HPLC-UV-HRMS analysis of cannabigerovarin and cannabigerobutol, the two impurities of cannabigerol extracted from hemp

Tolomeo, Francesco; Russo, Fabiana; Vandelli, Maria Angela; Biagini, Giuseppe; Capriotti, Anna Laura; Laganà, Aldo; Carbone, Luigi; Gigli, Giuseppe; Cannazza, Giuseppe; Citti, Cinzia

doi:10.1016/j.jpba.2021.114215

Cited by 9 publications

(12 citation statements)

References 18 publications

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“…The column was re-equilibrated at 70% ACN for further 3 min for a total run time of 26 min at a constant ow rate of 0.5 mL/min. The HESI parameters were optimized in previous works for cannabinoids: spray voltage 4200 kV and 3800 kV for HESI + and HESI-mode respectively, sheath gas 70 au, auxiliary gas 5 au, sweep gas 0.5 au, ion transfer tube temperature 390°C and vaporizer temperature 150°C 23,25 . The mass analyzer was operated in both full scan (FS) and data-dependent acquisition (DDA) mode.…”

Section: Methodsmentioning

confidence: 99%

“…In FS mode the resolution was set at 60,000 FWHM (full width at half maximum), the RF lens level at 70%, the maximum injection time 54 ms, the m/z range at 150-750, and the isolation window at m/z 1.2. In DDA mode the resolution was set at 30,000 FWHM, the maximum injection time at 22 ms, the m/z range at 50-750, the isolation window at m/z 1.2, and the stepped normalized collision energy (NCE) at 20-40-100 23,25 . The injection volume was 5 µL.…”

Section: Methodsmentioning

confidence: 99%

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The semisynthetic cannabinoid Hexahydrocannabinol (HHC)

Russo

Vandelli

Biagini

et al. 2023

Preprint

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Cannabis is a double-faced plant with uncountable therapeutic properties, on one side, and controversial psychotropic activities, on the other side, modulated by CB1 endocannabinoid receptors. Δ9-Tetrahydrocannabinol (Δ9-THC) has been identified as the main component responsible for the psychotropic effects, while its isomer cannabidiol (CBD) has shown completely different pharmacological properties. Based on the remarkable beneficial effects, Cannabis has spread worldwide and it is openly sold in shops and online. In order to overcome restrictions due to legal issues, nowadays semi-synthetic derivatives of CBD are often added to cannabis products, obtaining “high” effects similar to those given by Δ9-THC. The first semi-synthetic cannabinoid appeared in the EU was obtained by cyclization and hydrogenation of CBD, and known as hexahydrocannabinol (HHC). At present, very little is known about HHC, its pharmacological properties, and diffusion, since it is not commonly investigated in routine toxicological assays. In the present work, the synthetic strategies aimed to obtain an excess of the active epimer of HHC were investigated and the two epimers were purified and individually tested for their cannabinomimetic activity. Lastly, a simple and fast chromatographic method with a UV detector and a high-resolution mass spectrometer was applied to identify and quantify up to ten major phytocannabinoids, as well as the HHC epimers in commercial cannabis samples.

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Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

The semisynthetic cannabinoid Hexahydrocannabinol (HHC)

Russo

Vandelli

Biagini

et al. 2023

Preprint

Self Cite

View full text Add to dashboard Cite

show abstract

“…Most commonly used MS analyzers include simple Q spectrometers [ 181 ], QQQ analyzers [ 11 , 58 , 68 , 97 , 114 , 147 , 193 , 194 ], IT analyzers [ 28 , 43 , 72 , 185 ], QTRAP [ 67 , 159 , 191 , 195 ] or high resolution-accurate mass MS (HRAM-MS) analysers, such as Q-TOF [ 83 , 88 , 139 , 189 ] and Q-Exactive TM Orbitrap [ 19 , 63 , 65 , 66 ].…”

Section: Analytical Methods For Phytocannabinoid Profilingmentioning

confidence: 99%

“…Phytocannabinoid profiling is most commonly performed using ESI, rarely using variations such as dual source [ 78 ] or heated ESI source [ 19 , 63 ]. Acquisitions are performed in positive (+) [ 88 , 147 , 189 , 191 , 193 , 194 ], negative (−) [ 134 ] or both (+) and (−) modes [ 27 , 40 , 55 , 62 , 63 , 64 , 92 , 144 , 178 , 181 ]. In fact, all major phytocannabinoids are detected in both ionization modes, except for THCV [ 78 ].…”

