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Apiaceae Plants Growing in the East
Published in Mahendra Rai, Shandesh Bhattarai, Chistiane M. Feitosa, Ethnopharmacology of Wild Plants, 2021
Sherweit El-Ahmady, Nehal Ibrahim, Nermeen Farag, Sara Gabr
Twelve polyacetylenes were isolated from carrot, where falcarinol, falcarindiol and falcarindiol-3-acetate are the essential ones predominately found in the roots. The other nine polyacetylenes isolated are: (E)-isofalcarinolone, falcarindiol-8-acetate, 1,2-dihydrofalcarindiol-3-acetate, (E)-falcarindiolone-8-acetate, (E)-falcarindiolone-9-acetate, 1,2-dihydrofalcarindiol, (E)-1-methoxyfalcarindiolone-8-acetate, (E)-1-methoxy-falcarindiolone-9-acetate, and panaxydiol (Schmiech et al. 2009, Dawid et al. 2015). Their distribution has been shown to be linked to the cultivars and the concentration of polyacetylenes found, maybe 10–20 times more in wild type of carrots than domesticated carrots (Pferschy-Wenzig et al. 2009, Dawid et al. 2015).
Herbal Cannabinomimetics
Published in Amritpal Singh Saroya, Reverse Pharmacology, 2018
Falcarinol is a fatty alcohol found in members of Apiaceae including carrots, parsley, and celery, and in Panax ginseng. Falcarinol has been isolated from Seseli praecox (Gamisans) Gamisans (Apiaceae), endemic to Sardinia.
The Phytocannabinoids
Published in Amritpal Singh Saroya, Contemporary Phytomedicines, 2017
Falcarinol (Fig. 32.19) is a fatty alcohol found in members of Apiaceae including carrots, parsley, and celery, and in Panax ginseng. Falcarinol was isolated from Seseli praecox, a plant endemic to Sardinia. Falcarinol exhibited binding affinity to both human CB receptors but selectively alkylates the anandamide binding site in the CB(1) receptor (K(i) = 594 nM), acting as covalent inverse agonist in CB(1) receptor-transfected CHO cells.In human HaCaT keratinocytes falcarinol resulted in increased expression of the pro-allergic chemokines IL-8 and CCL2/MCP-1 in a CB(1) receptor-dependent manner. Moreover, falcarinol inhibited the effects of anandamide (Fig. 32.20) on TNF-alpha stimulated keratinocytes. In vivo, falcarinol strongly aggravated histamine-induced oedema reactions in skin prick tests.The findings suggest anti-allergic effects of anandamide and that falcarinol- associated dermatitis is due to antagonism of the CB(1) receptor in keratinocytes, leading to increased chemokine expression and aggravation of histamine action (Leonti et al. 2010).
Devil’s Club Falcarinol-Type Polyacetylenes Inhibit Pancreatic Cancer Cell Proliferation
Published in Nutrition and Cancer, 2019
Susan S. C. Cheung, David Hasman, Djamel Khelifi, Joseph Tai, Richard W. Smith, Garth L. Warnock
Natural falcarinol-type (FC-type) polyacetylenes are present in many herbs and root crops, with FC being the most common of the C17 polyacetylenes found in carrot, celery, parsnip, and in several well-known medicinal herbs including ginseng (1). FC’s anticancer activity has been studied in Dendropanax arboreus (2), Saposhnikovae divaricata (3), celery (4), carrot (5), and Panax notoginseng (6). Presence of FC-type polyacetylenes has also been reported in the root bark (7) and inner stem (8) of Devil’s club (DC) Oplopanax horridus. Because of its presence in common vegetable groups, bioactivity studies of FC have largely focused on its antioxidant properties, health benefits, and chemoprevention aspects (9). Recently, it was observed that one of DC’s bioactive polyacetylenes, DCA (9,17-octadecadiene-12,14-diyne-1,11,16-triol,1-acetate), effectively inhibited human pancreatic cancer cell proliferation in monolayer as well as in spheroid culture (10,11). In addition, two other FC-type polyacetylenes, falcarindiol, and oplopantriol A, from DC were also reported to show potent growth inhibition of human breast and colon cancer cells (12–14). With the availability of synthetic protocols for compounds such as FC and 1,2-dihydrofalcarinol (FCH) (15), also known as panaxjapyne, this study investigated the antiproliferation activity of FC-type C17 polyacetylenes on human pancreatic cancer cell lines using synthetic instead of isolated compounds.
