Kanzonol U | 178330-48-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 2-芳基苯并呋喃类黄酮
• 英文名称: Kanzonol U
• 英文别名: glabrocoumarone A；8-(6-hydroxy-1-benzofuran-2-yl)-2,2-dimethylchromen-5-ol
• CAS: 178330-48-8
• 化学式: C₁₉H₁₆O₄
• 分子量: 308.334
• InChiKey: SJIZTMNAKZAOTA-UHFFFAOYSA-N

物化性质

• 沸点：
  402.1±45.0 °C(Predicted)
• 密度：
  1.295±0.06 g/cm3(Predicted)
• 物理描述：
  Solid
• 熔点：
  192-194°C

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  23
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  62.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  重氮甲烷 、 Kanzonol U 生成 glabrocoumarone A dimethyl ether
  参考文献：
  名称：

  The Isolation of New Pyrano-2-arylbenzofuran Derivatives from the Root of Glycyrrhiza glabra.

  摘要：

  Two new pyrano-2-arylbenzofuran derivatives named glabrocoumarones A and B were isolated from commercially available licorice of Glycyrrhiza glabra origin, and thier structures were elucidated as 4'-6-dihydroxy-[6", 6"-dimethylpyrano(2", 3" : 2', 3')]-2-arylbenzofuran and 2', 6-dihydroxy-[6", 6"-dimethylpyrano(2", 3" : 4', 3')]-2-aryl-benzofuran, respectively, on the basis of spectroscopic evidence. Six known compounds were also obtained and identified spectroscopically as glabrol, 3-hydroxygrabrol, shinflavanone, [6", 6"-dimethylpyrano(2", 3" : 7, 8)]-[6''', 6'''-dimethylpyrano(2''', 3''' : 4', 3')]-flavanone (xambioona), 3, 3'-di-γ, γ-dimethylallyl-2'-4, 4'-trihydroxychalcone and [6", 6"-dimethylpyrano(2", 3" : 4, 5)]-3'-γ, γ-dimethylallyl-2', 3, 4'-trihydroxychalcone.

  DOI：

  10.1248/cpb.44.1218

文献信息

• Regio- and Stereospecific<i>O</i>-Glycosylation of Phenolic Compounds Catalyzed by a Fungal Glycosyltransferase from<i>Mucor hiemalis</i>
  作者：Jin Feng、Peng Zhang、Yinglu Cui、Kai Li、Xue Qiao、Ying-Tao Zhang、Shu-Ming Li、Russell J. Cox、Bian Wu、Min Ye、Wen-Bing Yin

  DOI：10.1002/adsc.201601317

  日期：2017.3.20

  promiscuity of the new phenolic O‐glycosyltransferase was explored by using phenols from Traditional Chinese Medicinal herbs as substrates. MhGT1 exhibited robust capabilities for the regio‐ and stereospecific O‐glycosylation of 72 structurally diverse drug‐like scaffolds and sterols with uridine diphosphate (UDP) glucose as a sugar donor. Unprecedentedly, MhGT1 showed higher regiospecificities and activities

  糖基化的小分子通常具有生物活性，主要通过微生物的生物转化（尤其是真菌）获得。但是，丝状真菌中尚未发现负责任的糖基化基因/酶。我们在这里报告的第一个鉴定的酚糖基转移酶MhGT1来自毛藻。以中国传统中草药中的酚类为底物，探索了新型酚O-糖基转移酶的底物混杂性。MhGT1具有针对区域和立体定向O的强大功能用尿苷二磷酸（UDP）葡萄糖作为糖供体对72种结构多样的药物样支架和固醇进行糖基化。前所未有地，MhGT1对异戊烯基酚显示出更高的区域特异性和活性，而对非异戊烯基化类似物而言。MhGT1的计算模型发现了酶的N端截短的结构域，该结构域由疏水性和带电荷的氨基酸残基组成，这有助于宽泛的底物范围和对异戊二烯基化合物的区域特异性。我们的发现扩展了获得新糖基转移酶的方法，并在药物发现中有效地应用了酶法来获得糖基化化合物。