curvularin-7-O-α-D-glucopyranoside

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: curvularin-7-O-α-D-glucopyranoside
• 英文别名: (5S)-15-hydroxy-5-methyl-13-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-4-oxabicyclo[10.4.0]hexadeca-1(12),13,15-triene-3,11-dione
• 化学式: C₂₂H₃₀O₁₀
• 分子量: 454.474
• InChiKey: ZVZVCUJMXWWVOP-SSZACWSXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  32
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.64
• 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：

  curvularin-7-O-α-D-glucopyranoside 在 盐酸 作用下， 以 水 为溶剂， 反应 2.0h， 生成 葡萄糖 、 弯抱霉菌素
  参考文献：
  名称：

  A new curvularin glycoside and its cytotoxic and antibacterial analogues from marine actinomycete Pseudonocardia sp. HS7

  摘要：

  Five curvularin macrolides (1-5) were isolated from the cultured broth of marine actinomycete Pseudonocardia sp. HS7 that was obtained from the cloacal aperture of sea cucumber Holothuria moebii. The structures of these isolates were characterized as (11S,15R)-11-hydroxycurvularin (1), (11R,15R)-11-hydroxycurvularin (2), curvularin-7-O--D-glucopyranoside (3), trans-dehydrocurvularin (4) and curvularin (5) based on their NMR and HRESIMS data as well as chemical degradation. Compound 3 is a new macrolide with a rare -D-glucopyranose substituent. Compounds 1-4, 5a and 5c (the acyl products of 5), suppressed the proliferation of all six tested cancer cell lines and 4 is the most active compound with IC50 values ranging from 0.59 to 3.39M. The 11-hydroxycurvularins 1 and 2 also showed antibacterial activity inhibiting the growth of Escherichia coli.

  DOI：

  10.1080/14786419.2015.1047775

文献信息

• A new curvularin glycoside and its cytotoxic and antibacterial analogues from marine actinomycete <i>Pseudonocardia</i> sp. HS7
  作者：Xuewei Ye、Komal Anjum、Tengfei Song、Wenling Wang、Siran Yu、Haocai Huang、Xiao-Yuan Lian、Zhizhen Zhang

  DOI：10.1080/14786419.2015.1047775

  日期：2016.5.18

  Five curvularin macrolides (1-5) were isolated from the cultured broth of marine actinomycete Pseudonocardia sp. HS7 that was obtained from the cloacal aperture of sea cucumber Holothuria moebii. The structures of these isolates were characterized as (11S,15R)-11-hydroxycurvularin (1), (11R,15R)-11-hydroxycurvularin (2), curvularin-7-O--D-glucopyranoside (3), trans-dehydrocurvularin (4) and curvularin (5) based on their NMR and HRESIMS data as well as chemical degradation. Compound 3 is a new macrolide with a rare -D-glucopyranose substituent. Compounds 1-4, 5a and 5c (the acyl products of 5), suppressed the proliferation of all six tested cancer cell lines and 4 is the most active compound with IC50 values ranging from 0.59 to 3.39M. The 11-hydroxycurvularins 1 and 2 also showed antibacterial activity inhibiting the growth of Escherichia coli.