Publicado

2019-09-01

Determinación y comparación cualitativa de cannabinoides presentes en productos naturales comerciales del departamento del Cauca-Colombia

Determination and qualitative comparison of cannabinoids present in commercial natural products of the Cauca Department-Colombia

DOI:

https://doi.org/10.15446/rcciquifa.v48n3.84992

Palavras-chave:

Cromatografía líquida de alta resolución (CLAR), espectrometría de masas (EM), delta 9 tetrahidrocannabinol (Δ9 THC), cannabinol (CBN), cannabigerol (CBG), cannabidiol (CBD) (es)
High performance liquid chromatography (HPLC), mass spectrometry (MS), delta 9 tetrahydrocannabinol (Δ9 THC), cannabinol (CBN), cannabigerol (CBG), cannabidiol (CBD) (en)

Autores

  • Johnnatan Mauricio Giraldo Grupo de Investigación de Química de Productos Naturales (QPN), Departamento de Química, Universidad del Cauca Carrera 2# 3N-45, Popayán-Cauca
  • Ricardo Benítez Benítez Grupo de Investigación de Química de Productos Naturales (QPN), Departamento de Química, Universidad del Cauca Carrera 2# 3N-45, Popayán-Cauca
  • Rodrigo Andrés Sarria-Villa Grupo de Investigación de Química de Productos Naturales (QPN), Departamento de Química, Universidad del Cauca Carrera 2# 3N-45, Popayán-Cauca
  • Paola Andrea Arango Grupo de Investigación de Química de Productos Naturales (QPN), Departamento de Química, Universidad del Cauca Carrera 2# 3N-45, Popayán-Cauca
  • Jaime Martin Franco Grupo de Investigación de Química de Productos Naturales (QPN), Departamento de Química, Universidad del Cauca Carrera 2# 3N-45, Popayán-Cauca

Actualmente, hay un creciente interés por el estudio de Cannabis sativa y sus componentes ya que se le atribuye propiedades terapéuticas en el tratamiento de enfermedades. En Colombia y específicamente en el departamento del Cauca se comercializan productos de cannabis tanto para fines no medicinales como terapéuticos. En consecuencia, es necesario el análisis de estos productos de manera que se pueda conocer la composición de los mismos y el posible efecto que pueda tener sobre la salud.

El análisis de los componentes de estos productos se llevó a cabo empleando la cromatografía líquida de alta resolución (CLAR) y espectrometría de masas (EM), de tal manera que permitieron la identificación de las principales especies cannabinoides; Δ9tetrahidrocannabinol (THC), cannabidiol (CBD), cannabinol (CBN), cannabigerol (CBG). La separación de los analitos se llevó a cabo mediante la implementación de una columna analítica C18 de fase reversa, elución isocrática 1 mL/min, presión del sistema 800 PSI, una mezcla de acetonitrilo ACN y buffer fosfato (KHPO4) en relación 65/35 como fase móvil, volumen de inyección de 10 µL, un tiempo de análisis de 15 min, y detección a 220 nm.

Cannabis sativa has now experienced an increasing interest in the study of its components since it is attributed therapeutic properties in the treatment of diseases. In Colombia and specifically in the Cauca Department, Cannabis products are marketed both for non-medicinal and therapeutic purposes. Consequently, it is necessary to analyze these products in such a way that the composition of the products and their possible effect on health can be known. The analysis of the components of these products was carried out using high performance liquid chromatography (HPLC) and mass spectrometry (MS), in such a way that they allowed the identification of the main cannabinoid species; Δ 9tetrahydrocannabinol (THC), cannabidiol (CBD), cannabinol (CBN), cannabigerol (CBG). The separation of the analytes was carried out by means of the implementation of a reverse phase C18 analytical column, isocratic elution 1 mL/min, system pressure 800 PSI, a mixture of acetonitrile ACN and phosphate buffer (KHPO4) in relation 65/35 as mobile phase, injection volume of 10 μL, analysis time of 15 min, and detection at 220 nm.

Referências

J.K. Booth, J. Bohlmann, Terpenes in Cannabis sativa - From plant genome to humans, Plant Sci., 284, 67-72 (2019).

