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''[[wikipedia:Cannabis|Cannabis]]'' is a genus of annual [[wikipedia:Dioecy|dioecious]] plants within the family [[wikipedia:Cannabaceae|Cannabaceae]] with a rich and complex constituency of pharmacologically relevant [[wikipedia:Phytochemical|phytochemicals]].<ref name="RussoTheCase19">{{cite journal |title=The Case for the Entourage Effect and Conventional Breeding of Clinical Cannabis: No "Strain," No Gain |journal=Frontiers in Plant Science |author=Russo, E.B. |volume=9 |at=1969 |year=2019 |doi=10.3389/fpls.2018.01969 |pmid=30687364 |pmc=PMC6334252}}</ref><ref name="RussoHistory07">{{cite journal |title=History of cannabis and its preparations in saga, science, and sobriquet |journal=Chemistry & Biodiversity |author=Russo, E.B. |volume=4 |issue=8 |pages=1614-48 |year=2007 |doi=10.1002/cbdv.200790144 |pmid=17712811}}</ref> Under the [[wikipedia:Single Convention on Narcotic Drugs|Single Convention on Narcotic Drugs]] (1961), cannabis was deemed to be a plant without medicinal purpose, a conclusion based on very little scientific evidence or clinical trial data.<ref name="WrightCanna17">{{cite web |url=https://www.everblucapital.com/wp-content/uploads/2017/11/EverBlu-Research-Cannabis-Industry-Report.pdf |format=PDF |title=Cannabis Industry Report |author=Wright, R. |publisher=EverBlu Capital |date=24 November 2017 |accessdate=12 January 2019}}</ref> As a result, [[wikipedia:Medical cannabis|medicinal use of cannabis]] was practically prohibited by its status as an illegal narcotic worldwide, and research into cannabis chemistry and biology was largely limited to law enforcement and [[Forensic science|forensics]] applications.<ref name="WhitingCanna15">{{cite journal |title=Cannabinoids for Medical Use: A Systematic Review and Meta-analysis |journal=JAMA |author=Whiting, P.F.; Wolff, R.F.; Deshpande, S. et al. |volume=313 |issue=24 |pages=2456–73 |year=2015 |doi=10.1001/jama.2015.6358 |pmid=26103030}}</ref> Changes in the attitudes towards cannabis across various societies and increasing evidence for the benefits of [[wikipedia:Cannabinoid|cannabinoids]] in the treatment of otherwise intractable conditions have precipitated recent changes to legislature in a number of jurisdictions, including Australia.<ref name="WrightCanna17" /> Interest in the medicinal uses of cannabis is increasing, as indicated by a growing number of review articles on the topic.<ref name="KlumpersABrief19">{{cite journal |title=A Brief Background on Cannabis: From Plant to Medical Indications |journal=Journal of AOAC International |author=Klumpers, L.E.; Thacker, D.L. |volume=102 |issue=2 |pages=412–20 |year=2019 |doi=10.5740/jaoacint.18-0208 |pmid=30139415}}</ref><ref name="BoothTerpenes19">{{cite journal |title=Terpenes in Cannabis sativa - From plant genome to humans |journal=Plant Science |author=Booth, J.K.; Bohlmann, J. |volume=284 |pages=67–72 |year=2019 |doi=10.1016/j.plantsci.2019.03.022 |pmid=31084880}}</ref><ref name="PamplonaPotent18">{{cite journal |title=Potential Clinical Benefits of CBD-Rich Cannabis Extracts Over Purified CBD in Treatment-Resistant Epilepsy: Observational Data Meta-analysis |journal=Frontiers in Neurology |author=Pamplona, F.A.; da Silva, L.R.; Coan, A.C. |volume=9 |pages=759 |year=2018 |doi=10.3389/fneur.2018.00759 |pmid=30258398 |pmc=PMC6143706}}</ref><ref name="BoniniCanna18">{{cite journal |title=Cannabis sativa: A comprehensive ethnopharmacological review of a medicinal plant with a long history |journal=Journal of Ethnopharmacology |author=Bonini, S.A.; Premoli, M.; Tambaro, S. et al. |volume=227 |pages=300–15 |year=2018 |doi=10.1016/j.jep.2018.09.004 |pmid=30205181}}</ref>
