kaempferol 7-O-β-D-(4-O-methyl) glucoside | 1092795-48-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 黄酮类化合物
• 英文名称: kaempferol 7-O-β-D-(4-O-methyl) glucoside
• 英文别名: 7-[(2S,3R,4R,5S,6R)-3,4-dihydroxy-6-(hydroxymethyl)-5-methoxyoxan-2-yl]oxy-3,5-dihydroxy-2-(4-hydroxyphenyl)chromen-4-one
• CAS: 1092795-48-6
• 化学式: C₂₂H₂₂O₁₁
• 分子量: 462.41
• InChiKey: ISZVIPCAULDCLG-SPJAQXOISA-N

物化性质

• 沸点：
  786.4±60.0 °C(Predicted)
• 密度：
  1.68±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  33
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  175
• 氢给体数：
  6
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  kaempferol 7-O-β-D-(4-O-methyl) glucoside 在 盐酸 、 水 作用下， 反应 2.0h， 生成 4-O-methyl-D-glucopyranose
  参考文献：
  名称：

  Microbial Metabolism of Biologically Active Secondary Metabolites from Nerium oleander L.

  摘要：

  熊果酸（1）和山奈酚（3）是地中海植物夹竹桃（Nerium oleander L.）的两个主要成分。黄曲霉（Aspergillus flavus，ATCC 9170）对（1）进行微生物代谢后，生成了3-氧代熊果酸衍生物——乌索酸（2）。另一方面，布拉克须霉（Cunninghamella blakesleeana，ATCC 8688A）能够将（3）转化为山奈酚3-O-β-D-吡喃葡萄糖苷（4）以及新的天然产物山奈酚4'-磺酸（5）。将山奈酚与拉曼根霉（Mucor ramannianus，ATCC 9268）共培养，分离出一种代谢物，鉴定为山奈酚4'-O-α-L-吡喃鼠李糖苷（6）。在白僵菌（Beauveria bassiana，ATCC 13144）发酵过程中，观察到山奈酚转化为新化合物山奈酚7-O-β-D-4-O-甲基吡喃葡萄糖苷（7）和草棉素8-O-β-D-吡喃葡萄糖苷（8）。测定了分离代谢物的细胞毒性和抗氧化活性。

  DOI：

  10.1248/cpb.56.1253
• 作为产物：
  描述：

  山奈酚 、 alkaline earth salt of/the/ methylsulfuric acid 以 N,N-二甲基甲酰胺 为溶剂， 反应 336.0h， 以56 mg的产率得到kaempferol 7-O-β-D-(4-O-methyl) glucoside
  参考文献：
  名称：

  Microbial Metabolism of Biologically Active Secondary Metabolites from Nerium oleander L.

  摘要：

  熊果酸（1）和山奈酚（3）是地中海植物夹竹桃（Nerium oleander L.）的两个主要成分。黄曲霉（Aspergillus flavus，ATCC 9170）对（1）进行微生物代谢后，生成了3-氧代熊果酸衍生物——乌索酸（2）。另一方面，布拉克须霉（Cunninghamella blakesleeana，ATCC 8688A）能够将（3）转化为山奈酚3-O-β-D-吡喃葡萄糖苷（4）以及新的天然产物山奈酚4'-磺酸（5）。将山奈酚与拉曼根霉（Mucor ramannianus，ATCC 9268）共培养，分离出一种代谢物，鉴定为山奈酚4'-O-α-L-吡喃鼠李糖苷（6）。在白僵菌（Beauveria bassiana，ATCC 13144）发酵过程中，观察到山奈酚转化为新化合物山奈酚7-O-β-D-4-O-甲基吡喃葡萄糖苷（7）和草棉素8-O-β-D-吡喃葡萄糖苷（8）。测定了分离代谢物的细胞毒性和抗氧化活性。

  DOI：

  10.1248/cpb.56.1253

文献信息

• Methylglucosylation of Phenolic Compounds by Fungal Glycosyltransferase-Methyltransferase Functional Modules
  作者：Linan Xie、Liwen Zhang、Jing Bai、Qun Yue、Min Zhang、Jiancheng Li、Chen Wang、Yuquan Xu

  DOI：10.1021/acs.jafc.9b02819

  日期：2019.8.7

  Glycosylation endows both natural and synthetic small molecules with modulated physicochemical and biological properties. Plant and bacterial glycosyltransferases capable of decorating various privileged scaffolds have been extensively studied, but those from kingdom Fungi still remain underexploited. Here, we use a combination of genome mining and heterologous expression techniques to identify four novel glycosyltransferase-methyltransferase (GT-MT) functional modules from Hypocreales fungi. These GT-MT modules display decent substrate promiscuity and regiospecificity, methylglucosylating a panel of natural products such as flavonoids, stilbenoids, anthraquinones, and benzenediol lactones. Native GT-MT modules can be split up and regrouped into hybrid modules with similar or even improved efficacy as compared with native pairs. Methylglucosylation of kaempferol considerably improves its insecticidal activity against the larvae of oriental armyworm Mythimna separata (Walker). Our work provides a set of efficient biocatalysts for the combinatorial biosynthesis of small molecule glycosides that may have significant importance to the pharmaceutical, agricultural, and food industries.
• Microbial Metabolism of Biologically Active Secondary Metabolites from Nerium oleander L.
  作者：Amany Ibrahim、Sherief Ibrahim Khalifa、Ishrak Khafagi、Diaa Tohamy Youssef、Shabana Khan、Mostafa Mesbah、Ikhlas Khan

  DOI：10.1248/cpb.56.1253

  日期：——

  Ursolic acid (1) and kaempferol (3) are two major constituents of the Mediterranean plant Nerium oleander L. Microbial metabolism of (1) with Aspergillus flavus (ATCC 9170) resulted in the formation of 3-oxo-ursolic acid derivative, ursonic acid (2). On the other hand, Cunninghamella blakesleeana (ATCC 8688A) was able to convert (3) into kaempferol 3-O-β-D-glucopyranoside (4) as well as the new natural product kaempferol 4′-sulfate (5). Incubation of kaempferol with Mucor ramannianus (ATCC 9628) led to the isolation of one metabolite identified as kaempferol 4′-O-α-L-rhamnopyranoside (6). Transformation of kaempferol to the new compound kaempferol 7-O-β-D-4-O-methylglucopyranoside (7) and herbacetin 8-O-β-D-glucopyranoside (8) was observed after fermentation with Beauveria bassiana (ATCC 13144). Cytotoxic as well as antioxidant activities of the isolated metabolites were determined.

  熊果酸（1）和山奈酚（3）是地中海植物夹竹桃（Nerium oleander L.）的两个主要成分。黄曲霉（Aspergillus flavus，ATCC 9170）对（1）进行微生物代谢后，生成了3-氧代熊果酸衍生物——乌索酸（2）。另一方面，布拉克须霉（Cunninghamella blakesleeana，ATCC 8688A）能够将（3）转化为山奈酚3-O-β-D-吡喃葡萄糖苷（4）以及新的天然产物山奈酚4'-磺酸（5）。将山奈酚与拉曼根霉（Mucor ramannianus，ATCC 9268）共培养，分离出一种代谢物，鉴定为山奈酚4'-O-α-L-吡喃鼠李糖苷（6）。在白僵菌（Beauveria bassiana，ATCC 13144）发酵过程中，观察到山奈酚转化为新化合物山奈酚7-O-β-D-4-O-甲基吡喃葡萄糖苷（7）和草棉素8-O-β-D-吡喃葡萄糖苷（8）。测定了分离代谢物的细胞毒性和抗氧化活性。