7-Acetoxy-4-methyl-3-(2-acetoxy-ethyl)-cumarin | 130936-04-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-Acetoxy-4-methyl-3-(2-acetoxy-ethyl)-cumarin
• 英文别名: 7-acetoxy-3-(2-acetoxy-ethyl)-4-methyl-chromen-2-one；2-(7-Acetyloxy-4-methyl-2-oxochromen-3-yl)ethyl acetate
• CAS: 130936-04-8
• 化学式: C₁₆H₁₆O₆
• 分子量: 304.299
• InChiKey: ZOXKVQGWPFJSCA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  ocimarin 、 乙酸酐 以 吡啶 为溶剂， 生成 7-Acetoxy-4-methyl-3-(2-acetoxy-ethyl)-cumarin
  参考文献：
  名称：

  Constituents of Ocimum sanctum with Antistress Activity

  摘要：

  Three new compounds, ocimumosides A (1) and B (2) and ocimarin (3), were isolated from an extract of the leaves of holy basil (Ocimum sanctum), together with eight known substances, apigenin, apigenin-7-O-beta-D-glucopyranoside, apigenin-7-O-beta-D-glucuronic acid (4), apigenin-7-O-beta-D-glucuronic acid 6 ''-methyl ester, luteolin-7-O-beta-D-glucuronic acid 6 ''-methyl ester, luteolin-7-O-beta-D-glucopyranoside, luteolin-5-O-beta-D-glucopyranoside, and 4-allyl-1-O-beta-D-glucopyronosyl-2-hydroxybenzene (5), and two known cerebrosides. The structures of the new compounds were determined on the basis of extensive 1D and 2D NMR spectroscopic analysis. The new compounds (1-3) and the known compounds 4 and 5 were screened at a dose of 40 mg/kg body weight for acute stress-induced biochemical changes in male Sprague-Dawley rats. Compound 1 displayed promising antistress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 2 and 5 were also effective in normalizing most of these stress parameters. In contrast, compounds 3 and 4 were ineffective in normalizing any of these effects.

  DOI：

  10.1021/np0700164

文献信息

• Constituents of <i>Ocimum sanctum</i> with Antistress Activity
  作者：Prasoon Gupta、Dinesh Kumar Yadav、Kiran Babu Siripurapu、Guatam Palit、Rakesh Maurya

  DOI：10.1021/np0700164

  日期：2007.9.1

  Three new compounds, ocimumosides A (1) and B (2) and ocimarin (3), were isolated from an extract of the leaves of holy basil (Ocimum sanctum), together with eight known substances, apigenin, apigenin-7-O-beta-D-glucopyranoside, apigenin-7-O-beta-D-glucuronic acid (4), apigenin-7-O-beta-D-glucuronic acid 6 ''-methyl ester, luteolin-7-O-beta-D-glucuronic acid 6 ''-methyl ester, luteolin-7-O-beta-D-glucopyranoside, luteolin-5-O-beta-D-glucopyranoside, and 4-allyl-1-O-beta-D-glucopyronosyl-2-hydroxybenzene (5), and two known cerebrosides. The structures of the new compounds were determined on the basis of extensive 1D and 2D NMR spectroscopic analysis. The new compounds (1-3) and the known compounds 4 and 5 were screened at a dose of 40 mg/kg body weight for acute stress-induced biochemical changes in male Sprague-Dawley rats. Compound 1 displayed promising antistress effects by normalizing hyperglycemia, plasma corticosterone, plasma creatine kinase, and adrenal hypertrophy. Compounds 2 and 5 were also effective in normalizing most of these stress parameters. In contrast, compounds 3 and 4 were ineffective in normalizing any of these effects.