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Revision as of 17:55, 9 January 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 464461804 of page Staphyloxanthin for the Chem/Drugbox validation project (updated: 'CASNo').  Latest revision as of 07:20, 3 July 2023 edit Citation bot (talk | contribs)Bots5,391,856 edits Add: bibcode. | Use this bot. Report bugs. | Suggested by Spinixster | Category:Glucosides | #UCB_Category 7/60 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{chembox {{chembox
| Verifiedfields = changed
⚫ | verifiedrevid = 449645463
| Watchedfields = changed
⚫ | verifiedrevid = 470470573
| Name = Staphyloxanthin | Name = Staphyloxanthin
| ImageFile = Staphyloxanthin.svg | ImageFile = Staphyloxanthin.svg
| ImageSize = 350px | ImageSize = 250px
| ImageName = Chemical structure of staphyloxanthin | ImageName = Chemical structure of staphyloxanthin
| ImageAlt = Chemical structure of staphyloxanthin | ImageAlt = Chemical structure of staphyloxanthin
| IUPACName = <nowiki> [(2S,3R,4S,5S,6R)-3,4, | IUPACName = [(2''S'',3''R'',4''S'',5''S'',6''R'')-3,4,
5-trihydroxy-6-oxymethyl]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</nowiki> 5-Trihydroxy-6-<nowiki>oxymethyl]oxan-2-yl] (2''E'',4''E'',6''E'',8''E'',10''E'',12''E'',14''E'',16''E'',18''E'')-2,6,10,15,19,23-hexamethyltetracosa-2,4,6,8,10,12,14,16,18,22-decaenoate
| OtherNames = <!-- <br> --> | OtherNames =
|Section1= {{Chembox Identifiers |Section1={{Chembox Identifiers
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4947803 | ChemSpiderID = 65323059
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 71690
| InChI1 = 1/C51H78O8/c1-10-39(4)25-16-14-12-11-13-15-17-33-44(36-52)51(9,35-23-32-43(8)49(57)59-50-48(56)47(55)46(54)45(37-53)58-50)34-19-18-26-40(5)28-21-30-42(7)31-22-29-41(6)27-20-24-38(2)3/h17-19,21-24,26,28-33,35-36,39,44-48,50,53-56H,10-16,20,25,27,34,37H2,1-9H3/b19-18+,28-21+,31-22+,33-17-,35-23+,40-26+,41-29+,42-30+,43-32+/t39?,44?,45-,46-,47+,48-,50-,51?/m1/s1 | InChI1 = 1/C51H78O8/c1-10-39(4)25-16-14-12-11-13-15-17-33-44(36-52)51(9,35-23-32-43(8)49(57)59-50-48(56)47(55)46(54)45(37-53)58-50)34-19-18-26-40(5)28-21-30-42(7)31-22-29-41(6)27-20-24-38(2)3/h17-19,21-24,26,28-33,35-36,39,44-48,50,53-56H,10-16,20,25,27,34,37H2,1-9H3/b19-18+,28-21+,31-22+,33-17-,35-23+,40-26+,41-29+,42-30+,43-32+/t39?,44?,45-,46-,47+,48-,50-,51?/m1/s1
| InChIKey1 = ZGBLADNGFNFPBV-OQMOJWPEBF | InChIKey1 = ZGBLADNGFNFPBV-OQMOJWPEBF
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = ZGBLADNGFNFPBV-OQMOJWPESA-N | StdInChIKey = ZGBLADNGFNFPBV-OQMOJWPESA-N
| CASNo = <!-- blanked - oldvalue: 71869-01-7 --> | CASNo = 71869-01-7
| CASNo_Ref = {{cascite|correct|??}}= | CASNo_Ref = {{cascite|changed|??}}
| CASOther = | CASNoOther =
| PubChem = 24892781 | PubChem = 56928085
| SMILES = O=C(O1O((O)(O)1O)CO)\C(=C\C=C\C(C)(C\C=C\C=C(\C=C\C=C(\C=C\C=C(/C)CC\C=C(/C)C)C)C)C(\C=C/CCCCCCCC(C)CC)C=O)C | SMILES = O=C(O1O((O)(O)1O)CO)\C(=C\C=C\C(C)(C\C=C\C=C(\C=C\C=C(\C=C\C=C(/C)CC\C=C(/C)C)C)C)C(\C=C/CCCCCCCC(C)CC)C=O)C
| InChI = | InChI =
| MeSHName = | MeSHName =
}} }}
|Section2= {{Chembox Properties |Section2={{Chembox Properties
| C=51
| Formula = C<sub>51</sub>H<sub>78</sub>O<sub>8</sub>
| H=78
| MolarMass = 819.16 g/mol
| O=8
| ExactMass = 818.569669 u
| Appearance = | Appearance =
| Density = | Density =
| MeltingPt = <!-- °C --> | MeltingPt =
| BoilingPt = <!-- °C --> | BoilingPt =
| Solubility = | Solubility =
}} }}
}} }}

'''Staphyloxanthin''' is a ] ] that is produced by some strains of '']'', 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 ] action that helps the microbe evade death by ] produced by the host immune system.<ref name="staphylotoxin">{{cite journal |vauthors=Clauditz A, Resch A, Wieland KP, Peschel A, Götz F |title=Staphyloxanthin plays a role in the fitness of Staphylococcus aureus and its ability to cope with oxidative stress |journal=Infection and Immunity |volume=74 |issue=8 |pages=4950–3 |date=August 2006 |pmid=16861688 |pmc=1539600 |doi=10.1128/IAI.00204-06 }}</ref>
] staphyloxanthin gave the bacteria '']'' 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 ] than the mutant strain was. Colonies of the two strains were also exposed to human ]. 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 ]es. 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.<ref name="JExpMed2005-Liu">{{cite journal |vauthors=Liu GY, Essex A, Buchanan JT, Datta V, Hoffman HM, Bastian JF, Fierer J, Nizet V | title=Staphylococcus aureus golden pigment impairs neutrophil killing and promotes virulence through its antioxidant activity | journal=J Exp Med | year=2005 | pages=209–15 | volume=202 | issue=2 | pmid=16009720 | doi=10.1084/jem.20050846 | pmc=2213009}}</ref> In fact, because of similarities in the pathways for biosynthesis of staphyloxanthin and human ], a drug developed in the context of cholesterol-lowering therapy was shown to block ''S. aureus'' pigmentation and disease progression in a ].<ref name="Science2008-Liu">{{cite journal |vauthors=Liu CI, Liu GY, Song Y, Yin F, Hensler ME, Jeng WY, Nizet V, Wang AH, Oldfield E | title=A cholesterol biosynthesis inhibitor blocks Staphylococcus aureus virulence | journal=Science | year=2008 | pages=391–94 | volume=319| pmid=18276850 | doi=10.1126/science.1153018 | issue=5868 | pmc=2747771| bibcode=2008Sci...319.1391L }}</ref>

==References==
{{reflist}}

==External links==
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