Section: Analytical Methods For Phytocannabinoid Profilingmentioning

confidence: 99%

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Analytical Techniques for Phytocannabinoid Profiling of Cannabis and Cannabis-Based Products—A Comprehensive Review

et al. 2022

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Cannabis is gaining increasing attention due to the high pharmacological potential and updated legislation authorizing multiple uses. The development of time- and cost-efficient analytical methods is of crucial importance for phytocannabinoid profiling. This review aims to capture the versatility of analytical methods for phytocannabinoid profiling of cannabis and cannabis-based products in the past four decades (1980–2021). The thorough overview of more than 220 scientific papers reporting different analytical techniques for phytocannabinoid profiling points out their respective advantages and drawbacks in terms of their complexity, duration, selectivity, sensitivity and robustness for their specific application, along with the most widely used sample preparation strategies. In particular, chromatographic and spectroscopic methods, are presented and discussed. Acquired knowledge of phytocannabinoid profile became extremely relevant and further enhanced chemotaxonomic classification, cultivation set-ups examination, association of medical and adverse health effects with potency and/or interplay of certain phytocannabinoids and other active constituents, quality control (QC), and stability studies, as well as development and harmonization of global quality standards. Further improvement in phytocannabinoid profiling should be focused on untargeted analysis using orthogonal analytical methods, which, joined with cheminformatics approaches for compound identification and MSLs, would lead to the identification of a multitude of new phytocannabinoids.

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Progress in the analysis of phytocannabinoids by HPLC and UPLC (or UHPLC) during 2020–2023

Nahar,

Chaiwut,

Sangthong

et al. 2024

Phytochemical Analysis

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IntroductionOrganic molecules that bind to cannabinoid receptors are known as cannabinoids. These molecules possess pharmacological properties similar to those produced by Cannabis sativa L. High‐performance liquid chromatography (HPLC) and ultra‐performance liquid chromatography (UPLC, also known as ultra‐high‐performance liquid chromatography, UHPLC) have become the most widely used analytical tools for detection and quantification of phytocannabinoids in various matrices. HPLC and UPLC (or UHPLC) are usually coupled to an ultraviolet (UV), photodiode array (PDA), or mass spectrometric (MS) detector.ObjectiveTo critically appraise the literature on the application of HPLC and UPLC (or UHPLC) methods for the analysis of phytocannabinoids published from January 2020 to December 2023.MethodologyAn extensive literature search was conducted using Web of Science, PubMed, and Google Scholar and published materials including relevant books. In various combinations, using cannabinoid in all combinations, cannabis, hemp, hashish, C. sativa, marijuana, analysis, HPLC, UHPLC, UPLC, and quantitative, qualitative, and quality control were used as the keywords for the literature search.ResultsSeveral HPLC‐ and UPLC (or UHPLC)‐based methods for the analysis of phytocannabinoids were reported. While simple HPLC‐UV or HPLC‐PDA‐based methods were common, the use of HPLC‐MS, HPLC‐MS/MS, UPLC (or UHPLC)‐PDA, UPLC (or UHPLC)‐MS, and UPLC (or UHPLC)‐MS/MS was also reported. Applications of mathematical and computational models for optimization of protocols were noted. Pre‐analyses included various environmentally friendly extraction protocols.ConclusionDuring the last 4 years, HPLC and UPLC (or UHPLC) remained the main analytical tools for phytocannabinoid analysis in different matrices.

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HPLC-UV-HRMS analysis of cannabigerovarin and cannabigerobutol, the two impurities of cannabigerol extracted from hemp

Cited by 9 publications

References 18 publications

The semisynthetic cannabinoid Hexahydrocannabinol (HHC)

The semisynthetic cannabinoid Hexahydrocannabinol (HHC)

Analytical Techniques for Phytocannabinoid Profiling of Cannabis and Cannabis-Based Products—A Comprehensive Review

Progress in the analysis of phytocannabinoids by HPLC and UPLC (or UHPLC) during 2020–2023

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