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Cis-Δ9-tetrahydrocannabinolic acid occurrence in Cannabis sativa L.
J Pharm Biomed Anal. 2022 Sep 20; 219:114958.JP

Abstract

Cannabidiolic acid (CBDA) and trans-Δ9-tetrahydrocannabinolic acid (trans-Δ9-THCA) are known to be the major phytocannabinoids in Cannabis sativa L., along with their decarboxylated derivatives cannabidiol (CBD) and trans-Δ9-tetrahydrocannabinol (trans-Δ9-THC). The cis isomer of Δ9-THC has been recently identified, characterized and quantified in several Cannabis sativa varieties, which had been heated (decarboxylated) before the analysis. Since decarboxylation alters the original phytocannabinoids composition of the plant, this work reports the identification and characterization of the carboxylated precursor cis-Δ9-THCA. The compound was also synthesized and used as analytical standard for the development and validation of a liquid chromatography coupled to high resolution mass spectrometry-based method for its quantification in ten Cannabis sativa L. samples from different chemotypes. The highest concentrations of cis-Δ9-THCA were found in CBD-rich varieties, lower levels were observed in cannabigerol (CBG)-rich varieties (chemotype IV) and in those varieties with a balanced level of both CBD and THC (chemotype III), while its levels were not detectable in cannabichromene (CBC)-rich varieties (chemotype VI). The presence of the cis isomer of THC and THCA raises the question on whether to include or not this species in the calculation of the total amount of THC to classify a cannabis variety as a drug-type or a fiber-type (hemp).

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Authors+Show Affiliations

Tolomeo F
Institute of Nanotechnology - CNR NANOTEC, Campus Ecotekne, Via Monteroni, 73100 Lecce, Italy.
Russo F
Clinical and Experimental Medicine PhD Program, University of Modena and Reggio Emilia, 41125 Modena, Italy; Department of Biomedical, Metabolic and Neural Sciences, University of Modena and Reggio Emilia, 41125 Modena, Italy.
Kaczorova D
Centre of the Region Haná for Biotechnological and Agricultural Research, Department of Genetic Resources for Vegetables, Medicinal and Special Plants, Crop Research Institute, Šlechtitelů 29, 78371 Olomouc, Czech Republic; Department of Biochemistry, Faculty of Science, Palacký University, Šlechtitelů 27, 78371 Olomouc, Czech Republic.
Vandelli MA
Department of Life Sciences, University of Modena and Reggio Emilia, Via Campi 103, 41125 Modena, Italy.
Biagini G
Department of Biomedical, Metabolic and Neural Sciences, University of Modena and Reggio Emilia, 41125 Modena, Italy.
Laganà A
Institute of Nanotechnology - CNR NANOTEC, Campus Ecotekne, Via Monteroni, 73100 Lecce, Italy; Department of Chemistry, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
Capriotti AL
Department of Chemistry, Sapienza University of Rome, Piazzale Aldo Moro 5, 00185 Rome, Italy.
Paris R
CREA - Research Center for Cereal and Industrial Crops, Via di Corticella 133, 40128 Bologna, Italy.
Fulvio F
CREA - Research Center for Cereal and Industrial Crops, Via di Corticella 133, 40128 Bologna, Italy.
Carbone L
Institute of Nanotechnology - CNR NANOTEC, Campus Ecotekne, Via Monteroni, 73100 Lecce, Italy.
Perrone E
Institute of Nanotechnology - CNR NANOTEC, Campus Ecotekne, Via Monteroni, 73100 Lecce, Italy.
Gigli G
Institute of Nanotechnology - CNR NANOTEC, Campus Ecotekne, Via Monteroni, 73100 Lecce, Italy.
Cannazza G
Institute of Nanotechnology - CNR NANOTEC, Campus Ecotekne, Via Monteroni, 73100 Lecce, Italy; Department of Life Sciences, University of Modena and Reggio Emilia, Via Campi 103, 41125 Modena, Italy. Electronic address: giuseppe.cannazza@unimore.it.
Citti C
Institute of Nanotechnology - CNR NANOTEC, Campus Ecotekne, Via Monteroni, 73100 Lecce, Italy; Department of Life Sciences, University of Modena and Reggio Emilia, Via Campi 103, 41125 Modena, Italy. Electronic address: cinzia.citti@unimore.it.

