(-)-(2R,3S)-fustin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: (-)-(2R,3S)-fustin
• 英文别名: (2R,3S)-2-(3,4-dihydroxyphenyl)-3,7-dihydroxy-2,3-dihydrochromen-4-one
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: FNUPUYFWZXZMIE-HUUCEWRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  rhusopolyphenol D 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 以75%的产率得到(-)-(2R,3S)-fustin
  参考文献：
  名称：

  Polyphenols from the bark of Rhus verniciflua and their biological evaluation on antitumor and anti-inflammatory activities

  摘要：

  Bioassay-guided fractionation and chemical investigation of the extract of Rhus verniciflua bark resulted in the identification of six polyphenols, rhusopolyphenols A-F (1-6), together with four known compounds including (2R,3S,10S)-7,8,9,13-tetrahydroxy-2-(3,4-dihydroxyphenyl)-2,3-trans-3,4-cis-2,3,10-trihydrobenzopyrano[3,4-c]-2-benzopyran-1-one (7), peapolyphenol C (8), cilicione-b (9) and (alpha R)-alpha,3,4,2',4'-pentahydroxydihydrochalcone (10). The structures of these polyphenols were elucidated by spectroscopic analysis, including 1D and 2D NMR, and HR-ESIMS, and their absolute configurations were further confirmed by a combination of chemical methods and CD data analysis. All isolates were evaluated for their antiproliferative activities against four human tumor cell lines (A549, SK-OV-3, SK-MEL-2, and HCT-15), and compounds 4-6, 9 and 10 showed antiproliferative activity against the tested cells, with IC50 values of 3.31-18.51 mu M. On the basis of the expanded understanding that inflammation is a crucial cause of tumor progression, the anti-inflammatory activities of these compounds were determined by measuring nitric oxide (NO) levels in the medium of murine microglia BV-2 cells. Compounds 5 and 10 significantly inhibited NO production in lipopolysaccharide (LPS)-stimulated murine microglia BV-2 cells with IC50 values of 28.90 and 12.70 mu M, respectively. (c) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.05.005

文献信息

• RHUS VERNICIFLUA STOKES EXTRACT HAVING INCREASED CONTENT OF ACTIVE FLAVONOID COMPOUND AND METHOD FOR PREPARING SAME
  申请人：AZI Company Ltd.

  公开号：EP2604274B1

  公开（公告）日：2016-07-13
• Rhus Verniciflua Stokes Extract Having Increased Content Of Active Flavonoid Compound And Method For Preparing Same
  申请人：Park Sang-Jae

  公开号：US20120283322A1

  公开（公告）日：2012-11-08

  The present invention relates to Rhus verniciflua Stokes extract having an increased content of an active flavonoid compound through a gas bubbling treatment, a method for preparing the Rhus verniciflua Stokes extract, and a method for converting fustin into fisetin through the gas bubbling treatment of a solution containing fustin. The method for preparing the Rhus verniciflua Stokes extract of the present invention can convert the conventional Rhus verniciflua Stokes extract having high content of fustin and low content of fisetin into a Rhus verniciflua Stokes extract having high content of fisetin. Therefore, the Rhus verniciflua Stokes extract of the present invention can be commercialized into natural anticancer agents, anticancer and cancer prevention food products, and health functional foods due to the excellent bioactivity thereof, and promote the development of relevant industries through the high added-value of Rhus verniciflua Stokes. In addition, the method for converting fustin into fisetin can be applied to other natural substances and be used as a method for enhancing the functionality thereof by increasing the content of a high active flavonoid, thereby becoming an enabling technology that can lead high-functionalization of natural substances.
• Method of Converting Fustin to Fisetin
  申请人：AZI COMPANY LTD.

  公开号：US20140031567A1

  公开（公告）日：2014-01-30

  The present invention relates to a method for converting fustin into fisetin through the gas bubbling treatment of a solution containing fustin. Rhus verniciflua Stokes extracts having high content of Fisetin may be used as anticancer agents, anticancer and cancer prevention food products, and health functional foods due to the excellent bioactivity thereof.
• US8551537B2
  申请人：——

  公开号：US8551537B2

  公开（公告）日：2013-10-08
• US8859014B2
  申请人：——

  公开号：US8859014B2

  公开（公告）日：2014-10-14