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. 2008 Oct 13;49(42):6050-6053.
doi: 10.1016/j.tetlet.2008.07.178.

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

Safwat A Ahmed  1 , Samir A Ross, Desmond Slade, Mohamed M Radwan, Ikhlas A Khan, Mahmoud A Elsohly
Affiliations

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

Safwat A Ahmed et al. Tetrahedron Lett. .

Abstract

Three new cannabichromanone derivatives were isolated from high potency cannabis, along with the known cannabichromanone. Full spectroscopic data, including the use of electronic circular dichroism and Mosher ester analysis to determine the absolute configuration of these compounds, are reported. All isolates were tested for antimicrobial, antimalarial, antileishmanial and anti-oxidant activity.

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Figures

Figure 1
Figure 1
Cannabichromanone derivatives 1–4 with cannabinoid numbering system.
Figure 2
Figure 2
Important HMBC (blue arrows), COSY (red bold) and ROESY (purple double-faced arrow) correlations of 1 and 4.
Figure 3
Figure 3
Conformational analysis for 3. The red arrow indicates the direction of projection. The back wedge represents the plane of the benzenoid ring. The blue arrow indicates ROESY correlation between H3-9 or H3-10 and H-7.
Figure 4
Figure 4
CD spectra for 3 and 4.
Figure 5
Figure 5
Conformation of (S)- and (R)-esters. The atoms and bonds in red are coplanar. The blue arrow indicates the phenyl shielding effect
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