蘆丁

蘆丁
	IUPAC名; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-({[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}methyl)oxan-2-yl]oxy4H-chromen-4-one
別名	絡通; 芸香苷; 路丁
識別
CAS號	153-18-4
PubChem	5280805
ChemSpider	4444362
SMILES	CC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC3=C(OC4=CC(=CC(=C4C3=O)O)O)C5=CC(=C(C=C5)O)O)O)O)O)O)O)O;
InChI	1S/C27H30O16/c1-8-17(32)20(35)22(37)26(40-8)39-7-15-18(33)21(36)23(38)27(42-15)43-25-19(34)16-13(31)5-10(28)6-14(16)41-24(25)9-2-3-11(29)12(30)4-9/h2-6,8,15,17-18,20-23,26-33,35-38H,7H2,1H3/t8-;
RTECS	VM2975000
DrugBank	DB01698
性質
化學式	C27H30O16
摩爾質量	610.517 g·mol⁻¹
外觀	固體
熔點	242 °C（515 K）
溶解性（水）	不溶
藥理學
ATC代碼	C05CA01（C05）
危險性
NFPA 704	0 2 0
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

蘆丁（英語：Rutin，也叫芸香苷、路丁、絡通或槲皮素-3-O-芸香糖苷）是黃酮醇槲皮素與二糖芸香二糖（α-L-鼠李吡喃糖基-(1→6))-β-D-葡萄吡喃糖）之間形成的糖苷。在巴西芸香（Dimorphandra mollis）中，蘆丁的合成是經過蘆丁合酶的活性而完成的^[1]。

發現

蘆丁是一種存在於蕎麥^[2]（普通蕎麥 Fagopyrum esculentum及韃靼蕎麥 Fagopyrum tataricum）^[3]、大黃的葉子和葉柄以及蘆筍中的柑橘屬黃酮類化合物糖苷。蘆丁亦存在於巴西芸香樹的果實中、塔狀樹的果實和花中、水果和果皮中（特別是柑橘類水果（橘子、柚子、檸檬和酸橙））以及如桑葚、灰樹果實以及越橘等漿果中。蘆丁的名字來自於芸香（Ruta graveolens），後者是一種亦含有蘆丁的植物。蘆丁有時候被稱為是維生素P，儘管它不是嚴格意義上的維生素^[4]。

蘆丁是一種存在於黏核桃中的主要的黃酮醇之一^[5]。

化學親屬

蘆丁（槲皮素芸香糖苷），與槲皮苷一樣，是一種黃酮類化合物槲皮素的糖苷。就其本身說，他們的化學結構式是非常相似的，然而所攜帶的羥基並不一樣。槲皮素和蘆丁兩者都被多國作為提供血管保護的用藥，且是多種多維生素製劑與草藥療法的成分。蘆丁存在於多種植物，特別是蓼科的蕎麥中^[6]^[7]。

作為配體

蘆丁可以結合一些陽離子^{[哪個／哪些？]}，以從土壤吸取營養供應植物細胞^{[來源請求]}。在人體中，它可以結合二價鐵離子（Fe²⁺），從而防止它與過氧化氫相結合，否則後者可能會產生高反應性的自由基，而自由基會損傷細胞。蘆丁也是一種抗氧化劑。

此外，在體外中顯示出蘆丁可以將血管內皮生長因子^[8]抑制在低毒性濃度下，因此它可以作為一種血管發生抑制劑。這一結果可潛在地被用於相關癌症的控制上。

健康效應

在小鼠^[9]、大鼠 ^[10]、倉鼠^[11]與兔子^[12]以及離體研究^[13]中得到了蘆丁與槲皮素效果的證據，並無臨床研究表明蘆丁作為一種膳食補充品在人體中有的顯著的且良好的效果。

