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Structure-inhibition relationship of phenylethanoid glycosides on angiotensin-converting enzyme using ultra-performance liquid chromatography-tandem quadrupole mass spectrometry

机译：使用超高效液相色谱 - 串联Quadrupole质谱法对苯乙烯糖苷对血管紧张素转换酶的结构抑制关系

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摘要

Angiotensin-converting enzyme (ACE) plays a critical role in the rennin-angiotensin system. Recently, natural products isolated from herbal medicines have demonstrated an inhibitory effect against ACE, suggesting their potential value in the regulation of blood pressure. In the present study, the ACE inhibition (ACEI) provided by 21 phenylethanoid glycosides and related phenolic compounds was investigated by measuring the production of hippuric acid (HA) using a rapid, sensitive, accurate and specific ultraperformance liquid chromatography-tandem quadrupole mass spectrometry (UPLC-MS/MS) method. The test compounds showed a wide spectrum of inhibitory potency on ACE at 50 mM, ranging from 5.29 to 95.01%, and compounds with ACEI greater than 50% were selected for IC50 determination, a measure of the effectiveness of a substance in inhibiting a specific biological function. The IC50 values ranged from 0.53 +/- 0.04 to 15.035 +/- 0.036 mM. The structure-inhibition relationships were then explored and showed that cinnamoyl groups played an essential role in the ACEI of phenylethanoid glycosides. Furthermore, the substructure of increasing ACEI in phenylethanoid glycosides involved a greater number of hydroxyl groups and less steric hindrance, allowing chelation by the active Zn2+ site of the ACE. Our results confirmed that phenylethanoid glycosides offer a widely available source of anti-hypertensive natural products. In addition, the information provided by the study of structure-inhibition relationships will assist in the further design of structurally modified phenylethanoid glycosides as anti-hypertensive drugs.
机译：血管紧张素转化酶（ACE）在肾素 - 血管紧张素系统中起着关键作用。最近，从草药中分离的天然产品已经证明了对ACE的抑制作用，表明它们在调节血压方面的潜在价值。在本研究中，通过使用快速，敏感，准确的和特定超细液相色谱 - 串联四极细质谱法测量羊毛酸（HA）的生产，研究了21种苯乙醇糖苷和相关酚类化合物提供的ACE抑制（ACEI）。 UPLC-MS / MS）方法。测试化合物在50mm处显示出宽度的抑制效力，范围为5.29至95.01％，并且选择大于50％的acei的化合物用于IC 50测定，衡量抑制特定生物学的物质的有效性功能。 IC50值范围为0.53 +/- 0.04至15.035 +/- 0.036 mm。然后探索结构抑制关系并显示肉桂酰基在苯乙酸糖苷的ACEI中起重要作用。此外，增加亚丙烷苷糖苷中aciI的亚粒子结构涉及更多的羟基和更少的空间阻断，允许施用ACE的活性Zn2 +位点螯合。我们的结果证实，苯乙醇糖苷提供了广泛可用的抗高血压天然产品来源。此外，通过研究结构抑制关系提供的信息将有助于进一步设计结构改性的苯乙醇糖苷作为抗高血压药物。

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  • 来源
    《RSC Advances》 |2015年第64期|共7页
  • 作者

    Li Pengfei; Qi Meng; Hu Haijun; Liu Qing; Yang Qiming; Wang Dandan; Guo Fujiang; Bligh S. W. Annie; Wang Zhengtao; Yang Li;

  • 作者单位

    Shanghai Univ Tradit Chinese Med MOE Key Lab Standardizat Chinese Med Inst Chinese Mat Med Shanghai 201210 Peoples R China;

    Shanghai Univ Tradit Chinese Med MOE Key Lab Standardizat Chinese Med Inst Chinese Mat Med Shanghai 201210 Peoples R China;

    Shanghai Univ Tradit Chinese Med MOE Key Lab Standardizat Chinese Med Inst Chinese Mat Med Shanghai 201210 Peoples R China;

    Shanghai Univ Tradit Chinese Med MOE Key Lab Standardizat Chinese Med Inst Chinese Mat Med Shanghai 201210 Peoples R China;

    Shanghai Univ Tradit Chinese Med MOE Key Lab Standardizat Chinese Med Inst Chinese Mat Med Shanghai 201210 Peoples R China;

    Shanghai Univ Tradit Chinese Med MOE Key Lab Standardizat Chinese Med Inst Chinese Mat Med Shanghai 201210 Peoples R China;

    Shanghai Univ Tradit Chinese Med MOE Key Lab Standardizat Chinese Med Inst Chinese Mat Med Shanghai 201210 Peoples R China;

    Univ Westminster Fac Sci &

    Technol Dept Life Sci London W1W 6UW England;

    Shanghai Univ Tradit Chinese Med MOE Key Lab Standardizat Chinese Med Inst Chinese Mat Med Shanghai 201210 Peoples R China;

    Shanghai Univ Tradit Chinese Med MOE Key Lab Standardizat Chinese Med Inst Chinese Mat Med Shanghai 201210 Peoples R China;

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