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异丁香酚，一种从白茅根茎中分离出的新型一氧化氮合酶抑制剂。

Isoeugenin, a Novel Nitric Oxide Synthase Inhibitor Isolated from the Rhizomes of Imperata cylindrica.

作者信息

An Hyo-Jin, Nugroho Agung, Song Byong-Min, Park Hee-Juhn

机构信息

Department of Pharmacology, College of Korean Medicine, Sangji University, Wonju 220-702, Korea.

Department of Agro-Industrial Technology, Faculty of Agriculture, Lambung Mangkurat University, Indonesia 70712, Indonesia.

出版信息

Molecules. 2015 Dec 1;20(12):21336-45. doi: 10.3390/molecules201219767.

DOI:10.3390/molecules201219767
PMID:26633331
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6332495/
Abstract

Phytochemical studies on the constituents of the rhizomes of Imperata cylindrica (Gramineae) were performed using high-performance liquid chromatography (HPLC). We also aimed to search for any biologically active substance capable of inhibiting nitric oxide (NO) formation in lipopolysaccharide (LPS)-activated macrophage 264.7 cells, by testing four compounds isolated from this plant. Four compounds, including a new chromone, isoeugenin, along with ferulic acid, p-coumaric acid, and caffeic acid were isolated and identified by NMR spectroscopy. The structure of isoeugenin was determined as 7-hydroxy-5-methoxy-2-methylchromone by the 2D-NMR technique. Among the four compounds, isoeugenin has the lowest IC50 value on the inhibition of NO production in LPS-activated macrophage RAW264.7 cells (IC50, 9.33 μg/mL). In addition, isoeugenin significantly suppressed the LPS-induced expressions of inducible nitric oxide synthase (iNOS), cyclooxygenase-2 (COX-2), and proinflammatory cytokines mRNA levels. Taken together, these results suggest that the anti-inflammatory activity of isoeugenin is associated with the down-regulation of iNOS, COX-2, and pro-inflammatory cytokines in RAW264.7 cells. Accordingly, our results suggest that the new chromone isoegenin should be considered a potential treatment for inflammatory disease.

摘要

利用高效液相色谱法（HPLC）对白茅（禾本科）根茎的成分进行了植物化学研究。我们还旨在通过测试从该植物中分离出的四种化合物，寻找任何能够抑制脂多糖（LPS）激活的巨噬细胞264.7细胞中一氧化氮（NO）形成的生物活性物质。通过核磁共振光谱法分离并鉴定了四种化合物，包括一种新的色酮、异欧前胡素，以及阿魏酸、对香豆酸和咖啡酸。通过二维核磁共振技术确定异欧前胡素的结构为7-羟基-5-甲氧基-2-甲基色酮。在这四种化合物中，异欧前胡素对LPS激活的巨噬细胞RAW264.7细胞中NO产生的抑制作用具有最低的半数抑制浓度（IC50）值（IC50，9.33μg/mL）。此外，异欧前胡素显著抑制LPS诱导的诱导型一氧化氮合酶（iNOS）、环氧化酶-2（COX-2）的表达以及促炎细胞因子的mRNA水平。综上所述，这些结果表明异欧前胡素的抗炎活性与RAW264.7细胞中iNOS、COX-2和促炎细胞因子的下调有关。因此，我们的结果表明，新的色酮异欧前胡素应被视为炎症性疾病的一种潜在治疗方法。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/994b/6332495/392ff4972f04/molecules-20-19767-g004a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/994b/6332495/4ee0132c3292/molecules-20-19767-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/994b/6332495/deb2a8804ae7/molecules-20-19767-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/994b/6332495/42383830a240/molecules-20-19767-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/994b/6332495/392ff4972f04/molecules-20-19767-g004a.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/994b/6332495/4ee0132c3292/molecules-20-19767-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/994b/6332495/deb2a8804ae7/molecules-20-19767-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/994b/6332495/42383830a240/molecules-20-19767-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/994b/6332495/392ff4972f04/molecules-20-19767-g004a.jpg

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