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==Introduction==
==Introduction==
[[Hemp]] ([[Cannabis sativa|''Cannabis sativa'' L.]]) originated from central Asia and has been used for human and animal food, as a source of fiber for ropes, and in [[Cannabis (drug)|medicine]].<ref name="HilligGenetic05">{{cite journal |title=Genetic evidence for speciation in ''Cannabis'' (Cannabaceae) |journal=Genetic Resources and Crop Evolution |author=Hillig, K.W. |volume=52 |pages=161–80 |year=2005 |doi=10.1007/s10722-003-4452-y}}</ref><ref name="CriniAppli20">{{cite journal |title=Applications of hemp in textiles, paper industry, insulation and building materials, horticulture, animal nutrition, food and beverages, nutraceuticals, cosmetics and hygiene, medicine, agrochemistry, energy production and environment: A review |journal=Environmental Chemistry Letters |author=Crini, G.; Lichtfouse, E.; Chanet, G. et al. |volume=18 |pages=1451–76 |year=2020 |doi=10.1007/s10311-020-01029-2}}</ref> It contains more than 500 [[phytochemical]]s with many therapeutic purposes and has been used to treat epilepsy, Alzheimer’s disease, Parkinson’s disease, multiple sclerosis, pain and nausea in cancer patients, diabetes, and eating disorders.<ref name="NamdarVaria18">{{cite journal |title=Variation in the compositions of cannabinoid and terpenoids in Cannabis sativa derived from inflorescence position along the stem and extraction methods |journal=Industrial Crops and Products |author=Namdar, D.; Mazuz, M.; Ion, A. et al. |volume=113 |pages=376–82 |year=2018 |doi=10.1016/j.indcrop.2018.01.060}}</ref>
The most well-known phytochemicals are secondary metabolites, such as [[cannabinoid]]s and [[Terpene|terpenoids]].<ref name="TurnerQuant78">{{cite journal |title=Quantitative Determination of Cannabinoids in Individual Glandular Trichomes of ''Cannabis sativa'' L. (Cannabaceae) |journal=American Journal of Botany |author=Turner, J.C.; Hemphill, J.K.; Mahlberg, P.G. |volume=65 |issue=10 |pages=1103–6 |year=1978 |doi=10.1002/j.1537-2197.1978.tb06177.x}}</ref> More than 150 cannabinoids have already been identified in hemp.<ref name="HanušPhyto16">{{cite journal |title=Phytocannabinoids: A unified critical inventory |journal=Natural Product Reports |author=Hanuš, L.O.; Meyer, S.M.; Muñoz, E. et al. |volume=33 |pages=1357–92 |year=2016 |doi=10.1039/C6NP00074F}}</ref> The most active and studied compounds are [[Tetrahydrocannabinol|Δ<sup>9</sup> tetrahydrocannabinol]] (Δ<sup>9</sup>-THC), [[cannabidiol]] (CBD), [[cannabigerol]] (CBG), [[cannabichromene]] (CBC), and their carboxylated forms.<ref name="NamdarVaria18" /> Terpenoids in [[Cannabis concentrate|essential oil]] are divided into monoterpenes and sesquiterpenes, which are responsible for hemp fragrance and flavor and also contribute to therapeutic effects. There are generally fewer sesquiterpenes than monoterpenes detected in hemp flowers. The highest content of cannabinoids and terpenoids is found in the glandular [[trichome]]s on bracts.<ref name="BertoliFibre10">{{cite journal |title=Fibre hemp inflorescences: From crop-residues to essential oil production |journal=Industrial Crops and Products |author=Bertoli, A.; Tozzi, S.; Pistelli, L. et al. |volume=32 |issue=3 |pages=329–37 |year=2010 |doi=10.1016/j.indcrop.2010.05.012}}</ref>
Precursors for cannabinoids have two biosynthetic pathways. The polyketide pathway leads to olivetolic acid (OLA), and the plastidial 2-C-methyl-D-erytritol 4-phosphate (MEP) pathway leads to geranyl diphosphate (GPP). Precursors OLA and GPP form [[cannabigerolic acid]] (CBG-A), which is a precursor for different cannabinoids, as well as [[tetrahydrocannabinolic acid]] (THCA), [[cannabidiolic acid]] (CBDA), and [[cannabichromenic acid]] (CBCA).<ref name="AndreCannabis16">{{cite journal |title=''Cannabis sativa'': The plant of the thousand and one molecules |journal=Frontiers in Plant Medicine |author=Andre, C.M.; Hausman, J.-F.; Guerriero, G. |volume=7 |pages=19 |year=2016 |doi=10.3389/fpls.2016.00019 |pmid=26870049 |pmc=PMC4740396}}</ref> Terpenoids are composed of isoprene units. Similar to cannabinoids, terpenoids also have different biosynthetic pathways. Sesquiterpenes and triterpenes are formed from the cytosolic mevalonic acid (MVA) pathway, while monoterpenes, diterpenes, and tetraterpenes are formed via the plastid-localized (MEP) pathway. Subsequently, precursors of sesquiterpene farnesyl diphosphate (FPP) and monoterpene geranyl diphosphate are formed.<ref name="AndreCannabis16" />
