6α,7β-dihydroxyvouacapan-17β-oic acid | 40819-81-6

• 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: 6α,7β-dihydroxyvouacapan-17β-oic acid
• 英文别名: Vouacapan；(4aS,5R,6R,6aR,7S,11aS,11bR)-5,6-dihydroxy-4,4,11b-trimethyl-1,2,3,4a,5,6,6a,7,11,11a-decahydronaphtho[2,1-f][1]benzofuran-7-carboxylic acid
• CAS: 40819-81-6
• 化学式: C₂₀H₂₈O₅
• 分子量: 348.439
• InChiKey: GHQBUKANOGSFQS-WENPLGDPSA-N

物化性质

• 沸点：
  504.8±50.0 °C(Predicted)
• 密度：
  1.233±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  25
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  90.9
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6α,7β-dihydroxyvouacapan-17β-oic acid 在 sodium acetate 、 乙酸酐 作用下， 以 四氢呋喃 为溶剂， 生成 6α-hydroxyvouacapan-7β,17β-lactone
  参考文献：
  名称：

  新型6α，7β-二羟基vouacapan-17β-oic酸曼尼希碱衍生物的合成，在癌细胞中的抗增殖活性和理论研究

  摘要：

  天然产品是设计新型抗癌剂的绝佳原型。植物来源的天然产物6α，7β-二羟基vouacapan-17β-oic酸（1）有望开发出更有效的抗人类癌细胞的抗增殖剂。的确，其内酯衍生物6α-羟基vouacapan -7β，17β-内酯（2），一种非天然的呋喃二萜，比化合物1具有更高的抗癌活性。在本文中，我们描述了化合物2的六种新的曼尼希衍生物对九种癌细胞系的合成和抗增殖活性。总的来说，我们的结果表明，曼尼希衍生物3 - 8比化合物更有效2在抑制癌细胞的增殖方面。理论研究也支持我们的发现，揭示呋喃环的亲核特性是所研究的曼尼希衍生物的抗增殖活性的重要特征。

  DOI：

  10.1016/j.bmc.2010.10.015

文献信息

• Synthesis and Plant Growth Regulatory Activity of 6α,7β-Dihydroxyvouacapan-17β-oic Acid Derivatives.
  作者：Antonio J. Demuner、Luiz C. A. Barbosa、Dorila P. Veloso、Oliver W. Howarth

  DOI：10.1071/c97062

  日期：——

  Five new derivatives of 6α,7β-dihydroxyvouacapan-17β-oic acid were prepared. The effect of these new furan diterpenes on the radicle growth of Sorghum bicolor L. and Cucumis sativus L. was evaluated. All compounds, at a concentration of 100 ppm, showed an inhibitory effect (40–63%) on the radicle growth of S. bicolor L. and a small stimulatory growth effect (3–15%) on the radicle of C. sativus L. None of the compounds had any effect on the germination rate of both plants.

  制备了五种新的 6α，7β-二羟基葫芦巴泮-17β-酸衍生物 的新衍生物。这些新的呋喃二萜对高粱双色球（Sorghum bicolor L. 的影响。 的影响进行了评估。所有化合物在 浓度为 100 ppm 时，都对高粱双色根的生长有抑制作用（40-63%）。 S. bicolor L. 的胚根生长有抑制作用（40-63%），而对 S. bicolor L. 对莴苣（C. sativus L.）胚根的生长有轻微的促进作用（3-15%）。 没有一种化合物对这两种植物的发芽率有任何影响。 这两种植物的发芽率。
• Castelo-Branco, Pedro A.; Rubinger, Mayura M. M.; Resende, Jarbas M., Journal of Chemical Research, 2006, # 6, p. 351 - 353
  作者：Castelo-Branco, Pedro A.、Rubinger, Mayura M. M.、Resende, Jarbas M.、Silva, Antonio A.、Ferreira-Alves, Dalton L.、Pilo-Veloso, Dorila

  DOI：——

  日期：——
• Effect of 6α,7β-dihydroxyvouacapan-17β-oic acid and its lactone derivatives on the growth of human cancer cells
  作者：Felipe P.G. Euzébio、Flávio J.L. dos Santos、Dorila Piló-Veloso、Ana Lúcia T.G. Ruiz、João Ernesto de Carvalho、Dalton L. Ferreira-Alves、Ângelo de Fátima

  DOI：10.1016/j.bioorg.2009.03.004

  日期：2009.6

  The furanditerpene 6 alpha,7 beta-dihydroxyvouacapan-17 beta-oic acid (1) is a natural product biosynthesized by some species from the genus Pterodon (Leguminosae). This secondary metabolite has multiple biological activities that include anti-inflammatory, analgesic, plant growth regulatory, anti-edematogenic, photosystem II inhibitory and photosynthesis uncoupler, and antifungal properties. However, few studies on the antiproliferative profile of compound 1 and/or its derivatives have been reported up to date. Here, we describe the isolation of compound 1 from hexane extract of P. polygalaeflorus fruits as well as the semisynthesis of three lactone derivatives: 6 alpha-hydroxyvouacapan-7 beta,17 beta-lactone (2), 6 alpha-acetoxyvouacapan-7 beta,17 beta-lactone (3), and 6-oxovouacapan-7 beta,17 beta-lactone (4). Additionally, antiproliferative activity of these compounds against nine human cancer cell lines was investigated. Our results revealed that 6 alpha-ahydroxyvouacapan-7 beta,17 beta-lactone (2) was the most potent furanditerpene against all cancer cell lines studied. The presence of non-substituted hydroxyl group at C-6 and the presence of 7 beta,17 beta-lactone ring are important for the antiproliferative activity of these compounds. (C) 2009 Elsevier Inc. All rights reserved.
• Synthesis, antiproliferative activity in cancer cells and theoretical studies of novel 6α,7β-dihydroxyvouacapan-17β-oic acid Mannich base derivatives
  作者：Felipe P.G. Euzébio、Flávio J.L. dos Santos、Dorila Piló-Veloso、Antônio F.C. Alcântara、Ana L.T.G. Ruiz、João Ernesto de Carvalho、Mary A. Foglio、Dalton L. Ferreira-Alves、Ângelo de Fátima

  DOI：10.1016/j.bmc.2010.10.015

  日期：2010.12

  Natural products are great prototypes for the design of new anticancer agents. The plant-derived natural product 6α,7β-dihydroxyvouacapan-17β-oic acid (1) is promising for the development of more potent antiproliferative agents against human cancer cells. Indeed, its lactone derivative 6α-hydroxyvouacapan-7β,17β-lactone (2), a non-natural furanoditerpene, exhibited higher anticancer activity than compound

  天然产品是设计新型抗癌剂的绝佳原型。植物来源的天然产物6α，7β-二羟基vouacapan-17β-oic酸（1）有望开发出更有效的抗人类癌细胞的抗增殖剂。的确，其内酯衍生物6α-羟基vouacapan -7β，17β-内酯（2），一种非天然的呋喃二萜，比化合物1具有更高的抗癌活性。在本文中，我们描述了化合物2的六种新的曼尼希衍生物对九种癌细胞系的合成和抗增殖活性。总的来说，我们的结果表明，曼尼希衍生物3 - 8比化合物更有效2在抑制癌细胞的增殖方面。理论研究也支持我们的发现，揭示呋喃环的亲核特性是所研究的曼尼希衍生物的抗增殖活性的重要特征。