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Sterigmatocystin information


Sterigmatocystin
Names
Preferred IUPAC name
(3aR,12cS)-8-Hydroxy-6-methoxy-3a,12c-dihydro-7H-furo[3′,2′:4,5]furo[2,3-c]xanthen-7-one
Other names
Sterigmatocystin
Identifiers
CAS Number
  • 10048-13-2 ☒N
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:18227 checkY
ChEMBL
  • ChEMBL524291 checkY
ChemSpider
  • 4447522 checkY
ECHA InfoCard 100.030.131 Edit this at Wikidata
EC Number
  • 233-158-6
KEGG
  • C00961 checkY
PubChem CID
  • 5280389
UNII
  • 5F95211S5Z checkY
CompTox Dashboard (EPA)
  • DTXSID2021280 Edit this at Wikidata
InChI
  • InChI=1S/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/t8-,18+/m0/s1 ☒N
    Key: UTSVPXMQSFGQTM-DCXZOGHSSA-N ☒N
SMILES
  • COC1=C2C(=C3[C@@H]4C=CO[C@@H]4OC3=C1)OC5=C(C2=O)C(=CC=C5)O
Properties
Chemical formula
C18H12O6
Molar mass 324.28 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Sterigmatocystin is a polyketide mycotoxin produced by certain species of Aspergillus. The toxin is naturally found in some cheeses.

Sterigmatocystin is a toxic metabolite structurally closely related to the aflatoxins as it is the penultimate precursor of aflatoxins B1 and G1.[1] It contains 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. A number of closely related compounds such as o-methyl sterigmatocystin are known, and some may also occur naturally.

  1. ^ Yabe K, Matsushima K, Koyama T, Hamasaki T (January 1998). "Purification and Characterization of O-Methyltransferase I Involved in Conversion of Demethylsterigmatocystin to Sterigmatocystin and of Dihydrodemethylsterigmatocystin to Dihydrosterigmatocystin during Aflatoxin Biosynthesis". Applied and Environmental Microbiology. 64 (1): 166–171. Bibcode:1998ApEnM..64..166Y. doi:10.1128/AEM.64.1.166-171.1998. PMC 124688. PMID 16349476.

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Sterigmatocystin

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Sterigmatocystin is a polyketide mycotoxin produced by certain species of Aspergillus. The toxin is naturally found in some cheeses. Sterigmatocystin...

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Fish

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Gliotoxin Ibotenic acid Lolitrem B Muscimol Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins Amygdalin...

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C18H12O6

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324.0634 u) may refer to: Atromentin Hexahydroxytriphenylene (HHTP) Sterigmatocystin "Molar mass of C18H12O6". www.webqc.org. Retrieved 2022-08-22. PubChem...

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Aspergillus rambellii

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was first described in 2005. It accumulates very large amounts of sterigmatocystin, 3-O-methylsterigmatocystin and aflatoxin B1. A. rambellii has been...

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Aspergillus quadrilineatus

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been reported to produce asperthecin, averufin, 7-methoxyaverufin, sterigmatocystin, versicolourin, desferritriacetylfusigen, echinocandin B & E, variacoxanthone...

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Botulinum toxin

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Aspergillus bicolor

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species was first described in 1978. It has been reported to produce sterigmatocystin, versicolorins, and some anthraquinones. Apsergillus bicolor has been...

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Aspergillus parvisclerotigenus

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aflatoxin producers and a new efficient producer of aflatoxin B1, sterigmatocystin and 3-O-methylsterigmatocystin, Aspergillus rambellii sp. nov. Systematic...

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Poison dart frog

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IARC group 2B

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ortho-phenylphenate Special-purpose fibres such as E-glass and '475' glass fibres Sterigmatocystin Streptozotocin Sulfasalazine Sulfallate 1,1,1,2-Tetrachloroethane 1...

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Penicillium inflatum

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is an anamorph species of the genus of Penicillium which produces sterigmatocystin. It is from the Cremei section. A. inflatus has been cultivated on...

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Aspergillus violaceus

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to produce aspermutarubrol, asperthecin, desferritriacetylfusigen, sterigmatocystin, violaceol I, violaceol II, and violaceic acid. A. violaceus has been...

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Aspergillus askiburgiensis

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the Czech Republic. A. askiburgiensis has been reported to produce sterigmatocystin, versicolorins, and cf. monascorubramin. A. askiburgiensis has been...

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Aspergillus microthecius

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been reported to produce asperthecin, averufin, 7-methoxyaverufin, sterigmatocystin, versicolourin, desferritriacetylfusigen, echinocandin B, echinocandin...

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Aspergillus corrugatus

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reported to produce asperthecin, emecorrugatin A, emecorrugatin B, sterigmatocystin, and norsolorinic acid. A. corrugatus has been cultivated on both Czapek...

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Aspergillus flavus

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characterized. A. flavus also produces other toxic compounds including sterigmatocystin, cyclopiazonic acid, kojic acid, β-nitropropionic acid, aspertoxin...

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Clostridium botulinum

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Gliotoxin Ibotenic acid Lolitrem B Muscimol Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins Amygdalin...

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Aspergillus fructiculosus

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species was first described in 1965. It has been reported to produce sterigmatocystin. Raper, K.B.; Fennell, D.I. 1965. The Genus Aspergillus. :1-686 Frisvad...

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Aspergillus versicolor

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is a major producer of the hepatotoxic and carcinogenic mycotoxin sterigmatocystin. Like other Aspergillus species, A. versicolor is an eye, nose, and...

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Aspergillus sublatus

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been reported to produce asperthecin, nidulalin A, nidulalin B, and sterigmatocystin. Horie, Y (1979). "New or interesting Emericella from herbal drugs"...

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Mycotoxin

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Aflatoxin

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aflatoxin contamination Mycotoxins in animal feed Nixtamalization Sterigmatocystin, a related toxin Other ways in which aspergillus can cause disease...

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Ricin

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Tetrodotoxin

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Gliotoxin Ibotenic acid Lolitrem B Muscimol Ochratoxin Patulin Phalloidin Sterigmatocystin Trichothecene Vomitoxin Zeranol Zearalenone Plant toxins Amygdalin...

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Aspergillus flavipes

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species was first described in 1926. It has been reported to produce sterigmatocystin, citrinin, and lovastatin. A. flavipes has been cultivated on both...

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Ciguatera fish poisoning

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Virulence factor

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Hemotoxin

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Aspergillus heterothallicus

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emeheterone, emesterones A & B, 5’-hydroxyaveranthin, stellatin, and sterigmatocystin. A. heterothallicus has been cultivated on both Czapek yeast extract...

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