pestalotioquinoside A

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: pestalotioquinoside A
• 英文别名: Pestalotioquinoside A；(2S,3R,4R,5R,6S)-2-[3-[(6E)-7,11-dimethyl-3-methylidenedodeca-6,10-dien-1-ynyl]-4-hydroxyphenoxy]-6-methyloxane-3,4,5-triol
• 化学式: C₂₇H₃₆O₆
• 分子量: 456.579
• InChiKey: UOHFQHIBGIMLQJ-DASSSYLXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.98
• 重原子数：
  33.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.48
• 拓扑面积：
  99.38
• 氢给体数：
  4.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  pestalotioquinoside A 在 盐酸 、 水 作用下， 以 甲醇 为溶剂， 反应 6.0h， 生成 L-rhamnopyranose
  参考文献：
  名称：

  Ene-yne Hydroquinones from a Marine-derived Strain of the Fungus Pestalotiopsis neglecta with Effects on Liver X Receptor Alpha

  摘要：

  Seven unusual new ene-yne hydroquinones (1-3, 5-8), including three rare glycosylated derivatives named pestalotioquinosides A-C (6-8), were obtained from the marine-derived strain SCSIO41403 of the fungus Pestalotiopsis neglecta. Their structures including absolute configurations were elucidated by spectroscopic analysis and induced electronic circular dichroism experiments. In silico molecular docking and in vitro surface plasmon resonance studies showed that pestalotioquinoside C (8) could act as a liver X receptor alpha (LXR alpha) modulator. Further study showed that LXR target gene ABCA1 was significantly upregulated by 8, which revealed 8 as a potential LXR alpha agonist.

  DOI：

  10.1021/acs.jnatprod.0c00050

文献信息

• Ene-yne Hydroquinones from a Marine-derived Strain of the Fungus <i>Pestalotiopsis neglecta</i> with Effects on Liver X Receptor Alpha
  作者：Jianjiao Wang、Zhi Liang、Kunlong Li、Bin Yang、Yonghong Liu、Wei Fang、Lan Tang、Xuefeng Zhou

  DOI：10.1021/acs.jnatprod.0c00050

  日期：2020.4.24

  Seven unusual new ene-yne hydroquinones (1-3, 5-8), including three rare glycosylated derivatives named pestalotioquinosides A-C (6-8), were obtained from the marine-derived strain SCSIO41403 of the fungus Pestalotiopsis neglecta. Their structures including absolute configurations were elucidated by spectroscopic analysis and induced electronic circular dichroism experiments. In silico molecular docking and in vitro surface plasmon resonance studies showed that pestalotioquinoside C (8) could act as a liver X receptor alpha (LXR alpha) modulator. Further study showed that LXR target gene ABCA1 was significantly upregulated by 8, which revealed 8 as a potential LXR alpha agonist.