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

IF 1.3 4区生物学 Q4 BIOCHEMISTRY & MOLECULAR BIOLOGY Bioscience, Biotechnology, and Biochemistry 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。

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来源期刊

Bioscience, Biotechnology, and Biochemistry 生物-生化与分子生物学

CiteScore

3.50

自引率

0.00%

发文量

183

审稿时长

1 months

期刊介绍： Bioscience, Biotechnology, and Biochemistry publishes high-quality papers providing chemical and biological analyses of vital phenomena exhibited by animals, plants, and microorganisms, the chemical structures and functions of their products, and related matters. The Journal plays a major role in communicating to a global audience outstanding basic and applied research in all fields subsumed by the Japan Society for Bioscience, Biotechnology, and Agrochemistry (JSBBA).