Classification Term: 2055

Sterigmatocystins (ontology term: CHEMONTID:0001817)

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." [ISBN-13:978-0849349041]

found 7 associated metabolites at class metabolite taxonomy ontology rank level.

Ancestor: Phenylpropanoids and polyketides

Child Taxonomies: There is no child term of current ontology term.

Sterigmatocystin

15-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

C18H12O6 (324.0634)


Sterigmatocystin 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 D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins CONFIDENCE Reference Standard (Level 1); INTERNAL_ID 2320

   

De-O-methylsterigmatocystin

11,15-dihydroxy-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

C17H10O6 (310.0477)


De-O-methylsterigmatocystin is a mycotoxin of Aspergillus versicolor. Mycotoxin of Aspergillus versicolor

   

O-Methylsterigmatocystin

11,15-dimethoxy-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

C19H14O6 (338.079)


O-Methylsterigmatocystin is a mycotoxin of Aspergillus flavu D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins

   

De-O-methyldihydrosterigmatocystin

11,15-dihydroxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14,16,18-hexaen-13-one

C17H12O6 (312.0634)


De-O-methyldihydrosterigmatocystin is a mycotoxin produced by Aspergillus versicolor. Mycotoxin production by Aspergillus versicolor.

   

Dihydrosterigmatocystin

15-hydroxy-11-methoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14,16,18-hexaen-13-one

C18H14O6 (326.079)


Dihydrosterigmatocystin is a mycotoxin of Aspergillus versicolo

   

5,6-Dimethoxysterigmatocystin

15-hydroxy-11,17,18-trimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),4,10,14(19),15,17-heptaen-13-one

C20H16O8 (384.0845)


5,6-Dimethoxysterigmatocystin is a mycotoxin produced by Aspergillus multicolo D009676 - Noxae > D011042 - Poisons > D009183 - Mycotoxins

   

Dihydrohydroxy-O-methylsterigmatocystin

5-hydroxy-11,15-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.0²,⁹.0³,⁷.0¹⁴,¹⁹]icosa-1(12),2(9),10,14,16,18-hexaen-13-one

C19H16O7 (356.0896)


Dihydrohydroxy-O-methylsterigmatocystin is a mycotoxin produced by Aspergillus parasiticus. Mycotoxin production by Aspergillus parasiticus.