Ω-羟基大黄素-8-甲醚 | 35688-09-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: Ω-羟基大黄素-8-甲醚
• 英文名称: questinol
• 英文别名: ω-hydroxyemodin-5-methylether；1,6-dihydroxy-3-(hydroxymethyl)-8-methoxyanthracene-9,10-dione
• CAS: 35688-09-6
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: SNBGJGNOQURXCI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  22
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  Ω-羟基大黄素-8-甲醚 在 氧气 、 dioxygenase GedK from Aspergillus terreus AT₀₁ 、 reductase GedF from Aspergillus terreus AT₀₁ 、 还原型辅酶II(NADPH)四钠盐 作用下， 以 aq. buffer 为溶剂， 反应 0.1h， 生成 hydrodesmethylsulochrin
  参考文献：
  名称：

  双酶催化和双加氧介导的蒽醌开环

  摘要：

  蒽醌的 C-10–C-4a 键断裂被认为是真菌环蒽醌生物合成的关键步骤，并且长期以来被认为是经典的 Baeyer-Villiger 氧化。尽管如此，有关开环的遗传、酶学和化学信息仍然难以捉摸。在这里，通过体内基因破坏、体外酶分析和18 O 追逐实验阐明了修订后的 questin 开环机制。已证实还原酶 GedF 负责在 NADPH 的帮助下将 questin 中 C-10 的酮基还原为羟基。生成的 questin 对苯二酚的 C-10–C-4a 键随后被非典型的无辅因子双加氧酶 GedK 裂解，产生去甲基磺酰氯。这种双酶催化和双氧化介导的蒽醌开环反应显示出普遍性。

  DOI：

  10.1021/jacs.1c07182
• 作为产物：
  描述：

  羟基大黄素 、 碘甲烷 在 硼酸 、 乙酸酐 、 potassium carbonate 、 sodium hydroxide 作用下， 生成 Ω-羟基大黄素-8-甲醚 、 carviolin
  参考文献：
  名称：

  Characterization of emodin metabolites in Raji cells by LC–APCI-MS/MS

  摘要：

  A rapid, simple, and sensitive liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry (LC-APCI-MS/MS) method was developed for the identification and quantification of emodin metabolites in Raji cells, using aloe-emodin as an internal standard. Analyses were performed on an LC system employing a Cosmosil 5C(18) AR-II column and a stepwise gradient elution with methanol-20 mM ammonium formate at a flow rate of 1.0 mL/min operating in the negative ion mode. As a result, the starting material emodin and its five metabolites were detected by analyzing extracts of Raji cells that had been cultivated in the presence of emodin. The identification of the metabolites and elucidation of their structures were performed by comparing their retention times and spectral patterns with those of synthetic samples. In addition to the major metabolite 8-O-methylemodin, four other metabolites were assigned as omega-hydroxyemodin, 3-O-methyl-omega-hydroxyemodin, 3-O-methylemodin (physcion), and chrysophanol. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2009.09.024

文献信息

• TOMM6-INTERACTING EXTRACTS AND COMPOUNDS FOR USE IN THE TREATMENT AND PROPHYLAXIS OF NERVOUS SYSTEM DISEASES, ATHEROSCLEROSIS, HEPATITIS B INFECTION AND HUMAN PAPILLOMA VIRUS (HPV) INFECTION
  申请人：ETH Zurich

  公开号：EP3801507A2

  公开（公告）日：2021-04-14
• METHODS, COMPOSITIONS, AND KITS FOR THE TREATMENT OF CANCER
  申请人：Haggerty Timothy J.

  公开号：US20140335050A1

  公开（公告）日：2014-11-13

  The invention features methods, compositions, and kits for the administration of an HSP90 inhibitor, OBAA, flunarizine, aphidicolin, damnacanthal, dantrolene, or an analog thereof, alone, or in combination with, e.g., a TAA, an antigen-binding scaffold (e.g., an antibody, a soluble T cell receptor, or a chimeric receptor) specific for a TAA, a cell (e.g., a white blood cell that targets a cancer cell), and/or an IFN-β receptor agonist or an IFN-γ receptor agonist, for the treatment of cancer.
• Bienzyme-Catalytic and Dioxygenation-Mediated Anthraquinone Ring Opening
  作者：Feifei Qi、Wei Zhang、Yingying Xue、Ce Geng、Xuenian Huang、Jia Sun、Xuefeng Lu

  DOI：10.1021/jacs.1c07182

  日期：2021.10.13

  believed to be a crucial step in fungal seco-anthraquinone biosynthesis and has long been proposed as a classic Baeyer–Villiger oxidation. Nonetheless, genetic, enzymatic, and chemical information on ring opening remains elusive. Here, a revised questin ring-opening mechanism was elucidated by in vivo gene disruption, in vitro enzymatic analysis, and 18O chasing experiments. It has been confirmed that the

  蒽醌的 C-10–C-4a 键断裂被认为是真菌环蒽醌生物合成的关键步骤，并且长期以来被认为是经典的 Baeyer-Villiger 氧化。尽管如此，有关开环的遗传、酶学和化学信息仍然难以捉摸。在这里，通过体内基因破坏、体外酶分析和18 O 追逐实验阐明了修订后的 questin 开环机制。已证实还原酶 GedF 负责在 NADPH 的帮助下将 questin 中 C-10 的酮基还原为羟基。生成的 questin 对苯二酚的 C-10–C-4a 键随后被非典型的无辅因子双加氧酶 GedK 裂解，产生去甲基磺酰氯。这种双酶催化和双氧化介导的蒽醌开环反应显示出普遍性。
• Characterization of emodin metabolites in Raji cells by LC–APCI-MS/MS
  作者：Junko Koyama、Atsuko Takeuchi、Izumi Morita、Yu Nishino、Maki Shimizu、Munetaka Inoue、Norihiro Kobayashi

  DOI：10.1016/j.bmc.2009.09.024

  日期：2009.11

  A rapid, simple, and sensitive liquid chromatography-atmospheric pressure chemical ionization tandem mass spectrometry (LC-APCI-MS/MS) method was developed for the identification and quantification of emodin metabolites in Raji cells, using aloe-emodin as an internal standard. Analyses were performed on an LC system employing a Cosmosil 5C(18) AR-II column and a stepwise gradient elution with methanol-20 mM ammonium formate at a flow rate of 1.0 mL/min operating in the negative ion mode. As a result, the starting material emodin and its five metabolites were detected by analyzing extracts of Raji cells that had been cultivated in the presence of emodin. The identification of the metabolites and elucidation of their structures were performed by comparing their retention times and spectral patterns with those of synthetic samples. In addition to the major metabolite 8-O-methylemodin, four other metabolites were assigned as omega-hydroxyemodin, 3-O-methyl-omega-hydroxyemodin, 3-O-methylemodin (physcion), and chrysophanol. (C) 2009 Elsevier Ltd. All rights reserved.