eucalmaidin E | 1187303-40-7

• 物质功能分类: 天然产物 - 萜类
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 糖脂
• 英文名称: eucalmaidin E
• 英文别名: 1,6-di-O-[(R)-oleuropeyl]-β-D-glucopyranose；cuniloside B；[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(4R)-4-(2-hydroxypropan-2-yl)cyclohexene-1-carbonyl]oxyoxan-2-yl]methyl (4R)-4-(2-hydroxypropan-2-yl)cyclohexene-1-carboxylate
• CAS: 1187303-40-7
• 化学式: C₂₆H₄₀O₁₀
• 分子量: 512.598
• InChiKey: JOLLIDAUJSAZHE-SKNUFNKISA-N

物化性质

• 沸点：
  680.4±55.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  36
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  eucalmaidin E 在 水 、 β-glucosidase 作用下， 反应 192.0h， 以2 mg的产率得到(+)-oleuropeic acid
  参考文献：
  名称：

  来自麦加桉树新鲜叶子的真花青素A-E，（+）-油酸衍生物

  摘要：

  五个新的（+） - oleuropeic酸衍生物，eucalmaidins A-E（1 - 5），加上12种已知化合物（6 - 17），从新鲜叶中分离直杆蓝桉。在光谱分析（HSQC，HMBC和1 H- 1 H COSY），化学降解和酶水解的基础上确定了新化合物的结构。在测试的化合物中，只有槲皮素在体外显示出轻微的抗单纯疱疹病毒1（HSV-1）活性。

  DOI：

  10.1021/np900290s
• 作为产物：
  描述：

  葡萄糖 、 (+)-oleuropeic acid 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 以7.2%的产率得到eucalmaidin E
  参考文献：
  名称：

  Synthesis of the monoterpenoid esters cypellocarpin C and cuniloside B and evidence for their widespread occurrence in Eucalyptus

  摘要：

  Short syntheses of cuniloside B and cypellocarpin C, (+)-(R)-oleuropeic acid-containing carbohydrates, are reported. Also disclosed are syntheses of the noreugenin glycosides, undulatoside A and corymbosins K-1 and K-2. Leaf extracts of 28 diverse eucalypts revealed cuniloside B to be present in all, and cypellocarpin C to be present in most, of the species examined. The widespread occurrence of these carbohydrate monoterpenoid esters supports their roles in essential oil biosynthesis or mobilization from sites of synthesis to secretory cavity lumena. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2010.07.029

文献信息

• Non-volatile components of the essential oil secretory cavities of Eucalyptus leaves: Discovery of two glucose monoterpene esters, cuniloside B and froggattiside A
  作者：Jason Q.D. Goodger、Benjamin Cao、Inneke Jayadi、Spencer J. Williams、Ian E. Woodrow

  DOI：10.1016/j.phytochem.2009.06.004

  日期：2009.6

  The essential oils extracted from the embedded foliar secretory cavities of many Eucalyptus species are of economic value as pharmaceuticals and fragrance additives. Recent studies have indicated that Eucalyptus secretory cavities may not be exclusively involved in the biosynthesis and storage of essential oils. Therefore, we selected three species upon which to perform an examination of the contents of foliar secretory cavities: Eucalyptus froggattii, E. polybractea and E. globulus. This paper describes the isolation and structural characterization of two non-volatile glucose monoterpene esters, which we have named cuniloside B and froggattiside A, from within the secretory cavities of these species, and shows the presence of these compounds in solvent extracts of the leaves from two other species of Eucalyptus. Both compounds were found in high proportions relative to the essential oils extracted from the leaves. We propose that many other carbohydrate monoterpene esters previously isolated from bulk leaf extracts of various Eucalyptus species may also be localized within the non-volatile fraction of foliar secretory cavities. (C) 2009 Elsevier Ltd. All rights reserved.