6-Hydroxygenistein | 13539-26-9

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 6-Hydroxygenistein
• 英文别名: 5,6,7,4'-tetrahydroxyisoflavone；5,6,7-trihydroxy-3-(4-hydroxyphenyl)chromen-4-one
• CAS: 13539-26-9
• 化学式: C₁₅H₁₀O₆
• 分子量: 286.241
• InChiKey: HDXSEWOOSVMREY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  107
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  6-Hydroxygenistein 在 硫酸 、 sodium chloride 作用下， 以 水 为溶剂， 反应 2.0h， 以80%的产率得到sodium 6-hydroxygenistein-5'-sulfonate
  参考文献：
  名称：

  6-羟基染料木素-5′-磺酸盐及其制备方法和用途

  摘要：

  本发明公开了一种6‑羟基染料木素‑5′‑磺酸盐及其制备方法和用途，利用6‑羟基染料木素、射干苷元和葛花苷元制备得到的6‑羟基染料木素‑5′‑磺酸盐，具有药理活性，即具有明显的抗缺氧作用，能明显延长小鼠急性脑缺血的存活时间，显著提高机体耐缺氧能力，对HCT116、MCF‑7、A549细胞株显示出一定的活性，对H2O2诱导PC12细胞损伤有显著的保护作用。可应用于制备治疗心脑血管疾病、血管性痴呆、肿瘤的药物方面，特别是可制备成注射剂、片剂、胶囊剂、滴丸剂或口服溶液等制剂使其应用范围更广。

  公开号：

  CN107417653A
• 作为产物：
  描述：

  鹰嘴豆芽素A 在 N-溴代丁二酰亚胺(NBS) 、 三溴化硼 、 potassium carbonate 、 copper(I) bromide 作用下， 以 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 22.17h， 生成 6-Hydroxygenistein
  参考文献：
  名称：

  Synthesis, Characterization, and Antiradical Activity of 6-Hydroxygenistein

  摘要：

  本研究以廉价易得的生物茶氨酸 A 为原料，通过甲基化、溴化、甲氧基化和脱甲基化，报道了一条 6-hydroxygenistein (6-OHG) 的聚合合成路线。通过质谱、红外光谱、1H NMR 和 13C NMR 分析确认了产物的结构。以抗坏血酸（VC）为阳性对照，采用六种不同的方法测定了 6-OHG 的抗自由基活性，即 DPPH 法、ABTS 法、一氧化氮法、超氧化物法、还原力法和磷钼法。结果表明，6-OHG 具有与 VC 相似或更强的抗自由基活性。总之，6-OHG 可以作为一种有用的抗氧化剂。

  DOI：

  10.1007/s10600-020-03161-5

文献信息

• Studies of the Selective O-Alkylation and Dealkylation of Flavonoids.XX. A Convenient Method for Synthesizing 5,6,7-Trihydroxyisoflavones and 5,6-Dihydroxy-7-methoxyisoflavones.
  作者：Tokunaru HORIE、Masahiro SASAGAWA、Fumihito TORII、Yasuhiko KAWAMURA、Kazuyo YAMASHITA

  DOI：10.1248/cpb.44.486

  日期：——

  3', 6'-Bis(benzyloxy)-2', 4'-dimethoxychalcones, which were derived from dibenzyl ether of 3, 6-dihydroxy-2, 4-dimethoxyacetophenone, were oxidatively rearranged with thallium(III) nitrate (TTN) in methanol to give 2-aryl-1-[3, 6-bis(benzyloxy)-2, 4-dimethoxyphenyl]-3, 3-dimethoxypropan-1-ones; these products were converted into 6-hydroxy-5, 7-dimethoxyisoflavones by hydrogenolysis followed by cyclization. The 5-methoxy group in the acetates of the isoflavones was selectively cleaved with 5% (w/v) anhydrous aluminum bromide in acetonitrile to give quantitatively the corresponding 5-hydroxyisoflavones, which were hydrolyzed to 5, 6-dihydroxy-7-methoxy-isoflavones. The acetates were also demethylated to 5, 6, 7-trihydroxyisoflavones with 30% (w/v) anhydrous aluminum chloride in acetonitrile at 70°C for 36-48 h. The spectral properties of these isoflanones were examined and some natural isoflavones were identified.

