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细叶石竹原变种的化学成分及生物活性

Chemical constituents and biological activities of Dianthus elegans var. elegans.

作者信息

Mutlu Kiymet, Sarikahya Nazli Boke, Nalbantsoy Ayse, Kirmizigul Suheyla

机构信息

a Faculty of Science, Department of Chemistry , Ege University , Izmir , Turkey.

b Faculty of Engineering, Department of Bioengineering , Ege University , Izmir , Turkey.

出版信息

Nat Prod Res. 2018 Jun;32(11):1245-1253. doi: 10.1080/14786419.2017.1333988. Epub 2017 Jun 6.

Abstract

Chemical investigation of the aerial parts of Dianthus elegans var. elegans afforded two previously undescribed saponins, named dianosides M-N (1-2), together with four oleanane-type triterpenoid glycosides (3-6). Their structures were elucidated as 3-O-α-L-arabinofuranosyl-16α-hydroxyolean-12-ene-23α, 28β-dioic acid (1) and 3-O-α-L-arabinofuranosyl-(1 → 3)-β-D-glucopyranosyl 16α-hydroxyolean-12-ene-23α-oic acid, 28-O-β-D-glucopyranosyl-(1 → 6)-β-D-glycosyl ester (2) by chemical and extensive spectroscopic methods including IR, 1D, 2D NMR and HRESIMS. Both of the saponins were evaluated for their cytotoxicities against HEK-293, A-549 and HeLa human cancer cells using the MTT method. All compounds showed no substantial cytotoxic activity against tested cell lines. However, dianosides M-N and the n-butanol fraction exhibited considerable haemolysis in human erythrocyte cells. The immunomodulatory properties of dianosides M-N were also evaluated in activated whole blood cells by PMA plus ionomycin. Dianosides M-N increased IL-1β concentration significantly whereas the n-butanol fraction slightly augmented IL-1β secretion. All compounds did not change IL-2 and IFN-γ levels considerably.

摘要

对优雅石竹(Dianthus elegans var. elegans)地上部分进行化学研究,得到了两种此前未被描述的皂苷,命名为石竹皂苷M - N(1 - 2),以及四种齐墩果烷型三萜糖苷(3 - 6)。通过化学方法以及包括红外光谱(IR)、一维(1D)、二维(2D)核磁共振(NMR)和高分辨电喷雾电离质谱(HRESIMS)在内的广泛光谱方法,确定它们的结构分别为3 - O - α - L - 阿拉伯呋喃糖基 - 16α - 羟基齐墩果 - 12 - 烯 - 23α, 28β - 二酸(1)和3 - O - α - L - 阿拉伯呋喃糖基 - (1→3) - β - D - 吡喃葡萄糖基16α - 羟基齐墩果 - 12 - 烯 - 23α - 酸,28 - O - β - D - 吡喃葡萄糖基 - (1→6) - β - D - 糖苷酯(2)。使用MTT法评估了这两种皂苷对人胚肾细胞(HEK - 293)、人肺癌细胞(A - 549)和人宫颈癌细胞(HeLa)的细胞毒性。所有化合物对测试细胞系均未显示出显著的细胞毒性活性。然而,石竹皂苷M - N和正丁醇部分在人红细胞中表现出相当程度的溶血作用。还通过佛波酯(PMA)加离子霉素在活化的全血细胞中评估了石竹皂苷M - N的免疫调节特性。石竹皂苷M - N显著增加白细胞介素 - 1β(IL - 1β)浓度,而正丁醇部分轻微增加IL - 1β分泌。所有化合物对白细胞介素 - 2(IL - 2)和干扰素 - γ(IFN - γ)水平的影响不大。

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