Difference between revisions of "Journal:Methods for quantification of cannabinoids: A narrative review"

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==Introduction==
==Introduction==
''[[Cannabis sativa]]'' L. is an annual herbaceous flowering plant indigenous to eastern Asia.<ref name="DeBackerInnov09">{{cite journal |title=Innovative development and validation of an HPLC/DAD method for the qualitative and quantitative determination of major cannabinoids in cannabis plant material |journal=Journal of Chromatography B |author=De Backer, B.; Debrus, B.; Lebrun, P. et al. |volume=877 |issue=32 |pages=4115–24 |year=2009 |doi=10.1016/j.jchromb.2009.11.004 |pmid=19932642}}</ref> The [[phenotype]]s of ''Cannabis'' are highly variable, and the plant is accepted to have two subspecies: ''C. sativa'' and ''[[Cannabis indica|C. indica]]''.<ref name="HilligAChemo04">{{cite journal |title=A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae) |journal=American Journal of Botany |author=Hillig, K.W.; Mahlberg, P.G. |volume=91 |issue=6 |pages=966-75 |year=2004 |doi=10.3732/ajb.91.6.966 |pmid=21653452}}</ref><ref name="KnightTheResults10">{{cite journal |title=The results of an experimental indoor hydroponic Cannabis growing study, using the 'Screen of Green' (ScrOG) method-Yield, tetrahydrocannabinol (THC) and DNA analysis |journal=Forensic Science International |author=Knight, G.; Hansen, S.; Connor, M. et al. |volume=202 |issue=1–3 |pages=36–44 |year=2010 |doi=10.1016/j.forsciint.2010.04.022 |pmid=20462712}}</ref> A third variety, ''[[Cannabis ruderalis|C. ruderalis]]'', has been identified as a ''Cannabis'' species; however, it is not broadly recognized as a specific subspecies of ''C. sativa''.<ref name="HilligAChemo04" /><ref name="FischedickCanna10">{{cite journal |title=Cannabinoid receptor 1 binding activity and quantitative analysis of ''Cannabis sativa'' L. smoke and vapor |journal=Chemical & Pharmaceutical Bulletin |author=Fischedick, J.T.; Van Der Kooy, F.; Verpoorte, R. |volume=58 |issue=2 |pages=201–7 |year=2010 |doi=10.1248/cpb.58.201 |pmid=20118579}}</ref> The ''Cannabis'' plant has been used for its therapeutic properties for thousands of years, and it was introduced to Western medicine in the nineteenth century, until it was later outlawed in the U.S. from the mid-1930s.<ref name="Aizpurua-OlaizolaIdent14">{{cite journal |title=Identification and quantification of cannabinoids in ''Cannabis sativa'' L. plants by high performance liquid chromatography-mass spectrometry |journal=Analytical and Bioanalytical Chemistry |author=Aizpurua-Olaizola, O.; Omar, J.; Navarro, P. et al. |volume=406 |issue=29 |pages=7549-60 |year=2014 |doi=10.1007/s00216-014-8177-x |pmid=25338935}}</ref>
''[[Cannabis sativa]]'' L. is an annual herbaceous flowering plant indigenous to eastern Asia.<ref name="DeBackerInnov09">{{cite journal |title=Innovative development and validation of an HPLC/DAD method for the qualitative and quantitative determination of major cannabinoids in cannabis plant material |journal=Journal of Chromatography B |author=De Backer, B.; Debrus, B.; Lebrun, P. et al. |volume=877 |issue=32 |pages=4115–24 |year=2009 |doi=10.1016/j.jchromb.2009.11.004 |pmid=19932642}}</ref> The [[phenotype]]s of ''[[Cannabis]]'' are highly variable, and the plant is accepted to have two subspecies: ''C. sativa'' and ''[[Cannabis indica|C. indica]]''.<ref name="HilligAChemo04">{{cite journal |title=A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae) |journal=American Journal of Botany |author=Hillig, K.W.; Mahlberg, P.G. |volume=91 |issue=6 |pages=966-75 |year=2004 |doi=10.3732/ajb.91.6.966 |pmid=21653452}}</ref><ref name="KnightTheResults10">{{cite journal |title=The results of an experimental indoor hydroponic Cannabis growing study, using the 'Screen of Green' (ScrOG) method-Yield, tetrahydrocannabinol (THC) and DNA analysis |journal=Forensic Science International |author=Knight, G.; Hansen, S.; Connor, M. et al. |volume=202 |issue=1–3 |pages=36–44 |year=2010 |doi=10.1016/j.forsciint.2010.04.022 |pmid=20462712}}</ref> A third variety, ''[[Cannabis ruderalis|C. ruderalis]]'', has been identified as a ''Cannabis'' species; however, it is not broadly recognized as a specific subspecies of ''C. sativa''.<ref name="HilligAChemo04" /><ref name="FischedickCanna10">{{cite journal |title=Cannabinoid receptor 1 binding activity and quantitative analysis of ''Cannabis sativa'' L. smoke and vapor |journal=Chemical & Pharmaceutical Bulletin |author=Fischedick, J.T.; Van Der Kooy, F.; Verpoorte, R. |volume=58 |issue=2 |pages=201–7 |year=2010 |doi=10.1248/cpb.58.201 |pmid=20118579}}</ref> The ''Cannabis'' plant has been used for its therapeutic properties for thousands of years, and it was introduced to Western medicine in the nineteenth century, until it was later outlawed in the U.S. from the mid-1930s.<ref name="Aizpurua-OlaizolaIdent14">{{cite journal |title=Identification and quantification of cannabinoids in ''Cannabis sativa'' L. plants by high performance liquid chromatography-mass spectrometry |journal=Analytical and Bioanalytical Chemistry |author=Aizpurua-Olaizola, O.; Omar, J.; Navarro, P. et al. |volume=406 |issue=29 |pages=7549-60 |year=2014 |doi=10.1007/s00216-014-8177-x |pmid=25338935}}</ref>
 


