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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
(+)-Menthofuran is a constituent of peppermint oils (2%–10%) (Bornscheuer et al., 2014). It has been demonstrated that menthofuran contributes to the nephrotoxicity of pulegone (Khojasteh et al., 2010). Treatment of rat liver slices with toxic concentrations of menthofuran produced several monohydroxylated metabolites, mintlactone and 7-hydroxymintlactone. Glutathione conjugates of 7-hydroxymintlactone and menthofuran were also identified (Figure 10.18). The metabolites could also be detected in vivo in rat urine. These reactions are catalyzed by human CYP1A2, 2B6, 2C19, 2E1, and 3A4 (Khojasteh-Bakht et al., 1999; Lassila et al., 2016). In vitro experiments with human liver S9 fraction also demonstrate the formation of several menthofuran-glutathione conjugates (Lassila et al., 2016).
Aquatic Plants Native to Europe
Published in Namrita Lall, Aquatic Plants, 2020
Isa A. Lambrechts, Lydia Gibango, Antonios Chrysargyris, Nikolaos Tzortzakis, Namrita Lall
In the oils from plants collected from Iran and Asia, menthofuran were not detected in the leaves or the stems, instead the major components were a-caryophyllene (22.4%) and piperitone oxide (25.7%) for stems and leaves, respectively, with 10% limonene in both parts (Esmaeili et al. 2006). Oils extracted from plants grown in Ethiopia (Africa) contained 70.5% of menthofuran and 10% of limonene (Getahun et al. 2008), but essential oils from the plants grown in Tunisia had high percentages of pulegone (39.3%), which is the precursor of menthofuran (Dhifi et al. 2011). According to Dhifi et al. (2011), these differences in the composition of the oil could be attributed to the genotype, the environmental, and agronomic conditions. Additionally, differences in the essential oil components are noticed between different stages of the ontogenetic cycle (vegetative, flowering and senescence) (Andro et al. 2013).
Respiratory involvement from herbals
Published in Philippe Camus, Edward C Rosenow, Drug-induced and Iatrogenic Respiratory Disease, 2010
Tracey K Riley, Kahoko Taki, Christopher P Holstege
Oil of pennyroyal is derived from the plant Mentha pulegium and is known for its insect-repellent effects and for being an abortifacient and an emmenagogue. Unfortunately, it has also been found in herbal mint teas mistakenly taken or given as home remedies to treat common aliments in children.52 The active ingredient in pennyroyal oil is R – (+)-pulegone which is metabolized by the cytochrome P450 system to menthofuran, which is one of several reactive metabolites. Hepatotoxicity, the most common manifestation of a toxic ingestion of pennyroyal oil, is thought to occur due to depletion of hepatic glutathione stores by the reactive metabolites. However, the exact mechanism of oil of pennyroyal toxicity is not clearly elucidated and toxicity is known to occur in extrahepatic tissues. Pulegone and menthofuran were found to cause both hepatotoxicity and pulmonary toxicity in mice.53 Currently, there are no published minimal toxic levels for pulegone and menthofuran in humans.52
Toxicological effects of Mentha x piperita (peppermint): a review
Published in Toxin Reviews, 2021
Khojasteh Malekmohammad, Mahmoud Rafieian-Kopaei, Samira Sardari, Robert D. E. Sewell
The chemical constituents of M. x piperita are comprised of monoterpenoids, the main components of its essential oil. These include menthol (29%–48%), menthone (20%–31%), menthofuran (6%–8%), pulegone, menthyl acetate (3%–10%), limonene, pinene and piperitone in addition to caffecic acid, flavonoids such as luteolin and menthoside, polyphenols including rosmaric acid, carotenes, tocopherols, narirutin, eriodictyol, tannins, betaine and choline (Shah and D’Mello 2004, Peixoto et al.2009, Rita and Animesh 2011, Johari et al.2015). An active component of peppermint essential oil that has also been highlighted in many studies as a key ingredient of the plant is menthol but it also contains other constituents such as its biosynthetic precursor pulegone and its metabolites menthone and menthofuran (Figure 1) (Khojasteh-Bakht et al.1999, Nair 2001, SCF 2002, Coteau et al. 2005, Mimica-Dukic and Bozin 2008).
Phytodermatitis in East and southeast of Turkey: A prospective study
Published in Cutaneous and Ocular Toxicology, 2019
The Lamiaceae family is found in the group of perennials and is known as aromatic plants. M. pulegium is a flowering plant belonging to the family Lamiaceae. M. pulegium shows toxic effects to the liver when taken orally, menthofuran is responsible of the toxic effect18. There is a case of ACD due to M. pulegium, confirmed with positive patch test and negative prick test. Limonene, the first cyclic intermediate in the biosynthesis of monoterpenes in M. pulegium, was reported to be responsible for this reaction19. In addition, a case of urticaria associated with M. pulegium was reported and menthol was thought to be responsible for this reaction20. In our study, ICD developed in three patients due to M. pulegium (Figure 5). In these cases, M. pulegium was applied topically to the abdomen, back and leg area and covered with nylon and kept for at least 8 h. In all three cases, bullous lesions developed and postinflammatory hyperpigmentation remained after treatment.
Gamma irradiation-induced variability in morpho-agronomic and oil quality traits of Mentha piperita L.
Published in International Journal of Radiation Biology, 2021
Priyanka Prasad, Vagmi Singh, Nashra Aftab, Akancha Gupta, Ram Kishor, Himanshu Kumar Kushwaha, Vivek Singh, Ram Swaroop Verma, Birendra Kumar
However, plant breeders still could not attain the desired goal to develop a superior genotype/mutant in M. piperita having an ideal morphotype, with an oil content of M. arvensis, and oil quality of M. piperita. Therefore, in this study mutation breeding program (γ-irradiation) has been attempted on the runners of menthol rich genotype MPK-5 to generate novel variability fulfilling specific objectives viz. (i) variation in agro-morphological characters (ii) to increase the biomass and oil yield and (iii) improve the essential oil quality having high menthol with a low amount of menthofuran.