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Metabolism of Terpenoids in Animal Models and Humans
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
(–)-Terpinen-4-ol is the main compound of Melaleuca alternifolia essential oil, which is widely used in cosmetic and pharmaceutical products due to its antiseptic properties (Bornscheuer et al., 2014). As shown in Figure 10.25, terpinen-4-ol is oxidized to p-menth-1-en-4,8-diol and 1,2-epoxy-p-menthan-4-ol. Further experiments with human recombinant CYPs identified CYP3A4, CYP 2A6, and to a lesser extent CYP1A2 as the main enzymes involved in the formation of terpinene-4-ol (Haigou and Miyazawa, 2012).
Catalog of Herbs
Published in James A. Duke, Handbook of Medicinal Herbs, 2018
Toxicity — The diuretic principle is 4-terpineol or terpinen-4-ol, excessive doses of which may produce kidney irritation. Juniper and extracts should not be used by expectant mothers because they increase intestinal movements and uteral contractions. “This drug is no longer recommended for various kidney disorders by the medical profession. Since much safer and more effective diuretic and carminative drugs exist, the use of jumper in folk medicine should also be abandoned.”37 Symptoms of external poisoning caused by the essential oil on the skin include burning, redness, inflammation with blisters, and swelling. Internally, symptoms are from overdose, pain in or near the kidney, strong diuresis, albuminuria, hematuria, purplish urine, accelerated heartbeat and blood pressure, and, rarely, convulsive apparitions, metrorrhagia, and, more rarely, abortion.33
Phytotherapeutic Agents in Epilepsy
Published in Vikas Kumar, Addepalli Veeranjaneyulu, Herbs for Diabetes and Neurological Disease Management, 2018
Several monoterpenoid alcohols have shown anticonvulsant activity in convulsion animal models. Terpinen-4-ol is a monoterpenoid alcohol occurring as a component of the essential oils of several aromatic plants. It is the main component of the essential oil of the Australian native plant Melaleuca alternifolia (Fam. Myrtaceae) (tea tree oil). Terpinen-4-ol significantly increases the latency of PTZ-induced convulsions. It also inhibits seizures induced by PIC and MES seizures.62
Non‐pharmaceutical treatment options for meibomian gland dysfunction
Published in Clinical and Experimental Optometry, 2020
Demodex mites are resistant to a wide range of antiseptic agents, including 75% alcohol, 10% povidone‐iodine, and erythromycin.2007In vivo microscopic observation for 150-minutes revealed that D. folliculorum was killed by tea tree oil in a dose‐dependent manner.2007 In addition to this action, tea tree oil has been found to manifest antibacterial,2004 antifungal,2004 and anti‐inflammatory2004 effects. Terpinen‐4‐ol, a terpene with antimicrobial, antifungal, antiviral, antiseptic, and acaricidal properties, is the active ingredient of tea tree oil with regard to the killing of Demodex mites.2013 A concentration of tea tree oil as low as 5% applied to the lids and base of the eyelash follicles twice daily or as high as 50% applied once weekly was found to attenuate Demodex infestation.2013 However, tea tree oil can cause dermatitis, allergy, and ocular irritation, especially at higher concentrations,2012 and treatment to eradicate Demodex completely is often unrealistic.
Antimicrobial effects of terpinen-4-ol against oral pathogens and its capacity for the modulation of gene expression
Published in Biofouling, 2018
Ester Alves Ferreira Bordini, Caroline Coradi Tonon, Renata Serignoli Francisconi, Fernando Augusto Cintra Magalhães, Patrícia Milagros Maquera Huacho, Telma Lombardo Bedran, Sebastião Pratavieira, Luis Carlos Spolidorio, Denise Palomari Spolidorio
Terpinen-4-ol [3-cyclohexen-1-ol,4-methyl-1-(1-methylethyl)-, (R)-] is a terpene considered to be the primary component of the essential oil of Melaleuca alternifolia, also known as tea tree oil (TTO), and can be found in other plants, such as Alpinia zerumbet and Eucalyptus species from Hajeb Layoun arboreta (Tunisia) (Elaissi et al. 2010; de Souza et al. 2018). TTO is a mixture of ∼100 compounds, including the monoterpenes terpinen-4-ol (at least 30% of the oil), 1,8-cineole and terpinolene. TTO became known worldwide in the eighteenth century and possesses antimicrobial, anticancer and anti-inflammatory properties (Nogueira et al. 2014). It has broad-spectrum activity against Gram-positive and Gram-negative bacteria, as well as antimicrobial-resistant and multi-resistant microorganisms (Thomsen et al. 2013). The antimicrobial mechanisms of terpinen-4-ol are due to the lipophilicity of the oil, which can penetrate through cytoplasmic membranes and cell walls. Its causes internal osmotic pressure, and the cell wall becomes weak, rupturing the membrane with the subsequent loss of the cytoplasmic material (Carson et al. 2002; Li et al. 2016). Several reports have demonstrated that the addition of terpinen-4-ol and TTO in oral care products, such as mouthwashes and toothpastes, has a demonstrable antiseptic effect, inhibiting bacterial growth and adhesion to the dental biofilm (Saxer et al. 2003; Maggi et al. 2009; Rahman et al. 2014; Varma et al. 2018).
In vitro antibacterial and cytotoxic activities of carvacrol and terpinen-4-ol against biofilm formation on titanium implant surfaces
Published in Biofouling, 2018
Patricia Milagros Maquera-Huacho, Caroline Coradi Tonon, Marilia Ferreira Correia, Renata Serignoli Francisconi, Ester Alves Ferreira Bordini, Élcio Marcantonio, Denise Madalena Palomari Spolidorio
It is necessary to determine the possible toxic effects of carvacrol and terpinen-4-ol on cells to evaluate their potential clinical applications. In this study, the cells were exposed for different contact times to the test substances and regardless of the concentration, the results revealed a concentration-and-time-dependent decrease at all the concentrations assayed for carvacrol, terpinen-4-ol and CHX (Figure 4). The monoterpenes carvacrol and terpinen-4-ol are isomeric. Despite having the same molecular formula, these compounds exhibit different levels of cytotoxic activity against cell lines. Thus, unlike the other concentrations evaluated, after 5 min contact time, terpinen-4-ol (0.24%) showed mild-grade cytotoxicity compared with the control group (93.75%) according to the ISO 10993-5 2009 Standard: Biological Evaluation of Medical Devices: In vitro Method. This study evaluated the toxic effects of carvacrol and terpinen-4-ol on fibroblasts since these cells are involved in the re-osseointegration and osseointegration processes.