CAS 71869-01-7 | Staphyloxanthin

Product introduction & applications:

   Staphyloxanthin is a C30 carotenoid pigment produced by Staphylococcus aureus.

    Structural features: It has a long hydrophobic carbon chain (about 30 carbon atoms) that can be embedded into the lipid bilayer of bacterial cell membranes to form stable anchoring
Spectral characteristics: The characteristic peaks in Raman spectroscopy are located at 1161 cm ⁻¹ (C-C single bond vibration) and 1525 cm ⁻¹ (C=C double bond vibration)
Biological functions:
Antioxidant defense: By neutralizing the reactive oxygen species (ROS) produced by host immune cells (such as neutrophils), bacteria's resistance to oxidative damage is enhanced.
Toxicity factor: It is a virulence factor of Staphylococcus aureus, and the absence of this pigment significantly reduces its pathogenicity
Color source: endows colonies with a typical golden yellow color, which is also the origin of the name "Staphylococcus aureus"
Targeted therapy strategy:
Blue light photodegradation: Blue light with a wavelength of 450-470 nm can specifically degrade staphylococcin, destroying its "golden armor" and making bacteria more easily killed by oxidants such as hydrogen peroxide.
Natural inhibitors:
Eugenol can inhibit 79.5-84.2% of staphylococcal flavin synthesis at a concentration of 300 μ g/mL without affecting bacterial growth.
Bavachinin, a dihydroflavonoid methyl ether from Fructus Psorale, also showed inhibitory effects on this pigment in MRSA.
New antibacterial drugs, such as BCP compounds (such as 31f, 44a), can achieve potent anti MRSA activity through a multi-target mechanism, including inhibition of staphylococcal flavin synthesis.

Synonyms:

[(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)Tetrahydropyran-2-Yl] (2E,4E,8E,10E,12E,14E,16E,18E)-6-[(Z)-1-Formyl-11-Methyl-Tridec-2-Enyl]-2,6,11,15,19,23-Hexamethyl-Tetracosa-2,4,8,10,12,14,16,18,22-Nonaenoate

Staphyloxanthin

(2E,4E,8E,10E,12E,14E,16E,18E)-6-[(Z)-1-Formyl-11-Methyltridec-2-Enyl]-2,6,11,15,19,23-Hexamethyltetracosa-2,4,8,10,12,14,16,18,22-Nonaenoic Acid [(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-(Hydroxymethyl)-2-Tetrahydropyranyl] Ester

C₅₁H₇₈O₈

71869-01-7

(2E,4E,8E,10E,12E,14E,16E,18E)-6-[(Z)-1-Formyl-11-Methyl-Tridec-2-Enyl]-2,6,11,15,19,23-Hexamethyl-Tetracosa-2,4,8,10,12,14,16,18,22-Nonaenoic Acid [(2R,3R,4S,5S,6R)-3,4,5-Trihydroxy-6-Methylol-Tetrahydropyran-2-Yl] Ester

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