Abstract
Cannabis sativa L. is a psychoactive plant that contains more than 500 chemical components. Even though the consumption (in the form of marijuana, hashish, or hashish oil) for recreational purposes, is the most popular way of using the plant, the knowledge of its components has also led to classify Cannabis sativa L. is a plant with medicinal or therapeutical use. Several comprehensive reviews have already been published focused on the chemical composition of Cannabis sativa. In this chapter, we will summarize relevant information about those components, which may help to understand its biological actions that will be described in the following chapters.
Access this chapter
Tax calculation will be finalised at checkout
Purchases are for personal use only
References
Andre CM, Hausman JF, Guerriero G (2016) Cannabis sativa: the Plant of the Thousand and one Molecules. Front Plant Sci 7:19
Andre CM, Larondelle Y, Evers D (2010) Dietary antioxidants and oxidative stress from a human and plant perspective: a review. Curr Nutr Food Sci 6:2–12
Appendino G, Gibbons S, Giana A, Pagani A, Grassi G, Stavri M (2008) Antibacterial cannabinoids from Cannabis sativa: a structure-activity study. J Nat Prod 71:1427–1430
Arts IC, Hollman PC (2005) Polyphenols and disease risk in epidemiologic studies. Am J Clin Nutr 81:317–325
Barrett ML, Scutt AM, FJ Evans FJ (1986) Cannflavin a and B, prenylated flavones from Cannabis sativa L. Experientia 42(4):452–453
Brenneisen R (2007) Chemistry and analysis of phytocannabinoids and other cannabis constituents. In: Elsohly M (ed) Marijuana and the cannabinoids. Humana Press, Totowa, NY, pp 17–49
Burstein S (2015) Cannabidiol (CBD) and its analogs: a review of their effects on inflammation. Bioorg Med Chem 23(7):1377–1385
Dajas F, Abin A, Arredondo F, Echeverry C, Rivera F (2013) Neuroprotective actions of flavones and flavonols: mechanisms and relationship to flavonoid structural features. Cent Nerv Syst Agents Med Chem 13(1):30–35
De Petrocellis L, Orlando P, Moriello AS, Aviello G, Stott C, Izzo AA, di Marzo V (2012) Cannabinoid actions at TRPV channels: effects on TRPV3 and TRPV4 and their potential relevance to gastrointestinal inflammation. Acta Physiol 204:255
Echeverry C, Arredondo F, Martinez M, Abin-Carriquiry JA, Midiwo J, Dajas F (2015) Antioxidant activity, cellular bioavailability, iron and calcium management of neuroprotective and non- neuroprotective flavones. Neurotox Res 27:31–42
ElSohly MA, Slade D (2005) Chemical constituents of marijuana: the complex mixture of natural cannabinoids. Life Sci 78:539–548
ElSohly MA, Turner CE, Phoebe CH, Knapp JE, Schiff PL, Slatkin DJ (1978) Anhydrocannabisativine, a new alkaloid from Cannabis sativa. J Pharm Sci 67:124
Elzinga S, Fischedick J, Podkolinski R et al (2015) Cannabinoids and terpenes as chemotaxonomic markers in cannabis. Nat Prod Chem Res 3:1–9
Fellermeier M, Zenk MH (1998) Prenylation of olivetolate by a hemp transferase yields cannabigerolic acid, the precursor of tetrahydrocannabinol. FEBS Lett 427(2):283–285
Fischedick JT, Hazekamp A, Erkelens T et al (2010) Metabolic fingerprinting of Cannabis sativa L., cannabinoids and terpenoids for chemotaxonomic and drug standardization purposes. Phytochemistry 71:2058–2073
Flores-Sanchez IJ, Verpoorte R (2008) PKS activities and biosynthesis of cannabinoids and flavonoids in Cannabis sativa L. plants. Plant Cell Physiol 49(12):1767–1782
Fukumoto S, Sawasaki E, Okuyama S, Miyake Y, Yokogoshi H (2006) Flavor components of monoterpenes in citrus essential oils enhance the release of monoamines from rat brain slices. Nutr Neurosci 9:73–80
