刺蓟苦素 | 19889-00-0

• 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
• 中文名称: 刺蓟苦素
• 英文名称: onopordopicrin
• 英文别名: [(3aR,4S,6E,10Z,11aR)-10-(hydroxymethyl)-6-methyl-3-methylidene-2-oxo-3a,4,5,8,9,11a-hexahydrocyclodeca[b]furan-4-yl] 2-(hydroxymethyl)prop-2-enoate
• CAS: 19889-00-0
• 化学式: C₁₉H₂₄O₆
• 分子量: 348.396
• InChiKey: NOZAJYKZMCFNFG-WULVTUHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  刺蓟苦素 、 巯基乙胺 以 氘代二甲亚砜 为溶剂， 反应 0.08h， 生成
  参考文献：
  名称：

  Anti-inflammatory sesquiterpene lactones from Onopordum illyricum L. (Asteraceae), an Italian medicinal plant

  摘要：

  Onopordum illyricum L is a medicinal plant used in the Mediterranean area as antipyretic for the treatment of respiratory and urinary inflammations and to treat skin ulcers. Repeated chromatographic purification of O. illyricum aerial parts led to the isolation of six known sesquiterpenes, which were evaluated for the inhibition of the pro-inflammatory transcription factors NF-kappa B and STAT3 and for the activation of the transcription factor Nrf2, which regulates the cellular antioxidant response. Structure-activity relationships were interpreted by the NMR-based cysteamine assay. The sesquiterpene lactone vernomelitensin significantly inhibited NF-KB and STAT3, showing also a significant Nrf2 activation. Accordingly, the cysteamine assay selected vernomelitensin as the most reactive of the isolated sesquiterpenes, identifying the alpha,beta-unsaturated aldehyde moiety as responsible for the higher (re)activity. (C) 2016 Elsevier B.V. All rights reserved.

  DOI：

  10.1016/j.fitote.2016.11.006

文献信息

• Anti-inflammatory sesquiterpene lactones from Onopordum illyricum L. (Asteraceae), an Italian medicinal plant
  作者：Carmen Formisano、Cinzia Sanna、Mauro Ballero、Giuseppina Chianese、Carmina Sirignano、Daniela Rigano、Estrella Millán、Eduardo Muñoz、Orazio Taglialatela-Scafati

  DOI：10.1016/j.fitote.2016.11.006

  日期：2017.1

  Onopordum illyricum L is a medicinal plant used in the Mediterranean area as antipyretic for the treatment of respiratory and urinary inflammations and to treat skin ulcers. Repeated chromatographic purification of O. illyricum aerial parts led to the isolation of six known sesquiterpenes, which were evaluated for the inhibition of the pro-inflammatory transcription factors NF-kappa B and STAT3 and for the activation of the transcription factor Nrf2, which regulates the cellular antioxidant response. Structure-activity relationships were interpreted by the NMR-based cysteamine assay. The sesquiterpene lactone vernomelitensin significantly inhibited NF-KB and STAT3, showing also a significant Nrf2 activation. Accordingly, the cysteamine assay selected vernomelitensin as the most reactive of the isolated sesquiterpenes, identifying the alpha,beta-unsaturated aldehyde moiety as responsible for the higher (re)activity. (C) 2016 Elsevier B.V. All rights reserved.