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Staphyloxanthin
Sign in to saveStaphyloxanthin 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)
via Wikidata · CC0
~2 min read
Encyclopedic overview
2 sectionsContents
- 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.