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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).
Catalog of Herbs
Published in James A. Duke, Handbook of Medicinal Herbs, 2018
On steam distillation French seed yield 1.9 to 2.4% oil; Indian seed yield 2.14 to 2.50%. The essential oil contains the glucoside apiin. Celery seed oil contains ca. 60% limonene, 10 to 15% selenine, 1 to 3% sesquiterpene alcohols, sedanolide, sedanonic anhydride a phenol (perhaps guaiacol), and palmitic acid.29 Seeds also contain myristicic acid, hydroxy-methoxypsoralen, and umbelliferone. Diuresis may be due to the presence of glycolic acid Stalks may yield the photodynamically active principle bergapten. Per 100 g, the leaf is reported to contain 21 calories, 92.8 g HX), 1.4 g protein, 0.3 g fat, 4.2 total carbohydrate, 1.0 g fiber, 1.3 g ash, 62 mg Ca, 37 mg P, 2 5 mg Fe, 96 mg Na, 326 mg K, 1,040 μg beta-carotene equivalent, 0.06 mg thiamine, 0.07 mg riboflavin, 0.4 mg niacin, and 20 mg ascorbic acid. Garg et al.88 report 6 coumarins in the seeds, seselin, isoimperatorin, osthenol. bergapten, isopimpinellin, and the novel apigravin. Per 100 g, celery seed is reported to contain 392 calories (1,641 kJ), 6.6 g H2O, 18.1 g protein, 25.3 g fat, 41.4 g total carbohydrate, 11.8 g fiber, 9.3 g ash, 1,767 mg Ca, 547 mg P, 45 mg Fe, 440 mg Mg, 160 mg Na, 1,400 mg K, 6.9 mg Zn, 52 IU vitamin A, and 17.1 mg ascorbic acid. There are 60 mg phytosterol.89
Phytotherapeutic Agents in Epilepsy
Published in Vikas Kumar, Addepalli Veeranjaneyulu, Herbs for Diabetes and Neurological Disease Management, 2018
Isopimpinellin and byakangelicol are furocoumarins isolated from the fruits of H. crenatifolium (Apiaceae) having a C-8 substituent. Both these drugs have demonstrated good anticonvulsant potential against MES-induced seizures in mice.161
Alloimperatorin from Ammi majus fruits mitigates Piroxicam-provoked gastric ulcer and hepatorenal toxicity in rats via suppressing oxidative stress and apoptosis
Published in Biomarkers, 2022
Howaida I. Abd-Alla, Ghadha Ibrahim Fouad, Kawkab A. Ahmed, Kamel Shaker
Previous results on Ducrosia species displayed the high activity of furocoumarins isolated from the nonpolar extracts e.g., n-hexane and ethyl acetate extracts (Abd-Alla et al. 2016). The principal furanocoumarins including methoxsalen 2, imperatorin 5 and heraclin 3 and other coumarins of significance are isoimperatorin 4, heraclenin, and isopimpinellin (Balbaa et al. 1973; Abu-Mastafa et al. 1975; Hossain and Al Touby 2020). Imperatorin 5 and isoimperatorin 4 are the major furanocoumarins isolated from the dried root of Angelica dahuricae, the plant belongs to the same family of Ammi majus (Uto et al. 2015; Bai et al. 2021). Pharmacological and biochemical studies have indicated that heraclin 3 and isoimperatorin 4 have anti-inflammatory activity (Uto et al. 2015; Bai et al. 2021). Although evidence on other coumarinss’ related biological activities is great, it lacks information about Allo biological activities. Thereby, this study was conducted to investigate Allo’s potential activities in the liver, kidney, and gastric disorders. Another member of the 6, 7-furanocoumarin family-like alloimperatorin (6) is isoimperatorin (4), which is characterised by exerting anti-inflammatory and analgesic activities (Banikazemi et al. 2021). The anti-inflammatory properties of furocoumarins previously isolated from A. majus aerial parts (bishop’s weed) have been confirmed (Tanimoto et al. 2020). 6-hydroxy-7-methoxy coumarin and hydroxy-7-methoxy-4 methyl coumarin have shown high anti-inflammatory activity (Tanimoto et al. 2020).
