Phenolic glycosides from Sanguisorba officinalis and their anti-inflammatory effects

Phenolic glycosides from Sanguisorba officinalis and their anti-inflammatory effects
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DOI:
10.1080/14786419.2020.1849202
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发表时间:
2020-11-10
影响因子:
2.2
通讯作者:
Guo, Da-le
Guo, Da-le
中科院分区:
化学3区
文献类型:
--
作者:
Chen, Jin-feng;Tan, Lu;Guo, Da-le

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两个新的酚苷7 R,8 R-苏型-4,7,9,9 '-四羟基-3-甲氧基-8-O-4'-新木脂素-3 '-O-(3''-alpha-L-阿拉伯呋喃糖基)-beta-D-吡喃葡萄糖苷。(1),4-(4 '-羟基苯基)-2-丁酮-4''-O-(6-β-D-木糖基)-β-D-吡喃葡萄糖苷(2),沿着两种已知的相关类似物7 R,8 R-苏型-4,7,9,9 ′-四羟基-3-甲氧基-8-O-4 ′-新木脂素-3 ′-O-β-D-吡喃葡萄糖苷(3),4-(4 '-羟基苯基)-2-丁酮-4'-O-β-D-吡喃葡萄糖苷(4)是从地榆(Sanguisorba officinalis)中分离得到的。结合酸水解衍生化,通过核磁共振(NMR)、电喷雾电离高分辨质谱(HRESIMS)和圆二色谱(CD)等波谱数据,确定了这些新化合物的绝对构型。化合物1-4通过减弱炎性介质如一氧化氮(NO)以及肿瘤坏死因子-α(TNF-α)和白细胞介素-6(IL-6)的产生而在体外表现出抗炎性质。
Two new phenolic glycosides 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-(3''-alpha-L-arabinofuranosyl)-beta-D-glucopyranoside. (1), 4-(4'-hydroxyphenyl)-2-butanone-4''-O-(6-beta-D-xylosyl)-beta-D-glucopyranoside (2), along with two known related analogues 7R,8R-threo-4,7,9,9'-tetrahydroxy-3-methoxy-8-O-4'-neolignan-3'-O-beta-D-glucopyranoside (3), 4-(4'-hydroxyphenyl)-2-butanone-4'-O-beta-D-glucopyranoside (4) were obtained from the roots of Sanguisorba officinalis. Combined with acid hydrolysis derivatization, the absolute configurations of these new compounds were elucidated by comprehensive analyses of spectroscopic data including nuclear magnetic resonance (NMR), electrospray ionization high resolution mass (HRESIMS) as well as circular dichroism (CD). Compounds 1-4 exhibited anti-inflammatory properties in vitro by attenuating the production of inflammatory mediators, such as nitric oxide (NO) as well as tumor necrosis factor-alpha (TNF-alpha) and interleukin-6 (IL-6).