''[[wikipedia:Cannabis|Cannabis]]'' is a genus of annual [[wikipedia:Dioecy|dioecious]] plants within the family [[wikipedia:Cannabaceae|Cannabaceae]] with a rich and complex constituency of pharmacologically relevant [[wikipedia:Phytochemical|phytochemicals]].<ref name="RussoTheCase19">{{cite journal |title=The Case for the Entourage Effect and Conventional Breeding of Clinical Cannabis: No "Strain," No Gain |journal=Frontiers in Plant Science |author=Russo, E.B. |volume=9 |at=1969 |year=2019 |doi=10.3389/fpls.2018.01969 |pmid=30687364 |pmc=PMC6334252}}</ref><ref name="RussoHistory07">{{cite journal |title=History of cannabis and its preparations in saga, science, and sobriquet |journal=Chemistry & Biodiversity |author=Russo, E.B. |volume=4 |issue=8 |pages=1614-48 |year=2007 |doi=10.1002/cbdv.200790144 |pmid=17712811}}</ref> Under the [[wikipedia:Single Convention on Narcotic Drugs|Single Convention on Narcotic Drugs]] (1961), cannabis was deemed to be a plant without medicinal purpose, a conclusion based on very little scientific evidence or clinical trial data.<ref name="WrightCanna17">{{cite web |url=https://www.everblucapital.com/wp-content/uploads/2017/11/EverBlu-Research-Cannabis-Industry-Report.pdf |format=PDF |title=Cannabis Industry Report |author=Wright, R. |publisher=EverBlu Capital |date=24 November 2017 |accessdate=12 January 2019}}</ref> As a result, [[wikipedia:Medical cannabis|medicinal use of cannabis]] was practically prohibited by its status as an illegal narcotic worldwide, and research into cannabis chemistry and biology was largely limited to law enforcement and [[Forensic science|forensics]] applications.<ref name="WhitingCanna15">{{cite journal |title=Cannabinoids for Medical Use: A Systematic Review and Meta-analysis |journal=JAMA |author=Whiting, P.F.; Wolff, R.F.; Deshpande, S. et al. |volume=313 |issue=24 |pages=2456–73 |year=2015 |doi=10.1001/jama.2015.6358 |pmid=26103030}}</ref> Changes in the attitudes towards cannabis across various societies and increasing evidence for the benefits of [[wikipedia:Cannabinoid|cannabinoids]] in the treatment of otherwise intractable conditions have precipitated recent changes to legislature in a number of jurisdictions, including Australia.<ref name="WrightCanna17" /> Interest in the medicinal uses of cannabis is increasing, as indicated by a growing number of review articles on the topic.<ref name="KlumpersABrief19">{{cite journal |title=A Brief Background on Cannabis: From Plant to Medical Indications |journal=Journal of AOAC International |author=Klumpers, L.E.; Thacker, D.L. |volume=102 |issue=2 |pages=412–20 |year=2019 |doi=10.5740/jaoacint.18-0208 |pmid=30139415}}</ref><ref name="BoothTerpenes19">{{cite journal |title=Terpenes in Cannabis sativa - From plant genome to humans |journal=Plant Science |author=Booth, J.K.; Bohlmann, J. |volume=284 |pages=67–72 |year=2019 |doi=10.1016/j.plantsci.2019.03.022 |pmid=31084880}}</ref><ref name="PamplonaPotent18">{{cite journal |title=Potential Clinical Benefits of CBD-Rich Cannabis Extracts Over Purified CBD in Treatment-Resistant Epilepsy: Observational Data Meta-analysis |journal=Frontiers in Neurology |author=Pamplona, F.A.; da Silva, L.R.; Coan, A.C. |volume=9 |pages=759 |year=2018 |doi=10.3389/fneur.2018.00759 |pmid=30258398 |pmc=PMC6143706}}</ref><ref name="BoniniCanna18">{{cite journal |title=Cannabis sativa: A comprehensive ethnopharmacological review of a medicinal plant with a long history |journal=Journal of Ethnopharmacology |author=Bonini, S.A.; Premoli, M.; Tambaro, S. et al. |volume=227 |pages=300–15 |year=2018 |doi=10.1016/j.jep.2018.09.004 |pmid=30205181}}</ref>


