Abstract
Phytocannabinoids are a structurally diverse class of bioactive naturally occurring compounds found in angiosperms, fungi, and liverworts and produced in several plant organs such as the flower and glandular trichrome of Cannabis sativa, the scales in Rhododendron, and oil bodies of liverworts such as Radula species; they show a diverse role in humans and plants. Moreover, phytocannabinoids are prenylated polyketides, i.e., terpenophenolics, which are derived from isoprenoid and fatty acid precursors. Additionally, targeted productions of active phytocannabinoids have beneficial properties via the genes involved and their expression in a heterologous host. Bioactive compounds show a remarkable non-hallucinogenic biological property that is determined by the variable nature of the side chain and prenyl group defined by the enzymes involved in their biosynthesis. Phytocannabinoids possess therapeutic, antibacterial, and antimicrobial properties; thus, they are used in treating several human diseases. This review gives the latest knowledge on their role in the amelioration of abiotic (heat, cold, and radiation) stress in plants. It also aims to provide synthetic and biotechnological approaches based on combinatorial biochemical and protein engineering to synthesize phytocannabinoids with enhanced properties.
Highlights
Phytocannabinoids are meroterpenoids bearing a resorcinol core with an isoprenyl, alkyl, or aralkyl para-positioned side chain, or alkyl group usually containing an odd number of carbon atoms—cannabinoids that have an even number of carbon atoms in the side chain are rare
Phytocannabinoids are bioactive naturally occurring terpenoids that were earlier thought to be exclusive to C. sativa but have been produced in Rhododendron species, some legumes, the liverwort genus Radula, and some fungi
Bioactive phytocannabinoids show remarkable non-hallucinogenic biological properties determined by the variable nature of the side chain and prenyl group defined by the enzymes involved in their biosynthesis
Summary
Phytocannabinoids are meroterpenoids bearing a resorcinol core with an isoprenyl, alkyl, or aralkyl para-positioned side chain, or alkyl group usually containing an odd number of carbon atoms—cannabinoids that have an even number of carbon atoms in the side chain are rare. From C. sativa more than 113 phytocannabinoids were isolated and classified into several groups such as cannabidiols (CBDs), cannabigerols (CBGs), cannabicyclols (CBLs), cannabidiols (CBNDs), cannabinols (CBNs), cannabitriols (CBTs), cannabichromenes (CBCs), (−)-∆9 -trans-tetrahydrocannabinol (∆9 -THC) and miscellaneous cannabinoids [1,3,4,5]. In C. sativa, CBD, CBG, CBC, cannabichromevarine (CBCV), and ∆9 -THC are the most abundant cannabinoids in their respective acidic form. The conversion mainly occurs due to the poor oxidative stability of phytocannabinoids, especially with the alkyl group. Plants 2021, 10, 1307 poor oxidative stability of phytocannabinoids, especially with the alkyl group. Biginosum native to Southwest China, and Rh. anthopogonoides grown in Southern China, eastern rubiginosum var. Rh. anthopogonoides in Southern China all generate native active monoterpenoids that have a cannabinoid backbone.grown.
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