(2S)-1-O-octadecanoyl-2-O-tetradecanoyl-3-O-[α-D-galactopyranosyl-(1''->6')-O-β-D-galactopyranosyl]glycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (2S)-1-O-octadecanoyl-2-O-tetradecanoyl-3-O-[α-D-galactopyranosyl-(1''->6')-O-β-D-galactopyranosyl]glycerol
• 英文别名: ocimumoside B；[(2S)-2-tetradecanoyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxypropyl] octadecanoate
• 化学式: C₄₇H₈₈O₁₅
• 分子量: 893.207
• InChiKey: LGYCXVJXWRPVSQ-PLEJJZNTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.3
• 重原子数：
  62
• 可旋转键数：
  40
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  231
• 氢给体数：
  7
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  (2S)-1-O-octadecanoyl-2-O-tetradecanoyl-3-O-[α-D-galactopyranosyl-(1''->6')-O-β-D-galactopyranosyl]glycerol 在 lipase enzyme type III 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 4.0h， 生成 硬脂酸
  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.