槲皮素

出自求聞百科
檞皮素
IUPAC名
2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
別名 櫟精
Sophoretin
Meletin
Quercetine
Xanthaurine
Quercetol
Quercitin
Quertine
Flavin meletin
識別
CAS號 117-39-5  ✓
PubChem 5280343
ChemSpider 4444051
SMILES
InChI
InChIKey REFJWTPEDVJJIY-UHFFFAOYAW
KEGG C00389
性質
化學式 C15H10O7
摩爾質量 302.236 g/mol g·mol⁻¹
精確質量 302.042653
密度 1.799 g/cm3
熔點 316 °C
若非註明，所有數據均出自一般條件（25 ℃，100 kPa）下。

檞皮素（Quercetin），也稱作五羥黃酮、檞黃酮，又稱槲皮素[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、西紅柿、西蘭花及其他綠葉蔬菜。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]及仙人掌的果實。2007年一項研究發現，有機種植的西紅柿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，包括來源於桉樹及澳洲茶樹的蜂蜜。[9][10]。

苷元

檞皮素是許多其他類黃酮苷的苷元。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

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對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]

檞皮素可減輕花粉熱的症狀。[16]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。[17][18][19]

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。[20]一個四人的試驗性臨床試驗給出的初步數據支持該觀點。[21]

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。[22][23][24]

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[25]，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。[26][27]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。[28]

通過檞皮素與超聲波結合，可抑制體外培養的皮膚癌和前列腺癌細胞。[29]

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。.[30]

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。[31]

也有學者聲稱檞皮素可降低高血壓患者的血壓[32]，及可降低肥胖者的低密度脂蛋白膽固醇的水平。[33]

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。[34]

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。[35]

《AHFS藥物信息》（2010年）[36]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。[37][38]

此外，檞皮素還被描述為CYP2C9的抑制劑[39]，及CYP3A4的抑制劑[40]和誘導劑[41]。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

