芦丁 | 153-18-4

• 物质功能分类: 天然产物 - 黄酮类化合物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 芦丁
• 中文别名: 芸香甙；芸香苷；紫皮甙；路通；芦丁芸香苷；维生素P；紫皮甙三水合物；路丁粉；络通；芦丁三水合物；维生素P三水合物；路丁；芸香叶苷；VP
• 英文名称: rutin
• 英文别名: quercetin-3-rutinoside；quercetin-3-O-rutinoside；rutoside；quercitin-3-O-rutinoside；quercetin-3-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside；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]oxymethyl]oxan-2-yl]oxychromen-4-one；quercetin-3-O-α-rhamnopyranosyl (1'''→6'')-glucopyranoside；quercetin-3-O-β-D-glucorhamnoside；quercetin 3-O-(6-O-rhamnosylglucoside)；quercetin-3-o-rutinose；quercetin rutinoside；RUT
• CAS: 153-18-4；1340-08-5
• 化学式: C₂₇H₃₀O₁₆
• 分子量: 610.526
• InChiKey: IKGXIBQEEMLURG-NVPNHPEKSA-N

物化性质

• 熔点：
  195 °C (dec.)(lit.)
• 比旋光度：
  D23 +13.82° (ethanol); D23 -39.43° (pyridine)
• 沸点：
  576.13°C (rough estimate)
• 密度：
  1.3881 (rough estimate)
• 溶解度：
  吡啶中的溶解度为50mg/mL
• LogP：
  -2.020 (est)
• 物理描述：
  Solid
• 碰撞截面：
  232.6 Ų [M+H]+ [CCS Type: DT, Method: single field calibrated with Agilent tune mix (Agilent)]

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  43
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  266
• 氢给体数：
  10
• 氢受体数：
  16

安全信息

• 危险品标志：
  Xn,Xi
• 安全说明：
  S24/25
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2932999099
• 危险品运输编号：
  20kgs
• RTECS号：
  VM2975000
• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319

制备方法与用途

芦丁概述 来源与制法

芦丁（Rutin）是一种重要的天然黄酮类化合物。主要存在于芸香科植物芸香的全草挥发油、豆科植物槐的果实（槐角）、金丝桃科植物红旱莲的全草，鼠李科植物野梧桐的叶以及蓼科植物荞麦的籽苗中。

制法

芦丁可以从原料（如槐花蕾）经粉碎后用热乙醇萃取，再经过多次结晶精制而得到。具体的提取步骤包括浸提物浓缩后去除其他可溶性色素等不纯物，并通过多步结晶和活性炭精制获得高纯度的芦丁成品。

生理作用

芦丁具有多种生理活性：作为维生素P的一种形式，它是一种氢传递体，参与体内氧化还原酶的作用；增强维生素C的作用并促进其在体内的蓄积。此外，芦丁还能维持血管弹性、降低通透性和脆性，并抑制透明质酸酶水解，从而增强毛细血管的抵抗力。

生理活性

• 促进细胞增生，防止血细胞凝集。
• 利尿、镇咳作用。
• 抗炎和抗过敏效果。
• 降血脂、降压及保护溃疡面的作用。

化学性质与用途

芦丁难溶于冷水但可溶于热水、甲醇、乙醇以及吡啶中，并且易溶于碱性水溶液。其主要应用包括作为晶状体醛糖还原酶抑制剂、抗炎和抗病毒作用等。

详细用途

• 食用色素：具有柠檬黄色调，可用于食品着色。
• 抗氧化剂及营养补充剂：用于预防或治疗与毛细血管脆弱性相关的疾病。
• 药物：防治高血压脑出血、糖尿病视网膜病变和紫癜性疾病等。

生产方法

芦丁的生产可通过从槐花米中提取获得。具体步骤包括用热水和石灰乳煮沸，添加硼砂并保温过滤后调至pH值适宜进行结晶析出，并经过多步精制工艺得到成品。对于原料（一般为槐花蕾），也可通过乙醇萃取、乙醚、热甲醇及热水多次结晶精制的方法来获取高纯度的芦丁。

综上所述，芦丁因其独特的化学性质和广泛的应用价值，在医药及食品领域发挥着重要作用。

反应信息

• 作为反应物：
  描述：

  芦丁 在 盐酸 、 四丁基溴化铵 、 potassium carbonate 作用下， 以 乙醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-4-(benzoyloxy)-6-((5,7-bis(benzyloxy)-2-(3,4-bis(benzyloxy)phenyl)-4-oxo-4H-chromen-3-yl)oxy)tetrahydro-2H-pyran-3,5-diyl diacetate
  参考文献：
  名称：

