Abstract：
Many polyprenylated acylphloroglucinols with fascinating chemical structures and intriguing biological activities have been identified as key to phytochemicals isolated from Garcinia, Hypericum, and related genera. In the present work, two chiral, tautomeric, highly-oxygenated polyprenylated acylphloroglucinols tethered with acyl and prenyl moieties on a bicyclo[3.3.1]nonanetrione core were isolated from the 95% ethanolic extract of Garcinia gummi-gutta fruit. The structures of both compounds were elucidated based on the NMR and MS data with ambiguity in the exact position of the enol and keto functions at C-1 and C-3 of the core structure. The structures of both polyprenylated acylphloroglucinols were established as a structurally revised guttiferone J and the new iso-guttiferone J with the aid of gauge-independent atomic orbital NMR calculations, CP3 probability analyses, specific rotation calculations, and electronic circular dichroism calculations in combination with the experimental data. The structures of both compounds resemble hyperforin, a potent activator of the human pregnane X receptor. As expected, both compounds showed strong pregnane X receptor activation at 10 µM [7.1-fold (guttiferone J) and 5.0-fold (iso-guttiferone J)], explained by a molecular docking study, necessitating further in-depth investigation to substantiate the herb-drug interaction potential of G. gummi-gutta upon co-administration with pharmaceutical drugs.
摘要：
许多具有令人着迷的化学结构和有趣的生物活性的聚异戊二烯化酰基间苯三酚已被确定为从藤黄中分离出的植物化学物质的关键。金丝桃,和相关属。在目前的工作中,两个手性，互变异构,从藤黄果果实的95％乙醇提取物中分离出在双环[3.3.1]上与酰基和异戊二烯基部分连接的高氧化的聚异戊二烯化酰基间苯三酚。根据NMR和MS数据阐明了这两种化合物的结构，在核心结构的C-1和C-3处的烯醇和酮功能的确切位置存在歧义。借助与规范无关的原子轨道NMR计算，将两种聚戊烯化的酰基间苯三酚的结构都确定为结构上经过修改的甘草酮J和新的异甘草酮J。CP3概率分析，特定旋转计算，并结合实验数据进行电子圆二色性计算。两种化合物的结构类似于hyperforin,人类孕烷X受体的有效激活剂。不出所料,两种化合物均在10µM[7.1倍（guttiferoneJ）和5.0倍（异-guttiferoneJ）]时显示出强孕烷X受体激活，由分子对接研究解释，需要进一步深入研究以证实G.gummi-gutta在与药物共同施用时的草药-药物相互作用潜力。
