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五味子果实中具有一氧化氮产生及α-葡萄糖苷酶抑制活性的结构多样的倍半萜类化合物。

Structurally Diverse Sesquiterpenoids with NO Production and α-Glucosidase Inhibitory Activities from the Fruits of Schisandra chinensis.

作者信息

Sun Ping, Pan Yin-Bo, Ma Ren-Fen, Zhao Xue-Chun, Wang Yin-Yin, Miao Lei, Zhang Hua

机构信息

School of Biological Science and Technology, University of Jinan, 336 West Road of Nan Xinzhuang, Jinan, 250022, China.

出版信息

Chem Biodivers. 2023 Oct;20(10):e202301203. doi: 10.1002/cbdv.202301203. Epub 2023 Sep 20.

Abstract

Chemical fractionation of the AcOEt partition, generated from the EtOH extract of the fruits of Schisandra chinensis, afforded a series of sesquiterpenyl constituents including two new cadinanes, a new eudesmane, two new widdranes (a handling artefact and a new natural product), a new bisabolane and two new natural cuparane enantiomers, along with 15 known structurally related analogs. Structures of the new compounds were unambiguously characterized by interpretation of detailed spectroscopic data including ESI-MS and 1D/2D NMR, with their absolute configurations being established by electronic circular dichroism (ECD) calculation and induced ECD experiment. The inhibitory effects of all the isolates against α-glucosidase and lipopolysaccharide (LPS) induced nitric oxide (NO) production in murine RAW264.7 macrophages, as well as their antibacterial and cytotoxic potential, were evaluated, with selective compounds showing moderate α-glucosidase and NO inhibitory activity. Notably, canangaterpene III exhibited the most significant NO inhibitory effect with an IC value of 31.50±1.49 μM.

摘要

对五味子果实乙醇提取物的乙酸乙酯萃取物进行化学分离,得到了一系列倍半萜类成分,包括两种新的杜松烷、一种新的桉叶烷、两种新的维德兰烷(一种处理产物和一种新的天然产物)、一种新的没药烷以及两种新的天然库帕烷对映体,还有15种已知的结构相关类似物。通过对包括电喷雾电离质谱(ESI-MS)和一维/二维核磁共振(1D/2D NMR)在内的详细光谱数据进行解析,明确了新化合物的结构,并通过电子圆二色光谱(ECD)计算和诱导ECD实验确定了它们的绝对构型。评估了所有分离物对小鼠RAW264.7巨噬细胞中α-葡萄糖苷酶和脂多糖(LPS)诱导的一氧化氮(NO)生成的抑制作用,以及它们的抗菌和细胞毒性潜力,一些选择性化合物表现出中等程度的α-葡萄糖苷酶和NO抑制活性。值得注意的是,卡南加萜烯III表现出最显著的NO抑制作用,IC值为31.50±1.49 μM。

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