Gagne SJ, Stout JM, Liu E, Boubakir Z, Clark SM, Page JE (2012) Identification of olivetolic acid cyclase from Cannabis sativa reveals a unique catalytic route to plant polyketides. Proc Natl Acad Sci U S A 109(31):12811–12816
Gaoni Y, Mechoulam R (1964) Isolation, structure, and partial synthesis of an active constituent of Hashish. J Am Chem Soc 86(8):1646–1647
Gertsch J, Pertwee RG, Di Marzo V (2010) Phytocannabinoids beyond the cannabis plant - do they exist? Br J Pharmacol 160:523–529
Giacoppo S, Mandolino G, Galuppo M, Bramanti P, Mazzon E (2014) Cannabinoids: new promising agents in the treatment of neurological diseases. Molecules 19(11):18781–18816
Hendriks H, Malingré TM, Batterman S, Bos R (1975) Mono- and sesqui-terpene hydrocarbons of the eseential oil of Cannabis sativa. Phytochemistry 14:814–815
Hill AJ, Williams CM, Whalley BJ, Stephens GJ (2012) Phytocannabinoids as novel therapeutic agents in CNS disorders. Pharmacol Ther 133(1):79–97
Kim ES, Mahlberg PG (2003) Secretory vesicle formation in the secretory cavity of glandular trichomes of Cannabis sativa L. (Cannabaceae). Mol Cells 15(3):387–395
Malingré T, Hendriks H, Batterman S, Bos R, Visser J (1975) The essential oil of Cannabis sativa. Planta Med 28(1):56–61
Mc Partland JM, Mediavilla V (2002) Noncannabinoid components. In: Grothenhermen F, Russo E (eds) Cannabis and cannabinoids: pharmacology, toxicology and therapeutic potential. The Haworth Integrative Healing Press, New York, pp 401–409
Mechoulam R (1988) Alkaloids in Cannabis sativa L. In: Brossi A (ed) The alkaloids. Academic, San Diego, pp 77–93
Mechoulam R, Hanus L (2000) A historical overview of chemical research on cannabinoids. Chem Phys Lipids 108:1–13
Mechoulam R, Shvo Y, Hashish I (1963) The structure of cannabidiol. Tetrahedron 19(12):2073–2078
Meier C, Mediavilla V (1998) Factors influencing the yield and the quality of hemp (Cannabis sativa L.) essential oil. J Int Hemp Assoc 5:16–20
Meijer EPM, de Hammond KM, Micheler M (2009) The inheritance of chemical phenotype in Cannabis sativa L. (III): variation in cannabichromene proportion. Euphytica 165:293–311
Morales P, Hurst DP, Reggio PH (2017) Molecular targets of the Phytocannabinoids: a complex picture. Prog Chem Org Nat Prod 103:103–131
Niesink RJ, Rigter S, Koeter MW, Brunt TM (2015) Potency trends of Δ(9) -tetrahydrocannabinol, cannabidiol and cannabinol in cannabis in the Netherlands: 2005-15. Addiction 110(12):1941–1950
Pacher P, Batkai S, Kunos G (2006) The endocannabinoid system as an emerging target of pharmacotherapy. Pharmacol Rev 58:389–462
Pertwee RG (1997) Pharmacology of cannabinoid CB1 and CB2 receptors. Pharmacol Ther 74(2):129–180
Radwan MM, Elsohly MA, Slade D, Ahmed SA, Wilson L, El-Alfy AT, Khan IA, Ross SA (2008) Non-cannabinoid constituents from a high potency Cannabis sativa variety. Phytochemistry 69(14):2627–2633
Ross SA, ElSohly MA (1996) The volatile oil composition of fresh and air-dried buds of Cannabis sativa. J Nat Prod 59(1):49–51
Ross SA, ElSohly MA, Sultana GNN, Mehmedic Z, Hossain CF, Chandra S (2005) Flavonoid glycosides and cannabinoids from the pollen of Cannabis sativa L. Phytochem Anal 16:45–48
Ross SA, Mehmedic Z, Murphy TP, ElSohly MA (2000) GC-MS analysis of the total Δ9-THC content of both drug- and fiber-type Cannabis seeds. J Anal Toxicol 4:715–717
Russo EB (2011) Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects. Br J Pharmacol 163(7):1344–1364
