(-)-(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl acetate | 183209-70-3

• 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: (-)-(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl acetate
• 英文别名: (-)-epigallocatechin-3-O-acetate；[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] acetate
• CAS: 183209-70-3
• 化学式: C₁₇H₁₆O₈
• 分子量: 348.309
• InChiKey: CIIQJQVSSOFPFE-NVXWUHKLSA-N

物化性质

• 沸点：
  648.6±55.0 °C(Predicted)
• 密度：
  1.67±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (-)-(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl acetate 在 咪唑 、 potassium carbonate 作用下， 以 甲醇 为溶剂， 生成 (-)-epigallocatechin penta(tertbutyldimethylsilyl)ether
  参考文献：
  名称：

  构效关系对多酚抑制人5α-还原酶的影响

  摘要：

  摘要类固醇5α-还原酶（EC 1.3.99.5）催化NADPH依赖性的多种3-oxo-Δ4类固醇双键双键还原，包括将睾丸激素转化为5α-二氢睾丸激素。在人类中，5α-还原酶活性对于男性性别分化的某些方面至关重要，并且可能参与良性前列腺增生，脱发，多毛症和前列腺癌的发展。某些天然产物包含的成分是5α-还原酶的抑制剂，例如绿茶儿茶素（-）-表没食子儿茶素没食子酸酯（EGCG）。EGCG在无细胞状态下显示出有效的抑制作用，但在5α-还原酶的全细胞分析中却没有。用长链脂肪酸代替EGCG中的没食子酸酯可产生有效的5α-还原酶抑制剂，该抑制剂在无细胞和全细胞分析系统中均具有活性。作为15α-还原酶有效抑制剂的其他类黄酮包括杨梅素，槲皮素，黄ical素和非瑟定。与1型同工酶相比，Biochanin A，黄豆苷元，染料木黄酮和山emp酚是2型抑制剂更好的抑制剂。几种其他天然和合成的多酚化合物比1型同功酶更

  DOI：

  10.1016/s0006-2952(02)00848-1
• 作为产物：
  描述：

  (-)-表没食子儿茶素 在 吡啶 、 5%-palladium/activated carbon 、 氢气 、 potassium carbonate 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 35.0h， 生成 (-)-(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl acetate
  参考文献：
  名称：

  茶儿茶素降低胆固醇的胶束溶解度的分子机制

  摘要：

  茶多酚通过降低胆固醇的胶束溶解度来降低血液中的胆固醇水平。为阐明该机制，研究了牛磺胆酸与（-）-表没食子儿茶素没食子酸酯（EGCg）及其衍生物之间的相互作用。13 C NMR研究表明，羰基碳原子以及没食子酰基部分中的1''-和4''-位置发生了显着的化学位移变化。此外，使用（-）-EGCg衍生物的1 H NMR研究表明，B环上的羟基数目不影响这些相互作用，而羰基碳原子和没食子酰基部分的芳环则具有显着影响。在儿茶素的2-和3-位上的构型也影响这些相互作用，与反式构型比顺构型产生更强的抑制活性。此外，通过电喷雾电离质谱法测定了儿茶素-牛磺胆酸络合物的1：1组分比。这些分子机制有助于胆固醇吸收抑制剂的发展。

  DOI：

  10.1021/acs.jafc.9b02265

文献信息

• 一类羟基肉桂酰酯型儿茶素的制备方法和用途
  申请人：安徽农业大学

  公开号：CN111233810B

  公开（公告）日：2023-03-21

  本发明涉及一类羟基肉桂酰酯型儿茶素的制备方法及其应用。该类羟基肉桂酰酯型儿茶素包括名称分别为表儿茶素反式香豆酸酯、表儿茶素反式咖啡酸酯、表没食子儿茶素反式香豆酸酯与表没食子儿茶素反式咖啡酸酯的4种儿茶素。该4种羟基肉桂酰酯型儿茶素由表儿茶素和表没食子儿茶素通过全乙酰化、脱去酚羟基上的乙酰基、酚羟基硅烷化及脱去3位乙酰基四个步骤后再分别与乙酰化的咖啡酸或者香豆酸的酰氯进行酯化、脱去保护基后制得，本发明4种儿茶素的制备方法简单，条件温和，在一般实验条件下即可完成。该4种羟基肉桂酰酯型儿茶素对α‑葡萄糖苷酶活性有一定抑制作用，可以用于降血糖药物，对农业和医药领域具有重要的意义。
• Semi-synthesis and proteasome inhibition of <scp>D</scp>-ring deoxy analogs of (–)-epigallocatechin gallate (EGCG), the active ingredient of green tea extract
  作者：Congde Huo、Guoqing Shi、Wai Har Lam、Di Chen、Quizhi Cindy Cui、Q Ping Dou、Tak Hang Chan

  DOI：10.1139/v07-141

  日期：2008.6.1

  A semi-synthetic route to the D-ring analogs of (–)-epigallocatechin gallate (EGCG) from the relatively abundant (–)-epigallocatechin (EGC), isolated from green tea leaves, is described. A natural product (13), found in Cistus salvifolius, its acetate (14) and analog (17) were synthesized by this method. Their inhibitory activities against proteasomes were investigated.Key words: green tea, (–)-epigallocatechin gallate (EGCG), (–)-epigallocatechin (EGC), proteasome inhibition.