Terpenoids and cannabinoids may have a synergistic effect on human and animal health.<ref name="RussoTaming11">{{cite journal |title=Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects |journal=British Journal of Pharmacology |author=Russo, E.B. |volume=163 |issue=7 |pages=1344–64 |year=2011 |doi=10.1111/j.1476-5381.2011.01238.x}}</ref> An example of the positive effects of the combined use of cannabinoids and terpenoids is acne therapy, in which CBD, [[limonene]], [[linalool]], and [[pinene]] are involved. Cannabinoids and terpenoids such as CBG and pinene also have a combined effect on MRSA (methicillin-resistant Staphylococcus aureus).<ref name="DaSilvaBiological12">{{cite journal |title=Biological Activities of a-Pinene and β-Pinene Enantiomers |journal=Molecules |author=da Silva, A.C.R.; Lopes, P.M.; de Azevedo, M.M.B. et al. |volume=17 |issue=6 |pages=6305-6316 |year=2012 |doi=10.3390/molecules17066305}}</ref><ref name="AppendinoAntibact08">{{cite journal |title=Antibacterial Cannabinoids from ''Cannabis sativa'': A Structure−Activity Study |journal=Journal of Natural Products |author=Appendino, G.; Gibbons, S.; Giana, A. et al. |volume=71 |issue=8 |pages=1427–30 |year=2008 |doi=10.1021/np8002673}}</ref> However, the issue of synergy remains controversial and needs further investigation.
According to the chemical composition, there are five major hemp [[chemotype]]s. Small and Beckstead<ref name="SmallCommon73">{{cite journal |title=Common cannabinoid phenotypes in 350 stocks of ''Cannabis'' |journal=Lloydia |author=Small, E.; Beckstead, H.D. |volume=36 |issue=2 |pages=144–65 |year=1973 |pmid=4744553}}</ref> determined three chemotypes: chemotype I, with a THC content higher than 0.3% and CBD content lower than 0.5%; chemotype II (intermediate type), with a THC and CBD ratio that is roughly equal; and chemotype III, with a higher CBD content than 0.5% and THC content lower than 0.3% of the flower dry matter. Later, Fournier ''et al.''<ref name="FournierIdent87">{{cite journal |title=Identification of a new chemotype in Cannabis sativa: cannabigerol-dominant plants, biogenetic and agronomic prospects |journal=Planta Medica |author=Fournier, G.; Richez-Dumanois, C.; Duvezin, J. et al. |volume=53 |issue=3 |pages=277–80 |year=1987 |doi=10.1055/s-2006-962705 |pmid=3628560}}</ref> determined two other chemotypes: chemotype IV, with a prevalence of CBG higher than 0.3% of the flower dry matter, and chemotype V, with an undetectable content of cannabinoids.
Numerous scientists have studied species and subspecies of ''Cannabis''.<ref name="PollioTheName16">{{cite journal |title=The Name of Cannabis: A Short Guide for Nonbotanists |journal=Cannabis and Cannabinoid Research |author=Pollio, A. |volume=1 |issue=1 |pages=234-238 |year=2016 |doi=10.1089/can.2016.0027 |pmid=28861494 |pmc=PMC5531363}}</ref> In general, it is known that hemp and marijuana differ based on THC content. Hemp is supposed to have THC content below 0.2–1%, which depends on the legislation of different countries, while marijuana could reach THC content up to 20 to 30% in dry [[inflorescence]]s.<ref name="SchillingCanna20">{{cite journal |title=''Cannabis sativa'' |journal=Current Biology |author=Schilling, S.; Melzer, R.; McCabe, P.F. |volume=30 |issue=1 |pages=R8–R9 |year=2020 |doi=10.1016/j.cub.2019.10.039 |pmid=31910378}}</ref> In 2015, Sawler ''et al.''<ref name="SawlerTheGen15">{{cite journal |title=The Genetic Structure of Marijuana and Hemp |journal=PLoS One |author=Sawler, J.; Stout, J.M.; Gardner, K.M. et al. |volume=10 |issue=8 |at=e0133292 |year=2015 |doi=10.1371/journal.pone.0133292 |pmid=26308334 |pmc=PMC4550350}}</ref> determined that hemp and marijuana significantly differ at the genome level, that different marijuana types are often not genetically close, and that THC is not related to the genetic distinction between hemp and marijuana. Hemp has been used for food and fibers, while marijuana was mostly used in traditional medicine.<ref name="JanatováYield18">{{cite journal |title=Yield and cannabinoids contents in different cannabis (''Cannabis sativa'' L.) genotypes for medical use |journal=Industrial Crops and Products |author=Janatová, A.; Fraňková, A.; Tlustoš, P. et al. |volume=112 |pages=363–67 |year=2018 |doi=10.1016/j.indcrop.2017.12.006}}</ref> However, marijuana was [[Legality of cannabis|prohibited and criminalized]] all around the world due to the psychoactive nature of THC. In 1988, the United Nations Convention against Illicit Traffic in Narcotic Drugs and Psychotropic Substances prohibited the use, production, and cultivation of ''Cannabis'' plants, which was recognized as a narcotic drug with psychotropic compounds, still posing a major problem in the legalization of cannabis with higher THC content.<ref name="AguilarMedicinal18">{{cite web |url=https://idpc.net/publications/2018/04/medicinal-cannabis-policies-and-practices-around-the-world |title=Medicinal cannabis policies and practices around the world |author=Aguilar, S.; Gutiérrez, V.; Sánchez, L. et al. |publisher=International Drug Policy Consortium |date=23 April 2018 |accessdate=19 April 2021}}</ref> Due to many different research studies based on the positive effects of cannabis on numerous diseases, more and more countries are slowly revising their legislation in favor of growing ''Cannabis'' plants for medical and scientific purposes in restricted area.




