atrochrysone

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: atrochrysone
• 英文别名: 3,6,8,9-tetrahydroxy-3-methyl-2,4-dihydroanthracen-1-one
• 化学式: C₁₅H₁₄O₅
• 分子量: 274.273
• InChiKey: FELQSDLZFDTZJN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  丙二酰辅酶A-钠盐 在 A_. oryzae expressing atrochrysone carboxylic acid synthase and atrochrysone carboxyl acyl carrier protein thioesterase 作用下， 生成 atrochrysone 、 Endocrin-9-anthron 、 内黄素
  参考文献：
  名称：

  Physically Discrete β-Lactamase-Type Thioesterase Catalyzes Product Release in Atrochrysone Synthesis by Iterative Type I Polyketide Synthase

  摘要：

  ATEG_08451 in Aspergillus terreus, here named atrochrysone carboxylic acid synthase (ACAS), is a nonreducing, iterative type I polyketide synthase that contains no thioesterase domain. In vitro, reactions of ACAS with malonyl-CoA yielded a polyketide intermediate, probably attached to its acyl carrier protein (ACP). The addition of ATEG_08450, here named atrochrysone carboxyl ACP thioesterase (ACTE), to the reaction resulted in the release of products derived from atrochrysone carboxylic acid, such as atrochrysone and endocrocin. ACTE, belonging to the beta-lactamase superfamily, thus appears to be a novel type of thioesterase responsible for product release in polyketide biosynthesis. These findings show that ACAS synthesizes the scaffold of atrochrysone carboxylic acid from malonyl-CoA, and that ACTE hydrolyzes the thioester bond between the ACP of ACAS and the intermediate to release atrochrysone carboxylic acid as the reaction product.

  DOI：

  10.1016/j.chembiol.2009.04.004

文献信息

• Characterization of the <i>Aspergillus nidulans</i> Monodictyphenone Gene Cluster
  作者：Yi-Ming Chiang、Edyta Szewczyk、Ashley D. Davidson、Ruth Entwistle、Nancy P. Keller、Clay C. C. Wang、Berl R. Oakley

  DOI：10.1128/aem.02187-09

  日期：2010.4

  Deletion of cclA , a component of the COMPASS complex of Aspergillus nidulans , results in the production of monodictyphenone and emodin derivatives. Through a set of targeted deletions in a cclA deletion strain, we have identified the genes required for monodictyphenone and emodin analog biosynthesis. Identification of an intermediate, endocrocin, from an mdpH Δ strain suggests that mdpH might encode a decarboxylase. Furthermore, by replacing the promoter of mdpA (a putative aflJ homolog) and mdpE (a putative aflR homolog) with the inducible alcA promoter, we have confirmed that MdpA functions as a coactivator. We propose a biosynthetic pathway for monodictyphenone and emodin derivatives based on bioinformatic analysis and characterization of biosynthetic intermediates.

  摘要 删除 cclA 的一个组成部分 黑曲霉 会产生单二萜酮和大黄素衍生物。通过一组靶向删除 cclA 缺失菌株中的一系列定向缺失，我们确定了单苯甲酮和大黄素类似物生物合成所需的基因。我们从一株 mdpH 菌株中鉴定出了一种中间体--大黄素。 mdpH Δ 菌株中鉴定出了一种中间体--大黄素，这表明 mdpH 可能编码一种脱羧酶。此外，通过替换 mdpA (的启动子 aflJ 同源物）和 mdpE (推测的 同源物 同源物）与可诱导的 启动子 启动子，我们证实了 MdpA 作为辅助激活子的功能。根据生物信息学分析和生物合成中间体的特征，我们提出了单二萜酮和大黄素衍生物的生物合成途径。
• Elucidation of cladofulvin biosynthesis reveals a cytochrome P450 monooxygenase required for anthraquinone dimerization
  作者：Scott Griffiths、Carl H. Mesarich、Benedetta Saccomanno、Abraham Vaisberg、Pierre J. G. M. De Wit、Russell Cox、Jérôme Collemare

  DOI：10.1073/pnas.1603528113

  日期：2016.6.21

  Anthraquinones are potent secondary metabolites produced by many fungi and plants used in traditional Chinese and Indian medicine. Many display useful biological properties, including antineoplastic, antiinflammatory, antiinfective, or antiparasitic activities. The chemical structure of anthraquinones is very diverse, with many occurring as homo- and heterodimers. Anthraquinone biosynthetic pathways must be elucidated before novel structurally complex chemicals with new or enhanced biological activity can be engineered. In this study, we identified an enzyme involved in asymmetrical dimerization of nataloe-emodin, which results in increased cytotoxicity toward a range of cancer cell lines. Mastering the substrate specificity of this enzyme (and other similar enzymes) could lead to the dimerization of anthraquinone-related compounds with medicinal activities.

  蒽醌是许多真菌和植物产生的强效次生代谢物，被用于传统的中药和印度药物。许多蒽醌具有有用的生物学特性，包括抗肿瘤、抗炎、抗感染或抗寄生虫活性。蒽醌的化学结构非常多样，许多以同源和异源二聚体的形式存在。在构建具有新或增强生物活性的新型结构复杂化合物之前，必须阐明蒽醌生物合成途径。在这项研究中，我们鉴定了一种参与天然蒽醌素二聚体不对称化反应的酶，这导致对一系列癌细胞系的细胞毒性增强。掌握该酶（和其他类似酶）的底物特异性可能导致蒽醌相关化合物的二聚体化，从而具有药用活性。

• Physically Discrete β-Lactamase-Type Thioesterase Catalyzes Product Release in Atrochrysone Synthesis by Iterative Type I Polyketide Synthase
  作者：Takayoshi Awakawa、Kosuke Yokota、Nobutaka Funa、Fuminao Doi、Naoki Mori、Hidenori Watanabe、Sueharu Horinouchi

  DOI：10.1016/j.chembiol.2009.04.004

  日期：2009.6

  ATEG_08451 in Aspergillus terreus, here named atrochrysone carboxylic acid synthase (ACAS), is a nonreducing, iterative type I polyketide synthase that contains no thioesterase domain. In vitro, reactions of ACAS with malonyl-CoA yielded a polyketide intermediate, probably attached to its acyl carrier protein (ACP). The addition of ATEG_08450, here named atrochrysone carboxyl ACP thioesterase (ACTE), to the reaction resulted in the release of products derived from atrochrysone carboxylic acid, such as atrochrysone and endocrocin. ACTE, belonging to the beta-lactamase superfamily, thus appears to be a novel type of thioesterase responsible for product release in polyketide biosynthesis. These findings show that ACAS synthesizes the scaffold of atrochrysone carboxylic acid from malonyl-CoA, and that ACTE hydrolyzes the thioester bond between the ACP of ACAS and the intermediate to release atrochrysone carboxylic acid as the reaction product.