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.
Publication types
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Research Support, N.I.H., Extramural
MeSH terms
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Animals
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Anti-Bacterial Agents
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Antifungal Agents
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Antimalarials / chemistry
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Antimalarials / isolation & purification
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Antimalarials / pharmacology
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Aspergillus fumigatus / drug effects
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Candida / drug effects
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Cannabinoids / chemistry
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Cannabinoids / isolation & purification*
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Cannabinoids / pharmacology*
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Cannabis / chemistry*
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Chlorocebus aethiops
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Escherichia coli / drug effects
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Gas Chromatography-Mass Spectrometry
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Leishmania donovani / drug effects
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Methicillin-Resistant Staphylococcus aureus / drug effects
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Microbial Sensitivity Tests
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Molecular Structure
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Nuclear Magnetic Resonance, Biomolecular
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Plants, Medicinal / chemistry*
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Plasmodium falciparum / drug effects
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Pseudomonas aeruginosa / drug effects
Substances
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4-acetoxy-2-geranyl-5-hydroxy-3-n-pentylphenol
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5-acetyl-4-hydroxycannabigerol
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8-hydroxycannabinol
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Anti-Bacterial Agents
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Antifungal Agents
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Antimalarials
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Cannabinoids