1'S-dihydrophayomphenol A₂ | 1358999-23-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: 1'S-dihydrophayomphenol A₂
• 英文别名: 10'S-dihydrophayomphenol A2；1'S-Dihydrophayomphenol A2；(3S,4S)-5,7-dihydroxy-3-[(1S)-1-hydroxyethyl]-4-(4-hydroxyphenyl)-3,4-dihydroisochromen-1-one
• CAS: 1358999-23-1
• 化学式: C₁₇H₁₆O₆
• 分子量: 316.31
• InChiKey: PDFTZITXJDVBHO-OCDRQSPJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1'S-dihydrophayomphenol A₂ 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 作用下， 以 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Antidiabetogenic oligostilbenoids and 3-ethyl-4-phenyl-3,4-dihydroisocoumarins from the bark of Shorea roxburghii

  摘要：

  A methanol extract of the bark of Shorea roxburghii (Dipterocarpaceae) was found to inhibit plasma glucose elevation in sucrose-loaded mice. From the extract, three new 3-ethyl-4-phenyl-3,4-dihydroisocoumarins, 1'S-dihydrophayomphenol A(2) (1) and phayomphenols B-1 (2) and B-2 (3), were isolated together with 24 known compounds including 20 stilbenoids and oligostilbenoids. The structures of 1-3 were determined on the basis of their spectroscopic properties as well as of chemical evidences. Among the isolates, (-)-hopeaphenol (6), hemsleyanol D(8), (+)-alpha-viniferin (15), and (-)-balanocarpol (18) showed inhibitory activity against plasma glucose elevation in sucrose-loaded rats at doses of 100-200 mg/kg, p.o. To clarify the mode of action of the antihyperglycemic property, effects of these oligostilbenoids on gastric emptying in mice, those on glucose uptake in isolated intestinal tissues as well as inhibitory activities against rat intestinal cx-glucosidase and rat lens aldose reductase were examined. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.11.067

文献信息

• Antidiabetogenic oligostilbenoids and 3-ethyl-4-phenyl-3,4-dihydroisocoumarins from the bark of Shorea roxburghii
  作者：Toshio Morikawa、Saowanee Chaipech、Hisashi Matsuda、Makoto Hamao、Yohei Umeda、Hiroki Sato、Haruka Tamura、Haruka Kon’i、Kiyofumi Ninomiya、Masayuki Yoshikawa、Yutana Pongpiriyadacha、Takao Hayakawa、Osamu Muraoka

  DOI：10.1016/j.bmc.2011.11.067

  日期：2012.1

  A methanol extract of the bark of Shorea roxburghii (Dipterocarpaceae) was found to inhibit plasma glucose elevation in sucrose-loaded mice. From the extract, three new 3-ethyl-4-phenyl-3,4-dihydroisocoumarins, 1'S-dihydrophayomphenol A(2) (1) and phayomphenols B-1 (2) and B-2 (3), were isolated together with 24 known compounds including 20 stilbenoids and oligostilbenoids. The structures of 1-3 were determined on the basis of their spectroscopic properties as well as of chemical evidences. Among the isolates, (-)-hopeaphenol (6), hemsleyanol D(8), (+)-alpha-viniferin (15), and (-)-balanocarpol (18) showed inhibitory activity against plasma glucose elevation in sucrose-loaded rats at doses of 100-200 mg/kg, p.o. To clarify the mode of action of the antihyperglycemic property, effects of these oligostilbenoids on gastric emptying in mice, those on glucose uptake in isolated intestinal tissues as well as inhibitory activities against rat intestinal cx-glucosidase and rat lens aldose reductase were examined. (C) 2011 Elsevier Ltd. All rights reserved.