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[虎杖变种柳叶蓼中的两种新肉桂酸蔗糖酯]

[Two new sucrose cinnamates from Polygonum lapathifolium var. salicifolium].

作者信息

Chen Zhi-Hua, Wang Guo-En, Jiang Ren-Wang

机构信息

Guangzhou Baiyunshan Guanghua Pharmaceutical Co.,Ltd. Guangzhou 510285,China Institute of Traditional Chinese Medicine and Natural Products,Jinan University Guangzhou 510632,China.

Institute of Traditional Chinese Medicine and Natural Products,Jinan University Guangzhou 510632,China.

出版信息

Zhongguo Zhong Yao Za Zhi. 2021 Feb;46(4):944-950. doi: 10.19540/j.cnki.cjcmm.20200717.201.

Abstract

Two new sucrose cinnamates(1 and 2) along with nine known compounds(3-11) were isolated from ethanol extract of Polygonum lapathifolium var. salicifolium by silica gel column chromatography, ODS column chromatography and semi-preparative HPLC. Their structures were elucidated by extensive spectroscopic methods including 1 D-and 2 D-NMR experiments, as well as HR-ESI-MS analysis. Eleven compounds(7 sucrose cinnamates, 3 phenylpropanoids and 1 lactone) were obtained and their structures were identified as(1,3-O-di-p-coumaroyl)-β-D-fructofuranosyl-(2→1)-α-D-glucopyranoside(1),(1,3-O-di-p-coumaroyl)-β-D-fructofuranosyl-(2→1)-(6-O-acetyl)-α-D-glucopyranoside(2),(3-O-feruloyl)-β-D-fructofuranosyl-(2→1)-(6-O-p-coumaroyl)-α-D-glucopyranoside(3), hydropiperoside(4), vanicoside C(5),(1,3-O-di-p-coumaroyl)-β-D-fructofuranosyl-(2→1)-(6-O-feruloyl)-α-D-glucopyranoside(6), vanicoside B(7),trans-p-hydroxycinnamic acid methyl ester(8), trans-p-hydroxycinnamic acid ethyl ester(9), methyl ferulate(10) and dimethoxydimethylphthalide(11), respectively. Compounds 1 and 2 were two new sucrose cinnamates, and compounds 1-11 were isolated from this plant for the first time. The antioxidant activities of the isolated compounds 1-9 were investigated by an oxygen radical absorbance capacity(ORAC) assay, and all nine compounds were found to show strong antioxidant activities. Among them, compound 6(10 μmol·L(-1)) was the supreme one in antioxidant activities, with its ORAC value equivalent to(1.60±0.05) times of 50 μmol·L(-1) Trolox.

摘要

通过硅胶柱色谱、ODS柱色谱和半制备HPLC,从柳叶刺蓼乙醇提取物中分离得到两种新的蔗糖肉桂酸酯(1和2)以及9种已知化合物(3 - 11)。通过包括一维和二维核磁共振实验以及高分辨电喷雾电离质谱分析在内的多种光谱方法对其结构进行了鉴定。共获得11种化合物(7种蔗糖肉桂酸酯、3种苯丙素类化合物和1种内酯),其结构分别鉴定为(1,3 - O - 二对香豆酰基) - β - D - 呋喃果糖基 - (2→1) - α - D - 吡喃葡萄糖苷(1)、(1,3 - O - 二对香豆酰基) - β - D - 呋喃果糖基 - (2→1) - (6 - O - 乙酰基) - α - D - 吡喃葡萄糖苷(2)、(3 - O - 阿魏酰基) - β - D - 呋喃果糖基 - (2→1) - (6 - O - 对香豆酰基) - α - D - 吡喃葡萄糖苷(3)、水蓼苷(4)、香草糖苷C(5)、(1,3 - O - 二对香豆酰基) - β - D - 呋喃果糖基 - (2→1) - (6 - O - 阿魏酰基) - α - D - 吡喃葡萄糖苷(6)、香草糖苷B(7)、反式对羟基肉桂酸甲酯(8)、反式对羟基肉桂酸乙酯(9)、阿魏酸甲酯(10)和二甲氧基二甲基邻苯二甲酸酯(11)。化合物1和2为两种新的蔗糖肉桂酸酯,化合物1 - 11均为首次从该植物中分离得到。采用氧自由基吸收能力(ORAC)分析法对分离得到的化合物1 - 9的抗氧化活性进行了研究,发现所有9种化合物均表现出较强的抗氧化活性。其中,化合物6(10 μmol·L⁻¹)的抗氧化活性最强,其ORAC值相当于50 μmol·L⁻¹ Trolox的(1.60±0.05)倍。

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