TY - JOUR
T1 - Synthesis of the Cannabimovone and Cannabifuran Class of Minor Phytocannabinoids and Their Anti-inflammatory Activity
AU - Dennis, David G.
AU - Anand, Shravanthi D.
AU - Lopez, Angel J.
AU - Petrovčič, Jan
AU - Das, Aditi
AU - Sarlah, David
N1 - Funding Information:
Financial support for this work was provided by the University of Illinois and National Center for Complementary and Integrative Health (NCCIH) at the National Institutes of Health (R21 AT010761) to D.S. and A.D. We thank Mr. Teak Jung Oh for initial discussions about the minor cannabinoids. The Bruker 500-MHz NMR spectrometer was obtained with the financial support of the Roy J. Carver Charitable Trust, Muscatine, Iowa, USA. We also thank Dr. D. Olson and Dr. L. Zhu for NMR spectroscopic assistance and F. Sun for mass spectrometric assistance.
Publisher Copyright:
© 2022 American Chemical Society.
PY - 2022/5/6
Y1 - 2022/5/6
N2 - Despite centuries-long use of Cannabis in human culture and the now ubiquitous claims of its medicinal value, only a small handful of phytocannabinoids have been rigorously evaluated for pharmacological properties. While more than 100 distinct minor cannabinoids have been documented to date, a paucity of studies on their biological activities have been conducted due to a lack of routine access to sufficient quantities for testing. Herein, we report a strategy to prepare several structurally diverse minor cannabinoids deriving synthetically from readily available cannabidiol. Furthermore, we examined their ability to polarize activated microglia toward an anti-inflammatory phenotype using LPS-stimulated BV2 microglial cells. The minor cannabinoids studied, especially cannabielsoin, dehydrocannabielsoin, cannabimovone, and 3′-epicannabimovone, inhibited the production of prototypical pro-inflammatory biomarkers. This study represents the beginning of a systematic mapping of the roles minor cannabinoids may play in the medicinal properties of cannabis used for the treatment of pain and inflammation.
AB - Despite centuries-long use of Cannabis in human culture and the now ubiquitous claims of its medicinal value, only a small handful of phytocannabinoids have been rigorously evaluated for pharmacological properties. While more than 100 distinct minor cannabinoids have been documented to date, a paucity of studies on their biological activities have been conducted due to a lack of routine access to sufficient quantities for testing. Herein, we report a strategy to prepare several structurally diverse minor cannabinoids deriving synthetically from readily available cannabidiol. Furthermore, we examined their ability to polarize activated microglia toward an anti-inflammatory phenotype using LPS-stimulated BV2 microglial cells. The minor cannabinoids studied, especially cannabielsoin, dehydrocannabielsoin, cannabimovone, and 3′-epicannabimovone, inhibited the production of prototypical pro-inflammatory biomarkers. This study represents the beginning of a systematic mapping of the roles minor cannabinoids may play in the medicinal properties of cannabis used for the treatment of pain and inflammation.
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U2 - 10.1021/acs.joc.2c00336
DO - 10.1021/acs.joc.2c00336
M3 - Article
C2 - 35476908
AN - SCOPUS:85129153425
SN - 0022-3263
VL - 87
SP - 6075
EP - 6086
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 9
ER -