二水槲皮素
中文名称 | 二水槲皮素 |
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中文同义词 | 槲黄素,栎精,槲皮素;3,3′,4′,5,7-五羟基-2-苯基-1-氧杂-4-萘酮;3,5,7,3′,4′-五羟基-2-苯基苯并-4-吡喃酮;3,5,7,3′4′-五羟基黄酮;槲黄素;栎精酸;栎皮黄素;3,3′,4′,5,7-五羟-2-苯基-1-氧杂-4-萘酮 |
英文名称 | Quercetin dihydrate |
英文同义词 | QUERCETIN DIHYDRATE;3,5,7,3',4'-PENTAHYDROXYFLAVONE DIHYDRATE;3,3’,4’,5,7-pentahydroxy-flavondihydrate;Flavone,3,3’,4’,5,7-pentahydroxy-,dihydrate;2-(3,4-DIHYDROXYPHENYL)-3,5,7-TRIHYDROXY-4H-1-BENZOPYRAN-4-ONE DIHYDRATE;3,3',4',5,7-PENTAHYDROXYFLAVONE 2H2O;3,3',4',5,7-PENTAHYDROXYFLAVONE DIHYDRATE;3,3',4',5,7-PENTAHYDROXYFLAVONE HYDRATE |
CAS号 | 6151-25-3 |
分子式 | C15H14O9 |
分子量 | 338.27 |
EINECS号 | 612-158-3 |
植物来源 | 槐米 |
相关类别 | 小分子抑制剂,天然产物;医药原料;有机原料;其它杂环;植提;分析标准品;通用试剂;生化试剂;中草药成分;天然产物;植物提取物;标准品;农业和环境标准品;酮;提取物;中药;医药原料药;植物化学药;生化试剂-其他化学试剂;植物提取;医用原料;Flavanols;Biochemistry;Flavonoids;C15 to C38;Carbonyl Compounds;Ketones;Signalling;Aromatics;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Tyrosine Kinase Inhibitors;Inhibitors;TROXEPURE;抗氧化剂;原料;植物提取物单体;生物化工类;中药对照品;化工原料;通用生化试剂-天然产物;化学试剂 |
Mol文件 | 6151-25-3.mol |
结构式 |
二水槲皮素 性质
熔点 | >300 °C(lit.) |
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密度 | 1.680 g/cm3 |
储存条件 | -20°C |
溶解度 | 溶于 DMSO > 10 mM |
形态 | 黄色固体 |
色指数 | 75670 |
颜色 | 粘黄色 |
水溶解性 | practically insoluble |
Merck | 14,8034 |
BRN | 317313 |
InChIKey | GMGIWEZSKCNYSW-UHFFFAOYSA-N |
LogP | 2.075 (est) |
CAS 数据库 | 6151-25-3(CAS DataBase Reference) |
无水物分子式C15H10O7,分子量302.25,mp 316℃。二水合物分子式C15H9O7·2H2O,黄色针状结晶(稀乙醇),mp313℃~314℃ (分解)。溶于热乙醇 (1:23)、冷乙醇 (1:300),可溶于甲醇、醋酸乙酯、冰醋酸、吡啶等,不溶于石油醚、苯、乙醚、氯仿中,几乎不溶于水。槲皮素是在我国中医临床上常用的一种祛痰药,本品具有较好的祛痰、止咳效应,也有一定的平喘作用,并有降低血压、提高毛细血管抵抗力、减少毛细血管脆性、降血脂、扩张冠状动脉、增加冠状动脉血流量的药理功能。
临床槲皮素主要用于支气管炎及多痰炎症。对冠心病及高血压患者也有辅助治疗作用。用本品可有口干、头晕及胃区烧灼感,停药后可消失。
槲皮素广泛存在于被子植物中,如红管药、猫眼草、铁包金、满山红、小叶枇杷、紫花杜鹃、照山白、矮地茶、罗布麻均含有,此物系一种甙元,此种甙元常与糖结合以甙的形式存在,如槲皮苷、芦丁、金丝桃苷等。槲皮素能显著抑制促癌剂的作用、抑制离体恶性细胞的生长、抑制艾氏腹水癌细胞DNA、RNA和蛋白质合成。
槲皮素有抑制血小板聚集和5-羟色胺(5-HT)的释放作用,对ADP、凝血酶和血小板活化因子(PAF)诱导的血小板聚集均有明显抑制作用,其中对PAF的抑制作用最强,也能明显抑制凝血酶诱导的兔血小板3H-5-HT释放。
(1) 0.5mmol/L浓度槲皮素10ml/kg静滴,可显著缩短小鼠心肌缺血再灌注的心律失常持续时间,降低室颤发生率,减少缺血灌注区心肌组织中MDA含量及黄嘌呤氧化酶活性,而对SOD具明显保护作用,可能与抑制心肌中氧自由基的形成和保护心肌组织中SOD或直接清除氧自由基有关。
