Cannabis and eicosanoids: A review of molecular pharmacology

Journal of Cannabis Therapeutics

Volumn 1, Issue 1, 2001, Pages 71-83

  McPartland, John M ^a  

^a UNIVERSITY OF VERMONT COLLEGE OF MEDICINE   (United States)

Author keywords

Anandamide; Cannabinoids; Cannabis; Cyclooxygenase; Leukotrienes; Lipooxygenase; Marijuana; Phospho lipase; Prostaglandins; Tetrahydrocannabinol; Thromboxanes

Indexed keywords

EID: 0002119270     PISSN: 15299775     EISSN: None     Source Type: Journal    
DOI: 10.1300/J175v01n01_06     Document Type: Review

References (40)

1. Bornheim, L. M., Everhart, E. T., Li, J. M., and Correia, M. A., 1993. Characterization of cannabidiol-mediated cytchhrome P450 inactivation. Biochem Pharmacol, 45:1323–1331.
2. Burstein, S., Budrow, J., DeBatis, M., Hunter, S. A., and Subramanian, A., 1994. Phospholi-pase participation in cannabinoid-induced release of free arachidonic acid. Biochem Pharmcol, 48:1253–64.
3. Burstein, S., and Hunter, S. A., 1977. Prostaglandins and Cannabis-Vl. Release of arachidonic acid from HeLa cells by ? i-tetrahydrocannabinol and other cannabi-noids. Biochem Pharmacol, 27:1275–1280.
4. Burstein, S., Levin, E., and Varanelli, C., 1973. Prostaglandins and Cannabis-ll. Inhibition of biosynthesis by the naturally occurring cannabinoids. Biochem. Pharmacol, 22:2905–2910.
5. Burstein, S., and Raz, A., 1972. Inhibition of prostaglandin E2 biosynthesis by ? i-tet-rahydrocannabinol. Prostaglandins, 2:369–375.
6. Burstein, S., Taylor, P., El-Feraly, F. S., and Turner, C., 1976. Prostaglandins and Can-nabis-V. Identification of p-vinylphenol as a potent inhibitor of prostaglandin synthesis. Biochem Pharmacol, 25:2003–2004.
7. Burstein, S., Varanelli, C., and Slade, L. T., 1975. Prostaglandins and Cannabis-Hl. Inhibition of biosynthesis by essential oil components of marihuana. Biochem Pharmacol, 24:1053–1054.
8. Chen, Y. Q., Hagmann, W., and Honn, K. V., 1997. Regulation of 12(S)-HETE production in tumor cells. Adv Exp Med Biol, 400:159–166.
9. DeLuca, P., Rothman, D., and Zurier, R. B., 1995. Marine and botanical lipids as immunomodulatory and therapeutic agents in the treatment of rheumatoid arthritis. Rheumatic Disease Clinics North America, 21:759–777.
10. Devane, W. A., Dysarz, F. A., Johnson, M. R., Melvin, L. S., and Howlett, A. C., 1988. Determination and characterization of a cannabinoid receptor in rat brain. Molecular Pharmacol, 34:605–613.
11. Di Marzo, V., De Petrocellis, L., Bisogno, T., and Maurelli, S., 1997. The endogenous cannabimimetic eicosanoid, anandamide, induces arachidonate release in J774 mouse macrophages. Advan Exp Med Biol, 407:341–6.
12. Drazen, J. M., Israel, E., and O’Byrne, M., 1999. Treatment of asthma with drugs modifying the leukotriene pathway. New England J Med., 340:197–206.
13. Evans, A. T., Formukong, E. A., and Evans, F. J., 1987. Actions of cannabis constituents on enyzmes of arachidonate metabolism:anti-inflammatory potential. Biochem Pharmacol, 36:2035–2037.
14. Felder, C. C., Velus, J. S., Williams, H. L., Briley, E. M., and Matsuda, L. A., 1992. Canna-binoid agonists stimulate both receptor-and non-receptor-mediated signal trans-duction pathways in cells transfected with and expressing cannabinoid receptor clones. Molecular Pharmacol, 42:838–845.
15. Felder, C. C., Briley, E. M., Axelrod, J., Simpson, J. T., Mackie, K., and Devane, W. A., 1993. Anandamide, an endogenous cannabimimetic eicosanoid, binds to the cloned human cannabinoid receptor and stimulates receptor-mediated signal transduction. Proc Natl Acad Sci USA, 90:7656–7660.
16. Felder, C. C., and Glass, M., 1998. Cannabinoid receptors and their endogenous agonists. Annu Rev Pharicol Toxicol, 38:179–200.
17. 4 in mouse whole blood ex vivo and human polymorphonuclear cells in vitro by the cannabinoid analgesic cannabi-diol. Phytotherapy Research, 5:258–261.
