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Cannabinoid ester constituents from high-potency Cannabis sativa.
J Nat Prod 2008; 71(4):536-42JN

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+Show Affiliations

National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, University, Mississippi 38677, USA.No affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

18303850

Citation

Ahmed, Safwat A., et al. "Cannabinoid Ester Constituents From High-potency Cannabis Sativa." Journal of Natural Products, vol. 71, no. 4, 2008, pp. 536-42.
Ahmed SA, Ross SA, Slade D, et al. Cannabinoid ester constituents from high-potency Cannabis sativa. J Nat Prod. 2008;71(4):536-42.
Ahmed, S. A., Ross, S. A., Slade, D., Radwan, M. M., Zulfiqar, F., Matsumoto, R. R., ... ElSohly, M. A. (2008). Cannabinoid ester constituents from high-potency Cannabis sativa. Journal of Natural Products, 71(4), pp. 536-42. doi:10.1021/np070454a.
Ahmed SA, et al. Cannabinoid Ester Constituents From High-potency Cannabis Sativa. J Nat Prod. 2008;71(4):536-42. PubMed PMID: 18303850.
* Article titles in AMA citation format should be in sentence-case
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, Y1 - 2008/02/28/ PY - 2008/2/29/pubmed PY - 2008/6/14/medline PY - 2008/2/29/entrez SP - 536 EP - 42 JF - Journal of natural products JO - J. Nat. Prod. VL - 71 IS - 4 N2 - 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] SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/18303850/abstract/Cannabinoid_Ester_Constituents_from_High_Potency_Cannabis_sativa_ L2 - https://dx.doi.org/10.1021/np070454a DB - PRIME DP - Unbound Medicine ER -