1,6-二羟基-8-甲氧基-3-甲基蒽-9,10-二酮 | 3774-64-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 中文名称: 1,6-二羟基-8-甲氧基-3-甲基蒽-9,10-二酮
• 中文别名: 1,6-二羟基-8-甲氧基-3-甲基蒽-9,1-二酮
• 英文名称: questin
• 英文别名: 1,6-dihydroxy-8-methoxy-3-methylanthracene-9,10-dione；1.6-dihydroxy-8-methoxyl-3-methyl anthraquinone；1,6-dihydroxy-8-methoxy-3-methylanthraquinone；emodin 8-O-methyl ether；1-O-methylemodin；8-O-methylemodin
• CAS: 3774-64-9
• 化学式: C₁₆H₁₂O₅
• 分子量: 284.268
• InChiKey: UUNPIWCQMVNINR-UHFFFAOYSA-N

物化性质

• 熔点：
  301-303 °C
• 沸点：
  557.0±50.0 °C(Predicted)
• 密度：
  1.448±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  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：
  0.12
• 拓扑面积：
  83.8
• 氢给体数：
  2
• 氢受体数：
  5

安全信息

• 海关编码：
  2914690090
• 储存条件：
  室温

制备方法与用途

奎斯汀是从海洋黄曲霉中分离得到的一种抗菌剂，对 Vibrio harveyi、Vibrio 等鳗鲡属细菌以及副溶血性弧菌具有较强的抑制作用，其 MIC 值分别为 31.25 µg/mL、62.5 µg/mL 和 62.5 µg/mL/125 µg/mL。

反应信息

• 作为反应物：
  描述：

  1,6-二羟基-8-甲氧基-3-甲基蒽-9,10-二酮 在 氢溴酸 作用下， 以 溶剂黄146 为溶剂， 反应 6.0h， 生成 大黄素
  参考文献：
  名称：

  Enhancement of Emodin Production by Medium Optimization and KH2PO4 Supplementation in Submerged Fermentation of Marine-Derived Aspergillus favipes HN4-13

  摘要：

  大黄素是一种广泛分布的蒽醌衍生物，具有多种生物活性，并且可以由海洋源真菌Aspergillus favipes HN4-13高效产生。然而，它的相对低的发酵产量限制了进一步的开发和药物研究工作。本研究采用Plaekett-Burman设计和中心组合设计来优化A. favipes HN4-13的发酵条件。在250毫升Erlenmeyer瓶中，50毫升培养基的最佳发酵条件为：可溶性淀粉59.3克/升，酵母提取物10克/升，海水盐30克/升，KH2PO4 1.04克/升，MgSO4·7H2O 0.05克/升，FeSO4·7H2O 0.01克/升，种子培养24小时，pH 5，接种量18％，培养温度32℃，摇床速度160rpm/min，发酵7天。大黄素的产量可以达到132.40±3.09毫克/升，与预测值（132.47毫克/升）没有显著差异。此外，采用KH2PO4补充策略来调节菌丝形态，上调生物合成基因簇的转录水平，并增强大黄素的产量（185.56±4.39毫克/升）。

  DOI：

  10.3390/md19080421
• 作为产物：
  描述：

  1-氯-4,7-二羟基-5-甲氧基-2-甲基蒽-9,10-二酮 在 sodium hydroxide 、 sodium dithionite 作用下， 以 乙醇 为溶剂， 生成 1,6-二羟基-8-甲氧基-3-甲基蒽-9,10-二酮
  参考文献：
  名称：

  Banville,J.; Brassard,P., Journal of the Chemical Society. Perkin transactions I, 1976, p. 1852 - 1856

  摘要：

  DOI：

文献信息

• METHODS OF DESIGNING, PREPARING, AND USING NOVEL PROTONOPHORES
  申请人：Martineau Louis C.

