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Record Information
Version2.0
Creation Date2009-12-22 22:31:14 UTC
Update Date2014-12-24 20:26:18 UTC
Accession NumberT3D3663
Identification
Common NameSterigmatocystin
ClassSmall Molecule
DescriptionSterigmatocystin is a mycotoxin of Aspergillus versicolor and Chaetomium species Sterigmatocystin is a poison of the type dermatoxin, from the fungi genus Aspergillus. It appears on crusts of cheese with mold. Sterigmatocystin is a toxic metabolite structurally closely related to the aflatoxins (compare general fact sheet number 2), and consists of a xanthone nucleus attached to a bifuran structure. Sterigmatocystin is mainly produced by the fungi Aspergillus nidulans and A. versicolor. It has been reported in mouldy grain, green coffee beans and cheese although information on its occurrence in foods is limited. It appears to occur much less frequently than the aflatoxins, although analytical methods for its determination have not been as sensitive until recently, and so it is possible that small concentrations in food commodities may not always have been detected. Although it is a potent liver carcinogen similar to aflatoxin B1, current knowledge suggests that it is nowhere near as widespread in its occurrence. If this is the true situation it would be justified to consider sterigmatocystin as no more than a risk to consumers in special or unusual circumstances. Sterigmatocystin is a number of closely related compounds such o-methyl sterigmatocystin are known and some may also occur naturally. The IARC-classification of sterigmatocystin is group 2B, which means it is possibly carcinogenic to humans. In practice, the risk is quite low however, because this substance only appears on cheese crusts with mold, and because of that the chance of daily exposure is very low. Sterigmatocystin is a molded crust is best not to be consumed in whole, but after removing the crust, the cheese can still be consumed. Sterigmatocystin is a different kind of mold than that which appears on cheese itself, which can simply be removed before further consumption. Sterigmatocystin belongs to the family of Sterigmatocystins. These are phenolic compounds whose structure is based on the sterigmatocystin skeleton, a polycyclic aromatic moiety characterized by a furo[3',2':4,5]furan fused to a xanthen-7-one.
Compound Type
  • Ester
  • Ether
  • Food Toxin
  • Fungal Toxin
  • Metabolite
  • Mycotoxin
  • Natural Compound
  • Organic Compound
Chemical Structure
Thumb
Synonyms
Synonym
3a,12c-Dihydro-8-hydroxy-6-methoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one, 9CI
Sterigmatocystine
Chemical FormulaC18H12O6
Average Molecular Mass324.284 g/mol
Monoisotopic Mass324.063 g/mol
CAS Registry Number10048-13-2
IUPAC Name15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-13-one
Traditional Name15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14,16,18-heptaen-13-one
SMILESCOC1=CC2=C(C3C=COC3O2)C2=C1C(=O)C1=C(O)C=CC=C1O2
InChI IdentifierInChI=1/C18H12O6/c1-21-11-7-12-13(8-5-6-22-18(8)24-12)17-15(11)16(20)14-9(19)3-2-4-10(14)23-17/h2-8,18-19H,1H3
InChI KeyInChIKey=UTSVPXMQSFGQTM-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as sterigmatocystins. These are a group of closely related fungal metabolites chemically characterized by a xanthone moiety fused to a dihydrodifurano or a tetrahydrodifurano moiety. The chemical difference among the various sterigmagocystins are the presence or absence of unsaturation at positions 2 and 3 of the difurano ring system, the substitution pattern on positions 6, 7, and 10 of the xanthone system and/or the substituent on position 3 of the difurano system. They are produced by Aspergilus spp. and Bipolaris spp.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassSterigmatocystins
Sub ClassNot Available
Direct ParentSterigmatocystins
Alternative Parents
Substituents
  • Sterigmatocystin backbone
  • Xanthone
  • Dibenzopyran
  • Xanthene
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Coumaran
  • Anisole
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Dihydrofuran
  • Vinylogous ester
  • Vinylogous acid
  • Ether
  • Oxacycle
