25-hydroxy-3-epidehydrotumulosic acid | 167775-55-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: 25-hydroxy-3-epidehydrotumulosic acid
• 英文别名: (2R)-2-[(3R,5R,10S,13R,14R,16R,17R)-3,16-dihydroxy-4,4,10,13,14-pentamethyl-2,3,5,6,12,15,16,17-octahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-hydroxy-6-methyl-5-methylideneheptanoic acid
• CAS: 167775-55-5
• 化学式: C₃₁H₄₈O₅
• 分子量: 500.719
• InChiKey: GDIGQYHXIOMOQU-NEAGZGJDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  25-hydroxy-3-epidehydrotumulosic acid 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 乙酸乙酯 为溶剂， 反应 7.0h， 生成 (20R)-3,4-seco-24-methyllanosta-4(28),8,24(24(1))-triene-3,16α,21-triol
  参考文献：
  名称：

  Cytotoxic and Apoptosis-Inducing Activities of Triterpene Acids from Poria cocos

  摘要：

  Six lanostane-type triterpene acids (1a-6a), isolated from Poria cocos, and their methyl ester (1b-6b) and hydroxy derivatives (1c-6c) were prepared. Upon evaluation a of the cytotoxic activity of these compounds against leukemia (HL60), lung (A549), melanoma (CRL1579), ovary (NIH:OVCAR-3), breast (SK-BR-3), prostate (DU145), stomach (AZ521), and pancreas (PANC-1) cancer cell lines, 11 compounds (5a, 6a, 2b-5b, 1c, and 3c-6c) exhibited activity with single digit micromolar IC50 values against one or more cell lines. Poricotriol A (1c), a hydroxy derivative of poricoic acid A (la), exhibited potent cytotoxicities against six cell lines with IC50 values of 1.2-5.5 mu M. Poricotriol A induced typical apoptotic cell death in HL60 and A549 cells on evaluation of the apoptosis-inducing activity by flow cytometric analysis. Western blot analysis in HL60 cells showed that poricotriol A activated caspases-3, -8, and -9, while increasing the ratio of Bax/Bcl-2. This suggested that poricotriol A induced apoptosis via both mitochondrial and death receptor pathways in HL60, On the other hand, poricotriol A did not activate caspases-3, -8, and -9, but induced translocation of apoptosis-inducing factor (AIF) from mitochondria and increased the ratio of Bax/Bcl-2 in A549. This suggested that poricotriol A induced apoptosis via the mitochondrial pathway mostly by translocation of AIF, independent from the caspase pathway in A549. Furthermore, poricotriol A was shown to possess high selective toxicity in lung cancer cells since it exhibited only weak cytotoxicity against a normal lung cell line (WI-38).

  DOI：

  10.1021/np100402b

文献信息

• Cytotoxic and Apoptosis-Inducing Activities of Triterpene Acids from Poria cocos
  作者：Takashi Kikuchi、Emiko Uchiyama、Motohiko Ukiya、Keiichi Tabata、Yumiko Kimura、Takashi Suzuki、Toshihiro Akihisa

  DOI：10.1021/np100402b

  日期：2011.2.25

  Six lanostane-type triterpene acids (1a-6a), isolated from Poria cocos, and their methyl ester (1b-6b) and hydroxy derivatives (1c-6c) were prepared. Upon evaluation a of the cytotoxic activity of these compounds against leukemia (HL60), lung (A549), melanoma (CRL1579), ovary (NIH:OVCAR-3), breast (SK-BR-3), prostate (DU145), stomach (AZ521), and pancreas (PANC-1) cancer cell lines, 11 compounds (5a, 6a, 2b-5b, 1c, and 3c-6c) exhibited activity with single digit micromolar IC50 values against one or more cell lines. Poricotriol A (1c), a hydroxy derivative of poricoic acid A (la), exhibited potent cytotoxicities against six cell lines with IC50 values of 1.2-5.5 mu M. Poricotriol A induced typical apoptotic cell death in HL60 and A549 cells on evaluation of the apoptosis-inducing activity by flow cytometric analysis. Western blot analysis in HL60 cells showed that poricotriol A activated caspases-3, -8, and -9, while increasing the ratio of Bax/Bcl-2. This suggested that poricotriol A induced apoptosis via both mitochondrial and death receptor pathways in HL60, On the other hand, poricotriol A did not activate caspases-3, -8, and -9, but induced translocation of apoptosis-inducing factor (AIF) from mitochondria and increased the ratio of Bax/Bcl-2 in A549. This suggested that poricotriol A induced apoptosis via the mitochondrial pathway mostly by translocation of AIF, independent from the caspase pathway in A549. Furthermore, poricotriol A was shown to possess high selective toxicity in lung cancer cells since it exhibited only weak cytotoxicity against a normal lung cell line (WI-38).