Aureoquinone

Aureoquinone

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Category Antibiotics
Catalog number BBF-00227
CAS
Molecular Weight 250.20
Molecular Formula C12H10O6

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Description

Aureoquinone is produced by the strain of Aureobasidium sp. The IC50 (μg/mL) for inhibiting the activity of protease, including trypsin, papain, thermophilic protease, collagenase and pound-protease are 11.4、14.5、17.8、7.1、and 8.7 respectively.

Specification

Synonyms 2,5,7,8-tetrahydroxy-3,6-dimethylnaphthalene-1,4-dione
IUPAC Name 4,5,7,8-tetrahydroxy-3,6-dimethylnaphthalene-1,2-dione
Canonical SMILES CC1=C(C2=C(C(=C1O)O)C(=O)C(=O)C(=C2O)C)O
InChI InChI=1S/C12H10O6/c1-3-7(13)5-6(11(17)9(3)15)12(18)10(16)4(2)8(5)14/h13-15,17H,1-2H3
InChI Key DWESCCREDKEKQP-UHFFFAOYSA-N

Properties

Appearance Brown Acicular Crystalline
Melting Point 268-269 °C

Reference Reading

1. Basidiomycete metabolites attenuate virulence properties of Candida albicans in vitro
Barbara Falkensammer, Lisa Pleyer, Sigrun Ressler, Albrecht Berg, Margarethe Borg-von Zepelin, Markus Nagl, Cornelia Lass-Flörl, Cornelia Speth, Manfred P Dierich, Reinhard Würzner Mycoses. 2008 Nov;51(6):505-14. doi: 10.1111/j.1439-0507.2008.01515.x. Epub 2008 Apr 16.
Secreted aspartic proteases (Saps) represent an important virulence factor facilitating fungal adherence. Several protease inhibitors (PIs), including HIV PIs, have been shown to reduce Candida adhesion. The aim of this study was to ascertain whether or not the recently discovered PIs Aureoquinone and Laccaridiones A and B, isolated from Basidiomycete cultures, or Bestatin, act as Sap-inhibitors and/or inhibitors of fungal adhesion. Drug effects on candidial Sap-production were determined by Sap-ELISA. Control tubes, in the absence of drug, served as positive controls, while tubes excluding both drug and proteinase induction medium were used as negative controls. Aureoquinone as well as Laccaridiones A and B, but not Bestatin, significantly inhibited Candida albicans adhesion to both epithelial and endothelial cells in a dose dependent manner and also reduced Sap-release (effects were not because of a direct interaction of the Basidiomycete metabolites with secreted Saps). Laccaridione B was consistently found to be the most effective PI tested. Interestingly, these drugs are neither fungistatic nor fungicidal at the concentrations applied. Laccaridione B may represent a promising novel type of antimycotic drug--targeting virulence factors without killing the yeast.
2. Concise formal total synthesis of hybocarpone and related naturally occurring naphthazarins
Christina L L Chai, John A Elix, Felicity K E Moore J Org Chem. 2006 Feb 3;71(3):992-1001. doi: 10.1021/jo0519561.
A concise formal total synthesis of the cytotoxic bisnaphthazarin derivative hybocarpone has been completed through the development of routes to the synthetic precursor, 3-ethyl-2-hydroxy-5,7,8-trimethoxy-6-methyl-1,4-naphthoquinone. The oxidation of 3-ethyl-1,2,4,5,7,8-hexamethoxy-6-methylnaphthalene under Rapoport conditions gave 3-ethyl-2-hydroxy-5,7,8-trimethoxy-6-methyl-1,4-naphthoquinone in modest yields after basic hydrolysis. In addition, treatment of 3-ethyl-1,2,4,5,7,8-hexamethoxy-6-methylnaphthalene with boron tribromide provided access to the naturally occurring naphthazarin, boryquinone. The analogous oxidative demethylation of 3,6-dimethyl-1,2,4,5,7,8-hexamethoxynaphthalene and 3-ethyl-1,2,4,5,7,8-hexamethoxynaphthalene resulted in the synthesis of 2,5,7,8-tetrahydroxy-3,6-dimethyl-1,4-naphthoquinone (aureoquinone) and 3-ethyl-2,5,7,8-tetrahydroxy-1,4-naphthoquinone, respectively. An alternative selective synthetic route to 3-ethyl-2-hydroxy-5,7,8-trimethoxy-6-methyl-1,4-naphthoquinone was also developed utilizing an intramolecular Claisen condensation of methyl 2-butyryl-3,5,6-trimethoxy-4-methylphenylacetate with concomitant in situ aerial oxidation.

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Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
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