  本文描述了从绿茶叶中分离出的相对丰富的(-)-表没食子儿茶素(EGC)中获得(-)-表没食子儿茶素没食子酸酯(EGCG)D环类似物的半合成路线。用这种方法合成了肉苁蓉（Cistus salvifolius）中的一种天然产物（13）及其醋酸盐（14）和类似物（17）。关键词：绿茶；(-)-表没食子儿茶素没食子酸酯（EGCG）；(-)-表没食子儿茶素（EGC）；蛋白酶体抑制。
• Optical Imaging Contrast Agents for Imaging Lung Cancer
  申请人：Klaveness Jo

  公开号：US20080044350A1

  公开（公告）日：2008-02-21

  The invention provides contrast agents for optical imaging of prostate cancer in patients. The contrast agents may be used in diagnosis of prostate cancer, for follow up of progress in disease development, for follow up of treatment of prostate cancer and for surgical guidance. Further, the invention provides methods for optical imaging of prostate cancer in patients.

  该发明提供了用于患者前列腺癌的光学成像对比剂。这些对比剂可用于前列腺癌的诊断、疾病发展进展的跟踪、前列腺癌治疗的跟踪以及手术指导。此外，该发明还提供了用于患者前列腺癌的光学成像方法。
• Production and degradation mechanism of theacitrin C, a black tea pigment derived from epigallocatechin-3-O-gallate via a bicyclo[3.2.1]octane-type intermediate
  作者：Yosuke Matsuo、Yan Li、Sayaka Watarumi、Takashi Tanaka、Isao Kouno

  DOI：10.1016/j.tet.2011.01.058

  日期：2011.3

  Black tea is rich in polyphenols and has been shown to have various health benefits: however, its components have not yet been clarified in detail. Enzymatic oxidation of epigallocatechin-3-O-gallate, the most abundant polyphenol in tea, is thought to contribute significantly to the production of black tea polyphenols. We identified theacitrin C, an unstable black tea pigment, as an enzymatic oxidation product of epigallocatechin-3-O-gallate. Degradation of theacitrin C afforded theacitrinin A and 2,3,5,7-tetrahydroxychroman-3-O-gallate. Furthermore, theacitrinin B, which was isolated from black tea, is deduced to be a degradation product of theacitrin A, the desgalloyl analogue of theacitrin C. The structures of theacitrinins A and B were elucidated based on spectroscopic data. This is the first time that a degradation product of theacitrin has been isolated from black tea. We also examined the influence of esterification of the epigallocatechin C-3 hydroxyl group on the decomposition of bicyclo[3.2.1]octane-type intermediates. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and structure–activity relationship of 3-O-acylated (–)-epigallocatechins as 5α-reductase inhibitors
  作者：Shu Fu Lin、Yu-Hsiang Lin、Mengju Lin、Yi-Feng Kao、Ru-Wen Wang、Li-Wei Teng、Shih-Hsien Chuang、Jia-Ming Chang、Ta-Tung Yuan、Kuo Chu Fu、Kuan Pin Huang、Ying-Shuen Lee、Chao-Cheng Chiang、Sheng-Chuan Yang、Chun-Liang Lai、Chu-Bin Liao、Paonien Chen、Young-Sun Lin、Kuei-Tai Lai、Hung-Jyun Huang、Ju-Ying Yang、Chia-Wei Liu、Win-Yin Wei、Chi-Kuan Chen、Richard A. Hiipakka、Shutsung Liao、Jiann-Jyh Huang

  DOI：10.1016/j.ejmech.2010.10.011

  日期：2010.12

  A series of 3-O-acylated (-)-epigallocatechins were synthesized and their inhibition of steroid 5 alpha-reductase was studied. They were prepared from the reaction of EGCG with tert-butyldimethylsilyl chloride followed by reductive cleavage of the ester bond. The resultant (-)-epigallocatechins penta-O-tert-butyldimethylsilyl ether was esterified with different fatty acids then desilylated to provide the corresponding products. The activity of 3-O-acylated (-)-epigallocatechins increased with the increasing carbon numbers of the fatty acid moiety, reaching maximum for 16 carbon atoms (compound 4h) with an IC50 of 0.53 mu M, which was similar to 12-fold more potent than EGCG (IC50 = 6.29 mu M). Introduction of monounsaturated fatty acid provided the most potent compound 6 (IC50 = 0.48 mu M), which showed moderate anti-tumor activity in vivo. (C) 2010 Elsevier Masson SAS. All rights reserved.