18. Glass, M., and Felder, C. C., 1997. Concurrent stimulation of cannabinoid CB1 and dopamine D2 receptors augments cAMP accumulation in striatal neurons:evidence for a Gs linkage to the CB1 receptor. J Neuroscience, 17:5327–5333.
19. Glass, M., and Northup, J. K., 1999. Agonist selective regulation of G-proteins by cannabi-noid CB1 and CB2 receptors. Molecular Pharmacology, in press
20. Graham, J. D.P., 1976. “If Cannabis were a new drug”. In Cannabis and Health, Edited by:Graham, J. D.P., 417–437. London:Academic Press.
21. Hawkey, C. J., 1999. COX-2 inhibitors. Lancet, 353:307–314.
22. Hunter, S. A., and Burstein, S. H., 1997. Receptor mediation in cannabinoid stimulated arachidonic acid mobilization and anandamide synthesis. Life Sciences, 18:1563–1573.
23. Klein, T. W., Newton, C., and Friedman, H., 1998a. Cannabinoid receptors and the cytokine network. Adv Exper Biol Med, 437:215–222.
24. Klein, T. W., Friedman, H., and Specter, S., 1998b. Marijuana, immunity and infection. J Neuroimmunology, 83:102–115.
25. McGill, K. A., and Busse, W. W., 1996. Zileuton. Lancet, 348:519–524.
26. McPartland, J. M., and Pruitt, F. L., 1999. Side effects of pharmaceuticals not elicited by comparable herbal medicines:the case of tetrahydrocannabinol and marijuana. Alternative Therapies in Health & Medicine, 5(4):57–62.
27. Mechoulam, R., 1986. Cannabinoids as Therapeutic Agents, 186Boca Raton, FL:CRC Press.
28. O’Shaughnessy, W. B., 1839. On the preparations of the Indian hemp, or gunjah (Cannabis indica). Transactions Medical and Physical Society of Bengal,:421–461. 1838–1840
29. Pate, D., 1999. “Hemp seed:a valuable food source”. In Advances in Hemp Research, Edited by:Ranalli, P., 243–255. Binghamton, NY:The Haworth Press, Inc.
30. Pestonjamasp, V. K., and Burstein, S. H., 1998. Anandamide synthesis is induced by arachidonate mobilizing agonists in cells of the immune system. Biochimica Biophysica Acta, 1394:249–260.
31. 9-tetrahydrocanflabinol inhibits arachidonic acid acylation of phospholipids and triacylglycerols in guinea pig cerebral cortex slices. Molec Pharmacol, 40:547–555.
32. Riccio, M. M., Matsumoto, T., Adcock, J. J., Douglas, G. J., Spina, D., and Page, C. P., 1997. The effect of 15-HPETE on airway responsiveness and pulmonary cell recruitment in rabbits. Br J Pharmacol, 122:249–256.
33. Sheehan, K. M., Sheahan, K., O’Donoghue, D. P., MacSweeney, F., Conroy, R. M., Fitzgerald, D. J., and Murray, F. E., 1999. The relationship between cyclooxygenase-2 expression and colorectal cancer. JAMA, 282:1254–1257.
34. Stefano, G. B., Liu, Y., and Goligorsky, M. S., 1996. Cannabinoid receptors are coupled to nitric oxide release in invertebrate immunocytes, microglia, and human monocytes. J. Biological Chem, 271:19238–19242.
35. Sulcova, E., Methoulam, R., and Fride, E., 1998. Biphasic effects of anandamide. Pharmacol Biochem Behav, 59:347–352.
36. Waksman, Y., Olson, J. M., Carlisle, S. J., and Cabral, G. A., 1999. The central cannabinoid receptor (CB1) mediates inhibition of nitric oxide production by rat microglial cells. Pharmacol. Exp. Therap., 288:1357–1366.
37. Wartmann, M., Campbell, D., Subramanian, A., Burstein, S. H., and Davis, R. J., 1995. The MAP kinase signal transduction pathway is activated by the endogenous cannabinoid anandamide. FEBS Letters, 359:133–136.
38. White, H. L., and Tansik, R. L., 1980. Effects of delta-9-tetrahydrocannabinol and cannabidiol on phospholipase and other enzymes regulating arachidonate metabolism. Prostaglandins & Medicine, 4:409–417.
39. Zurier, R. B., 1993. “Prostaglandins, leukotrienes, and related compounds”. In Textbook of Rheumatology, 4th ed., Edited by:Kelly, W. N., Harris, E. D., Ruddy, S., and Sledge, C. B., Vol. 1, 201–212. Philadelphia, PA:W.B. Saunders Co.
40. Zurier, R. B., Rossetti, R. G., Lane, J. H., Goldberg, J. M., Hunter, S. A., and Burstein, S. H., 1998. Dimethylheptyl-THC-11-oic acid-a nonpsychoactive antiinflammatory agent with a cannabinoid template structure. Arthritis & Rheumatism, 41:163–170.