5-(6-aminopurin-9H-9-yl)-5-deoxy-D-ribofuranoside | 29789-09-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 5-(6-aminopurin-9H-9-yl)-5-deoxy-D-ribofuranoside
• 英文别名: (2R,3R,4S,5R)-5-[(6-aminopurin-9-yl)methyl]oxolane-2,3,4-triol
• CAS: 29789-09-1
• 化学式: C₁₀H₁₃N₅O₄
• 分子量: 267.244
• InChiKey: GRSHCMCYZLQGJH-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  140
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  5-(6-aminopurin-9H-9-yl)-5-deoxy-D-ribofuranoside 在 air 作用下， 生成 4-(9-腺嘌呤)-D-鞘氨醇-2,3-二羟基丁酸
  参考文献：
  名称：

  Quantification of the Bioactive Compound Eritadenine in Selected Strains of Shiitake Mushroom (Lentinus edodes)

  摘要：

  Cardiovascular disease is one of the most common causes of death in the Western world, and a high level of blood cholesterol is considered a risk factor. The edible fungus, shiitake mushroom (Lentinus edodes), contains the hypocholesterolemic agent eritadenine, 2(R),3(R)-dihydroxy-4-(9-adenyl)-butyric acid. This study was conducted to quantify the amount of the cholesterol reducing agent eritadenine in shiitake mushrooms, in search of a potential natural medicine against blood cholesterol. The amounts of eritadenine in the fruit bodies of four different shiitake mushrooms, Le-1, Le-2, Le-A, and Le-B, were investigated in this study. To achieve this goal, methanol extraction was used to recover as much as possible of the hypocholesterolemic agent from the fungal cells. In addition, enzymes that degrade the fungal cell walls were also used to elucidate if the extraction could be further enhanced. To analyze the target compound, a reliable and reproducible HPLC method for separation, identification, and quantification of eritadenine was developed. The shiitake strains under investigation exhibit up to 10 times higher levels of eritadenine than previously reported for other shiitake strains. Further, pretreating the mushrooms with hydrolytic enzymes before methanol extraction resulted in an insignificant increase in the amount of eritadenine released. These results indicate the potential for delivery of therapeutic amounts of eritadenine from the ingestion of extracts or dried concentrates of shiitake mushroom strains.

  DOI：

  10.1021/jf062559+
• 作为产物：
  描述：

  methyl 5-(6-aminopurin-9H-9-yl)-2,3-O-isopropylidene-5-deoxy-β-D-ribofuranoside 在 水 作用下， 生成 5-(6-aminopurin-9H-9-yl)-5-deoxy-D-ribofuranoside
  参考文献：
  名称：

  Quantification of the Bioactive Compound Eritadenine in Selected Strains of Shiitake Mushroom (Lentinus edodes)

  摘要：

  Cardiovascular disease is one of the most common causes of death in the Western world, and a high level of blood cholesterol is considered a risk factor. The edible fungus, shiitake mushroom (Lentinus edodes), contains the hypocholesterolemic agent eritadenine, 2(R),3(R)-dihydroxy-4-(9-adenyl)-butyric acid. This study was conducted to quantify the amount of the cholesterol reducing agent eritadenine in shiitake mushrooms, in search of a potential natural medicine against blood cholesterol. The amounts of eritadenine in the fruit bodies of four different shiitake mushrooms, Le-1, Le-2, Le-A, and Le-B, were investigated in this study. To achieve this goal, methanol extraction was used to recover as much as possible of the hypocholesterolemic agent from the fungal cells. In addition, enzymes that degrade the fungal cell walls were also used to elucidate if the extraction could be further enhanced. To analyze the target compound, a reliable and reproducible HPLC method for separation, identification, and quantification of eritadenine was developed. The shiitake strains under investigation exhibit up to 10 times higher levels of eritadenine than previously reported for other shiitake strains. Further, pretreating the mushrooms with hydrolytic enzymes before methanol extraction resulted in an insignificant increase in the amount of eritadenine released. These results indicate the potential for delivery of therapeutic amounts of eritadenine from the ingestion of extracts or dried concentrates of shiitake mushroom strains.

  DOI：

  10.1021/jf062559+