红曲黄素 | 50980-32-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 红曲黄素
• 英文名称: ankaflavin
• 英文别名: (3S,3aR,9aR)-9a-methyl-3-octanoyl-6-[(E)-prop-1-enyl]-3,3a,4,8-tetrahydrofuro[3,2-g]isochromene-2,9-dione
• CAS: 50980-32-0
• 化学式: C₂₃H₃₀O₅
• 分子量: 386.488
• InChiKey: AQTJNEHGKRUSLT-ODTNPMSZSA-N

物化性质

• 沸点：
  590.7±50.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.61
• 拓扑面积：
  69.7
• 氢给体数：
  0
• 氢受体数：
  5

制备方法与用途

生物活性

Ankaflavin 是从Monascus-Fermented 红米中提取得到的，是PPARγ 的激动剂，具有抗炎活性。Ankaflavin 具有选择性的细胞毒性作用，诱导癌细胞死亡。

靶点

PPARγ.

反应信息

• 作为反应物：
  描述：

  红曲黄素 、 苄胺 以 四氢呋喃 为溶剂， 反应 1.0h， 以77%的产率得到7-benzyl-9a-methyl-3-octanoyl-6-propenyl-7H,9aH-furo-[3,2-g]isoquinoline-2,9-dione
  参考文献：
  名称：

  Natural and semisynthetic azaphilones as a new scaffold for Hsp90 inhibitors

  摘要：

  A series of mold metabolites of Ascomycetes, structurally belonging to the class of azaphilones, were found to inhibit the heat shock protein Hsp90. In particular, bulgarialactone B was tested for its binding to Hsp90 using surface plasmon resonance and limited proteolysis assays and for its effects on Hsp90 client proteins expression in a series of human tumor cell lines. This compound showed high affinity for Hsp90, interacting with the 90-280 region of the N-terminal domain and down-regulated the Hsp90 client proteins Raf-1, survivin, Cdk4, Akt, and EGFR. Bulgarialactone B and other natural azaphilones showed antiproliferative activity in a panel of human tumor cell lines; their conversion into semisynthetic derivatives by reaction with primary amines increased the antiproliferative activity. Preliminary results indicated in vivo activity of bulgarialactone B against an ascitic ovarian carcinoma xenograft, thus supporting the therapeutic potential of this novel series of Hsp90 inhibitors. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.06.068