Novel lignans from Syringa pinnatifolia and protective effect against H2O2-induced oxidative injury through regulating the expression of Nrf2/HO-1 in H9c2 cells

IF 4.5 2区医学 Q1 BIOCHEMISTRY & MOLECULAR BIOLOGY

Bioorganic Chemistry Pub Date : 2024-08-16 DOI:10.1016/j.bioorg.2024.107732

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Abstract

Phytochemical analysis of the peeled stems of Syringa pinnatifolia Hemsl. led to the discovery of 13 undescribed lignans, namely helanols A and B (1 and 2) and alashanenols W–G₁ (3–13), as well as four known analogues, of which helanols A and B were lignans with novel skeleton of α-β′ linkage. The structures were unambiguously established by extensive spectroscopic analyses, NMR calculations, ECD calculations, and single crystal X-ray crystallography. Five lignans (1, 2, 5, 11 and 13) exhibited a moderate protective effect against H₂O₂-induced oxidative injuries in H9c2 cells with the protective rates of 11.3–20.6 % at the concentration of 0.3–20 μM, while the positive control quercetin showed protective rates of 58.7 % at 10 μM. Further mechanism investigation suggested that 1 and 2 exerted the protective effect by regulating the expression of Nrf2/HO-1.

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羽扇豆中的新型木脂素以及通过调节 H9c2 细胞中 Nrf2/HO-1 的表达对 H2O2 诱导的氧化损伤的保护作用

通过对羽叶忍冬（Syringa pinnatifolia Hemsl.）的去皮茎进行植物化学分析，发现了 13 种未曾描述过的木质素，即 helanols A 和 B（1 和 2）和 alashanenols W-G1（3-13），以及 4 种已知的类似物，其中 helanols A 和 B 是具有新型 α-β′ 连接骨架的木质素。通过大量的光谱分析、核磁共振计算、ECD 计算和单晶 X 射线晶体学研究，它们的结构被明确地确定下来。五种木脂素（1、2、5、11 和 13）对 H2O2 诱导的 H9c2 细胞氧化损伤具有中度保护作用，在 0.3-20 μM 浓度下保护率为 11.3-20.6%，而阳性对照槲皮素在 10 μM 浓度下的保护率为 58.7%。进一步的机理研究表明，1和2是通过调节Nrf2/HO-1的表达来发挥保护作用的。

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来源期刊

Bioorganic Chemistry 生物-生化与分子生物学

CiteScore

9.70

自引率

3.90%

发文量

679

审稿时长

31 days

期刊介绍： Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry. For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature. The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.