed:
Behavioral and neurological correlates of ALS-parkinsonism dementia complex in adult mice fed washed cycad flour.
PubMed:
Toxicology. Fruit bats linked to mystery disease.
PubMed:
Cycad neurotoxins, consumption of flying foxes, and ALS-PDC disease in Guam.
PubMed:
Effects of single injection of methylazoxymethanol at postnatal day one on cell proliferation in different brain regions of male rats.
PubMed:
SOS induction of selected naturally occurring substances in Escherichia coli (SOS chromotest).
PubMed:
Damage and repair of nerve cell DNA in toxic stress.
PubMed:
The Guam cycad toxin methylazoxymethanol damages neuronal DNA and modulates tau mRNA expression and excitotoxicity.
PubMed:
Cycad poisoning in cattle in Japan--studies on spontaneous and experimental cases.
PubMed:
Are age-related neurodegenerative diseases linked with various types of magnesium depletion?
PubMed:
Na+-dependent and phlorizin-inhibitable transport of glucose and cycasin in brain endothelial cells.
PubMed:
ApoE and CYP2D6 polymorphism with and without parkinsonism-dementia complex in the people of Chamorro, guam.
PubMed:
Neuroepidemiology of amyotrophic lateral sclerosis: clues to aetiology and pathogenesis.
PubMed:
Motor neuron disease on Guam: geographic and familial occurrence, 1956-85.
PubMed:
Potential role of environmental genotoxic agents in diabetes mellitus and neurodegenerative diseases.
PubMed:
Substrate specificity and transglucosylation catalyzed by cycad beta-glucosidase.
PubMed:
A partially purified beta-glucosidase from Bifidobacterium adolescentis converts cycasin to a mutagenic compound.
PubMed:
Cycad toxin-induced damage of rodent and human pancreatic beta-cells.
PubMed:
Genotoxic activity in vivo of the naturally occurring glucoside, cycasin, in the Drosophila wing spot test.
PubMed:
Early biochemical events in mice exposed to cycas and fed a Nigerian-like diet.
PubMed:
Transport of cycasin by the intestinal Na+/glucose cotransporter.
PubMed:
The magical and medicinal usage of Stangeria eriopus in South Africa.
PubMed:
Tumor incidence in a chemical carcinogenesis study of nonhuman primates.
PubMed:
Seeds of discovery: a new look at one environmental factor in Alzheimer's disease.
PubMed:
Guam ALS-PDC: possible causes.
PubMed:
Content of the neurotoxins cycasin (methylazoxymethanol beta-D-glucoside) and BMAA (beta-N-methylamino-L-alanine) in cycad flour prepared by Guam Chamorros.
PubMed:
Long-latency neurodegenerative disease in the western Pacific.
PubMed:
Slow toxins, biologic markers, and long-latency neurodegenerative disease in the western Pacific region.
PubMed:
Dietary protein and chronic toxicity of 1,2-dimethylhydrazine fed to mice.
PubMed:
Mutagenicity of methylazoxymethanol acetate in the presence of alcohol dehydrogenase, aldehyde dehydrogenase, and rat liver microsomes in Salmonella typhimurium His G46.
PubMed:
Intestinal microflora: metabolism of drugs and carcinogens.
PubMed:
Etiology of Alzheimer's disease: a western pacific view.
PubMed:
Acquired chemical defense in the lycaenid butterfly,Eumaeus atala.
PubMed:
Mutagenic activity of promutagens in plants: indirect evidence of their activation.
PubMed:
A poison tree.
PubMed:
Statistical analysis of a carcinogen mixture experiment. I. Liver carcinogens.
PubMed:
Hepatic and spinal lesions in goats chronically intoxicated with cycasin.
PubMed:
On the distribution of genotoxic factors in various organs of mice treated with cycasin.
PubMed:
Induction of tumors with cycasin in newborn and preweanling rats.
PubMed:
Animal model for colorectal cancer.
PubMed:
Diet and nutrition as risk factors for cancer.
PubMed:
[Experimental multiple primary malignant tumors induced by chemical carcinogen].
PubMed:
Review: putative mutagens and carcinogens in foods. V. Cycad azoxyglycosides.
PubMed:
Potentiation of large intestinal tumorigenicity of cycasin derivative by high-fat diet and Lactobacillus in germfree mice.
PubMed:
Activation of cycasin to a mutagen for Saccharomyces cerevisiae by rat intestinal flora.
PubMed:
Bacterial mutagenicity of natural materials, pyrolysis products and additives in foodstuffs and their association with genotoxic effects in mammals.
PubMed:
Cycasin and its mutagenic metabolites.
PubMed:
Genetic damage caused by methylazoxymethanol acetate, the aglycone of cycasin. Analysis of sister-chromatid exchange frequency under in vivo conditions and in cell cultures.