(2) 槲皮素与芦丁体外试验,可使粘附在兔主动脉内皮上的血小板血栓分散开,其EC50分别为80及500nmol/L。槲皮素50~500μmol/L体外试验,可提高人血小板cAMP水平,对PGI2提高人血小板cAMP水平及抑制ADP诱导的人血小板聚集,槲皮素2~50μmol/L有浓度依赖的增强作用。槲皮素在试管内300μmol/L浓度对血小板活化因子(PAF)诱导的大鼠血小板聚集,几乎可完全抑制,也抑制凝血酶及ADP诱导的血小板聚集,对凝血酶诱导的兔血小板3H-5HT的释放有抑制作用;30μmol/L浓度可明显降低大鼠血小板膜质流动性。
(3) 4×10-5~1×10-1g/ml浓度槲皮素,对卵白蛋白致敏的豚鼠肺释放组胺及SRS-A有抑制作用;1×10-5g/ml对SRS-A引起的豚鼠回肠收缩也有抑制作用。槲皮素5~50μmol/L浓度,对豚草抗原引起的人嗜碱性白细胞释放组胺有浓度依赖性的抑制作用。对卵白蛋白致敏豚鼠回肠收缩呈浓度依赖的抑制收缩,其IC50为10μmol/L。5×10-6~5×10-5mol/L,可抑制小鼠细胞毒T淋巴细胞(CTL)的增殖,也抑制ConA诱导的DNA合成。
Quercetin Dihydrate is the dihydrate preparation of Quercetin, a ubiquitous natural flavonoid with antiproliferative properties. Quercetin is described to inhibit PLA2 and PI 3-kinase (IC50 = 3.8 microM), blocking the ATP binding site of this kinase and interrupting the role of this enzyme in propagating cellular responses to growth factors. Quercetin is further described to inhibit nucleotide-dependent kinase enzymes through competition with ATP and GTP, demonstrating inhibition of pp60src phosphotransferase, tyrosine protein kinase, calcium- and phospholipid-dependent protein kinase, and cyclic GMP phosphodiesterases. Inhibition of PI 4-kinase (1-phosphatidylinositol 4-kinase) and PI-4-phosphate 5-kinase (1-phosphatidylinositol 4-phosphate 5-kinase) by Quercetin blocks the participation of these enzymes in signal transduction pathways and reduces cellular levels of the second messenger IP3 (inositol 1,4,5-trisphosphate), decreasing the release of intracellular Ca2+ stores. The antiproliferative and cytotoxic effects of Quercetin on cultured breast cancer cells are attributed to inhibition of PI 4-kinase and PI-4-phosphate 5-kinase, reduction of IP3 levels, and blockade of oncogenic growth signaling. Quercetin was shown to induce apoptosis in tumor cell lines at the G1 and S phases. Potential fatty acid synthase, PKC, and ATP5 (mitochondrial ATPase) inhibitor as well as an SIRT1 activator. SIRT1 deacetylates histones. Quercetin Dihydrate is an inhibitor of Pim-1 and an activator of GPR30.
