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Monographs of fragrance chemicals and extracts that have caused contact allergy / allergic contact dermatitis
Published in Anton C. de Groot, Monographs in Contact Allergy, 2021
3-Carene has been identified by chemical analysis in 69 of 91 essential oils, which have caused contact allergy / allergic contact dermatitis. In 9 oils, 3-carene belonged to the ‘Top-10’ of ingredients with the highest concentrations which may be expected in commercial essential oils of this type: dwarf pine oil (0.6–34.4%), cypress oil (7.2–25.9%), black pepper oil (4.3–17.6%), angelica root oil (6.4–17.5%), pine needle oil (1.4–13.0%), galbanum resin oil (1.6–9.5%), thuja oil (0.7–8.2%), star anise oil (0.03–0.7%), and turpentine oil (traces-0.3%) (12).
Metabolism of Terpenoids in Animal Models and Humans
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
3-Carene is found in various Pinaceae essential oils: (+)-3-Carene is a major compound of Pinus palustris essential, and (−)-3-carene of Pinus sylvestris. It is used as raw material in perfumery (Bornscheuer et al., 2014). In rabbits, 3-carene is metabolized into 3-caren-9-ol and presumably via 3-caren-10-ol, and further oxidized into carboxylic and dicarboxylic acid products (Ishida et al., 1981, 2005). Another metabolic pathway takes place via opening of the methylene bridge to m-mentha-4,6-dien-8-ol with subsequent dehydrogenation of the cyclohexene ring to m-cymen-8-ol (Ishida, 2005). In vitro experiments with human liver microsomes revealed 3-caren-10-ol and 3-carene epoxide as metabolites (Figure 10.4). Hydroxylation was catalyzed by CYP2B6, CYP2C19, and CYP2D6, whereas epoxidation could be attributed to CYP1A2 (Duisken et al., 2005). Interestingly, neither of these two metabolites, nor the supposed hydrolysis product of the epoxide, 3-carene-3,4-diol, could be detected in rabbit or human urine, yet (Ishida, 2005; Schmidt et al., 2013, 2015). A recent study (Schmidt et al., 2015) identified chaminic acid as a new metabolite in human urine after oral intake of 3-carene (Figure 10.4). Moreover, Schmidt et al. suggested that dihydrochaminic acid and carene-3,4,9-triol are additional metabolites of 3-carene in humans (Schmidt et al., 2015).
The Chemistry and Biological Activity of the Genus Bupleurum in Spain
Published in Sheng-Li Pan, Bupleurum Species, 2006
Alejandro F. Barrero, M. Mar Herrador, Pilar Arteaga, José F. Quílez
The antispasmodic activity of the essential oils of B. gibraltaricum (Ocete et al., 1989) and B. fruticosum (Lorente et al., 1989) was determined in rat uterus preparations using acetylcholine and oxytocin as agonists. The comparison of the antispasmodic activity against oxytocin shown by both essential oils indicated that the essential oil of B. gibraltaricum was able to modify the EC50 of the agonist at much lower doses. This activity has been attributed to the major component of the oil, 3-carene, which is lacking in B. fruticosum oil. This hydrocarbon was very effective against oxytocin-induced contractions, doses of 1.1 μg/ml and 2.2 μg/ml raised oxytocin EC50 by 3.1 and 6.4 times more than control values (Ocete et al., 1989).
