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从德氏鹧鸪花叶片中分离得到的一种新的19(10→9)去甲-大戟烷型三萜及其它萜类成分,以及它们在脂多糖刺激的RAW264.7巨噬细胞中对一氧化氮生成的抑制活性

A New 19(10→9)Abeo-Euphane Triterpenoid with other Terpenoid Components from Trichilia dregeana Leaves and their NO Production Inhibitory Activities in LPS-Stimulated RAW264.7 Macrophages.

作者信息

Mba Nguekeu Yves M, Kodama Takeshi, Paing Htoo Zin, Matheuda Elodie Gaële, Tsepeupon Matchide Marie G, Augustin Ngouela Silvère, Tene Mathieu, Ducret Awouafack Maurice, Morita Hiroyuki

机构信息

Natural Products Chemistry Research Unit, Department of Chemistry, Faculty of Science, University of Dschang, P.O. Box 67, Dschang, Cameroon.

Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama, 930-0194, Japan.

出版信息

Chem Biodivers. 2025 Jan;22(1):e202401919. doi: 10.1002/cbdv.202401919. Epub 2024 Oct 31.

Abstract

Trichilia dregeana Sond. (Meliaceae) is a plant used in traditional medicine to treat wounds. The anti-inflammatory potential of the ethyl acetate leaf extract and the presence of euphane-type triterpenes in this extract have recently been reported by our group. Further investigation of the remaining subfractions of the ethyl acetate fraction afforded a new 19(10→9)abeo-euphane-type triterpenoid (1), along with six known terpenoids (2-7). The structure of the new compound was elucidated by analyses of the HR-ESI-MS, 1D and 2D NMR data and by comparison with previously reported data. We investigated the ability of the compounds to modulate the production of nitric oxide (NO) in LPS-stimulated RAW264.7 macrophages. The known compounds 3 and 6 exhibited moderate (IC 72.06 μM) and mild (IC 98.84 μM) inhibitory activities, respectively, without cytotoxic effects on the cells. These results, in conjunction with our previous findings, emphasize the significant role of terpenoid components in the anti-inflammatory efficacy of T. dregeana leaves and indicate that the rare 3,10-epoxy-19(10→9)abeo-euphane triterpenoids could serve as a chemotaxonomic marker for T. dregeana.

摘要

德氏鹧鸪花(Trichilia dregeana Sond.,楝科)是一种传统医学中用于治疗伤口的植物。我们小组最近报道了乙酸乙酯叶提取物的抗炎潜力以及该提取物中存在大戟烷型三萜。对乙酸乙酯馏分的其余亚馏分进行进一步研究,得到了一种新的19(10→9)去甲-大戟烷型三萜(1),以及六种已知的萜类化合物(2 - 7)。通过高分辨电喷雾电离质谱(HR-ESI-MS)、一维和二维核磁共振(NMR)数据分析以及与先前报道的数据进行比较,阐明了新化合物的结构。我们研究了这些化合物调节脂多糖(LPS)刺激的RAW264.7巨噬细胞中一氧化氮(NO)产生的能力。已知化合物3和6分别表现出中度(IC₅₀ 72.06 μM)和轻度(IC₅₀ 98.84 μM)的抑制活性,且对细胞无细胞毒性作用。这些结果与我们之前的发现相结合,强调了萜类成分在德氏鹧鸪花叶抗炎功效中的重要作用,并表明罕见的3,10-环氧-19(10→9)去甲-大戟烷三萜可作为德氏鹧鸪花的化学分类学标志物。

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