2α-veratrylmethyl-3α-piperonylmethyl-γ-butyrolactone | 126452-80-0

• 分子结构分类: 有机化合物 - 木脂素、新木脂素和相关化合物 - 呋喃类木脂素
• 英文名称: 2α-veratrylmethyl-3α-piperonylmethyl-γ-butyrolactone
• 英文别名: (3S,4R)-4-(1,3-benzodioxol-5-ylmethyl)-3-[(3,4-dimethoxyphenyl)methyl]oxolan-2-one
• CAS: 126452-80-0
• 化学式: C₂₁H₂₂O₆
• 分子量: 370.402
• InChiKey: IYBDDRJHJMFFBB-HOTGVXAUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  63.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  isokaerophyllin 在 盐酸 、 palladium on activated charcoal 氢气 作用下， 以 氯仿 、 苯 为溶剂， 反应 87.0h， 生成 2α-veratrylmethyl-3α-piperonylmethyl-γ-butyrolactone
  参考文献：
  名称：

  Isokaerophyllin，来自柴胡的丁内酯

  摘要：

  摘要 从柴胡叶中分离得到两种苄叉-苄基-γ-丁内酯型木脂素。一种被鉴定为岩藻素，另一种被鉴定为顺式异构体，迄今未见报道。通过光谱化学方法和对其衍生物的研究，后者被表征为 2(3,4-二甲氧基)-苯亚甲基-3-(3,4-二氧甲基)-苯基甲基-3 S-γ-丁内酯。

  DOI：

  10.1016/0031-9422(90)85146-7

文献信息

• Trypanocidal structure–activity relationship for cis- and trans-methylpluviatolide
  作者：R. da Silva、J. Saraiva、S. de Albuquerque、C. Curti、P.M. Donate、T.N.C. Bianco、J.K. Bastos、M.L.A. Silva

  DOI：10.1016/j.phytochem.2008.04.002

  日期：2008.6

  The trypanocidal activity of racemic mixtures of cis- and trans-methylpluviatolides was evaluated in vitro against trypomastigote forms of two strains of Trypanosoma cruzi, and in the enzymatic assay of T. cruzi gGAPDH. The cytotoxicity of the compounds was assessed by the MTT method using LLC-MK2 cells. The effect of the compounds on peroxide and NO production were also investigated. The mixture of the trans stereoisomers displayed trypanocidal activity (IC50 similar to 89.3 mu M). Therefore, it was separated by chiral HPLC, furnishing the and (+) (-)-enantiomers. Only the (-)-enantiomer was active against the parasite (IC50 similar to 18.7 mu M). Despite being inactive, the (+)-enantiomer acted as an antagonistic competitor. Trans-methylpluviatolide displayed low toxicity for LLC-MK2 cells, with an IC50 of 6.53 mM. Furthermore, methylpluviatolide neither inhibited gGAPDH activity nor hindered peroxide and NO production at the evaluated concentrations. (C) 2008 Elsevier Ltd. All rights reserved.
• Isokaerophyllin, a butyrolactone from Bupleurum salicifolium
  作者：Antonio G. González、Rafael Estévez-Reyes、Carmen Mato、Ana Ma Estévez-Braun

  DOI：10.1016/0031-9422(90)85146-7

  日期：1990.1

  Abstract From the leaves of Bupleurum salicifolium two benzylidene-benzyl-γ-butyrolactone-type lignans were isolated. One was identified as kaerophyllin, the other as its cis-isomer, hitherto unreported. The latter was characterized as 2(3,4-dimethoxy)-benzylidene-3-(3,4-dioxymethyl)-phenylmethyl-3 S-γ-butyrolactone by spectroscopic chemical methods, and from a study of its derivatives.

  摘要 从柴胡叶中分离得到两种苄叉-苄基-γ-丁内酯型木脂素。一种被鉴定为岩藻素，另一种被鉴定为顺式异构体，迄今未见报道。通过光谱化学方法和对其衍生物的研究，后者被表征为 2(3,4-二甲氧基)-苯亚甲基-3-(3,4-二氧甲基)-苯基甲基-3 S-γ-丁内酯。