Shamixanthone

Last updated
Shamixanthone
Shamixanthone.svg
Names
Preferred IUPAC name
(1R,2S)-1,11-Dihydroxy-5-methyl-8-(3-methylbut-2-en-1-yl)-2-(prop-1-en-2-yl)-2,3-dihydropyrano[3,2-a]xanthene-12(1H)-one
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
  • InChI=1S/C25H26O5/c1-12(2)6-7-15-8-9-17(26)19-23(28)20-18(30-25(15)19)10-14(5)24-21(20)22(27)16(11-29-24)13(3)4/h6,8-10,16,22,26-27H,3,7,11H2,1-2,4-5H3/t16-,22-/m0/s1
    Key: MXGMZMKTWCNKRS-AOMKIAJQSA-N
  • InChI=1/C25H26O5/c1-12(2)6-7-15-8-9-17(26)19-23(28)20-18(30-25(15)19)10-14(5)24-21(20)22(27)16(11-29-24)13(3)4/h6,8-10,16,22,26-27H,3,7,11H2,1-2,4-5H3/t16-,22-/m0/s1
    Key: MXGMZMKTWCNKRS-AOMKIAJQBQ
  • C/C(C)=C\Cc4ccc(O)c3C(=O)c2c(cc(C)c1OC[C@H]([C@H](O)c12)C(C)=C)Oc34
Properties
C25H26O5
Molar mass 406.478 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Shamixanthone is a chemical compound, classified as a prenylated xanthone, that has been isolated from several species of Aspergillus , including Aspergillus turkensis . [1]

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Aspergillus stellatus is a species of fungus in the genus Aspergillus. It is from the Nidulantes section. The species was first described in 1934. It has been isolated from soil in Panama and seeds in India. It has been reported in human infections. It has been reported to produce aflatoxin B1, ajamxanthone, shamixanthone, tajixanthone, tajixanthone hydrate, tajixanthone methanoate, 19-O-methyl-22- methoxypre-shamixanthone, pre-shamixanthone, 15- acetyltajixanthone hydrate, andibenin A, andibenin B, andibenin C, andelesin A, andelesin B, anditomin, arugosin A, arugosin B, arugosin D, asperthecin, astellatol, asteltoxin, desferritriacetylfusigen, dihydroterrein, emervaridione, varioxiranediol, epiisoshamixanthone, ophiobolin C, ophiobolin G, ophiobolin H, ophiobolin K, evariquinone, 2-Furanoic acid, islandicin, isoemericellin, kojic acid, 2-Methoxy-6-(3,4-dihydroxy-hepta-1,5-dienyl)benzyl alcohol, najamxanthone, radixanthone, shahenxanthone, penicillin G, shimalactone A, siderin, stellatic acid, stellatin, stromemycin, terrein, variecoacetal A, variecoacetal B, variecolactone, variecolin, varioxirane, varixanthone, varitriol, and varioxranol A-G.

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References

  1. Simpson, Thomas J. (2012). "Genetic and Biosynthetic Studies of the Fungal Prenylated Xanthone Shamixanthone and Related Metabolites in Aspergillus spp. Revisited". ChemBioChem. 13 (11): 1680–1688. doi:10.1002/cbic.201200014. PMID   22730213. S2CID   25478280.