蘆丁抑制血小板凝集^[14]，同時減少毛細血管的通透性，使得血液更稀薄些且能促進循環^{[來源請求]}。
蘆丁在某些動物與離體模型中顯示出抗炎性^[15]^[16]。
蘆丁抑制醛糖還原酶的活性^{[來源請求]}。醛糖還原酶是一種通常存在於眼睛與人體其他部位的酶，這種酶使得葡萄糖轉化為山梨醇這種糖醇。
蘆丁也會強化毛細血管^{[來源請求]}，故因此也會緩解血友病的症狀。它也會幫助阻止常見的、不好看的腿部靜脈水腫；然而，對含有蘆丁的蕎麥茶功效的一項雙盲臨床研究並未顯示出高於安慰劑組的顯著效果^[17]。
蘆丁，就像阿魏酸一樣，可以減少被氧化的低密度脂蛋白所造成的細胞毒性，且會降低心臟病的風險^{[來源請求]}。
有一些證據顯示蘆丁可以被用來治療血友病、靜脈曲張以及微血管病^[7]。
蘆丁也是一種抗氧化劑^[18]；相較於槲皮素、金合歡素、桑色素、高車前素、橘皮苷與柚皮苷來說，它被認為是最強的^[19]。然而，在其他實驗中，蘆丁的效果相對於槲皮素的來說是較少或微乎其微的^[20]^[21]。