  公开号：US20140135359A1

  公开（公告）日：2014-05-15

  The present invention provides a computer-assisted method of generating a protonophore requiring the use of a computer including a processor. The method includes: designing the protonophore, calculating, using the processor, an estimated protonophoric activity; producing the protonophore if the estimated protonophoric activity corresponds to an U 50 of about 20 μM or less; and determining the uncoupling activity of the protonophore. The present invention also provides novel protonophores that meet the above requirement and their methods of use.

  本发明提供了一种利用计算机辅助的方法来生成需要使用处理器的质子载体。该方法包括：设计质子载体，使用处理器计算估计的质子载体活性；如果估计的质子载体活性对应于大约20微米或更少的U50，则生产质子载体；并确定质子载体的解耦活性。本发明还提供了符合上述要求的新型质子载体及其使用方法。
• Studies on metabolites produced by Aspergillus terreus var. aureus. I. Chemical structures and antimicrobial activities of metabolites isolated from culture broth.
  作者：YOSHIHIKO INAMORI、YOSHIAKI KATO、MAYURI KUBO、TERUO KAMIKI、TSUNEMATSU TAKEMOTO、KYOSUKE NOMOTO

  DOI：10.1248/cpb.31.4543

  日期：——

  A fungus which was identified as Aspergillus terreus var. aureus showed antifungal and antibacterial activities. Through the investigation of its metabolites, six compounds (1-6) were isolated ; emodin (1), dihydrogeodin (2), questin (3), sulochrin (5), the new metabolite 2-(3-chloro-4-methyl-γ-resorcyloyl)-5-hydroxy-m-anisic acid methyl ester (4), which is a monochloro derivative of sulochrin (5), and compound (6), the chemical structure of which has not yet been clarified. Dihydrogeodin (2), sulochrin (5), 4 and 6 showed antifungal and antibacterial activities, and 6 had especially strong antifungal activity towards Trichophyton mentagrophytes.

  经鉴定，该真菌为土曲霉变种，具有抗真菌和抗细菌活性。通过对其代谢物的研究，分离出了六种化合物（1-6）：大黄素（1）、二氢大黄素（2）、喹啉（3）、舒洛钦（5）、新代谢物 2-(3-氯-4-甲基-γ-去甲环基)-5-羟基-间甲氧基苯甲酸甲酯（4）（是舒洛钦（5）的单氯衍生物）以及化合物（6），后者的化学结构尚未明确。二氢鬼臼毒素（2）、舒洛钦（5）、4 和 6 具有抗真菌和抗细菌活性，其中 6 对脑毛癣菌具有特别强的抗真菌活性。
• New metabolic products of Aspergillus flavus. Part II. Asperflavin, anhydroasperflavin, and 5,7-dihydroxy-4-methylphthalide
  作者：John Frederick Grove

  DOI：10.1039/p19720002406

  日期：——

  Asperflavin, a yellow pigment from the culture filtrate of an entomogenous strain of Aspergillus flavus, is shown to be (+)-3,4-dihydro-3,6,9-trihydroxy-8-methoxy-3-methylanthracen-1 (2H)-one (I; R = H). New minor metabolic products isolated were anhydroasperflavin (1,6-dihydroxy-8-methoxy-3-methyl-9-anthrone)(III; R1= R3= H, R2= Me) and a lactone, shown to be 5,7-dihydroxy-4-methylphthalide (VIII;

  黄曲霉毒素是黄曲霉属昆虫致病菌株培养滤液中的黄色颜料，显示为（+）-3,4-二氢-3,6,9-三羟基-8-甲氧基-3-甲基蒽-1（2 H）一（I； R = H）。分离出的新的次要代谢产物是脱水灰黄素（1,6-二羟基-8-甲氧基-3-甲基-9-蒽酮）（III； R 1 = R 3 = H，R 2 = Me）和内酯，显示为5 ，7-二羟基-4-甲基邻苯二甲酰亚胺（VIII； R 1＝ R 2＝ H）。黄色的孢子头含有已知的真菌色素曲霉精（XII； R = nC 5 H 11 ·CH：CH·）和黄霉素（XII； R = nC 7 H 15）的混合物。
• 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.