异水飞蓟宾B | 142796-22-3

• 物质功能分类: 分析化学 - 标准品 - 中药标准品
• 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
• 中文名称: 异水飞蓟宾B
• 英文名称: isosilybin B
• 英文别名: (2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-hydroxymethyl-2,3-dihydrobenzo[1,4]dioxin-6-yl]chroman-4-one；isosilibinin B；isosilibinin；isosilubin B；(2R,3R)-3,5,7-trihydroxy-2-[(2S,3S)-2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
• CAS: 142796-22-3
• 化学式: C₂₅H₂₂O₁₀
• 分子量: 482.444
• InChiKey: FDQAOULAVFHKBX-WAABAYLZSA-N

物化性质

• 熔点：
  194-196 °C(Solv: methanol (67-56-1))
• 沸点：
  793.0±60.0 °C(Predicted)
• 密度：
  1.527±0.06 g/cm3(Predicted)
• 溶解度：
  溶于二甲基亚砜

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

安全信息

• WGK Germany：
  3
• 储存条件：
  2-8℃

SDS

异水飞蓟宾BMSDS英文版

制备方法与用途

生物活性方面，IsoSilybin B 是从硅草素中分离出的一种黄酮木脂素，展现出抗前列腺癌（PCA）的活性。它能够抑制癌细胞增殖、诱导 G1 期阻滞和促进凋亡过程，并且还能导致雄激素受体的降解。

反应信息

• 作为反应物：
  描述：

  异水飞蓟宾B 在 碳酸氢钠 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以48%的产率得到2,3-dehydroisosilybin B
  参考文献：
  名称：

  水飞蓟宾和异水飞蓟宾碱催化氧化为2,3-脱氢衍生物

  摘要：

  黄酮木聚糖，水飞蓟宾和异水飞蓟宾在碱催化下氧化为相应的2，3-脱氢衍生物的过程已得到研究和优化。测试了各种碱，溶剂和反应条件，以实现最佳收率。还观察到水对反应过程的影响。发现该氧化反应可能是基于（异）水飞蓟宾（或一些中间）分子的歧化，因为该反应也在没有氧的情况下进行。我们在这里首次报告了光学纯的2,3-脱氢异水飞蓟宾A和B的制备。

  DOI：

  10.1016/j.tetlet.2012.11.049
• 作为产物：
  描述：

  C₃₉H₅₂O₁₄Si 在 盐酸 、 五甲基苯 作用下， 以 甲醇 、 水 为溶剂， 反应 10.0h， 以98%的产率得到异水飞蓟宾B
  参考文献：
  名称：

  异水飞蓟宾 B 的全合成

  摘要：

  首次报道了异水飞蓟宾 B 的全合成。异水飞蓟宾B的黄烷醇骨架的合成是通过黄烷醇的氧化来进行的。黄烷醇的立体中心是通过改进的 Julia-Kocienski 烯化、Sharpless 二羟基化和通过形成醌甲基化物中间体的酸性环化来构建的。

  DOI：

  10.1002/ejoc.202200653

文献信息

• Compositions containing silymarin and sulfoalkyl ether cyclodextrin and methods of using the same
  申请人：CyDex Pharmaceuticals, Inc.

  公开号：US11382944B2

  公开（公告）日：2022-07-12

  Cosmetic and dietary supplement compositions containing silymarin and sulfoalkyl ether cyclodextrin, particularly sulfobutyl ether cyclodextrin, are described. The compositions and methods are useful in reducing appearance of facial redness in rosacea-prone skin, rejuvenating skin, preventing skin aging, inhibiting oxidative stress in epidermal and dermal cells, increasing collagen production, reducing the likelihood of skin cancer, treating or reducing liver damage from a toxin, or treating a liver disease.

  描述了含有水飞蓟素和磺烷基醚环糊精，特别是磺丁基醚环糊精的化妆品和膳食补充剂组合物。这些组合物和方法可用于减少易患红斑痤疮的皮肤出现面部发红、嫩肤、防止皮肤老化、抑制表皮和真皮细胞中的氧化应激、增加胶原蛋白的生成、减少皮肤癌的可能性、治疗或减少毒素对肝脏的损害或治疗肝病。
• Mechanistic Study of the Biomimetic Synthesis of Flavonolignan Diastereoisomers in Milk Thistle
  作者：Hanan S. Althagafy、Maria Elena Meza-Aviña、Nicholas H. Oberlies、Mitchell P. Croatt

  DOI：10.1021/jo4011377

  日期：2013.8.2

  The mechanism for the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle is proposed to proceed by single-electron oxidation of coniferyl alcohol, subsequent reaction with one of the oxygen atoms of taxifolin's catechol moiety, and finally, further oxidation to form four of the major components of silymarin: silybin A, silybin B, isosilybin A, and isosilybin B. This mechanism is significantly different from a previously proposed process that involves the coupling of two independently formed radicals.
• 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.
• COMPOSITIONS CONTAINING SILYMARIN AND SULFOALKYL ETHER CYCLODEXTRIN AND METHODS OF USING THE SAME
  申请人：CyDex Pharmaceuticals, Inc.

  公开号：US20180133274A1

  公开（公告）日：2018-05-17

  Cosmetic and dietary supplement compositions containing silymarin and sulfoalkyl ether cyclodextrin, particularly sulfobutyl ether cyclodextrin, are described. The compositions and methods are useful in reducing appearance of facial redness in rosacea-prone skin, rejuvenating skin, preventing skin aging, inhibiting oxidative stress in epidermal and dermal cells, increasing collagen production, reducing the likelihood of skin cancer, treating or reducing liver damage from a toxin, or treating a liver disease.
• [EN] COMPOSITIONS AND METHODS RELATED TO DISSOLVED OXIDES<br/>[FR] COMPOSITIONS ET PROCÉDÉS ASSOCIÉS À DES OXYDES DISSOUS
  申请人：NATURAL EXTRACTION SYS LLC

  公开号：WO2021042001A1

  公开（公告）日：2021-03-04

  Various aspects of this patent document relate to compositions that comprise an anion that is the conjugate base of a hydrophobic molecule that has a pKa, for example, of at least 7 and no greater than 12. These compositions display improved properties when formulated to interact with an organism because the anions carry negative charges that allows them to both dissolve in water-miscible liquids and maximize their surface area. Interaction with an organism results in at least partial conversion of the anion into the hydrophobic molecule after which the hydrophobic molecule partitions out of a water-miscible liquid and into the organism.