Isolation and Characterization of New Cannabis Constituents from a High Potency Variety

Abstract

Phytochemical investigation of a high potency variety of Cannabis sativa L. resulted in the isolation of six new metabolites, (±)-6,7-trans-epoxycannabigerolic acid (2), (±)-6,7-cisepoxycannabigerolic acid (3), (±)-6,7-cis-epoxycannabigerol (4), (±)-6,7-trans-epoxycannabigerol (5), 5′-methyl-4-pentylbiphenyl-2,2′,6-triol (7), and 7-methoxycannabispirone (8), along with seven known compounds namely, cannabigerolic acid (1), 5′-methoxycannabigerolic acid (6), cannabispirone (9), β-cannabispiranol (10), dehydrocannabifuran (11), cannflavin B (12) and cannabigerol (13). The antimicrobial as well as the antileishmanial activities were investigated.

Minor oxygenated cannabinoids from high potency Cannabis sativa L.

“…Isolated compounds were evaluated for antimicrobial ( Candida albicans ATCC 90028, Escherichia coli ATCC 35218, Pseudomonas aeruginosa ATCC 27853, Mycobacterium intracellulare ATCC 23068, Aspergillus fumigatus ATCC 90906, Methicillin Resistant S. aureus ATCC 43300), antileishmanial and antimalarial activity [ P. falciparum (D6 clone) and P. falciparum (W2 clone)] (Radwan et al, 2008a,b), respectively.…”

“…Modification of the structures are limited to changes in the side-chain and the terpenoid portion of the molecule (ElSohly and Slade, 2005). The total number of natural cannabinoids identified in C. sativa L. was 66 in 1995, 70 in 2005 and 105 in 2014 (Ahmed et al, 2008a,b; Appendino et al, 2008; Radwan et al, 2008a,b, 2009; ElSohly and Slade, 2005; ElSohly and Gul, 2014; Ross and ElSohly, 1995). …”

“…In efforts to study the chemistry of high potency cannabis, a variety of new constituents were isolated (Radwan et al, 2008a,b, 2009; Ahmed et al, 2008a,b). Herein reported are the isolation and structure elucidation of nine new oxygenated cannabinoids ( 1 – 9 ) namely, 9α-hydroxyhexahydrocannabinol ( 1 ), 7-oxo-9α-hydroxy-hexahydrocannabinol ( 2 ), 10α-hydroxyhexa-hydrocannabinol ( 3 ), 10a R -hydroxyhexa-hydrocannabinol ( 4 ), Δ 9 -THC aldehyde A ( 5 ), 8-oxo-Δ 9 -THC ( 6 ), 10aR-hydroxy-10-oxo-Δ 8 -THC ( 7 ), 9α-hydroxy-10-oxo-Δ 6a,10a -THC ( 8 ), and 1′ S -hydroxycannabinol ( 9 ) along with other previously identified constituents.…”

Microbial metabolism of cannflavin A and B isolated from Cannabis sativa

“…Recently, a number of new cannabis constituents were identified, increasing the total from 489 in 2005 (ElSohly and Slade, 2005) to 537 in 2009 (Ahmed et al, 2008a,b; Appendino et al, 2008; Radwan et al, 2009, 2008a,b), while the number of cannabinoids increased from 70 to 109. The cannabinoids are the most studied cannabis constituents, in particular Δ 9 -tetrahydrocannabinol (Δ 9 -THC), the main psychoactive component (Galal et al, 2009); however, research has shown that some of the other cannabinoids also exhibit pharmacological activities, e.g., the nonpsychotropic cannabinoid cannabidiol (CBD) displays antihyperalgesic, antipsychotic, anticonvulsant, neuroprotective and antiemetic properties (Galal et al, 2009).…”

“…Cannflavin A and B, two methylated isoprenoid flavones, represent the first aglycone flavonoids uniquely isolated from cannabis. The antileishmanial activity for cannflavin A and B was reported as strong (IC 50 10.3 μM) (Radwan et al, 2008a) and moderate (IC 50 13.6 μM) (Radwan et al, 2008b), respectively.…”