Abstract

Cannabis sativa is one of the oldest medicinal plants in the world. It was introduced into western medicine during the early 19th century. It contains a complex mixture of secondary metabolites, including cannabinoids and non-cannabinoid-type constituents. More than 500 compounds have been reported from C. sativa, of which 125 cannabinoids have been isolated and/or identified as cannabinoids. Cannabinoids are C21 terpeno-phenolic compounds specific to Cannabis. The non-cannabinoid constituents include: non-cannabinoid phenols, flavonoids, terpenes, alkaloids and others. This review discusses the chemistry of the cannabinoids and major non-cannabinoid constituents (terpenes, non-cannabinoid phenolics, and alkaloids) with special emphasis on their chemical structures, methods of isolation, and identification.

Highlights

  • Cannabis sativa is one of the oldest medicinal plants in the world

  • Cannabis sativa L. belongs to the plant family Cannabaceae, which only has one genus (Cannabis) with only one highly variable species, C. sativa

  • Molecules 2021, 26, 2774 (∆9 -THCV, 6) was isolated from a cannabis tincture of Pakistani origin, using the countercurrent distribution technique to isolate the compound from a light petroleum ether extract and its chemical structure was determined by IR, NMR and MS spectroscopy, and was confirmed by synthesis [14]

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Summary

Introduction

Cannabis sativa L. belongs to the plant family Cannabaceae, which only has one genus (Cannabis) with only one highly variable species, C. sativa. (∆9 -THCV, 6) was isolated from a cannabis tincture of Pakistani origin, using the countercurrent distribution technique to isolate the compound from a light petroleum ether extract and its chemical structure was determined by IR, NMR and MS spectroscopy, and was confirmed by synthesis [14]. In 2015, (−)-∆9 -trans-tetrahydrocannabinal (∆9 -THC aldehyde, 10) was isolated from a high potency variety of C. sativa by applying VLC (Vacuum Liquid Chromatography), silica gel column chromatography, and HPLC chromatographic techniques and identified by 1D and 2D NMR [18]. Three additional cannabinoid-type compounds were isolated and identified in 2015, namely 8α-hydroxy-(−)-∆9 -trans-tetrahydrocannabinol (19), 8β-hydroxy-(−)-∆9 -trans-tetrahydro cannabinol (20), and 11-acetoxy-(−)-∆9 -transtetrahydrocannabinolic acid A (21) from high potency C. sativa.

Cannabinodiol
2.10. Cannabitriol
2.11. Miscellaneous
Miscellaneous-Type
Non-Cannabinoids
Dihydrostilbenes
Dihydrophenanthrenes
Simple
Terpenes
15. Chemical
Diterpenes
17. Chemical
Miscellaneous
Alkaloids
History
13. Characterization

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