大黄酚-1-O-葡萄糖苷 | 4839-60-5

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 大黄酚-1-O-葡萄糖苷
• 中文别名: 大黄酚-1-O-Beta-D-葡萄糖苷；大黄酚-1-葡萄糖苷
• 英文名称: chrysophanein
• 英文别名: Chrysophanol 1-O-beta-D-glucopyranoside；8-hydroxy-3-methyl-1-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyanthracene-9,10-dione
• CAS: 4839-60-5
• 化学式: C₂₁H₂₀O₉
• 分子量: 416.384
• InChiKey: QKPDYSSHOSPOKH-JNHRPPPUSA-N

物化性质

• 熔点：
  245-246℃
• 沸点：
  765.8±60.0 °C(Predicted)
• 密度：
  1.596±0.06 g/cm3 (20 ºC 760 Torr)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  30
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  154
• 氢给体数：
  5
• 氢受体数：
  9

制备方法与用途

生物活性方面，α-甲氧基大黄酚（Chrysophanein） 是从芦荟（Aloe hijazensis 的叶和根）中提取的大黄酚糖苷。研究表明，Chrysophanein 对几种癌细胞系表现出一定的细胞毒性作用。

反应信息

• 作为反应物：
  描述：

  大黄酚-1-O-葡萄糖苷 生成 大黄酚
  参考文献：
  名称：

  Inhibitors from Rhubarb on Lipopolysaccharide-Induced Nitric Oxide Production in Macrophages: Structural Requirements of Stilbenes for the Activity

  摘要：

  By bioassay-guided separation, three stilbenes (rhapontigenin, piceatannol, and resveratrol), two stilbene glucoside gallates (rhaponticin 2''-O-gallate and rhaponticin 6"-O-gallate), and a naphthalene glucoside (torachrysone 8-O-beta -D-glucopyranoside) with inhibitory activity against nitric oxide (NO) production in lipopolysaccharide-activated macrophages were isolated (IC50 = 11-69 muM). The oxygen functions (-OH, -OCH3) of stilbenes at the benzene ring were essential for the activity. The glucoside moiety reduced the activity, while the alpha,beta -double bond had no effect. Furthermore, the active stilbenes (rhapontigenin, piceatannol, and resveratrol) did not inhibit inducible NO synthase activity, but they inhibited nuclear factor-kappaB activation following expression of inducible NO synthase. (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0968-0896(01)00093-1

文献信息

• Metabolites from roots of Colubrina greggii var. yucatanensis and evaluation of their antiprotozoan, cytotoxic and antiproliferative activities
  作者：Dafne B Domínguez-Carmona、Fabiola Escalante-Erosa、Karlina García-Sosa、Grace Ruiz-Pinell、David Gutierrez-Yapu、Manuel J Chan-Bacab、Rosa E Moo-Puc、Nigel C Veitch、Alberto Giménez-Turba、Luis M Peña-Rodríguez

  DOI：10.1590/s0103-50532011000700013

  日期：——

  root extract of Colubrina greggii var. yucatanensis resulted in the isolation and identification of 3- O-acetyl ceanothic acid as a new natural ceanothane triterpene, together with the known metabolites ceanothic acid, cenothenic acid, betulinic acid, discarine B and chrysophanein. The natural products and the semisynthetic esters acetyl dimethyl ceanothate, dimethyl ceanothate and chrysophanein peracetate

  一个额外的净化作用。天然的尤卡坦菌的酸-3-O-乙稀类花生酸酯，天然的新三萜类化合物，代谢的juntamente com o os oscribols：酸类花生酸酯，酸类烯醛烯酸酯，酸化甜菜碱醇，迪纳菌B crisofaneina。天然的半透明酯类产品包括乙二胺二乙酸酯，乙二胺二乙酸酯和乙二胺四乙酸。Nenhum dos代谢大多数抗毒药物或抗增殖药。结果显示，抗药性抗药性在抗药性方面有所作为，而在布鲁托·德·克雷格里瓦（C. greggii var。）之外。尤卡坦州。Colubrina greggii var根提取物的纯化。尤卡坦（Yucatanensis）导致分离并鉴定出3-O-乙酰基二十碳三烯酸作为一种新的天然十六烷基三萜烯，以及已知的代谢产物十六碳三烯酸，十二碳三烯酸，桦木酸，迪卡琳B和蝶呤。天然产物和半合成酯乙酰二甲基鲸蜡酸酯，二甲基鲸蜡酸酯和过氧化chrysophanein表现出
• Inhibitors from Rhubarb on Lipopolysaccharide-Induced Nitric Oxide Production in Macrophages: Structural Requirements of Stilbenes for the Activity
  作者：Tadashi Kageura、Hisashi Matsuda、Toshio Morikawa、Iwao Toguchida、Shoichi Harima、Mamiko Oda、Masayuki Yoshikawa

  DOI：10.1016/s0968-0896(01)00093-1

  日期：2001.7

  By bioassay-guided separation, three stilbenes (rhapontigenin, piceatannol, and resveratrol), two stilbene glucoside gallates (rhaponticin 2''-O-gallate and rhaponticin 6"-O-gallate), and a naphthalene glucoside (torachrysone 8-O-beta -D-glucopyranoside) with inhibitory activity against nitric oxide (NO) production in lipopolysaccharide-activated macrophages were isolated (IC50 = 11-69 muM). The oxygen functions (-OH, -OCH3) of stilbenes at the benzene ring were essential for the activity. The glucoside moiety reduced the activity, while the alpha,beta -double bond had no effect. Furthermore, the active stilbenes (rhapontigenin, piceatannol, and resveratrol) did not inhibit inducible NO synthase activity, but they inhibited nuclear factor-kappaB activation following expression of inducible NO synthase. (C) 2001 Elsevier Science Ltd. All rights reserved.