羥乙基蘆丁，是蘆丁的一種合成的羥乙基酰化產物，被用於下肢靜脈功能不全的治療。

獸醫

蘆丁在貓狗乳糜胸的控制方面具有獸醫用處^[22]。

代謝

槲皮苷酶存在於黃麴黴中^[23]。它是一種存在於蘆丁分解途徑中的酶^[24]。

外部連結

蘆丁 Rutin （頁面存檔備份，存於互聯網檔案館）中草藥化學圖像數據庫 (香港浸會大學中醫藥學院) （中文）（英文）

參考文獻

^ Lucci; Mazzafera. Rutin synthase in fava d'anta: Purification and influence of stressors. Canadian journal of plant science. 2009, 89 (5): 895–902 [2012-04-02]. doi:10.4141/CJPS09001. （原始內容存檔於2012-09-04）.
^ Kreft S, Knapp M, Kreft I. Extraction of rutin from buckwheat (Fagopyrum esculentum Moench) seeds and determination by capillary electrophoresis. J. Agric. Food Chem. November 1999, 47 (11): 4649–52. PMID 10552865. doi:10.1021/jf990186p.
^ 廖宜倫; 陳裕星; 林雲康; 陳鐶斌. 蕎麥芸香苷之研究. 台中區農業改良場一○一年專題討論專集 (PDF). 台灣行政院農業委員會臺中區農業改良場. : 87–96 [2016-08-03]. （原始內容 (PDF)存檔於2016年8月15日）（中文（繁體））.
^ 存档副本. [2017-04-04]. （原始內容存檔於2012-06-08）.
^ Low-Density Lipoprotein Antioxidant Activity of Phenolic Compounds and Polyphenol Oxidase Activity in Selected Clingstone Peach Cultivars. Susan Chang, Christine Tan, Edwin N. Frankel and Diane M. Barrett, J. Agric. Food Chem., 2000, 48, pages 147−151, doi:10.1021/jf990456
^ Kreft S, Knapp M, Kreft I. Extraction of rutin from buckwheat (Fagopyrum esculentum Moench) seeds and determination by capillary electrophoresis. J Agric Food Chem 1999 ; 47 (11):4649–4652.
^ ^7.0 ^7.1 存档副本. [2022-03-04]. （原始內容存檔於2013-04-01）.
^ Luo; King, Sarah M.; Chen, Yi Charlie; et al. Inhibition of Cell Growth and VEGF Expression in Ovarian Cancer Cells by Flavonoids. Nutrition and Cancer. 2008, 60 (6): 800–9. PMID 19005980. doi:10.1080/01635580802100851.
^ Enkhmaa; Katsube, T; Kitajima, K; Anuurad, E; Yamasaki, M; Yamane, Y; et al. Mulberry (Morus alba L.) leaves and their major flavonol quercetin 3-(6-malonylglucoside) attenuate atherosclerotic lesion development in LDL receptor-deficient mice. J Nutr. 2005, 135 (4): 729–34. PMID 15795425.
^ Santos; Nagem, TJ; Pinto, AS; Oliveira, MG; et al. HYPOLIPIDAEMIC EFFECTS OF NARINGENIN, RUTIN, NICOTINIC ACID AND THEIR ASSOCIATIONS. Pharmacological Research. 1999, 40 (6): 493–6. PMID 10660947. doi:10.1006/phrs.1999.0556.
^ Auger; Gérain, Peggy; Lequeux, Nadine; Bornet, Aurélie; Serisier, Samuel; Besançon, Pierre; Caporiccio, Bertrand; Cristol, Jean-Paul; et al. Dietary wine phenolics catechin, quercetin, and resveratrol efficiently protect hypercholesterolemic hamsters against aortic fatty streak accumulation. J Agric Food Chem. 2005, 53 (6): 2015–21. PMID 15769129. doi:10.1021/jf048177q.
^ Juźwiak; Mokrzycki, K; Marchlewicz, M; Białecka, M; Wenda-Rózewicka, L; Gawrońska-Szklarz, B; Droździk, M; et al. Effect of quercetin on experimental hyperlipidemia and atherosclerosis in rabbits. Pharmacol Rep. 2005, 57 (5): 604–9. PMID 16227643.
^ Shen; Lin, HY; Huang, HC; Ko, CH; Yang, LL; Chen, YC; et al. In vitro and in vivo inhibitory activities of rutin, wogonin, and quercetin on lipopolysaccharide-induced nitric oxide and prostaglandin E2 production. European Journal of Pharmacology. 2002, 446 (1–3): 187–94. PMID 12098601. doi:10.1016/S0014-2999(02)01792-2.
^ Navarro-Núñez; Palomo, M.; Martínez, C.; Vicente, V.; Castillo, J.; Benavente-García, O.; Diaz-Ricart, M.; Escolar, G.; et al. Apigenin Inhibits Platelet Adhesion and Thrombus Formation and Synergizes with Aspirin in the Suppression of the Arachidonic Acid Pathway. J. Agric. Food Chem. 2008, 56 (9): 2970–6. PMID 18410117. doi:10.1021/jf0723209.
^ Guardia; Juarez, AO; Pelzer, LE; et al. Anti-inflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjuvant arthritis in rat. Il Farmaco. 2001, 56 (9): 683–7. PMID 11680812. doi:10.1016/S0014-827X(01)01111-9.
^ Chan Hun Jung; Cho, Chul Hyung; Kim, Chang Jong; et al. Anti-asthmatic action of quercetin and rutin in conscious guinea-pigs challenged with aerosolized ovalbumin. Arch. Pharmacal Research. 2007, 30 (12): 1599–1607. doi:10.1007/BF02977330. ^{[永久失效連結]}
^ Ihme et al. "Leg oedema protection from a buckwheat herb tea in patients with chronic venous insufficiency: a single-centre, randomised, double-blind, placebo-controlled clinical trial", European Journal of Clinical Pharmacology, 50(6):443-447, doi:10.1007/s002280050138^{[永久失效連結]}
^ Metodiewa et al. "Evidence for antiradical and antioxidant properties of four biologically active N,N-Diethylaminoethyl ethers of flavaone oximes: A comparison with natural polyphenolic flavonoid rutin action", IUBMB Life 1997, 41(5):1067–1075, doi:10.1080/15216549700202141 （頁面存檔備份，存於互聯網檔案館）
^ 存档副本. [2012-01-25]. （原始內容存檔於2011-12-27）.
^ Bando et al. "Ingested quercetin but not rutin increases accumulation of hepatic β-carotene in BALB/c mice" Mol. Nutr. Food Res. 54(S2):S261-7 doi:10.1002/mnfr.200900329 （頁面存檔備份，存於互聯網檔案館）
^ Chow et al. "Quercetin, but not rutin and quercitrin, prevention of H2O2-induced apoptosis via anti-oxidant activity and heme oxygenase 1 gene expression in macrophages", Biochemical Pharmacology 2005, 69(12):1839-1851, doi:10.1016/j.bcp.2005.03.017
^ Template:Cite pmc
^ quercitrinase on www.brenda-enzymes.org. [2012-04-02]. （原始內容存檔於2012-10-21）.
^ The rutin catabolic pathway with special emphasis on quercetinase. Sylvain Tranchimand, Pierre Brouant and Gilles Iacazio, Biodegradation, Volume 21, Number 6, pages 833-859, doi:10.1007/s10532-010-9359-7

