NMR assignments of the major cannabinoids and cannabiflavonoids isolated from flowers of Cannabis sativa
- 17 November 2004
- journal article
- research article
- Published by Wiley in Phytochemical Analysis
- Vol. 15 (6), 345-354
- https://doi.org/10.1002/pca.787
Abstract
The complete 1H‐ and 13C‐NMR assignments of the major Cannabis constituents, Δ9‐tetrahydrocannabinol, tetrahydrocannabinolic acid, Δ8‐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. Copyright © 2004 John Wiley & Sons, Ltd.Funding Information
- van Leersumfonds (KNAW)
This publication has 15 references indexed in Scilit:
- Cannabinoids: a real prospect for pain reliefCurrent Opinion in Pharmacology, 2002
- Cationic bis(oxazoline)Cu(II) lewis acid catalysts. Application to the asymmetric synthesis of ent-Δ1-tetrahydrocannabinolTetrahedron Letters, 1997
- The medicinal uses of cannabis and its constituentsPhytotherapy Research, 1989
- Acid-catalysed terpenylations of olivetol in the synthesis of cannabinoidsJournal of the Chemical Society, Perkin Transactions 1, 1988
- Constituents of Cannabis sativa L. XVII. A Review of the Natural ConstituentsJournal of Natural Products, 1980
- Carbon-13 nuclear magnetic resonance spectroscopy of naturally occurring substances. 47. Cannabinoid compoundsThe Journal of Organic Chemistry, 1977
- Effect of Oral Administration of Delta9-Tetrahydrocannabinol on Airway Mechanics in Normal and Asthmatic SubjectsChest, 1976
- Recent advances in the chemistry and biochemistry of cannabisChemical Reviews, 1976
- Hashish. X. Simple one-step synthesis of (-)-.DELTA.1-tetrahydrocannabinol (THC) from p-mentha-2,8-dien-1-ol and olivetolJournal of the American Chemical Society, 1974