Structure-activity relationship of anti-inflammatory meroterpenoids isolated from Dictyopteris polypodioides in RAW264 cells.

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2024-05-22 DOI:10.1093/bbb/zbae038

Momochika Kumagai, Akana Matsuda, Nozomi Shiiba, Tomoki Tsuruta, Hikaru Endo, Keisuke Nishikawa, Yoshiki Morimoto

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Abstract

In this study, we explored anti-inflammatory compounds from the brown alga Dictyopteris polypodioides and isolated 7 meroterpenoids. Their anti-inflammatory activities were evaluated using the lipopolysaccharide-stimulated mouse macrophage cell line, RAW264. Yahazunol (1) exhibited similar nitric oxide (NO) production inhibitory activity as zonarol (2), which has previously been shown to be an anti-inflammatory compound. Yahazunol (1), zonarol (2), and isozonarol (3) inhibited not only NO production but also inducible nitric oxide synthase, interleukin-6, and C-C motif chemokine ligand 2 mRNA expression in RAW264 cells. The structure-activity relationships of the 11 compounds, including their synthetic analogs, revealed the significance of the hydroquinone moiety in the anti-inflammatory activity of these sesquiterpenoids in RAW264 cells. Diacetylated zonarol (9) exhibited an activity comparable to that of zonarol as a result of intracellular deacetylation. These results provide new insights into the anti-inflammatory activity of hydroquinone-containing natural products.

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在 RAW264 细胞中分离自多翅蝶形花的抗炎经络萜类化合物的结构-活性关系。

在这项研究中，我们探索了棕色藻类中的抗炎化合物，并分离出了 7 种美洛珀类化合物。Yahazunol（1）表现出与zonarol（2）相似的一氧化氮（NO）生成抑制活性，而后者先前已被证明是一种抗炎化合物。Yahazunol (1)、zonarol (2) 和 isozonarol (3) 不仅能抑制一氧化氮的产生，还能抑制 RAW264 细胞中诱导型一氧化氮合酶 (iNOS)、白细胞介素-6 (IL6) 和 C-C motif 趋化因子配体 2 (CCL2) mRNA 的表达。这 11 种化合物（包括其合成类似物）的结构-活性关系揭示了对苯二酚分子在这些倍半萜化合物对 RAW264 细胞的抗炎活性中的重要作用。由于细胞内去乙酰化作用，二乙酰化唑纳罗（9）表现出与唑纳罗相当的活性。这些结果为了解含氢醌类天然产品的抗炎活性提供了新的视角。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.