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Terpenes: A Source of Novel Antimicrobials, Applications and Recent Advances
Published in Mahendra Rai, Chistiane M. Feitosa, Eco-Friendly Biobased Products Used in Microbial Diseases, 2022
Nawal M. Al Musayeib, Amina Musarat, Farah Maqsood
Cannabinoids are a C21 terpene phenolic group of compounds, including their analogs and transformation products, predominantly isolated from cannabis plants (Elsohly and Slade 2005). They are detected in different parts of these plants; however, they are largely found in the secretory cavity of the glandular trichomes of the female flowers (Andre et al. 2016). Cannabinoids are biosynthesized in their carboxylated form (acid forms) in fresh cannabis plant while during storage and smoking, they are non-enzymatically decarboxylated into their neutral forms. Cannabinoids can be categorized into 11 major structural types, including, Δ8-tetrahydrocannabinol, Δ9-tetrahydrocannabinol, cannabigerol, cannabidiol, cannabichromene, cannabinodiol, cannabielsoin, cannabinol, cannabicyclol, cannabitriol and miscellaneous types The first study addressing the quantification of antimicrobial effect of the pure cannabinoids (Δ9-tetrahydrocannabinol and cannabidiol) isolated from C. sativa was conducted by VanKlingeren and Ten Ham in 1976. They entrenched a bactericidal and bacteriostatic effect of Δ9-tetrahydrocannabinol and cannabidiol against S. aureus and Streptococcus spp. in the range of 1–5 μg mL–1, but found no effects towards Gram-negative bacteria. They also showed a decrease in antibiotic activity in the presence of horse serum (Van Klingeren et al. 1976).
Chemistry of Cannabis indica
Published in Amritpal Singh Saroya, Reverse Pharmacology, 2018
Cannabinoids, a class of meroterpenoids derived from the alkylation of an olivetol- like alkyl resorcinol with a monoterpene unit, are the most typical constituents of Cannabis. This class includes over a hundred members belonging to several structural types, mainly differing by the constitution of their terpenoid moiety (Makriyannis and Rapaka 1987; Appendino and Taglialatela-Scafat 2013). Each of the 113 cannabinoid compounds falls within one of six different subclasses. These six cannabinoid subclasses include:Tetrahydrocannabinols (THCs)Cannabierols (CBGs)Cannabinodiols and cannabinols (CBDL and CBNs)Cannabidiols (CBDs)Cannabichromenes (CBCs)Miscellaneous cannabinoids - cannabitriol (CBT), cannabicyclol (CBL),cannabielsoin (CBE) and others.
The Phytocannabinoids
Published in Amritpal Singh Saroya, Contemporary Phytomedicines, 2017
Cannabinoids, a class of meroterpenoids derived from the alkylation of an olivetol- like alkyl resorcinol with a monoterpene unit, are the most typical constituents of Cannabis. This class includes over a hundred members belonging to several structural types, mainly differing by the constitution of their terpenoid moiety (Makriyannis and Rapaka 1987; Appendino and Taglialatela-Scafat 2013). Each of the 113 cannabinoid compounds falls within one of six different subclasses. These six cannabinoid subclasses include:Tetrahydrocannabinols (THCs)Cannabierols (CBGs)Cannabinodiols and cannabinols (CBDL and CBNs)Cannabidiols (CBDs)Cannabichromenes (CBCs)Miscellaneous cannabinoids—cannabitriol (CBT), cannabicyclol (CBL), cannabielsoin (CBE), and others.
Cannabis and cannabinoid drug development: evaluating botanical versus single molecule approaches
Published in International Review of Psychiatry, 2018
Marcel O. Bonn-Miller, Mahmoud A. ElSohly, Mallory J. E. Loflin, Suman Chandra, Ryan Vandrey
This section provides an important background with respect to important definitions, nomenclature, and pharmacology that will be referenced later. The cannabis plant has been shown to be chemically rich, with 565 known constituents belonging to 23 classes of compounds (ElSohly & Gul 2014; ElSohly & Slade, 2005; Radwan, Wanas, Chandra, & ElSohly. 2017). Perhaps the most recognized class of compounds in cannabis are the namesake cannabinoids. At the time of this writing, 120 different phytocannabinoids, plant-derived molecules unique to cannabis, have been identified in the cannabis plant, many of which directly modulate the endogenous cannabinoid system. These naturally occurring cannabinoids are distributed among 10 sub-classes, including Δ9- and Δ8-THC, cannabidiol (CBD), cannabigerol (CBG), cannabinol (CBN), Cannabinodiol (CBND), cannabielsoin (CBE), cannabicyclol (CBL), cannabitriol (CBT), and miscellaneous type (30 known). THC is produced as an acid (Δ9-Tetrahydrocannabinolic acid, Δ9-THCA) in the glandular trichomes of the leaves and inflorescence bracts of the plant and undergoes decarboxylation with age or heating to form Δ9-THC (Turner, ElSohly, & Boeren, 1980). THC is typically the most abundant chemical constituent of the cannabis flower, and is by far the most studied and well-understood cannabinoid. However, cannabinoids are not the only active components of cannabis. Other constituents that might contribute in some way to the effects of cannabis include Terpenes (120 known); Nitrogenous compounds (33 known); Amino acids (18 known); Proteins, enzymes, and glycoproteins (11); Sugars and related compounds (34); Hydrocarbons (50 known); Simple alcohols (7 known); Simple aldehydes (12 known); Simple ketones (13 known); Simple acids (20 known); Fatty acids (27 known); Simple esters and lactones (13 known); Steroids (15 known); Non-cannabinoid phenols (25 known); Flavonoids (27 known); Vitamins (1 known); Pigments (2 known); Elements (9 known); Phenanthrenes (4 known); Spiroindans (2 known); Xanthones (1 known), and Biphenyls (1 known).