Singh B, Sharma R (2015) Plant terpenes: defense responses, phylogenetic analysis, regulation and clinical applications. Biotechnol 5:129–151
Sirikantaramas S, Morimoto S, Shoyama Y, Ishikawa Y, Wada Y, Shoyama Y, Taura F (2004) The gene controlling marijuana psychoactivity: molecular cloning and heterologous expression of Delta1-tetrahydrocannabinolic acid synthase from Cannabis sativa L. J Biol Chem 279(38):39767–39774
Sirikantaramas S, Taura F, Morimoto S, Shoyama Y (2007) Recent advances in Cannabis sativa research: biosynthetic studies and its potential in biotechnology. Curr Pharm Biotechnol 8:237–243
Sirikantaramas S, Taura F, Tanaka Y, Ishikawa Y, Morimoto S, Shoyama Y (2005) Tetrahydrocannabinolic acid synthase, the enzyme controlling marijuana psychoactivity, is secreted into the storage cavity of the glandular trichomes. Plant Cell Physiol 46(9):1578–1582
Slatkin DJ, Doorenbos NJ, Harris LS, Masoud AN, Quimby MW, Schiff PL Jr (1971) Chemical constituents of Cannabis sativa L. root. J Pharm Sci 60(12):1891–1892
Small E (2015) Evolution and classification of Cannabis sativa (marijuana, hemp) in relation to human utilization. Bot Rev 81:189–294
Smeds AI, Eklund PC, William SM (2012) Content, composition, and stereochemical characterisation of lignans in berries and seeds. Food Chem 134:1991–1998
Stogner JM, Miller BL (2015) Assessing the dangers of "dabbing": mere marijuana or harmful new trend? Pediatrics 136(1):1–3
Stout JM, Boubakir Z, Ambrose SJ, Purves RW, Page JE (2012) The hexanoyl-CoA precursor for cannabinoid biosynthesis is formed by an acyl-activating enzyme in Cannabis sativa trichomes. Plant J 71:353–365
Swift W, Wong A, Li KM, Arnold JC, McGregor IS (2013) Analysis of cannabis seizures in NSW, Australia: cannabis potency and cannabinoid profile. PLoS One 8(7):e70052
Taura F, Sirikantaramas S, Shoyama Y, Yoshikai K, Shoyama Y, Morimoto S (2007) Cannabidiolic-acid synthase, the chemotype-determining enzyme in the fiber-type Cannabis sativa. FEBS Lett 581(16):2929–2934
Turner CE, Elsohly MA, Boeren EG (1980) Constituents of Cannabis sativa L.17. A review of the natural constituents. J Nat Prod 43(2):169–234
Vanhoenacker G, Van Rompaey P, De Keukeleire D, Sandra P (2002) Chemotaxonomic features associated with flavonoids of cannabinoid-free cannabis (Cannabis sativa subsp. sativa L.) in relation to hops (Humulus lupulus L.). Nat Prod Lett 16(1):57–63
Vara D, Morell C, Rodríguez-Henche N, Diaz-Laviada I (2013) Involvement of PPARγ in the antitumoral action of cannabinoids on hepatocellular carcinoma. Cell Death Dis 4:e618
Wood TB, Spivey WTN, Easterfield TH (1899) Cannabinol, Part I. J Chem Soc 75:20–36
Acknowledgments
Partially supported by FONDECYT-CHILE (Grant 1170662 to M. R-P) and PEDECIBA (Uruguay).
Author information
Authors and Affiliations
Corresponding author
Editor information
Editors and Affiliations
Rights and permissions
Copyright information
© 2021 Springer Nature Switzerland AG
About this chapter
Cite this chapter
Echeverry, C., Reyes-Parada, M., Scorza, C. (2021). Constituents of Cannabis sativa. In: Monti, J.M., Pandi-Perumal, S.R., Murillo-Rodríguez, E. (eds) Cannabinoids and Sleep. Advances in Experimental Medicine and Biology, vol 1297. Springer, Cham. https://doi.org/10.1007/978-3-030-61663-2_1
Download citation
DOI: https://doi.org/10.1007/978-3-030-61663-2_1
Published:
Publisher Name: Springer, Cham
Print ISBN: 978-3-030-61662-5
Online ISBN: 978-3-030-61663-2
eBook Packages: Biomedical and Life SciencesBiomedical and Life Sciences (R0)