1,4,6-trihydroxy-2-methoxy-7-methylanthracene-9,10-dione

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: 1,4,6-trihydroxy-2-methoxy-7-methylanthracene-9,10-dione
• 英文别名: 3,5,8-trihydroxy-7-methoxy-2-methylanthracene-9,10-dione
• 化学式: C₁₆H₁₂O₆
• 分子量: 300.268
• InChiKey: ORHOPRCDKRZBSX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 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：
  104
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  1,4,6-trihydroxy-2-methoxy-7-methylanthracene-9,10-dione 、 乙酸酐 在 吡啶 作用下， 以 丙酮 为溶剂， 反应 4.0h， 以9 mg的产率得到8-acetoxy-3,5-dihydroxy-7-methoxy-2-methylanthracene-9,10-dione
  参考文献：
  名称：

  Antibacterial Anthraquinone Derivatives from a Sea Anemone-Derived Fungus Nigrospora sp.

  摘要：

  Chemical investigation of a marine-derived fungus Nigrospora sp., isolated from an unidentified sea anemone, yielded two new hydroanthraquinone analogues, 4a-epi-9 alpha-methoxydihydrodeoxybostrycin (1) and 10-deoxybostrycin (2), together with seven known anthraquinone derivatives (3-9). The structures of the two new compounds were established through extensive NMR spectroscopy as well as a single-crystal X-ray diffraction analysis using Cu K alpha radiation. The antibacterial activities of compounds 1-9 and 10 acetyl derivatives (6a, 7a, 8a-8g, 9a) were evaluated in vitro. Compound 6a, the acetylated derivative of 6, exhibited promising activity against Bacillus cereus with an MIC value of 48.8 nM, which was stronger than that of the positive control ciprofloxacin (MIC = 1250 nM). Analysis of the antibacterial screening data for the metabolites and their acetyl derivatives revealed the key structural features required for this activity.

  DOI：

  10.1021/np300103w
• 作为产物：
  描述：

  alterporriol F 在 sodium dithionite 、 sodium hydroxide 作用下， 以2 mg的产率得到巨孢子素
  参考文献：
  名称：

  猪瘟链霉菌的新抗肿瘤真菌代谢产物。

  摘要：

  对洋葱病原性真菌Alternaria porri的化学研究导致分离出了两种新的邻苯二甲酸酯，分别称为zinnimide（2）和deprenylzinnimide（8），以及一种新的比蒽醌，Alterporriol F（10）。通过光谱分析和化学降解来表征新代谢物的结构。在分离出的新化合物中，甲三醇F对HeLa和KB细胞具有高度细胞毒性，IC 50值为6.5和7.0 µg mL -1。

  DOI：

  10.1080/14786410802265415

文献信息

• TOMM6-INTERACTING EXTRACTS AND COMPOUNDS FOR USE IN THE TREATMENT AND PROPHYLAXIS OF NERVOUS SYSTEM DISEASES, ATHEROSCLEROSIS, HEPATITIS B INFECTION AND HUMAN PAPILLOMA VIRUS (HPV) INFECTION
  申请人：ETH Zurich

  公开号：EP3801507A2

  公开（公告）日：2021-04-14
• Antibacterial Anthraquinone Derivatives from a Sea Anemone-Derived Fungus <i>Nigrospora</i> sp.
  作者：Kai-Lin Yang、Mei-Yan Wei、Chang-Lun Shao、Xiu-Mei Fu、Zhi-Yong Guo、Ru-Fang Xu、Cai-Juan Zheng、Zhi-Gang She、Yong-Cheng Lin、Chang-Yun Wang

  DOI：10.1021/np300103w

  日期：2012.5.25

  Chemical investigation of a marine-derived fungus Nigrospora sp., isolated from an unidentified sea anemone, yielded two new hydroanthraquinone analogues, 4a-epi-9 alpha-methoxydihydrodeoxybostrycin (1) and 10-deoxybostrycin (2), together with seven known anthraquinone derivatives (3-9). The structures of the two new compounds were established through extensive NMR spectroscopy as well as a single-crystal X-ray diffraction analysis using Cu K alpha radiation. The antibacterial activities of compounds 1-9 and 10 acetyl derivatives (6a, 7a, 8a-8g, 9a) were evaluated in vitro. Compound 6a, the acetylated derivative of 6, exhibited promising activity against Bacillus cereus with an MIC value of 48.8 nM, which was stronger than that of the positive control ciprofloxacin (MIC = 1250 nM). Analysis of the antibacterial screening data for the metabolites and their acetyl derivatives revealed the key structural features required for this activity.
• New antitumour fungal metabolites from<i>Alternaria porri</i>
  作者：Preecha Phuwapraisirisan、Jakaphan Rangsan、Pongpan Siripong、Santi Tip-pyang

  DOI：10.1080/14786410802265415

  日期：2009.8.15

  investigation of the onion pathogenic fungus Alternaria porri resulted in the isolation of two new phthalides named zinnimide (2) and deprenylzinnimide (8), along with a new bianthraquinone, alterporriol F (10). The structures of the new metabolites were characterised by spectroscopic analysis and chemical degradation. Of the new compounds isolated, alterporriol F was highly cytotoxic towards HeLa and KB

  对洋葱病原性真菌Alternaria porri的化学研究导致分离出了两种新的邻苯二甲酸酯，分别称为zinnimide（2）和deprenylzinnimide（8），以及一种新的比蒽醌，Alterporriol F（10）。通过光谱分析和化学降解来表征新代谢物的结构。在分离出的新化合物中，甲三醇F对HeLa和KB细胞具有高度细胞毒性，IC 50值为6.5和7.0 µg mL -1。