Revision as of 21:32, 10 June 2021

Full article title Metabolomic analysis of cannabinoid and essential oil profiles in different hemp (Cannabis sativa L.) phenotypes
Journal Plants
Author(s) Eržen, Marjeta; Košir, Iztok J.; Ocvirk, Miha; Kreft, Samo; Čerenak, Andreja
Author affiliation(s) Slovenian Institute of Hop Research and Brewing, University of Ljubljana
Primary contact Email: andreja dot cerenak at ihps dot si
Year published 2021
Volume and issue 10(5)
Article # 966
DOI 10.3390/plants10050966
ISSN 2223-7747
Distribution license Creative Commons Attribution 4.0 International
Website https://www.mdpi.com/2223-7747/10/5/966/htm
Download https://www.mdpi.com/2223-7747/10/5/966/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

Hemp (Cannabis sativa L.) cannabinoids and terpenoids have therapeutic effects on human and animal health. Cannabis plants can often have a relatively high heterogeneity, which leads to different phenotypes that have different chemical profiles despite being from the same variety. Little information exists about cannabinoid and terpenoid profiles in different hemp phenotypes within the same variety. For this study, 11 phenotypes from three different varieties—Carmagnola Selected (CS), Tiborszallasi (TS), and Finola Selection (FS)—were analyzed. The components of essential oil (29) were analyzed using gas chromatography with flame ionization detection (GC-FID), and 10 different cannabinoids of each phenotype were determined using high-performance liquid chromatography (HPLC).

Principal component analysis (PCA) and analysis of variance (ANOVA) showed that according to the components of essential oil, FS and TS plants were more uniform than CS plants, where there were great differences between CI and CII phenotypes. The content of cannabidiolic acid (CBDA) was the highest in all four FS phenotypes. By comparing cannabinoid profiles, FS was clearly separated from TS and CS, while these two varieties were not clearly distinguishable. Phenotypes TV and CI had the highest total content of tetrahydrocannabinol (Δ9-THC), while all phenotypes of FS had the highest total content of cannabidiol (CBD). The highest total content of cannabigerol (CBG) was determined in phenotype CI. Obtained results are useful for the development of new supplementary ingredients, for different pharmacy treatments, and for further breeding purposes.

