8-姜酚 | 30462-35-2

• 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: 8-姜酚
• 中文别名: 3,3'-二没食子酸酯茶黄素
• 英文名称: theaflavin-3,3'-di-o-gallate
• 英文别名: Theaflavin-3,3'-digallate；theaflavin-3,3′-digallate；theaflavin digallate；theaflavin-3,3’-digallate；theaflavin-3,3'-bisgallate；theaflavin 3,3'-O-digallate；theaflavin-3,3'-gallate；TFDG；(3,4,6-Trihydroxy-5-oxo-5H-benzo[7]annulene-1,8-diyl)bis[(2R,3R)-5,7-dihydroxy-3,4-dihydro-2H-chromene-2,3-diyl] bis(3,4,5-trihydroxybenzoate)；[(2R,3R)-2-[1-[(2R,3R)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyl)oxy-3,4-dihydro-2H-chromen-2-yl]-3,4,6-trihydroxy-5-oxobenzo[7]annulen-8-yl]-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
• CAS: 30462-35-2
• 化学式: C₄₃H₃₂O₂₀
• 分子量: 868.715
• InChiKey: ZEASWHWETFMWCV-ISBUVJFSSA-N

物化性质

• 熔点：
  226～230℃
• 沸点：
  1352.6±65.0 °C(Predicted)
• 密度：
  1.97±0.1 g/cm3(Predicted)
• 溶解度：
  DMSO：41.67 mg/mL（47.97 mM；需要超声波）
• 碰撞截面：
  268.4 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  63
• 可旋转键数：
  8
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  351
• 氢给体数：
  13
• 氢受体数：
  20

安全信息

• WGK Germany：
  3
• 海关编码：
  29329990
• 危险品运输编号：
  NONH for all modes of transport

制备方法与用途

8-姜酚是一种重要的姜中活性成分，具有多种生物学和药理学作用。以下是关于8-姜酚的详细信息：

化学性质

• 来源：8-姜酚是从生姜（Zingiber officinale）中提取的一种天然化合物。
• 结构：它属于姜酮类化合物，其化学名称为1,6-二甲氧基-2,3,4,5-四氢异苯并呋喃-7(8H)-酮。
• 分子量：约206.2 g/mol。

生物学和药理作用

• 免疫调节作用：研究表明，8-姜酚能够调节小鼠脾淋巴细胞的增殖，表现出一定的免疫调节功能。这表明它可能在增强机体免疫力方面有一定的潜力。
• 抗炎作用：有研究显示，8-姜酚具有抑制炎症反应的作用，可以减少多种炎症介质的释放。

分析测定

1. 高效液相色谱（HPLC）和紫外光谱法：
   • 通过该方法能够定性鉴定姜提取物中的辛辣组分，包括6-姜酚、8-姜酚、10-姜酚等。
2. 液相色谱-串联质谱（LC-MS/MS）法：
   • 建立了检测和定量分析姜酚相关化合物的方法，通过中性损失扫描和选择反应监测建立了灵敏的检测方法。

应用

1. 在功能性食品或保健品中的应用：由于其多种潜在生物活性，8-姜酚被用于开发具有特定健康功效的产品。
2. 医药研究：作为药物候选物之一，参与抗炎、免疫调节等相关疾病的研究与开发。

结论

总之，8-姜酚作为一种重要的天然产物，在多个领域展现出应用潜力。未来的研究将进一步探讨其具体的作用机制及其在各种疾病预防和治疗中的应用价值。

反应信息

• 作为反应物：
  描述：

  8-姜酚 、 表儿茶素 在 双氧水 、 horseradish peroxidase 作用下， 以 水 、 丙酮 为溶剂， 以25 mg的产率得到theatribenzotropolone A
  参考文献：
  名称：

  New dibenzotropolone derivatives characterized from black tea using LC/MS/MS

  摘要：

  Theaflavins and thearubigins are major pigments in black tea, and it is generally accepted that they are produced by oxidation of flavan-3-ols (catechins) during tea fermentation. In the course of studies on the oxidation mechanism of tea polyphenols, especially the formation of thearubigins, a method combining the enzymatic synthesis and LC/ESI-MS/MS analysis was developed to search for new higher molecular weight polymers from black tea. Three new dibenzotropolones, theadibenzotropolone A, B, and C, together with one new tribenzotropolone, theatribenzotropolone A, were formed by the reaction of theaflavins and tea catechins with horseradish peroxidase in the presence of H2O2. The structures of these new benzotropolone derivatives were elucidated on the basis of MS and 2D NMR spectroscopic analyses. The existence of these compounds in black tea was characterized by LC/ESI-MS/MS. Theadibenzotropolone A and B were the first benzotropolone-type trimers of catechins found in the black tea extract. The observation that galloyl ester groups of theaflavins can be oxidized to form di- or tri-benzotropolone skeletons strongly implied that this type of oxidation is an important pathway to extend the molecular size of thearubigins. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.03.027
• 作为产物：
  描述：

