Journal:The cannabis terpenes

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Full article title The cannabis terpenes
Journal Molecules
Author(s) Sommano, Sarana R.; Chittasupho, Chuda; Ruksiriwanich, Warintorn; Jantrawut, Pensak
Author affiliation(s) Chiang Mai University
Primary contact Email: sarana dot s at cmu dot ac dot th
Editors Valgimigli, Luca
Year published 2020
Volume and issue 25(24)
Article # 5792
DOI 10.3390/molecules25245792
ISSN 1420-3049
Distribution license Creative Commons Attribution 4.0 International
Website https://www.mdpi.com/1420-3049/25/24/5792/htm
Download https://www.mdpi.com/1420-3049/25/24/5792/pdf (PDF)
Emblem-important-yellow.svg This article should be considered a work in progress and incomplete. Consider this article incomplete until this notice is removed.

Abstract

Terpenes are the primary constituents of essential oils and are responsible for the aroma characteristics of the Cannabis plant. Together with cannabinoids, terpenes illustrate a potential synergic and/or entourage effect, with their interactions having only been speculated on for the last few decades. Hundreds of terpenes have been identified that additionally add to the overall cannabis sensory experience, contributing largely to the consumer’s experiences, as well as the market price. These terpenes also enhance many therapeutic efforts, especially as aromatherapy. To shed light on the importance of terpenes in the cannabis industry, the purpose of this review is to morphologically describe sources of cannabis terpenes and to explain the biosynthesis and diversity of terpene profiles in different cannabis chemotypes.

Introduction

Cannabis sativa L. or Cannabis is a herbaceous annual that has a long history of use around the world as fiber, food, oil, and medicine. Depending on the purpose of utilization, cannabis can be called by different names, for example, “hemp” as a fiber and textile crop, and “recreational cannabis,” also known in the United States as "marijuana." Aside from its quality as an industrial textile, the psychoactive properties have placed a stigma on Cannabis plants as an illicit drug, with many informal names including pot, dope, grass, weed, Mary Jane, bud, hash, bhang, kef, ganja, locoweed, reefer, doob, spliff, toke, and roach. It has been forbidden to grow in many countries due to its psychoactive constituents.[1] From a medical perspective, many recent studies have advised that an increase in cannabis use is associated with psychiatric symptoms, including depression and anxiety.[2][3] However, many users still exclusively endorse its recreational purpose.[4][5] As a result, there has been a strong movement toward correcting negative attitudes about Cannabis, and attempts have been made in trying to remove this plant from narcotic lists. In Thailand, for instance, as of 2020, cannabis strains such as กัญชง (hemp) and กัญชา (marijuana) are legally grown for industrial fiber or medicinal purposes based on the controlled level of active metabolites, including cannabinoids such as Δ9–tetrahydrocannabinol (THC) and cannabidiol (CBD).[6] While primary focus has been paid to the bioactive functions of the cannabinoids, the hydrocarbon terpenes could also potentially offer interesting entourage effects that could ideally synergize or downstream their effects.[7] Eminently, with the rise in the legal cannabis industry, interest has grown around cannabis terpenes as they contribute many of the different aromatic characteristics that influence the diverse varieties of cannabis strains.[8]

Within the scope of this review, we provide the general background history of cannabis discovery and the importance of terpenes. The taxonomy and morphology of cannabis, particularly in regards to the localization of its terpenes, are discussed. More importantly, the chemistry, biosynthesis, and diversity of terpenes in different cannabis genotypes are of major interest in this review.

