Kaempferol 3-O-α-L-rhamnopyranoside | 915778-43-7

• 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: Kaempferol 3-O-α-L-rhamnopyranoside
• 英文别名: kaempferol-3-O-α-L-rhamnopyranoside；kaempferol-3-β-rhamnopyranoside；kaempferol 3-O-α-L-rhamnoside；kaempferol 3-O-β-L-rhamnoside；kaempferol-3-O-α-L-rhamnoside；kaempferol-3-O-rhamnoside；kaempferol-3-O-alpha-L-rhamnoside；5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2R,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• CAS: 915778-43-7
• 化学式: C₂₁H₂₀O₁₀
• 分子量: 432.384
• InChiKey: SOSLMHZOJATCCP-MKMJNHTISA-N

物化性质

• 沸点：
  765.6±60.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  166
• 氢给体数：
  6
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  Kaempferol 3-O-α-L-rhamnopyranoside 在 硫酸 作用下， 以 甲醇 为溶剂， 反应 0.33h， 生成 L-鼠李糖
  参考文献：
  名称：

  Chemical constituents and antibacterial activity of Melastoma malabathricum L.

  摘要：

  The aqueous methanolic extracts of Melastoma malabathricum L. exhibited antibacterial activity when assayed against seven microorganisms by the agar diffusion method. Solvent fractionation afforded active chloroform and ethyl acetate fractions from the leaves and the flowers, respectively. A phytochemical study resulted in the identification of ursolic acid (1), 2 alpha-hydroxyursolic acid (2), asiatic acid (3), beta-sitosterol 3-O-beta-D-glucopyranoside (4) and the glycolipid glycerol 1,2-dilinolenyl-3-O-beta-D-galactopyanoside (5) from the chloroform fraction. Kaempferol (6), kaempferol 3-O-alpha-L-rhamnopyranoside (7), kaempferol 3-O-beta-D-glucopyranoside (8), kaempferol 3-O-beta-D-galactopyranoside (9), kaempferol 3-O-(2 '',6 ''-di-O-E-p-coumaryl)-beta-D-galactopyranoside (10), quercetin (11) and ellagic acid (12) were found in the ethyl acetate fraction. The structures of these compounds were determined by chemical and spectral analyses. Compounds 1-4, the flavonols (6 and 11) and ellagic acid (12) were found to be active against some of the tested microorganisms, while the kaempferol 3-O-glycosides (7-9) did not show any activity, indicating the role of the free 3-OH for antibacterial activity. Addition of p-coumaryl groups results in mild activity for 10 against Staphylococcus aureus and Bacillus cereus. Compounds 2-5, 7 and 9-12 are reported for the first time from M. malabathricum. Compound 10 is rare, being reported only once before from a plant, without assignment of the double bond geometry in the p-coumaryl moiety.

  DOI：

  10.1080/14786419.2010.538395

文献信息

• AHMED, AHMED A.;NORRIS, JOHN A.;MABRY, T. J., BIOCHEM. SYST. AND ECOL., 16,(1988) N 1, 15-16
  作者：AHMED, AHMED A.、NORRIS, JOHN A.、MABRY, T. J.

  DOI：——

  日期：——
• Chemical constituents and antibacterial activity of <i>Melastoma malabathricum </i>L.
  作者：Keng-Chong Wong、Dafaalla Mohamed Hag Ali、Peng-Lim Boey

  DOI：10.1080/14786419.2010.538395

  日期：2012.4.1

  The aqueous methanolic extracts of Melastoma malabathricum L. exhibited antibacterial activity when assayed against seven microorganisms by the agar diffusion method. Solvent fractionation afforded active chloroform and ethyl acetate fractions from the leaves and the flowers, respectively. A phytochemical study resulted in the identification of ursolic acid (1), 2 alpha-hydroxyursolic acid (2), asiatic acid (3), beta-sitosterol 3-O-beta-D-glucopyranoside (4) and the glycolipid glycerol 1,2-dilinolenyl-3-O-beta-D-galactopyanoside (5) from the chloroform fraction. Kaempferol (6), kaempferol 3-O-alpha-L-rhamnopyranoside (7), kaempferol 3-O-beta-D-glucopyranoside (8), kaempferol 3-O-beta-D-galactopyranoside (9), kaempferol 3-O-(2 '',6 ''-di-O-E-p-coumaryl)-beta-D-galactopyranoside (10), quercetin (11) and ellagic acid (12) were found in the ethyl acetate fraction. The structures of these compounds were determined by chemical and spectral analyses. Compounds 1-4, the flavonols (6 and 11) and ellagic acid (12) were found to be active against some of the tested microorganisms, while the kaempferol 3-O-glycosides (7-9) did not show any activity, indicating the role of the free 3-OH for antibacterial activity. Addition of p-coumaryl groups results in mild activity for 10 against Staphylococcus aureus and Bacillus cereus. Compounds 2-5, 7 and 9-12 are reported for the first time from M. malabathricum. Compound 10 is rare, being reported only once before from a plant, without assignment of the double bond geometry in the p-coumaryl moiety.