21,22-dihydroxy-1-{4-hydroxy-5-[(4-hydroxyphenyl)methyl]-2-oxo-2,5-dihydro-1H-pyrrol-3-yl}-2-methyldocosane-1,11-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 21,22-dihydroxy-1-{4-hydroxy-5-[(4-hydroxyphenyl)methyl]-2-oxo-2,5-dihydro-1H-pyrrol-3-yl}-2-methyldocosane-1,11-dione
• 英文别名: virgineone aglycone
• 化学式: C₃₄H₅₃NO₇
• 分子量: 587.797
• InChiKey: PTFXIKSSFZFPSE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.84
• 重原子数：
  42.0
• 可旋转键数：
  24.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  147.65
• 氢给体数：
  5.0
• 氢受体数：
  7.0

反应信息

• 作为产物：
  描述：

  virgineone 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以3 mg的产率得到21,22-dihydroxy-1-{4-hydroxy-5-[(4-hydroxyphenyl)methyl]-2-oxo-2,5-dihydro-1H-pyrrol-3-yl}-2-methyldocosane-1,11-dione
  参考文献：
  名称：

  Isolation, Structure Elucidation, and Biological Activity of Virgineone from Lachnum virgineum Using the Genome-Wide Candida albicans Fitness Test

  摘要：

  A glycosylated tetramic acid, virgineone (1), was isolated from saprotrophic Lachnum virgineum. The antifungal activity of the fermentation extract of L. virgineum was characterized in the Candida albicans fitness test as distinguishable from other natural products tested. Bioassay-guided fractionation yielded 1, a tyrosine-derived tetramic acid with a C-22 oxygenated chain and a beta-mannose. It displayed broad-spectrum antifungal activity against Candida spp. and Aspergillus fumigatus with a MIC of 4 and 16 mu g/mL, respectively. Virgineone was also identified in a number of Lachnum strains collected from diverse geographies and habitats.

  DOI：

  10.1021/np800511r

文献信息

• Isolation, Structure Elucidation, and Biological Activity of Virgineone from <i>Lachnum virgineum</i> Using the Genome-Wide <i>Candida albicans</i> Fitness Test
  作者：John Ondeyka、Guy Harris、Deborah Zink、Angela Basilio、Francisca Vicente、Gerald Bills、Gonzalo Platas、Javier Collado、Antonio González、Mercedes de la Cruz、Jesus Martin、Jennifer Nielsen Kahn、Stefan Galuska、Robert Giacobbe、George Abruzzo、Emily Hickey、Paul Liberator、Bo Jiang、Deming Xu、Terry Roemer、Sheo B. Singh

  DOI：10.1021/np800511r

  日期：2009.1.23

  A glycosylated tetramic acid, virgineone (1), was isolated from saprotrophic Lachnum virgineum. The antifungal activity of the fermentation extract of L. virgineum was characterized in the Candida albicans fitness test as distinguishable from other natural products tested. Bioassay-guided fractionation yielded 1, a tyrosine-derived tetramic acid with a C-22 oxygenated chain and a beta-mannose. It displayed broad-spectrum antifungal activity against Candida spp. and Aspergillus fumigatus with a MIC of 4 and 16 mu g/mL, respectively. Virgineone was also identified in a number of Lachnum strains collected from diverse geographies and habitats.