Cannabis sativa L. - Botany and Biotechnology

7.2 Phytocannabinoids

The typical C21 terpenophenolic skeleton phytocannabinoids isolated fromC.
sativaL represent a class of diverse chemical substances along with their carboxylic
acids, analoges and transformation products. They act on cannabinoid receptors in
cells that repress neurotransmitter release in the brain. The most notable cannabi-
noid is the tetrahydrocannabinol (D^9 -THC, 1 ), the primary psychoactive compound
in cannabis. Cannabidiol (CBD) is another major constituent of the plant (Small and
Marcus 2002 ). Intensive chemical studies have considerably clarified the chemistry
ofC. sativaproducing a total of 120 cannabinoids (Table7.1, Figs.7.1,7.2,7.3,
7.4, 7.5 and 7.6) which can be classified into 11 types: (-)-D^9 - trans-tetra-
hydrocannabinol (D^9 -THC), (-)-D^8 - trans-tetrahydrocannabinol (D^8 -THC), canna-
bigerol (CBG), cannabichromene (CBC), cannabidiol (CBD), cannabinodiol
(CBND), cannabielsoin (CBE), cannabicyclol (CBL), cannabinol (CBN),
cannabitriol (CBT), along with miscellaneous type cannabinoids (Table7.1).

Table 7.1 (continued)

Compound # Name Abbreviation

104 (-)-D^7 - trans-(1R,3R,6R)-

isotetrahydrocannabinol-C5

trans-iso-D^7 -THC

105 Cannabichromanone B –

106 Cannabichromanone C –

107 Cannabichromanone D –

108 (-)-(7R)-cannabicoumarononic acid –

109 4-actoxy-2-geranyl-5-hydroxy-3-n-pentylphenol –

110 2-geranyl-5-hydroxy-3-n-

pentyl-1,4-benzoquinone

111 5-acetoxy-6-geranyl-3-n-

pentyl-1,4-benzoquinone

112 Cannabimovone CBM

113 Cannabioxepane CBX

114 10 a-hydroxy-D9,11-hexahydrocannabinol –

115 9 b,10b-epoxyhexahydrocannabinol –

116 9 a-hydroxyhexahydrocannabinol –

117 7-oxo-9a-hydroxyhexahydrocannabinol –

118 10 a-hydroxyhexahydrocannabinol –

119 10aa-hydroxyhexahydrocannabinol –

120 9 a-hydroxy-10-oxo-D6a,10a-THC –

166 M.M. Radwan et al.