Hemp Chemotype Definition by Cannabinoids Characterization Using LC-ESI(+)-LTQ-FTICR MS and Infrared Multiphoton Dissociation

Filomena Lelario,Raffaella Pascale,Giuliana Bianco,Laura Scrano,Sabino Aurelio Bufo

doi:10.3390/separations8120245

Filomena Lelario, Raffaella Pascale + Show 3 more

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https://doi.org/10.3390/separations8120245

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Journal: Separations	Publication Date: Dec 13, 2021
Citations: 6	License type: CC BY 4.0

Affiliation: University of Basilicata, University of Johannesburg

Abstract

The development and application of advanced analytical methods for a comprehensive analysis of Cannabis sativa L. extracts plays a pivotal role in order to have a reliable evaluation of their chemotype definition to guarantee the efficacy and safety in pharmaceutical use. This paper deals with the qualitative and quantitative determination of cannabidiol (CBD), tetrahydrocannabinol (THC), cannabinol (CBN), tetrahydrocannabivarin (THCV), cannabidivarin (CBDV), and cannabigerol (CBG) based on a liquid chromategraphy-mass spectrometry (LC-MS) method using electrospray ionization in positive mode (ESI+), coupled with a hybrid quadrupole linear ion trap (LTQ) and Fourier transform ion cyclotron resonance mass spectrometer (FTICR-MS). For the first time, structural information of phytocannabinoids is available upon precursor ions’ isolation within the FTICR trapping cell and subsequent fragmentation induced by infrared multiphoton dissociation (IRMPD). Such fragmentation and accurate mass measurement of product ions, alongside collision-induced dissociation (CID) within LTQ, was advantageous to propose a reliable fragmentation pattern for each compound. Then, the proposed LC-ESI(+)-LTQ-FTICR MS method was successfully applied to the hemp chemotype definition of three registered Italian accessions of hemp C. sativa plants (Carmagnola C.S., Carmagnola, and Eletta Campana), thus resulting in the Eletta Campana accession being the best one for cannabis product manufacturing.

Highlights

Cannabis contains a unique class of compounds known as phytocannabinoids
A LC-ESI-LTQ-FTICR MS method was developed for the unambiguous identification of CBD, THC, CBN, CBDV, THCV, and CBG, occurring in several registered accessions of Italian hemp plants, i.e., Carmagnola C.S., Carmagnola, and Eletta Campana, all belonging to C. sativa
The characterization of cannabinoids was performed by using the collision-induced dissociation (CID)-MSn (n = 2–5) and infrared multiphoton dissociation (IRMPD)-MS/MS

Summary

Introduction

Cannabis contains a unique class of compounds known as phytocannabinoids. They are meroterpenoid compounds whose structure has a resorcynil core typically decorated with a para-oriented isoprenyl, alkyl, or aralkyl side chain [1]. The interest in these molecules has exponentially increased thanks to discovering the human endocannabinoid system, whose receptors (CBx ) could be activated by both endogenous cannabinoids and phytocannabinoids [2,3]. ∆9 -tetrahydrocannabinol (THC), a psychoactive compound able to act as a partial agonist of human CBx ; cannabidiol (CBD), an anti-psychoactive compound, able to inhibit the effect of THC; cannabinol (CBN), the primary degradation product of THC, which bioavailability decreases [7]. In addition to THC, CBD, and CBN, pharmacological interest has been attributed to cannabigerol (CBG), the molecular precursor of THC and CBD, and ∆9 tetrahydrocannabivarin (THCV) and cannabidivarin (CBDV), their propyl analogs [8,9,10]

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