echinochrome A | 1471-96-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: echinochrome A
• 英文别名: echinochrome；6-ethyl-2,3,5,7,8-pentahydroxy-1,4-naphthoquinone；7-ethyl-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone；2,3,5,6,8-pentahydroxy-7-ethyl-1,4-naphthoquinone；Echinochrom A；Echinochrome A；6-ethyl-2,3,5,7,8-pentahydroxynaphthalene-1,4-dione
• CAS: 1471-96-1
• 化学式: C₁₂H₁₀O₇
• 分子量: 266.207
• InChiKey: DNRFNICCPHGYAX-UHFFFAOYSA-N

物化性质

• 熔点：
  220°C (rough estimate)
• 沸点：
  369.41°C (rough estimate)
• 密度：
  1.4726 (rough estimate)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  135
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  echinochrome A 在 oxygen 作用下， 以 丙酮 为溶剂， 反应 144.0h， 以70%的产率得到7-ethyl-2,2,3,3,5,6,8-heptahydroxy-2,3-dihydro-1,4-naphthoquinone
  参考文献：
  名称：

  7-乙基-2,3,5,6,8-pentahydroxy-1,4-naphthoquinone (echinochrome A) 被大气氧氧化 1. dehydroechinochrome 的结构

  摘要：

  7-乙基-2,3,5,6,8-五羟基-1,4-萘醌在不同溶剂（丙酮、二恶烷）中被地面大气氧（三重态 3Σg–）和激发态（单重态 1Δg）无损氧化，乙醇，乙醇水溶液，水）在室温下涉及 7-乙基-5,6,8-三羟基-2,3-二氧-2,3-二氢-1,4-萘醌（脱氢棘皮色素）的初始形成将 H2O2 分子释放到反应介质中。脱氢棘皮色素对水合作用非常敏感，连续与两个 H2O 分子反应形成 7-乙基-2,2,3,3,5,6,8-七羟基-2,3-二氢-1,4-萘醌作为相对稳定的最终产品。以这种形式，它可以从反应产物的混合物中分离出来。

  DOI：

  10.1007/s11172-018-2071-1
• 作为产物：
  描述：

  Methyl-γ-(2,3,4,5-tetramethoxyphenyl)butyrat 在 氢氧化钾 、 potassium tert-butylate 、 氢溴酸 、 氧气 、 溶剂黄146 作用下， 生成 echinochrome A
  参考文献：
  名称：

  382.自然产生的醌。第六部分 Spinochrome D. 2,3

  摘要：

  DOI：

  10.1039/jr9650002141

文献信息

• DMSO-mediated transformation of 3-amino-2-hydroxynaphthazarins to natural 2,3-dihydroxynaphthazarins and related compounds
  作者：Nikita S. Polonik、Sergey G. Polonik

  DOI：10.1016/j.tetlet.2016.06.056

  日期：2016.7

  A general and convenient method for the synthesis of naturally occurring and related hydroxylated naphthazarins has been developed. This protocol involves the oxidative DMSO-mediated transformation of 3-amino-2-hydroxynaphthazarins to 2,3-dihydroxynaphthazarins under acidic conditions. Based upon experimental observations, a plausible reaction mechanism is proposed.

  已经开发了用于合成天然存在的和相关的羟基化萘萘沙林的通用且方便的方法。该方案涉及在酸性条件下将DMSO介导的3-氨基-2-羟基萘萘氧化为2,3-二羟基萘萘。基于实验观察，提出了合理的反应机理。
• Isolation and Structure Determination of Echinochrome A Oxidative Degradation Products
  作者：Natalia P. Mishchenko、Elena A. Vasileva、Andrey V. Gerasimenko、Valeriya P. Grigorchuk、Pavel S. Dmitrenok、Sergey A. Fedoreyev

  DOI：10.3390/molecules25204778

  日期：——

  degradation products formed during oxidation by O2 in air-equilibrated aqueous solutions were identified, isolated, and structurally characterized. An HPLC method coupled with diode-array detection (DAD) and mass spectrometry (MS) was developed and validated to monitor the Ech A degradation process and identify the appearing compounds. Five primary oxidation products were detected and their structures were

  Echinochrome A (Ech A, 1) 是几种海胆物种的主要色素之一，在俄罗斯药典中注册为活性药物物质 (Histochrome®)，用于心脏病学和眼科领域。在本研究中，对空气平衡水溶液中 O2 氧化过程中形成的 Ech A 降解产物进行了鉴定、分离和结构表征。开发并验证了结合二极管阵列检测 (DAD) 和质谱 (MS) 的 HPLC 方法，用于监测 Ech A 降解过程并识别出现的化合物。检测到五种初级氧化产物，并基于高分辨率电喷雾电离质谱（HR-ESI-MS）提出了它们的结构：7-乙基-2,2,3,3,5,7,8-七羟基- 2,3-二氢-1,4-萘醌(2)、6-乙基-5,7,8-三羟基-1,2,3,4-四氢萘-1,2,3,4-四酮(3)、 2,3-环氧-7-乙基-2,3-二氢-2,3,5,6,8-五羟基-1,4-萘醌 (4), 2,3,4,5,7-五羟基-6 -乙基茚-1-酮(5)和2
• Antiviral Potential of Sea Urchin Aminated Spinochromes against Herpes Simplex Virus Type 1
  作者：Natalia P. Mishchenko、Natalia V. Krylova、Olga V. Iunikhina、Elena A. Vasileva、Galina N. Likhatskaya、Evgeny A. Pislyagin、Darya V. Tarbeeva、Pavel S. Dmitrenok、Sergey A. Fedoreyev