The cannabis discovery and its importance as a source of terpene

Cannabis has a long history dating back approximately to just after the Ice Age, as cord and textile scraps made of cannabis fiber have been found in historic caves in the Czech Republic.[9][10] In the nineteenth century, the plant was recorded as originating near the southern area of the Caspian Sea near Iran (Figure 1b).[11][12] It was later confirmed by the chemotaxonomy of the essential oil from cannabis of diverse origins, and most of the cannabis phenotypes collected around the globe had chemical ingredients similar to those of Central Asian origin.[13] In previous days, it was known as the original fiber plant in Asian culture. Seed and seed oil extracts were also used as food.[11][14] The first record of cannabis in the literature in China can be dated to approximately 5,000 years ago, as written by emperor Chen Nong, who was then known as the father of Chinese agriculture. The Chinese alphabet's “Ma” was created using the mimic of the cannabis drying process (Figure 1a). The letter was adjusted to describe the male plant, “his” separated from the female plant, “chu” for the quality of the fiber.[15][16] In 500 BC, the use of cannabis spread worldwide from Asia to Europe and to Africa through the silk road. In the nineteenth century, hemp was popular in the western world as a fiber crop that had superior qualities.[17][18] It is not too surprising therefore that cannabis is today known as an ideal plant in terms of sustainability. In a period of rapid industrial growth, hemp became the industrial crop as countries raced against one another toward modernity. In addition to the world textile industry, the plant began to be known for its medical uses. It was believed that during the nineteenth century, there were thousands of cannabis medicines available, produced by more than 280 manufacturers.[19] However, the growth and interest in this fiber crop crashed after the attempt to add it to the narcotic list with opium during the 1925 International Opium Convention in Geneva.[19]