Bioactivation of herbal constituents: mechanisms and toxicological relevance
Published in Drug Metabolism Reviews, 2019
Apart from CYP3A4 inactivation, several other linear or angular furanocoumarins were identified as mechanism-based inactivators of CYP2B6 including imperatorin (Zheng et al. 2014), isoimperatorin (Cao et al. 2015), psoralen (Ji et al. 2015), isopsoralen (Lu et al. 2016), with methoxsalen, bergapten, and isopimpinellin being mechanism-based inactivators of CYP2B1 (Cai et al. 1993; Koenigs and Trager 1998). Consistent with findings from bergamottin, GSH showed no or little protective effect on CYP2B inactivation. Additionally, mechanism-based inactivation of CYP2C9 by linderane, a naturally occurring furano sesquiterpenoid containing a 2,3-substituted furan, was also reported with kinact = 0.0419 min−1 and KI = 1.26 μM respectively (Wang, Wang, Mao, et al. 2015). In all cases, mechanism-based inhibition of CYP2B and CYP2C9 was attributed to metabolic activation of the 2,3-substituted furan to electrophilic furanoepoxide and/or γ-ketoenal which presumably alkylates apoprotein and/or heme of target isozymes. It’d be of interest to identify the amino acid residue(s) of cytochrome P450 enzymes as the modification target to understand the mechanism of such irreversible inactivation by these furanocoumarins.
The α-amylase and α-glucosidase inhibitory activities of the dichloromethane extracts and constituents of Ferulago bracteata roots
Published in Pharmaceutical Biology, 2018
Songül Karakaya, Sefa Gözcü, Zühal Güvenalp, Hilal Özbek, Hafize Yuca, Benan Dursunoğlu, Cavit Kazaz, Ceyda Sibel Kılıç
Previous phytochemical studies indicated that coumarins are the most common metabolites on Ferulago species (Jimenez et al. 2000). Coumarins have various biological activities such as anticancer (Lee et al. 2011; Luo et al. 2011), anti-inflammatory (Kwon et al. 2011; Huang et al. 2012), anticoagulant (Aoyama et al. 1992; Hirsh et al. 2001), antiadipogenic (Shin et al. 2010), antitubercular (Chiang et al. 2010), antihyperglycemic (Fort et al. 2000; Tchamadeu et al. 2010), antiviral (Venugopala et al. 2013), antifungal (Chou et al. 2007; Wang et al. 2009), antibacterial (Rosselli et al. 2009), antihypertensive (Crichton & Waterman, 1978; Gantimur et al. 1986), anticonvulsant (Luszczki et al. 2009), antioxidant (Kim et al. 2008; Basile et al. 2009), neuroprotective (Wang et al. 2012), and antidiabetic (Marles & Farnsworth 1995; Patel et al. 2012). This is the first report of isolation and structure elucidation study on the roots of F. bracteata to afford a new coumarin, peucedanol-2′-benzoate (1), along with nine known ones (2–10) and a sterol mixture (11–12). The α-amylase and α-glucosidase inhibitory activities of isolated coumarins were also evaluated. Coumarins may be a potential source of new antidiabetic agents and may also be used by peripheral tissues by improving insulin resistance and increasing glucose uptake (Zhang et al. 2017). Peucedanol 7-O-β-d-glucopyranoside (Lee et al. 2004), coumarin (1,2-benzopyrone) (Pari & Rajarajeswari 2009) umbelliferone (Ramesh & Pugalendi 2005), imperatorin (Adebajo et al. 2009), psoralen, 5-methoxypsoralen, 8-methoxypsoralen, isooxypeucedanin, pabulenol, oxypeucedanin methanolate, oxypeucedanin hydrate (Shalaby et al. 2014), isobergapten, pimpinellin, isopimpinellin, sphondin, scopoletin, phellopterin, byakangelicin and daucosterol (Zhang et al. 2017) were isolated from various plants belonging to the Apiaceae family and were found to be antidiabetic. So, this may be a significant approach in the treatment of type 2 diabetes. This study is a first report on the isolation and characterization of the bioactive compounds from root extracts of F. bracteata and also reports α-amylase and α-glucosidase inhibitory activities of this species.