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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]

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  • 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.

    , , , , , , , , ,

    Source

    Journal of natural products 71:4 2008 Apr pg 536-42

    MeSH

    Animals
    Aspergillus fumigatus
    Candida albicans
    Cannabinoids
    Cannabis
    Escherichia coli
    Esters
    Microbial Sensitivity Tests
    Molecular Structure
    Mycobacterium
    Plants, Medicinal
    Plasmodium falciparum
    Pseudomonas aeruginosa
    Receptor, Cannabinoid, CB1

    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 -