 
Cannabis, cannabis extracts, and purified (to varying degrees) major cannabinoids such as [[wikipedia:Tetrahydrocannabinol|Δ9-tetrahydrocannabinol]] (THC) and [[wikipedia:Cannabidiol|cannabidiol]] (CBD) are now being used for the treatment of intractable and debilitating illnesses, such as Dravet’s Syndrome, and investigated for a range of others.<ref name="KlumpersABrief19" /><ref name="PamplonaPotent18" /><ref name="Weston-GreenTheUnited19">{{cite book |chapter=The United Chemicals of Cannabis: Beneficial Effects of Cannabis Phytochemicals on the Brain and Cognition |title=Recent Advances in Cannabinoid Research |author=Weston-Green, K. |editor=Costain, W.J.; Laprarie, R.B. |publisher=IntechOpen |year=2019 |isbn=9781838806415 |doi=10.5772/intechopen.79266}}</ref><ref name="BaronMedicinal18">{{cite journal |title=Medicinal Properties of Cannabinoids, Terpenes, and Flavonoids in Cannabis, and Benefits in Migraine, Headache, and Pain: An Update on Current Evidence and Cannabis Science |journal=Headache |author=Baron, E.P. |volume=58 |issue=7 |pages=1139–86 |year=2018 |doi=10.1111/head.13345 |pmid=30152161}}</ref><ref name="RohlederCanna16">{{cite journal |title=Cannabidiol as a Potential New Type of an Antipsychotic. A Critical Review of the Evidence |journal=Frontiers in Pharmacology |author=Rohleder, C.; Müller, J.K.; Lange, B. et al. |volume=7 |at=422 |year=2016 |doi=10.3389/fphar.2016.00422 |pmid=27877130 |pmc=PMC5099166}}</ref><ref name="Bonn-MillerCanna18">{{cite journal |title=Cannabis and cannabinoid drug development: evaluating botanical versus single molecule approaches |journal=International Review of Psychiatry |author=Bonn-Miller, M.O.; ElSohly, M.A.; Loflin, M.J.E. et al. |volume=30 |issue=3 |pages=277–84 |year=2018 |doi=10.1080/09540261.2018.1474730 |pmid=30179534 |pmc=PMC6242809}}</ref> When administered as medicinal cannabis extracts, that is, along with the remaining portion of other cannabinoids and non-cannabinoid phytochemicals, less than a quarter of the equivalent dose of purified CBD is required, and markedly lower side effects are commonly observed.<ref name="PamplonaPotent18" /> This is in-line with a long line of anecdotal evidence that complex plant-based medicines are more effective than their isolated “actives,” which has given rise to the concept of the “[[wikipedia:Entourage effect|entourage effect]],” the modulating or synergistic effects of phytochemical compounds such as the minor cannabinoids on those effects related to THC.<ref name="Ben-ShabatEnEnt98">{{cite journal |title=An entourage effect: Inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity |journal=European Journal of Pharmacology |author=Ben-Shabat, S.; Fride, E.; Sheskin, T. et al. |volume=353 |issue=1 |pages=23–31 |year=1998 |doi=10.1016/s0014-2999(98)00392-6 |pmid=9721036}}</ref><ref name="MechoulamFrom99">{{cite journal |title=From gan-zi-gun-nu to anandamide and 2-arachidonoylglycerol: The ongoing story of cannabis |journal=Natural Product Reports |author=Mechoulam, R.; Ben-Shabat, S. |volume=16 |issue=2 |pages=131–43 |year=1999 |doi=10.1039/a703973e |pmid=10331283}}</ref><ref name="McPartlandCanna08">{{cite journal |title=Cannabis and Cannabis Extracts: Greater Than the Sum of Their Parts? |journal=Journal of Cannabis Therapeutics |author=McPartland, J.M.; Russo, E.B. |volume=1 |issue=3–4 |pages=103–32 |year=2001 |doi=10.1300/J175v01n03_08}}</ref> Despite a current lack of understanding for the underlying mechanisms<ref name="SantiagoAbsence19">{{cite journal |title=Absence of Entourage: Terpenoids Commonly Found in Cannabis sativa Do Not Modulate the Functional Activity of Δ 9-THC at Human CB 1 and CB 2 Receptors |journal=Cannabis and Cannabinoid Research |author=Santiago, M.; Sachdev, S.; Arnold, J.C. etc. |volume=4 |issue=3 |pages=165-176 |year=2019 |doi=10.1089/can.2019.0016 |pmid=31559333 |pmc=PMC6757242}}</ref>, the concept is increasingly applied to non-cannabinoid cannabis phytochemicals, such as [[wikipedia:Terpene|terpenes]] and [[wikipedia:Terpenoid|terpenoids]].<ref name="BoothTerpenes19" /><ref name="Weston-GreenTheUnited19" /><ref name="BaronMedicinal18" /><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 |pmid=21749363 |pmc=PMC3165946}}</ref>




