PROSTAGLANDINS AND CANNABIS .12. THE EFFECT OF CANNABINOID STRUCTURE ON THE SYNTHESIS OF PROSTAGLANDINS BY HUMAN-LUNG FIBROBLASTS

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  • 1 January 1983
    • journal article
    • research article
    • Vol. 23  (1) , 121-126
Abstract
Earlier findings indicated that several other cannabinoids in addition to .DELTA.1-tetrahydrocannabinol (THC) were able to stimulate the synthesis of prostaglandins in cell culture systems. The study was initiated to delineate the structural requirements for this effect within the cannabinoid series. Among the primary cannabinoids, the trend was for more planar structures to show greater activity. In the case of THC metabolites, the order of activity was .DELTA.1-THC > 7-oxo-.DELTA.1,6-THC > 7-OH-.DELTA.1-THC > 3''''-OH-.DELTA.1-THC = 6.beta.-OH-.DELTA.1-THC = 6.alpha.-OH-.DELTA.1-THC > .DELTA.1,6-THC-7-oic acid. The latter sequence compares favorably with the availability data on the behavioral assay in the rhesus monkey and the subjective high in humans. A good correlation was observed between the release of arachidonic acid and the production of prostaglandin E, over a series of 8 cannabinoids. The site of action in this effect is evidently the elevation of activity of the phospholipase(s) responsible for supplying precursor arachidonic acid for prostaglandin synthesis.