Details

Autor(en) / Beteiligte

• Choi, Y.H
• Hazekamp, A
• Peltenburg-Looman, A.M.G
• Frederich, M
• Erkelens, C
• Lefeber, A.W.M
• Verpoorte, R

Titel

NMR assignments of the major cannabinoids and cannabiflavonoids isolated from flowers of Cannabis sativa

Ist Teil von

• Phytochemical analysis, 2004-11, Vol.15 (6), p.345-354

Ort / Verlag

Chichester, UK: John Wiley & Sons, Ltd

Erscheinungsjahr

2004

Link zum Volltext

Quelle

Single Title from Wiley-Blackwell

Beschreibungen/Notizen

• The complete 1H- and 13C-NMR assignments of the major Cannabis constituents, delta 9-tetrahydrocannabinol, tetrahydrocannabinolic acid, delta 8-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 1H- and 13C-NMR, 1H-1H-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 1H-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.