TY - JOUR
T1 - Cannabinoid ester constituents from high-potency Cannabis sativa
AU - Ahmed, Safwat A
AU - Ross, Samir A
AU - Slade, Desmond
AU - Radwan, Mohamed M
AU - Zulfiqar, Fazila
AU - Matsumoto, Rae R
AU - Xu, Yan-Tong
AU - Viard, Eddy
AU - Speth, Robert C
AU - Karamyan, Vardan T
AU - ElSohly, M A
AU - Speth, Robert
PY - 2008/2/28
Y1 - 2008/2/28
N2 - Eleven new cannabinoid esters, together with three known cannabinoid acids and Δ9-tetrahydrocannabinol (Δ9-THC), were isolated from a high-potency variety of Cannabis sativa. The structures were determined by extensive spectroscopic analyses to be β-fenchyl Δ9-tetrahydrocannabinolate (1), epi-bornyl Δ9- tetrahydrocannabinolate (2), α-terpenyl Δ9- tetrahydrocannabinolate (3), 4-terpenyl Δ9- tetrahydrocannabinolate (4), α-cadinyl Δ9- tetrahydrocannabinolate (5), γ-eudesmyl Δ9- tetrahydrocannabinolate (6), γ-eudesmyl cannabigerolate (7), 4-terpenyl cannabinolate (8), bornyl Δ9-tetrahydrocannabinolate (9), α-fenchyl Δ9-tetrahydrocannabinolate (10), α-cadinyl cannabigerolate (11), Δ9-tetrahydrocannabinol (Δ9-THC), Δ9-tetrahydrocannabinolic acid A (Δ9-THCA), cannabinolic acid A (CBNA), and cannabigerolic acid (CBGA). Compound 8 showed moderate antimicrobial activity against Candida albicans ATCC 90028 with an IC50 value of 8.5 μg/mL. CB-1 receptor assay indicated that the esters, as well as the parent acids, are not active. © 2008 American Chemical Society and American Society of Pharmacognosy.
AB - Eleven new cannabinoid esters, together with three known cannabinoid acids and Δ9-tetrahydrocannabinol (Δ9-THC), were isolated from a high-potency variety of Cannabis sativa. The structures were determined by extensive spectroscopic analyses to be β-fenchyl Δ9-tetrahydrocannabinolate (1), epi-bornyl Δ9- tetrahydrocannabinolate (2), α-terpenyl Δ9- tetrahydrocannabinolate (3), 4-terpenyl Δ9- tetrahydrocannabinolate (4), α-cadinyl Δ9- tetrahydrocannabinolate (5), γ-eudesmyl Δ9- tetrahydrocannabinolate (6), γ-eudesmyl cannabigerolate (7), 4-terpenyl cannabinolate (8), bornyl Δ9-tetrahydrocannabinolate (9), α-fenchyl Δ9-tetrahydrocannabinolate (10), α-cadinyl cannabigerolate (11), Δ9-tetrahydrocannabinol (Δ9-THC), Δ9-tetrahydrocannabinolic acid A (Δ9-THCA), cannabinolic acid A (CBNA), and cannabigerolic acid (CBGA). Compound 8 showed moderate antimicrobial activity against Candida albicans ATCC 90028 with an IC50 value of 8.5 μg/mL. CB-1 receptor assay indicated that the esters, as well as the parent acids, are not active. © 2008 American Chemical Society and American Society of Pharmacognosy.
KW - Animals
KW - Aspergillus fumigatus/drug effects
KW - Candida albicans/drug effects
KW - Cannabinoids/chemistry
KW - Cannabis/chemistry
KW - Escherichia coli/drug effects
KW - Esters
KW - Microbial Sensitivity Tests
KW - Molecular Structure
KW - Mycobacterium/drug effects
KW - Plants, Medicinal/chemistry
KW - Plasmodium falciparum/drug effects
KW - Pseudomonas aeruginosa/drug effects
KW - Receptor, Cannabinoid, CB1/agonists
UR - https://nsuworks.nova.edu/hpd_facarticles/95
U2 - 10.1021/np070454a
DO - 10.1021/np070454a
M3 - Article
C2 - 18303850
SN - 0163-3864
VL - 71
SP - 536
EP - 542
JO - Journal of Natural Products
JF - Journal of Natural Products
IS - 4
ER -