Chlorajaponins A—Q, Lindenane-Related Sesquiterpenoid Dimers from Chloranthus japonicus and Their Biological Activities,Chinese Journal of Chemistry

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Chlorajaponins A—Q, Lindenane-Related Sesquiterpenoid Dimers from Chloranthus japonicus and Their Biological Activities
Chinese Journal of Chemistry ( IF 5.5 ) Pub Date : 2024-02-13 , DOI: 10.1002/cjoc.202300731
Wei‐Jiao Feng ₁ , Yue Gu ₁ , Pei‐Zhi Huang ₁ , Hong‐Ying Yang _{1,

2} , Rui Zhang ₁ , Yi‐Lin He _{1,

2} , Ting‐Hong Lv ₁ , Ya Li ₁ , Kun Gao ₁

Affiliation

Seventeen undescribed lindenane-related sesquiterpenoid dimers, chlorajaponins A—Q (1—17), and 13 reported analogs (18—30) were isolated from Chloranthus japonicus Sieb. Compound 1 possesses an unprecedented 3/5/7/5/5/6/5/3 fused octacyclic scaffold, featuring a 6(5→4)-abeo-lindenane monomer, while 2 exhibits a 3/5/6/6/5/6/5/3 fused octacyclic scaffold. Their structures were determined through a combination of spectroscopic analyses and X-ray crystallography. Compounds 1, 2, and 18 demonstrated significant inhibitory effects on lipid accumulation and effectively reduced the levels of triglycerides and total cholesterol, as well as the levels of aspartate aminotransferase and alanine aminotransferase in a HepG2 cell model. In addition, compounds 1, 2, and 18 significantly suppressed the protein expression of the fatty acid synthase (FASN) and the sterol regulatory element-binding protein 1 (SREBP1). Moreover, the anti-inflammatory assay showed that compounds 19—22 and 25 inhibited the NO production induced by lipopolysaccharide in RAW 264.7 macrophages with IC₅₀ values of 7.89 ± 0.44, 6.25 ± 0.46, 2.98 ± 0.29, 10.77 ± 0.60, and 3.60 ± 0.28 μmol/L.

中文翻译：

金粟兰金缕梅苷 A—Q、林烯烷相关倍半萜二聚体及其生物活性

从金粟兰(Chloranthus japonicus Sieb)中分离出17 种未描述的与茚烷相关的倍半萜二聚体、氯皂苷 A—Q ( 1 — 17 ) 和 13 种报道的类似物 ( 18 — 30 ) 。化合物1拥有前所未有的 3/5/7/5/5/6/5/3 稠合八环支架，具有 6(5→4)- abeo -lindenane 单体，而2则具有 3/5/6/6/ 5/6/5/3 融合八环支架。它们的结构是通过光谱分析和 X 射线晶体学的结合确定的。化合物1、2和18在HepG2细胞模型中表现出对脂质积累的显着抑制作用，并有效降低甘油三酯和总胆固醇的水平，以及天冬氨酸转氨酶和丙氨酸转氨酶的水平。此外，化合物1、2和18显着抑制脂肪酸合酶(FASN)和甾醇调节元件结合蛋白1(SREBP1)的蛋白质表达。此外，抗炎测定显示，化合物19-22和25抑制RAW 264.7巨噬细胞中脂多糖诱导的NO产生，IC 50_值为7.89±0.44、6.25±0.46、2.98±0.29、10.77±0.60和3.60 ± 0.28微摩尔/升。

更新日期：2024-02-13

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