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Eucalyptus spp. (Eucalypts) and Ficus religiosa (Sacred Fig)
Published in Azamal Husen, Herbs, Shrubs, and Trees of Potential Medicinal Benefits, 2022
Surendra Pratap Singh, Bhoomika Yadav, Kumar Anupam
The bark of F. religiosa comprises of bergaptol and bergapten. The phytosterols like (Choudhary, 2006), stigmasterol, sitosterol, and its glucoside (sitosteryl-d-glucoside) and lanosterol have been isolated from alcoholic and petroleum ether extracts of the bark (Thomas et al., 2000). The two substituted furanocoumarins, 4-hydroxy-7H-furo [3,2- g] chromen-7-one (Bergaptol) and 4-methoxy-7H-furo [3,2- g] chromen-7-one (Bergapten) are isolated from the benzene extract of the bark (Swami and Bisht, 1996). The isolated furanocoumarins are shown excellent in vitro antimicrobial activity. The carbocyclic polyol “Inositol” is isolated from the alcoholic bark extracts. Vitamin K1, methyl oleonate, n-octacosanol, and lupen-3-one isolated from the petroleum ether extracts of the bark. F. religiosa bark comprises around 8.7% total tannin content on average. The neutral detergent fiber (NDF), acid detergent fiber (ADF), acid detergent lignin (ADL), phenolic components, and saponins are found in the inner bark of F. religiosa (Mali and Borges, 2003).
Influence of Light on Essential Oil Constituents
Published in K. Hüsnü Can Başer, Gerhard Buchbauer, Handbook of Essential Oils, 2020
Marie-Christine Cudlik, Gerhard Buchbauer
A class of substances often brought into connection with phototoxicity of EOs are the furocoumarins. They are synthesized and used by plants as defensive chemicals and are characterized by their coumarin structure conjoined with a furan ring. Depending on their position, they can be differentiated into two subtypes: the linear psoralen type and the angular angelicin type (see Figure 28.16). Furocoumarins like psoralen, bergapten (= 5-MOP), xanthotoxin, and angelicin, which are abundant in the Apiaceae, Rutaceae (e.g., some Citrus species), Moraceae. and other families, are known to be phototoxic and also carcinogenic under UV irradiation (Fu et al., 2013). Others, like bergamottin, bergaptol, isobergapten, and isopimpinellin are non-phototoxic. Furocoumarins are larger than most EO constituents, but can pass over during steam-distillation anyway. Still, cold-pressed EOs show much higher content of these compounds than steam-distilled ones. Commonly available EOs that are known to be phototoxic include the EOs of angelica root, bergamot (cold pressed), bitter orange (cold pressed), cumin, fig leaf absolut, grapefruit (cold pressed), lemon (cold pressed), lime (cold pressed), mandarin leaf, opopanax, rue, and tagetes. The following might be phototoxic: clementine (cold pressed), combava fruit, skimmia, angelica root, celery leaf and seed, cumin seed, khella, lovage leaf, and parsnip (Tisserand and Young, 2014).
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
Many natural compounds have been reported to be mechanism-based inactivators of P450 enzymes. The best-known example could be furanocoumarins in grapefruit juice, which can interact with many prescription medications, such as ethinylestradiol, cyclosporin, midazolam, triazolam, and terfenadine (Guo and Yamazoe 2004). The main furanocoumarins bergamottin, bergaptol, dihydroxybergamottin, paradisin A, and paradisin B have been characterized as strong mechanism-based inactivators of CYP3A4 (Tassaneeyakul et al. 2000; Girennavar et al. 2007). Furanocoumarins are known as natural toxins that are widely distributed in numerous herbal medicines and have inhibitory effects on different P450 enzymes. Imperatorin and isoimperatorin, mainly found in Angelica dahurica, as well as psoralen and isopsoralen, isolated from Psoralea corylifolia, can mechanistically inactivate the activity of CYP2B6 (Cao et al. 2015; Ji et al. 2015; Zheng et al. 2015; Lu et al. 2016). In addition, psoralen and its derivatives, 5-methoxypsoralen and 8-methoxypsoralen, are mechanism-based inactivators of CYP2B1 and CYP2A6 (Koenigs and Trager 1998). Metabolic activation of the furan moiety is a key step in MBI. Furanocoumarins undergo oxidative metabolism to form furanoepoxide and/or γ-ketoenal intermediates, which are electrophilic and can further react with the nucleophilic sites of P450 enzymes (Zheng et al. 2015).
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 phenylpropanoid family mainly contains coumarins, lignans and phenylpropionic acids, many of which are possible inhibitors of CYP2C9. Many furanocoumarins have been reported to have inhibitory effects on different CYP enzymes, so they are also known as “natural toxins”. Exposure to furanocoumarins is extremely common for people, due to their wide distribution in numerous herbs, fruits and foods (Hung et al. 2017; Chen et al. 2018). The best-known example are the furocoumarins in grapefruit juice, which have been shown to interact with many prescription medications, such as ethinylestradiol, cyclosporin, midazolam, triazolam, and terfenadine (Guo and Yamazoe 2004). Bergamottin, bergaptol, dihydroxybergamottin, paradisin A, and paradisin B (Table 2) have been identified as the main furocoumarins and show strong inhibitory potency toward CYP enzymes, especially CYP3A4 and CYP2C9, with a lower IC50 for the latter. They are characterized as mechanism-based inactivators of CYP3A4, whereas the CYP2C9 inhibition mode is unclear. Obviously, the dimer form of paradisin A showed much stronger inhibitory effect than the monomer (Tassaneeyakul et al. 2000; Girennavar et al. 2007). Epoxidation metabolism of the furan moiety may be the crucial factor for CYP inhibition induced by furanocoumarins, including chalepensin, which is another furanocoumarin present in herbs of the Rutaceae family (Ueng et al. 2013; Row et al. 2006).
Relationship between Furocoumarin Intake and Melanoma History among US Adults in the National Health and Nutrition Examination Survey 2003-2012
Published in Nutrition and Cancer, 2020
Melissa M. Melough, Kijoon Kim, Eunyoung Cho, Ock K. Chun
Among the 11,696 adults whose diets were assessed in this analysis, 9,025 (77.2%) consumed dietary furocoumarins (Table 2). Among the lowest quintile of consumers, mean total furocoumarin intake was 0.1 μg/day (range = 0.0 to 0.4 μg/day). Quintiles 2, 3, 4, and 5 had means (with ranges) of 0.8 μg/day (0.4 to 1.4), 2.6 μg/day (1.4 to 4.4), 10.8 μg/day (4.4 to 23.8), and 512.7 μg/day (23.8 to 14514 μg/day), respectively, exhibiting a skewed distribution of intake. Among the furocoumarins measured, bergamottin contributed most significantly to adults’ intake (33.4 μg/day; SE = 2.2), followed by 6'7'-DHB (31.0 μg/day; SE = 2.8), bergaptol (9.0 μg/day; SE = 0.6), and bergapten (3.3 μg/day; SE = 0.2).