Sampangine beta-glucopyranose conjugate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Sampangine beta-glucopyranose conjugate
• 英文别名: (2S,3R,4S,5S,6R)-2-(10,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,8,11,13(17),14-octaen-8-yloxy)-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₂₁H₂₀N₂O₆
• 分子量: 396.4
• InChiKey: FUADXHDEKVHXKW-FFYOZGDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  29
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  124
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 Sampangine beta-glucopyranose conjugate 反应 24.0h， 以5.2 mg的产率得到[(2R,3R,4S,5R,6S)-3,4,5-triacetyloxy-6-(10,16-diazatetracyclo[7.7.1.02,7.013,17]heptadeca-1(16),2,4,6,8,11,13(17),14-octaen-8-yloxy)oxan-2-yl]methyl acetate
  参考文献：
  名称：

  Microbial Transformation of Sampangine

  摘要：

  Microbial transformation studies of the antifungal alkaloid sampangine (2) have revealed that it is metabolized by a number of microorganisms. Using a standard two-stage fermentation technique, Beauvaria bassiana (ATCC 7159), Doratomyces microsporus (ATCC 16225), and Filobasidiella neoformans (ATCC 10226) produced the 4'-O-methyl-beta-glucopyranose conjugate (3), while Absidia glauca (ATCC 22752), Cunninghamella elegans (ATCC 9245), Cunninghamella species (NRRL 5695), and Rhizopus arrhizus (ATCC 11145) produced the beta-glucopyranose conjugate (4). Metabolites 3 and 4 have been characterized on the basis of spectral data. Both 3 and 4 had significant in vitro activity against Cryptococcus neoformans but were inactive against Candida albicans. Metabolite 4 was inactive in vivo in a mouse model of cryptococcosis.

  DOI：

  10.1021/np980457a
• 作为产物：
  描述：

  D-葡萄糖 、 sampangine 在 Rhizopus arrhizus (ATCC 11145) 、 yeast 、 peptone 作用下， 以 水 、 二甲基亚砜 为溶剂， 反应 120.0h， 以83.5%的产率得到Sampangine beta-glucopyranose conjugate
  参考文献：
  名称：

  Microbial Transformation of Sampangine

  摘要：

  Microbial transformation studies of the antifungal alkaloid sampangine (2) have revealed that it is metabolized by a number of microorganisms. Using a standard two-stage fermentation technique, Beauvaria bassiana (ATCC 7159), Doratomyces microsporus (ATCC 16225), and Filobasidiella neoformans (ATCC 10226) produced the 4'-O-methyl-beta-glucopyranose conjugate (3), while Absidia glauca (ATCC 22752), Cunninghamella elegans (ATCC 9245), Cunninghamella species (NRRL 5695), and Rhizopus arrhizus (ATCC 11145) produced the beta-glucopyranose conjugate (4). Metabolites 3 and 4 have been characterized on the basis of spectral data. Both 3 and 4 had significant in vitro activity against Cryptococcus neoformans but were inactive against Candida albicans. Metabolite 4 was inactive in vivo in a mouse model of cryptococcosis.

  DOI：

  10.1021/np980457a

文献信息

• Microbial Transformation of Sampangine
  作者：Khaled Y. Orabi、Erguang Li、Alice M. Clark、Charles D. Hufford

  DOI：10.1021/np980457a

  日期：1999.7.1

  Microbial transformation studies of the antifungal alkaloid sampangine (2) have revealed that it is metabolized by a number of microorganisms. Using a standard two-stage fermentation technique, Beauvaria bassiana (ATCC 7159), Doratomyces microsporus (ATCC 16225), and Filobasidiella neoformans (ATCC 10226) produced the 4'-O-methyl-beta-glucopyranose conjugate (3), while Absidia glauca (ATCC 22752), Cunninghamella elegans (ATCC 9245), Cunninghamella species (NRRL 5695), and Rhizopus arrhizus (ATCC 11145) produced the beta-glucopyranose conjugate (4). Metabolites 3 and 4 have been characterized on the basis of spectral data. Both 3 and 4 had significant in vitro activity against Cryptococcus neoformans but were inactive against Candida albicans. Metabolite 4 was inactive in vivo in a mouse model of cryptococcosis.

表征谱图