(7S,8S)-threo-3,7,3′-trimethoxy-8-O-4′-neolignan-9′-O-β-D glucopyranoside

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物
• 英文名称: (7S,8S)-threo-3,7,3′-trimethoxy-8-O-4′-neolignan-9′-O-β-D glucopyranoside
• 英文别名: (7S,8S)-threo-3,7,3′-trimethoxy-8-O-4′-neolignan-9′-O-β-D-glucopyranoside；pinnatifidaninside A
• 化学式: C₂₇H₃₈O₁₂
• 分子量: 554.592
• InChiKey: LJYMJLRAWFPKCG-WIBXVVJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.29
• 重原子数：
  39.0
• 可旋转键数：
  14.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  176.76
• 氢给体数：
  6.0
• 氢受体数：
  12.0

反应信息

• 作为反应物：
  描述：

  (7S,8S)-threo-3,7,3′-trimethoxy-8-O-4′-neolignan-9′-O-β-D glucopyranoside 在 水 作用下， 以 三氟乙酸 为溶剂， 反应 3.0h， 生成 可得然胶
  参考文献：
  名称：

  Antioxidant and Tyrosinase Inhibitory Effects of Neolignan Glycosides from Crataegus pinnatifida Seeds

  摘要：

  In our efforts to find an inhibitor of melanin formation and develop potential depigmenting agents for skin-protecting cosmetics and medicinal products from natural resources, we focused on the seeds of Crataegus pinnatifida which showed antioxidant and tyrosinase-inhibiting activities. By activity-guided fractionation of an extract of C. pinnatifida seeds, four new neolignan glycosides, pinnatifidaninsides A-D (1-4), along with two known compounds (5-6), were isolated. Their structures were elucidated by spectroscopic analyses, especially 1D, 2D NMR and CD spectra. The antioxidant and tyrosinase-inhibiting activities of all isolates were assayed. Compound 6 showed good activity against 2,2-diphenyl-1-pikrylhydrazyl, while compounds 1, 2, 5, and 6 exhibited strong 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) free radical scavenging activity, being as effective as, or even more effective than the positive control Trolox. Moreover, compounds 5 and 6 displayed a moderate mushroom tyrosinase inhibitory activity.

  DOI：

  10.1055/s-0034-1383253

文献信息

• Antioxidant and Tyrosinase Inhibitory Effects of Neolignan Glycosides from Crataegus pinnatifida Seeds
  作者：Xiao-Xiao Huang、Qing-Bo Liu、Jie Wu、Li-Hong Yu、Qian Cong、Yan Zhang、Li-Li Lou、Ling-Zhi Li、Shao-Jiang Song

  DOI：10.1055/s-0034-1383253

  日期：——

  In our efforts to find an inhibitor of melanin formation and develop potential depigmenting agents for skin-protecting cosmetics and medicinal products from natural resources, we focused on the seeds of Crataegus pinnatifida which showed antioxidant and tyrosinase-inhibiting activities. By activity-guided fractionation of an extract of C. pinnatifida seeds, four new neolignan glycosides, pinnatifidaninsides A-D (1-4), along with two known compounds (5-6), were isolated. Their structures were elucidated by spectroscopic analyses, especially 1D, 2D NMR and CD spectra. The antioxidant and tyrosinase-inhibiting activities of all isolates were assayed. Compound 6 showed good activity against 2,2-diphenyl-1-pikrylhydrazyl, while compounds 1, 2, 5, and 6 exhibited strong 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) free radical scavenging activity, being as effective as, or even more effective than the positive control Trolox. Moreover, compounds 5 and 6 displayed a moderate mushroom tyrosinase inhibitory activity.