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Biologically active cannabinoids from high-potency Cannabis sativa.

Abstract

Nine new cannabinoids (1-9) were isolated from a high-potency variety of Cannabis sativa. Their structures were identified as (+/-)-4-acetoxycannabichromene (1), (+/-)-3''-hydroxy-Delta((4'',5''))-cannabichromene (2), (-)-7-hydroxycannabichromane (3), (-)-7R-cannabicoumarononic acid A (4), 5-acetyl-4-hydroxycannabigerol (5), 4-acetoxy-2-geranyl-5-hydroxy-3-n-pentylphenol (6), 8-hydroxycannabinol (7), 8-hydroxycannabinolic acid A (8), and 2-geranyl-5-hydroxy-3-n-pentyl-1,4-benzoquinone (9) through 1D and 2D NMR spectroscopy, GC-MS, and HRESIMS. The known sterol beta-sitosterol-3-O-beta-d-glucopyranosyl-6'-acetate was isolated for the first time from cannabis. Compounds 6 and 7 displayed significant antibacterial and antifungal activities, respectively, while 5 displayed strong antileishmanial activity.

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  • Publisher Full Text
  • Authors

    Radwan MM, Elsohly MA, Slade D, Ahmed SA, Khan IA, Ross SA

    Source

    Journal of natural products 72:5 2009 May 22 pg 906-11

    MeSH

    Animals
    Anti-Bacterial Agents
    Antifungal Agents
    Antimalarials
    Aspergillus fumigatus
    Candida
    Cannabinoids
    Cannabis
    Cercopithecus aethiops
    Escherichia coli
    Gas Chromatography-Mass Spectrometry
    Leishmania donovani
    Methicillin-Resistant Staphylococcus aureus
    Microbial Sensitivity Tests
    Molecular Structure
    Nuclear Magnetic Resonance, Biomolecular
    Plants, Medicinal
    Plasmodium falciparum
    Pseudomonas aeruginosa

    Pub Type(s)

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

    Language

    eng

    PubMed ID

    19344127