The medicinal compounds from ''Cannabis'' plants are mostly concentrated in the female flowers of this dioecious species.<ref name="FischedickCanna10" /> The so-called [[resin]] is the source of a wide variety of [[terpenoid]]s and [[cannabinoid]]s.<ref name="FischedickCanna10" /> The [[Cannabis (drug)|therapeutic properties of cannabis]] are attributed to cannabinoids.<ref name="HazekampQuant04">{{cite journal |title=Quantitative analysis of cannabinoids from Cannabis sativa using 1H-NMR |journal=Chemical and Pharmaceutical Bulletin |author=Hazekamp, A.; Choi Y.H.; Verpoorte, R. |volume=52 |issue=6 |pages=718–21 |year=2004 |doi=10.1248/cpb.52.718 |pmid=15187394}}</ref> Cannabinoids are found in the resin produced by the [[trichome]]s, which are widely distributed on both the male and female plants, though they are most highly concentrated on the female flowers of the cannabis plant.<ref name="DeBackerInnov09" /><ref name="CittiPharm18">{{cite journal |title=Pharmaceutical and biomedical analysis of cannabinoids: A critical review |journal=Journal of Pharmaceutical and Biomedical Analysis |author=Citti, C.; Braghiroli, D.; Vandelli, M.A. et al. |volume=147 |pages=565–79 |year=2018 |doi=10.1016/j.jpba.2017.06.003 |pmid=28641906}}</ref> Cannabinoids are [[Meroterpen#Terpenophenolics|terpenophenolic]] compounds unique to ''Cannabis''.<ref name="HilligAChemo04" /> To date, 144 cannabinoids have been identified.<ref name="HazekampQuant04" /> The two cannabinoids most well known for their therapeutic properties are [[tetrahydrocannabinol]] (THC) and [[cannabidiol]] (CBD).<ref name="HilligAChemo04" /><ref name="Aizpurua-OlaizolaEvol16">{{cite journal |title=Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes |journal=Journal of Natural Products |author=Aizpurua-Olaizola, O.; Soydaner, U.; Öztürk, E. et al. |volume=79 |issue=2 |pages=324-31 |year=2016 |doi=10.1021/acs.jnatprod.5b00949 |pmid=26836472}}</ref> THC and CBD are the neutral homologs of [[tetrahydrocannabinolic acid]] (THCA) and [[cannabidiolic acid]] (CBDA), respectively.<ref name="Aizpurua-OlaizolaEvol16" /> A conventional classification model of cannabinoids is due to their chemical contents dividing them into eleven subclasses, including THC, CBD, [[cannabigerol]] (CBG), [[cannabichromene]] (CBC), [[cannabinol]] (CBN), (−)-Δ8-trans-tetrahydrocannabinol (Δ8-THC), cannabicyclol (CBL), [[cannabinodiol]] (CBND), cannabielsoin (CBE), cannabitriol (CBT) and "miscellaneous types."<ref name="BermanANew18">{{cite journal |title=A new ESI-LC/MS approach for comprehensive metabolic profiling of phytocannabinoids in Cannabis |journal=Scientific Reports |author=Berman, P.; Futoran, K.; Lewitus, G.M. et al. |volume=8 |issue=1 |at=14280 |year=2018 |doi=10.1038/s41598-018-32651-4 |pmid=30250104 |pmc=PMC6155167}}</ref> (Fig. 1).