  • Acetal
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginEndogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point246°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.17 g/LALOGPS
logP2.73ALOGPS
logP3.1ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)8.38ChemAxon
pKa (Strongest Basic)-3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area74.22 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity83.7 m³·mol⁻¹ChemAxon
Polarizability31.51 ųChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001j-1191000000-0a6fb0c05d0662b97bacJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0fer-2019000000-7b902eddc1918abd0dfdJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-57d3fd838ffa3cafae4eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0029000000-a3b6c07cd97d495b3641JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-054o-1492000000-fa083bd25b5fbd820615JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-46e1583b9996ec69f9aeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0019000000-b69f8ae4547345c5a2baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0aor-4595000000-461228ac7946dfc70893JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0009000000-3ccf9c8a3e8c981e7a46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-004i-0009000000-3ccf9c8a3e8c981e7a46JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-0392000000-400e743e9316fb4b6848JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0009000000-1e58a8f96c64172c0c0fJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-0039000000-91dca4d1af8ba1704d02JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-2792000000-0293fe4b2f7e8ea52e84JSpectraViewer
Toxicity Profile
Route of ExposureOral, dermal, inhalation, and parenteral (contaminated drugs). (6)
Mechanism of ToxicitySterigmatocystin's carcinogenic properties are a result of its ability to form guanyl DNA adducts and bind to DNA. In addition, DNA adduct formation causes enhanced production of reactive oxygen species and an imbalance in antioxidant defense, leading to enhanced lipid peroxidation that causes cell damage. (1, 4, 5)
MetabolismThe major urinary metabolite is identified as sterigmatocystin-beta-d-glucuronide. Another metabolite is 1,2-dihydro-2-(N7-guanyl)-1-hydroxysterigmatocystin. (2, 3)
Toxicity ValuesLD50: 166 mg/kg (Rat, 10 days) (7) LD50: >800 mg/kg (Mouse) (7) LD50: 60-65 mg/kg (Intraperitoneal, Rat) (7)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)2B, possibly carcinogenic to humans. (12)
Uses/SourcesThe occurrence of sterigmatocystin in raw materials and foods has not been reported often. The instances reported have usually been on mouldy, or poor quality materials such as wheat, maize, animal feed, hard cheese, pecan nuts and green coffee beans. (13)
Minimum Risk LevelNot Available
Health EffectsSterigmatocystin is considered as a potent carcinogen, mutagen and teratogen. It causes necrosis of the liver and kidney. May also cause hepatocellular carcinoma, acute hepatitis, Reye's syndrome, bile duct cell proliferation, periportal fibrosis, hemorrhages, mucous membrane jaundice, fatty liver changes, cirrhosis in malnourished children, and kwashiorkor. (8, 13)
SymptomsThe first clinical symptoms are anorexia and weight loss. It can also cause diarrhea. (8, 13)
TreatmentPhenobarbital may be administered to enhances hepatic transformation activities and protect against Sterigmatocystin-induced toxicity, carcinogenicity and DNA binding in vivo. In cases of ingestion, feeding large quantities of an adsorbent such as activated charcoal may be used. The hepatic function should be monitored. (8)
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB30588
PubChem Compound ID5284457
ChEMBL IDNot Available
ChemSpider ID4447522
KEGG IDC00961
UniProt IDNot Available
OMIM ID
ChEBI ID18227
BioCyc IDNot Available
CTD IDNot Available
Stitch IDNot Available
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkSterigmatocystin
References
Synthesis ReferenceNot Available
MSDST3D3663.pdf
General References
  1. Essigmann JM, Barker LJ, Fowler KW, Francisco MA, Reinhold VN, Wogan GN: Sterigmatocystin-DNA interactions: identification of a major adduct formed after metabolic activation in vitro. Proc Natl Acad Sci U S A. 1979 Jan;76(1):179-83. [284330 ]