MeSH

CannabidiolCannabisChromatography, High Pressure LiquidDronabinol

Pub Type(s)

Journal Article

Language

eng

PubMed ID

35930832

Citation

Tolomeo, Francesco, et al. "Cis-Δ9-tetrahydrocannabinolic Acid Occurrence in Cannabis Sativa L." Journal of Pharmaceutical and Biomedical Analysis, vol. 219, 2022, p. 114958.
Tolomeo F, Russo F, Kaczorova D, et al. Cis-Δ9-tetrahydrocannabinolic acid occurrence in Cannabis sativa L. J Pharm Biomed Anal. 2022;219:114958.
Tolomeo, F., Russo, F., Kaczorova, D., Vandelli, M. A., Biagini, G., Laganà, A., Capriotti, A. L., Paris, R., Fulvio, F., Carbone, L., Perrone, E., Gigli, G., Cannazza, G., & Citti, C. (2022). Cis-Δ9-tetrahydrocannabinolic acid occurrence in Cannabis sativa L. Journal of Pharmaceutical and Biomedical Analysis, 219, 114958. https://doi.org/10.1016/j.jpba.2022.114958
Tolomeo F, et al. Cis-Δ9-tetrahydrocannabinolic Acid Occurrence in Cannabis Sativa L. J Pharm Biomed Anal. 2022 Sep 20;219:114958. PubMed PMID: 35930832.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Cis-Δ9-tetrahydrocannabinolic acid occurrence in Cannabis sativa L. AU - Tolomeo,Francesco, AU - Russo,Fabiana, AU - Kaczorova,Dominika, AU - Vandelli,Maria Angela, AU - Biagini,Giuseppe, AU - Laganà,Aldo, AU - Capriotti,Anna Laura, AU - Paris,Roberta, AU - Fulvio,Flavia, AU - Carbone,Luigi, AU - Perrone,Elisabetta, AU - Gigli,Giuseppe, AU - Cannazza,Giuseppe, AU - Citti,Cinzia, Y1 - 2022/07/22/ PY - 2022/05/24/received PY - 2022/07/06/revised PY - 2022/07/21/accepted PY - 2022/8/6/pubmed PY - 2022/8/17/medline PY - 2022/8/5/entrez KW - Cannabinoids KW - Cannabis sativa KW - Cis-Δ(9)-tetrahydrocannabinol KW - Cis-Δ(9)-tetrahydrocannabinolic acid KW - HPLC-HRMS SP - 114958 EP - 114958 JF - Journal of pharmaceutical and biomedical analysis JO - J Pharm Biomed Anal VL - 219 N2 - Cannabidiolic acid (CBDA) and trans-Δ9-tetrahydrocannabinolic acid (trans-Δ9-THCA) are known to be the major phytocannabinoids in Cannabis sativa L., along with their decarboxylated derivatives cannabidiol (CBD) and trans-Δ9-tetrahydrocannabinol (trans-Δ9-THC). The cis isomer of Δ9-THC has been recently identified, characterized and quantified in several Cannabis sativa varieties, which had been heated (decarboxylated) before the analysis. Since decarboxylation alters the original phytocannabinoids composition of the plant, this work reports the identification and characterization of the carboxylated precursor cis-Δ9-THCA. The compound was also synthesized and used as analytical standard for the development and validation of a liquid chromatography coupled to high resolution mass spectrometry-based method for its quantification in ten Cannabis sativa L. samples from different chemotypes. The highest concentrations of cis-Δ9-THCA were found in CBD-rich varieties, lower levels were observed in cannabigerol (CBG)-rich varieties (chemotype IV) and in those varieties with a balanced level of both CBD and THC (chemotype III), while its levels were not detectable in cannabichromene (CBC)-rich varieties (chemotype VI). The presence of the cis isomer of THC and THCA raises the question on whether to include or not this species in the calculation of the total amount of THC to classify a cannabis variety as a drug-type or a fiber-type (hemp). SN - 1873-264X UR - https://www.unboundmedicine.com/medline/citation/35930832/Cis_Δ9_tetrahydrocannabinolic_acid_occurrence_in_Cannabis_sativa_L_ DB - PRIME DP - Unbound Medicine ER -