silibinin

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 黄酮木脂素
• 英文名称: silibinin
• 英文别名: silybin；(2S,3S)-3,5,7-trihydroxy-2-[(2S,3S)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
• 化学式: C₂₅H₂₂O₁₀
• 分子量: 482.444
• InChiKey: SEBFKMXJBCUCAI-PQVVKJAFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  35
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  silibinin 在 palladium on activated charcoal 、 laccase from Trametesver sicolor 、 氢气 、 potassium carbonate 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 28.0h， 生成
  参考文献：
  名称：

  Enzymatic oxidative dimerization of silymarin flavonolignans

  摘要：

  Dimerization of phenolic compounds can potentially enhance their biological (antioxidant) activity. We present here the selective oxidative dimerization of several flavonolignans from Silybum marianum seed extract, namely, silybin A (1a), silybin B (1b), silychristin (3), and silydianin (4) catalyzed by a laccase from Trametes versicolor. Selective benzylation of C-7 OH group of both silybins ensured the priority of the dimerization reaction, avoiding thus polymerization. C-C homodimers connected via E-rings of silybin A and B and silydianin dimers were successfully isolated after respective debenzylation. On the contrary, dimerization of 7-O-benzyl silychristin afforded a complex, inseparable mixture of the products. All isolated flavonolignan dimers exhibited significantly improved 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity compared to their monomers and, therefore, seem to be promising for further biological studies. (C) 2014 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.molcatb.2014.07.012

文献信息

• METHOD OF BIOTRANSFORMATION OF BENZOPYRONE COMPOUNDS INTO THE CORRESPONDING PHOSPHATE-CONJUGATED DERIVATIVES
  申请人：National Taiwan University

  公开号：US20170305944A1

  公开（公告）日：2017-10-26

  The present invention is related to a biotransformation process, effected by means of an isolated polypeptide possessing benzopyrone phosphate synthetase activity, and also a microorganism comprising a nucleic acid sequence that encodes the polypeptide, for the preparation of phosphate-conjugated derivatives of benzopyrone compounds. The hydrophilic property of the benzopyrone compounds is enhanced after catalyzed by the benzopyrone phosphate synthetase of the present invention.

  本发明涉及一种生物转化过程，通过一种具有苯并吡喃磷酸合酶活性的分离多肽实现，并且包括一种编码该多肽的核酸序列的微生物，用于制备苯并吡喃化合物的磷酸共轭衍生物。经本发明的苯并吡喃磷酸合酶催化后，苯并吡喃化合物的亲水性质得到增强。
• SILYBIN INJECTION AND PREPARATION METHOD THEREFOR
  申请人：Tasly Pharmaceutical Group Co., Ltd.

  公开号：EP3243512A1

  公开（公告）日：2017-11-15

  A silybin injection contains silybin, sulfobutyl ether-β-cyclodextrin, an organic solvent for injection and may further contain a co-solvent, a lyophilization proppant, a pH regulator, water for injection and the like.

  水飞蓟宾注射液含有水飞蓟宾、磺丁基醚-β-环糊精、注射用有机溶剂，还可能含有助溶剂、冻干支撑剂、pH 值调节剂、注射用水等。
• Silybin injection and preparation method therefor
  申请人：TASLY PHARMACEUTICAL GROUP CO., LTD.

  公开号：US10314923B2

  公开（公告）日：2019-06-11

  A silybin injection contains silybin, sulfobutyl ether-β-cyclodextrin, an organic solvent for injection, a pH regulator, and may further contain a co-solvent, a lyophilization bulking agent, and water for injection.

  水飞蓟宾注射液含有水飞蓟宾、磺丁基醚-β-环糊精、注射用有机溶剂、pH 值调节剂，还可能含有助溶剂、冻干膨松剂和注射用水。
• Method of biotransformation of benzopyrone compounds into the corresponding phosphate-conjugated derivatives
  申请人：National Taiwan University

  公开号：US10421768B2

  公开（公告）日：2019-09-24

  The present invention is related to a biotransformation process, effected by means of an isolated polypeptide possessing benzopyrone phosphate synthetase activity, and also a microorganism comprising a nucleic acid sequence that encodes the polypeptide, for the preparation of phosphate-conjugated derivatives of benzopyrone compounds. The hydrophilic property of the benzopyrone compounds is enhanced after catalyzed by the benzopyrone phosphate synthetase of the present invention.

  本发明涉及一种生物转化过程，该过程通过一种具有吡喃苯酮磷酸合成酶活性的分离多肽和一种包含编码该多肽的核酸序列的微生物来实现，用于制备吡喃苯酮化合物的磷酸结合衍生物。经本发明的苯并吡喃酮磷酸合成酶催化后，苯并吡喃酮化合物的亲水性增强。
• Berberine-silybin salt achieves improved anti-nonalcoholic fatty liver disease effect through regulating lipid metabolism
  作者：Xiaolei Ma、Xiaoyou Yu、Rui Li、Jinjin Cui、Haoyang Yu、Ling Ren、Jiandong Jiang、Wenxuan Zhang、Lulu Wang

  DOI：10.1016/j.jep.2023.117238

  日期：2024.1