Chemical composition, enantiomeric analysis and anticholinesterase activity of Lepechinia betonicifolia essential oil from Ecuador
Published in Pharmaceutical Biology, 2022
James Calva, Luis Cartuche, Salomé González, José Vinicio Montesinos, Vladimir Morocho
Several studies on the Lepechinia genus reported heterogeneity of identified compounds, which has not allowed the establishment of a typical metabolic pattern. So far to date, the essential oils of some Lamiaceae, including two species belonging to the genus Lepechinia spp. have been studied (Velasco-Negueruela et al. 1994; Cicció et al. 1999; Acevedo et al. 2005; Borges et al. 2006; Arze et al. 2009; Valarezo et al. 2012; Panamito et al. 2021). Two related studies of EO from L. mutica (Benth) Epling, reported a great variation in the chemical composition. Malagón et al. (2003) identified 54 compounds, among them β-phellandrene (30%), camphene (13%), limonene (8%), 3-carene (6%) and α-pinene (6%) were the most abundant. On the other hand, Ramírez et al. (2018) reported the identification of δ-3-carene (24.23%), eudesm-7(11)-en-4-ol (13.02%), thujopsan-2-α-ol (11.90%), β-pinene (7.96%), valerianol (5.19%), and co-eluting limonene and β-phellandrene (4.47%) as the main constituents. In another study, with a related species from the same geographical location, Gilardoni et al. (2018) reported from L. heteromorpha (Briq) Epling, the identification of 25 constituents, where viridiflorene (27.3%), (E,E)-α-farnesene (1.4%), ledol (21.2%), spirolepechinene and (E)-β-caryophyllene (7.1%), allo-aromadendrene (6.1%) were the main constituents.
Potential Alternative Treatment of Ocular Bacterial Infections by Oil Derived from Syzygium aromaticum Flower (Clove)
Published in Current Eye Research, 2018
Mahmoud S. M. Mohamed, Asmaa A. Abdallah, Magda H. Mahran, Ahmed M. Shalaby
The antibacterial activity of hydrocarbon monoterpene δ-3-carene was reported. δ-3-carene participates in lipids of the bacterial cell membrane due to its hydrophobicity thereby disrupting the membrane structures. 40 On the other hand, γ-Terpinene had high specific bacteriostatic action on microbial cells. 41 In our study, the predominant compounds of E. globulus oil were 3-Carene followed by γ-Terpinene (Table 5). This may explain the antimicrobial activities of E. globulus oil (85%) against all tested bacterial isolates. In addition, C. citratus oil showed high sensitivity rate (97%). Its major compounds are β-Ocimene (12.66%) followed by 3-Carene (11.72%). The antibacterial activity of β-Ocimene has been reported in previous studies. 40
The attenuation effect of low piperine Piper nigrum extract on doxorubicin-induced toxicity of blood chemical and immunological properties in mammary tumour rats
Published in Pharmaceutical Biology, 2022
Jirakrit Saetang, Aman Tedasen, Surasak Sangkhathat, Natnaree Sangkaew, Sirinapa Dokduang, Napat Prompat, Siriporn Taraporn, Potchanapond Graidist
Circulating cytokines can be used as a marker to monitor the immune status of the body. In the aspect of tumour immunobiology, tumour microenvironment has been proposed for its role in cancer progression and metastasis, and this scenario requires interaction between cancer cells, immune cells and tumour stroma, which consequently reflect the immune response of the patients (Hirata and Sahai 2017). Cytokine profiling of rats treated with different types of regimens demonstrated the role of Dox and PFPE-Dox combination on the immune response. Interestingly, the levels of CXCL-7, TIMP-1, sICAM-1 and l-selectin of the vehicle and Dox groups seemed to be equal, although Dox inhibited tumour progression. In addition, all of those cytokines have been reported for their role in the tumour promoting function (Yamada et al. 2005; Ridnour et al. 2012; Grepin et al. 2014). This phenomenon may indicate the immunological response which still mimicked the tumour promoting environment influenced by Dox despite the suppression of the tumour being found. It was noticeable that the use of PFPE suppressed all of these cytokines in the Dox group, and some compounds in PFPE were remarkably demonstrated to inhibit these cytokines directly in the tumour model. To illustrate, 3-carene and pellitorine were found to inhibit the expression of CXCL7 through the suppression of IL-6 from cancer cells leading to cancer elimination (Chiang et al. 2012; Ku et al. 2014; Basholli-Salihu et al. 2017). Caryophyllene and α-humulene were also reported to suppress sICAM-1 production (Tanaka et al. 2001). Moreover, TIMP-1 expression could be inhibited by β-caryophyllene treatment in the liver fibrosis animal model (Calleja et al. 2013). This demonstrated that all of these antioxidants in PFEP could synergistically help to suppress a tumour-promoting immunological environment.