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Staphyloxanthin

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EntityQ7600428· pop 9· linked from 5 articles

Staphyloxanthin

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Staphyloxanthin is a carotenoid pigment that is produced by some strains of Staphylococcus aureus, and is responsible for the characteristic golden color that gives S. aureus its species name. Staphyloxanthin also acts as a virulence factor. It has an antioxidant action that helps the microbe evade death by reactive oxygen species produced by the host immune system. left|thumb|250x250px|The pigment staphyloxanthin gave the bacteria [[Staphylococcus aureus a yellow color.]] When comparing a normal strain of S. aureus with a strain modified to lack staphyloxanthin, the wildtype pigmented strain

In the Vinony graph

Vinony's link graph records 5 inbound references to Staphyloxanthin, and connects out to digital object identifier, cholesterol and International Standard Serial Number.

It sits within the topics Carotenoids, Chembox image size set and Glucosides.

Vinony links it to 9 Wikipedia language editions.

Chemical data

Formula
C51H78O8
Molecular weight
819.2 g/mol
IUPAC name
[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(12-methyltetradecanoyloxymethyl)oxan-2-yl] (2E,4E,6E,8E,10E,12E,14E,16E,18E)-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate
SMILES
CCC(C)CCCCCCCCCCC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC(=O)/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/CCC=C(C)C)/C)/C)/C)O)O)O
InChIKey
PDOUICUKTQRPHO-MENSNCDRSA-N
XLogP
15.2
Polar surface area
123 Ų
H-bond donors
3
H-bond acceptors
8
Formal charge
0

via PubChem

Wikidata facts

Mass
818.569669456
Show 4 more facts
chemical formula
C₅₁H₇₈O₈
isomeric SMILES
CCC(C)CCCCCCCCCCC(=O)OC[C@H]1O[C@@H](OC(=O)/C(C)=C/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(\C)CCC=C(C)C)[C@H](O)[C@@H](O)[C@@H]1O
canonical SMILES
O=C(OC1OC(COC(=O)CCCCCCCCCCC(C)CC)C(O)C(O)C1O)C(=CC=CC(=CC=CC(=CC=CC=C(C=CC=C(C)CCC=C(C)C)C)C)C)C
found in taxon
Staphylococcus aureus
Sources (2)

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Encyclopedic overview

2 sections
Contents
  • References
  • External links

Staphyloxanthin is a carotenoid pigment that is produced by some strains of Staphylococcus aureus, and is responsible for the characteristic golden color that gives S. aureus its species name. Staphyloxanthin also acts as a virulence factor. It has an antioxidant action that helps the microbe evade death by reactive oxygen species produced by the host immune system. left|thumb|250x250px|The pigment staphyloxanthin gave the bacteria [[Staphylococcus aureus a yellow color.]] When comparing a normal strain of S. aureus with a strain modified to lack staphyloxanthin, the wildtype pigmented strain was more likely to survive incubation with an oxidizing chemical such as hydrogen peroxide than the mutant strain was. Colonies of the two strains were also exposed to human neutrophils. The mutant colonies quickly succumbed while many of the pigmented colonies survived. Wounds on mice were inoculated with the two strains. The pigmented strains created lingering abscesses. Wounds with the unpigmented strains healed quickly. These tests suggest that the staphyloxanthin may be key to the ability of S. aureus to survive immune system attacks.

Drugs designed to inhibit the bacterium's production of the staphyloxanthin may weaken it and renew its susceptibility to antibiotics. In fact, because of similarities in the pathways for biosynthesis of staphyloxanthin and human cholesterol, a drug developed in the context of cholesterol-lowering therapy was shown to block S. aureus pigmentation and disease progression in a mouse infection model.

Excerpted from Wikipedia’s “Staphyloxanthin” article, available under the CC BY-SA 4.0 licence.

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