Revision as of 21:57, 27 July 2020

Full article title A high-throughput method for the comprehensive analysis of terpenes and terpenoids in medicinal cannabis biomass
Journal Metabolites
Author(s) Krill, Christian; Rochfort, Simone; Spangenberg, German
Author affiliation(s) AgriBio, the Centre For AgriBioscience
Primary contact Email: christian dot krill at agriculture dot vic dot gov dot au
Year published 2020
Volume and issue 10(7)
Article # 276
DOI 10.3390/metabo10070276
ISSN 2218-1989
Distribution license Creative Commons Attribution 4.0 International
Website https://www.mdpi.com/2218-1989/10/7/276/htm
Download https://www.mdpi.com/2218-1989/10/7/276/pdf (PDF)
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Abstract

Cannabis and its secondary metabolite content have recently seen a surge in research interest. Cannabis terpenes and terpenoids in particular are increasingly the focus of research efforts due to the possibility of their contribution to the overall therapeutic effect of medicinal cannabis. Current methodology to quantify terpenes in cannabis biomass mostly relies on large quantities of biomass, long extraction protocols, and long gas chromatography (GC) gradient times, often exceeding 60 minutes. They are therefore not easily applicable in the high-throughput environment of a cannabis breeding program. The method presented here, however, is based on a simple hexane extract from 40 mg of biomass, with 50 μg/mL dodecane as internal standard, and a gradient of less than 30 minutes. The method can detect 48 individual terpenes and terpenoids and was validated for selectivity, linearity, limit of detection/limit of quantitation (LOD/LOQ), precision, intermediate precision, and accuracy (recovery) for 22 terpenes and terpenoids. The validation parameters are comparable to previously published studies that employ significantly longer runtimes and/or more complex extraction protocols. It is currently being applied to medicinal cannabis precision breeding programs.

Keywords: cannabis volatiles, terpenes, terpenoids, profiling, high-throughput method

Introduction

Cannabis is a genus of annual dioecious plants within the family Cannabaceae with a rich and complex constituency of pharmacologically relevant phytochemicals.[1][2] Under the Single Convention on Narcotic Drugs (1961), cannabis was deemed to be a plant without medicinal purpose, a conclusion based on very little scientific evidence or clinical trial data.[3] As a result, medicinal use of cannabis was practically prohibited by its status as an illegal narcotic worldwide, and research into cannabis chemistry and biology was largely limited to law enforcement and forensics applications.[4] Changes in the attitudes towards cannabis across various societies and increasing evidence for the benefits of cannabinoids in the treatment of otherwise intractable conditions have precipitated recent changes to legislature in a number of jurisdictions, including Australia.[3] Interest in the medicinal uses of cannabis is increasing, as indicated by a growing number of review articles on the topic.[5][6][7][8]

Cannabis, cannabis extracts, and purified (to varying degrees) major cannabinoids such as Δ9-tetrahydrocannabinol (THC) and cannabidiol (CBD) are now being used for the treatment of intractable and debilitating illnesses, such as Dravet’s Syndrome, and investigated for a range of others.[5][7][9][10][11][12] When administered as medicinal cannabis extracts, that is, along with the remaining portion of other cannabinoids and non-cannabinoid phytochemicals, less than a quarter of the equivalent dose of purified CBD is required, and markedly lower side effects are commonly observed.[7] This is in-line with a long line of anecdotal evidence that complex plant-based medicines are more effective than their isolated “actives,” which has given rise to the concept of the “entourage effect,” the modulating or synergistic effects of phytochemical compounds such as the minor cannabinoids on those effects related to THC.[13][14][15] Despite a current lack of understanding for the underlying mechanisms[16], the concept is increasingly applied to non-cannabinoid cannabis phytochemicals, such as terpenes and terpenoids.[6][9][10][17]


