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首页> 外文期刊>RSC Advances >The caffeic acid moiety plays an essential role in attenuating lipid accumulation by chlorogenic acid and its analogues
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The caffeic acid moiety plays an essential role in attenuating lipid accumulation by chlorogenic acid and its analogues

机译：咖啡酸部分在通过绿原酸及其类似物中衰减脂质积累中起重要作用

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摘要

Chlorogenic acid (5-caffeoylquinic, CA) possesses distinct hypolipidemic properties in vivo and in vitro, yet the structure-activity relationship (SAR) of CA on lipid metabolism remains unknown. To achieve this aim, we designed and synthesized two sets of CA analogues and evaluated their efficacies to prevent oleic acid (OA)-elicited lipid accumulation in HepG2 cells. Blockage of all hydroxyl and carboxyl groups on the quinic acid moiety did not deteriorate the hypolipidemic effect of CA while blockage of all phenolic hydroxyl groups on the caffeic acid moiety abolished the activity of CA. Further replacement of the quinic acid moiety with cyclohexane and modification of individual phenolic hydroxyl groups on the caffeic acid moiety showed that the phenolic-hydroxyl-reserved analogues displayed a more potent hypolipidemic effect than CA, whereas the analogue with no phenolic hydroxyl displayed little effect on the OA-elicited lipid accumulation. In accordance, the modulating effects of CA on the transcription of the lipogenic gene sterol-regulatory element binding protein (SREBP)1c/1a, acetyl-CoA carboxylase (ACC), fatty acid synthase (FAS) and peroxisome proliferator-activated receptor (PPAR) were also abolished when the phenolic hydroxyl groups on the caffeic acid moiety were blocked. Our results suggest that the phenolic hydroxyl on the caffeic acid moiety is vital for the lipid-lowering activity of CA.
机译：绿原酸（5-咖啡算线，CA）具有体内和体外具有明显的低血脂性质，但在脂质代谢上的Ca的结构 - 活性关系（SAR）仍然未知。为了实现这一目标，我们设计并合成了两组CA类似物，并评估了它们的疗效，以防止油酸（OA） - 在HepG2细胞中的血脂积累。在奎尼酸部分上的所有羟基和羧基的堵塞并未恶化Ca的低血散效果，同时在咖啡酸部分上阻塞所有酚醛酸部分的堵塞废除了CA的活性。进一步替代与环己烷的奎尼酸部分和咖啡酸部分上的单个酚羟基的改性表明，酚醛羟基保留的类似物呈现比CA更有效的低血脂效果，而没有酚醛羟基的类似物效果几乎没有效果OA引发的脂质积累。根据，Ca对脂肪酸基因甾醇调节元件结合蛋白（Srebp）1c / 1a，乙酰-co.Ac，乙酰-co），脂肪酸合酶（Fas）和过氧化物体增殖物激活受体（PPAR）的转录的调节作用（PPAR当咖啡酸部分上封闭时，也被废除。我们的结果表明，咖啡酸部分上的酚羟基对于CA的脂质降低活性至关重要。

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  • 来源
    《RSC Advances》 |2019年第22期|共8页
  • 作者

    Cao Xiaoxue; Wu Chongming; Tian Yu; Guo Peng;

  • 作者单位

    Chinese Acad Med Sci Peking Union Med Coll Inst Med Plant Dev Beijing 100193 Peoples R China;

    Chinese Acad Med Sci Peking Union Med Coll Inst Med Plant Dev Beijing 100193 Peoples R China;

    Chinese Acad Med Sci Peking Union Med Coll Inst Med Plant Dev Beijing 100193 Peoples R China;

    Chinese Acad Med Sci Peking Union Med Coll Inst Med Plant Dev Beijing 100193 Peoples R China;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
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