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Special Issue "Non-Psychotropic Phytocannabinoids: A New Source of Drugs"

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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 9374

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Prof. Dr. Andrea Mastinu

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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
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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

Manuscript Submission Information

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Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

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

Published Papers (4 papers)

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Research

Open AccessArticle

Chiral Separation of Cannabichromene, Cannabicyclol, and Their Acidic Analogs on Polysaccharide Chiral Stationary Phases

John M. Ferraro

and

Weston J. Umstead

Molecules 2023, 28(3), 1164; https://doi.org/10.3390/molecules28031164 - 24 Jan 2023

Cited by 2 | Viewed by 1334

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 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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Open AccessArticle

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

and

Molecules 2022, 27(18), 6127; https://doi.org/10.3390/molecules27186127 - 19 Sep 2022

Cited by 3 | Viewed by 2497

Abstract

The replication of the severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) is mediated by its main protease (M^pro), 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 M^pro, their anti-M^pro 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-M^pro activity using a biochemical assay. Additionally, the binding affinities and molecular interactions between the active cannabinoids and the M^pro protein were studied by a biophysical technique (surface plasmon resonance; SPR) and molecular docking, respectively. Cannabinoids tetrahydrocannabutol and cannabigerolic acid were the most active M^pro inhibitors (IC₅₀ = 3.62 and 14.40 μM, respectively) and cannabigerolic acid had a binding affinity

K_{D} = 2.16 \times 10^{- 4}

M). A preliminary structure and activity relationship study revealed that the anti-

M^{pro}

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 M^pro. Full article

(This article belongs to the Special Issue Non-Psychotropic Phytocannabinoids: A New Source of Drugs)

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Open AccessArticle

A Critical Evaluation of Terpenoid Signaling at Cannabinoid CB1 Receptors in a Neuronal Model

and

Molecules 2022, 27(17), 5655; https://doi.org/10.3390/molecules27175655 - 02 Sep 2022

Cited by 1 | Viewed by 2064

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 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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Open AccessArticle

Conversion Characteristics of Some Major Cannabinoids from Hemp (Cannabis sativa L.) Raw Materials by New Rapid Simultaneous Analysis Method

Byeong Ryeol Ryu

Md. Jahirul Islam

Md. Obyedul Kalam Azad

and

Molecules 2021, 26(14), 4113; https://doi.org/10.3390/molecules26144113 - 06 Jul 2021

Cited by 10 | Viewed by 2622

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 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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Special Issue "Non-Psychotropic Phytocannabinoids: A New Source of Drugs"

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