Terpenes/Terpenoids in Cannabis: Are They Important?

Cannabis sativa plant has not only cannabinoids as crucial compounds but also the other compounds that play important role as synergistic and/or entourage compound. Cannabis/hemp plant materials and essential oils were analyzed with the help of gas chromatography/mass spectrometry detector for the content of terpenes and terpenoids. The main terpenes/terpenoids and their abundance in the samples were evaluated. Results of this study will be helpful in the next evaluation of these compound in mixture with cannabinoids and their importance in medical treatment.

Cannabis for the treatment of paediatric epilepsy? An update for Canadian paediatricians.

The plant Cannabis sativa produces over 140 known cannabinoids. These chemicals generate considerable interest in the medical research community for their possible application to several intractable disease conditions. Recent reports have prompted parents to strongly consider Cannabis products to treat their children with drug resistant epilepsy. Physicians, though, are reluctant to prescribe Cannabis products due to confusion about their regulatory status and limited clinical data supporting their use. We provide the general paediatrician with a brief review of cannabinoid biology, the literature regarding their use in children with drug resistant epilepsy, the current Health Canada and Canadian Paediatric Society recommendations and also the regulations from the physician regulatory bodies for each province and territory. Given the complexities of conducting research on Cannabis products for children with epilepsy, we also discuss outstanding research objectives that must be addressed to support Cannabis products as an accepted treatment option for children with refractory epilepsy.

The Anti-Inflammatory Properties of Terpenoids from Cannabis.

Introduction: Cannabinoids are well known to have anti-inflammatory effects in mammalians; however, the Cannabis plant also contains other compounds such as terpenoids, whose biological effects have not yet been characterized. The aim of this study was to compare the anti-inflammatory properties of terpenoids with those of cannabidiol (CBD). Materials and Methods: Essential oils prepared from three monoecious nonpsychoactive chemotypes of Cannabis were analyzed for their terpenoid content and subsequently studied pharmacologically for their anti-inflammatory properties in vitro and in vivo. Results: In vitro, the three essential oils rich in terpenoids partly inhibited reactive oxygen intermediate and nitric oxide radical (NO•) production in RAW 264.7 stimulated macrophages. The three terpenoid-rich oils exerted moderate anti-inflammatory activities in an in vivo anti-inflammatory model without affecting tumor necrosis factor alpha (TNFα) serum levels. Conclusions: The different Cannabis chemotypes showed distinct compositions of terpenoids. The terpenoid-rich essential oils exert anti-inflammatory and antinociceptive activities in vitro and in vivo, which vary according to their composition. Their effects seem to act independent of TNFα. None of the essential oils was as effective as purified CBD. In contrast to CBD that exerts prolonged immunosuppression and might be used in chronic inflammation, the terpenoids showed only a transient immunosuppression and might thus be used to relieve acute inflammation.

Phytocannabinoids: a unified critical inventory.

Covering up to January 2016Cannabis sativa L. is a prolific, but not exclusive, producer of a diverse group of isoprenylated resorcinyl polyketides collectively known as phytocannabinoids. The modular nature of the pathways that merge into the phytocannabinoid chemotype translates in differences in the nature of the resorcinyl side-chain and the degree of oligomerization of the isoprenyl residue, making the definition of phytocannabinoid elusive from a structural standpoint. A biogenetic definition is therefore proposed, splitting the phytocannabinoid chemotype into an alkyl- and a ß-aralklyl version, and discussing the relationships between phytocannabinoids from different sources (higher plants, liverworts, fungi). The startling diversity of cannabis phytocannabinoids might be, at least in part, the result of non-enzymatic transformations induced by heat, light, and atmospheric oxygen on a limited set of major constituents (CBG, CBD, Δ9-THC and CBC and their corresponding acidic versions), whose degradation is detailed to emphasize this possibility. The diversity of metabotropic (cannabinoid receptors), ionotropic (thermos-TRPs), and transcription factors (PPARs) targeted by phytocannabinoids is discussed. The integrated inventory of these compounds and their biological macromolecular end-points highlights the opportunities that phytocannabinoids offer to access desirable drug-like space beyond the one associated to the narcotic target CB1.