Y. Zhou, S. Wang, H. Lou, P. Fan, Chemical constituents of hemp (Cannabis sativa L.) seed with potential anti-neuroinflammatory activity, Phytochem. Lett., 23, 57-61 (2018).

F. Cascini, I. Boschi, Tetrahydrocannabinol concentration and genetic characterization of Cannabis, en: Handbook of Cannabis and Related Pathologies Biology, Pharmacology, Diagnosis, and Treatment, Academic Press, Elsevier Inc., 2017.

M.A. ElSohly, D. Slade, Chemical constituents of marijuana: The complex mixture of natural cannabinoids, Life Sci., 78(5), 539-548 (2005).

J.A. Hartsel, J. Eades, B. Hickory, Cannabis sativa and Hemp. En: Nutraceuticals: Efficacy, Safety and Toxicity, Chapter 53, Elsevier Inc., 2016.

R.A. Sansone, L.A. Sansone, Marijuana and body weight, Innov. Clin. Neurosci., 11(7-8), 50-54 (2014).

S. Pinar-Sueiro, R. Rodríguez-Puertas, E. Vecino, Cannabinoid applications in glaucoma, Arch. Soc. Esp. Oftalmol., 86(1), 16-23 (2011).

T. Dale, J. Downs, H. Olson, A. M. Bergin, S. Smith, H. Leonard, Cannabis for refractory epilepsy in children: A review focusing on CDKL5 deficiency disorder, Epilepsy Res., 151, 31-39 (2019).

F. Grotenhermen, K. Müller-Vahl, Das therapeutische Potenzial von Cannabis und Cannabinoiden, Dtsch. Arztebl. Int., 109(29-30), 495-501 (2012).

R. Abuhasira, L. Shbiro, Y. Landschaft, Medical use of cannabis and cannabinoids containing products. Regulations in Europe and North America, Eur. J. Intern. Med., 49, 2-6 (2018).

C. Nucci, M. Bari, A. Spanò, M. Corasaniti, G. Bagetta, M. Maccarrone, L.A. Morrone, Potential roles of (endo)cannabinoids in the treatment of glaucoma: from intraocular pressure control to neuroprotection, Prog. Brain Res., 173(8), 451-464 (2008).

M.A.P. Bloomfield, C. Hindocha, S.F. Green, M.B. Wall, R. Lees, K. Petrilli, H. Costello, M.O. Ogunbiyi, M.G. Bossong, T.P. Freeman, The neuropsychopharmacology of cannabis: A review of human imaging studies, Pharmacol. Ther., 195, 132-161 (2019).

T. Byars, E. Theisen, D.L. Bolton, Using Cannabis to treat cancer-related pain, Semin. Oncol. Nurs., 35(3), 300-309 (2019).

V. Gambaro, L. Dell’Acqua, F. Farè, R. Froldi, E. Saligari, G. Tassoni, Determination of primary active constituents in Cannabis preparations by high-resolution gas chromatography/flame ionization detection and high-performance liquid chromatography/UV detection, Anal. Chim. Acta, 468(2), 245-254 (2002).

F. Palazzoli, C. Citti, M. Licata, A. Vilella, L. Manca, M. Zoli, M.A. Vandelli, F. Forni, G. Cannazza, Development of a simple and sensitive liquid chromatography triple quadrupole mass spectrometry (LC-MS/MS) method for the determination of cannabidiol (CBD), Δ9-tetrahydrocannabinol (THC) and its metabolites in rat whole blood after oral administration of CBD, J. Pharm. Biomed. Anal., 150, 25-32 (2018).

S.B. Grauwiler, A. Scholer, J. Drewe, Development of a LC/MS/MS method for the analysis of cannabinoids in human EDTA-plasma and urine after small doses of Cannabis sativa extracts, J. Chromatogr. B, Anal. Technol. Biomed. Life Sci., 850(1-2), 515-522 (2007).

S. Pichini, E. Marchei, S. Martello, M. Gottardi, M. Pellegrini, F. Svaizer, A. Lotti, M. Chiarotti, R. Pacifici, Identification and quantification of 11-nor-δ9-tetrahydrocannabinol-9-carboxylic acid glucuronide (THC-COOH-glu) in hair by ultra-performance liquid chromatography tandem mass spectrometry as a potential hair biomarker of cannabis use, Forensic Sci. Int., 249, 47-51 (2015).

