Disease relevance of cineole

• Postulating the native E. coli flavodoxin/flavodoxin reductase system might mimic the natural redox partners of P450(cin), it was expressed in E. coli in the presence of cineole 1 [1].
• We report here a novel cytochrome P450 (P450(cin), CYP176A1) purified from a strain of Citrobacter braakii that is capable of using cineole 1 as its sole source of carbon and energy [1].
• Compatible interactions of Pseudomonas syringae DC3000 and Diuraphis noxia with Arabidopsis roots resulted in the rapid release of 1,8-cineole, a monoterpene that has not been previously reported in Arabidopsis [2].
• Mutagenicity testing (+/-)-camphor, 1,8-cineole, citral, citronellal, (-)-menthol and terpineol with the Salmonella/microsome assay [3].
• Specific induction of apoptosis by 1,8-cineole in two human leukemia cell lines, but not a in human stomach cancer cell line [4].

Psychiatry related information on cineole

• Blood levels of 1,8-cineole and locomotor activity of mice after inhalation and oral administration of rosemary oil [5].
• We investigated the influence of 1,8-cineole on the feeding behavior of two groups of sheep, one group dosed intravenously and the other intraruminally [6].

High impact information on cineole

• Monoterpene synthases from common sage (Salvia officinalis). cDNA isolation, characterization, and functional expression of (+)-sabinene synthase, 1,8-cineole synthase, and (+)-bornyl diphosphate synthase [7].
• Simulations further suggested that linalool and 1,8-cineole synthesis rates also decreased with decreasing G(V), possibly as the result of selective inhibition of various monoterpene synthases by stomata [8].
• 1,8-Cineole, representing 2% of TTO, reduced vascular changes induced by sensory neuropeptides released when the distal portion of a cut sciatic nerve was electrically stimulated [9].
• Loss of 260-nm-absorbing material occurred after treatment with concentrations equivalent to the MIC, particularly after treatment with 1,8-cineole and alpha-terpineol [10].
• All of the above compounds except cineole inhibited the growth of viral Ha-ras-transformed rat liver epithelial cells (WB-ras cells) at concentrations of 0.25-2.5 mM [11].

Chemical compound and disease context of cineole

• An At3g25820/At3g25830 cDNA was expressed in Escherichia coli, and the protein thus produced was shown to catalyze the formation of 10 volatile monoterpenes from geranyl diphosphate, with 1,8-cineole predominating [12].
• OBJECTIVES: Thirty isolates of Pseudomonas aeruginosa, 15 isolates of Pseudomonas putida and 11 isolates of Pseudomonas fluorescens were tested for susceptibility to tea tree oil (TTO), the essential oil of Melaleuca alternifolia, and the components terpinen-4-ol, alpha-terpineol, cineole, gamma-terpinene and rho-cymene [13].
• The test compound, 1,8-cineole (200 and 400 mg/kg) or vehicle (1 ml, 2% Tween 80) was instilled rectally, 24, and 2 h before (pre-treatment) or 2 and 24 h after (post-treatment) the induction of colitis by intracolonic administration of TNBS (0.25 ml of 25 mg of TNBS in 50% ethanol) [14].
• Using a TLC-bioautographic technique, the tea-tree oils, terpinen-4-ol, alpha-terpineol and alpha-pinene were found to be active against Staphylococcus aureus, Staph. epidermidis and Propionibacterium acnes whereas cineole was inactive against these organisms [15].
• The GC-MS analysis of the oil and its fractions revealed that the main components of the oil, e.g. camphor and eucalyptol, possessed appreciable activity against C. albicans and Clostridium perfringens [16].