Template:黃酮醇

[1] Lucci; Mazzafera. Rutin synthase in fava d'anta: Purification and influence of stressors. Canadian journal of plant science. 2009, 89 (5): 895–902 [2012-04-02]. doi:10.4141/CJPS09001. （原始內容存檔於2012-09-04）.

[2] Kreft S, Knapp M, Kreft I. Extraction of rutin from buckwheat (Fagopyrum esculentum Moench) seeds and determination by capillary electrophoresis. J. Agric. Food Chem. November 1999, 47 (11): 4649–52. PMID 10552865. doi:10.1021/jf990186p.

[tdais-3] 廖宜倫; 陳裕星; 林雲康; 陳鐶斌. 蕎麥芸香苷之研究. 台中區農業改良場一○一年專題討論專集 (PDF). 台灣行政院農業委員會臺中區農業改良場. : 87–96 [2016-08-03]. （原始內容 (PDF)存檔於2016年8月15日）（中文（繁體））.

[4] 存档副本. [2017-04-04]. （原始內容存檔於2012-06-08）.

[Chang-5] Low-Density Lipoprotein Antioxidant Activity of Phenolic Compounds and Polyphenol Oxidase Activity in Selected Clingstone Peach Cultivars. Susan Chang, Christine Tan, Edwin N. Frankel and Diane M. Barrett, J. Agric. Food Chem., 2000, 48, pages 147−151, doi:10.1021/jf990456

[6] Kreft S, Knapp M, Kreft I. Extraction of rutin from buckwheat (Fagopyrum esculentum Moench) seeds and determination by capillary electrophoresis. J Agric Food Chem 1999 ; 47 (11):4649–4652.

[naturalstandard-7] 7.0 ^7.1 存档副本. [2022-03-04]. （原始內容存檔於2013-04-01）.

[8] Luo; King, Sarah M.; Chen, Yi Charlie; et al. Inhibition of Cell Growth and VEGF Expression in Ovarian Cancer Cells by Flavonoids. Nutrition and Cancer. 2008, 60 (6): 800–9. PMID 19005980. doi:10.1080/01635580802100851.

[9] Enkhmaa; Katsube, T; Kitajima, K; Anuurad, E; Yamasaki, M; Yamane, Y; et al. Mulberry (Morus alba L.) leaves and their major flavonol quercetin 3-(6-malonylglucoside) attenuate atherosclerotic lesion development in LDL receptor-deficient mice. J Nutr. 2005, 135 (4): 729–34. PMID 15795425.

[10] Santos; Nagem, TJ; Pinto, AS; Oliveira, MG; et al. HYPOLIPIDAEMIC EFFECTS OF NARINGENIN, RUTIN, NICOTINIC ACID AND THEIR ASSOCIATIONS. Pharmacological Research. 1999, 40 (6): 493–6. PMID 10660947. doi:10.1006/phrs.1999.0556.