  2. Shimada T, Yamazaki H, Mimura M, Wakamiya N, Ueng YF, Guengerich FP, Inui Y: Characterization of microsomal cytochrome P450 enzymes involved in the oxidation of xenobiotic chemicals in human fetal liver and adult lungs. Drug Metab Dispos. 1996 May;24(5):515-22. [8723730 ]
  3. Karlgren M, Ingelman-Sundberg M: Tumour-specific expression of CYP2W1: its potential as a drug target in cancer therapy. Expert Opin Ther Targets. 2007 Jan;11(1):61-7. [17150034 ]
  4. Sivakumar V, Thanislass J, Niranjali S, Devaraj H: Lipid peroxidation as a possible secondary mechanism of sterigmatocystin toxicity. Hum Exp Toxicol. 2001 Aug;20(8):398-403. [11727790 ]
  5. Stark AA: Mutagenicity and carcinogenicity of mycotoxins: DNA binding as a possible mode of action. Annu Rev Microbiol. 1980;34:235-62. [7002024 ]
  6. Peraica M, Domijan AM: Contamination of food with mycotoxins and human health. Arh Hig Rada Toksikol. 2001 Mar;52(1):23-35. [11370295 ]
  7. Nehlig A, Daval JL, Debry G: Caffeine and the central nervous system: mechanisms of action, biochemical, metabolic and psychostimulant effects. Brain Res Brain Res Rev. 1992 May-Aug;17(2):139-70. [1356551 ]
  8. Grond S, Sablotzki A: Clinical pharmacology of tramadol. Clin Pharmacokinet. 2004;43(13):879-923. [15509185 ]
  9. Rumack BH POISINDEX(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010. Hall AH & Rumack BH (Eds): TOMES(R) Information System Micromedex, Inc., Englewood, CO, 2010; CCIS Volume 143, edition expires Feb, 2010.
  10. IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Man. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work)., p. V10 248 (1976)
  11. Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.
  12. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
  13. Wikipedia. Sterigmatocystin. Last Updated 2 April 2010. [Link]
Gene Regulation
Up-Regulated Genes
GeneGene SymbolGene IDInteractionChromosomeDetails
Down-Regulated GenesNot Available

Targets

1. DNA
General Function:
Used for biological information storage.
Specific Function:
DNA contains the instructions needed for an organism to develop, survive and reproduce.
Molecular Weight:
2.15 x 1012 Da
References
  1. Essigmann JM, Barker LJ, Fowler KW, Francisco MA, Reinhold VN, Wogan GN: Sterigmatocystin-DNA interactions: identification of a major adduct formed after metabolic activation in vitro. Proc Natl Acad Sci U S A. 1979 Jan;76(1):179-83. [284330 ]
  2. Sivakumar V, Thanislass J, Niranjali S, Devaraj H: Lipid peroxidation as a possible secondary mechanism of sterigmatocystin toxicity. Hum Exp Toxicol. 2001 Aug;20(8):398-403. [11727790 ]
  3. Stark AA: Mutagenicity and carcinogenicity of mycotoxins: DNA binding as a possible mode of action. Annu Rev Microbiol. 1980;34:235-62. [7002024 ]
General Function:
Sterol o-acyltransferase activity
Specific Function:
Catalyzes the formation of fatty acid-cholesterol esters, which are less soluble in membranes than cholesterol. Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase.
Gene Name:
SOAT1
Uniprot ID:
P35610
Molecular Weight:
64733.975 Da
References
  1. Sakai K, Ohte S, Ohshiro T, Matsuda D, Masuma R, Rudel LL, Tomoda H: Selective inhibition of acyl-CoA:cholesterol acyltransferase 2 isozyme by flavasperone and sterigmatocystin from Aspergillus species. J Antibiot (Tokyo). 2008 Sep;61(9):568-72. doi: 10.1038/ja.2008.76. [19160525 ]
General Function:
Transferase activity, transferring acyl groups
Specific Function:
Plays a role in lipoprotein assembly and dietary cholesterol absorption. In addition to its acyltransferase activity, it may act as a ligase. May provide cholesteryl esters for lipoprotein secretion from hepatocytes and intestinal mucosa.
Gene Name:
SOAT2
Uniprot ID:
O75908
Molecular Weight:
59895.735 Da
References
  1. Sakai K, Ohte S, Ohshiro T, Matsuda D, Masuma R, Rudel LL, Tomoda H: Selective inhibition of acyl-CoA:cholesterol acyltransferase 2 isozyme by flavasperone and sterigmatocystin from Aspergillus species. J Antibiot (Tokyo). 2008 Sep;61(9):568-72. doi: 10.1038/ja.2008.76. [19160525 ]