A. Hazekamp, A. Peltenburg, R. Verpoorte, C. Giroud, chromatographic and spectroscopic data of cannabinoids from Cannabis sativa L., J. Liq. Chromatogr. Related Technol., 28(15), 2361-2382 (2005).

B. Patel, D. Wene, Z.T. Fan, Qualitative and quantitative measurement of cannabinoids in cannabis using modified HPLC/DAD method, J. Pharm. Biomed. Anal., 146, 15-23 (2017).

B. Tassi-Borille, M. González, L. Steffens, R. Scorsatto-Ortiz, R Pereira-Limberger, Cannabis sativa: A systematic review of plant analysis, Drug Anal. Res., 1(1), 1-23 (2017).

R.E. Deimler, T.T. Razunguzwa, B.R. Reschke, C.M. Walsh, M.J. Powell, G.P. Jackson, Direct analysis of drugs in forensic applications using laser ablation electrospray ionization-tandem mass spectrometry (LAESI-MS/MS), Anal. Methods, 6(13), 4810-4817 (2014).

D. Wianowska, A.L. Dawidowicz, M. Kowalczyk, Transformations of tetrahydrocannabinol, tetrahydrocannabinolic acid and cannabinol during their extraction from Cannabis sativa L., J. Anal. Chem., 70(8), 920-925 (2015).

F. Erdmann, G. Rochholz, H. Schütz, Retention-indices on OV-1 of approximately 170 commonly used pesticides, Mikrochim. Acta, 106(3-6), 219-226 (1992).

K.O. Oliveira, A.R.M. Silva, B.F. da Silva, H.M.S. Milagre, C.D.F. Milagre, Insights into the microbial degradation pathways of the ioxynil octanoate herbicide, Biocatal. Agric. Biotechnol., 13, 258-264 (2018).

F.J.E.M. Kuppers, C.A.L. Bercht, C.A. Salemink, J.K. Terlouw, W. Heerma, Pirolysis of cannabidiol. Structure elucidation of four pyrolytic products, Laboratory of Organic Chemistry, State University of Utrecht, The Netherlands, vol. 458, 1975, pp. 3669-3684.

F. Palazzoli, C. Citti, M. Licata, S. Vilella, L. Manca, M. Zoli, M.A. Vandelli, F. Forni, G. Cannazza, Development of a simple and sensitive liquid chromatography triple quadrupole mass spectrometry (LC-MS/MS) method for the determination of cannabidiol (CBD), 9-tetrahydrocannabinol (THC) and its metabolites in rat whole blood after oral administration of a single high dose of CBD, J. Pharm. Biomed. Anal., 150, 25-32 (2018).

T.B. Vree, Mass spectrometry of cannabinoids, J. Pharm. Sci., 66(10), 1444-1450 (1977).

Z. Bruci, I. Papoutsis, S. Athanaselis, P. Nikolaou, E. Pazari, C. Spiliopoulou, G. Vyshka, First systematic evaluation of the potency of Cannabis sativa plants grown in Albania, Forensic Sci. Int., 222(1-3), 40-46 (2012).

R. Jamwal, A.R. Topletz, B. Ramratnam, F. Akhlaghi, Ultra-high performance liquid chromatography tandem mass-spectrometry for simple and simultaneous quantification of cannabinoids, J. Chromatogr. B, Anal. Technol. Biomed. Life Sci., 1048, 10-18 (2017).

K. Mechtler, J. Bailer, K. De Hueber, Variations of Δ9-THC content in single plants of hemp varieties, Ind. Crops Prod., 19(1), 19-24 (2004).

D.M. Andrenyak, D.E. Moody, M.H. Slawson, D.S. O’Leary, M. Haney, Determination of Δ9-Tetrahydrocannabinol (THC), 11-hydroxy-11-nor-9-carboxy-THC and Cannabidiol in human plasma using gas chromatography-tandem mass spectrometry, J. Toxicol. Anal., 41, 277-288 (2017).

