title: Cannabinoid ester constituents from high-potency Cannabis sativa.
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]
authors.affiliation: National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.
authors.forename: Safwat A
authors.initials: SA
authors.lastname: Ahmed
authors.forename: Samir A
authors.initials: SA
authors.lastname: Ross
authors.forename: Desmond
authors.initials: D
authors.lastname: Slade
authors.forename: Mohamed M
authors.initials: MM
authors.lastname: Radwan
authors.forename: Fazila
authors.initials: F
authors.lastname: Zulfiqar
authors.forename: Rae R
authors.initials: RR
authors.lastname: Matsumoto
authors.forename: Yan-Tong
authors.initials: YT
authors.lastname: Xu
authors.forename: Eddy
authors.initials: E
authors.lastname: Viard
authors.forename: Robert C
authors.initials: RC
authors.lastname: Speth
authors.forename: Vardan T
authors.initials: VT
authors.lastname: Karamyan
authors.forename: M A
authors.initials: MA
authors.lastname: ElSohly
mesh_terms: 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
chemical_list: D002186:Cannabinoids; D004952:Esters; D043884:Receptor, Cannabinoid, CB1