  3',6'-双(苄氧基)-2',4'-二甲氧基查尔酮，源自3,6-二羟基-2,4-二甲氧基乙酰苯酮的二苄醚，在甲醇中通过氧化性重排与硝酸铊(III)(TTN)反应，生成2-芳基-1-[3,6-双(苄氧基)-2,4-二甲氧基苯基]-3,3-二甲氧基丙酮；这些产物通过氢解后环化转化为6-羟基-5,7-二甲氧基异黄酮。异黄酮的乙酸酯中的5-甲氧基在乙腈中以5%（质量体积比）无水溴化铝选择性裂解，定量得到相应的5-羟基异黄酮，这些异黄酮再水解为5,6-二羟基-7-甲氧基异黄酮。乙酸酯还通过在70°C下乙腈中30%（质量体积比）无水氯化铝处理36-48小时脱甲基化，得到5,6,7-三羟基异黄酮。对这些异黄酮的光谱特性进行了检验，并鉴定了一些天然异黄酮。
• METHOD OF BIOTRANSFORMATION OF BENZOPYRONE COMPOUNDS INTO THE CORRESPONDING PHOSPHATE-CONJUGATED DERIVATIVES
  申请人：National Taiwan University

  公开号：US20170305944A1

  公开（公告）日：2017-10-26

  The present invention is related to a biotransformation process, effected by means of an isolated polypeptide possessing benzopyrone phosphate synthetase activity, and also a microorganism comprising a nucleic acid sequence that encodes the polypeptide, for the preparation of phosphate-conjugated derivatives of benzopyrone compounds. The hydrophilic property of the benzopyrone compounds is enhanced after catalyzed by the benzopyrone phosphate synthetase of the present invention.

  本发明涉及一种生物转化过程，通过一种具有苯并吡喃磷酸合酶活性的分离多肽实现，并且包括一种编码该多肽的核酸序列的微生物，用于制备苯并吡喃化合物的磷酸共轭衍生物。经本发明的苯并吡喃磷酸合酶催化后，苯并吡喃化合物的亲水性质得到增强。
• COMPOSITION FOR TREATING ATHEROSCLEROSIS AND A PREPARATION METHOD THEREOF
  申请人：WU YANG-CHANG

  公开号：US20130040996A1

  公开（公告）日：2013-02-14

  Disclosed are a composition for preventing and treating atherosclerosis which includes chalcone compound. In particular, the chalcone compound bound with 2-hydroxyl in ring A and 4′-methyoxy in ring B has versatile therapeutic potentials on anti-atherosclerosis by acting as PPARγ inducer, p44/42 MAPK inhibitor and cell cycle blocker and does not show toxicity to human aortic smooth muscle cells (HASMCs). In addition, the chalcone compound exhibits synergistic effect with the PPARγ ligand (rosiglitazone) to inhibit cell proliferation and the upregulation of cyclin D1, cyclin D3, interleukin-1β (IL-1β) and interleukin-6 (IL-6) induced by oxidized low density lipoprotein (Ox-LDL).

  本发明涉及一种用于预防和治疗动脉粥样硬化的组合物，其中包括查尔酮化合物。特别地，环A中与2-羟基结合，环B中与4'-甲氧基结合的查尔酮化合物具有多种治疗潜力，可作为PPARγ诱导剂、p44/42 MAPK抑制剂和细胞周期阻滞剂，且不对人体主动脉平滑肌细胞（HASMCs）显示毒性。此外，查尔酮化合物与PPARγ配体（罗格列酮）表现出协同作用，可抑制由氧化低密度脂蛋白（Ox-LDL）诱导的细胞增殖和cyclin D1、cyclin D3、白细胞介素-1β（IL-1β）和白细胞介素-6（IL-6）上调。
• Isoflavones for regulating sirtuin gene expression
  申请人：Nestec S.A.

  公开号：EP2898923A2

  公开（公告）日：2015-07-29

  The invention provides compositions useful for regulating sirtuin gene expression, mimicking caloric restriction, preventing and treating Alzheimer's disease, increasing longevity and retarding aging in an animal. The compositions comprising one or more isoflavones are to be administered to the animals, preferably in amounts of from about 0.001 to about 10 g/kg/day.

  本发明提供了可用于调节 sirtuin 基因表达、模拟热量限制、预防和治疗阿尔茨海默病、延长动物寿命和延缓衰老的组合物。包含一种或多种异黄酮的组合物将施用给动物，优选用量为约 0.001 至约 10 克/千克/天。
• Method of biotransformation of benzopyrone compounds into the corresponding phosphate-conjugated derivatives
  申请人：National Taiwan University

  公开号：US10421768B2

  公开（公告）日：2019-09-24

  The present invention is related to a biotransformation process, effected by means of an isolated polypeptide possessing benzopyrone phosphate synthetase activity, and also a microorganism comprising a nucleic acid sequence that encodes the polypeptide, for the preparation of phosphate-conjugated derivatives of benzopyrone compounds. The hydrophilic property of the benzopyrone compounds is enhanced after catalyzed by the benzopyrone phosphate synthetase of the present invention.

  本发明涉及一种生物转化过程，该过程通过一种具有吡喃苯酮磷酸合成酶活性的分离多肽和一种包含编码该多肽的核酸序列的微生物来实现，用于制备吡喃苯酮化合物的磷酸结合衍生物。经本发明的苯并吡喃酮磷酸合成酶催化后，苯并吡喃酮化合物的亲水性增强。