PubMed:
Comparison of the carcinogenicity of methylazoxymethanol-beta-D-glucosiduronic acid in conventional and germfree Sprague-Dawley rats.
PubMed:
Determination of the carcinogen methylazoxymethyl-beta-D-glucosiduronic acid in rat bile and urine.
PubMed:
Natural carcinogenic products of plant origin.
PubMed:
[Occurrence of neoplasms in the large intestine and role of intestinal bacteria].
PubMed:
Genotoxicity of cycasin in the hepatocyte primary culture/DNA repair test supplemented with beta-glucosidase.
PubMed:
Rapid hepatoma induction in rats by dipentylnitrosamine and its modification by other carcinogens.
PubMed:
Effect of phenobarbital on the development of neoplastic lesions in the liver of cycasin-treated rats.
PubMed:
[Classification, histochemistry and ultrastructure of experimental renal tumors (author's transl)].
PubMed:
Carcinogenicity and hepatotoxicity of cycasin and its aglycone methylazoxymethanol acetate in nonhuman primates.
PubMed:
Role of bacteria in human carcinogenesis.
PubMed:
Mutagenicity of the naturally occurring carcinogen cycasin and synthetic methylazoxymethanol conjugates in Salmonella typhimurium.
PubMed:
Synthesis of the glucuronic acid conjugate of methylazoxymethanol.
PubMed:
DNA fragmentation in some organs of rats and mice treated with cycasin.
PubMed:
Mutagenicity of alkaloids in the Salmonella/microsome system.
PubMed:
Contributions of gnotobiology to nutrition science.
PubMed:
Toxins and carcinogens in the environment: an observation in the tropics.
PubMed:
A practical procedure for testing DNA damage in vivo, proposed for a pre-screening of chemical carcinogens.
PubMed:
[Histology, fine structure and differentiation of experimental Wilms tumors (author's transl)].
PubMed:
Naturally occurring compounds Containing a nitrogen-nitrogen bond.
PubMed:
Cancer and the environment.
PubMed:
Effect of coffee on carcinogenicity of cycasin.
PubMed:
PHA response and methylazoxymethanol acetate.
PubMed:
Pathogenesis of methylazoxymethanol-induced lesions in the postnatal mouse cerebellum.
PubMed:
Carcinogens occurring naturally in foods.
PubMed:
Leiomyomas and leiomyosarcomas of the kidney in 4-day-old BUF rats given methylazoxymethanol acetate intraperitoneally.
PubMed:
Naturally occuring mutagens.
PubMed:
Cycasin.
PubMed:
Experimental carcinogenesis in small aquarium fishes.
PubMed:
[Microorganisms as indicators of the mutagenic activity of chemical compounds and their metabolites].
PubMed:
Intestinal tumors of rats by gastric or intestinal administration of cycad extract and cycasin.
PubMed:
Hepatic tumors of rabbits induced by cycad extract.
PubMed:
Dendritic growth in vitro.
PubMed:
[Ultrastructure of cycasin-induced adenomas of kidney (author's transl)].
PubMed:
Renal carcinogenesis.
PubMed:
The alkylation of nucleic acids of rat and mouse in vivo by the carcinogen 1,2-dimethylhydrazine.
PubMed:
Morphological and biochemical effects of 1,2-dimethylhydrazine and 1-methylhydrazine in rats and mice.
PubMed:
[Cycasin carcinogenesis. (5). Carcinogenic properties of cycasin, methylazoxymethanol and methylazoxymethyl benzoate].
PubMed:
Acute hepatic lesions induced by cycasin.
PubMed:
Induction of a retinal disorder with cycasin in newborn mice and rats.
PubMed:
Relations between postnatal days of mice and carcinogenic effect of cycasin.
PubMed:
High yield of hepatic tumors in rats by cycasin.
PubMed:
Cycasin-induced central nervous system lesions in postnatal mice.
PubMed:
Fine structure of cycasin-induced cerebellar alterations.
PubMed:
Cycasin in cycad materials used in Japan.
PubMed:
Lipid composition of the cerebellum and spinal cord in postnatal cycasin-treated Swiss albino mice: preliminary observations.
PubMed:
Carcinogenicity and neurotoxicity of cycasin with sepcial reference to species differences.
PubMed:
-Glucosidase modulation in preweanling rats and its association with tumor induction by cycasin.
PubMed:
[Natural carcinogens: target organs and species specificity in induction of cancer by single administration of cycasin].
PubMed:
[Natural carcinogens: aglycon-methylazoxymethanol in cycasin].
PubMed:
[Natural carcinogens: isolation of cycasin].
PubMed:
[Natural carcinogens: toxicity and carcinogenicity of cyasin: induction of tumors by cycasin in the seeds of Cycas revoluta].
