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Plant-Based Essential Oils in The Treatment of Microbial Infections
Published in Mahendra Rai, Chistiane M. Feitosa, Eco-Friendly Biobased Products Used in Microbial Diseases, 2022
Hercília Maria Lins Rolim, Alessandra Braga Ribeiro, Monalisa de Alencar Lucena, Andressa Barros Ibiapina, Thais Cruz Ramalho
Copaifera langsdorffii Desf. is another species of the genus Copaifera that has great commercial potential and is commonly used in traditional medicine, due to the biological properties present in the extracts of the leaves and in the oil-resin extracted from the trunks, including antimicrobial, leishmanicidal and antimalarial activity (Lemos et al. 2015). Ribeiro et al. (2019) showed that the essential oil extracted from the oil-resin of C. langsdorffii presented β-bisabolene (32.0%) as a major compound and a small amount of β-caryophyllene (9.7%). The activity was observed against S. aureus, P. aeruginosa and S. choleraesuis (MICs between 125 and 500 μg/mL), in addition to antifungal activity against Candida species, with the greatest activity against C. tropicalis (MIC = 15.6 μg/mL) (Table 11.1). Gomes da Silva et al. (2012) conducted a clinical study with formulations containing C. langsdorffii EO for the treatment of acne and reported a significant decrease in the surface affected with acne (Propionibacterium acnes) after application of the formulation, with cis-thujopsene (46.96%) as the major compound, and also the presence of caryophyllene (6.71%) (Table 11.1).
Chemistry of Essential Oils
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
The santalols (122) and (123) have more complex structures and are the principal components of sandalwood oil. Cedrol (120) is another complex alcohol, but it is more widely occurring in nature than the santalols. It is found in a wide range of species, the most significant being trees of the Juniperus, Cupressus, and Thuja families. Cedrene (146) occurs alongside cedrol in cedarwood oils. Cedrol is dehydrated to cedrene in the presence of acid, and so the latter can be an artifact of the former and the ratio of the two will often depend on the method of isolation. Thujopsene (126) also occurs in cedarwood oils, usually at a similar level to that of cedrol/cedrene, and it is found in various other oils also. Caryophyllene (128) and α-humulene (the all trans-isomer) (133) are widespread in nature, cloves being the best-known source of the former and hops of the latter. The ring systems of these two materials are very strained making them quite reactive chemically, and caryophyllene, extracted from clove oil as a by-product of eugenol production, is used as the starting material in the synthesis of several fragrance ingredients. Longifolene (131) also possesses a strained ring system. It is a component of Indian turpentine and is therefore readily available as a feedstock for fragrance ingredient manufacture.
Types of Raw Incense
Published in Kerry Hughes, The Incense Bible, 2014
Cedarwood oil is a mixture of volatile sesquiterpenes from the heartwood of Cedrus, as well as other plants commonly used to extract “cedarwood oil,” such as Juniperus and Cupressus species. In fact, the Juniperus and Cupressus species are used more commonly for the production of cedarwood oil because they have the highest yield. However, cedar species are still used for the production of cedarwood oil, such as Cedrus atlantica and C. deodara. Typical sesquiterpene content of cedarwood oil includes alpha- and beta-cedrene, thujopsene, cuparene, cedrol, and widdrol (Langenheim, 2004; Fischer-Rizzi, 1996).
Mechanism-based inactivation of cytochrome P450 enzymes by natural products based on metabolic activation
Published in Drug Metabolism Reviews, 2020
Tingting Zhang, Jinqiu Rao, Wei Li, Kai Wang, Feng Qiu
Another sesquiterpenoid, thujopsene, is the main bioactive component of the essential oils of cedar and conifers. It can irreversibly inhibit the enzymatic activities of CYPs 2C8, 2C9 and 2C19. The half-maximal inhibitory concentration (IC50) values were shown to increase in the following order: CYP2C19 (13.6 μM) < CYP2C8 (29.8 μM) < CYP2C9 (44.9 μM) (Table 1). The underlying mechanism may be related to metabolic activation, but the structures of the reactive metabolites of thujopsene are still unclear (Jeong et al. 2014).
Inhibition of CYP2C9 by natural products: insight into the potential risk of herb-drug interactions
Published in Drug Metabolism Reviews, 2020
Kai Wang, Qing Gao, Tingting Zhang, Jinqiu Rao, Liqin Ding, Feng Qiu
The medicinal herb ginseng has been extensively used for thousands of years worldwide. There have been some reports about ginseng–prescription drug interactions (Donovan et al. 2003; Jiang et al. 2004; Gurley et al. 2005). Ginseng is abundant in triterpenoid saponins, which are known as ginseng saponins or ginsenosides. However, ginsenosides are not only the major biologically active constituents of ginseng but also potential harmful ingredients that may cause HDIs because of their inhibitory effects on CYP enzymes, such as CYP2C9 (Zheng et al. 2014). In particular, the ginsenoside Rd had moderate inhibitory potency toward CYP2C9, with an IC50 value of 105 μM (He and Edeki. 2004). As shown in Table 3, numerous triterpenoids naturally occurring in other herbs, such as Radix Bupleuri, Andrographis paniculate, Centella asiatica, and Lindera aggregata (Sims) Kosterm, exhibit inhibitory effects on CYP2C9 in vitro (Pan et al. 2011). Among these, a furan-containing sesquiterpenoid, linderane, that is found in Lindera aggregata (Sims) Kosterm, has been proven to be a mechanism-based inactivator of CYP2C9. Linderane could cause the irreversible inhibition of CYP2C9 in an NADPH-, time-, and concentration-dependent manner with a Ki value of 1.26 μM (Wang et al. 2015). The underlying mechanism should be attributed to the formation of furanoepoxide and γ-ketoenal intermediates by oxidative metabolism of the furan ring. The metabolic intermediates are electrophilic and capable of reacting with the nucleophilic groups of CYP2C9, resulting in covalent binding of the protein or heme (Wang et al. 2015). Another sesquiterpenoid, thujopsene, which is the main bioactive component of essential oils of cedar and conifers, was also found to be a mechanism-based inactivator of CYP2C9 (Jeong et al. 2014). Similarly, further mechanism involved may be related to metabolic activation, whereas the structure of its reactive metabolite remains unknown. MBI of CYP2C9 may produce severe adverse reactions, especially for drugs with narrow therapeutic windows such as S-warfarin.