China
Africa
Explore chapters and articles related to this topic
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
The allergenicity of limonene is closely related to this oxidation process. The primary oxidation products formed, the hydroperoxides (limonene-1-hydroperoxide, limonene-2-hydroperoxide) are strong and clinically relevant contact allergens (5,9,10,25,26,27,104). Limonene-1-hydroperoxide is the stronger sensitizer (104) and clinically the most important allergen (105). Both hydroperoxides are unstable and readily degrade to secondary stable oxidation products such as carvone and carveol (5). R-(-)-Carvone is also a potent sensitizer in animal experiments, but cis- and trans-carveol have no or very little sensitizing capacity (10). If the oxidation process continues, polymers are created and the liquid will become viscous (3). The addition of an antioxidant such as BHT to limonene or limonene-containing products can prevent autoxidation for periods depending on the purity of the products and on the room temperature. Cold and dark storage of D-limonene in closed vessels can prevent autoxidation for one year without addition of anti-oxidant (16).
Biotransformation of Monoterpenoids by Microorganisms, Insects, and Mammals
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
Yoshiaki Noma, Yoshinori Asakawa
α-Terpineol (34) was obtained from (+)-limonene (68) by fungi such as P. digitatum, Penicillium italicum, and Cladosporium and several bacteria (Figure 22.29). (+)-cis-Carveol (81b), (+)-carvone (93) (an important constituent of caraway seed and dill-seed oils) (Fenaroli, 1975; Bouwmester et al., 1995), and 1-p-menthene-6,9-diol (90) were also obtained by P. digitatum and P. italicum. (+)-(S)-Carvone (93) is a natural potato sprout–inhibiting, fungistatic, and bacteriostatic compound (Oosterhaven et al., 1995a,b). It is important to note that (−)-carvone (93′, the spearmint flavor) was not yet described in microbial transformation (Krasnobajew, 1984). However, the biotransformation of limonene to (−)-carvone (93′) was patented by a Japanese group (Takagi et al., 1972). Corynebacterium species grown on limonene was able to produce about 10 mg/L of 99% pure (−)-carvone (93′) in 24–48 h.
Inhibition of interferon-γ production and T-bet expression by menthol treatment of human peripheral blood mononuclear cells
Published in Immunopharmacology and Immunotoxicology, 2019
Maryam Bayat, Kurosh Kalantar, Zahra Amirghofran
Mentha longifolia (L.) Huds belongs to the Lamiacea family, is a fast-growing and aromatic plant that grows in wet regions throughout Europe, Asia, Australia, and South Africa [11]. This plant is generally cultivated for the production of essential oils and used as flavors for the manufacture of perfumes or for medical purposes. In traditional medicine, M. longifolia is considered as a sedative, analgesic, anti-spasmodic and anti-inflammatory herb [12]. This plant is used in the treatment of gastrointestinal diseases and due to its anti-parasitic, anti-fungal and anti-bacterial properties has benefits in the treatment of infectious diseases [13,14]. M. logifolia has shown anti-inflammatory effects by decreasing NO secretion and tumor necrosis factor (TNF)α in macrophages [15]. In our previous study, we have shown the effect of various extracts of this plant on reducing interferon (IFN)γ by activated lymphocytes [16]. M. longifolia has several components including menthol, menthone, pulegone, carveol, broneol and piperitone [17,18]. Some of these compounds have shown good antimicrobial activity against various human and animal pathogens and few have demonstrated anti-inflammatory effects [17]. For example borneol decreased the level of TNF-α and interleukin (IL)-1β in focal cerebral ischemia-reperfusion rats and carvone reduced prostaglandin synthesis [19,20]. Menthol has been reported to be the most abundant and active ingredient of M. longifolia, that its antimicrobial and antioxidant properties have been shown [21]. The anti-allergic effects of menthol on type 1 hypersensitivity reactions have been reported [22]. Menthol inhibited the release of histamine from mast cells and effectively reduced the symptoms of rhinitis and diminished the levels of IL-4 and IL-10 cytokines in mice infected with schistosoma parasite [23]. Considering the immunomodulatory effects of M. longifolia we hypothesize whether menthol is one of the major compounds in this plant responsible for its immunomodulatory effects.