PubMed:
[Natural carcinogens: hepatic disorders in the rat caused by cycasin, with special reference to the induction of hepatic tumors].
PubMed:
Decomposition of methylazoxymethanol, the aglycone of cycasin, in D 2 O.
PubMed:
An electron microscopic study of cycasin-induced cerebellar alterations.
PubMed:
Shift of target organs in cycasin carcinogenesis.
PubMed:
Dose related effects of cycasin induced renal and hepatic tumors.
PubMed:
Carcinogenic effects of cycasin in Syrian golden hamsters and the transplantability of induced tumors.
PubMed:
High incidence of pulmonary tumors in dd mice by a single injection of cycasin.
PubMed:
[Carcinogenesis by cycasin, with special reference to the target organs].
PubMed:
Tumor induction in C57BL-6 mice by a single administration of cycasin.
PubMed:
Induction of a cerebellar disorder with cycasin in newborn mice and hamsters.
PubMed:
Cycling of cycasin from newborn rats to their mother and back to the newborn.
PubMed:
Cycasin: detection of associated mutagenic activity in vivo.
PubMed:
[Cycasin-induced renal tumors in the Wistar rat with special consideration of the adenoma].
PubMed:
Toxicology of cycasin.
PubMed:
Toxicology of cycasin.
PubMed:
Effect of cycasin on protein synthesis.
PubMed:
Induction of mammary cancer in rats with cycasin: a preliminary report.
PubMed:
Tumor induction in Fischer and Osborne-Mendel rats by a single administration of cycasin.
PubMed:
Transplantability of cycasin-induced tumors in rats, with emphasis on nephroblastomas.
PubMed:
Evidence for transplacental passage of the natural carcinogen cycasin and its aglycone.
PubMed:
Induction of a neurological disorder by cycasin in mice.
PubMed:
Similarities between the biochemical actions of cycasin and dimethylnitrosamine.
PubMed:
Tumor induction in germfree rats with methylazoxymethanol (MAM) and synthetic MAM acetate.
PubMed:
Mutation in Drosophila by methylazoxymethanol, the aglycone of cycasin.
PubMed:
Cycasin synthesis in Seirarctia echo (Lepidoptera) larvae fed methylazoxymethanol.
PubMed:
Role of intestinal microorganisms in determining cycasin toxicity.
PubMed:
[Histological-histochemical studies on the "interstitial cycasin tumor" of rat kidneys].
PubMed:
Mutagenicity of cycasin aglycone (methylazoxymethanol), a naturally occurring carcinogen.
PubMed:
Effect of boiling and storing on cycasin content of Cycas circinalis L.
PubMed:
Studies on methylazoxymethanol, the aglycone of cycasin: methylation of nucleic acids in vitro.
PubMed:
Cycasin excretion in conventional and germfree rats.
PubMed:
Naturally occurring toxicants in foods.
PubMed:
The induction of intestinal neoplasms in rats with the glycoside cycasin and its aglycone.
PubMed:
CYCASIN: RADIOMIMETIC EFFECT.
PubMed:
Cycasin content of Cycas circinalis.
PubMed:
STUDIES ON METHYLAZOXYMETHANOL, THE AGLYCONE OF CYCASIN. ISOLATION, BIOLOGICAL, AND CHEMICAL PROPERTIES.
PubMed:
STUDIES ON METHYLAZOXYMETHANOL, THE AGLYCONE OF CYCASIN: A SYNTHESIS OF METHYLAZOXYMETHYL ACETATE.
PubMed:
RESPONSE OF LIVER NUCLEIC ACIDS AND LIPIDS IN RATS FED CYCAS CIRCINALIS L. ENDOSPERM OR CYCASIN.
PubMed:
EFFECT OF INGESTED CYCASIN ON RAT BLOOD PLASMA CHOLINESTERASE.
PubMed:
CARCINOGENIC EFFECTS OF CYCAD MEAL AND CYCASIN, METHYLAZOXYMETHANOL GLYCOSIDE, IN RATS AND EFFECTS OF CYCASIN IN GERMFREE RATS.
PubMed:
EFFECTS OF CYCAD MEAL AND CYCASIN ON HISTOCHEMICALLY DEMONSTRABLE LIVER PHOSPHATASES AND NON SPECIFIC ESTERASES.
PubMed:
RATES AND KINETICS OF CATALASE SYNTHESIS AND DESTRUCTION IN RATS FED CYCAD AND CYCASIN IN VIVO.
PubMed:
EFFECT OF CYCAD AND CYCASIN FEEDING ON LIVER RNA, DNA, SUCCINIC OXIDASE, AND LIPIDS IN THE RAT.
PubMed:
EFFECTS OF CYCASIN AND CYCAD MEAL.
PubMed:
METHYLAZOXYMETHANOL, THE AGLYCONE OF CYCASIN.