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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
D-Pulegone is a colorless clear oily liquid; its odor type is minty and its odor is described as ‘minty, sulfuraceous, sweet with metallic buchu nuances’ (www.thegoodscentscompany.com). Pulegone is used as chemical intermediate and for flavoring. Pennyroyal oil contains 60%-90% pulegone and may be used for flavoring foods, drinks, and dental products. This oil has also been used as a herbal medicine proposed to induce menstruation and abortion (U.S. National Library of Medicine).
Metabolism of Terpenoids in Animal Models and Humans
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
(R)-(+)-Pulegone is present in essential oils of Lamiaceae. Hedeoma pulegioides and Mentha pulegium, both commonly called pennyroyal, contain essential oils that are chiefly pulegone (O'Neil, 2006; Bornscheuer et al., 2014). Pennyroyal herb had been used for inducing menstruation and abortion. In higher doses, however, it may result in central nervous system toxicity, gastritis, hepatic and renal failure, pulmonary toxicity, and death. Commercially available, pennyroyal oils have a pulegone content >80% and are both hepatotoxic and pneumotoxic in mice (Engel, 2003). Though pulegone has been used for flavoring food and oral hygiene products, the pulegone content in foods and beverages is restricted by EU law. At nontoxic concentrations, pulegone is oxidized selectively at the 10-position and further metabolized into menthofuran. In vitro data show that this metabolic pathway is mainly catalyzed by human CYP2E1, and to a lesser extent by CYP1A2 and CYP 2C19 (Khojasteh-Bakht et al., 1999). Alternatively, it may be reduced to menthone, which has been detected in trace levels in urine samples. It might be possible that pulegone is also reduced at the carbonyl group first. Consequently, pulegol is either reduced very efficiently to menthol or rearranged to 3-p-menthen-8-ol (Engel, 2003) (Figure 10.23). In rats, three major pathways have been identified: (a) hydroxylation followed by glucuronidation, (b) reduction to menthone and hydroxylation, and (c) conjugation with glutathione and further metabolism (Chen et al., 2001; Ferguson et al., 2007).
Chemophobia and the Boy Who Cried Wolf
Published in David Lightsey, The Myths about Nutrition Science, 2019
Dr. Josh Bloom, the Director of Chemical and Pharmaceutical Science for the ACSH, provides the following examples illustrating how irrational this decision is using three of the seven chemicals banned. The following examples are taken from Dr. Bloom’s May 29, 2018 article Enviro-Thugs Sue To Keep Natural Food Flavors Out of Food.15Myrcene: Occurs naturally in lemongrass, hops, basil, and mangos, and ginger.Pulegone: Is another naturally occurring chemical that is found all over the place. The minty-smelling chemical is found in peppermint, spearmint, blueberries, chamomile, black currant, catnip, black tea. . . . Like myrcene, pulegone is listed as a carcinogen on Crazifornia’s Prop 65 list.Methyleugenol: Is a clove-scented chemical that is also found widely in plants and fruits, for example, nutmeg, apples, banana, orange juice, grapefruit, among others.
Bioactivation of herbal constituents: mechanisms and toxicological relevance
Published in Drug Metabolism Reviews, 2019
(R)-Pulegone (PUL, Figure 14(c)) is a major constituent of pennyroyal oil (80–90%) extracted from the leaves of Mentha pulegium and Hedeoma pulegoides, and a minor component in some other mint species, such as Mentha piperita (peppermint). Tea or oil prepared from the leaves of these plants have been used for decades as an aromatic stimulant, carminative, headache remedy, abortifacient (Gunby 1979). However, ingestion of large quantities of pennyroyal oil can cause severe tissue damage leading to dangerous and even fatal consequences (Sullivan et al. 1979). The metabolism-based hepatotoxicity by pennyroyal oil was classified as hepatic centrilobular necrosis in both animals and human (Gordon et al. 1982). The toxicity of PUL is attributed to its α-isopropylidene ketone moiety (Figure 14(c)). Reduction of the ketone (yielding pulegol) or the isopropylidene double bond (yielding menthone and isomenthone) completely abolishes the toxicity.
The combined effect of essential oils on wood physico-chemical properties and their antiadhesive activity against mold fungi: application of mixture design methodology
Published in Biofouling, 2023
Moulay Sadiki, Mounyr Balouiri, Soumya Elabed, Fadoua Bennouna, Mohammed Lachkar, Saad Ibnsouda koraichi
For T. vulgaris essential oil, 29 components were determined, accounting for 89% of the total amount. The major constituents were thymol (40%), γ-terpinene (12%), p-cymene (12%), linalool (4.4%), and carvacrol (3.1%). Regarding M. communis, 47 compounds were determined, representing 98% of the total content of essential oil, with 1.8-cineol (28%), α-pinene (24.3%), limonene (14%), and myrtenyl acetate (13%) as majors compounds. Concerning M. pulegium essential oil, it was mainly composed of pulegone (74%), carvone (6%), and dihydrocarvone (5%).
Pulegone inhibits inflammation via suppression of NLRP3 inflammasome and reducing cytokine production in mice
Published in Immunopharmacology and Immunotoxicology, 2019
Qingxin Yang, Jie Luo, Hongjun Lv, Taoqun Wen, Boyu Shi, Xiaobo Liu, Nan Zeng
Pulegone, a key compound in Schizonepeta essential oil, has been identified as a component of the anti-inflammatory action [20]. It exerts an array of pharmacology functions, including anti-inflammatory, anti-oxidant, anti-biotic, and anti-ulcer effects [21]. However, its underlying molecular mechanisms on NLRP3 inflammasome still remain equivocal [21,22]. Here, we aimed to explore the effects of pulegone on LPS-induced C57BL/6J mice sepsis model and its modulatory effect on NLRP3 inflammasome.