Disease relevance of p-cymene

• p-Cymene pathway in Pseudomonas putida: selective enrichment of defective mutants by using halogenated substrate analogs [1].
• Several compounds structurally related to l-carvone, including limonene, p-cymene, and isoprene, also induced cometabolism of PCBs by Arthrobacter sp. strain B1B [2].
• The MICs and MBCs of carvacrol, thymol, p-cymene, and gamma-terpinene against a strain of E. coli O157: H7 phage type 34 isolated from bovine feces were determined by microdilution assay [3].
• Enhanced fumigant toxicity of p-cymene against Frankliniella occidentalis by simultaneous application of elevated levels of carbon dioxide [4].
• The bioreporter, designated Pseudomonas putida UT93, contains a Vibrio fischeri luxCDABE gene fused to a p-cymene/p-cumate-inducible promoter derived from the P. putida F1 cym operon [5].

High impact information on p-cymene

• Strain PpG777 resembles the parental culture in growth on linalool as a source of carbon and slight growth on p-cymene, whereas PaG158 grows well on p-cymene, but not on linalool or other terpenes tested, and has a P. aeruginosa phenotype [6].
• Curing studies indicate that linalool metabolism is controlled by an extrachromosomal element whose loss forms a stable strain PaG158 with the p-cymene growth and P. aeruginosa phenotype characters [6].
• Plasmid control of the Pseudomonas aeruginosa and Pseudomonas putida phenotypes and of linalool and p-cymene oxidation [6].
• It was confirmed that 2,3-dihydroxy-p-cumate is a substrate for ring cleavage in Pseudomonas putida PL-W after growth with p-cymene or p-cumate [7].
• This was confirmed with a mutant of P. putida PL-RF-1 that was unable to grow with p-cymene (or p-cumate) but was able to oxidize both compounds AND 2,3-DIHYDROXY-P-CUMATE TO A YELLOW INTERMEDIATE (LAMBDA MAX, 345 NM) WITHOUT DECARBOXYLATION [7].

Chemical compound and disease context of p-cymene

• Pseudomonas putida F1 can assimilate benzene, toluene and ethylbenzene using the toluene degradation pathway, and can also utilize p-cymene via p-cumate using the p-cymene and p-cumate catabolic pathways [8].
• p-Cymene monooxygenase (CMO) from Pseudomonas putida F1 consists of a hydroxylase (CymA1) and a reductase component (CymA2) which initiate pcymene (p-isopropyltoluene) catabolism by oxidation of the methyl group to p-isopropylbenzyl alcohol (p-cumic alcohol) [9].
• The most abundant were naphthalene, 1-methyl-, 3-heptanone, methylcyclododecane, heptane, 2,2,4,6,6-pentamethyl-, benzene, 1-methyl-4-(1-methylethyl)-, and cyclohexane, 1,4-dimethyl-. Breath VOCs were assayed by GC/MS in 42 patients hospitalized for suspicion of pulmonary tuberculosis and in 59 healthy controls [10].

Biological context of p-cymene

• The biotransformation of (+)-, (-)-, and (+-)-alpha-pinenes, (-)-beta-pinene (nopinene), (-)-cis-pinane, (+)-3-carene, (-)-cis-carane, myrcene, and p-cymene in rabbits was investigated [11].
• Microsomal metabolism and enzyme kinetics of the terpene p-cymene in the common brushtail possum (Trichosurus vulpecula), koala (Phascolarctos cinereus) and rat [12].
• Four weeks' inhalation exposure of rats to p-cymene affects regional and synaptosomal neurochemistry [13].
• The entire array of gene clusters responsible for the catabolism of toluene and p-cymene/p-cumate has been cloned in a cosmid vector, pLAFR3, and were named pEK6 and pEK27, respectively [14].

Anatomical context of p-cymene

• The oils of oregano plants were strongly characterized by p-cymene (16.8-24.9%), gamma-terpinene (16.8-24.9%), thymol (8.4-36.0%), and carvacrol (1.1-29.7%), a thymol chemotype for Origanum floribundum and a alpha-terpineol chemotype for Thymus numidicus being described for the first time [15].
• The metabolism of p-cymene by liver microsomes from the possum, koala and rat (an animal whose diet is not terpene-rich) was examined [12].

Associations of p-cymene with other chemical compounds

• RESULTS: Of seven patients reactive to the 1% melaleuca oil solution, six patients also reacted to limonene, five to alpha-terpinene and aromadendrene, 2 to terpinen-4-ol, and one each to p-cymene and alpha-phellandrene. d-Carvone, an autooxidative derivative of limonene, caused no reactions among the seven patients [16].
• Antifungal activities of the thyme essential oil, which contains p-cymene (36.5%), thymol (33.0%) and 1,8-cineole (11.3%) as main components, and pure thymol were determined by the dilution method and exposure to vaporous phase of the oil [17].
• Essential oils were identified by gas chromatography: (+)-limonene (21%), p-cymene (1.7%), estragol (3.2%), beta-ocimene (1.4%), and thymol (2.6%) [18].
• The essential oil compositions of three species (Helichrysum dasyanthum, Helichrysum excisum and Helichrysum petiolare) were dominated by the presence of monoterpenes such as alpha-pinene, 1,8-cineole and p-cymene [19].

Gene context of p-cymene

• Treatment of mice with the other volatile oil constituents, p-cymene or alpha-pinene did not induce any changes in the serum ALT measured [20].

Analytical, diagnostic and therapeutic context of p-cymene

• 2,3-Dihydroxy-p-cumate-3,4-dioxygenase, an enzyme involved in the catabolism of p-cymene, was purified to homogeneity from Bacillus species by affinity chromatography [21].

References