dioncoquinone A | 1093228-14-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: dioncoquinone A
• 英文别名: 3,5,6-trihydroxy-2-methyl-1,4-naphthoquinone-6-O-β-glucoside
• CAS: 1093228-14-8
• 化学式: C₁₇H₁₈O₁₀
• 分子量: 382.324
• InChiKey: WVYJNTPDOVALFJ-ACMQDLBVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.22
• 重原子数：
  27.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  173.98
• 氢给体数：
  6.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  dioncoquinone A 在 盐酸 作用下， 以 甲醇 为溶剂， 反应 2.0h， 以91%的产率得到dioncoquinone B
  参考文献：
  名称：

  Antitumoral and antileishmanial dioncoquinones and ancistroquinones from cell cultures of Triphyophyllum peltatum (Dioncophyllaceae) and Ancistrocladus abbreviatus (Ancistrocladaceae)

  摘要：

  From the methanolic extracts of solid callus cultures from two species of the closely related palaeotropical plant families Dioncophyllaceae and Ancistrocladaceae seven new natural naphthoquinones were isolated, dioncoquinones A (4) and B (5) from Triphyophyllum peltatum, and ancistroquinones B (6), C (7), D (9), E (10), and F (12) from Ancistrocladus abbreviatus. Their Structures were elucidated by spectroscopic, chemical, and computational methods. Furthermore, the already known naphthoquinones plumbagin (2), droserone (3), malvone A (8), and nepenthone A (11) were found in the extract of A. abbreviatus. Dioncoquinones A (4) and B (5) showed good - and specific - activity against Leishmania major, while they were not active against other protozoic parasites. Moreover, treatment with 4 and 5 strongly induced apoptosis in human tumor cells derived from two different B cell malignancies, B cell lymphoma and multiple myeloma, without any significant toxicity towards normal peripheral mononuclear blood cells. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2008.06.019

文献信息

• Antitumoral and antileishmanial dioncoquinones and ancistroquinones from cell cultures of Triphyophyllum peltatum (Dioncophyllaceae) and Ancistrocladus abbreviatus (Ancistrocladaceae)
  作者：Gerhard Bringmann、Stefan Rüdenauer、Andreas Irmer、Torsten Bruhn、Reto Brun、Tanja Heimberger、Thorsten Stühmer、Ralf Bargou、Manik Chatterjee

  DOI：10.1016/j.phytochem.2008.06.019

  日期：2008.10

  From the methanolic extracts of solid callus cultures from two species of the closely related palaeotropical plant families Dioncophyllaceae and Ancistrocladaceae seven new natural naphthoquinones were isolated, dioncoquinones A (4) and B (5) from Triphyophyllum peltatum, and ancistroquinones B (6), C (7), D (9), E (10), and F (12) from Ancistrocladus abbreviatus. Their Structures were elucidated by spectroscopic, chemical, and computational methods. Furthermore, the already known naphthoquinones plumbagin (2), droserone (3), malvone A (8), and nepenthone A (11) were found in the extract of A. abbreviatus. Dioncoquinones A (4) and B (5) showed good - and specific - activity against Leishmania major, while they were not active against other protozoic parasites. Moreover, treatment with 4 and 5 strongly induced apoptosis in human tumor cells derived from two different B cell malignancies, B cell lymphoma and multiple myeloma, without any significant toxicity towards normal peripheral mononuclear blood cells. (c) 2008 Elsevier Ltd. All rights reserved.