Cannabis Phenolics and their Bioactivities

Pollastro, Federica; Minassi, Alberto; Fresu, Luigia Grazia

doi:10.2174/0929867324666170810164636

Cited by 130 publications

(143 citation statements)

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“…Even though the attention of the scientific community has been focused on major phytocannabinoids, the phytochemical characterization of C. sativa highlights the presence of various non-cannabinoids constituents including flavonoids [15]. Their characterization is scarce and random, especially when the inflorescences of industrial hemp are concerned [13,16,17].…”

Section: Introductionmentioning

confidence: 99%

Influence of Altitude on Phytochemical Composition of Hemp Inflorescence: A Metabolomic Approach

et al. 2020

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The phytochemical profiling of hemp inflorescences of clonal plants growing in different conditions related to altitude was investigated. Four strains of industrial hemp (Cannabis sativa L., family Cannabaceae) of Kompolti variety were selected and cloned to provide genetically uniform material for analyses of secondary metabolites (terpenes, cannabinoids, and flavonoids) at two different elevations: mountain (Alagna Valsesia 1200 m ASL) and plains (Vercelli Province 130 m ASL). Environmental conditions influenced by elevation have proven to be important factors inducing variations in hemp inflorescences’ secondary metabolite composition. In fact, all plants grown at altitude exhibited a higher total amount of terpenes when compared with plains counterparts, with β-Myrcene, trans-Caryophyllene and α-Humulene as the main contributors. A metabolomic, un-targeted approach performed by HPLC-Q-Exactive-Orbitrap®-MS platform with subsequent data processing performed by Compound Discoverer™ software, was crucial for the appropriate recognition of many metabolites, clearly distinguishing mountain from plains specimens. Cannabidiolic acid CBDA was the most abundant phytocannabinoid, with significantly higher concentrations in the mountain samples. The metabolic pathway of CBGA (considered as the progenitor/precursor of all cannabinoids) was also activated towards the production of CBCA, which occurs in considerably 3 times higher quantities than in the clones grown at high altitude. Isoprenoid flavones (Cannaflavins A, B, and C) were correspondingly upregulated in mountain samples, while apigenin turned out to be more abundant in plains samples. The possibility to use hemp inflorescences in pharmaceutical/nutraceutical applications opens new challenges to understand how hemp crops respond in terms of secondary metabolite production in various environments. In this regard, our results with the applied analytical strategy may constitute an effective way of phytochemical profiling hemp inflorescences.

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Section: Introductionmentioning

confidence: 99%

Influence of Altitude on Phytochemical Composition of Hemp Inflorescence: A Metabolomic Approach

et al. 2020

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“…However, its cannabinoids content is considered to be negligible if compared to other known varieties. The complete review of Pollastro et al [20] reported different cannabis phenolics and their bioactivity but research works dealing with occurrence and amount of different phenolic constituents in several cannabis varieties or cultivars are lacking. A recent work described the chemical profiling of medical cannabis extracts but with focus on cannabinoid derivatives.…”

Section: Introductionmentioning

confidence: 99%

Chemical Characterization of Leaves, Male and Female Flowers from Spontaneous Cannabis (Cannabis sativa L.) Growing in Hungary

Nagy

Cianfaglione

Maggi

et al. 2019

Chemistry & Biodiversity

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Spontaneous forms of hemp (Cannabis sativa L., often reported as Cannabis sativa var. spontanea Vavilov) with a low content of psychoactive cannabinoids can be considered as a valuable source of other phytoconstituents to be used in nutraceuticals or for their health promoting properties. Chemical data on this hemp variety are rather scarce. In this article, we report a comprehensive phytochemical characterization of leaves, male and female inflorescences of C. sativa growing wild in Hungary. For the purpose, the essential oil along with polar extracts were analyzed using GC/MS, NMR and LC‐DAD‐MS techniques, respectively. The results indicated that female inflorescence essential oil contains high amounts of the CB2 agonists, (E)‐caryophyllene (28.3 %) and cannabidiol (CBD; 24.9 %), whereas leaves and male inflorescence essential oils contained lower amounts of both compounds. HPLC/MS allowed to quantify cannabidiol (CBD) and cannabidiolic acid (CBD−A) in the ethyl acetate extracts from leaves, male and female inflorescences; they were 0.3, 0.8 and 0.9 %, and 0.2, 0.3 and 0.4 %, respectively. Flavonoids of this spontaneous form of hemp were formed by C‐glycosides and glucuronic acids of kaempferol and apigenin with a total content of 3.8, 6.1 and 7.8 mg/g in methanolic extracts from leaves, male and female inflorescences, respectively. Based on these results, spontaneous C. sativa may represent an important source of CB2 agonists and bioflavonoids to be used in nutraceuticals, cosmetics and pharmaceuticals.

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“…Cannabis sativa produces more than 480 chemicals, which represent almost all of the different biogenetic classes (ElSohly and Slade, ), including cannabinoids (Pollastro et al, ) and typical terpeno‐phenolic compounds, in addition to a surplus of noncannabinoid second metabolites, such as prenylated flavonoids, stilbenoid derivatives, and lignanammides. Twenty‐six flavonoids have been detected in cannabis plants (ElSohly and Slade, ; Pollastro et al, ). Cannabis phenolics possess anti‐inflammatory properties: They inhibit prostaglandin E2 production by cultured rheumatoid synovial cells (Barrett et al, ).…”

Section: Introductionmentioning

confidence: 99%

Effect of Solvent, Preheating Temperature, and Time on the Ultrasonic Extraction of Phenolic Compounds from Cold‐Pressed Hempseed Cake

Liang

Zago

Nandasiri

et al. 2018

J Americ Oil Chem Soc

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The effect of different solvents (aqueous methanol [70%, v/v], aqueous acetone [80%, v/v], and a solvent mixture [MA] of aqueous methanol [70%, v/v] and aqueous acetone [70%, v/v] in a ratio of 1:1 [v/v]), preheating temperatures (140, 160, and 180 C), and times of exposure (5, 15, and 30 min) on the ultrasonic extraction of the main phenolic compounds from hempseed cake (Cannabis sativa) was investigated. A simplified new high-performance liquid chromatography (HPLC) method was developed to identify and quantify the main phenolics (namely, N-transcaffeoyltyramine and cannabisin B) in the extracts. Two other main compounds, numbered 3 and 4, were also detected. The results showed that the nature of the extracting solvent had a significant (P < 0.05) impact on the ultrasonic extraction of phenolic compounds. The acetone extracts exhibited the highest total phenolic content (TPC), followed by MA and methanol. The preheating temperature and time of exposure enhanced the TPC for all solvents examined. The main phenolics, N-trans-caffeoyltyramine, cannabisin B, and compound 3, were positively affected by the temperature and time of exposure, irrespective of the solvents used. In sharp contrast, compound 4 appeared to be thermally sensitive: increasing preheating time and temperature decreased the yields of this compound. This study demonstrated that acetone was the most effective extracting solvent and that preheating enhanced the yield of the main phenolics.

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Cannabis Phenolics and their Bioactivities

Cited by 130 publications

References 0 publications

Influence of Altitude on Phytochemical Composition of Hemp Inflorescence: A Metabolomic Approach

Influence of Altitude on Phytochemical Composition of Hemp Inflorescence: A Metabolomic Approach

Chemical Characterization of Leaves, Male and Female Flowers from Spontaneous Cannabis (Cannabis sativa L.) Growing in Hungary

Effect of Solvent, Preheating Temperature, and Time on the Ultrasonic Extraction of Phenolic Compounds from Cold‐Pressed Hempseed Cake

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