neonambiquinone B | 59903-97-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: neonambiquinone B
• 英文别名: 3-Hydroxy-2,5-bis-(4-hydroxy-phenyl)-[1,4]benzoquinone；3-Hydroxy-2,5-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione；3-hydroxy-2,5-bis(4-hydroxyphenyl)cyclohexa-2,5-diene-1,4-dione
• CAS: 59903-97-8
• 化学式: C₁₈H₁₂O₅
• 分子量: 308.29
• InChiKey: ORTPWODGUGVLNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  94.8
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3',6'-二甲氧基-[1,1':4',1''-三联苯]-2',4,4''-三醇 在 氧气 、 silica gel 、 三溴化硼 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 neonambiquinone B
  参考文献：
  名称：

  p-Terphenyls From Aspergillus sp. GZWMJZ-055: Identification, Derivation, Antioxidant and α-Glycosidase Inhibitory Activities

  摘要：

  一种内生真菌Aspergillus sp. GZWMJZ-055的固体培养物中，通过添加其寄主椴树Eucommia ulmoides的叶子，分离出一种新的（1号）和十五种已知的（2号至16号）p-三联苯。此外，从主要化合物（5号至7号）中合成了九种p-三联苯（17号至25号），其中衍生物18号、19号、21号、22号和25号是新的p-三联苯。化合物15号和16号也分别从化合物6号和7号中在硅胶存在下通过氧化环化合成。这些p-三联苯，特别是那些带有4,2′,4″-三羟基（4号至7号、20号、21号）或4,4″-二羟基-1,2,1′,2′-呋喃（15号、16号）取代核的化合物，表现出显著的抗氧化和α-葡萄糖苷酶抑制活性，并对caco-2细胞的细胞毒性较低。结果表明它们作为先导化合物或膳食补充剂，具有治疗或预防糖尿病的潜力。

  DOI：

  10.3389/fmicb.2021.654963

文献信息

• The structures of toxic metabolites of Aspergillus candidus. I. The compounds A and E, cytotoxic p-terphenyls.
  作者：CHIKAKO TAKAHASHI、KUNITOSHI YOSHIHIRA、SHINSAKU NATORI、MAKOTO UMEDA

  DOI：10.1248/cpb.24.613

  日期：——

  The metabolites, compounds A-E, were isolated from a toxic strain of Aspergillus candidus and the structures of the characteristic cytotoxic compounds A (terphenyllin) and E (deoxyterphenyllin) were elucidated to p-terphenyl derivatives (1 and 24) by spectral data, oxidation reactions, and synthesis of compound A trimethyl ether. The cytotoxicity of the compounds and the derivatives was also discussed.

  通过光谱数据、氧化反应和化合物 A 三甲基醚的合成，阐明了特征性细胞毒性化合物 A（三苯乙烯）和 E（脱氧三苯乙烯）的结构，即对三苯乙烯衍生物（1 和 24）。此外，还讨论了这些化合物及其衍生物的细胞毒性。
• Design, semisynthesis, α-glucosidase inhibitory, cytotoxic, and antibacterial activities of p-terphenyl derivatives
  作者：Xue-Qing Zhang、Xiao-Feng Mou、Ning Mao、Jie-Jie Hao、Ming Liu、Ji-Yong Zheng、Chang-Yun Wang、Yu-Cheng Gu、Chang-Lun Shao

  DOI：10.1016/j.ejmech.2018.01.057

  日期：2018.2

  Terphenyllin (1), a naturally abundant p-terphenyl metabolite, was isolated from the coral derived fungus Aspergillus candidus together with four natural analogues 2-5. To evaluate their potency and selectivity, a series of new derivatives of 1 were designed and semisynthesized. They were evaluated for their alpha-glucosidase inhibitory, cytotoxic, and antibacterial activities. Compounds 1, 3, 4, 7, 8, 10, 11, 14, 15, 21, 23, 24, 29, 39, and 40 showed significant a-glucosidase inhibitory activity with IC50 values of 4.79-15 mu M, which were stronger than that of the positive controls, 1-deoxynojirimycin (IC50 = 192.0 mu M) and acarbose (IC50 = 707,9 mu M). Compounds 7 and 10 have relatively higher therapeutic indices (CC50/IC50 = 17 and 10, respectively), representing potential promising leads. The enzyme kinetic studies of compounds I and 24 showed a non-competitive inhibition on a-glucosidase with Ki values of 1.50 and 3.45 mu M, respectively. Additionally, compounds 14, 21, 26, 29, 32, 35, and 37 were found to exhibit strong cytotoxicity against three tumor cell lines A549 (lung adenocarcinoma epithelial), HeLa (cervical carcinoma), and HepG2 (hepatocellular liver carcinoma) with IC50 values ranging from 0.15 to 5.26 mu M. Further study indicated that 32 could induce S-phase arrest in the cell cycle progression. (C) 2018 Elsevier Masson SAS. All rights reserved.
• p-Terphenyls From Aspergillus sp. GZWMJZ-055: Identification, Derivation, Antioxidant and α-Glycosidase Inhibitory Activities
  作者：Yanchao Xu、Yong Wang、Dan Wu、Wenwen He、Liping Wang、Weiming Zhu

  DOI：10.3389/fmicb.2021.654963

  日期：——

  One new (1) and fifteen known (2–16) p-terphenyls were isolated from a solid culture of the endophytic fungus Aspergillus sp. GZWMJZ-055 by adding the leaves of its host Eucommia ulmoides. Furthermore, nine p-terphenyls (17–25) were synthesized from the main compounds (5–7), among which derivatives 18, 19, 21, 22, and 25 are new p-terphenyls. Compounds 15 and 16 were also, respectively, synthesized from compounds 6 and 7 by oxidative cyclization of air in the presence of silica gel. These p-terphenyls especially those with 4,2′,4″-trihydroxy (4–7, 20, 21) or 4, 4″-dihydroxy-1,2,1′,2′-furan (15, 16) substituted nucleus, exhibited significant antioxidant and α-glucosidase inhibitory activities and lower cytotoxicity to caco-2 cells. The results indicated their potential use as lead compounds or dietary supplements for treating or preventing the diabetes.

  一种内生真菌Aspergillus sp. GZWMJZ-055的固体培养物中，通过添加其寄主椴树Eucommia ulmoides的叶子，分离出一种新的（1号）和十五种已知的（2号至16号）p-三联苯。此外，从主要化合物（5号至7号）中合成了九种p-三联苯（17号至25号），其中衍生物18号、19号、21号、22号和25号是新的p-三联苯。化合物15号和16号也分别从化合物6号和7号中在硅胶存在下通过氧化环化合成。这些p-三联苯，特别是那些带有4,2′,4″-三羟基（4号至7号、20号、21号）或4,4″-二羟基-1,2,1′,2′-呋喃（15号、16号）取代核的化合物，表现出显著的抗氧化和α-葡萄糖苷酶抑制活性，并对caco-2细胞的细胞毒性较低。结果表明它们作为先导化合物或膳食补充剂，具有治疗或预防糖尿病的潜力。