guttiferone A

• 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: guttiferone A
• 化学式: C₃₈H₅₀O₆
• 分子量: 602.811
• InChiKey: QKKRBNPMUBNTPA-GHCWVHGPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.06
• 重原子数：
  44.0
• 可旋转键数：
  11.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  111.9
• 氢给体数：
  3.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  guttiferone A 在 四甲基氢氧化铵 、 四乙基氯化铵 作用下， 以 甲醇 为溶剂， 以53%的产率得到3,16-oxyguttiferone A
  参考文献：
  名称：

  Polycyclic Polyprenylated Xanthones from Symphonia globulifera: Isolation and Biomimetic Electrosynthesis

  摘要：

  Two regioisomeric polycydic xanthones, 3,16-oxyguttiferone A (2) and 1,16-oxyguttiferone A (3), which are polyprenylated acylphloroglucinol-derived analogues, were isolated from the seeds of Symphonia globulifera, together with their presumed o-dihydroxybenzoyl precursor, guttiferone A (1). Anodic oxidation of 1 into the corresponding o-quinone species proved to be an efficient biomimetic method to generate xanthones 2 and 3 in high overall yield and to confirm their structures. Both compounds displayed cytotoxicity against the HCT 116 colon carcinoma cell line with IC50 values of 8 and 3 mu M, respectively.

  DOI：

  10.1021/acs.jnatprod.5b00239

文献信息

• Synthesis of novel guttiferone A derivatives: In-vitro evaluation toward Plasmodium falciparum, Trypanosoma brucei and Leishmania donovani
  作者：Yann Fromentin、Nicolas Gaboriaud-Kolar、Bruno Ndjakou Lenta、Jean Duplex Wansi、Didier Buisson、Elisabeth Mouray、Philippe Grellier、Philippe M. Loiseau、Marie-Christine Lallemand、Sylvie Michel

  DOI：10.1016/j.ejmech.2013.04.066

  日期：2013.7

  The catechol pharmacomodulation of the natural product guttiferone A, isolated from the Symphonia globulifera tree, led to the semisynthesis of a collection of twenty derivatives. The ester and ether derivatives of guttiferone A were evaluated for their anti-plasmodial, trypanocidal and anti-leishmanial activities. Some compounds described below have shown potent antiparasitic activity against Plasmodium falciparum, Trypanosoma brucei and Leishmania donovani in a range from 1 to 5 mu M. The evaluation of guttiferone A derivatives against VERO cells highlighted catechol modulations as an interesting tool to decrease the toxicity and keep the activity of this natural compound. The current study revealed new molecules as promising new antiparasitic drug candidates. (C) 2013 Elsevier Masson SAS. All rights reserved.
• METHODS OF TREATMENT USING SIRT MODULATORS AND COMPOSITIONS CONTAINING SIRT1 MODULATORS
  申请人：Farmer Stephen R.

  公开号：US20100210692A1

  公开（公告）日：2010-08-19

  Methods of treatment using SIR1 modulators and compositions containing SIRT1 modulators are described. Combinations of a SIRT1 modulator and a second agent, and uses of such combinations, are also described.
• HISTONE DEACETYLASE INHIBITORS, COMBINATION THERAPIES AND METHODS OF USE
  申请人：Baylin Stephen

  公开号：US20110104177A1

  公开（公告）日：2011-05-05

  The invention relates to histone deacetylase (HDAC) inhibitors to treat proliferative diseases. The present invention provides novel class III histone deacetylase inhibitors, in particular SIRT1 inhibitors, to reverse the silencing of hypermethylated genes, in combination with one or more other agents, in proliferative diseases such as cancer. The present invention provides methods of activating genes that are silenced by methylation in a subject by administering a HDAC inhibitor in combination with one or more agents.
• Polycyclic Polyprenylated Xanthones from <i>Symphonia globulifera</i>: Isolation and Biomimetic Electrosynthesis
  作者：Kevin Cottet、Anne Neudörffer、Marina Kritsanida、Sylvie Michel、Marie-Christine Lallemand、Martine Largeron

  DOI：10.1021/acs.jnatprod.5b00239

  日期：2015.8.28

  Two regioisomeric polycydic xanthones, 3,16-oxyguttiferone A (2) and 1,16-oxyguttiferone A (3), which are polyprenylated acylphloroglucinol-derived analogues, were isolated from the seeds of Symphonia globulifera, together with their presumed o-dihydroxybenzoyl precursor, guttiferone A (1). Anodic oxidation of 1 into the corresponding o-quinone species proved to be an efficient biomimetic method to generate xanthones 2 and 3 in high overall yield and to confirm their structures. Both compounds displayed cytotoxicity against the HCT 116 colon carcinoma cell line with IC50 values of 8 and 3 mu M, respectively.