berberrubine 9-O-β-D-glucopyranoside | 1310544-33-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 原小檗碱生物碱及其衍生物
• 英文名称: berberrubine 9-O-β-D-glucopyranoside
• 英文别名: berberrubine-9-O-β-D-glucuronide
• CAS: 1310544-33-2
• 化学式: C₂₅H₂₆NO₉
• 分子量: 484.483
• InChiKey: SJWILIZCDUEBQF-ABMICEGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.27
• 重原子数：
  35.0
• 可旋转键数：
  4.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  130.95
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  小檗碱 在 碳酸氢钠 、 sodium carbonate 、 potassium carbonate 作用下， 以 甲醇 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 berberrubine 9-O-β-D-glucopyranoside
  参考文献：
  名称：

  Synthesis of 9-O-glycosyl-berberine derivatives and bioavailability evaluation

  摘要：

  To increase the bioavailability of berberine, three new 9-O-glycosyl-berberine derivatives, 9-O-glucosyl-(4a), 9-O-arabinosyl-(4b), and 9-O-erythrol-(4c) were obtained and confirmed by UV, (HNMR)-H-1, (CNMR)-C-13, and MS. The pharmacokinetic profiles of these synthetic compounds have been evaluated compared with berberine (1) and 9-O-alkyl-berberine (5) derivatives, which showed that maximum concentration (C (max)) and area under concentration-time curve (AUC) of 9-O-glycosyl-berberine increased dramatically. The results indicated that hydrophilic modification could significantly improve the bioavailability of berberine; 9-O-glycosyl-berberine might be a promising prodrug.

  DOI：

  10.1007/s00044-011-9678-1

文献信息

• Enzymatic biosynthesis of benzylisoquinoline alkaloid glycosides via promiscuous glycosyltransferases from Carthamus tinctorius
  作者：Yujiao Zhang、Kebo Xie、Aijing Liu、Ridao Chen、Dawei Chen、Lin Yang、Jungui Dai

  DOI：10.1016/j.cclet.2018.05.010

  日期：2019.2

  Abstract Enzymatic glycosylation catalyzed by glycosyltransferases (GTs) has great potential in creating diverse novel and bioactive glycosides. Herein, three new GTs (UGT84A33, UGT71AE1 and UGT90A14) from Carthamus tinctorius exhibited robust catalytic promiscuity to benzylisoquinoline alkaloids, and were used as enzymatic tools in glycosylation of bioactive benzylisoquinoline alkaloids. Seven novel benzylisoquinoline

  摘要糖基转移酶（GTs）催化的酶促糖基化具有创造各种新颖的生物活性糖苷的巨大潜力。本文中，来自红花的三个新的GT（UGT84A33，UGT71AE1和UGT90A14）对苄基异喹啉生物碱表现出强大的催化混杂性，并被用作生物活性苄基异喹啉生物碱糖基化的酶促工具。高效合成了七个新颖的苄基异喹啉生物碱O-糖苷。这些研究表明，混杂GTs在合成苄基异喹啉生物碱糖苷中具有巨大的潜力，可用于药物开发。