Acidic Cannabinoid Decarboxylation

Overview

Journal Cannabis Cannabinoid Res

Specialty Pharmacology

Date 2021 Sep 22

PMID 34550791

Citations 9

Authors

Crist N Filer

Affiliations

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Abstract

is a valuable plant, cultivated by humans for millennia. However, it has only been in the past several decades that biologists have begun to clarify the interesting biosynthesis details, especially the production of its fascinating natural products termed acidic cannabinoids. Acidic cannabinoids can experience a common organic chemistry reaction known as decarboxylation, transforming them into structural analogues referred to as neutral cannabinoids with far different pharmacology. This review addresses acidic and neutral cannabinoid structural pairs, when and where acidic cannabinoid decarboxylation occurs, the kinetics and mechanism of the decarboxylation reaction as well as possible future directions for this topic. Acidic cannabinoid decarboxylation is a unique transformation that has been increasingly investigated over the past several decades. Understanding how acidic cannabinoid decarboxylation occurs naturally as well as how it can be promoted or prevented during harvesting or storage is important for the various stakeholders in cultivation.

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References

Livingston S, Quilichini T, Booth J, Wong D, Rensing K, Laflamme-Yonkman J . Cannabis glandular trichomes alter morphology and metabolite content during flower maturation. Plant J. 2019; 101(1):37-56. DOI: 10.1111/tpj.14516. View

Skell J, Kahn M, Foxman B . Δ-Tetrahydrocannabinolic acid A, the precursor to Δ-tetrahydrocannabinol (THC). Acta Crystallogr C Struct Chem. 2021; 77(Pt 2):84-89. DOI: 10.1107/S2053229621000280. View

McPartland J, MacDonald C, Young M, Grant P, Furkert D, Glass M . Affinity and Efficacy Studies of Tetrahydrocannabinolic Acid A at Cannabinoid Receptor Types One and Two. Cannabis Cannabinoid Res. 2017; 2(1):87-95. PMC: 5510775. DOI: 10.1089/can.2016.0032. View

Danelius E, Halaby S, van der Donk W, Gonen T . MicroED in natural product and small molecule research. Nat Prod Rep. 2020; 38(3):423-431. PMC: 7965795. DOI: 10.1039/d0np00035c. View

Hillig K, Mahlberg P . A chemotaxonomic analysis of cannabinoid variation in Cannabis (Cannabaceae). Am J Bot. 2011; 91(6):966-75. DOI: 10.3732/ajb.91.6.966. View

Happyana N, Agnolet S, Muntendam R, van Dam A, Schneider B, Kayser O . Analysis of cannabinoids in laser-microdissected trichomes of medicinal Cannabis sativa using LCMS and cryogenic NMR. Phytochemistry. 2013; 87:51-9. DOI: 10.1016/j.phytochem.2012.11.001. View

Milay L, Berman P, Shapira A, Guberman O, Meiri D . Metabolic Profiling of Secondary Metabolites for Evaluation of Optimal Postharvest Storage Conditions. Front Plant Sci. 2020; 11:583605. PMC: 7593247. DOI: 10.3389/fpls.2020.583605. View

Korte F, Haag M, Claussen U . Tetrahydrocannabinolcarboxylic acid, a component of hashish. 1. Angew Chem Int Ed Engl. 1965; 4(10):872. DOI: 10.1002/anie.196508721. View

Magagnini G, Grassi G, Kotiranta S . The Effect of Light Spectrum on the Morphology and Cannabinoid Content of Cannabis sativa L. Med Cannabis Cannabinoids. 2021; 1(1):19-27. PMC: 8489345. DOI: 10.1159/000489030. View

10.

Lewis M, Yang Y, Wasilewski E, Clarke H, Kotra L . Chemical Profiling of Medical Cannabis Extracts. ACS Omega. 2018; 2(9):6091-6103. PMC: 6044620. DOI: 10.1021/acsomega.7b00996. View

11.

Wang Y, Deng W, Wang F, Su Y, Feng Y, Chen P . Study of the simulated sunlight photolysis mechanism of ketoprofen: the role of superoxide anion radicals, transformation byproducts, and ecotoxicity assessment. Environ Sci Process Impacts. 2017; 19(9):1176-1184. DOI: 10.1039/c7em00111h. View

12.

Hanus L, Meyer S, Munoz E, Taglialatela-Scafati O, Appendino G . Phytocannabinoids: a unified critical inventory. Nat Prod Rep. 2016; 33(12):1357-1392. DOI: 10.1039/c6np00074f. View

13.

Sirikantaramas S, Taura F, Tanaka Y, Ishikawa Y, Morimoto S, Shoyama Y . Tetrahydrocannabinolic acid synthase, the enzyme controlling marijuana psychoactivity, is secreted into the storage cavity of the glandular trichomes. Plant Cell Physiol. 2005; 46(9):1578-82. DOI: 10.1093/pcp/pci166. View

14.

Bilodeau S, Wu B, Rufyikiri A, MacPherson S, Lefsrud M . An Update on Plant Photobiology and Implications for Cannabis Production. Front Plant Sci. 2019; 10:296. PMC: 6455078. DOI: 10.3389/fpls.2019.00296. View

15.

Elhendawy M, Wanas A, Radwan M, Azzaz N, Toson E, ElSohly M . Chemical and Biological Studies of Roots. Med Cannabis Cannabinoids. 2020; 1(2):104-111. PMC: 7158750. DOI: 10.1159/000495582. View

16.

McPartland J . Systematics at the Levels of Family, Genus, and Species. Cannabis Cannabinoid Res. 2018; 3(1):203-212. PMC: 6225593. DOI: 10.1089/can.2018.0039. View

17.

Meija J, McRae G, Miles C, Melanson J . Thermal stability of cannabinoids in dried cannabis: a kinetic study. Anal Bioanal Chem. 2021; 414(1):377-384. DOI: 10.1007/s00216-020-03098-2. View

18.

Tsujikawa K, Mohri H, Kuwayama K, Miyaguchi H, Iwata Y, Gohda A . Analysis of hallucinogenic constituents in Amanita mushrooms circulated in Japan. Forensic Sci Int. 2006; 164(2-3):172-8. DOI: 10.1016/j.forsciint.2006.01.004. View

19.

Raikos N, Schmid H, Nussbaumer S, Ambach L, Lanz S, Langin A . Determination of Δ9-tetrahydrocannabinolic acid A (Δ9-THCA-A) in whole blood and plasma by LC-MS/MS and application in authentic samples from drivers suspected of driving under the influence of cannabis. Forensic Sci Int. 2014; 243:130-6. DOI: 10.1016/j.forsciint.2014.07.026. View

20.

Shoyama Y, Takeuchi A, Taura F, Tamada T, Adachi M, Kuroki R . Crystallization of Delta1-tetrahydrocannabinolic acid (THCA) synthase from Cannabis sativa. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2006; 61(Pt 8):799-801. PMC: 1952348. DOI: 10.1107/S1744309105023365. View