Читать книгу Secondary Metabolites of Medicinal Plants - Bharat Singh - Страница 61

Cannabis sativa L. (Fam. – Cannabaceae) is an annual herbaceous plant and indigenous to Central Asia and India subcontinent. The phytochemicals in this plant species are secreted by the glandular trichomes found on the calyx and bracts of flowers. The Cannabis plant is used in the treatment of nausea and vomiting during chemotherapy; it also recommended to treat chronic pain and muscle spasms and central nervous system (CNS) and as anti-inflammatory (Li 1973; Gubellini et al. 2002; Brotchie 2003; Johnson et al. 2009; Radwan et al. 2009; Styrczewska et al. 2012; Tabrez et al. 2012; Borgelt et al. 2013; Whiting et al. 2015), as well as Parkinson's disease (Pisani et al. 2005, 2010, 2011). Based on the 2500-year-old ancient reports unearthed in the Turpan district in Xinjiang, China, it was concluded that Cannabis plant was used for ancient customs/rituals and in medicines (Jiang et al. 2006; Manduca et al. 2012; Radwan et al. 2015). Cannabigerol and olivetol are bound into tetrahydrocannabinol and other neutral cannabinoids (Kajima and Piraux 1982; Elzinga et al. 2015).

The toxicity levels of glutamate were reduced significantly by cannabidiol and by antioxidant compounds because several cannabinoids demonstrated antioxidant effects. Cannabidiol and tetrahydrocannabidiol also were shown to prevent hydroperoxide-induced oxidative damage as well as or better than other antioxidants in neuron cell cultures (Hampson et al. 1998; Radwan et al. 2008, 2015; Aizpurua-Olaizola et al. 2014). Due to differences in terpenoid composition, the cultivars of the two drug biotypes may exhibit distinctive medicinal properties (Hillig 2004). A cell suspension culture of C. sativa L. can convert cannabidiol to bound cannabielsoin and Δ-9-tetrahydrocannabinol to cannabicoumaronon (Braemer and Paris 1987; Choi et al. 2004; Fischedick et al. 2010b). Geranyl diphosphate and olivetolic acid are considered as specific intermediates in the cannabinoid biosynthesis (Fellermeier et al. 2001).

The cannabichromenic acid synthase enzyme catalyzes the oxidocyclization of cannabigerolic acid and cannabinerolic acid to cannabichromenic acid. It was interpreted that cannabichromenic acid is synthesized from cannabigerolic acid rather than cannabinerolic acid. In this reaction, the enzyme did not require any molecular oxygen or hydrogen peroxide; this indicates that cannabichromenic acid synthase reaction was completed by dehydrogenation without hydroxylation (Shoyama et al. 1968; Morimoto et al. 1998; Giacoppo et al. 2014; Nascimento et al. 2015). The cannabinoids isolated from the resin of these sessile glands induced cell death in leaves and cell suspension cultures. But when the cells were pretreated with cyclosporine A before the transfer of these cells in cell culture medium, then these cells survived. The DNA degradation was also performed by cannabinoid treatment in suspension of cells. The cannabinoids can lead to necrosis of cells via dysfunction of mitochondria during suspension of cells of C. sativa (Morimoto et al. 1998; Morimoto et al. 2007). The 10-Oxo-Δ^6a(10a)-tetrahydrocannabinol, cannabiglendol, Δ⁷-isotetrahydrocannabinol, and cannabicitran have been isolated from Cannabis (Flores-Sanchez and Verpoorte 2008).

Cannabis sativa pollen grains were investigated for the presence of flavonoid glycosides (kaempferol 3-O-sophoroside and quercetin 3-O-sophoroside) and cannabinoids (Δ⁹-tetrahydrocannabiorcol, cannabidivarin, cannabicitran, Δ⁹-tetrahydrocannabivarin, cannabicyclol, cannabidiol, cannabichromene, Δ⁹-tetrahydrocannabinol, cannabigerol, cannabinol, dihydrocannabinol, cannabielsoin, 6a,7,10a-trihydroxytetrahydrocannabinol, 9,10-epoxycannabitriol, cannabinol, cannabitriol, cannabigerovarinic acid A, cannabinodiol, 10-O-ethylcannabitriol, (−)-(9R,10R)-trans-10-O-ethylcannabitriol and 7,8-dehydro-10-O-ethylcannabitriol, cannabicyclol, cannabinerolic acid, (+)-cannabichromenic acid, cannabichromevarin, cannabigerovarin, tetrahydrocannabiorcol, cannabifuran, dehydrocannabifuran, cannabichromanone-C3, cannabichromanone-C5, cannabicyclolic acid, cannabicyclovarin, cannabigerolic acid A, (−)-cannabitetrol) from the methanolic extract (ElSohly et al. 1977, 1984; Grote and Spiteller 1978a,1978b; Turner et al. 1981; Hartsel et al. 1983; Ross and ElSohly 1995; Yamaguchi et al. 1995; ElSohly and Slade 2005; Ross et al. 2005; Hanuš et al. 2016). The cannabielsoin acid, cannabinolic acid, orientin, cannabisin A, Δ⁹-tetrahydrocannabinolic acid, cannabigerolic acid, 11-hydroxy-Δ⁹-tetrahydrocannabinolic acid A, (±)-6,7-cis/trans-epoxycannabigerolic acid, 8-keto-Δ⁹-tetrahydrocannabinolic acid A, cannabidivarinic acid, 8β,11-bis-hydroxy-Δ⁹-tetrahydrocannabinolic acid, cannabidiolic acid, anandamide, and (−)-7R-cannabicourmaronic acid have been reported from Cannabis extracts (Mackie et al. 1993; Mahlberg and Kim 2004; Ahmed et al. 2008, 2015; Galal et al. 2009; Fischedick et al. 2010a; Happyana et al. 2013; Giacoppo et al. 2014; Lewis et al. 2017).