Vioxanthin

Vioxanthin is a mycotoxin that was first isolated from the pathogenic fungus Trichophyton violaceum and characterized in 1966.[1] It is a pigment with a

Vioxanthin
Not to be confused with violaxanthin.
Vioxanthin
Names
IUPAC name
(3R)-8-[(3R)-9,10-Dihydroxy-7-methoxy-3-methyl-1-oxo-3,4-dihydrobenzo[g]isochromen-8-yl]-9,10-dihydroxy-7-methoxy-3-methyl-3,4-dihydrobenzo[g]isochromen-1-one
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C30H26O10/c1-11-5-13-7-15-9-17(37-3)23(27(33)19(15)25(31)21(13)29(35)39-11)24-18(38-4)10-16-8-14-6-12(2)40-30(36)22(14)26(32)20(16)28(24)34/h7-12,31-34H,5-6H2,1-4H3/t11-,12-/m1/s1
    Key: CJKYODJTBJDEJI-VXGBXAGGSA-N
  • C[C@@H]1CC2=C(C(=C3C(=C2)C=C(C(=C3O)C4=C(C5=C(C6=C(C[C@H](OC6=O)C)C=C5C=C4OC)O)O)OC)O)C(=O)O1
Properties
C30H26O10
Molar mass 546.528 g·mol−1
Appearance Brownish-yellow solid
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Vioxanthin is a mycotoxin that was first isolated from the pathogenic fungus Trichophyton violaceum and characterized in 1966.[1] It is a pigment with a brownish-yellow color.[1] It has since been found to be a constituent of a variety of other fungi including those in the genus Penicillium[2] and Aspergillus.[3] The detection of vioxanthin in food products has been used as evidence of contamination with these fungi.[4]

A laboratory synthesis of vioxanthin has been reported.[5]

References

  1. ^ a b Blank, F.; Ng, A. S.; Just, G. (1966). "Metabolites of Pathogenic Fungi: V. Isolation and Tentative Structures of Vioxanthin and Viopurpurin, Two Colored Metabolites of Trichophyton Violaceum". Canadian Journal of Chemistry. 44 (23): 2873–2879. doi:10.1139/v66-427.
  2. ^ Scudamore, K. A.; Clarke, J. H.; Hetmanski, M. T. (1993). "Isolation of Penicillium strains producing ochratoxin A, citrinin, xanthomegnin, viomellein and vioxanthin from stored cereal grains". Letters in Applied Microbiology. 17 (2): 82–87. doi:10.1111/j.1472-765X.1993.tb00377.x.
  3. ^ Stack, Michael E.; Mislivec, Philip B.; Denizel, Turgut; Gibson, Regina; Pohland, Albert E. (1983). "Ochratoxins a and B, Xanthomegnin, Viomellein and Vioxanthin Production by Isolates of Aspergillus ochraceus from Green Coffee Beans". Journal of Food Protection. 46 (11): 965–968. doi:10.4315/0362-028X-46.11.965. PMID 30921851.
  4. ^ Scudamore, Keith A.; Atkin, Pauline M.; Buckle, Anthony E. (1986). "Natural occurrence of the naphthoquinone mycotoxins, xanthomegnin, viomellein and vioxanthin in cereals and animal feldstuffs". Journal of Stored Products Research. 22 (2): 81–84. doi:10.1016/0022-474X(86)90023-8.
  5. ^ Bode, Silke E.; Drochner, Daniel; Müller, Michael (2007). "Synthesis, Biosynthesis, and Absolute Configuration of Vioxanthin". Angewandte Chemie International Edition. 46 (31): 5916–5920. Bibcode:2007ACIE...46.5916B. doi:10.1002/anie.200701014. PMID 17607794.

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