  Synthesis of quercetin 3-O-β-d-apiofuranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)]-β-d-glucopyranoside

  摘要：

  A concise method to construct a unique 2,6-branched trisaccharide was established by regioselective glycosylation of three free hydroxyl groups on a 3-O-protected glucose moiety, and successfully used in the synthesis of quercetin 3-O-beta-D-apiofuranosyl-(1 -> 2)-[alpha-L-rhamnopyranosyl-(1 -> 6)]-beta-D-glucopyranoside, a flavonol O-glycoside isolated from glandless cotton seeds which showed notable antidepressant activities. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.04.040
• 作为产物：
  描述：

  alkaline earth salt of/the/ methylsulfuric acid 在 α-acetobromorutinose 作用下， 生成 芦丁
  参考文献：
  名称：

  Samochwalow et al., Doklady Akademii Nauk SSSR, 1958, vol. 123, p. 305

  摘要：

  DOI：
• 作为试剂：
  描述：

  反式-10-羟基去甲替林 在 human liver cytosol 芦丁 、 还原型辅酶II(NADPH)四钠盐 作用下， 反应 0.08h， 生成 (E)-N-methyl-3-(10,11-dihydro-10-oxo-5H-dibenzocycloheptene)-Δ^5,γ-propylamine
  参考文献：
  名称：

  Stereoselective reversible ketone formation from 10-hydroxylated nortriptyline metabolites in human liver

  摘要：

  1. E- and Z-10-hydroxynortriptyline are major metabolites of amitriptyline and nortriptyline in man. Upon incubation with human liver microsomes or cytosol, these metabolites were oxidized to the corresponding ketones, E- and Z-10-oxonortriptyline. (+)-E- and (+)-Z-10-hydroxynortriptyline were distinctly preferred over the (-)-isomers as substrates. NADP(+) supported the oxidation in cytosol whereas in microsomes NAD(+) was the best cofactor.2. Incubation of E- and Z-10-oxonortriptyline with NADPH and cytosol resulted in the nearly exclusive formation of (+)-E- and (+)-Z-10-hydroxynortriptyline. Kinetic analysis revealed high-affinity reduction (K-m 1-2 mu M) of the two ketones and an additional low-affinity component with the E-isomer. 10-Oxonortriptyline reduction was also catalysed by rabbit, but not by rat or guinea pig liver cytosol.3. With [4-H-3]NADPH as cosubstrate, tritium was incorporated into E- and Z-10-hydroxynortriptyline preferentially from the pro-4R position. Redox cycling of (+)-E- and (+)-Z-10-hydroxynortriptyline in cytosol in the presence of NAD(+) and NADPH was indicated by H-3 incorporation from [pro-4R-H-3]NADPH.4. Recombinant human carbonyl reductase catalysed low-affinity reduction of E-10-oxonortriptyline with preferential transfer of the pro-4S-H-3 of labelled NADPH.5. Ketone reduction in cytosol was strongly inhibited by 9,10-phenanthrenequinone and dehydrolithocholic acid and moderately by other 3-oxo steroids and some antiinflammatory drugs.6. The high-affinity reduction of E- and Z-10-oxonortriptyline and the oxidation of the alcohols in cytosol are probably mediated by a member of the aldo-keto reductase family of enzymes.

  DOI：

  10.3109/00498259509061920

文献信息

• Flavonoid derivative
  申请人：Buchholz Herwig

  公开号：US20070134172A1

  公开（公告）日：2007-06-14

  The invention relates to a novel flavonoid derivative, to an extract comprising the flavonoid derivative, to the cosmetic and pharmaceutical use thereof, to preparations comprising the flavonoid derivative or extract, and to a process for the preparation of the flavonoid derivative or extract.

  这项发明涉及一种新型黄酮衍生物，一种包含该黄酮衍生物的提取物，以及其在化妆品和药用方面的使用，包括含有该黄酮衍生物或提取物的制剂，以及一种制备该黄酮衍生物或提取物的方法。
• [EN] FIBRIN-BINDING COMPOUNDS FOR IMAGING AND TREATMENT<br/>[FR] COMPOSÉS DE LIAISON À LA FIBRINE POUR IMAGERIE ET TRAITEMENT
  申请人：COLLAGEN MEDICAL LLC

  公开号：WO2021081430A1

  公开（公告）日：2021-04-29

  This disclosure relates to compounds of Formula IV: for fibrin imaging, wherein the compounds comprise an imaging or therapeutic radioisotope.

