cytosporone C

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: cytosporone C
• 英文别名: 1-heptyl-6,8-dihydroxy-1,4-dihydroisochromen-3-one
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: UBUGNGHURFYFHC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  20
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-(3,5-dimethoxy-2-octanoylphenyl)acetic acid 在 aluminum (III) chloride 、 sodium tetrahydroborate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 31.0h， 生成 cytosporone C
  参考文献：
  名称：

  Total synthesis and allelopathic activity of cytosporones A-C

  摘要：

  The search for efficient, environmentally friendly herbicides has been the focus of numerous studies on the organic synthesis of compounds isolated from natural sources. Cytosporones, which are phenolic lipids isolated from fungi, exhibit noteworthy biological properties. This paper reports the preparation of cytosporones A-C from the same starting material through a short synthetic route, with good yields. All compounds were tested for allelopathic activity on lettuce (Lactuca sativa L) seeds. Cytosporone A and its methylated precursor showed remarkable allelopathic activity, inhibiting seed germination and plantule growth.

  DOI：

  10.1590/s0103-50532012000100018

文献信息

• Syntheses of Cytosporones A, C, J, K, and N, Metabolites from Medicinal Fungi
  作者：Andrew M. Beekman、Russell A. Barrow

  DOI：10.1071/ch15144

  日期：——

  compounds for the first time. The key steps included a recently described homologation of benzoic acid to the analogous phenyl acetate using Birch reductive alkylation conditions, acylation of the appropriate phenyl acetate derivative, and a selective reduction and spontaneous biomimetic lactonization to yield the 3-isochromanone skeleton. The synthesized natural products were evaluated for their biological

  报道了真菌代谢产物细胞孢子A，（±）-C和N的合成。并首次描述了细胞孢子J和K的合成。含有稀有的3-异苯并二氢吡喃酮亚结构的天然产物外消旋细胞孢子J和外消旋细胞孢子K的制备分别以8个线性步骤进行，总产率分别为45％和7个线性步骤，产率为46％，从而完成了表征这些化合物是第一次。关键步骤包括最近描述的使用桦木还原烷基化条件将苯甲酸同化为乙酸苯酯的类似物，适当乙酸苯酯衍生物的酰化，以及选择性还原和自发仿生内酯化以生成3-isochromanone骨架。
• Water-Mediated <i>ortho</i>-Carboxymethylation of Aryl Ketones under Ir(III)-Catalytic Conditions: Step Economy Total Synthesis of Cytosporones A–C
  作者：Pitambar Patel

  DOI：10.1021/acs.joc.2c00197

  日期：2022.4.1

  Flavanone and chromanone were also found to be facile substrates with the developed catalytic system. Mechanistic studies revealed the active catalytic species and the role of water in the reaction process as hydroxy and proton sources. Employing the developed method, total synthesis of cytosporone A was achieved in two steps and that of cytosporones B–C was achieved in three steps starting from resorcinol

  已经在水性介质中开发了一种快速 Ir(III) 催化的芳基酮与重氮化 Meldrum 酸的羧甲基化反应。还发现黄烷酮和色满酮是具有开发催化体系的容易的底物。机理研究揭示了活性催化物质和水在反应过程中作为羟基和质子源的作用。采用所开发的方法，细胞孢子素 A 的全合成分两步完成，细胞孢子素 B-C 的全合成从间苯二酚开始分三步完成。
• Biosynthesis of Cytosporones in Leotiomycetous Filamentous Fungi
  作者：Li Li、Weimao Zhong、Hang Liu、Patricia Espinosa-Artiles、Ya-ming Xu、Chen Wang、Jose Manuel Verdugo Robles、Tiago Antunes Paz、Marielle Cascaes Inácio、Fusheng Chen、Yuquan Xu、A. A. Leslie Gunatilaka、István Molnár

  DOI：10.1021/jacs.3c14066

  日期：2024.3.6

  isochroman-3-one pharmacophore are rare among fungal natural products as their biosynthesis requires an unorthodox S-type aromatic ring cyclization. Genome mining uncovered a conserved gene cluster in select leotiomycetous fungi that encodes the biosynthesis of cytosporones, including isochroman-3-one congeners. Combinatorial biosynthesis in total biosynthetic and biocatalytic formats in Saccharomyces cerevisiae

  具有异色满-3-酮药效基团的聚酮化合物在真菌天然产物中很少见，因为它们的生物合成需要非正统的 S 型芳环环化。基因组挖掘在选定的leotiomycetous真菌中发现了一个保守的基因簇，该基因簇编码细胞孢子酮的生物合成，包括isochroman-3-one同源物。酿酒酵母中全生物合成和生物催化形式的组合生物合成以及使用纯化酶的关键反应的体外重建揭示了细胞孢子酮结构和生物活性多样性是如何产生的。细胞孢子酮的 S 型酰基二羟基苯乙酸 (ADA) 核心由协作的聚酮合酶对组装。硫酯酶结构域催化的酯交换反应释放 ADA 酯，其中一些是已知的 Nur77 调节剂。或者，水解释放允许 C6 通过黄素依赖性单加氧酶羟基化，产生三羟基苯部分。通过短链脱氢酶/还原酶还原 C9 羰基会引发 isochroman-3-one 形成，从而提供具有细胞毒性和抗菌活性的细胞孢子酮。烯酰二-或三羟基苯乙酸作为分流产物生成，而异可尔曼-3
• Uncovering Biosynthetic Potential of Plant-Associated Fungi: Effect of Culture Conditions on Metabolite Production by <i>Paraphaeosphaeria quadriseptata</i> and <i>Chaetomium chiversii</i>
  作者：Priyani A. Paranagama、E. M. Kithsiri Wijeratne、A. A. Leslie Gunatilaka

  DOI：10.1021/np070504b

  日期：2007.12.1

  In an attempt to uncover the biosynthetic potential of plant-associated fungi, the effect of culture conditions on metabolite production by Paraphaeosphaeria quadriseptata and Chaetomium chiversii was investigated. These studies indicated that the production of the major metabolites by P. quadriseptata differ when the water used to make the media was changed from tap water to distilled water. It resulted in the isolation of six new secondary metabolites, cytosporones F-I (1-4), quadriseptin A (5), and 5'-hydroxymonocillin III (6) together with monocillin III (7), a metabolite new to P. quadriseptata, in addition to monocillin I (8), a previously known metabolite from this organism. Aposphaerin B (9) encountered was suspected to be an artifact originating from cytosporone F (1). Incorporation of heavy metal ions to P. quadriseptata culture medium induced production of monocillin 1 (8) by this fungus. Cultivation of C. chiversii in liquid medium resulted in the isolation of chaetochromin A (12) as the major metabolite instead of radicicol (10), the major constituent of this organism when grown in a solid medium. Compounds 1-7 and 12 were evaluated for their potential to inhibit Hsp90 and antiproliferative activity toward the cancer cell lines NCI-H460, MCF-7, and SF-268. Only compounds 6, 7, and 8 exhibited significant activity in both assays.