(4aR)-3,4,4abeta,5,6,7,8,8alpha-八氢-8abeta-乙烯基-5beta-羟基-7beta-[(2-羟基甲基-1-氧代-2-丙烯基)氧基]-alpha,4-二(亚甲基)-3-氧代-1H-2-苯并吡喃-6alpha-乙酸甲酯 | 65388-17-2

• 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
• 中文名称: (4aR)-3,4,4abeta,5,6,7,8,8alpha-八氢-8abeta-乙烯基-5beta-羟基-7beta-[(2-羟基甲基-1-氧代-2-丙烯基)氧基]-alpha,4-二(亚甲基)-3-氧代-1H-2-苯并吡喃-6alpha-乙酸甲酯
• 英文名称: vernodalol
• 英文别名: [(4aR,5R,6S,7S,8aR)-8a-ethenyl-5-hydroxy-6-(3-methoxy-3-oxoprop-1-en-2-yl)-4-methylidene-3-oxo-1,4a,5,6,7,8-hexahydroisochromen-7-yl] 2-(hydroxymethyl)prop-2-enoate
• CAS: 65388-17-2
• 化学式: C₂₀H₂₄O₈
• 分子量: 392.406
• InChiKey: FZALQGCQQJLGKE-BBNZOYGDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

安全信息

• WGK Germany：
  3

反应信息

• 作为反应物：
  描述：

  (4aR)-3,4,4abeta,5,6,7,8,8alpha-八氢-8abeta-乙烯基-5beta-羟基-7beta-[(2-羟基甲基-1-氧代-2-丙烯基)氧基]-alpha,4-二(亚甲基)-3-氧代-1H-2-苯并吡喃-6alpha-乙酸甲酯 、 巯基乙胺 以 氘代二甲亚砜 为溶剂， 反应 0.17h， 生成
  参考文献：
  名称：

  Poly-Electrophilic Sesquiterpene Lactones from Vernonia amygdalina: New Members and Differences in Their Mechanism of Thiol Trapping and in Bioactivity

  摘要：

  In addition to known compounds, the leaves of Vernonia amygdalina afforded the new sesquiterpene lactones 14-O-methyl-vernolide (2), 3'-deoxyvernodalol (6), and vernomygdalin (8). These and related compounds were evaluated for modulation of a series of thiol trapping-sensitive transcription factors (NF-kappa B, STAT3, and Nrf2), involved in the maintenance of the chronic inflammatory condition typical of human degenerative diseases. Vernolide (1) emerged as a potent inhibitor of STAT3 and NF-kappa B and showed cytostatic activity toward the prostate cancer cell line DU45, arresting the cell cycle at the S phase. The exomethylene lactones are characterized by multiple Michael acceptor sites, as exemplified by vernolide (1) and vernodalol (5). By using the nuclear magnetic resonance-based cysteamine assay, the most reactive thiophilic site could be identified in both compounds, and competitive experiments qualified vernolide (1) as being more thiophilic than vernodalol (5), in agreement with the results of the pharmacological assays.

  DOI：

  10.1021/acs.jnatprod.5b00179