L.V. Tose, N.A. Santos, R.R.T. Rodrigues, M. Murgu, A.F. Gomes, G.A. Vasconcelos, P.C.T. Souza, B.G. Vaz, W. Romão, Isomeric Separation of Cannabinoids by UPLC combined with ionic mobility mass spectrometry (TWIM-MS). Part I, Int. J. Mass Spectrom., 418, 112-121 (2017).

T.B. Vree, D.D. Breimer, C.A.M. Van Ginneken, J.M. Van Rossum, R.A. De Zeeuw, A.H. Witte, Identification of cannabivarins in hashish by a new method of combined gas chromatography-mass-spectrometry, Clin. Chim. Acta, 34(2), 365-372 (1971).

C. Coulter, M. Garnier, C. Moore, Analysis of tetrahydrocannabinol and its metabolite, 11-nor-Δ9-tetrahydrocannabinol-9-carboxylic acid, in oral fluid using liquid chromatography with tandem mass spectrometry, J. Anal. Toxicol., 36(6), 413-417 (2012).

M.S. Aymerich, E. Aso, M.A. Abellanas, R.M. Tolon, J.A. Ramos, I. Ferrer, J. Romero, J. Fernández-Ruiz, Cannabinoid pharmacology/therapeutics in chronic degenerative disorders affecting the central nervous system, Biochem. Pharmacol., 157, 67-84 (2018).

M. Ben Amar, Cannabinoids in medicine: A review of their therapeutic potential, J. Ethnopharmacol., 105(1-2), 1-25 (2006).

M. Ganzera, S. Sturm, Recent advances on HPLC/MS in medicinal plant analysis. An update covering 2011–2016, J. Pharm. Biomed. Anal., 147, 211-233 (2018).

G. Velasco, S. Hernández-Tiedra, D. Dávila, M. Lorente, The use of cannabinoids as anticancer agents, Prog. Neuro-Psychopharmacology Biol. Psychiatry, 64, 259-266 (2016).

D. Baker, G. Pryce, G. Giovannoni, A.J. Thompson, The therapeutic potential of cannabis, Lancet Neurol., 2(5), 291-298 (2003).

M. Felli, S. Martello, M. Chiarotti, LC-MS-MS method for simultaneous determination of THCCOOH and THCCOOH-glucuronide in urine: Application to workplace confirmation tests, Forensic Sci. Int., 204(1-3), 67-73 (2011).

N. Maurya, B.K. Velmurugan, Therapeutic applications of cannabinoids, Chem. Biologycal. Interactions., 293, 77-88 (2018).

V. Chiurchiù, M. Van Der Stelt, D. Centonze, M. Maccarrone, The endocannabinoid system and its therapeutic exploitation in multiple sclerosis: Clues for other neuroinflammatory diseases, Prog. Neurobiol., 160, 82-100 (2018).

S.P.H. Alexander, Therapeutic potential of cannabis-related drugs, Prog. Neuro-Psychopharmacology Biol. Psychiatry, 64, 157-166 (2016).

D.M. Li, C.K. Ng, Effects of delta 1- and delta 6-tetrahydrocannabinol on the adenylate cyclase activity in ventricular tissue of the rat heart, Clin. Exp. Pharmacol. Physiol., 11(1), 81-85 (1984).

F. Grotenhermen, E. Russo, Cannabis and cannabinoids: pharmacology, toxicology, and therapeutic potential, Haworth Integrative Healing Press, 2002.

Como Citar

APA

Giraldo, J. M., Benítez Benítez, R., Sarria-Villa, R. A., Arango, P. A. e Franco, J. M. (2019). Determinación y comparación cualitativa de cannabinoides presentes en productos naturales comerciales del departamento del Cauca-Colombia. Revista Colombiana de Ciencias Químico-Farmacéuticas, 48(3). https://doi.org/10.15446/rcciquifa.v48n3.84992

ACM

[1]
Giraldo, J.M., Benítez Benítez, R., Sarria-Villa, R.A., Arango, P.A. e Franco, J.M. 2019. Determinación y comparación cualitativa de cannabinoides presentes en productos naturales comerciales del departamento del Cauca-Colombia. Revista Colombiana de Ciencias Químico-Farmacéuticas. 48, 3 (set. 2019). DOI:https://doi.org/10.15446/rcciquifa.v48n3.84992.

