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艳山姜果实中的二萜类化合物和二芳基庚烷类化合物及其抗炎活性。

Diterpenoids and diarylheptanoids from the fruits of Alpinia zerumbet and their anti-inflammatory activity.

作者信息

Zhang Zhenghan, Li Guangqian, Luo Xin, Xiao Fang, Zhang Yan, Tang Chunping, Hu Bintao, Xie Zuoquan, Yao Sheng, Ye Yang

机构信息

State Key Laboratory of Drug Research, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; China-Serbia "Belt and Road" Joint Laboratory for Natural Products and Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Shanghai 201203, China; University of Chinese Academy of Sciences, No. 19A Yuquan Road, Beijing 100049, China.

School of Pharmaceutical Sciences, Southern Medical University, Guangzhou 510515, China; Zhongshan Institute for Drug Discovery, Shanghai Institute of Materia Medica, Chinese Academy of Sciences, Zhongshan 528400, China.

出版信息

Fitoterapia. 2025 Jul;184:106662. doi: 10.1016/j.fitote.2025.106662. Epub 2025 Jun 3.

DOI:10.1016/j.fitote.2025.106662
PMID:40472979
Abstract

A chemical investigation of the fruits of Alpinia zerumbet resulted in the isolation of three undescribed diterpenoids, including an unusual tricyclic dinor-diterpenoid (1) and two labdane-type diterpenoids (2 and 4), a new diarylheptanoid (7), and a new tricyclic pyrone (9), along with four known compounds. Their structures were fully established through a comprehensive analysis involving high-resolution electrospray ionization mass spectrometry (HRESI-MS), IR, 1D and 2D NMR spectroscopic data, single-crystal X-ray diffraction, and TDDFT (time-dependent density functional theory) ECD (electronic circular dichroism) calculations. The anti-inflammatory activities of isolated compounds were assessed in stimulator of interferon genes (STING) agonist MSA-2-stimulated human THP1-Dual cells for their inhibitory effects on the interferon-stimulated gene (ISG) pathway. The results showed that compound 5 exhibited remarkable anti-inflammatory effect by significantly inhibiting the expression of IFN-β, ISG-15, and IL-6 in MSA-2-stimulated human THP1-Dual cells.

摘要

对艳山姜果实进行化学研究,从中分离出三种未描述的二萜类化合物,包括一种不寻常的三环二降二萜(1)和两种贝壳杉烷型二萜(2和4)、一种新的二芳基庚烷(7)和一种新的三环吡喃(9),以及四种已知化合物。通过高分辨率电喷雾电离质谱(HRESI-MS)、红外光谱(IR)、一维和二维核磁共振光谱数据、单晶X射线衍射以及含时密度泛函理论(TDDFT)电子圆二色光谱(ECD)计算等综合分析,完全确定了它们的结构。在干扰素基因刺激物(STING)激动剂MSA-2刺激的人THP1-Dual细胞中评估分离化合物的抗炎活性,考察其对干扰素刺激基因(ISG)途径的抑制作用。结果表明,化合物5通过显著抑制MSA-2刺激的人THP1-Dual细胞中IFN-β、ISG-15和IL-6的表达,表现出显著的抗炎作用。

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