Synthesis of the Cannabimovone and Cannabifuran Class of Minor Phytocannabinoids and Their Anti-inflammatory Activity

David G. Dennis, Shravanthi D. Anand, Angel J. Lopez, Jan Petrovčič, Aditi Das, David Sarlah

Research output: Contribution to journalArticlepeer-review

Abstract

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.

Original languageEnglish (US)
Pages (from-to)6075-6086
Number of pages12
JournalJournal of Organic Chemistry
Volume87
Issue number9
DOIs
StatePublished - May 6 2022

ASJC Scopus subject areas

  • Organic Chemistry

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