kaempferol-3-O-(3,4-di-O-acetyl-α-L-rhamnopyranoside) | 1266714-86-6

• 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-(3,4-di-O-acetyl-α-L-rhamnopyranoside)
• 英文别名: SL0101；[(2R,3R,4R,5S,6R)-4-acetyloxy-6-[5,7-dihydroxy-2-(4-hydroxyphenyl)-4-oxochromen-3-yl]oxy-5-hydroxy-2-methyloxan-3-yl] acetate
• CAS: 1266714-86-6
• 化学式: C₂₅H₂₄O₁₂
• 分子量: 516.458
• InChiKey: SXOZSDJHGMAEGZ-PATWHGEKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  37
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  178
• 氢给体数：
  4
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  kaempferol-3-O-(3,4-di-O-acetyl-α-L-rhamnopyranoside) 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以90%的产率得到afzelin
  参考文献：
  名称：

  Studies on α-glucosidase, aldose reductase and glycation inhibitory properties of sesquiterpenes and flavonoids ofZingiber zerumbetSmith

  摘要：

  Eight known phytochemicals, four sesquiterpenes and four flavonoids of Zingiber zerumbet were screened against alpha-glucosidase enzyme, aldose reductase enzyme and antiglycation property under in vitro conditions. The results established kaempferol-3-O-methylether as a potent inhibitor of alpha-glucosidase enzyme with an IC50 value of 7.88 mu M. In aldose reductase enzyme inhibition assay, all the compounds except zerumbone epoxide showed good to excellent inhibition properties. Among these, the flavonoid compounds were found to be potent aldose reductase inhibitors compared with the four sesquiterpenes. In addition, compounds such as alpha-humulene, kaempferol, kaempferol-3-O-methylether and 3 '',4 ''-O-diacetylafzelin displayed potent antiglycation properties. From overall results, we found that kaempferol and kaempferol-3-O-methylether are potent inhibitors of alpha-glucosidase enzyme, aldose reductase enzyme and glycation reaction, the three main targets of drugs for the treatment of diabetes and its complications.

  DOI：

  10.1080/14786419.2014.956741

文献信息

• SYNTHESIS AND IDENTIFICATION OF NOVEL RSK-SPECIFIC INHIBITORS
  申请人：Hecht Sidney M.

  公开号：US20120245112A1

  公开（公告）日：2012-09-27

  A composition comprising an SL0101 [kaempferol 3-O-(3″,4″-di-O-acetyl-α-L-rhamnopyranoside)] derivative compound that has enhanced ability to inhibit RSK activity, relative to the parent compound is provided. The compounds have utility for treating any disease or conditions characterized or associated with excess or undesirable RSK activity. For example the RSK inhibitors of the present invention can be used to reduce the proliferation of neoplastic cells or for inhibiting the establishment or maintenance of an intracellular pathogenic infection by pathogens whose pathogenicity derives in part from the pathogen's ability to impede endosomal/phagosomal maturation in the host cell.
• US9040673B2
  申请人：——

  公开号：US9040673B2

  公开（公告）日：2015-05-26
• [EN] SYNTHESIS AND IDENTIFICATION OF NOVEL RSK-SPECIFIC INHIBITORS<br/>[FR] SYNTHÈSE ET IDENTIFICATION DE NOUVEAUX INHIBITEURS SPÉCIFIQUES DE LA RSK
  申请人：HECHT SIDNEY M

  公开号：WO2011019995A2

  公开（公告）日：2011-02-17

  A composition comprising an SL0101 [kaempferol 3-O-(3",4"-di-O-acetyl-α-L- rhamnopyranoside)] derivative compound that has enhanced ability to inhibit RSK activity, relative to the parent compound is provided. The compounds have utility for treating any disease or conditions characterized or associated with excess or undesirable RSK activity. For example the RSK inhibitors of the present invention can be used to reduce the proliferation of neoplastic cells or for inhibiting the establishment or maintenance of an intracellular pathogenic infection by pathogens whose pathogenicity derives in part from the pathogen's ability to impede endosomal/phagosomal maturation in the host cell.