Cannabinoid ester constituents from high-potency Cannabis sativa.
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]
Ahmed
Safwat A
SA
National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.
Ross
Samir A
SA
Slade
Desmond
D
Radwan
Mohamed M
MM
Zulfiqar
Fazila
F
Matsumoto
Rae R
RR
Xu
Yan-Tong
YT
Viard
Eddy
E
Speth
Robert C
RC
Karamyan
Vardan T
VT
ElSohly
M A
MA
D000818:Animals; D001232:Aspergillus fumigatus / Q000187:drug effects; D002176:Candida albicans / Q000187:drug effects; D002186:Cannabinoids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002188:Cannabis / Q000737:chemistry*; D004926:Escherichia coli / Q000187:drug effects; D004952:Esters; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D009161:Mycobacterium / Q000187:drug effects; D010946:Plants, Medicinal / Q000737:chemistry*; D010963:Plasmodium falciparum / Q000187:drug effects; D011550:Pseudomonas aeruginosa / Q000187:drug effects; D043884:Receptor, Cannabinoid, CB1 / Q000819:agonists
D002186:Cannabinoids; D004952:Esters; D043884:Receptor, Cannabinoid, CB1