Keywords: Cannabis sativa L., Cannabaceae, cannabinoids, essential oils, terpenes, GC-FID, HPLC

Introduction

Hemp (Cannabis sativa L.) originated from central Asia and has been used for human and animal food, as a source of fiber for ropes, and in medicine.[1][2] It contains more than 500 phytochemicals with many therapeutic purposes and has been used to treat epilepsy, Alzheimer’s disease, Parkinson’s disease, multiple sclerosis, pain and nausea in cancer patients, diabetes, and eating disorders.[3]

The most well-known phytochemicals are secondary metabolites, such as cannabinoids and terpenoids.[4] More than 150 cannabinoids have already been identified in hemp.[5] The most active and studied compounds are Δ9 tetrahydrocannabinol (Δ9-THC), cannabidiol (CBD), cannabigerol (CBG), cannabichromene (CBC), and their carboxylated forms.[3] Terpenoids in essential oil are divided into monoterpenes and sesquiterpenes, which are responsible for hemp fragrance and flavor and also contribute to therapeutic effects. There are generally fewer sesquiterpenes than monoterpenes detected in hemp flowers. The highest content of cannabinoids and terpenoids is found in the glandular trichomes on bracts.[6]

Precursors for cannabinoids have two biosynthetic pathways. The polyketide pathway leads to olivetolic acid (OLA), and the plastidial 2-C-methyl-D-erytritol 4-phosphate (MEP) pathway leads to geranyl diphosphate (GPP). Precursors OLA and GPP form cannabigerolic acid (CBG-A), which is a precursor for different cannabinoids, as well as tetrahydrocannabinolic acid (THCA), cannabidiolic acid (CBDA), and cannabichromenic acid (CBCA).[7] Terpenoids are composed of isoprene units. Similar to cannabinoids, terpenoids also have different biosynthetic pathways. Sesquiterpenes and triterpenes are formed from the cytosolic mevalonic acid (MVA) pathway, while monoterpenes, diterpenes, and tetraterpenes are formed via the plastid-localized (MEP) pathway. Subsequently, precursors of sesquiterpene farnesyl diphosphate (FPP) and monoterpene geranyl diphosphate are formed.[7]

Terpenoids and cannabinoids may have a synergistic effect on human and animal health.[8] An example of the positive effects of the combined use of cannabinoids and terpenoids is acne therapy, in which CBD, limonene, linalool, and pinene are involved. Cannabinoids and terpenoids such as CBG and pinene also have a combined effect on MRSA (methicillin-resistant Staphylococcus aureus).[9][10] However, the issue of synergy remains controversial and needs further investigation.

According to the chemical composition, there are five major hemp chemotypes. Small and Beckstead[11] determined three chemotypes: chemotype I, with a THC content higher than 0.3% and CBD content lower than 0.5%; chemotype II (intermediate type), with a THC and CBD ratio that is roughly equal; and chemotype III, with a higher CBD content than 0.5% and THC content lower than 0.3% of the flower dry matter. Later, Fournier et al.[12] determined two other chemotypes: chemotype IV, with a prevalence of CBG higher than 0.3% of the flower dry matter, and chemotype V, with an undetectable content of cannabinoids.

Numerous scientists have studied species and subspecies of Cannabis.[13] In general, it is known that hemp and marijuana differ based on THC content. Hemp is supposed to have THC content below 0.2–1%, which depends on the legislation of different countries, while marijuana could reach THC content up to 20 to 30% in dry inflorescences.[14] In 2015, Sawler et al.[15] determined that hemp and marijuana significantly differ at the genome level, that different marijuana types are often not genetically close, and that THC is not related to the genetic distinction between hemp and marijuana. Hemp has been used for food and fibers, while marijuana was mostly used in traditional medicine.[16] However, marijuana was prohibited and criminalized all around the world due to the psychoactive nature of THC. In 1988, the United Nations Convention against Illicit Traffic in Narcotic Drugs and Psychotropic Substances prohibited the use, production, and cultivation of Cannabis plants, which was recognized as a narcotic drug with psychotropic compounds, still posing a major problem in the legalization of cannabis with higher THC content.[17] Due to many different research studies based on the positive effects of cannabis on numerous diseases, more and more countries are slowly revising their legislation in favor of growing Cannabis plants for medical and scientific purposes in restricted area.


