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槲皮素

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檞皮素
IUPAC名
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
别名 栎精
五羥黃酮
檞黃酮
识别
CAS号 117-39-5  checkY
PubChem 5280343
ChemSpider 4444051
SMILES
 
  • O=C1c3c(O/C(=C1/O)c2ccc(O)c(O)c2)cc(O)cc3O
InChI
 
  • 1/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H
InChIKey REFJWTPEDVJJIY-UHFFFAOYAW
KEGG C00389
性质
化学式 C15H10O7
摩尔质量 302.236 g·mol⁻¹
密度 1.799 g/cm3
熔点 316 °C
若非注明,所有数据均出自标准状态(25 ℃,100 kPa)下。

檞皮素(quercetin)又稱五羥黃酮檞黃酮,又稱栎精[1],是一種植物性黃酮醇,屬於多酚中的黃酮類化合物,存在于水果、蔬菜和谷物等植物中。

檞皮素广泛存在于自然界中。其英文名“quercetin”最早出现于1857年,其来源于“quercetum”,意为栎树林[2][3]其是一种天然的生长素极性运输抑制剂。[4]

檞皮素含量丰富的食品包括:茶叶(茶树;2000-2500 mg/kg),刺山柑(1800 mg/kg)[5]欧当归(1700 mg/kg),苹果(44 mg/kg),红洋葱(1910 mg/kg,最外层的含量最高[6]),红葡萄柑橘蕃茄花椰菜及其他綠葉蔬菜。此外還有许多浆果的含量也较高,包括覆盆子歐洲越橘(158 mg/kg,鲜重),越橘(种植74 mg/kg,野生146 mg/kg),蔓越莓(种植83 mg/kg,野生121 mg/kg),沙棘(62 mg/kg),岩高兰(种植53 mg/kg,野生56 mg/kg)[7]仙人掌的果实。2007年一项研究发现,有机种植的番茄檞皮素含量比传统种植的高出79%。[8]

澳大利亚昆士兰大学的一项研究表明,部分品种的蜂蜜中也存在檞皮素,包括来源于桉树澳洲茶樹的蜂蜜。[9][10]

苷元

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檞皮素是许多其他类黄酮苷苷元。槲皮素与鼠李糖结合形成檞皮苷;与芸香糖结合形成芦丁;与阿拉伯糖结合形成番石榴苷;与乳糖结合形成金丝桃苷

生理活性

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大鼠生物利用度的研究显示,当放射性同位素标记的槲皮素-4-葡萄糖苷通过胃肠道后,其被转化为酚酸[11]

檞皮素既尚未被科学的证明其具有任何疗效,也没有得到任何监管机构的批准。美国食品与药品管理局尚未批准任何关于槲皮素的功效说明。[12]不過达沙替尼和槲皮素的混合物也一種潛在的返老藥(Senolytic),一項人體初步臨床試驗顯示,达沙替尼和槲皮素的混合物在患有糖尿病腎臟病變的人類患者中,確實會降低部分組織當中衰老細胞的數量。[13]

炎症

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一些实验室的研究表明槲皮素可能具有抗炎特性[14][15],并在研究其潜在的疗效。[15][16]

檞皮素可减轻花粉热的症状。[17]其一种酶改性衍生物被发现具有减轻花粉热眼部症状的作用。[18][19][20]

一项对老鼠的研究表明,槲皮素能有效的减少速释型烟酸引起的潮紅現象,部分途径为减少前列腺素D2的产生。[21]一个四人的试验性临床试验给出的初步数据支持该观点。[22]

癌症

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实验室体外细胞研究显示,檞皮素也可转变为致癌物,但这项研究并没有报告其会增加动物或人类的患癌风险。[23][24][25]

美国癌症协会说道,虽然檞皮素“已被选为对许多包括癌症的疾病有效的物质”,并且“一些早期的实验结果显示其具有开发前景,但现在还没有可靠的临床证据说明檞皮素可以预防或治疗人类癌症。”充足的水果和蔬菜的摄入可能降低患癌症的风险[26],槲皮素是许多可能的作用源之一受到研究。

在动物实验中,檞皮素被推测有可能降低患某些癌症的风险。[27][28]一项时长8年的研究发现,三种黄酮类化合物——山柰酚、檞皮素和杨梅素——可降低吸烟者患胰腺癌的风险。[29]

通过檞皮素与超声波结合,可抑制体外培养的皮肤癌前列腺癌细胞。[30]

代谢

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檞皮素已被证明可增加大鼠的能量代谢,但仅限于短期(短于8周)。[14]檞皮素对小鼠运动耐受性的影响与增加线粒体生物合成有关。[15]小鼠口服12.5至25 mg/kg浓度依次增加的檞皮素,可增加线粒体生物标志物的基因表达,并可改善运动耐受性。.[31]

已有有关于檞皮素对结节病哮喘、肥胖与糖尿病的葡萄糖吸收的安全性和有效性的初步研究。[32]

也有学者声称檞皮素可降低高血压患者的血压[33],及可降低肥胖者的低密度脂蛋白胆固醇的水平。[34]

体外研究表明檞皮素和白藜芦醇联合应用可抑制脂肪细胞的产生。[35]

药物相互作用

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檞皮素有一些抗生素配伍禁忌;其可能影响氟喹诺酮的作用,因檞皮素也具有竞争结合DNA旋转酶的能力。尚未确定其是否能抑制或增强氟奎诺酮的效果。[36]

《AHFS药物信息》(2010年)[37]将檞皮素标记为CYP2C8的抑制剂,并具体的说明其与紫杉醇可能形成有害的相互作用。由于紫杉醇由CYP2C8代谢,其生物利用度可能增加或不可预测,可能导致毒副作用[38][39]

此外,檞皮素还被描述为CYP2C9的抑制剂[40],及CYP3A4的抑制剂[41]和诱导剂[42]。CYP2C9和CPY3A4都是细胞色素P450混合功能氧化酶系统的组分,因此这些酶参与外来物质的代谢。

参考文献

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