Non-cannabinoid constituents from a high potency Cannabis sativa variety

As part of our program to study the phytochemistry of high potency Cannabis sativa L. [1,2], seven new non-cannabinoid constituents were isolated, namely 5-acetoxy-6-geranyl-3-n-pentyl-1,4-benzoquinone (1), 4,5-dihydroxy-2,3,6-trimethoxy-9,10-dihydrophenanthrene (2), 4-hydroxy-2,3,6,7-tetramethoxy-9,10-dihydrophenanthrene (3), 4,7-dimethoxy-1,2,5-trihydroxyphenanthrene (4), α-cannabispiranol (5), cannflavin C (6) and β-sitosteryl-3-O-β-D-glucopyranoside-2'-O-palmitate (7). In addition, four known compounds, chrysoeriol (8), 6-prenyl-apigenin (9), cannflavin A (10) and β-acetyl cannabispiranol (11), were identified, with 8 and 9 being reported for the first time form cannabis. The antimicrobial, antileishmanial, antimalarial and anti-oxidant activities of these isolates were evaluated.

Furthermore the analgesic activity of 2, 3 and 4 was evaluated in mice using the hot-plate and tail-flick nociception models.

Acknowledgements: The project described was supported by Grant Number 5P20RR021929–02 from the National Center for Research Resources and by the National Institute on Drug Abuse, contract # N01DA-5–7746. The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Center for Research Resources or the National Institutes of Health. We are grateful to Dr. Bharathi Avula for assistance with the HR-ESI-MS, and to Dr. Melissa Jacob, Ms. Marsha Wright and Dr. Babu Tekwani for conducting the antimicrobial and antiprotozoal testing.

References: 1. Radwan, M.M., et al. (2008). Planta Med. 74: 267–272.

2. Ahmed, S.A., et al. (2008)J. Nat. Prod. (In press).