5a-(3,4-Dihydroxy-phenyl)-1,3,11a-trihydroxy-12-oxo-11a,12-dihydro-5aH-5,6,11-trioxa-naphthacene-8-carboxylic acid

• 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: 5a-(3,4-Dihydroxy-phenyl)-1,3,11a-trihydroxy-12-oxo-11a,12-dihydro-5aH-5,6,11-trioxa-naphthacene-8-carboxylic acid
• 英文别名: 5a-(3,4-Dihydroxyphenyl)-1,3,11a-trihydroxy-12-oxochromeno[2,3-b][1,4]benzodioxine-8-carboxylic acid；5a-(3,4-dihydroxyphenyl)-1,3,11a-trihydroxy-12-oxochromeno[2,3-b][1,4]benzodioxine-8-carboxylic acid
• 化学式: C₂₂H₁₄O₁₁
• 分子量: 454.347
• InChiKey: YDISVBSZBHIFEQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  33
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  183
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  5a-(3,4-Dihydroxy-phenyl)-1,3,11a-trihydroxy-12-oxo-11a,12-dihydro-5aH-5,6,11-trioxa-naphthacene-8-carboxylic acid 、 重氮甲烷 以 甲醇 、 乙醚 为溶剂， 生成 5a-(3,4-Dimethoxy-phenyl)-1,3,11a-trimethoxy-12-oxo-11a,12-dihydro-5aH-5,6,11-trioxa-naphthacene-8-carboxylic acid methyl ester
  参考文献：
  名称：

  Antioxidative Compounds from the Outer Scales of Onion

  摘要：

  Antioxidative compounds were isolated from the methanol extract of dry outer scales of onion (Allium cepa L.). Nine phenolic compounds (1-9) were finally obtained by reversed-phase high-performance liquid chromatography, and their structures were elucidated by NMR and mass spectrometry analyses. They were the six known compounds, protocatechuic acid (1), 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (2), quercetin 4'-O-beta-D-glucopyranoside (3), quercetin (5), 4'-O-beta-D-glucopyranoside of quercetin dimer (7), and quercetin dimer (8), and three novel compounds, condensation products of quercetin with protocatechuic acid (4), adduct of quercetin with quercetin 4'-O-beta-D-glucopyranoside (6), and quercetin trimer (9). These phenolic compounds were tested for their antioxiclant properties using autoxidation of methyl linoleate in bulk phase or free radical initiated peroxidation of soybean phosphatidylcholine in liposomes. The flavonoid compounds having o-dihydroxy substituent in the B-ring were shown to be effective antioxidants against nonenzymic lipid peroxidation.

  DOI：

  10.1021/jf051264d

文献信息

• Antioxidative Compounds from the Outer Scales of Onion
  作者：Tram Ngoc Ly、Chiharu Hazama、Makoto Shimoyamada、Hiromune Ando、Koji Kato、Ryo Yamauchi

  DOI：10.1021/jf051264d

  日期：2005.10.1

  Antioxidative compounds were isolated from the methanol extract of dry outer scales of onion (Allium cepa L.). Nine phenolic compounds (1-9) were finally obtained by reversed-phase high-performance liquid chromatography, and their structures were elucidated by NMR and mass spectrometry analyses. They were the six known compounds, protocatechuic acid (1), 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (2), quercetin 4'-O-beta-D-glucopyranoside (3), quercetin (5), 4'-O-beta-D-glucopyranoside of quercetin dimer (7), and quercetin dimer (8), and three novel compounds, condensation products of quercetin with protocatechuic acid (4), adduct of quercetin with quercetin 4'-O-beta-D-glucopyranoside (6), and quercetin trimer (9). These phenolic compounds were tested for their antioxiclant properties using autoxidation of methyl linoleate in bulk phase or free radical initiated peroxidation of soybean phosphatidylcholine in liposomes. The flavonoid compounds having o-dihydroxy substituent in the B-ring were shown to be effective antioxidants against nonenzymic lipid peroxidation.