  DOI：10.3390/md18110550

  日期：——

  Herpes simplex virus type 1 (HSV-1) is one of the most prevalent pathogens worldwide requiring the search for new candidates for the creation of antiherpetic drugs. The ability of sea urchin spinochromes—echinochrome A (EchA) and its aminated analogues, echinamines A (EamA) and B (EamB)—to inhibit different stages of HSV-1 infection in Vero cells and to reduce the virus-induced production of reactive oxygen species (ROS) was studied. We found that spinochromes exhibited maximum antiviral activity when HSV-1 was pretreated with these compounds, which indicated the direct effect of spinochromes on HSV-1 particles. EamB and EamA both showed the highest virucidal activity by inhibiting the HSV-1 plaque formation, with a selectivity index (SI) of 80.6 and 50.3, respectively, and a reduction in HSV-1 attachment to cells (SI of 8.5 and 5.8, respectively). EamA and EamB considerably suppressed the early induction of ROS due to the virus infection. The ability of the tested compounds to directly bind to the surface glycoprotein, gD, of HSV-1 was established in silico. The dock score of EchA, EamA, and EamB was −4.75, −5.09, and −5.19 kcal/mol, respectively, which correlated with the SI of the virucidal action of these compounds and explained their ability to suppress the attachment and penetration of the virus into the cells.

  单纯疱疹病毒1型（HSV-1）是全球最常见的病原体之一，需要寻找新的候选药物来创造抗单纯疱疹药物。研究了海胆刺色素 - 刺胭脂A（EchA）及其氨基化类似物刺胭脂胺A（EamA）和B（EamB）抑制Vero细胞中HSV-1感染的不同阶段以及减少病毒诱导的活性氧（ROS）产生的能力。我们发现，当HSV-1经过这些化合物的预处理时，刺色素表现出最大的抗病毒活性，这表明刺色素对HSV-1颗粒具有直接影响。EamB和EamA通过抑制HSV-1斑疹形成表现出最高的病毒灭活活性，分别具有选择性指数（SI）为80.6和50.3，并减少HSV-1附着于细胞上（分别为8.5和5.8的SI）。EamA和EamB显著抑制了病毒感染早期ROS的诱导。通过体外模拟，建立了被测试化合物直接结合到HSV-1表面糖蛋白gD的能力。EchA，EamA和EamB的对接得分分别为-4.75，-5.09和-5.19 kcal / mol，与这些化合物的灭活作用的SI相关，并解释了它们抑制病毒附着和穿透细胞的能力。
• Diversity of Polyhydroxynaphthoquinone Pigments in North Pacific Sea Urchins
  作者：Elena A. Vasileva、Natalia P. Mishchenko、Sergey A. Fedoreyev

  DOI：10.1002/cbdv.201700182

  日期：2017.9

  composition of polyhydroxynaphthoquinone (PHNQ) pigments from sea urchins Strongylocentrotus pallidus, St. polyacanthus, St. droebachiensis, Brisaster latifrons and Echinarachnius parma, collected in the Sea of Okhotsk and the Bering Sea. Identification of PHNQ pigments from sea urchins St. polyacanthus, B. latifrons, and E. parma was performed for the first time. Among the usual PHNQ pigments, mono‐ and

  我们使用带有二极管阵列检测器和质谱法的高效液相色谱法 (HPLC-DAD/MS) 研究了海胆 Strongylocentrotus pallidus、St. polyacanthus、St. droebachiensis、Brisaster latifrons 和 Echinarachnius parma 中聚羟基萘醌 (PHNQ) 色素的组成，收集于鄂霍次克海和白令海。首次从海胆 St. polyacanthus、B. latifrons 和 E. parma 中鉴定出 PHNQ 色素。在常见的 PHNQ 色素中，在 St. polyacanthus 和 St. droebachiensis 中发现了以前在其他海胆中没有发现的刺色素 E 的单和二甲氧基衍生物。在 St. droebachiensis 中，检测到两种棘色素 A 的单甲氧基衍生物，以前仅从热带海胆中分离出来。研究发现，St.
• A simple synthesis of natural spinazarins and their analogues
  作者：Dmitry N. Pelageev、Ksenia L. Borisova、Svetlana M. Kovach、Vyacheslav V. Makhankov、Victor Ph. Anufriev

  DOI：10.1016/j.mencom.2023.02.026

  日期：2023.3

  simple synthesis of spinazarins (2,3-dihydroxy-naphthazarins or 2,3,5,8-tetrahydroxy-1,4-naphtho-quinones) from available 2,3-dichloronaphthazarin derivatives involves replacement of chlorine atoms with azido groups followed by their acidic hydrolysis. The procedure can be used for the preparative synthesis of natural biologically active spinazarins and their analogues.

  从可用的 2,3-二氯萘并衍生物中简单合成 spinazarin（2,3-二羟基-萘并或 2,3,5,8-四羟基-1,4-萘并醌）涉及用叠氮基取代氯原子，然后通过它们的酸性水解。该程序可用于天然生物活性菠菜素及其类似物的制备合成。