cymopol quinone | 65372-75-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: cymopol quinone
• CAS: 65372-75-0
• 化学式: C₁₆H₁₉BrO₂
• 分子量: 323.23
• InChiKey: IVHXCOGOXKVYLL-KPKJPENVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.43
• 重原子数：
  19.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  34.14
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  cymopol quinone 在 sodium dithionite 作用下， 以 水 、 丙酮 为溶剂， 生成 cymopol
  参考文献：
  名称：

  Organocopper chemistry of quinone bisketals. Application to the synthesis of isoprenoid quinone systems

  摘要：

  DOI：

  10.1021/jo01291a002
• 作为产物：
  描述：

  在 盐酸 作用下， 以 水 、 丙酮 为溶剂， 反应 24.0h， 生成 cymopol quinone
  参考文献：
  名称：

  Organocopper chemistry of quinone bisketals. Application to the synthesis of isoprenoid quinone systems

  摘要：

  DOI：

  10.1021/jo01291a002

文献信息

• [EN] SEAWEED EXTRACTS, ISOLATED COMPOUNDS, AND METHODS OF TREATMENT<br/>[FR] EXTRAITS D'ALGUES, COMPOSÉS ISOLÉS ET PROCÉDÉS DE TRAITEMENT
  申请人：UNIV FLORIDA

  公开号：WO2019113383A1

  公开（公告）日：2019-06-13

  The instant invention relates to seaweed extract compositions, processes for isolation, isolated active agents, and methods of treating disease, disorders and conditions in a subject, including, reactive oxygen species (ROS)-mediated diseases and diseases mediated through the activation of the Nrf2-ARE (antioxidant response element) pathway, including proliferative diseases and disorders, Alzheimer's disease, stroke, and certain diseases and disorders of aging and associated with aging and exposure, by use of the extracts, compounds, and compositions thereof.

  本发明涉及海藻提取物组合物、隔离工艺、隔离的活性成分以及治疗受试者疾病、疾病和病情的方法，包括通过使用提取物、化合物和其组合物治疗反应性氧化物种（ROS）介导的疾病和通过激活Nrf2-ARE（抗氧化剂反应元素）途径介导的疾病，包括增殖性疾病和疾病、老年痴呆症、中风以及与老化和暴露相关的某些疾病和疾病。
• Seaweed natural products modify the host inflammatory response via Nrf2 signaling and alter colon microbiota composition and gene expression
  作者：Michelle S. Bousquet、Ranjala Ratnayake、Jillian L. Pope、Qi-Yin Chen、Fanchao Zhu、Sixue Chen、Thomas J. Carney、Raad Z. Gharaibeh、Christian Jobin、Valerie J. Paul、Hendrik Luesch

  DOI：10.1016/j.freeradbiomed.2019.09.013

  日期：2020.1

  Seaweeds are an important component of human diets, especially in Asia and the Pacific islands, and have shown chemopreventive as well as anti-inflammatory properties. However, structural characterization and mechanistic insight of seaweed components responsible for their biological activities are lacking. We isolated cymopol and related natural products from the marine green alga Cymopolia barbata and demonstrated their function as activators of transcription factor Nrf2-mediated antioxidant response to increase the cellular antioxidant status. We probed the reactivity of the bioactivation product of cymopol, cymopol quinone, which was able to modify various cysteine residues of Nrf2's cytoplasmic repressor protein Keap1. The observed adducts are reflective of the polypharmacology at the level of natural product, due to multiple electrophilic centers, and at the amino acid level of the cysteine-rich target protein Keap1. The non-polar C. barbata extract and its major active component cymopol, reduced inflammatory gene transcription in vitro in macrophages and mouse embryonic fibroblasts in an Nrf2-dependent manner. Cymopol-containing extracts attenuated neutrophil migration in a zebrafish tail wound model. RNA-seq analysis of colonic tissues of mice exposed to non-polar extract or cymopol showed an antioxidant and anti-inflammatory response, with more pronounced effects exhibited by the extract. Cymopolia extract reduced DSS-induced colitis as measured by fecal lipocalin concentration. RNA-seq showed that mucosal-associated bacterial composition and transcriptional profile in large intestines were beneficially altered to varying degrees in mice treated with either the extract or cymopol. We conclude that seaweed-derived compounds, especially cymopol, alter Nrf2-mediated host and microbial gene expression, thereby providing poly-pharmacological effects.