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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
別名 櫟精
五羥黃酮
檞黃酮
識別
CAS號 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
性質
化學式 C15H10O7
摩爾質量 302.236 g·mol⁻¹
密度 1.799 g/cm3
熔點 316 °C
若非註明,所有數據均出自標準狀態(25 ℃,100 kPa)下。

檞皮素(quercetin)又稱五羥黃酮檞黃酮,又稱櫟精[1],是一種植物性黃酮醇,屬於多酚中的黃酮類化合物,存在於水果、蔬菜和穀物等植物中。

檞皮素廣泛存在於自然界中。其英文名「quercetin」最早出現於1857年,其來源於「quercetum」,意為櫟樹林[2][3]其是一種天然的生長素極性運輸抑制劑。[4]

檞皮素含量豐富的食品包括:茶葉(茶樹;2000-2500 mg/kg),刺山柑(1800 mg/kg)[5]歐當歸(1700 mg/kg),蘋果(44 mg/kg),紅洋蔥(1910 mg/kg,最外層的含量最高[6]),紅葡萄柑橘蕃茄花椰菜及其他綠葉蔬菜。此外還有許多漿果的含量也較高,包括覆盆子歐洲越橘(158 mg/kg,鮮重),越橘(種植74 mg/kg,野生146 mg/kg),蔓越莓(種植83 mg/kg,野生121 mg/kg),沙棘(62 mg/kg),岩高蘭(種植53 mg/kg,野生56 mg/kg)[7]仙人掌的果實。2007年一項研究發現,有機種植的番茄檞皮素含量比傳統種植的高出79%。[8]

澳大利亞昆士蘭大學的一項研究表明,部分品種的蜂蜜中也存在檞皮素,包括來源於桉樹澳洲茶樹的蜂蜜。[9][10]

苷元

檞皮素是許多其他類黃酮苷苷元。槲皮素與鼠李糖結合形成檞皮苷;與芸香糖結合形成蘆丁;與阿拉伯糖結合形成番石榴苷;與乳糖結合形成金絲桃苷

生理活性

大鼠生物利用度的研究顯示,當放射性同位素標記的槲皮素-4-葡萄糖苷通過胃腸道後,其被轉化為酚酸[11]

檞皮素既尚未被科學的證明其具有任何療效,也沒有得到任何監管機構的批准。美國食品與藥品管理局尚未批准任何關於槲皮素的功效說明。[12]不過達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,達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

一些實驗室的研究表明槲皮素可能具有抗炎特性[14][15],並在研究其潛在的療效。[15][16]

檞皮素可減輕花粉熱的症狀。[17]其一種酶改性衍生物被發現具有減輕花粉熱眼部症狀的作用。[18][19][20]

一項對老鼠的研究表明,槲皮素能有效的減少速釋型煙酸引起的潮紅現象,部分途徑為減少前列腺素D2的產生。[21]一個四人的試驗性臨床試驗給出的初步數據支持該觀點。[22]

癌症

實驗室體外細胞研究顯示,檞皮素也可轉變為致癌物,但這項研究並沒有報告其會增加動物或人類的患癌風險。[23][24][25]

美國癌症協會說道,雖然檞皮素「已被選為對許多包括癌症的疾病有效的物質」,並且「一些早期的實驗結果顯示其具有開發前景,但現在還沒有可靠的臨床證據說明檞皮素可以預防或治療人類癌症。」充足的水果和蔬菜的攝入可能降低患癌症的風險[26],槲皮素是許多可能的作用源之一受到研究。

在動物實驗中,檞皮素被推測有可能降低患某些癌症的風險。[27][28]一項時長8年的研究發現,三種黃酮類化合物——山柰酚、檞皮素和楊梅素——可降低吸煙者患胰腺癌的風險。[29]

通過檞皮素與超聲波結合,可抑制體外培養的皮膚癌前列腺癌細胞。[30]

代謝

檞皮素已被證明可增加大鼠的能量代謝,但僅限於短期(短於8周)。[14]檞皮素對小鼠運動耐受性的影響與增加線粒體生物合成有關。[15]小鼠口服12.5至25 mg/kg濃度依次增加的檞皮素,可增加線粒體生物標誌物的基因表達,並可改善運動耐受性。.[31]

已有有關於檞皮素對結節病哮喘、肥胖與糖尿病的葡萄糖吸收的安全性和有效性的初步研究。[32]

也有學者聲稱檞皮素可降低高血壓患者的血壓[33],及可降低肥胖者的低密度脂蛋白膽固醇的水平。[34]

體外研究表明檞皮素和白藜蘆醇聯合應用可抑制脂肪細胞的產生。[35]

藥物相互作用

檞皮素有一些抗生素配伍禁忌;其可能影響氟喹諾酮的作用,因檞皮素也具有競爭結合DNA旋轉酶的能力。尚未確定其是否能抑制或增強氟奎諾酮的效果。[36]

《AHFS藥物信息》(2010年)[37]將檞皮素標記為CYP2C8的抑制劑,並具體的說明其與紫杉醇可能形成有害的相互作用。由於紫杉醇由CYP2C8代謝,其生物利用度可能增加或不可預測,可能導致毒副作用[38][39]

此外,檞皮素還被描述為CYP2C9的抑制劑[40],及CYP3A4的抑制劑[41]和誘導劑[42]。CYP2C9和CPY3A4都是細胞色素P450混合功能氧化酶系統的組分,因此這些酶參與外來物質的代謝。

參考文獻

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