1α,3β,28-trihydroxy-28-benzoyl olean-9(11),12-diene-3-palmitate

• 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: 1α,3β,28-trihydroxy-28-benzoyl olean-9(11),12-diene-3-palmitate
• 英文别名: cucumol B
• 化学式: C₅₃H₈₂O₅
• 分子量: 799.231
• InChiKey: QSUHWZWZMVLHHN-INYVKHKZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.93
• 重原子数：
  58.0
• 可旋转键数：
  18.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  72.83
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  甲醇 、 1α,3β,28-trihydroxy-28-benzoyl olean-9(11),12-diene-3-palmitate 在 potassium hydroxide 作用下， 反应 0.42h， 生成 棕榈酸甲酯 、 苯甲酸
  参考文献：
  名称：

  Cucumol B, a new triterpene benzoate from Cucumis melo seeds with cytotoxic effect toward ovarian and human breast adenocarcinoma

  摘要：

  Phytochemical investigation of the methanolic extract of Cucumis melo L. (Cucurbitaceae) seeds furnished a new triterpene benzoate derivative: cucumol B (1) and four known flavonoids: quercetin-3-O-beta -D-glucopyranosyl-(1 -> 6)-alpha -L-rhamnopyranoside (2), quercetin-3-O-beta -D-glucopyranoside (3), quercetin (4), and luteolin (5). Their structures were identified by UV, IR, 1D (C-13 and H-1), 2D (HSQC, H-1-H-1 COSY, HMBC, and NOESY) NMR, and HRESIMS spectral as well as comparing with literature data. Compound 1 has been assessed for the in vitro cytotoxic effect against SKOV-3, MCF-7, and HCT-116 cell lines. It had selective and potent effect toward SKOV-3 and MCF-7 cell lines with IC(50)s 2.05 and 0.41 mu M, respectively, in comparison to doxorubicin (IC(50)s 0.32 and 0.05 mu M). However, it showed moderate activity toward HCT-116 cell line with IC50 8.27 mu M.

  DOI：

  10.1080/10286020.2018.1488832

文献信息

• Cucumol B, a new triterpene benzoate from <i>Cucumis melo</i> seeds with cytotoxic effect toward ovarian and human breast adenocarcinoma
  作者：Sabrin Ragab Mohamed Ibrahim、Amgad Ibrahim Mansour Khedr、Gamal Abdallah Mohamed、Mohamed Fathalla Zayed、Amal Abd-Elmoneim Soliman El-Kholy、Rwaida Adel Al Haidari

  DOI：10.1080/10286020.2018.1488832

  日期：2019.11.2

  Phytochemical investigation of the methanolic extract of Cucumis melo L. (Cucurbitaceae) seeds furnished a new triterpene benzoate derivative: cucumol B (1) and four known flavonoids: quercetin-3-O-beta -D-glucopyranosyl-(1 -> 6)-alpha -L-rhamnopyranoside (2), quercetin-3-O-beta -D-glucopyranoside (3), quercetin (4), and luteolin (5). Their structures were identified by UV, IR, 1D (C-13 and H-1), 2D (HSQC, H-1-H-1 COSY, HMBC, and NOESY) NMR, and HRESIMS spectral as well as comparing with literature data. Compound 1 has been assessed for the in vitro cytotoxic effect against SKOV-3, MCF-7, and HCT-116 cell lines. It had selective and potent effect toward SKOV-3 and MCF-7 cell lines with IC(50)s 2.05 and 0.41 mu M, respectively, in comparison to doxorubicin (IC(50)s 0.32 and 0.05 mu M). However, it showed moderate activity toward HCT-116 cell line with IC50 8.27 mu M.