  这项披露涉及到公式IV的化合物：用于纤维蛋白成像，其中化合物包含成像或治疗放射性同位素。
• NOVEL QUERCETIN DERIVATIVES AS ANTI-CANCER AGENTS
  申请人：Joshi Narendra Shriram

  公开号：US20110034413A1

  公开（公告）日：2011-02-10

  The present invention provides novel Quercetin derivatives of formula (I) and pharmaceutically acceptable salts, hydrates, and solvates thereof, wherein R 1 is hydrogen, benzyl or substituted benzyl; R 2 is hydrogen, benzyl or substituted benzyl, linear or branched (C 1 -C 6 ) alkyl, substituted alkyl, aryl, substituted aryl, heterocycle and substituted heterocycle, useful for treatment of various disorders including cancer, multi-drug resistant cancers, viral infections etc. The invention also provides a process for the preparation of compounds of formula (I) and pharmaceutical compositions comprising the same.

  本发明提供了新型的槲皮素衍生物及其药用可接受的盐、水合物和溶剂化物， 其中R1为氢、苄基或取代苄基；R2为氢、苄基或取代苄基，直链或支链的（C1-C6）烷基，取代烷基，芳基，取代芳基，杂环和取代杂环，用于治疗包括癌症、多药耐药癌症、病毒感染等多种疾病。本发明还提供了制备公式（I）化合物的方法以及包含该化合物的药物组合物。
• Structural Requirements of Flavonoids and Related Compounds for Aldose Reductase Inhibitory Activity.
  作者：Hisashi Matsuda、Toshio Morikawa、Iwao Toguchida、Masayuki Yoshikawa

  DOI：10.1248/cpb.50.788

  日期：——

  The methanolic extracts of several natural medicines and medicinal foodstuffs were found to show an inhibitory effect on rat lens aldose reductase. In most cases, flavonoids were isolated as the active constituents by bioassay-guided separation, and among them, quercitrin (IC50=0.15 μM), guaijaverin (0.18 μM), and desmanthin-1 (0.082 μM) exhibited potent inhibitory activity. Desmanthin-1 showed the most potent activity, which was equivalent to that of a commercial synthetic aldose reductase inhibitor, epalrestat (0.072 μM). In order to clarify the structural requirements of flavonoids for aldose reductase inhibitory activity, various flavonoids and related compounds were examined. The results suggested the following structural requirements of flavonoid: 1) the flavones and flavonols having the 7-hydroxyl and/or catechol moiety at the B ring (the 3′,4′-dihydroxyl moiety) exhibit the strong activity; 2) the 5-hydroxyl moiety does not affect the activity; 3) the 3-hydroxyl and 7-O-glucosyl moieties reduce the activity; 4) the 2–3 double bond enhances the activity; 5) the flavones and flavonols having the catechol moiety at the B ring exhibit stronger activity than those having the pyrogallol moiety (the 3′,4′,5′-trihydroxyl moiety).

  发现，几种天然药材和药用食品的甲醇提取物对大鼠晶状体醛糖还原酶显示抑制作用。在大多数情况下，通过生物测定指导的分离方法，分离得到黄酮类化合物作为活性成分，其中，槲皮苷（IC50=0.15 μM）、愈创木脂苷（0.18 μM）和去甲基芸香糖苷-1（0.082 μM）显示出强的抑制活性。去甲基芸香糖苷-1显示了最强的活性，相当于商品化合成醛糖还原酶抑制剂依帕司他（0.072 μM）的活性。为了阐明黄酮类化合物对醛糖还原酶抑制活性的结构要求，检测了各种黄酮类化合物及相关化合物。结果表明，黄酮类化合物的以下结构要求是：1）具有7-羟基和/或邻苯二酚结构的黄酮和黄酮醇（在B环上的3′,4′-二羟基结构）显示出强的活性；2）5-羟基结构并不影响活性；3）3-羟基和7-O-葡糖基结构降低活性；4）2-3双键增强活性；5）具有邻苯二酚结构的黄酮和黄酮醇显示出比具有连苯三酚结构（3′,4′,5′-三羟基结构）的化合物更强的活性。
• METHOD OF IMPROVING STABILITY OF SWEET ENHANCER AND COMPOSITION CONTAINING STABILIZED SWEET ENHANCER
  申请人：TACHDJIAN Catherine

  公开号：US20120041078A1

  公开（公告）日：2012-02-16

  The present invention includes methods of stabilizing one or more sweet enhancers when they are exposed to a light source as well as liquid compositions containing one or more sweet enhancers and one or more photostabilizers.

  本发明包括在甜味增强剂暴露于光源时稳定一个或多个甜味增强剂的方法，以及包含一个或多个甜味增强剂和一个或多个光稳定剂的液体组合物。

表征谱图