戈米辛J | 66280-25-9

• 物质功能分类: 天然产物 - 木脂素
• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 单宁
• 中文名称: 戈米辛J
• 英文名称: Gomisin J
• 英文别名: 3,4,15,16-tetramethoxy-9,10-dimethyltricyclo[10.4.0.02,7]hexadeca-1(16),2,4,6,12,14-hexaene-5,14-diol
• CAS: 66280-25-9
• 化学式: C₂₂H₂₈O₆
• 分子量: 388.461
• InChiKey: PICOUNAPKDEPCA-UHFFFAOYSA-N

物化性质

• 熔点：
  148-149℃
• 沸点：
  587.5±50.0 °C(Predicted)
• 密度：
  1.161
• 溶解度：
  溶于氯仿、二氯甲烷、乙酸乙酯、DMSO、丙酮等。

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  77.4
• 氢给体数：
  2
• 氢受体数：
  6

安全信息

• 危险性防范说明：
  P261,P305+P351+P338
• 危险性描述：
  H302,H315,H319,H335

制备方法与用途

生物活性

Gomisin J 是一种在五味子 (Schisandra chinensis) 中发现的小分子量木脂素，具有血管舒张活性。它通过激活 AMPK、LKB1 和 Ca²⁺/钙调蛋白依赖性蛋白激酶 II 以及抑制 HepG2 细胞中的胎球蛋白-A (fetuin-A)，调节脂肪生成、脂肪分解酶和炎症分子的表达，从而抑制脂质积累。因此，在研究非酒精性脂肪性肝病方面具有潜在益处。

靶点

• AMPK
• Ca²⁺

化学性质

Gomisin J 是一种白色粉末，可溶于甲醇、乙醇和 DMSO 等有机溶剂。它来源于南五味子。

用途

戈米辛 J 是一种很有前途的抗卵巢癌药物，并且对 SN-8 的葡萄糖醛酸化表现出强烈的抑制作用。此外，它还具有抗氧化作用。

药理药效

适用于含量测定、鉴定和药理实验等。

• 抗肿瘤
• 抑制血管收缩
• 增加冠脉血流（麻醉犬）
• 抗肝毒
• 抗氧化剂
• 保护心肌

反应信息

• 作为反应物：
  描述：

  碘甲烷 、 戈米辛J 在 potassium carbonate 作用下， 以 丙酮 为溶剂， 以4.7 mg的产率得到五味子甲素
  参考文献：
  名称：

  Identification of Key Structural Characteristics of Schisandra chinensis Lignans Involved in P-Glycoprotein Inhibition

  摘要：

  The aim of the present study was to determine the structural requirements for dibenzocyclooctadiene lignans essential for P-glycoprotein inhibition. Altogether 15 structurally related lignans isolated from Schisandra chinensis or prepared by modification of their backbone were investigated, including three pairs of enantiomers. P-Glycoprotein inhibition was quantified using a doxorubicin accumulation assay in human promyelotic leukemia HL60/MDR cells overexpressing P-glycoprotein. A preliminary quantitative structure-activity relationship analysis revealed three main structural features involved in P-glycoprotein inhibition: a 1,2,3-trimethoxy moiety, a 6-acyloxy group, and the absence of a 7-hydroxy group. The most effective inhibitors, (-)-gomisin N (1) and (+)-deoxyschizandrin [(+)-2], were selected for further evaluation of their effects. Both these lignans restored the cytotoxic effect of doxorubicin in HL60/MDR cells and when combined with a subtoxic concentration of this compound increased the proportion of G2/M cells significantly, which is a usual response to treatment with this anticancer drug.

  DOI：

  10.1021/np500521v

文献信息

• Identification of Key Structural Characteristics of <i>Schisandra chinensis</i> Lignans Involved in P-Glycoprotein Inhibition
  作者：Jiří Slanina、Gabriela Páchniková、Martina Čarnecká、Ludmila Porubová Koubíková、Lenka Adámková、Otakar Humpa、Karel Šmejkal、Iva Slaninová

  DOI：10.1021/np500521v

  日期：2014.10.24

  The aim of the present study was to determine the structural requirements for dibenzocyclooctadiene lignans essential for P-glycoprotein inhibition. Altogether 15 structurally related lignans isolated from Schisandra chinensis or prepared by modification of their backbone were investigated, including three pairs of enantiomers. P-Glycoprotein inhibition was quantified using a doxorubicin accumulation assay in human promyelotic leukemia HL60/MDR cells overexpressing P-glycoprotein. A preliminary quantitative structure-activity relationship analysis revealed three main structural features involved in P-glycoprotein inhibition: a 1,2,3-trimethoxy moiety, a 6-acyloxy group, and the absence of a 7-hydroxy group. The most effective inhibitors, (-)-gomisin N (1) and (+)-deoxyschizandrin [(+)-2], were selected for further evaluation of their effects. Both these lignans restored the cytotoxic effect of doxorubicin in HL60/MDR cells and when combined with a subtoxic concentration of this compound increased the proportion of G2/M cells significantly, which is a usual response to treatment with this anticancer drug.