References

  1. ↑ Chaohua, Cheng; Gonggu, Zang; Lining, Zhao; Chunsheng, Gao; Qing, Tang; Jianhua, Chen; Xinbo, Guo; Dingxiang, Peng et al. (1 May 2016). "A rapid shoot regeneration protocol from the cotyledons of hemp (Cannabis sativa L.)" (in en). Industrial Crops and Products 83: 61–65. doi:10.1016/j.indcrop.2015.12.035. https://linkinghub.elsevier.com/retrieve/pii/S0926669015306245. 
  2. ↑ Weinberger, Andrea H.; Zhu, Jiaqi; Levin, Jacob; Barrington-Trimis, Jessica L.; Copeland, Jan; Wyka, Katarzyna; Kim, June H.; Goodwin, Renee D. (1 September 2020). "Cannabis use among US adults with anxiety from 2008 to 2017: The role of state-level cannabis legalization". Drug and Alcohol Dependence 214: 108163. doi:10.1016/j.drugalcdep.2020.108163. ISSN 1879-0046. PMID 32707516. https://pubmed.ncbi.nlm.nih.gov/32707516. 
  3. ↑ Rabiee, Rynaz; Lundin, Andreas; Agardh, Emilie; Hensing, Gunnel; Allebeck, Peter; Danielsson, Anna-Karin (1 November 2020). "Cannabis use and the risk of anxiety and depression in women: A comparison of three Swedish cohorts". Drug and Alcohol Dependence 216: 108332. doi:10.1016/j.drugalcdep.2020.108332. ISSN 1879-0046. PMID 33080503. https://pubmed.ncbi.nlm.nih.gov/33080503. 
  4. ↑ Lloyd, Shawnta L.; Lopez-Quintero, Catalina; Striley, Catherine W. (1 November 2020). "Sex differences in driving under the influence of cannabis: The role of medical and recreational cannabis use". Addictive Behaviors 110: 106525. doi:10.1016/j.addbeh.2020.106525. ISSN 1873-6327. PMC 7443537. PMID 32711286. https://pubmed.ncbi.nlm.nih.gov/32711286. 
  5. ↑ Turna, Jasmine; Balodis, Iris; Munn, Catharine; Van Ameringen, Michael; Busse, Jason; MacKillop, James (1 October 2020). "Overlapping patterns of recreational and medical cannabis use in a large community sample of cannabis users". Comprehensive Psychiatry 102: 152188. doi:10.1016/j.comppsych.2020.152188. ISSN 1532-8384. PMID 32653594. https://pubmed.ncbi.nlm.nih.gov/32653594. 
  6. ↑ Theparat, C. (29 January 2020). "New rule makes it legal to grow hemp". Bangkok Post. https://www.bangkokpost.com/thailand/general/1845714/new-rule-makes-it-legal-to-grow-hemp. Retrieved 02 October 2020. 
  7. ↑ Koltai, Hinanit; Namdar, Dvora (1 October 2020). "Cannabis Phytomolecule 'Entourage': From Domestication to Medical Use". Trends in Plant Science 25 (10): 976–984. doi:10.1016/j.tplants.2020.04.007. ISSN 1878-4372. PMID 32417167. https://pubmed.ncbi.nlm.nih.gov/32417167. 
  8. ↑ Booth, Judith K.; Bohlmann, Jörg (1 July 2019). "Terpenes in Cannabis sativa – From plant genome to humans" (in en). Plant Science 284: 67–72. doi:10.1016/j.plantsci.2019.03.022. https://linkinghub.elsevier.com/retrieve/pii/S0168945219301190. 
  9. ↑ Clarke, R.; Merlin M., ed. (1 September 2013). "History of Cannabis Use for Fiber". Cannabis: Evolution and Ethnobotany. University of California Press. doi:10.1525/9780520954571-011. ISBN 978-0-520-95457-1. https://california.degruyter.com/view/title/554936. 
  10. ↑ Fleming, M.P.; Clarke R.C. (1998). "Physical evidence for the antiquity of Cannabis sativa L.". Journal of the International Hemp Association 5 (2): 80–92. http://www.internationalhempassociation.org/jiha/jiha5208.html. 
  11. ↑ 11.0 11.1 Li, Hui-Lin (1 October 1973). "An archaeological and historical account of cannabis in China" (in en). Economic Botany 28 (4): 437–448. doi:10.1007/BF02862859. ISSN 0013-0001. http://link.springer.com/10.1007/BF02862859. 
  12. ↑ Li, Hui-Lin (1 July 1974). "The origin and use of cannabis in eastern asia linguistic-cultural implications" (in en). Economic Botany 28 (3): 293–301. doi:10.1007/BF02861426. ISSN 0013-0001. http://link.springer.com/10.1007/BF02861426. 
  13. ↑ Hillig, Karl W (1 October 2004). "A chemotaxonomic analysis of terpenoid variation in Cannabis" (in en). Biochemical Systematics and Ecology 32 (10): 875–891. doi:10.1016/j.bse.2004.04.004. https://linkinghub.elsevier.com/retrieve/pii/S0305197804001012. 
  14. ↑ Aluko, R.E. (2017), "Hemp Seed (Cannabis sativa L.) Proteins" (in en), Sustainable Protein Sources (Elsevier): 121–132, doi:10.1016/b978-0-12-802778-3.00007-x, ISBN 978-0-12-802778-3, https://linkinghub.elsevier.com/retrieve/pii/B978012802778300007X 
  15. ↑ Abel, Ernest L. (1980), "Cannabis in the Ancient World" (in en), Marihuana (Boston, MA: Springer US): 3–35, doi:10.1007/978-1-4899-2189-5_1, ISBN 978-1-4899-2191-8, http://link.springer.com/10.1007/978-1-4899-2189-5_1 
  16. ↑ Bonini, Sara Anna; Premoli, Marika; Tambaro, Simone; Kumar, Amit; Maccarinelli, Giuseppina; Memo, Maurizio; Mastinu, Andrea (5 December 2018). "Cannabis sativa: A comprehensive ethnopharmacological review of a medicinal plant with a long history". Journal of Ethnopharmacology 227: 300–315. doi:10.1016/j.jep.2018.09.004. ISSN 1872-7573. PMID 30205181. https://pubmed.ncbi.nlm.nih.gov/30205181. 
  17. ↑ Mediavilla, V; Leupin, M; Keller, A (1 January 2001). "Influence of the growth stage of industrial hemp on the yield formation in relation to certain fibre quality traits" (in en). Industrial Crops and Products 13 (1): 49–56. doi:10.1016/S0926-6690(00)00052-2. https://linkinghub.elsevier.com/retrieve/pii/S0926669000000522. 
  18. ↑ Cosentino, Salvatore L.; Riggi, Ezio; Testa, Giorgio; Scordia, Danilo; Copani, Venera (1 October 2013). "Evaluation of European developed fibre hemp genotypes (Cannabis sativa L.) in semi-arid Mediterranean environment" (in en). Industrial Crops and Products 50: 312–324. doi:10.1016/j.indcrop.2013.07.059. https://linkinghub.elsevier.com/retrieve/pii/S0926669013003968. 
  19. ↑ 19.0 19.1 Bewley-Taylor, D.; Blickman T.; Jelsma, M. (March 2014). "The Rise and Decline of Cannabis Prohibition: The History of Cannabis in the UN Drug Control System and Options for Reform". In Aronson, D. (PDF). Transnational Institute. https://www.tni.org/files/download/rise_and_decline_web.pdf. 

Notes

This presentation is faithful to the original, with only a few minor changes to presentation. Some grammar and punctuation was cleaned up to improve readability. In some cases important information was missing from the references, and that information was added.

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