Cannabinoid Ester Constituents from High-potency Cannabis Sativa

Overview

Journal J Nat Prod

Date 2008 Feb 29

PMID 18303850

Citations 39

Authors

Safwat A Ahmed

Samir A Ross

Desmond Slade

Mohamed M Radwan

Fazila Zulfiqar

Rae R Matsumoto

Yan-Tong Xu

Eddy Viard

Robert C Speth

Vardan T Karamyan

M A ElSohly

Affiliations

Soon will be listed here.

Abstract

Eleven new cannabinoid esters, together with three known cannabinoid acids and Delta9-tetrahydrocannabinol ( Delta9-THC ), were isolated from a high-potency variety of Cannabis sativa. The structures were determined by extensive spectroscopic analyses to be beta-fenchyl Delta9-tetrahydrocannabinolate ( 1), epi-bornyl Delta9-tetrahydrocannabinolate ( 2), alpha-terpenyl Delta9-tetrahydrocannabinolate ( 3), 4-terpenyl Delta 9-tetrahydrocannabinolate ( 4), alpha-cadinyl Delta9-tetrahydrocannabinolate ( 5), gamma-eudesmyl Delta9-tetrahydrocannabinolate ( 6), gamma-eudesmyl cannabigerolate ( 7), 4-terpenyl cannabinolate ( 8), bornyl Delta9-tetrahydrocannabinolate ( 9), alpha-fenchyl Delta9-tetrahydrocannabinolate ( 10), alpha-cadinyl cannabigerolate ( 11), Delta9-tetrahydrocannabinol ( Delta9-THC ), Delta9-tetrahydrocannabinolic acid A ( Delta9-THCA ), cannabinolic acid A ( CBNA), and cannabigerolic acid ( CBGA). Compound 8 showed moderate antimicrobial activity against Candida albicans ATCC 90028 with an IC 50 value of 8.5 microg/mL. The isolated acids and the ester-containing fractions showed low affinity to the CB-1 receptor. [corrected]

Citing Articles

Exploring the diversity of cannabis cannabinoid and non-cannabinoid compounds and their roles in Alzheimer's disease: A review.

Doumar H, Mostafi H, Elhessni A, Touhami M, Mesfioui A IBRO Neurosci Rep. 2025; 18:96-119.

PMID: 39866750 PMC: 11763173. DOI: 10.1016/j.ibneur.2024.12.011.

Evaluation of dispensaries' cannabis flowers for accuracy of labeling of cannabinoids content.

Geweda M, Majumdar C, Moore M, Elhendawy M, Radwan M, Chandra S J Cannabis Res. 2024; 6(1):11.

PMID: 38461280 PMC: 10924369. DOI: 10.1186/s42238-024-00220-4.

: a multifaceted plant with endless potentials.

Fordjour E, Manful C, Sey A, Javed R, Pham T, Thomas R Front Pharmacol. 2023; 14:1200269.

PMID: 37397476 PMC: 10308385. DOI: 10.3389/fphar.2023.1200269.

The impact of phyto- and endo-cannabinoids on central nervous system diseases：A review.

Zhang S, Zhang N, Guo T, Sheen L, Ho C, Bai N J Tradit Complement Med. 2023; 13(1):30-38.

PMID: 36685079 PMC: 9845650. DOI: 10.1016/j.jtcme.2022.10.004.

Optimisation of the Green Process of Industrial Hemp-Preparation and Its Extract Characterisation.

Zitek T, Kotnik P, Makoter T, Postruznik V, Knez Z, Knez Marevci M Plants (Basel). 2022; 11(13).

PMID: 35807701 PMC: 9269414. DOI: 10.3390/plants11131749.

References

Roberts J, Gennings C, Shih M . Synergistic affective analgesic interaction between delta-9-tetrahydrocannabinol and morphine. Eur J Pharmacol. 2005; 530(1-2):54-8. DOI: 10.1016/j.ejphar.2005.11.036. View

Plange N, Arend K, Kaup M, Doehmen B, Adams H, Hendricks S . Dronabinol and retinal hemodynamics in humans. Am J Ophthalmol. 2006; 143(1):173-4. DOI: 10.1016/j.ajo.2006.07.053. View

Mannila J, Jarvinen T, Jarvinen K, Tervonen J, Jarho P . Sublingual administration of Delta9-tetrahydrocannabinol/beta-cyclodextrin complex increases the bioavailability of Delta9-tetrahydrocannabinol in rabbits. Life Sci. 2005; 78(17):1911-4. DOI: 10.1016/j.lfs.2005.08.025. View