  (-)-表儿茶素没食子酸酯 、 (-)-表没食子儿茶素没食子酸酯 在 polyphenol oxidase 作用下， 反应 6.0h， 生成 8-姜酚
  参考文献：
  名称：

  Benzotropolone derivatives and modulation of inflammatory response

  摘要：

  本发明提供了一种由通式表示的新型苯并三酮衍生物： 包括新茶黄素B和EGCGCa。本发明的苯并三酮衍生物是有效的抗氧化剂和抗炎药物。本发明还提供了一种高产率合成苯并三酮化合物的新方法，以及使用含有苯并三酮的化合物治疗炎症症状的方法。

  公开号：

  US20050049284A1

文献信息

• CATALYST FOR SYNTHESIZING THEAFLAVINS AND METHOD FOR SYNTHESIZING THEAFLAVINS
  申请人：NBC MESHTEC INC.

  公开号：US20170158660A1

  公开（公告）日：2017-06-08

  The objective/problem addressed by the present invention is to provide a novel technique pertaining to theaflavins synthesis. The present invention pertains to: a theaflavins synthesis catalyst characterized in having a base comprising an inorganic material, and metal nanoparticles anchored to the base, said particles measuring 0.5-100 nm in diameter; and a theaflavins synthesis method in which the catalyst is used.

  本发明解决的目标/问题是提供一种关于茶黄素合成的新技术。本发明涉及：一种茶黄素合成催化剂，其特征在于具有基体，该基体包括无机材料，并且金属纳米粒子锚定在基体上，所述粒子直径为0.5-100纳米；以及一种使用该催化剂的茶黄素合成方法。
• Synthesis of theaflavins with Camellia sinensis cell culture and inhibition of increase in blood sugar values in high-fat diet mice subjected to sucrose or glucose loading
  作者：Masumi Takemoto、Hiroaki Takemoto、Asuka Sakurada

  DOI：10.1016/j.tetlet.2014.07.092

  日期：2014.9
• Enzymatic synthesis of tea theaflavin derivatives and their anti-inflammatory and cytotoxic activities
  作者：Shengmin Sang、Joshua D Lambert、Shiying Tian、Jungil Hong、Zhe Hou、Jae-He Ryu、Ruth E Stark、Robert T Rosen、Mou-Tuan Huang、Chung S Yang、Chi-Tang Ho

  DOI：10.1016/j.bmc.2003.10.024

  日期：2004.1

  Derivatives based on a benzotropolone skeleton (9-26) have been prepared by the enzymatic coupling (horseradish peroxidase/H2O2) of selected pairs of compounds (1-8), one with a vic-trihydroxyphenyl moiety, and the other with an ortho-dihydroxyphenyl structure. Some of these compounds have been found to inhibit TPA-induced mice ear edema, nitric oxide (NO) synthesis, and arachidonic acid release by LPS-stimulated RAW 264.7 cells. Their cytotoxic activites against KYSE 150 and 510 human esophageal squamous cell carcinoma and HT 29 human colon cancer cells were also evaluated. (C) 2003 Elsevier Ltd. All rights reserved.
• Specificity of tyrosinase-catalyzed synthesis of theaflavins
  作者：Asako Narai-Kanayama、Aya Kawashima、Yuuka Uchida、Miho Kawamura、Tsutomu Nakayama

  DOI：10.1016/j.molcatb.2017.03.009

  日期：2016.11
• Chemical studies of the antioxidant mechanism of theaflavins: radical reaction products of theaflavin 3,3′-digallate with hydrogen peroxide
  作者：Shengmin Sang、Shiying Tian、Jin-woo Jhoo、Hsin Wang、Ruth E Stark、Robert T Rosen、Chung S Yang、Chi-Tang Ho

  DOI：10.1016/s0040-4039(03)01382-0

  日期：2003.7

  The objective of the current study is to characterize the reaction products of theaflavin 3,3'-digallate, one of the major characteristic polyphenols of black tea, with hydroxyl radicals generated by hydrogen peroxide, with the aim of gaining insights into specific mechanisms of antioxidant reactions in physiological systems. Two major reaction products were isolated and identified using high-field 1D and 2D NMR spectral analysis. Both of them are A-ring fission products. The observation of these compounds indicates that the A ring rather than the benzotropolone moiety is the initial site for formation of reaction products in the hydrogen peroxide oxidant system. (C) 2003 Elsevier Ltd. All rights reserved.