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Non-cannabinoid constituents from a high potency Cannabis sativa variety.

Abstract

Six new non-cannabinoid constituents were isolated from a high potency Cannabis sativa L. variety, namely 5-acetoxy-6-geranyl-3-n-pentyl-1,4-benzoquinone (1), 4,5-dihydroxy-2,3,6-trimethoxy-9,10-dihydrophenanthrene (2), 4-hydroxy-2,3,6,7-tetramethoxy-9,10-dihydrophenanthrene (3), 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene (4), cannflavin C (5) and beta-sitosteryl-3-O-beta-d-glucopyranoside-2'-O-palmitate (6). In addition, five known compounds, alpha-cannabispiranol (7), chrysoeriol (8), 6-prenylapigenin (9), cannflavin A (10) and beta-acetyl cannabispiranol (11) were identified, with 8 and 9 being reported for the first time from cannabis. Some isolates displayed weak to strong antimicrobial, antileishmanial, antimalarial and anti-oxidant activities. Compounds 2-4 were inactive as analgesics.

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  • Authors+Show Affiliations

    ,

    National Center for Natural Products Research, School of Pharmacy, The University of Mississippi, University, MS 38677, USA.

    , , , , , ,

    Source

    Phytochemistry 69:14 2008 Oct pg 2627-33

    MeSH

    Analgesics
    Animals
    Anti-Infective Agents
    Antimalarials
    Antioxidants
    Antiprotozoal Agents
    Biological Products
    Cannabis
    Flavones
    Mice
    Molecular Structure

    Pub Type(s)

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

    Language

    eng

    PubMed ID

    18774146

    Citation

    TY - JOUR T1 - Non-cannabinoid constituents from a high potency Cannabis sativa variety. AU - Radwan,Mohamed M, AU - Elsohly,Mahmoud A, AU - Slade,Desmond, AU - Ahmed,Safwat A, AU - Wilson,Lisa, AU - El-Alfy,Abir T, AU - Khan,Ikhlas A, AU - Ross,Samir A, Y1 - 2008/09/04/ PY - 2008/05/02/received PY - 2008/06/03/revised PY - 2008/07/22/accepted PY - 2008/9/9/pubmed PY - 2009/1/17/medline PY - 2008/9/9/entrez SP - 2627 EP - 33 JF - Phytochemistry JO - Phytochemistry VL - 69 IS - 14 N2 - Six new non-cannabinoid constituents were isolated from a high potency Cannabis sativa L. variety, namely 5-acetoxy-6-geranyl-3-n-pentyl-1,4-benzoquinone (1), 4,5-dihydroxy-2,3,6-trimethoxy-9,10-dihydrophenanthrene (2), 4-hydroxy-2,3,6,7-tetramethoxy-9,10-dihydrophenanthrene (3), 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene (4), cannflavin C (5) and beta-sitosteryl-3-O-beta-d-glucopyranoside-2'-O-palmitate (6). In addition, five known compounds, alpha-cannabispiranol (7), chrysoeriol (8), 6-prenylapigenin (9), cannflavin A (10) and beta-acetyl cannabispiranol (11) were identified, with 8 and 9 being reported for the first time from cannabis. Some isolates displayed weak to strong antimicrobial, antileishmanial, antimalarial and anti-oxidant activities. Compounds 2-4 were inactive as analgesics. SN - 0031-9422 UR - https://www.unboundmedicine.com/medline/citation/18774146/abstract/Non_cannabinoid_constituents_from_a_high_potency_Cannabis_sativa_variety_ L2 - https://linkinghub.elsevier.com/retrieve/pii/S0031-9422(08)00351-8 ER -