芦丁

芦丁
	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
别名	络通; 芸香苷; 路丁
识别
CAS号	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
性质
化学式	C27H30O16
摩尔质量	610.517 g·mol⁻¹
外观	固体
熔点	242 °C（515 K）
溶解性（水）	不溶
药理学
ATC代码	C05CA01（C05）
危险性
NFPA 704	0 2 0
	若非注明，所有数据均出自标准状态（25 ℃，100 kPa）下。

芦丁（英语：Rutin，也叫芸香苷、路丁、络通或槲皮素-3-O-芸香糖苷）是黄酮醇槲皮素与二糖芸香二糖（α-L-鼠李吡喃糖基-(1→6))-β-D-葡萄吡喃糖）之间形成的糖苷。在巴西芸香（Dimorphandra mollis）中，芦丁的合成是经过芦丁合酶的活性而完成的^[1]。

发现

芦丁是一种存在于荞麦^[2]（普通荞麦 Fagopyrum esculentum及鞑靼荞麦 Fagopyrum tataricum）^[3]、大黄的叶子和叶柄以及芦笋中的柑橘属黄酮类化合物糖苷。芦丁亦存在于巴西芸香树的果实中、塔状树的果实和花中、水果和果皮中（特别是柑橘类水果（橘子、柚子、柠檬和酸橙））以及如桑葚、灰树果实以及越橘等浆果中。芦丁的名字来自于芸香（Ruta graveolens），后者是一种亦含有芦丁的植物。芦丁有时候被称为是维生素P，尽管它不是严格意义上的维生素^[4]。

芦丁是一种存在于黏核桃中的主要的黄酮醇之一^[5]。

化学亲属

芦丁（槲皮素芸香糖苷），与槲皮苷一样，是一种黄酮类化合物槲皮素的糖苷。就其本身说，他们的化学结构式是非常相似的，然而所携带的羟基并不一样。槲皮素和芦丁两者都被多国作为提供血管保护的用药，且是多种多维生素制剂与草药疗法的成分。芦丁存在于多种植物，特别是蓼科的荞麦中^[6]^[7]。

作为配体

芦丁可以结合一些阳离子^{[哪个／哪些？]}，以从土壤吸取营养供应植物细胞^{[来源请求]}。在人体中，它可以结合二价铁离子（Fe²⁺），从而防止它与过氧化氢相结合，否则后者可能会产生高反应性的自由基，而自由基会损伤细胞。芦丁也是一种抗氧化剂。

此外，在体外中显示出芦丁可以将血管内皮生长因子^[8]抑制在低毒性浓度下，因此它可以作为一种血管发生抑制剂。这一结果可潜在地被用于相关癌症的控制上。

健康效应

在小鼠^[9]、大鼠 ^[10]、仓鼠^[11]与兔子^[12]以及离体研究^[13]中得到了芦丁与槲皮素效果的证据，并无临床研究表明芦丁作为一种膳食补充品在人体中有的显著的且良好的效果。

芦丁抑制血小板凝集^[14]，同时减少毛细血管的通透性，使得血液更稀薄些且能促进循环^{[来源请求]}。
芦丁在某些动物与离体模型中显示出抗炎性^[15]^[16]。
芦丁抑制醛糖还原酶的活性^{[来源请求]}。醛糖还原酶是一种通常存在于眼睛与人体其他部位的酶，这种酶使得葡萄糖转化为山梨醇这种糖醇。
芦丁也会强化毛细血管^{[来源请求]}，故因此也会缓解血友病的症状。它也会帮助阻止常见的、不好看的腿部静脉水肿；然而，对含有芦丁的荞麦茶功效的一项双盲临床研究并未显示出高于安慰剂组的显著效果^[17]。
芦丁，就像阿魏酸一样，可以减少被氧化的低密度脂蛋白所造成的细胞毒性，且会降低心脏病的风险^{[来源请求]}。
有一些证据显示芦丁可以被用来治疗血友病、静脉曲张以及微血管病^[7]。
芦丁也是一种抗氧化剂^[18]；相较于槲皮素、金合欢素、桑色素、高车前素、橘皮苷与柚皮苷来说，它被认为是最强的^[19]。然而，在其他实验中，芦丁的效果相对于槲皮素的来说是较少或微乎其微的^[20]^[21]。

羟乙基芦丁，是芦丁的一种合成的羟乙基酰化产物，被用于下肢静脉功能不全的治疗。

兽医

芦丁在猫狗乳糜胸的控制方面具有兽医用处^[22]。

代谢

槲皮苷酶存在于黄曲霉中^[23]。它是一种存在于芦丁分解途径中的酶^[24]。

外部链接

芦丁 Rutin （页面存档备份，存于互联网档案馆）中草药化学图像数据库 (香港浸会大学中医药学院) （中文）（英文）

参考文献

^ 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. （原始内容存档于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.
^ 廖宜伦; 陈裕星; 林云康; 陈镮斌. 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). 台湾行政院农业委员会台中区农业改良场. : 87–96 [2016-08-03]. （原始内容 (PDF)存档于2016年8月15日）（中文（繁体））.
^ 存档副本. [2017-04-04]. （原始内容存档于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]. （原始内容存档于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. ^{[永久失效链接]}
^ 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^{[永久失效链接]}
^ 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 （页面存档备份，存于互联网档案馆）
^ 存档副本. [2012-01-25]. （原始内容存档于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 （页面存档备份，存于互联网档案馆）
^ 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]. （原始内容存档于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:黄酮醇

[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. （原始内容存档于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] 廖宜伦; 陈裕星; 林云康; 陈镮斌. 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). 台湾行政院农业委员会台中区农业改良场. : 87–96 [2016-08-03]. （原始内容 (PDF)存档于2016年8月15日）（中文（繁体））.

[4] 存档副本. [2017-04-04]. （原始内容存档于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]. （原始内容存档于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. ^{[永久失效链接]}

[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^{[永久失效链接]}

[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 （页面存档备份，存于互联网档案馆）

[19] 存档副本. [2012-01-25]. （原始内容存档于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 （页面存档备份，存于互联网档案馆）

[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]. （原始内容存档于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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