Pharmacological and therapeutic secrets of plant and brain (endo)cannabinoids.

Research on the chemistry and pharmacology of cannabinoids and endocannabinoids has reached enormous proportions, with approximately 15,000 articles on Cannabis sativa L. and cannabinoids and over 2,000 articles on endocannabinoids. The present review deals with the history of the Cannabis sativa L. plant, its uses, constituent compounds and their biogeneses, and similarity to compounds from Radula spp. In addition, details of the pharmacology of natural cannabinoids, as well as synthetic agonists and antagonists are presented. Finally, details regarding the pioneering isolation of the endocannabinoid anandamide, as well as the pharmacology and potential therapeutic uses of endocannabinoid congeners are presented.

Identification of cyclopropyl fatty acids in walnut (Juglans regia L.) oil.

AIM: Identification of cyclopropyl fatty acids in walnut oil. METHOD: GC/MS method was developed for the determination of eight cyclopropyl fatty acids in walnut (Juglans regia) oil. RESULTS: Monocyclopropane acids: methyl 9-cyclopropyl-nonanoate, 6,7-methylene-, 8,9-methylene-, 9,10-methylene-, 11,12-methylene octadecanoates, and dicyclic acid - methyl 9,10,12,13-dimethylene octadecanoate, tricyclic acid - methyl 9,10,12,13,15,16-trimethylene octadecanoate, and unsaturated - methyl 2-octylcyclopropene-1-octanoate were detected in walnut oil by GC-MS and their mass spectra studied. Four cyclic fatty acids were identified for the fist time in seed oils. CONCLUSIONS: Eight cyclopropyl fatty acids were detected in the Mediterranean nuts for the first time.

Biodiversity of the chemical constituents in the epiphytic lichenized ascomycete Ramalina lacera grown on difference substrates Crataegus sinaicus, Pinus halepensis, and Quercus calliprinos.

AIM: The identification and evaluation of lichen metabolite production by the epiphytic lichenized ascomycete Ramalina lacera collected from different substrates: Crataegus sinaicus, Pinus halepensis, and Quercus calliprinos. METHODS: Chemical constituents were characterized by GC MS, HPLC, HR TLC, and other chemical methods. RESULTS: The most abundant fatty acids were alpha-linolenic acid, oleic acid, and palmitic acid but a considerable variability of the ester composition from one to another was found. A comparison of neutral lipids, glycolipids, polar lipids and fatty acid composition of the tree growing lichen Ramalina lacera was done. Diacylglyceryl N,N,N trimethylhomoserine, diaclyglycerylhydroxymethyl N,N,N trimethyl beta alanine, phosphatidylcholine, and phosphatidylinositol were found as major components among polar lipids. Diffractaic, lecanoric, norstictic, protocetric, and usnic acids were isolated as major aromatic compounds in all samples of R. lacera. CONCLUSIONS: We evaluated a diversity of fatty acids, lipids, and aromatic compounds produced by the samples of Ramalina lacera growing on different tree substrates, Crataegus sinaicus, Pinus halepensis and Quercus calliprinos.

Ascaridole and related peroxides from the genus Chenopodium.

AIM: Detection of monoterpenoid ascaridole and other terpenoids in the genus Chenopodium from the East Mediterranean. METHOD: Distribution of ascaridole in leaves of 13 species medicinal plant belonging to the genus Chenopodium was examined with the help of the GC MS method. RESULTS: cis Ascaridole was found as a major peroxy monoterpenoid (up to 46.9 %) in the oil. Three minor isomers: cis isoascaridole (1.1 6.4 %), trans ascaridole (1 2 %), and trans isoascaridole (1 2 %) were also detected. The biological activities and biosynthesis of ascaridole are further discussed. CONCLUSIONS: The results on Ascaridol and the major volatiles and semi volatiles of wild species belonging to the genus Chenopodium provide important information on biologically active monoterpenoid compounds and volatile metabolites biosynthesized in wild medicinal plants growing in the East Mediterranean.