4-hydroxyphenyl β-D-apiofuranosyl-(1->2)-O-β-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4-hydroxyphenyl β-D-apiofuranosyl-(1->2)-O-β-D-glucopyranoside
• 英文别名: seguinoside A；eriosemaside B；(2R,3S,4S,5R,6S)-5-[(2S,3R,4R)-3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy-2-(hydroxymethyl)-6-(4-hydroxyphenoxy)oxane-3,4-diol
• 化学式: C₁₇H₂₄O₁₁
• 分子量: 404.371
• InChiKey: SEZVUDWLTCREHG-FVVNKADVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  179
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 4-hydroxyphenyl β-D-apiofuranosyl-(1->2)-O-β-D-glucopyranoside 在 吡啶 作用下， 反应 13.0h， 以79%的产率得到Acetic acid (3S,4R,5S)-4-acetoxy-3-acetoxymethyl-5-[(2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(4-acetoxy-phenoxy)-tetrahydro-pyran-3-yloxy]-tetrahydro-furan-3-yl ester
  参考文献：
  名称：

  Hydroquinone glycosides from leaves of Myrsine seguinii

  摘要：

  From leaves of Myrsine seguinii, seven hydroquinone glycosides were isolated. By spectroscopic analyses, their structures were elucidated to be arbutin, arbutin 2'- and 6'-O-beta-apiofuranosides (seguinosides A and B, respectively), and the benzoyl, p-hydroxybenzoyl, 3-methoxy-4-hydroxybenzoyl and 3,5-dimethoxy-4-hydroxybenzoyl esters of the alcohol hydroxyl group on C-5 " of arbutin 2'-O-beta-apiofuranoside (seguinosides C-F, respectively). (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00384-7
• 作为产物：
  描述：

  在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 以2.2 mg的产率得到4-hydroxyphenyl β-D-apiofuranosyl-(1->2)-O-β-D-glucopyranoside
  参考文献：
  名称：

  百里香叶中的酚类化合物及其酪氨酸酶和黑色素生成抑制活性。

  摘要：

  从叶的甲醇提取物的乙酸乙酯可溶级分黑面神属巴戟，五个新的化合物（1 - 5）11种已知化合物（沿6 - 16）中分离得到。新化合物的结构通过光谱方法阐明和化合物1 - 3被发现要被酰化对苯二酚apiofuranosylglucopyranosides，而化合物4是一个酰化对苯二酚葡萄糖苷。化合物5显示为丁基p-香豆酸盐，这似乎是它与自然来源的首次隔离。测定了所有分离的化合物的酪氨酸酶抑制活性，并且该活性在对-香豆酸酯衍生物中是显着的。在体内完整的动物模型斑马鱼中，活性最高的化合物（化合物3）也抑制黑色素生成。

  DOI：

  10.1007/s11418-017-1148-8

文献信息

• Hydroquinone glycosides from leaves of Myrsine seguinii
  作者：Xi-Ning Zhong、Hideaki Otsuka、Toshinori Ide、Eiji Hirata、Anki Takushi、Yoshio Takeda

  DOI：10.1016/s0031-9422(98)00384-7

  日期：1998.12

  From leaves of Myrsine seguinii, seven hydroquinone glycosides were isolated. By spectroscopic analyses, their structures were elucidated to be arbutin, arbutin 2'- and 6'-O-beta-apiofuranosides (seguinosides A and B, respectively), and the benzoyl, p-hydroxybenzoyl, 3-methoxy-4-hydroxybenzoyl and 3,5-dimethoxy-4-hydroxybenzoyl esters of the alcohol hydroxyl group on C-5 " of arbutin 2'-O-beta-apiofuranoside (seguinosides C-F, respectively). (C) 1998 Elsevier Science Ltd. All rights reserved.
• Phenolic compounds from the leaves of Breynia officinalis and their tyrosinase and melanogenesis inhibitory activities
  作者：Ayano Sasaki、Yoshi Yamano、Sachiko Sugimoto、Hideaki Otsuka、Katsuyoshi Matsunami、Takakazu Shinzato

  DOI：10.1007/s11418-017-1148-8

  日期：2018.3

  Compound 5 was shown to be butyl p-coumarate and this seems to be its first isolation from a natural source. The tyrosinase inhibitory activity of all of the isolated compounds was assayed, and the activity was significant in p-coumarate derivatives. The most active compound, compound 3, also inhibited melanogenesis in an in vivo whole animal model, zebrafish.

  从叶的甲醇提取物的乙酸乙酯可溶级分黑面神属巴戟，五个新的化合物（1 - 5）11种已知化合物（沿6 - 16）中分离得到。新化合物的结构通过光谱方法阐明和化合物1 - 3被发现要被酰化对苯二酚apiofuranosylglucopyranosides，而化合物4是一个酰化对苯二酚葡萄糖苷。化合物5显示为丁基p-香豆酸盐，这似乎是它与自然来源的首次隔离。测定了所有分离的化合物的酪氨酸酶抑制活性，并且该活性在对-香豆酸酯衍生物中是显着的。在体内完整的动物模型斑马鱼中，活性最高的化合物（化合物3）也抑制黑色素生成。