  1. ↑ 國家教育研究院雙語詞彙、學術名詞暨辭書資訊網
  2. ↑ Quercetin. Merriam-Webster. 
  3. ↑ Quercitin (biochemistry). Encyclopedia Brittanica. 
  4. ↑ Christiane Fischer, Volker Speth, Sonja Fleig-Eberenz, and Gunther Neuhaus. lnduction of Zygotic Polyembryos in Wheat: lnfluence of Auxin Polar Transport (PDF). Plant Cell. 1999-10, 9 (10): 1767–1780. PMC 157020 可免費查閱. PMID 12237347. doi:10.1105/tpc.9.10.1767. 
  5. ↑ USDA Database for the Flavonoid Content of Selected Foods
  6. ↑ Crystal Smith, Kevin A. Lombard, Ellen B. Peffley, Weixin Liu. Genetic Analysis of Quercetin in Onion (Allium cepa L.) Lady Raider (PDF). The Texas Journal of Agriculture and Natural Resource (Agriculture Consortium of Texas). 2003, 16: 24–8. 
  7. ↑ Sari H. Häkkinen; et al. Content of the Flavonols Quercetin, Myricetin, and Kaempferol in 25 Edible Berries. Journal of Agricultural and Food Chemistry. 1999, 47 (6): 2274–9. PMID 10794622. doi:10.1021/jf9811065. 
  8. ↑ A. E. Mitchell, Y. J. Hong, E. Koh, D. M. Barrett, D. E. Bryant, R. F. Denison and S. Kaffka. Ten-Year Comparison of the Influence of Organic and Conventional Crop Management Practices on the Content of Flavonoids in Tomatoes. Journal of Agricultural and Food Chemistry. 2007, 55 (15): 6154–9. PMID 17590007. doi:10.1021/jf070344. 
  9. ↑ Honey Research Unit
  10. ↑ honey fingerprinting
  11. ↑ Mullen W; et al. Bioavailability of [2-(14)C]quercetin-4'-glucoside in rats. J Agric Food Chem. 2008-12, 2456 (24): 12127–37. PMID 19053221. doi:10.1021/jf802754s. 
  12. ↑ US FDA, Center for Food Safety and Nutrition, Qualified Health Claims Subject to Enforcement Discretion, April 2007 存档副本. [2011-06-30]. 
  13. ↑ Hickson, LaTonya J.; Langhi Prata, Larissa G.P.; Bobart, Shane A.; Evans, Tamara K.; Giorgadze, Nino; Hashmi, Shahrukh K.; Herrmann, Sandra M.; Jensen, Michael D.; Jia, Qingyi; Jordan, Kyra L.; Kellogg, Todd A.; Khosla, Sundeep; Koerber, Daniel M.; Lagnado, Anthony B.; Lawson, Donna K.; LeBrasseur, Nathan K.; Lerman, Lilach O.; McDonald, Kathleen M.; McKenzie, Travis J.; Passos, João F.; Pignolo, Robert J.; Pirtskhalava, Tamar; Saadiq, Ishran M.; Schaefer, Kalli K.; Textor, Stephen C.; Victorelli, Stella G.; Volkman, Tammie L.; Xue, Ailing; Wentworth, Mark A.; Wissler Gerdes, Erin O.; Zhu, Yi; Tchkonia, Tamara; Kirkland, James L. Senolytics decrease senescent cells in humans: Preliminary report from a clinical trial of Dasatinib plus Quercetin in individuals with diabetic kidney disease. EBioMedicine. 2019-09, 47: 446–456. PMC 6796530 可免費查閱. PMID 31542391. doi:10.1016/j.ebiom.2019.08.069. 
  14. ↑ 14.0 14.1 Laura K. Stewart, Jeff L. Soileau, David Ribnicky, Zhong Q. Wang, Ilya Raskin, Alexander Poulev, Martin Majewski, William T. Cefalu, and Thomas W. Gettys. Quercetin transiently increases energy expenditure but persistently decreases circulating markers of inflammation in C57BL/6J mice fed a high-fat diet. Metabolism. 2008, 57. 
  15. ↑ 15.0 15.1 15.2 J. Mark Davis, E. Angela Murphy, Martin D. Carmichael, and Ben Davis, Quercetin increases brain and muscle mitochondrial biogenesis and exercise tolerance, Am J Physiol Regul Integr Comp Physiol, 2009, 296 
  16. ↑ Balabolkin, II; Gordeeva, GF; Fuseva, ED; Dzhunelov, AB; Kalugina, OL; Khamidova, MM. Use of vitamins in allergic illnesses in children. Voprosy meditsinskoi khimii. 1992, 38 (5): 36–40. PMID 1492394. 
  17. ↑ Hirano, T; Kawai, M; Arimitsu, J; Ogawa, M; Kuwahara, Y; Hagihara, K; Shima, Y; Narazaki, M; Ogata, A. Preventative effect of a flavonoid, enzymatically modified isoquercitrin on ocular symptoms of Japanese cedar pollinosis. Allergology international : official journal of the Japanese Society of Allergology. 2009, 58 (3): 373–82. PMID 19454839. doi:10.2332/allergolint.08-OA-0070. 
  18. ↑ Kawai, M; Hirano, T; Arimitsu, J; Higa, S; Kuwahara, Y; Hagihara, K; Shima, Y; Narazaki, M; Ogata, A. Effect of enzymatically modified isoquercitrin, a flavonoid, on symptoms of Japanese cedar pollinosis: a randomized double-blind placebo-controlled trial. International archives of allergy and immunology. 2009, 149 (4): 359–68. PMID 19295240. doi:10.1159/000205582. 
  19. ↑ Mainardi, T; Kapoor, S; Bielory, L. Complementary and alternative medicine: herbs, phytochemicals and vitamins and their immunologic effects. The Journal of allergy and clinical immunology. 2009, 123 (2): 283–94; quiz 295–6. PMID 19203652. doi:10.1016/j.jaci.2008.12.023. 
  20. ↑ Papaliodis D, Boucher W, Kempuraj D, Theoharides TC. The flavonoid luteolin inhibits niacin-induced flush. Brit J Pharmacol. 2008, 153 (7): 1382–87. PMC 2437911 可免費查閱. PMID 18223672. doi:10.1038/sj.bjp.0707668. 
