Reference : NMR assignments of the major Cannabinoids and cannabiflavonoids isolated from flowers...
Scientific journals : Article
Life sciences : Biochemistry, biophysics & molecular biology
Life sciences : Phytobiology (plant sciences, forestry, mycology...)
NMR assignments of the major Cannabinoids and cannabiflavonoids isolated from flowers of Cannabis sativa
Choi, Y. H. [> > > >]
Hazekamp, A. [> > > >]
Peltenburg-Looman, A. M. G. [> > > >]
Frederich, Michel mailto [Université de Liège - ULiège > Département de pharmacie > Pharmacognosie >]
Erkelens, C. [> > > >]
Lefeber, A. W. M. [> > > >]
Verpoorte, R. [> > > >]
Phytochemical Analysis
John Wiley & Sons Ltd
Yes (verified by ORBi)
[en] NMR assignment ; cannabinoids ; cannabiflavonoids ; Cannabis sativa
[en] The complete H-1- and C-13-NMR assignments of the major Cannabis constituents, Delta(9)-tetrahydrocannabinol, tetrahydrocannabinolic acid, A-tetrahydrocannabinol, cannabigerol, cannabinol, cannabidiol, cannabidiolic acid, cannflavin A and cannflavin B have been determined on the basis of one- and two-dimensional NMR spectra including H-1- and (13)-NMR, H-1-H-1-COSY, HMQC and HMBC. The substitution of carboxylic acid on the cannabinoid nucleus (as in tetrahydrocannabinolic acid and cannabidiolic acid) has a large effect on the chemical shift of H-1" of the C5 side chain and 2'-OH. It was also observed that carboxylic acid substitution reduces intermolecular hydrogen bonding resulting in a sharpening of the H-5' signal in cannabinolic acid in deuterated chloroform. The additional aromaticity of cannabinol causes the two angular methyl groups (H-8 and H-9) to show identical H-1-NMR shifts, which indicates that the two aromatic rings are in one plane in contrast to the other cannabinoids. For the cannabiflavonoids, the unambiguous assignments of C-3' and C-4' of cannflavin A and B were determined by HMBC spectra. Copyright (C) 2004 John Wiley Sons, Ltd.

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