临床槲皮素主要用于支气管炎及多痰炎症。对冠心病及高血压患者也有辅助治疗作用。用本品可有口干、头晕及胃区烧灼感,停药后可消失。
槲皮素广泛存在于被子植物中,如红管药、猫眼草、铁包金、满山红、小叶枇杷、紫花杜鹃、照山白、矮地茶、罗布麻均含有,此物系一种甙元,此种甙元常与糖结合以甙的形式存在,如槲皮苷、芦丁、金丝桃苷等。槲皮素能显著抑制促癌剂的作用、抑制离体恶性细胞的生长、抑制艾氏腹水癌细胞DNA、RNA和蛋白质合成。
槲皮素有抑制血小板聚集和5-羟色胺(5-HT)的释放作用,对ADP、凝血酶和血小板活化因子(PAF)诱导的血小板聚集均有明显抑制作用,其中对PAF的抑制作用最强,也能明显抑制凝血酶诱导的兔血小板3H-5-HT释放。
(1) 0.5mmol/L浓度槲皮素10ml/kg静滴,可显著缩短小鼠心肌缺血再灌注的心律失常持续时间,降低室颤发生率,减少缺血灌注区心肌组织中MDA含量及黄嘌呤氧化酶活性,而对SOD具明显保护作用,可能与抑制心肌中氧自由基的形成和保护心肌组织中SOD或直接清除氧自由基有关。
(2) 槲皮素与芦丁体外试验,可使粘附在兔主动脉内皮上的血小板血栓分散开,其EC50分别为80及500nmol/L。槲皮素50~500μmol/L体外试验,可提高人血小板cAMP水平,对PGI2提高人血小板cAMP水平及抑制ADP诱导的人血小板聚集,槲皮素2~50μmol/L有浓度依赖的增强作用。槲皮素在试管内300μmol/L浓度对血小板活化因子(PAF)诱导的大鼠血小板聚集,几乎可完全抑制,也抑制凝血酶及ADP诱导的血小板聚集,对凝血酶诱导的兔血小板3H-5HT的释放有抑制作用;30μmol/L浓度可明显降低大鼠血小板膜质流动性。
(3) 4×10-5~1×10-1g/ml浓度槲皮素,对卵白蛋白致敏的豚鼠肺释放组胺及SRS-A有抑制作用;1×10-5g/ml对SRS-A引起的豚鼠回肠收缩也有抑制作用。槲皮素5~50μmol/L浓度,对豚草抗原引起的人嗜碱性白细胞释放组胺有浓度依赖性的抑制作用。对卵白蛋白致敏豚鼠回肠收缩呈浓度依赖的抑制收缩,其IC50为10μmol/L。5×10-6~5×10-5mol/L,可抑制小鼠细胞毒T淋巴细胞(CTL)的增殖,也抑制ConA诱导的DNA合成。
用途
有机灵敏试剂,铝的荧光测定,铁、锡、锆的光度测定。生化试剂,线粒体腺苷三磷酸酯酶的抑制剂。医药。与表氯醇(3-氯-1,2-环氧丙烷)混合形成环氧树脂。用途
槲皮素的二水合物,是一种普遍存在的天然黄酮类化合物,具有抗增殖作用。是线粒体ATP酶和磷酸二酯酶抑制剂,也抑制PI3-激酶活性。Quercetin Dihydrate is the dihydrate preparation of Quercetin, a ubiquitous natural flavonoid with antiproliferative properties. Quercetin is described to inhibit PLA2 and PI 3-kinase (IC50 = 3.8 microM), blocking the ATP binding site of this kinase and interrupting the role of this enzyme in propagating cellular responses to growth factors. Quercetin is further described to inhibit nucleotide-dependent kinase enzymes through competition with ATP and GTP, demonstrating inhibition of pp60src phosphotransferase, tyrosine protein kinase, calcium- and phospholipid-dependent protein kinase, and cyclic GMP phosphodiesterases. Inhibition of PI 4-kinase (1-phosphatidylinositol 4-kinase) and PI-4-phosphate 5-kinase (1-phosphatidylinositol 4-phosphate 5-kinase) by Quercetin blocks the participation of these enzymes in signal transduction pathways and reduces cellular levels of the second messenger IP3 (inositol 1,4,5-trisphosphate), decreasing the release of intracellular Ca2+ stores. The antiproliferative and cytotoxic effects of Quercetin on cultured breast cancer cells are attributed to inhibition of PI 4-kinase and PI-4-phosphate 5-kinase, reduction of IP3 levels, and blockade of oncogenic growth signaling. Quercetin was shown to induce apoptosis in tumor cell lines at the G1 and S phases. Potential fatty acid synthase, PKC, and ATP5 (mitochondrial ATPase) inhibitor as well as an SIRT1 activator. SIRT1 deacetylates histones. Quercetin Dihydrate is an inhibitor of Pim-1 and an activator of GPR30.
用途
本品具有较好的祛痰、止咳作用,并有一定的平喘作用。此外还有降低血压、增强毛细血管抵抗力、减少毛细血管脆性、降血脂、扩张冠状动脉,增加冠脉血流量等作用。用于治疗慢性支气管炎。对冠心病及高血压患者也有辅助治疗作用。安全信息
危险品标志 | T |
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危险类别码 | 25-46-23/24/25 |
安全说明 | 45-53 |
危险品运输编号 | UN 2811 6.1/PG 3 |
WGK Germany | 3 |
RTECS号 | LK8950000 |
TSCA | Yes |
危险等级 | 6.1 |
包装类别 | III |
海关编码 | 29329990 |
毒性 | LD50 orally in mice: 160 mg/kg (Sullivan) |
提供商 | 语言 |
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