姜黄素葡糖苷酸 | 387818-26-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二芳基庚烷
• 中文名称: 姜黄素葡糖苷酸
• 英文名称: curcumin glucuronide
• 英文别名: curcumin-1-O-glucopyranoside；curcumin 4'-O-β-D-glucoside；(1E,6E)-1-(4-hydroxy-3-methoxyphenyl)-7-[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]hepta-1,6-diene-3,5-dione
• CAS: 387818-26-0
• 化学式: C₂₇H₃₀O₁₁
• 分子量: 530.529
• InChiKey: LVMBIHPDKVZZOB-QEYJFTPBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  38
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  glucose 、 姜黄素 在 Rhizopus chinensis IFFI 3043 作用下， 反应 24.0h， 生成 4,4'-di-O-(β-D-glucopyranosyl)curcumin 、 姜黄素葡糖苷酸 、 dihydrocurcumin-O-glucoside 、 octahydrocurcumin-O-glucoside 、 hexahydrocurcumin-O-glucoside 、 六氢姜黄素 、 四氢姜黄素 、 八氢姜黄素 、 dihydrocurcumin 、 (1E,6E)-1,7-bis(4-hydroxy-3-methoxyphenyl)hepta-1,6-diene-3,5-diol
  参考文献：
  名称：

  Microbial transformation of curcumin byRhizopus chinensis

  摘要：

  Curcumin (1) is a potent antioxidant and antitumor natural product. In spite of its efficacy and safety, its clinical use is hindered mainly by poor water solubility and bioavailability. Structural modification to introduce hydrophilic functions is a promising approach to resolve this problem. In the present study we first found that curcumin could be efficiently converted into glucosides by filamentous fungi including Rhizopus chinensis IFFI 03043, Absidia coerulea AS 3.3389 and Cunninghamella elegans AS 3.1207. Curcumin 4'-O-beta-D-glucoside (2), together with hexahydrocurcumin (3), was isolated from a preparative-scale biotransformation with R. chinensis IFFI 03043 and characterized fully by NMR and MS. A time-course study revealed that curcumin could be efficiently converted into curcumin 4'-O-beta-D-glucoside within 8 h when administered at 0.05 mmol L-1 and the productivity was 57%. Additionally, the biotransformation products of curcumin by different fungal strains were analyzed by LC/MS. At least 15 metabolites were detected, and the predominant biotransformation reaction was glucosylation. This study provides a simple, efficient and less expensive approach for the preparation of curcumin glucosides. The introduction of the glucosyl function might be able to enhance the bioavailability of curcumin.

  DOI：

  10.3109/10242422.2010.532870

文献信息

• Cannabinoid glycoside prodrugs and methods of synthesis
  申请人：Graphium Biosciences, Inc.

  公开号：US11207414B2

  公开（公告）日：2021-12-28

  The present invention relates to cannabinoid glycoside prodrugs suitable for site- and tissue-specific delivery of cannabinoid molecules. The present invention also relates to methods of forming the cannabinoid glycoside prodrugs through glycosyltransferase mediated glycosylation of cannabinoid molecules.

  本发明涉及适用于大麻素分子部位和组织特异性递送的大麻素苷原药。本发明还涉及通过糖基转移酶介导的大麻素分子糖基化形成大麻素苷原药的方法。
• CANNABINOID GLYCOSIDE PRODRUGS AND METHODS OF SYNTHESIS
  申请人：Graphium Biosciences, Inc.

  公开号：US20220168428A1

  公开（公告）日：2022-06-02

  The present invention relates to cannabinoid glycoside prodrugs suitable for site- and tissue-specific delivery of cannabinoid molecules. The present invention also relates to methods of forming the cannabinoid glycoside prodrugs through glycosyltransferase mediated glycosylation of cannabinoid molecules.