[11] Auger; Gérain, Peggy; Lequeux, Nadine; Bornet, Aurélie; Serisier, Samuel; Besançon, Pierre; Caporiccio, Bertrand; Cristol, Jean-Paul; et al. Dietary wine phenolics catechin, quercetin, and resveratrol efficiently protect hypercholesterolemic hamsters against aortic fatty streak accumulation. J Agric Food Chem. 2005, 53 (6): 2015–21. PMID 15769129. doi:10.1021/jf048177q.

[12] Juźwiak; Mokrzycki, K; Marchlewicz, M; Białecka, M; Wenda-Rózewicka, L; Gawrońska-Szklarz, B; Droździk, M; et al. Effect of quercetin on experimental hyperlipidemia and atherosclerosis in rabbits. Pharmacol Rep. 2005, 57 (5): 604–9. PMID 16227643.

[13] Shen; Lin, HY; Huang, HC; Ko, CH; Yang, LL; Chen, YC; et al. In vitro and in vivo inhibitory activities of rutin, wogonin, and quercetin on lipopolysaccharide-induced nitric oxide and prostaglandin E2 production. European Journal of Pharmacology. 2002, 446 (1–3): 187–94. PMID 12098601. doi:10.1016/S0014-2999(02)01792-2.

[14] Navarro-Núñez; Palomo, M.; Martínez, C.; Vicente, V.; Castillo, J.; Benavente-García, O.; Diaz-Ricart, M.; Escolar, G.; et al. Apigenin Inhibits Platelet Adhesion and Thrombus Formation and Synergizes with Aspirin in the Suppression of the Arachidonic Acid Pathway. J. Agric. Food Chem. 2008, 56 (9): 2970–6. PMID 18410117. doi:10.1021/jf0723209.

[15] Guardia; Juarez, AO; Pelzer, LE; et al. Anti-inflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjuvant arthritis in rat. Il Farmaco. 2001, 56 (9): 683–7. PMID 11680812. doi:10.1016/S0014-827X(01)01111-9.

[16] Chan Hun Jung; Cho, Chul Hyung; Kim, Chang Jong; et al. Anti-asthmatic action of quercetin and rutin in conscious guinea-pigs challenged with aerosolized ovalbumin. Arch. Pharmacal Research. 2007, 30 (12): 1599–1607. doi:10.1007/BF02977330. ^{[永久失效連結]}

[17] Ihme et al. "Leg oedema protection from a buckwheat herb tea in patients with chronic venous insufficiency: a single-centre, randomised, double-blind, placebo-controlled clinical trial", European Journal of Clinical Pharmacology, 50(6):443-447, doi:10.1007/s002280050138^{[永久失效連結]}

[18] Metodiewa et al. "Evidence for antiradical and antioxidant properties of four biologically active N,N-Diethylaminoethyl ethers of flavaone oximes: A comparison with natural polyphenolic flavonoid rutin action", IUBMB Life 1997, 41(5):1067–1075, doi:10.1080/15216549700202141 （頁面存檔備份，存於互聯網檔案館）

[19] 存档副本. [2012-01-25]. （原始內容存檔於2011-12-27）.

[20] Bando et al. "Ingested quercetin but not rutin increases accumulation of hepatic β-carotene in BALB/c mice" Mol. Nutr. Food Res. 54(S2):S261-7 doi:10.1002/mnfr.200900329 （頁面存檔備份，存於互聯網檔案館）

[21] Chow et al. "Quercetin, but not rutin and quercitrin, prevention of H2O2-induced apoptosis via anti-oxidant activity and heme oxygenase 1 gene expression in macrophages", Biochemical Pharmacology 2005, 69(12):1839-1851, doi:10.1016/j.bcp.2005.03.017

[22] Template:Cite pmc

[23] quercitrinase on www.brenda-enzymes.org. [2012-04-02]. （原始內容存檔於2012-10-21）.

[24] The rutin catabolic pathway with special emphasis on quercetinase. Sylvain Tranchimand, Pierre Brouant and Gilles Iacazio, Biodegradation, Volume 21, Number 6, pages 833-859, doi:10.1007/s10532-010-9359-7

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