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Non-Psychotropic Phytocannabinoids: A New Source of Drugs
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Non-Psychotropic Phytocannabinoids: A New Source of Drugs

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Bioactive Lipids".

Deadline for manuscript submissions: closed (31 May 2023) | Viewed by 15596

Special Issue Editor

Prof. Dr. Andrea Mastinu

E-Mail Website
Guest Editor
Department of Molecular and Translational Medicine, Division of Pharmacology, University of Brescia, 25123 Brescia, Italy
Interests: secondary metabolites; ethnopharmacology; abiotic stress; abiotic stress tolerance; cannabis sativa; cannabaceae; medical marijuana; phytocannabinoids; CB1 receptor; cannabidiol; tetrahydrocannabinol; CB2 receptor; cannabinoids; cannabinoid receptor agonists; cannabinoid receptor antagonists; cannabinoid receptor modulators
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

One of the most controversial and debated plants in history is Cannabis sativa. Human societies have considered C. sativa as a food, a medicine, and for religious purposes. All the virtues of C. sativa are due to the multitude of its chemical components, such as phytocannabinoids, terpenoids, flavonoids, and alkaloids, that have been extracted, purified, and tested in various preclinical models. Trans-Δ-9-tetrahydrocannabinol (D9-THC) is the phytocannabinoid responsible for the psychotropic effects of C. sativa, but in recent years, in many parts of the world, C. sativa cultivars called "light", which contain low levels of D9-THC and high levels of non-psychotropic phytocannabinoids such as cannabidiol (CBD), have been cultivated. This Special Issue will collect manuscripts on the biosynthetic, extractive, and analytical aspects of phytocannabinoids without psychotropic activity. Furthermore, particular interest will be given to the potential therapeutic applications of new characterized phytocannabinoids.

Dr. Andrea Mastinu
Guest Editor

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Keywords

  • Cannabis sativa
  • Phytocannabinoids
  • Cannabidiol
  • Cannabidivarin
  • Cannabichromene
  • Medicinal chemistry
  • Organic chemistry
  • Analitycal chemistry
  • Pharmachology
  • Endocannabinoid system

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Published Papers (4 papers)

