[Medicinal Chemistry and Pharmacology Focused on Cannabidiol, a Major Component of the Fiber-Type Cannabis]

Yakugaku Zasshi. 2013;133(10):1093-101. doi: 10.1248/yakushi.13-00196.
[Article in Japanese]

Abstract

Considerable attention has focused on cannabidiol (CBD), a major non-psychotropic constituent of fiber-type cannabis plant, and it has been reported to possess diverse biological activities. Although CBD is obtained from non-enzymatic decarboxylation of its parent molecule, cannabidiolic acid (CBDA), several studies have investigated whether CBDA itself is biologically active. In the present report, the author summarizes findings indicating that; 1) CBDA is a selective cyclooxygenase-2 (COX-2) inhibitor, and ii) CBDA possesses an anti-migrative potential for highly invasive cancer cells, apparently through a mechanism involving inhibition of cAMP-dependent protein kinase A, coupled with an activation of the small GTPase, RhoA. Further, the author introduces recent findings on the medicinal chemistry and pharmacology of the CBD derivative, CBD-2',6'-dimethyl ether (CBDD), that exhibits inhibitory activity toward 15-lipoxygenase (15-LOX), an enzyme responsible for the production of oxidized low-density lipoprotein (LDL). These studies establish CBD as both an important experimental tool and as a lead compound for pharmaceutical development. In this review, the author further discusses the potential uses of CBD and its derivatives in future medicines.

Publication types

  • English Abstract
  • Research Support, Non-U.S. Gov't
  • Review

MeSH terms

  • Animals
  • Breast Neoplasms / pathology
  • Cannabidiol / analogs & derivatives
  • Cannabidiol / chemistry*
  • Cannabidiol / pharmacology*
  • Cannabinoids / chemistry
  • Cannabis / chemistry*
  • Cell Movement / drug effects
  • Cells, Cultured
  • Chemistry, Pharmaceutical*
  • Cyclic AMP-Dependent Protein Kinases / antagonists & inhibitors
  • Cyclooxygenase 2 Inhibitors
  • Decarboxylation
  • Drug Discovery
  • Female
  • Humans
  • Lipoproteins, LDL / biosynthesis
  • Lipoxygenase Inhibitors
  • Phytotherapy*
  • rhoA GTP-Binding Protein / metabolism

Substances

  • Cannabinoids
  • Cyclooxygenase 2 Inhibitors
  • Lipoproteins, LDL
  • Lipoxygenase Inhibitors
  • oxidized low density lipoprotein
  • cannabidiol dimethyl ether
  • Cannabidiol
  • Cyclic AMP-Dependent Protein Kinases
  • rhoA GTP-Binding Protein
  • cannabidiolic acid