afzelin

• 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: afzelin
• 英文别名: kaempferol 3-O-α-d-rhamnoside；kaempferol 3‐O‐α‐L‐rhamnoside；5,7-dihydroxy-2-(4-hydroxyphenyl)-3-((2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one；5,7-dihydroxy-2-(4-hydroxyphenyl)-3-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
• 化学式: C₂₁H₂₀O₁₀
• 分子量: 432.384
• InChiKey: SOSLMHZOJATCCP-QBWVUYDZSA-N

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：

  afzelin 、 碘甲烷 在 盐酸 、 silver(l) oxide 作用下， 生成 5,7,4'-三甲氧基山柰酚
  参考文献：
  名称：

  Two flavonol glycosides from Chenopodium ambrosioides

  摘要：

  DOI：

  10.1016/0031-9422(90)85389-w
• 作为产物：
  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

• Bio-active antioxidants from plant foods for nutraceutical product development
  申请人：Choudhary M. Iqbal

  公开号：US10005809B2

  公开（公告）日：2018-06-26

  The present invention relates to 5-O-[6″-(3-hydroxy-3-methyl glutarate)β-D-glucoside as a new antioxidant.

  本发明涉及作为新型抗氧化剂的 5-O-[6″-（3-羟基-3-甲基戊二酸）β-D-葡萄糖苷。
• BIO-ACTIVE ANTIOXIDANTS FROM PLANT FOODS FOR NUTRACEUTICAL PRODUCT DEVELOPMENT
  申请人：Choudhary M. Iqbal

  公开号：US20140221634A1

  公开（公告）日：2014-08-07

  The present invention relates to 5-O-[ 6 ″-( 3 -hydroxy- 3 methyl glutarate)β-D-glucodise as a new antioxidant.