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从牛油树(山榄科)中提取的具有细胞毒性和抗氧化作用的三萜皂苷。

Cytotoxic and antioxidant triterpene saponins from Butyrospermum parkii (Sapotaceae).

机构信息

Department of Chemistry, Faculty of Science, University of Dschang, Box 183, Dschang, Cameroon.

出版信息

Carbohydr Res. 2011 Dec 13;346(17):2699-704. doi: 10.1016/j.carres.2011.09.014. Epub 2011 Sep 24.

DOI:10.1016/j.carres.2011.09.014
PMID:21996603
Abstract

Three new triterpenoid saponins, elucidated as 3-O-β-D-glucopyranosyloleanolic acid 28-O-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside (parkioside A, 1), 3-O-[β-D-apifuranosyl-(1→3)-β-D-glucopyranosyl]oleanolic acid 28-O-[β-D-apifuranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→3)]-α-L-rhamnopyranosyl-(1→2)β-D-xylopyranoside (parkioside B, 2) and 3-O-β-D-glucuronopyranosyl-16α-hydroxyprotobassic acid 28-O-α-L-rhamnopyranosyl-(1→3)-β-D-xylopyranosyl-(1→4)-α-L-rhamnopyranosyl-(1→2)-β-D-xylopyranoside (parkioside C, 3), were isolated from the n-BuOH extract of the root bark of Butyrospermum parkii, along with the known 3-O-β-D-glucopyranosyloleanolic acid (androseptoside A). The structures of the isolated compounds were established on the basis of chemical and spectroscopic methods, mainly 1D and 2D NMR data and mass spectrometry. The new compounds were tested for both radical scavenging and cytotoxic activities. Compound 2 showed cytotoxic activity against A375 and T98G cell lines, with IC(50) values of 2.74 and 2.93 μM, respectively. Furthermore, it showed an antioxidant activity comparable to that of Trolox or butylated hydroxytoluene (BHT), used as controls, against 2,2-diphenyl-1-picryl hydrazyl (DPPH), 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), oxygen and nitric oxide radicals.

摘要

从牛油果树根皮的正丁醇提取物中分离得到了三种新的三萜皂苷,分别鉴定为 3-O-β-D-吡喃葡萄糖基齐墩果酸 28-O-β-D-木吡喃糖基-(1→4)-α-L-鼠李吡喃糖基-(1→2)-β-D-木吡喃糖苷(巴戟苷 A,1)、3-O-[β-D-芹糖基-(1→3)-β-D-吡喃葡萄糖基]齐墩果酸 28-O-[β-D-芹糖基-(1→3)-β-D-木吡喃糖基-(1→4)-[α-L-鼠李吡喃糖基-(1→3)]-α-L-鼠李吡喃糖基-(1→2)β-D-木吡喃糖苷(巴戟苷 B,2)和 3-O-β-D-吡喃葡萄糖醛酸基-16α-羟基原齐墩果酸 28-O-α-L-鼠李吡喃糖基-(1→3)-β-D-木吡喃糖基-(1→4)-α-L-鼠李吡喃糖基-(1→2)-β-D-木吡喃糖苷(巴戟苷 C,3),此外还分离得到了已知的 3-O-β-D-吡喃葡萄糖基齐墩果酸(androseptoside A)。这些化合物的结构是根据化学和光谱方法,主要是 1D 和 2D NMR 数据和质谱确定的。对新化合物进行了自由基清除和细胞毒性测试。化合物 2 对 A375 和 T98G 细胞系表现出细胞毒性,IC50 值分别为 2.74 和 2.93 μM。此外,它表现出与 Trolox 或丁基化羟基甲苯(BHT)相当的抗氧化活性,用作对照,对 2,2-二苯基-1-苦基肼(DPPH)、2,2'-联氮-双(3-乙基苯并噻唑啉-6-磺酸)(ABTS)、氧自由基和一氧化氮自由基均有清除作用。

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