异水飞蓟素 | 29782-68-1

• 物质功能分类: 生物化工 - 中草药成分
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 中文名称: 异水飞蓟素
• 中文别名: 水飞蓟宁
• 英文名称: silydianin
• 英文别名: silidianin；(1R,3R,6R,7R,10R)-3-hydroxy-10-(4-hydroxy-3-methoxyphenyl)-8-[(2R,3R)-3,5,7-trihydroxy-4-oxo-2,3-dihydrochromen-2-yl]-4-oxatricyclo[4.3.1.03,7]dec-8-en-2-one
• CAS: 29782-68-1
• 化学式: C₂₅H₂₂O₁₀
• mdl: MFCD09970974
• 分子量: 482.444
• InChiKey: CYGIJEJDYJOUAN-JSGXPVSSSA-N

物化性质

• 熔点：
  191℃
• 沸点：
  819.0±65.0 °C(Predicted)
• 密度：
  1.675±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  35
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  163
• 氢给体数：
  5
• 氢受体数：
  10

安全信息

• 危险品标志：
  Xn
• 安全说明：
  S22,S45
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  2932996560
• 危险性防范说明：
  P301+P312+P330
• 危险性描述：
  H302

制备方法与用途

基本信息

• 沸点：819.028°C（760 mmHg）
• 闪点：284.985°C
• 蒸汽压：25°C时为0mmHg
• 性状：本品为粉末
• 纯度：>98%

提取来源
由菊科植物水飞蓟（Silybum marianuml (L.) Gaertn.）的干燥成熟果实或全草中提取得到的黄酮类化合物。

用途
具有抗肝中毒作用和抑制过氧化酶的作用。10−4～3×10−3克分子浓度对植物独行菜的胚生长有抑制作用。此外，还可用于含量测定、鉴定及药理实验等。

检测方式
高效液相色谱法（HPLC），纯度≥98%

储藏方法
应置于2-8°C阴凉干燥处，并避光保存。

注意事项
本品应在低温下保存，长时间暴露在空气中会导致其含量降低。

保质期
两年。注意密封且避免阳光直射。

参考资料
化学资讯网
医学药学网

用途
用于含量测定、鉴定及药理实验等。

反应信息

• 作为反应物：
  描述：

  异水飞蓟素 在 Trametes versicolor laccase 、 氧气 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 2.25h， 以21.5%的产率得到
  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

• Oxidation of flavonolignan silydianin to unexpected lactone-acid derivative
  作者：David Biedermann、Veronika Moravcová、Kateřina Valentová、Marek Kuzma、Lucie Petrásková、Ivana Císařová、Vladimír Křen

  DOI：10.1016/j.phytol.2019.01.006

  日期：2019.4

  milk thistle (Silybum marianum), is silydianin possessing an unusual bicyclic structure with the keto group next to the hemiacetal moiety. As its oxidation product 2,3-dehydrosilydianin was found to display strong chemoprotective activity and Na+/K+ ATPase inhibitory activity, the present work aims at the optimization of silydianin oxidation. The isolated yield of the optimized reaction was improved

  水飞蓟素（水飞蓟（Silybum marianum））的果实提取物水飞蓟素的主要黄酮木聚糖之一是水飞蓟素，其具有不寻常的双环结构，酮基位于半缩醛部分旁边。由于发现其氧化产物2,3-脱氢水飞蓟素具有很强的化学保护活性和Na + / K + ATPase抑制活性，因此本研究旨在优化水飞蓟素的氧化作用。优化的反应的分离产率从10％提高到22％，反应时间大大缩短（24 vs。192小时）。在优化实验中观察到了新化合物内酯酸的形成。阐明了这种新化合物的结构，并与水飞蓟素和2,3-脱氢水飞蓟素进行了比较。此外，这里首次显示了水飞蓟素的高分辨率晶体结构。
• Semisynthesis, cytotoxicity, antiviral activity, and drug interaction liability of 7-O-methylated analogues of flavonolignans from milk thistle
  作者：Hanan S. Althagafy、Tyler N. Graf、Arlene A. Sy-Cordero、Brandon T. Gufford、Mary F. Paine、Jessica Wagoner、Stephen J. Polyak、Mitchell P. Croatt、Nicholas H. Oberlies

  DOI：10.1016/j.bmc.2013.04.017

  日期：2013.7

  Silymarin, an extract of the seeds of milk thistle (Silybum marianum), is used as an herbal remedy, particularly for hepatoprotection. The main chemical constituents in silymarin are seven flavonolignans. Recent studies explored the non-selective methylation of one flavonolignan, silybin B, and then tested those analogues for cytotoxicity and inhibition of both cytochrome P450 (CYP) 2C9 activity in human liver microsomes and hepatitis C virus infection in a human hepatoma (Huh7.5.1) cell line. In general, enhanced bioactivity was observed with the analogues. To further probe the biological consequences of methylation of the seven major flavonolignans, a series of 7-O-methylflavonolignans were generated. Optimization of the reaction conditions permitted selective methylation at the phenol in the 7-position in the presence of each metabolite's 4-5 other phenolic and/or alcoholic positions without the use of protecting groups. These 7-O-methylated analogues, in parallel with the corresponding parent compounds, were evaluated for cytotoxicity against Huh7.5.1 cells; in all cases the monomethylated analogues were more cytotoxic than the parent compounds. Moreover, parent compounds that were relatively non-toxic and inactive or weak inhibitors of hepatitis C virus infection had enhanced cytotoxicity and anti-HCV activity upon 7-O-methylation. Also, the compounds were tested for inhibition of major drug metabolizing enzymes (CYP2C9, CYP3A4/5, UDP-glucuronsyltransferases) in pooled human liver or intestinal microsomes. Methylation of flavonolignans differentially modified inhibitory potency, with compounds demonstrating both increased and decreased potency depending upon the compound tested and the enzyme system investigated. In total, these data indicated that monomethylation modulates the cytotoxic, antiviral, and drug interaction potential of silymarin flavonolignans. (C) 2013 Elsevier Ltd. All rights reserved.
• Enzymatic oxidative dimerization of silymarin flavonolignans
  作者：Paolo Gavezzotti、Eva Vavříková、Kateřina Valentová、Giovanni Fronza、Tukayi Kudanga、Marek Kuzma、Sergio Riva、David Biedermann、Vladimír Křen

  DOI：10.1016/j.molcatb.2014.07.012

  日期：2014.11

  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.