rhamnetin 3-O-rutinoside | 34202-83-0

• 物质功能分类: 生物化工 - 核苷类药物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: rhamnetin 3-O-rutinoside
• 英文别名: rhamnetin-3-O-rutinoside；rhamnetin 3-O-Rut；7-O-Methylrutin；2-(3,4-dihydroxyphenyl)-5-hydroxy-7-methoxy-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
• CAS: 34202-83-0
• 化学式: C₂₈H₃₂O₁₆
• 分子量: 624.552
• InChiKey: LVRWOUXRNRBDNV-GEBJFKNCSA-N

物化性质

• 沸点：
  973.6±65.0 °C(Predicted)
• 密度：
  1.74±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  44
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  255
• 氢给体数：
  9
• 氢受体数：
  16

反应信息

• 作为产物：
  描述：

  重氮甲烷 、 芦丁 以 甲醇 、 乙醚 为溶剂， 反应 1.0h， 以33%的产率得到2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxy-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
  参考文献：
  名称：

  Structural Requirements of Flavonoids and Related Compounds for Aldose Reductase Inhibitory Activity.

  摘要：

  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。

  DOI：

  10.1248/cpb.50.788

文献信息

• Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK
  作者：Kosei Yamauchi、Tohru Mitsunaga、Mizuho Inagaki、Tohru Suzuki

  DOI：10.1016/j.bmc.2014.04.053

  日期：2014.7

  In order to understand the effect of structure-activity relationships on melanogenesis using B16 melanoma cells, 19 quercetin derivatives were synthesized. Among the synthesized compounds, 3-O-methylquercetin (11) and 3',4',7-O-trimethylquercetin (14) increased melanin content more potently than the positive control theophylline, while exhibiting low cytotoxicity. Compound 11 exhibited less melanogenesis-stimulating activity than compound 14. However, 11 increased the expression of tyrosinase and tyrosinase-related protein 1 (TRP-1) to a greater extent than 14, thereby suggesting that melanogenesis in melanoma cells does not depend solely on the expression of the enzymes catalyzing melanin biosynthesis. Furthermore, 14 also stimulated the expression of the microphthalmia-associated transcription factor (MITF) and p-p38 mitogen activated protein kinase (MAPK), while they were not increased by 11. These results suggest that 11 may enhance the expression of tyrosinase and TRP-1 by regulating the proteasomal degradation of melanogenic enzymes and/or by activating other transcriptional factors regulating enzyme expression. (C) 2014 Elsevier Ltd. All rights reserved.
• 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。