Literature DB >> 18303850

Cannabinoid ester constituents from high-potency Cannabis sativa.

Safwat A Ahmed1, Samir A Ross, Desmond Slade, Mohamed M Radwan, Fazila Zulfiqar, Rae R Matsumoto, Yan-Tong Xu, Eddy Viard, Robert C Speth, Vardan T Karamyan, M A ElSohly.   

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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Year:  2008        PMID: 18303850      PMCID: PMC4883103          DOI: 10.1021/np070454a

Source DB:  PubMed          Journal:  J Nat Prod        ISSN: 0163-3864            Impact factor:   4.050


  20 in total

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3.  The volatile oil composition of fresh and air-dried buds of Cannabis sativa.

Authors:  S A Ross; M A ElSohly
Journal:  J Nat Prod       Date:  1996-01       Impact factor: 4.050

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Journal:  Mol Pharmacol       Date:  1988-11       Impact factor: 4.436

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Journal:  Life Sci       Date:  2005-11-02       Impact factor: 5.037

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Authors:  S Munro; K L Thomas; M Abu-Shaar
Journal:  Nature       Date:  1993-09-02       Impact factor: 49.962

8.  Antiprotozoal and antimicrobial activities of O-alkylated and formylated acylphloroglucinols.

Authors:  Sandip B Bharate; Shabana I Khan; Nafees A M Yunus; Siddheshwar K Chauthe; Melissa R Jacob; Babu L Tekwani; Ikhlas A Khan; Inder Pal Singh
Journal:  Bioorg Med Chem       Date:  2006-10-10       Impact factor: 3.641

9.  The cannabinoid CB2 receptor as a target for inflammation-dependent neurodegeneration.

Authors:  John C Ashton; Michelle Glass
Journal:  Curr Neuropharmacol       Date:  2007       Impact factor: 7.363

10.  Chromatographic and spectroscopic profiles of Cannabis of different origins: Part I.

Authors:  R Brenneisen; M A elSohly
Journal:  J Forensic Sci       Date:  1988-11       Impact factor: 1.832

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  32 in total

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Authors:  Abir T El-Alfy; Kelly Ivey; Keisha Robinson; Safwat Ahmed; Mohamed Radwan; Desmond Slade; Ikhlas Khan; Mahmoud ElSohly; Samir Ross
Journal:  Pharmacol Biochem Behav       Date:  2010-03-21       Impact factor: 3.533

2.  Isolation and Pharmacological Evaluation of Minor Cannabinoids from High-Potency Cannabis sativa.

Authors:  Mohamed M Radwan; Mahmoud A ElSohly; Abir T El-Alfy; Safwat A Ahmed; Desmond Slade; Afeef S Husni; Susan P Manly; Lisa Wilson; Suzanne Seale; Stephen J Cutler; Samir A Ross
Journal:  J Nat Prod       Date:  2015-05-22       Impact factor: 4.050

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Authors:  Linda Console-Bram; Jahan Marcu; Mary E Abood
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4.  Colorado Cannabis Legalization and Its Effect on Emergency Care.

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5.  Tetrahydrocannabinolic acid reduces nausea-induced conditioned gaping in rats and vomiting in Suncus murinus.

Authors:  E M Rock; R L Kopstick; C L Limebeer; L A Parker
Journal:  Br J Pharmacol       Date:  2013-10       Impact factor: 8.739

6.  Affinity and Efficacy Studies of Tetrahydrocannabinolic Acid A at Cannabinoid Receptor Types One and Two.

Authors:  John M McPartland; Christa MacDonald; Michelle Young; Phillip S Grant; Daniel P Furkert; Michelle Glass
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7.  Cannabisol, a novel Δ9-THC dimer possessing a unique methylene bridge, isolated from Cannabis sativa.

Authors:  Fazila Zulfiqar; Samir A Ross; Desmond Slade; Safwat A Ahmed; Mohamed M Radwan; Zulfiqar Ali; Ikhlas A Khan; Mahmoud A ElSohly
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8.  Zebrafish as an alternative method for determining the embryo toxicity of plant products: a systematic review.

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9.  Tetrahydrocannabinolic acid is a potent PPARγ agonist with neuroprotective activity.

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10.  Structure determination and absolute configuration of cannabichromanone derivatives from high potency Cannabis sativa.

Authors:  Safwat A Ahmed; Samir A Ross; Desmond Slade; Mohamed M Radwan; Ikhlas A Khan; Mahmoud A Elsohly
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