Revision as of 18:13, 30 November 2020

Full article title Methods for quantification of cannabinoids: A narrative review
Journal Journal of Cannabis Research
Author(s) Lazarjani, Masoumeh P.; Torres, Stephanie; Hooker, Thom; Fowlie, Chris; Young, Owen; Seyfoddin, Ali
Author affiliation(s) Auckland University of Technology, Chapman University, ZeaCann Limited,
Primary contact Email: Online form
Year published 2020
Volume and issue 2
Article # 35
DOI 10.1186/s42238-020-00040-2
ISSN 2522-5782
Distribution license Creative Commons Attribution 4.0 International
Website https://jcannabisresearch.biomedcentral.com/articles/10.1186/s42238-020-00040-2
Download https://jcannabisresearch.biomedcentral.com/track/pdf/10.1186/s42238-020-00040-2.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

Background: Around 144 cannabinoids have been identified in the Cannabis plant; among them tetrahydrocannabinol (THC) and cannabidiol (CBD) are the most prominent ones. Because of the legal restrictions on cannabis in many countries, it is difficult to obtain standards to use in research; nonetheless, it is important to develop a cannabinoid quantification technique, with practical pharmaceutical applications for quality control of future therapeutic cannabinoids.

Method: To find relevant articles for this narrative review paper, a combination of keywords such as "medicinal cannabis," "analytical," "quantification," and "cannabinoids" were searched for in PubMed, EMBASE, MEDLINE, Google Scholar, and Cochrane Library (Wiley) databases.

Results: The most common cannabinoid quantification techniques include gas chromatography (GC) and high-performance liquid chromatography (HPLC). Gas chromatography is often used in conjunction with mass spectrometry (MS) or flame ionization detection (FID). The major advantage of GC is with the quantification of terpenes. However, for evaluating acidic cannabinoids, it needs to be derivatized. The main advantage of HPLC is the ability to quantify both acidic and neutral forms of cannabinoids without derivatization, which is often accomplished with MS or ultraviolet (UV) detectors.

Conclusion: Based on the information presented in this review, the ideal cannabinoid quantification method is HPLC paired with tandem mass spectrometry (MS/MS).

Introduction

Cannabis sativa L. is an annual herbaceous flowering plant indigenous to eastern Asia.[1] The phenotypes of Cannabis are highly variable, and the plant is accepted to have two subspecies: C. sativa and C. indica.[2][3] A third variety, C. ruderalis, has been identified as a Cannabis species; however, it is not broadly recognized as a specific subspecies of C. sativa.[2][4] The Cannabis plant has been used for its therapeutic properties for thousands of years, and it was introduced to Western medicine in the nineteenth century, until it was later outlawed in the U.S. from the mid-1930s.[5]

The medicinal compounds from Cannabis plants are mostly concentrated in the female flowers of this dioecious species.[4] The so-called resin is the source of a wide variety of terpenoids and cannabinoids.[4] The therapeutic properties of cannabis are attributed to cannabinoids.[6] Cannabinoids are found in the resin produced by the trichomes, which are widely distributed on both the male and female plants, though they are most highly concentrated on the female flowers of the cannabis plant.[1][7] Cannabinoids are terpenophenolic compounds unique to Cannabis.[2] To date, 144 cannabinoids have been identified.[6] The two cannabinoids most well known for their therapeutic properties are tetrahydrocannabinol (THC) and cannabidiol (CBD).[2][8] THC and CBD are the neutral homologs of tetrahydrocannabinolic acid (THCA) and cannabidiolic acid (CBDA), respectively.[8] A conventional classification model of cannabinoids is due to their chemical contents dividing them into eleven subclasses, including THC, CBD, cannabigerol (CBG), cannabichromene (CBC), cannabinol (CBN), (−)-Δ8-trans-tetrahydrocannabinol (Δ8-THC), cannabicyclol (CBL), cannabinodiol (CBND), cannabielsoin (CBE), cannabitriol (CBT) and "miscellaneous types."[9] (Fig. 1).