ACS

(1)
Giraldo, J. M.; Benítez Benítez, R.; Sarria-Villa, R. A.; Arango, P. A.; Franco, J. M. Determinación y comparación cualitativa de cannabinoides presentes en productos naturales comerciales del departamento del Cauca-Colombia. Rev. Colomb. Cienc. Quím. Farm. 2019, 48.

ABNT

GIRALDO, J. M.; BENÍTEZ BENÍTEZ, R.; SARRIA-VILLA, R. A.; ARANGO, P. A.; FRANCO, J. M. Determinación y comparación cualitativa de cannabinoides presentes en productos naturales comerciales del departamento del Cauca-Colombia. Revista Colombiana de Ciencias Químico-Farmacéuticas, [S. l.], v. 48, n. 3, 2019. DOI: 10.15446/rcciquifa.v48n3.84992. Disponível em: https://revistas.unal.edu.co/index.php/rccquifa/article/view/84992. Acesso em: 22 jan. 2025.

Chicago

Giraldo, Johnnatan Mauricio, Ricardo Benítez Benítez, Rodrigo Andrés Sarria-Villa, Paola Andrea Arango, e Jaime Martin Franco. 2019. “Determinación y comparación cualitativa de cannabinoides presentes en productos naturales comerciales del departamento del Cauca-Colombia”. Revista Colombiana De Ciencias Químico-Farmacéuticas 48 (3). https://doi.org/10.15446/rcciquifa.v48n3.84992.

Harvard

Giraldo, J. M., Benítez Benítez, R., Sarria-Villa, R. A., Arango, P. A. e Franco, J. M. (2019) “Determinación y comparación cualitativa de cannabinoides presentes en productos naturales comerciales del departamento del Cauca-Colombia”, Revista Colombiana de Ciencias Químico-Farmacéuticas, 48(3). doi: 10.15446/rcciquifa.v48n3.84992.

IEEE

[1]
J. M. Giraldo, R. Benítez Benítez, R. A. Sarria-Villa, P. A. Arango, e J. M. Franco, “Determinación y comparación cualitativa de cannabinoides presentes en productos naturales comerciales del departamento del Cauca-Colombia”, Rev. Colomb. Cienc. Quím. Farm., vol. 48, nº 3, set. 2019.

MLA

Giraldo, J. M., R. Benítez Benítez, R. A. Sarria-Villa, P. A. Arango, e J. M. Franco. “Determinación y comparación cualitativa de cannabinoides presentes en productos naturales comerciales del departamento del Cauca-Colombia”. Revista Colombiana de Ciencias Químico-Farmacéuticas, vol. 48, nº 3, setembro de 2019, doi:10.15446/rcciquifa.v48n3.84992.

Turabian

Giraldo, Johnnatan Mauricio, Ricardo Benítez Benítez, Rodrigo Andrés Sarria-Villa, Paola Andrea Arango, e Jaime Martin Franco. “Determinación y comparación cualitativa de cannabinoides presentes en productos naturales comerciales del departamento del Cauca-Colombia”. Revista Colombiana de Ciencias Químico-Farmacéuticas 48, no. 3 (setembro 1, 2019). Acessado janeiro 22, 2025. https://revistas.unal.edu.co/index.php/rccquifa/article/view/84992.

Vancouver

1.
Giraldo JM, Benítez Benítez R, Sarria-Villa RA, Arango PA, Franco JM. Determinación y comparación cualitativa de cannabinoides presentes en productos naturales comerciales del departamento del Cauca-Colombia. Rev. Colomb. Cienc. Quím. Farm. [Internet]. 1º de setembro de 2019 [citado 22º de janeiro de 2025];48(3). Disponível em: https://revistas.unal.edu.co/index.php/rccquifa/article/view/84992

Baixar Citação

CrossRef Cited-by

CrossRef citations1

1. Paola Andrea Arango Romero, Jhan Carlos Delgado, Sandra Marcela Muñoz, Luis Llanos, Ricardo Benítez. (2024). Actividad antioxidante de variedades de cannabis del Norte del Cauca, Colombia. Ciencia en Desarrollo, 15(1), p.178. https://doi.org/10.19053/01217488.v15.n1.2024.15214.

Dimensions

PlumX

Acessos à página de resumo

1307

Downloads

Não há dados estatísticos.