References

  1. ↑ Hillig, K.W. (2005). "Genetic evidence for speciation in Cannabis (Cannabaceae)". Genetic Resources and Crop Evolution 52: 161–80. doi:10.1007/s10722-003-4452-y. 
  2. ↑ Crini, G.; Lichtfouse, E.; Chanet, G. et al. (2020). "Applications of hemp in textiles, paper industry, insulation and building materials, horticulture, animal nutrition, food and beverages, nutraceuticals, cosmetics and hygiene, medicine, agrochemistry, energy production and environment: A review". Environmental Chemistry Letters 18: 1451–76. doi:10.1007/s10311-020-01029-2. 
  3. ↑ 3.0 3.1 Namdar, D.; Mazuz, M.; Ion, A. et al. (2018). "Variation in the compositions of cannabinoid and terpenoids in Cannabis sativa derived from inflorescence position along the stem and extraction methods". Industrial Crops and Products 113: 376–82. doi:10.1016/j.indcrop.2018.01.060. 
  4. ↑ Turner, J.C.; Hemphill, J.K.; Mahlberg, P.G. (1978). "Quantitative Determination of Cannabinoids in Individual Glandular Trichomes of Cannabis sativa L. (Cannabaceae)". American Journal of Botany 65 (10): 1103–6. doi:10.1002/j.1537-2197.1978.tb06177.x. 
  5. ↑ Hanuš, L.O.; Meyer, S.M.; Muñoz, E. et al. (2016). "Phytocannabinoids: A unified critical inventory". Natural Product Reports 33: 1357–92. doi:10.1039/C6NP00074F. 
  6. ↑ Bertoli, A.; Tozzi, S.; Pistelli, L. et al. (2010). "Fibre hemp inflorescences: From crop-residues to essential oil production". Industrial Crops and Products 32 (3): 329–37. doi:10.1016/j.indcrop.2010.05.012. 
  7. ↑ 7.0 7.1 Andre, C.M.; Hausman, J.-F.; Guerriero, G. (2016). "Cannabis sativa: The plant of the thousand and one molecules". Frontiers in Plant Medicine 7: 19. doi:10.3389/fpls.2016.00019. PMC PMC4740396. PMID 26870049. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=PMC4740396. 
  8. ↑ Russo, E.B. (2011). "Taming THC: potential cannabis synergy and phytocannabinoid-terpenoid entourage effects". British Journal of Pharmacology 163 (7): 1344–64. doi:10.1111/j.1476-5381.2011.01238.x. 
  9. ↑ da Silva, A.C.R.; Lopes, P.M.; de Azevedo, M.M.B. et al. (2012). "Biological Activities of a-Pinene and β-Pinene Enantiomers". Molecules 17 (6): 6305-6316. doi:10.3390/molecules17066305. 
  10. ↑ Appendino, G.; Gibbons, S.; Giana, A. et al. (2008). "Antibacterial Cannabinoids from Cannabis sativa: A Structure−Activity Study". Journal of Natural Products 71 (8): 1427–30. doi:10.1021/np8002673. 
  11. ↑ Small, E.; Beckstead, H.D. (1973). "Common cannabinoid phenotypes in 350 stocks of Cannabis". Lloydia 36 (2): 144–65. PMID 4744553. 
  12. ↑ Fournier, G.; Richez-Dumanois, C.; Duvezin, J. et al. (1987). "Identification of a new chemotype in Cannabis sativa: cannabigerol-dominant plants, biogenetic and agronomic prospects". Planta Medica 53 (3): 277–80. doi:10.1055/s-2006-962705. PMID 3628560. 
  13. ↑ Pollio, A. (2016). "The Name of Cannabis: A Short Guide for Nonbotanists". Cannabis and Cannabinoid Research 1 (1): 234-238. doi:10.1089/can.2016.0027. PMC PMC5531363. PMID 28861494. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=PMC5531363. 
  14. ↑ Schilling, S.; Melzer, R.; McCabe, P.F. (2020). "Cannabis sativa". Current Biology 30 (1): R8–R9. doi:10.1016/j.cub.2019.10.039. PMID 31910378. 
  15. ↑ Sawler, J.; Stout, J.M.; Gardner, K.M. et al. (2015). "The Genetic Structure of Marijuana and Hemp". PLoS One 10 (8): e0133292. doi:10.1371/journal.pone.0133292. PMC PMC4550350. PMID 26308334. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=PMC4550350. 
  16. ↑ Janatová, A.; Fraňková, A.; Tlustoš, P. et al. (2018). "Yield and cannabinoids contents in different cannabis (Cannabis sativa L.) genotypes for medical use". Industrial Crops and Products 112: 363–67. doi:10.1016/j.indcrop.2017.12.006. 
  17. ↑ Aguilar, S.; Gutiérrez, V.; Sánchez, L. et al. (23 April 2018). "Medicinal cannabis policies and practices around the world". International Drug Policy Consortium. https://idpc.net/publications/2018/04/medicinal-cannabis-policies-and-practices-around-the-world. Retrieved 19 April 2021. 

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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