Biological context of cineole

• Pharmacokinetic studies of the fragrance compound 1,8-cineol in humans during inhalation [17].
• The suction pipette technique was used to study simultaneously the odour-induced action potential and receptor current responses in frog olfactory receptor cells, which were exposed to the odour cineole for 1 s by rapidly exchanging the solution bathing their cilia [18].
• The present study was undertaken to investigate the pharmacokinetics of 1,8-cineol in human subjects during prolonged inhalation [17].
• METHODS: In experiment 1, we determined pharmacokinetic profiles of alcohol and of an aromatic substance (cineole) in amniotic fluid and maternal blood during late gestation [19].
• The effects of three terpene enhancers, (+)-limonene, nerolidol and 1,8-cineole, on stratum corneum structure were monitored [20].

Anatomical context of cineole

• In rats, pregenolone-16alpha-carbonitrile (PCN) and phenobarbital induced the 1,8-cineole 2-hydroxylation activities by liver microsomes [21].
• The data provide evidence of a key role for the mast cell in 1,8-cineole-induced hind paw oedema in the rat [22].
• Of the tested olfactory sensory neurons, 12% responded to the odorant cineole with an inward current [23].
• We tested three terpene compounds (carvone, limonene and 1,8-cineole) across the epithelium along the medial surface of the endoturbinate bones [24].
• Relaxant effects of the essential oil of Eucalyptus tereticornis and its main constituent 1,8-cineole on guinea-pig tracheal smooth muscle [25].

Associations of cineole with other chemical compounds

• 1. TRPM8 (CMR1) is a Ca(2+)-permeable channel, which can be activated by low temperatures, menthol, eucalyptol and icilin [26].
• The monoterpenes 1,8-cineole, thymol, geraniol, menthol and camphor strongly inhibited the root growth of Zea mays L. seedlings [27].
• The results obtained through gas chromatographic analysis allowed a second experiment in which we explicitly paired peak levels of cineole with peak levels of alcohol in amniotic fluid and blood, by intragastrically administering cineole and ethanol to the dams during gestational days 17 through 20 (paired condition) [19].
• The oedema response to 20 microl 1,8-cineole was significantly inhibited throughout its time-course in rats pretreated with antihistaminic and antiserotonergic drugs such as diphenhydramine, methysergide and cyproheptadine or with ketotifen, a mast cell stabilizer [22].
• Furthermore, 1,8-cineole was able to cause rat peritoneal mast cell degranulation (94%) in vitro, in a concentration as low as 0.3 microl/ml, which was almost comparable to that produced by 0.1 microg/ml of compound 48/80 [22].

Gene context of cineole

• These results suggest that 1,8-cineole, a monoterpenoid present in nature, is one of the effective substrates for CYP3A enzymes in rat and human liver microsomes [21].
• 1,8-Cineole was found to be oxidized at high rates to 2-exo-hydroxy-1,8-cineole by rat and human liver microsomal P450 enzymes [21].
• CONCLUSION: These results characterize 1,8-cineol as strong inhibitor of TNF-alpha and IL-1beta and suggest smaller effects on chemotactic cytokines [28].
• Specific induction of apoptosis by 1,8-cineole was observed in human leukemia Molt 4B and HL-60 cells, but not in human stomach cancer KATO III cells [4].
• All of the studied essential oils showed antioxidant activity, but camphor and 1,8-cineole did not [29].

Analytical, diagnostic and therapeutic context of cineole

• Control groups were dams given cineole 4 hr before commencement of an acute state of alcohol intoxication (long-delay group) or were only exposed to water administrations (water control group) [19].
• Previous work has demonstrated the capability of near-infrared (NIR) spectroscopy to determine the cineole content (not less than 70% w/w) of eucalyptus oil with an accuracy comparable with that of the British Pharmacopoeia (BP) assay method [30].
• Gas chromatography/mass spectrometry identified terpinen-4-ol (42 %), a-terpineol (3 %) and 1,8-cineole (2%, respectively, of tea tree oil) as the water soluble components of tea tree oil [31].
• METHODS: Cytokine production was determined following 20 h of incubation cells with 1,8-cineol simultaneously with the stimuli in culture supernatants by enzyme immunoassay [28].
• Pretreatment of anesthetized rats with bilateral vagotomy significantly reduced the bradycardic responses to 1,8-cineole (10 mg/kg) without affecting hypotension [32].

References