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Research

16 pages, 2747 KiB  
Article
Chiral Separation of Cannabichromene, Cannabicyclol, and Their Acidic Analogs on Polysaccharide Chiral Stationary Phases
by John M. Ferraro and Weston J. Umstead
Molecules 2023, 28(3), 1164; https://doi.org/10.3390/molecules28031164 - 24 Jan 2023
Cited by 9 | Viewed by 2875
Abstract
Until recently, chirality has not been a major focus in the study of cannabinoids, as most cannabinoids of interest, such as cannabidiol and tetrahydrocannabinol, exist as a single isomer from natural sources. However, this is changing as more cannabinoids are identified, and compounds [...] Read more.
Until recently, chirality has not been a major focus in the study of cannabinoids, as most cannabinoids of interest, such as cannabidiol and tetrahydrocannabinol, exist as a single isomer from natural sources. However, this is changing as more cannabinoids are identified, and compounds such as cannabichromene and cannabicyclol are emerging as potential investigatory candidates for varying indications. Because these molecules are chiral, the separation and study of the individual enantiomers’ biological and physiological effects should therefore be of interest. The purpose of this study was to identify analytical separation conditions and then adapt those conditions to preparative separation. This was accomplished with a column-screening approach on Daicel’s immobilized polysaccharide chiral stationary phases using non-traditional mobile phases, which included dichloromethane, ethyl acetate, and methyl tert-butyl ether under high-performance liquid chromatography conditions. CHIRALPAK® IK was found to separate all four compounds well with mobile phases containing hexane-dichloromethane (with or without an acidic additive). From these methods, the separation productivities were calculated to better visualize the separation scalability, which shows that the kilogram-scale separations of each are feasible. Full article
(This article belongs to the Special Issue Non-Psychotropic Phytocannabinoids: A New Source of Drugs)
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16 pages, 4097 KiB  
Article
Identification of SARS-CoV-2 Main Protease Inhibitors from a Library of Minor Cannabinoids by Biochemical Inhibition Assay and Surface Plasmon Resonance Characterized Binding Affinity
by Chang Liu, Tess Puopolo, Huifang Li, Ang Cai, Navindra P. Seeram and Hang Ma
Molecules 2022, 27(18), 6127; https://doi.org/10.3390/molecules27186127 - 19 Sep 2022
Cited by 8 | Viewed by 4136
Abstract
The replication of the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is mediated by its main protease (Mpro), which is a plausible therapeutic target for coronavirus disease 2019 (COVID-19). Although numerous in silico studies reported the potential inhibitory effects of natural [...] Read more.
The replication of the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is mediated by its main protease (Mpro), which is a plausible therapeutic target for coronavirus disease 2019 (COVID-19). Although numerous in silico studies reported the potential inhibitory effects of natural products including cannabis and cannabinoids on SARS-CoV-2 Mpro, their anti-Mpro activities are not well validated by biological experimental data. Herein, a library of minor cannabinoids belonging to several chemotypes including tetrahydrocannabinols, cannabidiols, cannabigerols, cannabichromenes, cannabinodiols, cannabicyclols, cannabinols, and cannabitriols was evaluated for their anti-Mpro activity using a biochemical assay. Additionally, the binding affinities and molecular interactions between the active cannabinoids and the Mpro protein were studied by a biophysical technique (surface plasmon resonance; SPR) and molecular docking, respectively. Cannabinoids tetrahydrocannabutol and cannabigerolic acid were the most active Mpro inhibitors (IC50 = 3.62 and 14.40 μM, respectively) and cannabigerolic acid had a binding affinity KD=2.16×10−4 M). A preliminary structure and activity relationship study revealed that the anti-Mpro effects of cannabinoids were influenced by the decarboxylation of cannabinoids and the length of cannabinoids’ alkyl side chain. Findings from the biochemical, biophysical, and computational assays support the growing evidence of cannabinoids’ inhibitory effects on SARS-CoV-2 Mpro. Full article
(This article belongs to the Special Issue Non-Psychotropic Phytocannabinoids: A New Source of Drugs)
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15 pages, 2927 KiB  
Article
A Critical Evaluation of Terpenoid Signaling at Cannabinoid CB1 Receptors in a Neuronal Model
by Michaela Dvorakova, Sierra Wilson, Wesley Corey, Jenna Billingsley, Anaëlle Zimmowitch, Joye Tracey, Alex Straiker and Ken Mackie
Molecules 2022, 27(17), 5655; https://doi.org/10.3390/molecules27175655 - 2 Sep 2022
Cited by 2 | Viewed by 3204
Abstract
In addition to phytocannabinoids, cannabis contains terpenoids that are claimed to have a myriad of effects on the body. We tested a panel of five common cannabis terpenoids, myrcene, linalool, limonene, α-pinene and nerolidol, in two neuronal models, autaptic hippocampal neurons and dorsal [...] Read more.
In addition to phytocannabinoids, cannabis contains terpenoids that are claimed to have a myriad of effects on the body. We tested a panel of five common cannabis terpenoids, myrcene, linalool, limonene, α-pinene and nerolidol, in two neuronal models, autaptic hippocampal neurons and dorsal root ganglion (DRG) neurons. Autaptic neurons express a form of cannabinoid CB1 receptor-dependent retrograde plasticity while DRGs express a variety of transient receptor potential (TRP) channels. Most terpenoids had little or no effect on neuronal cannabinoid signaling. The exception was nerolidol, which inhibited endocannabinoid signaling. Notably, this is not via inhibition of CB1 receptors but by inhibiting some aspect of 2-arachidonoylglycerol (2-AG) production/delivery; the mechanism does not involve reducing the activity of the 2-AG-synthesizing diacylglycerol lipases (DAGLs). Nerolidol was also the only terpenoid that activated a sustained calcium response in a small (7%) subpopulation of DRGs. In summary, we found that only one of five terpenoids tested had notable effects on cannabinoid signaling in two neuronal models. Our results suggest that a few terpenoids may indeed interact with some components of the cannabinoid signaling system and may therefore offer interesting insights upon further study. Full article
(This article belongs to the Special Issue Non-Psychotropic Phytocannabinoids: A New Source of Drugs)
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11 pages, 2218 KiB  
Article
Conversion Characteristics of Some Major Cannabinoids from Hemp (Cannabis sativa L.) Raw Materials by New Rapid Simultaneous Analysis Method
by Byeong Ryeol Ryu, Md. Jahirul Islam, Md. Obyedul Kalam Azad, Eun-Ji Go, Md. Hafizur Rahman, Md. Soyel Rana, Young-Seok Lim and Jung-Dae Lim
Molecules 2021, 26(14), 4113; https://doi.org/10.3390/molecules26144113 - 6 Jul 2021
Cited by 18 | Viewed by 4263
Abstract
This study was carried out to develop a high-performance liquid chromatography method for short-time analysis of the main cannabinoids in the inflorescence of hemp (Cannabis sativa L.). We also performed decarboxylation of the raw material using our advanced analysis technique. In this [...] Read more.
This study was carried out to develop a high-performance liquid chromatography method for short-time analysis of the main cannabinoids in the inflorescence of hemp (Cannabis sativa L.). We also performed decarboxylation of the raw material using our advanced analysis technique. In this study, the UV spectrum was considered to analyze each of the four common cannabinoids, solvents, and samples, where the uniform elution of acidic cannabinoids without peak tailing and acids was tested. Optimal results were obtained when readings were taken at a wavelength of 220 nm using water and methanol containing trifluoroacetic acid as mobile phases in a solvent gradient system. The established conditions were further validated by system suitability, linearity, precision, detection limit, and quantitation limit tests. The decarboxylation index (DT50) confirmed that Δ9-THCA decarboxylated faster than CBDA, and both maintained a linear relationship with time and temperature. In addition, the loss of cannabidiol was better prevented during the decarboxylation process in the natural state than in the extracted state. Full article
(This article belongs to the Special Issue Non-Psychotropic Phytocannabinoids: A New Source of Drugs)
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