quercetin-3'-O-methyl-3-O-α-L-rhamnopyranosyl(1->6)-β-D-glucopyranoside

• 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: quercetin-3'-O-methyl-3-O-α-L-rhamnopyranosyl(1->6)-β-D-glucopyranoside
• 英文别名: tamarixetin 3-O-α-L-rhamnopyranosyl-(1'''->6'')-β-D-glucopyranoside；isorhamnetin 3-O-rutinoside；isorhamnetin-3-O-rutinoside；tamarixetin 3-O-rutinoside；tamarixetin-3-O-rutinoside；isorhamnetin 3-rutinoside；5,7-Dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-3-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-((((2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one；5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-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
• 化学式: C₂₈H₃₂O₁₆
• 分子量: 624.552
• InChiKey: KEIZXGINFPDITQ-GEBJFKNCSA-N

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：

  硫酸二甲酯 、 芦丁 在 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 rhamnetin 3-O-rutinoside 、 quercetin-3'-O-methyl-3-O-α-L-rhamnopyranosyl(1->6)-β-D-glucopyranoside 、 7,4′-di-O-methylquercetin-3-O-beta-rutinoside
  参考文献：
  名称：

  Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2014.04.053

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.