[10]

References

  1. ↑ 1.0 1.1 De Backer, B.; Debrus, B.; Lebrun, P. et al. (2009). "Innovative development and validation of an HPLC/DAD method for the qualitative and quantitative determination of major cannabinoids in cannabis plant material". Journal of Chromatography B 877 (32): 4115–24. doi:10.1016/j.jchromb.2009.11.004. PMID 19932642. 
  2. ↑ 2.0 2.1 2.2 2.3 Hillig, K.W.; Mahlberg, P.G. (2004). "A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae)". American Journal of Botany 91 (6): 966-75. doi:10.3732/ajb.91.6.966. PMID 21653452. 
  3. ↑ Knight, G.; Hansen, S.; Connor, M. et al. (2010). "The results of an experimental indoor hydroponic Cannabis growing study, using the 'Screen of Green' (ScrOG) method-Yield, tetrahydrocannabinol (THC) and DNA analysis". Forensic Science International 202 (1–3): 36–44. doi:10.1016/j.forsciint.2010.04.022. PMID 20462712. 
  4. ↑ 4.0 4.1 4.2 Fischedick, J.T.; Van Der Kooy, F.; Verpoorte, R. (2010). "Cannabinoid receptor 1 binding activity and quantitative analysis of Cannabis sativa L. smoke and vapor". Chemical & Pharmaceutical Bulletin 58 (2): 201–7. doi:10.1248/cpb.58.201. PMID 20118579. 
  5. ↑ Aizpurua-Olaizola, O.; Omar, J.; Navarro, P. et al. (2014). "Identification and quantification of cannabinoids in Cannabis sativa L. plants by high performance liquid chromatography-mass spectrometry". Analytical and Bioanalytical Chemistry 406 (29): 7549-60. doi:10.1007/s00216-014-8177-x. PMID 25338935. 
  6. ↑ 6.0 6.1 Hazekamp, A.; Choi Y.H.; Verpoorte, R. (2004). "Quantitative analysis of cannabinoids from Cannabis sativa using 1H-NMR". Chemical and Pharmaceutical Bulletin 52 (6): 718–21. doi:10.1248/cpb.52.718. PMID 15187394. 
  7. ↑ Citti, C.; Braghiroli, D.; Vandelli, M.A. et al. (2018). "Pharmaceutical and biomedical analysis of cannabinoids: A critical review". Journal of Pharmaceutical and Biomedical Analysis 147: 565–79. doi:10.1016/j.jpba.2017.06.003. PMID 28641906. 
  8. ↑ 8.0 8.1 Aizpurua-Olaizola, O.; Soydaner, U.; Öztürk, E. et al. (2016). "Evolution of the Cannabinoid and Terpene Content during the Growth of Cannabis sativa Plants from Different Chemotypes". Journal of Natural Products 79 (2): 324-31. doi:10.1021/acs.jnatprod.5b00949. PMID 26836472. 
  9. ↑ Berman, P.; Futoran, K.; Lewitus, G.M. et al. (2018). "A new ESI-LC/MS approach for comprehensive metabolic profiling of phytocannabinoids in Cannabis". Scientific Reports 8 (1): 14280. doi:10.1038/s41598-018-32651-4. PMC PMC6155167. PMID 30250104. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=PMC6155167. 
  10. ↑ Fischedick, J.T.; Hazekamp, A.; Erkelens, T. et al. (2010). "Metabolic fingerprinting of Cannabis sativa L., cannabinoids and terpenoids for chemotaxonomic and drug standardization purposes". Phytochemistry 71 (17–18): 2058–73. doi:10.1016/j.phytochem.2010.10.001. PMID 21040939. 

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 article lists references in alphabetical order; this wiki organizes them by order of appearance, by design.

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