O-Methylsterigmatocystin
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| Category | Mycotoxins |
| Catalog number | BBF-04354 |
| CAS | 17878-69-2 |
| Molecular Weight | 338.31 |
| Molecular Formula | C19H14O6 |
| Purity | >95% by HPLC |
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Description
A xanthone isolated from several species of aspergillus including A. flavus, A. parasiticus, A. versicolor and B. piluliferum. It is a carcinogenic precursor of aflatoxin, and structurally related to the aflatoxins.
Specification
| Synonyms | OMST; 8-O-Methylsterigmatocystin; O-Methyl sterigmatocystin; 7-O-Methylsterigmatocystin; 7H-Furo(3',2':4,5)furo(2,3-c)xanthen-7-one, 3a,12c-dihydro-6,8-dimethoxy-, (3aR-cis)-; Sterigmatocystin, O-methyl-; 3aR,12cS-dihydro-6,8-dimethoxy-7H-furo[3',2':4,5]furo[2,3-c]xanthen-7-one |
| Storage | Store at -20°C |
| IUPAC Name | (3S,7R)-11,15-dimethoxy-6,8,20-trioxapentacyclo[10.8.0.02,9.03,7.014,19]icosa-1,4,9,11,14(19),15,17-heptaen-13-one |
| Canonical SMILES | COC1=CC=CC2=C1C(=O)C3=C(C=C4C(=C3O2)C5C=COC5O4)OC |
| InChI | InChI=1S/C19H14O6/c1-21-10-4-3-5-11-15(10)17(20)16-12(22-2)8-13-14(18(16)24-11)9-6-7-23-19(9)25-13/h3-9,19H,1-2H3/t9-,19+/m0/s1 |
| InChI Key | JKUJKKGMOZDDJV-ZRNGKTOUSA-N |
| Source | Chaetomium sp. |
Properties
| Appearance | Pale Yellow Solid |
| Boiling Point | 564.7±50.0°C (Predicted) |
| Melting Point | 265°C |
| Density | 1.407±0.06 g/cm3 (Predicted) |
| Solubility | Soluble in DMF, DMSO; Moderately soluble in Methanol, Ethanol; Poorly soluble in Water |
Reference Reading
1.Conversion of 11-hydroxy-O-methylsterigmatocystin to aflatoxin G1 in Aspergillus parasiticus.
Zeng H1, Hatabayashi H, Nakagawa H, Cai J, Suzuki R, Sakuno E, Tanaka T, Ito Y, Ehrlich KC, Nakajima H, Yabe K. Appl Microbiol Biotechnol. 2011 Apr;90(2):635-50. doi: 10.1007/s00253-010-2999-z. Epub 2010 Dec 14.
In aflatoxin biosynthesis, aflatoxins G(1) (AFG(1)) and B(1) (AFB(1)) are independently produced from a common precursor, O-methylsterigmatocystin (OMST). Recently, 11-hydroxy-O-methylsterigmatocystin (HOMST) was suggested to be a later precursor involved in the conversion of OMST to AFB(1), and conversion of HOMST to AFB(1) was catalyzed by OrdA enzyme. However, the involvement of HOMST in AFG(1) formation has not been determined. In this work, HOMST was prepared by incubating OrdA-expressing yeast with OMST. Feeding Aspergillus parasiticus with HOMST allowed production of AFG(1) as well as AFB(1). In cell-free systems, HOMST was converted to AFG(1) when the microsomal fraction, the cytosolic fraction from A. parasiticus, and yeast expressing A. parasiticus OrdA were added. These results demonstrated (1) HOMST is produced from OMST by OrdA, (2) HOMST is a precursor of AFG(1) as well as AFB(1), and (3) three enzymes, OrdA, CypA, and NadA, and possibly other unknown enzymes are involved in conversion of HOMST to AFG(1).
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
