Cannabidiol and Contributions of Major Hemp Phytocompounds to the “Entourage Effect”; Possible Mechanisms

Nahler, Gerhard

doi:10.24966/acim-7562/100066

Cited by 27 publications

(31 citation statements)

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“…Hemp “strain” is a common term in the U.S. to describe chemotype of hemp, or selection line that was not yet officially registered; there are hundreds of strains with names like cultivars, some are called “varieties” [ 37 ]. However, some authors argue it was inappropriate term to describe chemotypes, as this term is used for bacteria and viruses but not for plants [ 12 ]. Limonene, monocyclic monoterpene, is found in all types of hemp, it is one of the signature compounds in marijuana headspace [ 33 ].…”

Section: Resultsmentioning

confidence: 99%

“…The pharmacological power of hemp depends on the content of Δ9-tetrahydrocannabinolic acid (THCA) and cannabidiolic acid (CBDA) [ 9 , 10 ], but also on terpenes entourage effects [ 2 , 11 , 12 ]. Other major cannabinoids include cannabinolic acid (CBNA), cannabigerolic acid (CBGA), cannabichromenic acid (CBCA) and cannabinodiolic acid (CBNDA) [ 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

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Grinding and Fractionation during Distillation Alter Hemp Essential Oil Profile and Its Antimicrobial Activity

et al. 2020

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The hypothesis of this study was that we can modify the essential oil (EO) profile of hemp (Cannabis sativa L.) and obtain fractions with differential composition and antimicrobial activity. Therefore, the objective was to evaluate the effects of grinding of hemp biomass before EO extraction and fractionation during distillation on EO profile and antimicrobial activity. The study generated a several EO fractions with a diversity of chemical profile and antimicrobial activity. The highest concentrations of β-pinene and myrcene in the EO can be obtained in the 5–10 min distillation time (DT) of ground material or in the 80–120 min DT of nonground material. High δ-3-carene and limonene EO can be obtained from 0–5 min DT fraction of nonground material. High eucalyptol EO can be sampled either in the 0–5 min DT of the ground material or in the 80–120 min of nonground material. Overall, the highest concentrations of β-caryophyllene, α-(E)-bergamotene, (Z)-β-farnesene, α-humulene, caryophyllenyl alcohol, germacrene D-4-ol, spathulenol, caryophyllene oxide, humulene epoxide 2, β-bisabolol, α-bisabolol, sesquiterpenes, and cannabidiol (CBD) can be obtained when EO is sampled in the 80–120 min DT and the material is nonground. Monoterpenes in the hemp EO can be increased twofold to 85% by grinding the material prior to distillation and collecting the EO in the first 10 min. However, grinding resulted in a slight but significant decrease in the CBD concentration of the EO. CBD-rich oil can be produced by collecting at 120–180 min DT. Different EO fractions had differential antimicrobial activity. The highest antimicrobial activity of EO fraction was found against Staphylococcus aureus subsp. aureus. THC-free EO can be obtained if the EO distillation is limited to 120 min. The results can be utilized by the hemp processing industry and by companies developing new hemp EO-infused products, including perfumery, cosmetics, dietary supplements, food, and pharmaceutical industries.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Grinding and Fractionation during Distillation Alter Hemp Essential Oil Profile and Its Antimicrobial Activity

et al. 2020

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“…Cannabidiolic acid (CBDA), being a C3 -carboxyl derivative of CBD (2,4-dihydroxy-3-[(1R, 6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-[alpha]-6-pentylbenzoic acid), acts as a selective COX2 and prostaglandin endoperoxide synthase inhibitor and exhibits anti-inflammatory properties in human breast cancer cells [113]. It has been suggested that its action may be due to a weak affinity for CB1 and CB2 receptors ( Table 2) [114]. Similarly, other CBD derivatives, such as cannabidivarin (CBDV), which is a CBD analogue of C4 -propyl (2-[(1R, 6R)-3-methyl-6-prop-1-en-2)-ylcyclohex-2-en-1-yl]-5-propylbenzene-1,3-diol), 7-hydroxy-CBD (7-OH-CBD) and the hydroxylated CBD derivative of 7-carboxylic acid (7-COOH-CBD) have poor affinities for CB1 and CB2 ( Table 2) [2].…”

Section: Cb1/cb2 Receptorsmentioning

confidence: 99%

“…In contrast, cannabigivarin (a cannabigerol ropyl analogue) has been shown to stimulate and desensitize human TRPV1 (Table 2) [72]. It is also known that TRPV1 receptor activity is deeply involved in oxidative stress and inflammation [114]. Based on the understanding of the relationship between TRPV1 and oxidative stress described in Section 3.5, all of these derivatives may provide different therapeutic approaches in the case of inflammation and oxidative stress.…”

