芦丁

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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
InChI
RTECS VM2975000
DrugBank DB01698
ATC代码 C05CA01
性质
化学式 C27H30O16
摩尔质量 610.517 g/mol g·mol⁻¹
精确质量 610.153385 u
外观 固体
熔点 242 °C(515 K)
溶解性 不溶
危险性
NFPA 704
NFPA 704.svg
0
2
0
 
若非注明,所有数据均出自一般条件(25 ℃,100 kPa)下。

芦丁英语Rutin,也叫芸香苷路丁络通槲皮素-3-O-芸香糖苷)是黄酮醇槲皮素二糖芸香二糖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[编辑]

芦丁是一种存在于荞麦[2]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[3]

芦丁是一种存在于黏核桃中的主要的黄酮醇之一[4]

化学亲属[编辑]

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[5][6]

作为配体[编辑]

芦丁可以结合一些阳离子Template:Which?,以从土壤吸取营养供应植物细胞[來源請求]。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[7]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[编辑]

在小鼠[8]、大鼠 [9]、仓鼠[10]与兔子[11]以及离体研究[12]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。

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[编辑]

芦丁在猫狗乳糜胸的控制方面具有兽医用处[21]

代谢[编辑]

槲皮苷酶存在于黄曲霉[22]。它是一种存在于芦丁分解途径中的酶[23]

参考文献[编辑]

  1. ^ Lucci; Mazzafera. Rutin synthase in fava d'anta: Purification and influence of stressors. Canadian journal of plant science. 2009, 89 (5): 895–902. doi:10.4141/CJPS09001. 
  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. doi:10.1021/jf990186p. PMID 10552865. 
  3. ^ http://www.herbalextractsplus.com/rutin.cfm
  4. ^ 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
  5. ^ 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.
  6. ^ 6.0 6.1 http://www.naturalstandard.com/index-abstract.asp?create-abstract=/monographs/herbssupplements/patient-rutin.asp
  7. ^ Luo; et al.; King, Sarah M.; Chen, Yi Charlie. Inhibition of Cell Growth and VEGF Expression in Ovarian Cancer Cells by Flavonoids. Nutrition and Cancer. 2008, 60 (6): 800–9. doi:10.1080/01635580802100851. PMID 19005980. 
  8. ^ Enkhmaa; et al.; Katsube, T; Kitajima, K; Anuurad, E; Yamasaki, M; Yamane, Y. 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. 
  9. ^ Santos; et al.; Nagem, TJ; Pinto, AS; Oliveira, MG. HYPOLIPIDAEMIC EFFECTS OF NARINGENIN, RUTIN, NICOTINIC ACID AND THEIR ASSOCIATIONS. Pharmacological Research. 1999, 40 (6): 493–6. doi:10.1006/phrs.1999.0556. PMID 10660947. 
  10. ^ Auger; et al.; Gérain, Peggy; Lequeux, Nadine; Bornet, Aurélie; Serisier, Samuel; Besançon, Pierre; Caporiccio, Bertrand 等. 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. doi:10.1021/jf048177q. PMID 15769129. 
  11. ^ Juźwiak; et al.; Mokrzycki, K; Marchlewicz, M; Białecka, M; Wenda-Rózewicka, L; Gawrońska-Szklarz, B; Droździk, M. Effect of quercetin on experimental hyperlipidemia and atherosclerosis in rabbits. Pharmacol Rep. 2005, 57 (5): 604–9. PMID 16227643. 
  12. ^ Shen; et al.; Lin, HY; Huang, HC; Ko, CH; Yang, LL; Chen, YC. 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. doi:10.1016/S0014-2999(02)01792-2. PMID 12098601. 
  13. ^ Navarro-Núñez; et al.; Palomo, M.; Martínez, C.; Vicente, V.; Castillo, J.; Benavente-García, O.; Diaz-Ricart, M. 等. 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. doi:10.1021/jf0723209. PMID 18410117. 
  14. ^ Guardia; et al.; Juarez, AO; Pelzer, LE. Anti-inflammatory properties of plant flavonoids. Effects of rutin, quercetin and hesperidin on adjuvant arthritis in rat. Il Farmaco. 2001, 56 (9): 683–7. doi:10.1016/S0014-827X(01)01111-9. PMID 11680812. 
  15. ^ Chan Hun Jung; et al.; Cho, Chul Hyung; Kim, Chang Jong. 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. 
  16. ^ 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
  17. ^ 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
  18. ^ http://www.diet-and-health.net/Supplements/Rutin.html
  19. ^ 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
  20. ^ 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
  21. ^ Template:Cite pmc
  22. ^ quercitrinase on www.brenda-enzymes.org
  23. ^ 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 Template:血管保护剂