Roger Adams Laboratory, Department of Chemistry, University of Illinois, Urbana 61801, Illinois, United States.
Cancer Center at Illinois, University of Illinois, Urbana 61801, Illinois, United States.
J Org Chem. 2022 May 6;87(9):6075-6086. doi: 10.1021/acs.joc.2c00336. Epub 2022 Apr 27.
Despite centuries-long use of 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.
尽管在人类文化中使用大麻已有数百年的历史，而且现在普遍声称其具有药用价值，但只有少数几种植物大麻素经过了严格的药理学特性评估。尽管迄今为止已经记录了超过 100 种不同的次要大麻素，但由于缺乏常规获取足够数量进行测试的途径，对其生物活性的研究很少。在此，我们报告了一种从易得的大麻二酚合成制备几种结构多样的次要大麻素的策略。此外，我们使用 LPS 刺激的 BV2 小胶质细胞检查了它们将激活的小胶质细胞极化成抗炎表型的能力。研究的次要大麻素，特别是大麻素二醇、脱氢大麻素二醇、大麻素酮和 3'-表大麻素酮，抑制了典型促炎生物标志物的产生。这项研究代表了系统研究次要大麻素在用于治疗疼痛和炎症的大麻药用特性中可能发挥作用的开始。
