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. 2008 Apr;71(4):536-42.
doi: 10.1021/np070454a. Epub 2008 Feb 28.

Cannabinoid ester constituents from high-potency Cannabis sativa

Safwat A Ahmed  1 , 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
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Cannabinoid ester constituents from high-potency Cannabis sativa

Safwat A Ahmed et al. J Nat Prod. 2008 Apr.

Erratum in

  • J Nat Prod. 2008 Jun;71(6):1119. Matsumoto, Rae R [added]; Xu, Yan-Tong [added]; Viard, Eddy [added]; Speth, Robert C [added]; Karamyan, Vardan T [added]

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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Figures

Figure 1
Figure 1
Important HMBC (arrows) and COSY (bold) correlations of 1.
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References

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