Section: Gpr55 and Trpv1 Receptorsmentioning

confidence: 99%

“…Table 2. Influence of natural and synthetic CBD derivatives on receptor activation (X: agonist activation or Y: antagonist activation by related CBD derivative; * weak affinity; #: full name is in chapter 4.1) [2,24,72,76,[114][115][116]120,[122][123][124][125][126][127]130]. Natural CB1 CB2 Gpr55 Gpr18 TRPV1 TRPA1 TRPM8 5-HT…”

Section: Trpv1 5-ht 1a and Adenosine A 2a Receptorsmentioning

confidence: 99%

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Antioxidative and Anti-Inflammatory Properties of Cannabidiol

2019

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Cannabidiol (CBD) is one of the main pharmacologically active phytocannabinoids of Cannabis sativa L. CBD is non-psychoactive but exerts a number of beneficial pharmacological effects, including anti-inflammatory and antioxidant properties. The chemistry and pharmacology of CBD, as well as various molecular targets, including cannabinoid receptors and other components of the endocannabinoid system with which it interacts, have been extensively studied. In addition, preclinical and clinical studies have contributed to our understanding of the therapeutic potential of CBD for many diseases, including diseases associated with oxidative stress. Here, we review the main biological effects of CBD, and its synthetic derivatives, focusing on the cellular, antioxidant, and anti-inflammatory properties of CBD.Antioxidants 2020, 9, 21 2 of 20 Moreover, this phytocannabinoid accelerated wound healing in a diabetic rat model by protecting the endothelial growth factor (VEGF) [11]. In addition, by preventing the formation of oxidative stress in the retina neurons of diabetic animals, CBD counteracted tyrosine nitration, which can lead to glutamate accumulation and neuronal cell death [12].This review summarizes the chemical and biological effects of CBD and its natural and synthetic derivatives. Particular attention was paid to the antioxidant and anti-inflammatory effects of CBD and its derivatives, bearing in mind the possibilities of using this phytocannabinoid to protect against oxidative stress and the consequences associated with oxidative modifications of proteins and lipids. Although CBD demonstrates safety and a good side effect profile in many clinical trials [4], all of the therapeutic options for CBD discussed in this review are limited in a concentration-dependent manner. Molecular Structure of CBDCBD is a terpenophenol compound containing twenty-one carbon atoms, with the formula C 21 H 30 O 2 and a molecular weight of 314.464 g/mol (Figure 1). The chemical structure of cannabidiol, 2-[1R-3-methyl-6R-(1-methylethenyl)-2-cyclohexen-1-yl]-5-pentyl-1, 3-benzenediol, was determined in 1963 [13]. The current IUPAC preferred terminology is 2-[(1R,6R)-3-methyl-6-prop-1-en-2-ylcyclohex-2-en-1-yl]-5-pentylbenzene-1,3-diol. Naturally occurring CBD has a (−)-CBD structure [14]. The CBD molecule contains a cyclohexene ring (A), a phenolic ring (B) and a pentyl side chain. In addition, the terpenic ring (A) and the aromatic ring (B) are located in planes that are almost perpendicular to each other [15]. There are four known CBD side chain homologs, which are methyl, n-propyl, n-butyl, and n-pentyl [16]. All known CBD forms (Table 1) have absolute trans configuration in positions 1R and 6R [16].

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Rationalizing a prospective coupling effect of cannabinoids with the current pharmacotherapy for melanoma treatment

Bachari,

Nassar,

Schanknecht

et al. 2023

WIREs Mechanisms of Disease

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Melanoma is one of the leading fatal forms of cancer, yet from a treatment perspective, we have minimal control over its reoccurrence and resistance to current pharmacotherapies. The endocannabinoid system (ECS) has recently been accepted as a multifaceted homeostatic regulator, influencing various physiological processes across different biological compartments, including the skin. This review presents an overview of the pathophysiology of melanoma, current pharmacotherapy used for treatment, and the challenges associated with the different pharmacological approaches. Furthermore, it highlights the utility of cannabinoids as an additive remedy for melanoma by restoring the balance between downregulated immunomodulatory pathways and elevated inflammatory cytokines during chronic skin conditions as one of the suggested critical approaches in treating this immunogenic tumor.This article is categorized under: Cancer > Molecular and Cellular Physiology

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Cannabidiol and Contributions of Major Hemp Phytocompounds to the “Entourage Effect”; Possible Mechanisms

Cited by 27 publications

References 0 publications

Grinding and Fractionation during Distillation Alter Hemp Essential Oil Profile and Its Antimicrobial Activity

Grinding and Fractionation during Distillation Alter Hemp Essential Oil Profile and Its Antimicrobial Activity

Antioxidative and Anti-Inflammatory Properties of Cannabidiol

Rationalizing a prospective coupling effect of cannabinoids with the current pharmacotherapy for melanoma treatment

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