References

  1. ↑ Russo, E.B. (2019). "The Case for the Entourage Effect and Conventional Breeding of Clinical Cannabis: No "Strain," No Gain". Frontiers in Plant Science 9: 1969. doi:10.3389/fpls.2018.01969. PMC PMC6334252. PMID 30687364. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6334252. 
  2. ↑ Russo, E.B. (2007). "History of cannabis and its preparations in saga, science, and sobriquet". Chemistry & Biodiversity 4 (8): 1614-48. doi:10.1002/cbdv.200790144. PMID 17712811. 
  3. ↑ 3.0 3.1 Wright, R. (24 November 2017). "Cannabis Industry Report" (PDF). EverBlu Capital. https://www.everblucapital.com/wp-content/uploads/2017/11/EverBlu-Research-Cannabis-Industry-Report.pdf. Retrieved 12 January 2019. 
  4. ↑ Whiting, P.F.; Wolff, R.F.; Deshpande, S. et al. (2015). "Cannabinoids for Medical Use: A Systematic Review and Meta-analysis". JAMA 313 (24): 2456–73. doi:10.1001/jama.2015.6358. PMID 26103030. 
  5. ↑ 5.0 5.1 Klumpers, L.E.; Thacker, D.L. (2019). "A Brief Background on Cannabis: From Plant to Medical Indications". Journal of AOAC International 102 (2): 412–20. doi:10.5740/jaoacint.18-0208. PMID 30139415. 
  6. ↑ 6.0 6.1 Booth, J.K.; Bohlmann, J. (2019). "Terpenes in Cannabis sativa - From plant genome to humans". Plant Science 284: 67–72. doi:10.1016/j.plantsci.2019.03.022. PMID 31084880. 
  7. ↑ 7.0 7.1 7.2 Pamplona, F.A.; da Silva, L.R.; Coan, A.C. (2018). "Potential Clinical Benefits of CBD-Rich Cannabis Extracts Over Purified CBD in Treatment-Resistant Epilepsy: Observational Data Meta-analysis". Frontiers in Neurology 9: 759. doi:10.3389/fneur.2018.00759. PMC PMC6143706. PMID 30258398. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6143706. 
  8. ↑ Bonini, S.A.; Premoli, M.; Tambaro, S. et al. (2018). "Cannabis sativa: A comprehensive ethnopharmacological review of a medicinal plant with a long history". Journal of Ethnopharmacology 227: 300–15. doi:10.1016/j.jep.2018.09.004. PMID 30205181. 
  9. ↑ 9.0 9.1 Weston-Green, K. (2019). "The United Chemicals of Cannabis: Beneficial Effects of Cannabis Phytochemicals on the Brain and Cognition". In Costain, W.J.; Laprarie, R.B.. Recent Advances in Cannabinoid Research. IntechOpen. doi:10.5772/intechopen.79266. ISBN 9781838806415. 
  10. ↑ 10.0 10.1 Baron, E.P. (2018). "Medicinal Properties of Cannabinoids, Terpenes, and Flavonoids in Cannabis, and Benefits in Migraine, Headache, and Pain: An Update on Current Evidence and Cannabis Science". Headache 58 (7): 1139–86. doi:10.1111/head.13345. PMID 30152161. 
  11. ↑ Rohleder, C.; Müller, J.K.; Lange, B. et al. (2016). "Cannabidiol as a Potential New Type of an Antipsychotic. A Critical Review of the Evidence". Frontiers in Pharmacology 7: 422. doi:10.3389/fphar.2016.00422. PMC PMC5099166. PMID 27877130. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5099166. 
  12. ↑ Bonn-Miller, M.O.; ElSohly, M.A.; Loflin, M.J.E. et al. (2018). "Cannabis and cannabinoid drug development: evaluating botanical versus single molecule approaches". International Review of Psychiatry 30 (3): 277–84. doi:10.1080/09540261.2018.1474730. PMC PMC6242809. PMID 30179534. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6242809. 
  13. ↑ Ben-Shabat, S.; Fride, E.; Sheskin, T. et al. (1998). "An entourage effect: Inactive endogenous fatty acid glycerol esters enhance 2-arachidonoyl-glycerol cannabinoid activity". European Journal of Pharmacology 353 (1): 23–31. doi:10.1016/s0014-2999(98)00392-6. PMID 9721036. 
  14. ↑ Mechoulam, R.; Ben-Shabat, S. (1999). "From gan-zi-gun-nu to anandamide and 2-arachidonoylglycerol: The ongoing story of cannabis". Natural Product Reports 16 (2): 131–43. doi:10.1039/a703973e. PMID 10331283. 
  15. ↑ McPartland, J.M.; Russo, E.B. (2001). "Cannabis and Cannabis Extracts: Greater Than the Sum of Their Parts?". Journal of Cannabis Therapeutics 1 (3–4): 103–32. doi:10.1300/J175v01n03_08. 
  16. ↑ Santiago, M.; Sachdev, S.; Arnold, J.C. etc. (2019). "Absence of Entourage: Terpenoids Commonly Found in Cannabis sativa Do Not Modulate the Functional Activity of Δ 9-THC at Human CB 1 and CB 2 Receptors". Cannabis and Cannabinoid Research 4 (3): 165-176. doi:10.1089/can.2019.0016. PMC PMC6757242. PMID 31559333. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6757242. 
  17. ↑ 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. PMC PMC3165946. PMID 21749363. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3165946. 

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. The original includes an "in prep" citation at citation 8, but the citation appears to be about grapes and tobacco and not related to cannabis; it could not be verified as published and has been omitted for this version.

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