Parker L, Kwiatkowska M, Mechoulam R . Delta-9-tetrahydrocannabinol and cannabidiol, but not ondansetron, interfere with conditioned retching reactions elicited by a lithium-paired context in Suncus murinus: An animal model of anticipatory nausea and vomiting. Physiol Behav. 2005; 87(1):66-71. DOI: 10.1016/j.physbeh.2005.08.045. View

Brenneisen R, ElSohly M . Chromatographic and spectroscopic profiles of Cannabis of different origins: Part I. J Forensic Sci. 1988; 33(6):1385-404. View

Devane W, Dysarz 3rd F, Johnson M, Melvin L, Howlett A . Determination and characterization of a cannabinoid receptor in rat brain. Mol Pharmacol. 1988; 34(5):605-13. View

Radwan M, Ross S, Slade D, Ahmed S, Zulfiqar F, ElSohly M . Isolation and characterization of new Cannabis constituents from a high potency variety. Planta Med. 2008; 74(3):267-72. PMC: 4887452. DOI: 10.1055/s-2008-1034311. View

Bharate S, Khan S, Yunus N, Chauthe S, Jacob M, Tekwani B . Antiprotozoal and antimicrobial activities of O-alkylated and formylated acylphloroglucinols. Bioorg Med Chem. 2006; 15(1):87-96. DOI: 10.1016/j.bmc.2006.10.006. View

Tognolini M, Barocelli E, Ballabeni V, Bruni R, Bianchi A, Chiavarini M . Comparative screening of plant essential oils: phenylpropanoid moiety as basic core for antiplatelet activity. Life Sci. 2005; 78(13):1419-32. DOI: 10.1016/j.lfs.2005.07.020. View

10.

Bastola K, Hazekamp A, Verpoorte R . Synthesis and spectroscopic characterization of cannabinolic acid. Planta Med. 2007; 73(3):273-5. DOI: 10.1055/s-2007-967129. View

11.

Munro S, Thomas K . Molecular characterization of a peripheral receptor for cannabinoids. Nature. 1993; 365(6441):61-5. DOI: 10.1038/365061a0. View

12.

Mechoulam R, GAONI Y . Recent advances in the chemistry of hashish. Fortschr Chem Org Naturst. 1967; 25:175-213. DOI: 10.1007/978-3-7091-8164-5_6. View

13.

Ashton J, Glass M . The cannabinoid CB2 receptor as a target for inflammation-dependent neurodegeneration. Curr Neuropharmacol. 2008; 5(2):73-80. PMC: 2435344. DOI: 10.2174/157015907780866884. View

14.

ElSohly M, Ross S, Mehmedic Z, Arafat R, Yi B, Banahan 3rd B . Potency trends of delta9-THC and other cannabinoids in confiscated marijuana from 1980-1997. J Forensic Sci. 2000; 45(1):24-30. View

15.

Darmani N, Johnson J . Central and peripheral mechanisms contribute to the antiemetic actions of delta-9-tetrahydrocannabinol against 5-hydroxytryptophan-induced emesis. Eur J Pharmacol. 2004; 488(1-3):201-12. DOI: 10.1016/j.ejphar.2004.02.018. View

16.

Turner C, ElSohly M, Boeren E . Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980; 43(2):169-234. DOI: 10.1021/np50008a001. View

17.

Howlett A, Barth F, Bonner T, Cabral G, Casellas P, Devane W . International Union of Pharmacology. XXVII. Classification of cannabinoid receptors. Pharmacol Rev. 2002; 54(2):161-202. DOI: 10.1124/pr.54.2.161. View

18.

Choi Y, Hazekamp A, Peltenburg-Looman A, Frederich M, Erkelens C, Lefeber A . NMR assignments of the major cannabinoids and cannabiflavonoids isolated from flowers of Cannabis sativa. Phytochem Anal. 2004; 15(6):345-54. DOI: 10.1002/pca.787. View

19.

Sofia R, Kubena R, BARRY 3rd H . Inactivity of delta9-tetrahydrocannabinol in antidepressant screening tests. Psychopharmacologia. 1973; 31(2):121-30. DOI: 10.1007/BF00419812. View

20.

ElSohly M, Slade D . Chemical constituents of marijuana: the complex mixture of natural cannabinoids. Life Sci. 2005; 78(5):539-48. DOI: 10.1016/j.lfs.2005.09.011. View