Paviosides A-H, eight new oleane type saponins from Aesculus pavia with cytotoxic activity
Paviosides A-H, eight new oleane type saponins from Aesculus pavia with cytotoxic activity
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DOI：
10.1016/j.bmc.2012.03.048
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发表时间：
2012-05-15
影响因子：
3.5
通讯作者：
Curir, Paolo
中科院分区：
文献类型：
--
作者：
Lanzotti, Virginia;Termolino, Pasquale;Curir, Paolo
对红花七叶树（Aesculus pavia）进行植物化学分析，分离出了8种新的三萜皂苷，它们基于齐墩果烷型骨架，被命名为七叶皂苷A - H（1a、1b - 4a、4b）。根据化学、二维核磁共振以及质谱数据，新化合物的结构被阐明如下：3 - O - [β - D - 吡喃木糖基(1→2)] [-β - D - 吡喃葡萄糖基(1→4)] - β - D - 吡喃葡萄糖醛酸21 - 惕各酰基 - 22 - 乙酰基玉蕊醇C（1a），3 - O - [β - D - 吡喃木糖基(1→2)] [-β - D - 吡喃葡萄糖基(1→4)] - β - D - 吡喃葡萄糖醛酸21 - 当归酰基 - 22 - 乙酰基玉蕊醇C（1b），3 - O - [β - D - 吡喃木糖基(1→2)] [-β - D - 吡喃半乳糖基(1→4)] - β - D - 吡喃葡萄糖醛酸21 - 惕各酰基 - 22 - 乙酰基玉蕊醇C（2a），3 - O - [β - D - 吡喃木糖基(1→2)] [-β - D - 吡喃半乳糖基(1→4)] - β - D - 吡喃葡萄糖醛酸21 - 当归酰基 - 22 - 乙酰基玉蕊醇C（2b），3 - O - [β - D - 吡喃木糖基(1→2)] [-β - D - 吡喃木糖基(1→4)] - β - D - 吡喃葡萄糖醛酸21 - 惕各酰基 - 22 - 乙酰基玉蕊醇C（3a），3 - O - [β - D - 吡喃木糖基(1→2)] [-β - D - 吡喃木糖基(1→4)] - β - D - 吡喃葡萄糖醛酸21 - 当归酰基 - 22 - 乙酰基玉蕊醇C（3b），3 - O - [β - D - 吡喃木糖基(1→2)] [-β - D - 吡喃木糖基(1→4)] - β - D - 吡喃葡萄糖醛酸21 - 惕各酰基 - 22 - 乙酰基原七叶皂苷元（4a），以及3 - O - [β - D - 吡喃木糖基(1→2)] [-β - D - 吡喃木糖基(1→4)] - β - D - 吡喃葡萄糖醛酸21 - 当归酰基 - 22 - 乙酰基原七叶皂苷元（4b）。这些化合物对J - 774（小鼠单核细胞/巨噬细胞）和WEHI - 164（小鼠纤维肉瘤）细胞系显示出细胞毒活性。其中，七叶皂苷E - H（3a、3b和4a、4b）显示出较高的活性，其活性值范围为2.1至3.6μg/mL。构效关系研究表明，木糖单元取代葡萄糖对活性有积极影响，而当葡萄糖被半乳糖取代时观察到有少许不利影响。苷元结构以及在C - 21位存在惕各酰基或当归酰基对两种受试细胞系的抑制活性没有显著影响。（C）2012爱思唯尔有限公司。保留所有权利。
A phytochemical analysis of Aesculus pavia has led to the isolation of eight novel triterpenoid saponins, based on oleane type skeleton and named paviosides A-H (1a, 1b-4a, 4b). On the basis of chemical, and 2D NMR and mass spectrometry data, the structures of the new compounds were elucidated as 3-O-[beta-D-xylopyranosyl(1 -> 2)] [-beta-D-glucopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (1a), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-glucopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (1b), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-galactopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (2a), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-galactopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (2b), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl barringtogenol C (3a), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl barringtogenol C (3b), 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-tigloyl-22-acetyl protoaescigenin (4a), and 3-O-[beta-D-xylopyranosyl (1 -> 2)] [-beta-D-xylopyranosyl (1 -> 4)]-beta-D-glucopyranosiduronic acid 21-angeloyl-22-acetyl protoaescigenin (4b). The compounds showed cytotoxic activity on J-774, murinemonocyte/macrophage, and WEHI-164, murine fibrosarcoma, cell lines. Among them, paviosides E-H (3a, 3b and 4a, 4b) showed higher activity with values ranging from 2.1 to 3.6 mu g/mL. Structure-activity relationship studies indicated the positive effect on the activity of xylose unit in the place of glucose, while a little detrimental effect is observed when glucose is substituted by galactose. The aglycone structure and the presence of a tigloyl or an angeloyl group at C-21 do not affect significantly the inhibitory activity on both tested cell lines. (C) 2012 Elsevier Ltd. All rights reserved.