Therapeutic potential of Panax ginseng and its constituents, ginsenosides and gintonin, in neurological and neurodegenerative disorders: a patent review
Published in Expert Opinion on Therapeutic Patents, 2019
Arezoo Rajabian, Maryam Rameshrad, Hossein Hosseinzadeh
Generally, there are two major groups of ginsenosides based on their chemical structures, namely, the Rb group (protopanaxadiols [PPDs] including Rb1, Rb2, Rc, Rd, Rg3, Rh2, and Rh3) containing sugar moieties attached to OH at C-3 and/or C-20, Rg group (protopanaxatriols (PPT) including Re, Rf, Rg1, Rg2, and Rh1) containing sugar moieties attached to OH at C-3, C-6, and/or C-20 (Figure 3) [19]. Ginsenosides comprise about 50% of the crude ginseng total saponin [20]. Pentacyclic ginsenosides including oleanolic acid-type Ro ginsenoside (24-(R)-pseudoginsenoside F11) have been also detected in P. ginseng. Apart from ginsenosides, ginseng also contains polyacetylenes, polysaccharides, phytosterols, sesquiterpenes, flavonoids, and phenolic compounds that have exhibited biological activities (Figure 2) [19]. Polyacetylenic compounds (panaxynol (falcarinol-type) and panaxydol) have been cited in several studies as the active compounds involved in the anticancer, antimicrobial, and inflammatory properties of P. ginseng. Phenolic compounds including salicylic acid, vanillic acid, and maltol as well as flavonoids displayed antioxidant and anticancer effects [21]. Phytosterols can lower the cholesterol levels [19].
Therapeutic potentials of endophytes for healthcare sustainability
Published in Egyptian Journal of Basic and Applied Sciences, 2021
Ayodeji O. Falade, Kayode E. Adewole, Temitope C. Ekundayo
Cancer research efforts have undoubtedly, yielded positive results as a wide range of natural anticancer compounds have been isolated from different sources including endophytes. Taxol, a popular chemotherapy drug used in cancer treatments, has been isolated from a number of endophytes hosted by plants belonging to Taxus and Taxodium genera [22–24]. Other taxol-producing endophytic fungi include Pestalotiopsis versicolor and Pestalotiopsis neglecta [25]. The toxic effect of taxol on various cancer cell lines, including BT220, HEPG2, HLK 210, MCF7, Int 407, HI 16 and HL 251, have been reported [26,27]. Deoxypodophyllotoxin, another anticancer agent, has been isolated and purified from an endophytic Aspergillus strain [28]. Deoxypodophyllotoxin is used as a pro-drug in the management of cancer. Ding et al. [29] isolated a cytotoxic alkaloid, chaetoglobosin U from an endophytic fungus belonging to Chaetomium genus. The authors confirmed that the bioactive compound ‘chaetoglobosin U’ had toxic effect on ‘human nasopharyngeal epidermoid tumor KB cell line’ with the inhibitory rate correlating with that of the positive control [5-fluorouracil) [30]. A different study by 99, reported the isolation of falcarinol from a Paecilomyces species hosted by Panax ginseng. It is noteworthy that Paecilomyces falcarinol exhibited remarkable in vitro antitumor effect against different cell lines [30]. Also, anthracenedione derivatives separated from endophytic fungal strains belonging to Guignardia and Halorosellinia genera inhibited proliferation of KB and KBv200 cells via apoptotic-related mechanisms [31].