quercetin-3-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-4′-O-β-D-glucopyranoside | 1455460-46-4

• 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-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-4′-O-β-D-glucopyranoside
• 英文别名: 4′-O-β-D-glucopyranosyl-quercetin-3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside；4'-O-β-D-glucopyranosyl-quercetin-3-O-β-D-glucopyranosyl-(1→4)-β-D-glucopyranoside；3-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]chromen-4-one
• CAS: 1455460-46-4
• 化学式: C₃₃H₄₀O₂₂
• 分子量: 788.667
• InChiKey: QTBGRFXNUTXJPX-JSXPJZBBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -3.6
• 重原子数：
  55
• 可旋转键数：
  10
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  365
• 氢给体数：
  14
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  quercetin-3-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-4′-O-β-D-glucopyranoside 在 盐酸 、 水 作用下， 反应 4.0h， 生成 D-葡萄糖
  参考文献：
  名称：

  Novel quercetin glucosides from Helminthostachys zeylanica root and acceleratory activity of melanin biosynthesis

  摘要：

  两种新型槲皮素葡萄糖苷、4′-O-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside （化合物 1）和 4′-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside （化合物 2）、从 Helminthostachys zeylanica 根 50 ；%EtOH提取物中分离得到。分离化合物的结构分析主要通过 600 MHz 和 800 MHz NMR、UPLC-TOFMS 和 GC-MS 来实现。在两种槲皮素葡萄糖苷中，化合物 1 在 10 μM 浓度下对小鼠 B16 黑色素瘤细胞具有较高的黑色素生成加速作用，是对照组的 2.7 倍，且无细胞毒性作用。

  DOI：

  10.1007/s11418-012-0672-9
• 作为产物：
  描述：

  在 palladium 10% on activated carbon 、 氢气 、 sodium methylate 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 为溶剂， 20.0 ℃ 、100.0 kPa 条件下， 反应 8.0h， 生成 quercetin-3-O-β-D-glucopyranosyl-(1 → 4)-β-D-glucopyranosyl-4′-O-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells

  摘要：

  4'-O-beta-D-Glucopyranosyl-quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material. Related compounds were also synthesized to understand the structure-activity relationships in melanin biosynthesis.Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-beta-D-glucopyranoside (1), quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.062

文献信息

• Synthesis of quercetin glycosides and their melanogenesis stimulatory activity in B16 melanoma cells
  作者：Kosei Yamauchi、Tohru Mitsunaga、Irmanida Batubara

  DOI：10.1016/j.bmc.2013.12.062

  日期：2014.2

  4'-O-beta-D-Glucopyranosyl-quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyra-noside (3) was isolated from Helminthostachys zeylanica root extract as a melanogenesis acceleration compound and was synthesized using rutin as the starting material. Related compounds were also synthesized to understand the structure-activity relationships in melanin biosynthesis.Melanogenesis activities of the glycosides were determined by measuring intracellular melanin content in B16 melanoma cells. Among the synthesized quercetin glycosides, quercetin-3-O-beta-D-glucopyranoside (1), quercetin-3-O-beta-D-glucopyranosyl-(1 -> 4)-beta-D-glucopyranoside (2), and 3 showed more potent intracellular melanogenesis acceleration activities than theophyline used as positive control in a dose-dependent manner with no cytotoxic effect. (C) 2014 Elsevier Ltd. All rights reserved.
• Novel quercetin glucosides from Helminthostachys zeylanica root and acceleratory activity of melanin biosynthesis
  作者：Kosei Yamauchi、Tohru Mitsunaga、Irmanida Batubara

  DOI：10.1007/s11418-012-0672-9

  日期：2013.4

  Two novel quercetin glucosides, namely 4′-O-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (compound 1) and 4′-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside (compound 2), were isolated from Helminthostachys zeylanica root 50 % EtOH extract. Structural analysis of isolated compounds was achieved mainly by 600 MHz and 800 MHz NMR, UPLC–TOFMS and GC–MS. Of the two quercetin glucosides, compound 1 showed a high melanogenic acceleratory effect, 2.7 times higher than control, at 10 μM concentration in murine B16 melanoma cells, with no cytotoxic effect.

  两种新型槲皮素葡萄糖苷、4′-O-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside （化合物 1）和 4′-O-β-d-glucopyranosyl-(1→2)-β-d-glucopyranosyl-quercetin-3-O-β-d-glucopyranosyl-(1→4)-β-d-glucopyranoside （化合物 2）、从 Helminthostachys zeylanica 根 50 ；%EtOH提取物中分离得到。分离化合物的结构分析主要通过 600 MHz 和 800 MHz NMR、UPLC-TOFMS 和 GC-MS 来实现。在两种槲皮素葡萄糖苷中，化合物 1 在 10 μM 浓度下对小鼠 B16 黑色素瘤细胞具有较高的黑色素生成加速作用，是对照组的 2.7 倍，且无细胞毒性作用。