khonklonginol A | 1159909-57-5

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: khonklonginol A
• 英文别名: (7R,8R)-5,7-dihydroxy-8-(4-methoxyphenyl)-2,2-dimethyl-10-(3-methylbut-2-enyl)-7,8-dihydropyrano[3,2-g]chromen-6-one
• CAS: 1159909-57-5
• 化学式: C₂₆H₂₈O₆
• 分子量: 436.505
• InChiKey: ACXXSEDDPWHZAU-XZOQPEGZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  85.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  khonklonginol A 在 间氯过氧苯甲酸 作用下， 生成 2''',3'''-epoxykhonklonginol A
  参考文献：
  名称：

  Eriosema chinense: A rich source of antimicrobial and antioxidant flavonoids

  摘要：

  Six prenylated fiavonoids, (2R,3S)-3,5,4'-trihydroxy-6 ''-6 '' dimethylpyrano(2 '',3 '':7,6)-8-(3''', 3'''-dimethylallyl) flavanone, (2R,3S)-3,5,2'-trihydroxy-4'-methoxy-6 '',6 ''-dimethylpyrano(2 '',3 '':7,6)-8-(3''',3'''-dimethylallyl) flavanone, (2R,3R)-3,5,2',4'-tetrahydroxy-6 '',6 ''-dimethylpyrano(2 '',3 '':7,6)-8-(3''',3'''-dimethylallyl) flavanone, 3,5,2',4'-tetrahydroxy-6 '',6 ''-dimethylpyrano(2 '',3 '':7,6)-8-(3''',3'''-dimethylallyl) flavone, (2R,3R,2'''R)-3,5,2'''-trihydroxy-4'-methoxy-6 '',6 ''-dimethylpyrano(2 '',3 '':7,6)-8-(3'''-methylbut-3"-enyl)flavanone, (2R,3R)-3,5-dihydroxy-4'-methoxy-6",6"-dimethylpyrano(2 '',3 '':7,6)-8-(2''',3'''-epoxy-3'''-methyl butyl)flavanone, an isoflavone, 6,7-dimethoxy-5,2',4'-trihydroxyisoflavone, and octaeicosanyl-trans-p-coumarate together with 12 known compounds, were isolated from roots of Eriosema chinense. This structural elucidation was determined by spectroscopic methods. Several isolates and derivatives were evaluated for their antimicrobial and antioxidant activities. Results obtained provide additional evidence showing that the presence of both the free phenolic OH and the lipophilic prenyl groups are crucial for potent antimicrobial activity against yeast, gram positive and gram negative bacteria, whereas the presence of free phenolic OH group is required for strong radical scavenging property. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.phytochem.2013.06.004

文献信息

• Oximes of 3-Hydroxyprenylflavanones and Their Cytotoxic Activities
  作者：Somyote Sutthivaiyakit、Ranu Sawangsri、Korakot Navakhun、Jantana Yahuafai、Pongpun Siripong、Sanit Thongnest

  DOI：10.3987/com-12-12568

  日期：——

  Oximination of 3-hydroxyprenylflavanones using hydroxylamine hydrochloride yielded 4-hydroxy-3-oxime and 3-hydroxy-4-oxime derivatives. The 3 beta-O-acetylhydroxyprenylflavanones, under similar reaction condition, yielded corresponding 4-O-acetyl-3-oximes. The configurations at C-4 of the 4-hydroxy-3-oximes obtained from both 3 alpha- and 3 beta-hydroxyprenylflavanones and of 4-O-acetyl-3-oxime derivative from 3 beta-O-aeetylprenylflavanones were proposed. Cytotoxic activities of the oximes and their parent compounds were evaluated against a panel of human cancer cell lines.