Phytochemical constitutes and biological activities of essential oil extracted from irradiated caraway seeds (Carum carvi L.)
Published in International Journal of Radiation Biology, 2023
Amina Aly, Rabab Maraei, Ahmed Rezk, Ayman Diab
Carvone is the most important Carum carvi oil ingredient; as it is a perfume or flavor, potato sprouting inhibitor, antimicrobial agent, biochemical environmental indicator, and medicinal plant (Afify et al. 2012; Raal et al. 2012). The findings revealed that gamma irradiation had noteworthy effects on the content of some compounds in the oil extracted from un-irradiated and irradiated caraway seeds. It has been observed that some compounds appeared in irradiated treatments, such as Ascaridole, Methyl 4,7,10,13-hexadecatetraenoate, Bicyclo[5.2.0]nonae, 2-Methylene-4,8,8-trimethyl-4-vinyl, Benzen, 1-(1,5-dimethy-4-hexenyl)-4-methyl, Isolongifolene, Cholestan-3-ol,2-methylene-, (3.beta,5.alpha)-, and β-Nootkatol. In addition, there are some compounds that decreased due to irradiation treatments, such as γ-Terpinene and Trans-caryophyllene, and others disappeared by increasing the irradiation treatments, such as Cis-carveol and Tricyclo[4.4.0.0(2,8)]decan-3-ol (Table 1). The identified compounds have many biological characteristics, among the identified compounds, α- and β-pinene have which has antibiotic resistance modulation (Kovac et al. 2015), anticoagulant (Yang et al. 2011), anticancer, antibacterial, antimalarial, antioxidant, anti-inflammatory, and analgesic properties (Salehi et al. 2019). Limonene has been identified as an anticancer agent due to its ability to produce apoptosis by up-regulating pro-apoptotic factors while down-regulating anti-apoptotic issues (Mukhtar et al. 2018). γ-Terpinene has an antioxidant activity compound as well as Ascaridole has anticarcinogenic effects (Sobral et al. 2014). Carveol is a natural unsaturated, monocyclic monoterpenoid alcohol that prevents breast cancer (Chebet et al. 2021). Carvone is a monoterpene that has certain cancer-preventive and anthelmintic properties (Malhotra 2012). Cyclopentanone, 2-cyclopentylidene- has anti-inflammatory, analgesic, and anticonvulsant properties. Also, Methyl 4,7,10,13-hexadecatetraenoate has antioxidant and antimicrobial activity (Sosa et al. 2016). Trans-caryophyllene is sesquiterpene that has a variety of pharmacological effects, such as antioxidant, anti-inflammatory, anticancer, antibiotic, and local anesthetic activities (Shan et al. 2017). Benzen, 1-(1,5-dimethy-4-hexenyl)-4-methyl as well, has antimicrobial and anti-inflammatory properties and also, Cholestan-3-ol,2-methylene-, (3.beta,5.alpha)- has anti-inflammatory, and cytotoxic activities. Isolongifolene is a tricyclic sesquiterpene that has antioxidant, anti-inflammatory, anticancer, and neuroprotective properties. Myristicin is used as an antidepressant, anti-inflammatory, and antioxidant. The compound Caryophyllene oxide is bicyclic sesquiterpenes, has major anticancer properties, impacting increase and propagation of several cancers cells and also, is recognized as antimicrobial activities against a broad spectrum of bacteria and fungi. Plants are one of the natural sources of bioactive substances, lots of them can be used to promote fitness and fight disease status and lots are used as foodstuff or herbal medications (Sharma et al. 2009). The current findings are consistent with Laribi et al. (2013), who cited the predominance of Carvone and Limonene in essential oils of Tunisian, German, and Egyptian caraway ecotypes.