Pigments of Staphylococcus aureus, a series of triterpenoid carotenoids

Abstract

The pigments of Staphylococcus aureus were isolated and purified, and their chemical structures were determined. All of the 17 compounds identified were triterpenoid carotenoids possessing a C3o chain instead of the C4o carotenoid structure found in most other organisms. The main pigment, staphyloxanthin, was shown to be aD -glucopyranosyl 1-0-(4,4'-diaponeurosporen-4-oate) 6-0-(12methyltetradecanoate), in which glucose is esterified with both a triterpenoid carotenoid carboxylic acid and a C15 fatty acid. It is accompanied by isomers containing other hexoses and homologs containing C17 fatty acids. The carotenes 4,4'-diapophytoene, 4,4'-diapophytofluene, 4-4'-diapo-±-carotene, 4,4'-diapo-7,8,11,12-tetrahydrolycopene, and 4,4'-diaponeurosporene and the xanthophylls 4,4'-diaponeurosporenal, 4,4'-diaponeurosporenoic acid, and glucosyl diaponeurosporenoate were also identified, together with some of their isomers or breakdown products. The symmetrical 4,4'-diapostructure was adopted for these triterpenoid carotenoids, but an alternative unsymmetrical 8'-apostructure could not be excluded.

Potential action of copper surfaces on meticillin-resistant Staphylococcus aureus

“…The initial site of copper toxicity for MRSA is suggested to be the cell membrane with copper acting as a catalyst in the formation of reactive oxygen species which in turn catalyses peroxidation of membrane lipids (Ohsumi et al 1988). In addition, research in yeast cells suggests that copper ions caused a selective change in the permeability barrier of the membrane, which induced a significant leakage of ions and low molecular weight substances from the cell (Marshall and Wilmoth 1981). However, our findings suggest no direct effect on the structure of the cell membrane of the Gram-positive MRSA with epifluorescence images showing only small amounts of uptake of the fluorophore propidium iodide, which because of its molecular weight can only cross disrupted membranes to intercalate into the DNA double helix.…”

Biosynthesis of a novel C30 carotenoid in Bacillus firmus isolates

“…C 30 carotenoids are another minor group. They are found in unrelated genera and species like Methylobacterium rhodium (formerly Pseudomonas rhodos) (Kleinig et al 1979), Methylomonas (Tao et al 2005), Staphylococcus aureus (Marshall and Wilmoth 1981), heliobacteria (Takaichi et al 2003), Rubritella squalenifaciens (Shindo et al 2007(Shindo et al , 2008a, Planococcus maritimus (Shindo et al 2008b) and Halobacillus halophilus (Köcher et al 2009). The C30 carotenoid products of bacterial pathways include staphyloxanthin (Pelz et al 2005) derived from diaponeurosporene, a methyl glucosyl apo-lycopenoate derivative (Osawa et al 2010), acylglycosyl monoesters (Shindo et al 2008a,b) or diacylglycosyl diesters both derived from 4,4′-diapolycopene (Shindo et al 2007).…”

Aerobic condition increases carotenoid production associated with oxidative stress tolerance inEnterococcus gilvus

“…A wide range of organisms, such as green plants, algae, fungi, and bacteria, can produce carotenoids (Nelis & De Leenheer, 1991). LAB belonging to Lactobacillus and Enterococcus, which comprise nonphotosynthetic bacteria, can produce the C 30 carotenoid 4,4'-diaponeurosporene (Taylor & Davies, 1974;Marshall & Wilmoth, 1981;Takaichi et al, 1997;Garrido-Fern andez et al, 2010). LAB have carotenoid biosynthesis genes, such as crtN and crtM, which are widely conserved in carotenoid-producing LAB.…”