4'-β-D-glucopyranosyloxy-3'-hydroxybenzyl protocatechuate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 4'-β-D-glucopyranosyloxy-3'-hydroxybenzyl protocatechuate
• 英文别名: oreganol-A；protocatechuoyl calleryanin；Oreganol；[3-hydroxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl 3,4-dihydroxybenzoate
• 化学式: C₂₀H₂₂O₁₁
• 分子量: 438.388
• InChiKey: MFOVLHFTNQGRLH-BFMVXSJESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  186
• 氢给体数：
  7
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  4'-β-D-glucopyranosyloxy-3'-hydroxybenzyl protocatechuate 生成 D-葡萄糖
  参考文献：
  名称：

  HORI, KAZUYUKI;SATAKE, TOSHIKO;YAMAGUCHI, HIROMI;SAIKI, YASUHISA;MURAKAMI+, J. PHARM. SOC. JAP., 107,(1987) N 10, 774-779

  摘要：

  DOI：

文献信息

• DPPH Radical Scavengers from Dried Leaves of Oregano (<i>Origanum vulgare</i>)
  作者：Hideyuki MATSUURA、Hideyuki CHIJI、Chikako ASAKAWA、Midori AMANO、Teruhiko YOSHIHARA、Junya MIZUTANI

  DOI：10.1271/bbb.67.2311

  日期：2003.1

  1,1-Dipehnyl-2-picrylhydrazyl (DPPH) radical scavenging activities were found in the extract of dried leaves of oregano (Origanum vulgare). The water-soluble active ingredients were isolated, and their structures were determined to be 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybenzyl protocatechuate and 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybenzyl 4-O-methylprotocatechuate by 1H-, 13C-NMR, DEPT, HMQC, and HMBC spectral analyses, and by NOE experiments. The DPPH radical scavenging activities of these compounds were compared with those of rutin, quercetin and rosmarinic acid at a concentration of 2×10-5  M. The scavenging activity of 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybenzyl protocatechuate was almost the same as that of quercetin and rosmarinic acid, but that of 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybennzyl 4-O-methylprotocatechuate was less than that of quercetin, rosmarinic acid and 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybenzyl protocatechuate. The amount of 4′-O-β-D-glucopyranosyl-3′,4′-dihydroxybenzyl protocatechuate was estimated to be 3.8 mg/1 g of dried leaves by an HPLC analysis.

  牛至（Origanum vulgare）干叶提取物中发现了 1,1-Dipehnyl-2-picrylhydrazyl (DPPH) 自由基清除活性。分离出水溶性活性成分，并确定其结构为 4′-O-β-D-吡喃葡萄糖基-3′、通过 1H-、13C-NMR、DEPT、HMQC 和 HMBC 光谱分析以及 NOE 实验，确定了它们的结构分别为 4′-O-β-D-吡喃葡萄糖基-3′,4′-二羟基苄基原儿茶酸酯和 4′-O-β-D-吡喃葡萄糖基-3′,4′-二羟基苄基 4-O-甲基原儿茶酸酯。将这些化合物的 DPPH 自由基清除活性与浓度为 2×10-5 M 的芦丁、槲皮素和迷迭香酸进行了比较。4′-O-β-D-吡喃葡萄糖基-3′,4′-二羟基苄基原儿茶酸酯的清除活性与槲皮素和迷迭香酸基本相同，但 4′-O-β-D-吡喃葡萄糖基-3′,4′-二羟基苄基原儿茶酸酯的清除活性与槲皮素和迷迭香酸基本相同、4′-O-β-D-吡喃葡萄糖基-3′,4′-二羟基苄基原儿茶酸盐的含量低于槲皮素、迷迭香酸和 4′-O-β-D-吡喃葡萄糖基-3′,4′-二羟基苄基原儿茶酸盐。通过高效液相色谱分析，4′-O-β-D-吡喃葡萄糖基-3′,4′-二羟基苄基原儿茶酸盐的含量估计为 3.8 毫克/1 克干燥叶片。
• [EN] COSMETIC SKIN LIGHTENING AGENT AND COMPOSITION THEREOF<br/>[FR] AGENT COSMÉTIQUE D'ÉCLAIRCISSEMENT DE LA PEAU ET SA COMPOSITION
  申请人：CAVINKARE PVT LTD

  公开号：WO2010089754A1

  公开（公告）日：2010-08-12

  Improved cosmetic compositions for lightening the colour of the skin wherein the active ingredient comprises a protocatechuic acid derivative of Formula (I) or preferably a protocatechuic acid derivative, Oreganol A of Formula (II) in an effective amount along with cosmetically acceptable vehicles with or without skin benefit agents. The active ingredient is selectively isolated from the plant parts of Origanum vulgare Linn.