Cannabinoid ester constituents from high-potency Cannabis sativa

J Nat Prod. 2008 Apr;71(4):536-42. doi: 10.1021/np070454a. Epub 2008 Feb 28.

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]

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Animals
  • Aspergillus fumigatus / drug effects
  • Candida albicans / drug effects
  • Cannabinoids / chemistry
  • Cannabinoids / isolation & purification*
  • Cannabinoids / pharmacology
  • Cannabis / chemistry*
  • Escherichia coli / drug effects
  • Esters
  • Microbial Sensitivity Tests
  • Molecular Structure
  • Mycobacterium / drug effects
  • Plants, Medicinal / chemistry*
  • Plasmodium falciparum / drug effects
  • Pseudomonas aeruginosa / drug effects
  • Receptor, Cannabinoid, CB1 / agonists

Substances

  • Cannabinoids
  • Esters
  • Receptor, Cannabinoid, CB1