dihydrokaempferol | 480-20-6

• 物质功能分类: 天然产物 - 黄酮类化合物
• 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: dihydrokaempferol
• 英文别名: Aromadendrin；3-hydroxynaringenin；(2R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-2,3-dihydrochromen-4-one
• CAS: 480-20-6；22425-48-5；104486-98-8；118333-31-6
• 化学式: C₁₅H₁₂O₆
• 分子量: 288.257
• InChiKey: PADQINQHPQKXNL-YSSOQSIOSA-N

物化性质

• 熔点：
  237～241℃
• 沸点：
  139-140 °C
• 密度：
  1.599±0.06 g/cm3(Predicted)
• 溶解度：
  DMSO:2.88(最大浓度 mg/mL);10.0(最大浓度 mM)
• LogP：
  2.860 (est)

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 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

安全信息

• 危险品标志：
  N,Xn
• 安全说明：
  S61
• 危险类别码：
  R50,R22
• WGK Germany：
  3

制备方法与用途

生物活性

Dihydrokaempferol 是从紫荆花 Bauhinia championii 中分离得到的。该化合物诱导细胞凋亡并抑制 Bcl-2 和 Bcl-xL 的表达，展现出作为抗关节炎新药的良好潜力。

靶点

• Apoptosis
• Bcl-2
• Bcl-xL

体外研究

Dihydrokaempferol（0.3-300 μM；48 小时）对正常滑膜细胞无显著影响，但能依赖性地减少 RA-FLSs 的活力。

1. 凋亡分析

   • 细胞系：RA-FLS
   • 浓度：3 μM, 30 μM
   • 培养时间：48 小时
   • 结果：诱导了 RA-FLS 的细胞凋亡

2. Western Blot 分析

   • 细胞系：RA-FLS
   • 浓度：3 μM, 30 μM
   • 培养时间：48 小时
   • 结果：
     • 促进了 Bax 和 Bad 的表达
     • 增加了 caspase-3、caspase-9 及 cleaved PARP 的活性片段
     • 抑制了 Bcl-2 和 Bcl-xL 的表达

3. 细胞增殖测定

   • 细胞系：正常滑膜细胞；RA-FLS 细胞
   • 浓度：0.3 μM, 3 μM, 30 μM, 300 μM
   • 培养时间：48 小时
   • 结果：减少了 RA-FLSs 的增殖

文献信息

• ANTIMICROBIAL COMPOSITION WITH LOW CYTOTOXICITY
  申请人：Ahlnäs Thomas

  公开号：US20100129302A1

  公开（公告）日：2010-05-27

  A composition includes at least one antimicrobial agent; a possible solvent system with either hydrophobic or hydrophilic nature, selected according to the target of usage; as well as possible surface active agent. The compound mixture is obtained by pulverizing wood or plant material and/or by extracting the possibly pulverized wood or plant material, so that the compound mixture contains at least two different polyphenolic compounds selected from the following group: lignans, stilbenes, juvabiones and flavonoids; the compound mixture further containing oligomers of the polyphenolic compounds, so that the compound mixture preferably has the following properties: the compound mixture has an antimicrobial effect in the composition; the cytotoxicity of the polyphenols contained in the compound mixture is at least 10 times lower with respect to BHT; the compound mixture does not irritate the skin in a so-called single patch test with contents of 0.1 wt %.
• METHOD FOR PREPARING A COMPOSITION COMPRISING A COMPOUND MIXTURE AND A CARRIER AGENT
  申请人：AHLNAS Thomas

  公开号：US20100129304A1

  公开（公告）日：2010-05-27

  In a method for preparing a composition including a compound mixture and a carrier agent, the compound mixture is obtained by pulverizing the wood material and/or by extracting the wood material so that the compound mixture contains at least two different compounds, selected from a first specified group, at least one compound selected from a second specified group, the compound mixture is mixed with the carrier agent, the amount of the compound mixture is kept in a range of 0.1-5 wt % from the total weight of the composition, providing that the range is also such that the total cytotoxicity of compound mixture dissolved in ethanol, measured for a HaCat cell culture after 24 h incubation period, is lower than the cytotoxicity of 0.02-0.1 wt % butylated hydroxy toluene (BHT) dissolved in ethanol for a HaCat cell culture after 24 h incubation period.
• [EN] METHOD FOR MINIMIZING THE CYTOTOXICITY OF THE EFFECTIVE AGENT IN A COMPOSITION THAT IS ADMINISTERED TO A MAMMAL OR GETS INTO CONTACT WITH A MAMMAL<br/>[FR] PROCÉDÉ POUR RÉDUIRE LA CYTOTOXICITÉ DE L'AGENT ACTIF DANS UNE COMPOSITION ADMINISTRÉE À UN MAMMIFÈRE OU VENANT EN CONTACT AVEC UN MAMMIFÈRE
  申请人：OY GRANULA AB LTD

  公开号：WO2009101261A2

  公开（公告）日：2009-08-20

  The invention relates to a mixture to be included in a composition or its semifinished product that is administered to a mammal or gets into contact with a mammal, said composition or its semifinished product containing at least one first effective agent; as well as a possible solvent system with either hydrophobic or hydrophilic nature, selected according to the target of usage; and a possible surface active agent. The mixture is obtained by pulverizing wood or plant material and/or by extracting the possibly pulverized wood or plant material, so that said mixture contains at least two different polyphenolic compounds, selected from among the group: lignans, stilbenes, juvabiones and flavonoids, said mixture also containing oligomers of said polyphenolic compounds; the mixture does not irritate the skin in a so-called single patch test; the cytotoxicity of the polyphenols contained in the mixture is at least 10 times lower with respect to BHT; the mixture has the same effective properties as the effective agent contained in the composition or its semifinished product; and the mixture also has effects for modifying the properties of the first effective agent, or effects for increasing the safety of usage of the first effective agent.
• [EN] METHOD FOR MINIMIZING THE CYTOTOXICITY OF THE EFFECTIVE AGENT INHIBITING THE GROWTH OF MICRO-ORGANISMS AND FOR MAXIMIZING THE EFFECT<br/>[FR] PROCÉDÉ POUR RÉDUIRE LA CYTOTOXICITÉ DE L'AGENT ACTIF INHIBANT LA CROISSANCE DE MICRO-ORGANISMES ET POUR AUGMENTER SON EFFET
  申请人：OY GRANULA AB LTD

  公开号：WO2009101262A2

  公开（公告）日：2009-08-20

  The invention relates to a mixture to be included in a composition or its semi-finished product, which composition or its semi-finished product contains at least one anti-micro-organistic agent; a possible solvent system with either hydrophobic or hydrophilic nature, selected according to the target of usage; as well as possible surface active agent. The mixture is obtained by pulverizing wood or plant material and/or by extracting the possibly pulverized wood or plant material, so that said mixture contains at least two different polyphenolic compounds selected from the following group: lignans, stilbenes, juvabiones and flavonoids; said mixture further containing oligomers of said polyphenolic compounds, so that the mixture also must have the following properties: the mixture has an anti-micro-organistic effect in the composition or in the semi-finished product; the cytotoxicity of the polyphenols contained in the mixture is at least 10 times lower with respect to BHT; the mixture does not irritate the skin in a so-called single patch test with contents of 0.1 wt%.