lithospermic acid A

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: lithospermic acid A
• 英文别名: lithospermic acid；(+)-Lithospermic acid；4-[3-[1-carboxy-2-(3,4-dihydroxyphenyl)ethoxy]-3-oxoprop-1-enyl]-2-(3,4-dihydroxyphenyl)-7-hydroxy-2,3-dihydro-1-benzofuran-3-carboxylic acid
• 化学式: C₂₇H₂₂O₁₂
• 分子量: 538.464
• InChiKey: UJZQBMQZMKFSRV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.8
• 重原子数：
  39
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  211
• 氢给体数：
  7
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  lithospermic acid A 、 glutathion 反应 2.0h， 生成
  参考文献：
  名称：

  Improving the NQO1-Inducing Activities of Phenolic Acids from Radix Salvia miltiorrhiza: a Methylation Strategy

  摘要：

  NAD(P)H: quinone oxidoreductase1 (NQO1) is an important detoxification enzyme that can protect mammalian cells against toxic quinones and reduce the risk of tumorigenesis. In this study, it was found that salvianolic acid B (SaB), lithospermic acid (LA), and rosmarinic acid (RA), three main hydrophilic constituents in Danshen, conjugated with glutathione (GSH) easily in vitro but exhibited no NQO1‐inducing activities in Hepa 1c1c7 cells, which might attribute to their poor absorptions. After a simple methylation strategy that aimed at improving the liposolubility, both the NQO1‐inducing activities and the absorptions in cells of the phenolic acids improved obviously, without losing the GSH‐conjugating abilities. The concentration to double the specific activity of NQ01 values of methylated products of lithospermic acid and rosmarinic acid were 17.86 ± 2.34 μg/mL and 11.97 ± 0.60 μg/mL, respectively. The findings indicated that methylation is an effective strategy to improve the NQO1‐inducing activities of phenolic acids in Danshen.

  DOI：

  10.1111/j.1747-0285.2011.01171.x
• 作为产物：
  描述：

  salvianolic acid B 在 盐酸 、 水 作用下， 反应 24.0h， 以23.3 mg的产率得到丹参素
  参考文献：
  名称：

  通过在水溶液中的煎煮将丹酚酸B化学转化。

  摘要：

  丹酚酸B（Sal B）是丹参中含量最丰富的酚类化合物，在东方医学中已被广泛用于治疗心血管疾病。为了通过在水溶液中煎煮来阐明Sal B转化化合物的结构，将Sal B（200 mg）在pH 4.9的水溶液（200 mL）中煎煮，并将煎煮的溶液通过Sephadex LH-20柱色谱法纯化并制备HPLC。分离出13种转化的化合物，并通过NMR和MS确定化学结构。除了先前报道的4种化合物通过水煎制而成的Sal B转化产物外，首次报道了9种化合物具有从水煎Sal B溶液中分离出的化合物的完整结构，并且其中三种化合物被确定为新化合物。此外，

  DOI：

  10.1016/j.fitote.2012.06.015

文献信息

• Improving the NQO1-Inducing Activities of Phenolic Acids from Radix Salvia miltiorrhiza: a Methylation Strategy
  作者：Xiaoyu Zhang、Zhihang Song、Jinzhong Xu、Zhongjun Ma

  DOI：10.1111/j.1747-0285.2011.01171.x

  日期：2011.10

  NAD(P)H: quinone oxidoreductase1 (NQO1) is an important detoxification enzyme that can protect mammalian cells against toxic quinones and reduce the risk of tumorigenesis. In this study, it was found that salvianolic acid B (SaB), lithospermic acid (LA), and rosmarinic acid (RA), three main hydrophilic constituents in Danshen, conjugated with glutathione (GSH) easily in vitro but exhibited no NQO1‐inducing activities in Hepa 1c1c7 cells, which might attribute to their poor absorptions. After a simple methylation strategy that aimed at improving the liposolubility, both the NQO1‐inducing activities and the absorptions in cells of the phenolic acids improved obviously, without losing the GSH‐conjugating abilities. The concentration to double the specific activity of NQ01 values of methylated products of lithospermic acid and rosmarinic acid were 17.86 ± 2.34 μg/mL and 11.97 ± 0.60 μg/mL, respectively. The findings indicated that methylation is an effective strategy to improve the NQO1‐inducing activities of phenolic acids in Danshen.
• Chemical conversions of salvianolic acid B by decoction in aqueous solution
  作者：Hyoung Jae Lee、Jeong-Yong Cho、Jae-Hak Moon

  DOI：10.1016/j.fitote.2012.06.015

  日期：2012.10

  Salvianolic acid B (Sal B) is the most abundant phenolic compound in Salvia miltiorrhiza, which has been widely used for the treatment of cardiovascular diseases in Oriental medicine. To elucidate structure of the converted compounds of Sal B by decoction in aqueous solution, Sal B (200 mg) was decocted in an aqueous solution (200 mL) at pH 4.9 and the decocted solution was purified by Sephadex LH-20

  丹酚酸B（Sal B）是丹参中含量最丰富的酚类化合物，在东方医学中已被广泛用于治疗心血管疾病。为了通过在水溶液中煎煮来阐明Sal B转化化合物的结构，将Sal B（200 mg）在pH 4.9的水溶液（200 mL）中煎煮，并将煎煮的溶液通过Sephadex LH-20柱色谱法纯化并制备HPLC。分离出13种转化的化合物，并通过NMR和MS确定化学结构。除了先前报道的4种化合物通过水煎制而成的Sal B转化产物外，首次报道了9种化合物具有从水煎Sal B溶液中分离出的化合物的完整结构，并且其中三种化合物被确定为新化合物。此外，