  21. ↑ Kalogeromitros, D; Makris, M; Chliva, C; Aggelides, X; Kempuraj, D; Theoharides, TC. A quercetin containing supplement reduces niacin-induced flush in humans. International journal of immunopathology and pharmacology. 2008, 21 (3): 509–14. PMID 18831918. 
  22. ↑ Verschoyle RD, Steward WP, Gescher AJ. Putative cancer chemopreventive agents of dietary origin-how safe are they?. Nutr Cancer. 2007, 59 (2): 152–62. PMID 18001209. doi:10.1080/01635580701458186 (不活躍 2009-06-26). 
  23. ↑ Rietjens IM, Boersma MG, van der Woude H, Jeurissen SM, Schutte ME, Alink GM. Flavonoids and alkenylbenzenes: mechanisms of mutagenic action and carcinogenic risk. Mutat. Res. 2005-07, 574 (1–2): 124–38. PMID 15914212. doi:10.1016/j.mrfmmm.2005.01.028. 
  24. ↑ van der Woude H, Alink GM, van Rossum BE; et al. Formation of transient covalent protein and DNA adducts by quercetin in cells with and without oxidative enzyme activity. Chem. Res. Toxicol. 2005-12, 18 (12): 1907–16. PMID 16359181. doi:10.1021/tx050201m. 
  25. ↑ Guidance for Industry: A Food Labeling Guide XI. Appendix C: Health Claims, 21 CFR 101.76 and 21 CFR 101.78, April 2008. US Department of Health and Human Services, Food and Drug Administration. 
  26. ↑ Neuhouser ML. Dietary flavonoids and cancer risk: evidence from human population studies. Nutr Cancer. 2004, 50 (1): 1–7. PMID 15572291. doi:10.1207/s15327914nc5001_1. 
  27. ↑ Murakami A, Ashida H, Terao J. Multitargeted cancer prevention by quercetin. Cancer Lett. 2008-10, 269 (2): 315–25. PMID 18467024. doi:10.1016/j.canlet.2008.03.046. 
  28. ↑ Nöthlings U; et al. Flavonols and pancreatic cancer risk. American Journal of Epidemiology. 2007, 166 (8): 924–931. PMID 17690219. doi:10.1093/aje/kwm172. 
  29. ↑ Paliwal S; Sundaram, J; Mitragotri, S. Induction of cancer-specific cytotoxicity towards human prostate and skin cells using quercetin and ultrasound. British Journal of Cancer. 2005, 92 (3): 499–502. PMC 2362095 可免費查閱. PMID 15685239. doi:10.1038/sj.bjc.6602364. 
  30. ↑ Davis JM, Murphy EA, Carmichael MD, Davis B. Quercetin increases brain and muscle mitochondrial biogenesis and exercise tolerance. Am J Physiol Regul Integr Comp Physiol. 2009, 296 (4): R1071–7. PMID 19211721. doi:10.1152/ajpregu.90925.2008. 
  31. ↑ Clinicaltrials.gov, National Institutes of Health
  32. ↑ Edwards RL, Lyon T, Litwin SE, Rabovsky A, Symons JD, Jalili T. Quercetin reduces blood pressure in hypertensive subjects. J. Nutr. 2007-11-01, 137 (11): 2405–11. PMID 17951477. 
  33. ↑ Egert S; et al. Quercetin reduces systolic blood pressure and plasma oxidised low-density lipoprotein concentrations in overweight subjects with a high-cardiovascular disease risk phenotype: A double-blinded, placebo-controlled cross-over study. Br J Nutr. 2009, 102 (7): 1065–1074. PMID 19402938. doi:10.1017/S0007114509359127. 
  34. ↑ Yang JY, Della-Fera MA, Rayalam S, Ambati S, Hartzell DL, Park HJ, Baile CA. Enhanced inhibition of adipogenesis and induction of apoptosis in 3T3-L1 adipocytes with combinations of resveratrol and quercetin. Life Sci. 2008, 82 (19–20): 1032–9. PMID 18433793. doi:10.1016/j.lfs.2008.03.003. 
  35. ↑ Hilliard JJ, Krause HM, Bernstein JI; et al. A comparison of active site binding of 4-quinolones and novel flavone gyrase inhibitors to DNA gyrase. Adv. Exp. Med. Biol. 1995, 390: 59–69. PMID 8718602. 
  36. ↑ 存档副本. [2011-06-22]. 
  37. ↑ Bun SS, Ciccolini J, Bun H, Aubert C, Catalin J. Drug interactions of paclitaxel metabolism in human liver microsomes. J Chemother. 2003-06, 15 (3): 266–74. PMID 12868554. 
  38. ↑ Bun SS, Giacometti S, Fanciullino R, Ciccolini J, Bun H, Aubert C. Effect of several compounds on biliary excretion of paclitaxel and its metabolites in guinea-pigs. Anticancer Drugs. 2005–07, 16 (6): 675–82. PMID 15930897. doi:10.1097/00001813-200507000-00013. 
  39. ↑ Si Dayong, Wang Y, Zhou Y-H, Guo Y, Wang J, Zhou H, Li Z-S, Fawcett JP. Mechanism of CYP2C9 inhibition by flavones and flavonols. Drug Metabolism and Disposition. 2009-03, 37 (3): 629–634. PMID 19074529. doi:10.1124/dmd.108.023416. 
  40. ↑ Su-Lan Hsiu; Yu-Chi Hou; Yao-Horng Wang; Chih-Wan Tsao; Sheng-Fang Sue; and Pei-Dawn L. Chao. Quercetin significantly decreased cyclosporin oral bioavailability in pigs and rats. Life Sciences. 2002-12-06, 72 (3): 227–235. PMID 12427482. doi:10.1016/S0024-3205(02)02235-X. 
  41. ↑ Judy L. Raucy. Regulation of CYP3A4 Expression in Human Hepatocytes by Pharmaceuticals and Natural Products. Drug Metabolism and Disposition. 2003-05-01, 31 (3): 533–539. PMID 12695340. doi:10.1124/dmd.31.5.533. 

擴展閱讀

抗氧化劑
食品的抗氧化劑
燃料的抗氧化劑
測量
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