7-(6RS-hydroxy-3,7-dimethyl-2E,7-octadienyloxy)coumarin | 882853-97-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 7-(6RS-hydroxy-3,7-dimethyl-2E,7-octadienyloxy)coumarin
• 英文别名: 7-(6′-hydroxy-3′,7′-dimethyl-2′E,7′-octadienyloxy)coumarin；7-(6-hydroxy-3,7-dimethyl-2E,7-octadienyloxy)coumarin；7-(6′S-hydroxy-3′,7′-dimethyl-2′E,7′-octadienyloxy) coumarin；7-[(6-Hydroxy-3,7-dimethyl-2,7-octadienyl)oxy]-2H-1-benzopyran-2-one；7-[(2E)-6-hydroxy-3,7-dimethylocta-2,7-dienoxy]chromen-2-one
• CAS: 882853-97-6
• 化学式: C₁₉H₂₂O₄
• 分子量: 314.381
• InChiKey: OWAQHJLCKMIPKB-GXDHUFHOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  甲氧基-三氟甲基苯 、 7-(6RS-hydroxy-3,7-dimethyl-2E,7-octadienyloxy)coumarin 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 6.0h， 生成 、
  参考文献：
  名称：

  Sortase A-Inhibitory Coumarins from the Folk Medicinal Plant Poncirus trifoliata

  摘要：

  Thirteen coumarins (1-13), including five new compounds (1-5), were isolated from the folk medicinal plant Poncirus trifoliata. Combined spectroscopic analyses revealed that coumarins 1-4 are bis-isoprenylated coumarins with diverse oxidation patterns, while 5 is an enantiomeric di-isoprenylated coumarin. The absolute configurations of the stereogenic centers in the isoprenyl chains were assigned through MTPA and MPA methods, and those of the known compounds triphasiol (6) and ponciol (7) were also assigned using similar methods. These coumarins inhibited significantly Staphylococcus aureus-derived sortase A (SrtA), a transpeptidase responsible for anchoring surface proteins to the peptidoglycan cell wall in Gram-positive bacteria. The present results obtained indicated that the bioactivity and underlying mechanism of action of these coumarins are associated with the inhibition of SrtA-mediated S. aureus adhesion to eukaryotic cell matrix proteins including fibrinogen and fibronectin, thus potentially serving as SrtA inhibitors.

  DOI：

  10.1021/acs.jnatprod.0c00551
• 作为产物：
  描述：

  橙皮油内酯 生成 7-(6RS-hydroxy-3,7-dimethyl-2E,7-octadienyloxy)coumarin
  参考文献：
  名称：

  来自柑橘八角果汁油的 7-羟基香豆素衍生物

  摘要：

  摘要 从柑橘八角全果的汁油中分离得到3个新的7-羟基香豆素衍生物，其结构确定为7-(6R-羟基-3,7-二甲基-2E,7-辛二烯氧基)香豆素， (±)-7-羟基-6-芳樟基香豆素和(R)-6-O-(4-香叶氧基-2-羟基)肉桂基香豆素的光谱数据和化学证据。

  DOI：

  10.1016/0031-9422(92)80291-l

文献信息

• 7-Hydroxycoumarin derivatives from the juice oil of Citrus hassaku
  作者：Toshiya Masuda、Yukari Muroya、Nobuji Nakatani

  DOI：10.1016/0031-9422(92)80291-l

  日期：1992.4

  Abstract Three new 7-hydroxycoumarin derivatives have been isolated from the juice oil of whole fruits of Citrus hassaku , and their structures determined to be 7-(6 R -hydroxy-3,7-dimethyl-2 E ,7-octadienyloxy)coumarin, (±)-7-hydroxy- 6-linalylcoumarin and ( R )-6- O -(4-geranyloxy-2-hydroxy)cinnamoylmarmin by spectral data and chemical evidence.

  摘要 从柑橘八角全果的汁油中分离得到3个新的7-羟基香豆素衍生物，其结构确定为7-(6R-羟基-3,7-二甲基-2E,7-辛二烯氧基)香豆素， (±)-7-羟基-6-芳樟基香豆素和(R)-6-O-(4-香叶氧基-2-羟基)肉桂基香豆素的光谱数据和化学证据。
• Sortase A-Inhibitory Coumarins from the Folk Medicinal Plant <i>Poncirus trifoliata</i>
  作者：Jae-Sung Park、Beomkoo Chung、Won-Hee Lee、Jayho Lee、Youngbae Suh、Dong-Chan Oh、Ki-Bong Oh、Jongheon Shin

  DOI：10.1021/acs.jnatprod.0c00551

  日期：2020.10.23

  Thirteen coumarins (1-13), including five new compounds (1-5), were isolated from the folk medicinal plant Poncirus trifoliata. Combined spectroscopic analyses revealed that coumarins 1-4 are bis-isoprenylated coumarins with diverse oxidation patterns, while 5 is an enantiomeric di-isoprenylated coumarin. The absolute configurations of the stereogenic centers in the isoprenyl chains were assigned through MTPA and MPA methods, and those of the known compounds triphasiol (6) and ponciol (7) were also assigned using similar methods. These coumarins inhibited significantly Staphylococcus aureus-derived sortase A (SrtA), a transpeptidase responsible for anchoring surface proteins to the peptidoglycan cell wall in Gram-positive bacteria. The present results obtained indicated that the bioactivity and underlying mechanism of action of these coumarins are associated with the inhibition of SrtA-mediated S. aureus adhesion to eukaryotic cell matrix proteins including fibrinogen and fibronectin, thus potentially serving as SrtA inhibitors.