3-[(2S,3R,4R,5R,6S)-4,5-二羟基-6-甲基-3-[(2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基四氢吡喃-2-基]氧基-5,7-二羟基-2-(4-羟基苯基)苯并吡喃-4-酮 | 142451-65-8

• 物质功能分类: 生物化工 - 提取物
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 3-[(2S,3R,4R,5R,6S)-4,5-二羟基-6-甲基-3-[(2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基四氢吡喃-2-基]氧基-5,7-二羟基-2-(4-羟基苯基)苯并吡喃-4-酮
• 英文名称: kaempferol 3-O-(2''-O-β-D-glucopyranosyl)-α-L-rhamnopyranoside
• 英文别名: kaempferol 3-O-β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranoside；kaempferol-3-O-glucosyl-(1–2)-rhamnoside；Kaempferol-3-O-glucosyl(1-2)rhamnoside；3-[(2S,3R,4R,5R,6S)-4,5-dihydroxy-6-methyl-3-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxan-2-yl]oxy-5,7-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• CAS: 142451-65-8
• 化学式: C₂₇H₃₀O₁₅
• 分子量: 594.526
• InChiKey: BCNBWICEIXAVQF-DLVIKRKZSA-N

物化性质

• 沸点：
  945.5±65.0 °C(Predicted)
• 密度：
  1.76±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.4
• 重原子数：
  42
• 可旋转键数：
  6
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  245
• 氢给体数：
  9
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 3-[(2S,3R,4R,5R,6S)-4,5-二羟基-6-甲基-3-[(2S,3R,4S,5S,6R)-3,4,5-三羟基-6-(羟基甲基)四氢吡喃-2-基]氧基四氢吡喃-2-基]氧基-5,7-二羟基-2-(4-羟基苯基)苯并吡喃-4-酮 在 吡啶 作用下， 生成 kaempferol 3-O-(2''-O-β-D-glucopyranosyl)-α-L-rhamnopyranoside-nonaacetate
  参考文献：
  名称：

  Selective Responses of Three Ginkgo biloba Leaf-Derived Constituents on Human Intestinal Bacteria

  摘要：

  The selective responses of Ginkgo biloba leaf-derived materials against six intestinal bacteria was examined using an impregnated paper disk method and compared with that of bilobalide, ginkgolides A and B, kaempferol, and quercetin. The components of G. biloba leaves were characterized as kaempferol 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside), kaempferol 3-O-(2"-O-D-glucopyranosyl)-alpha-L-rhamnopyranoside, and quercetin 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside) by spectroscopic analysis. The growth responses varied with each bacterial strain tested. At 2 mg/disk, kaempferol 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside) and quercetin 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside) revealed potent inhibition against Clostridium perfringens, and kaempferol 3-O-(2"-O-beta-D-glucopyranosyl)-alpha-L-rhamnopyranoside showed a clear inhibitory effect on Escherichia coli. At 0.5 mg/disk, quercetin 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside) showed a strong activity against C. perfringens, but weak activity was exhibited by kaempferol 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside) against C. perfringens and kaempferol 3-O-(2"-O-beta-D-glucopyranosyl)-alpha-L-rhamnopyranoside against E coli. No inhibition was observed from treatments conducted with bilobalide, ginkgolides A and B, kaempferol, or quercetin. Furthermore, these isolated compounds did not inhibit Bifidobacterium bifidum, B. longum, B. adolescentis, or Lactobacillus acidophilus.

  DOI：

  10.1021/jf011140a

文献信息

• Selective Responses of Three <i>Ginkgo biloba</i> Leaf-Derived Constituents on Human Intestinal Bacteria
  作者：Hoi-Seon Lee、Min-Jeong Kim

  DOI：10.1021/jf011140a

  日期：2002.3.1

  The selective responses of Ginkgo biloba leaf-derived materials against six intestinal bacteria was examined using an impregnated paper disk method and compared with that of bilobalide, ginkgolides A and B, kaempferol, and quercetin. The components of G. biloba leaves were characterized as kaempferol 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside), kaempferol 3-O-(2"-O-D-glucopyranosyl)-alpha-L-rhamnopyranoside, and quercetin 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside) by spectroscopic analysis. The growth responses varied with each bacterial strain tested. At 2 mg/disk, kaempferol 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside) and quercetin 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside) revealed potent inhibition against Clostridium perfringens, and kaempferol 3-O-(2"-O-beta-D-glucopyranosyl)-alpha-L-rhamnopyranoside showed a clear inhibitory effect on Escherichia coli. At 0.5 mg/disk, quercetin 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside) showed a strong activity against C. perfringens, but weak activity was exhibited by kaempferol 3-O-alpha-(6'''-p-coumaroylglucosyl-beta-1,4-rhamnoside) against C. perfringens and kaempferol 3-O-(2"-O-beta-D-glucopyranosyl)-alpha-L-rhamnopyranoside against E coli. No inhibition was observed from treatments conducted with bilobalide, ginkgolides A and B, kaempferol, or quercetin. Furthermore, these isolated compounds did not inhibit Bifidobacterium bifidum, B. longum, B. adolescentis, or Lactobacillus acidophilus.