bionectriol D

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: bionectriol D
• 英文别名: Bionectriol D；(2R,3S,4E,6S,7S,8E,10S,11S,12E,14S,15R,16S,18S,20S)-3,7,11-trihydroxy-2,4,6,8,10,12,14,16,18,20-decamethyl-15-[(2R,3S,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxydocosa-4,8,12-trienoic acid
• 化学式: C₃₈H₆₈O₁₁
• 分子量: 700.951
• InChiKey: IXACCXKOOUBCOZ-SMYMJKOMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  49
• 可旋转键数：
  20
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  197
• 氢给体数：
  8
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  甲醇 、 bionectriol D 在 盐酸 作用下， 反应 1.5h， 以Ca. 1 mg的产率得到甲基-D-丙噻
  参考文献：
  名称：

  Polyketide Glycosides from Bionectria ochroleuca Inhibit Candida albicans Biofilm Formation

  摘要：

  One of the challenges presented by Candida infections is that many of the isolates encountered in the clinic produce biofilms, which can decrease these pathogens' susceptibilities to standard-of-care antibiotic therapies. Inhibitors of fungal biofilm formation offer a potential solution to counteracting some of the problems associated with Candida infections. A screening campaign utilizing samples from our fungal extract library revealed that a Bionectria ochroleuca isolate cultured on Cheerios breakfast cereal produced metabolites that blocked the in vitro formation of Candida albicans biofilms. A scale-up culture of the fungus was undertaken using mycobags (also known as mushroom bags or spawn bags), which afforded four known [TMC-151s C-F (1-4)] and three new [bionectriols B-D (5-7)] polyketide glycosides. All seven metabolites exhibited potent biofilm inhibition against C. albicans SC5314, as well as exerted synergistic antifungal activities in combination with amphotericin B. In this report, we describe the structure determination of the new metabolites, as well as compare the secondary metabolome profiles of fungi grown in flasks and mycobags. These studies demonstrate that mycobags offer a useful alternative to flask-based cultures for the preparative production of fungal secondary metabolites.

  DOI：

  10.1021/np500531j
• 作为产物：
  描述：

  bionectriol C 在 水 、 sodium hydroxide 作用下， 以 乙酸乙酯 为溶剂， 反应 2.0h， 以7.4 mg的产率得到bionectriol D
  参考文献：
  名称：

  Polyketide Glycosides from Bionectria ochroleuca Inhibit Candida albicans Biofilm Formation

  摘要：

  One of the challenges presented by Candida infections is that many of the isolates encountered in the clinic produce biofilms, which can decrease these pathogens' susceptibilities to standard-of-care antibiotic therapies. Inhibitors of fungal biofilm formation offer a potential solution to counteracting some of the problems associated with Candida infections. A screening campaign utilizing samples from our fungal extract library revealed that a Bionectria ochroleuca isolate cultured on Cheerios breakfast cereal produced metabolites that blocked the in vitro formation of Candida albicans biofilms. A scale-up culture of the fungus was undertaken using mycobags (also known as mushroom bags or spawn bags), which afforded four known [TMC-151s C-F (1-4)] and three new [bionectriols B-D (5-7)] polyketide glycosides. All seven metabolites exhibited potent biofilm inhibition against C. albicans SC5314, as well as exerted synergistic antifungal activities in combination with amphotericin B. In this report, we describe the structure determination of the new metabolites, as well as compare the secondary metabolome profiles of fungi grown in flasks and mycobags. These studies demonstrate that mycobags offer a useful alternative to flask-based cultures for the preparative production of fungal secondary metabolites.

  DOI：

  10.1021/np500531j