20-O-β-(D-glucopyranosyl)dammarenediol II

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: 20-O-β-(D-glucopyranosyl)dammarenediol II
• 英文别名: 20-O-β-D-glucopyranosyldammar-24-ene-3β,20S-diol；20-G-DM；20-O-β-(D-glucopyranosyl)-DM；(20S)-20-O-(beta-D-glucosyl)-3-hydroxydammarene；(2R,3S,4S,5R,6S)-2-(hydroxymethyl)-6-[(2S)-2-[(3S,5R,8R,9R,10R,13R,14R,17S)-3-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]-6-methylhept-5-en-2-yl]oxyoxane-3,4,5-triol
• 化学式: C₃₆H₆₂O₇
• 分子量: 606.884
• InChiKey: JQOUYGJYNQSCQP-UZTNOJNJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  43
• 可旋转键数：
  7
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  120
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  20-O-β-(D-glucopyranosyl)dammarenediol II 、 氧气 、 1-Deoxy-1-(7,8-dimethyl-2,4-dioxidobenzo[g]pteridin-10(5H)-yl)-5-O-phosphonopentitol 生成 人参皂苷CK 、 氢(+1)阳离子 、 水 、 FMN
  参考文献：
  名称：

  Production of bioactive ginsenoside compound K in metabolically engineered yeast

  摘要：

  DOI：

  10.1038/cr.2014.28
• 作为产物：
  描述：

  尿苷(5')二氢二磷酰(1)-alpha-D-葡萄糖 、 达玛烯二醇 II 在 recombinant UGTPg₁ UDP-glycosyltransferase from Panax ginseng 作用下， 以 aq. buffer 为溶剂， 反应 24.0h， 生成 20-O-β-(D-glucopyranosyl)dammarenediol II
  参考文献：
  名称：

  微生物细胞工厂的建设和优化，以可持续生产生物活性达玛烯二醇-II糖苷

  摘要：

  人参皂甙，的主要生物活性成分三七物种，被糖基化在C3-OH和/或原人参二醇的C20-OH（PPD），和C6-OH和/或原人参萜三醇的C20-OH（PPT）生物合成。PPD的直接前体Dammarenediol-II（DM）在C3和C20位置具有两个羟基，但几乎未从人参物种中鉴定出DM苷。在本文中，我们使用了两种重组粗UDP糖基转移酶（转移酶），PgUGT74AE2和UGTPg1从人参，催化DM与UDP-葡萄糖（UDPG）作为糖供体，以产生DM糖苷3-糖基化ö -β- d -吡喃葡萄糖基-dammar-24-ene-3β，20 S-二醇（3β - O -Glc-DM）和20-O - β - D-吡喃葡萄糖基-达玛-24-烯-3β，20 S-二醇（20 S-O -Glc-DM）。在体外和体内测定证明，这两个3β- ö -Glc-DM和20 S-O -Glc-DM显示出比天然人参更高的抗结肠癌活性

  DOI：

  10.1039/c8gc04066d

文献信息

• GROUP OF GLYCOSYLTRANSFERASES AND USE THEREOF
  申请人：Shanghai Institutes For Biological Sciences, Chinese Academy Of Sciences

  公开号：US20160115515A1

  公开（公告）日：2016-04-28

  Provided are the use of glycosyltransferases gGT25, gGT13, gGT30, gGT25-1, gGT25-3, gGT25-5, gGT29, gGT29-3, gGT29-4, gGT29-5, gGT29-6, gGT29-7, 3GT1, 3GT2, 3GT3, 3GT4 and derived polypeptides therefrom in the catalyzed glycosylation of terpenoid compounds and the synthesis of new saponins, wherein the glycosyltransferases can specifically and efficiently catalyze tetracyclic triterpenoid compound substrates at positions C-20 and/or C-6 and/or C-3 during hydroxyl glycosylation, and/or transfer the glycosyl from a glycosyl donor to the first glycosyl of the tetracyclic triterpenoid compounds at position C-3, so as to extend the sugar chain. The glycosyltransferases can also be used for constructing man-made synthetic rare ginsenosides and a variety of new ginsenosides and derivatives thereof.

  提供了使用糖基转移酶gGT25、gGT13、gGT30、gGT25-1、gGT25-3、gGT25-5、gGT29、gGT29-3、gGT29-4、gGT29-5、gGT29-6、gGT29-7、3GT1、3GT2、3GT3、3GT4及其衍生的多肽在催化萜类化合物的糖基化和合成新皂苷中的用途，其中糖基转移酶可以特异且高效地催化四环三萜类化合物底物在C-20和/或C-6和/或C-3位置的羟基糖基化，和/或将糖基从糖基供体转移至四环三萜类化合物在C-3位置的第一个糖基，从而延长糖链。这些糖基转移酶还可用于构建人工合成的稀有人参皂苷和各种新人参皂苷及其衍生物。
• Characterization of Panax ginseng UDP-Glycosyltransferases Catalyzing Protopanaxatriol and Biosyntheses of Bioactive Ginsenosides F1 and Rh1 in Metabolically Engineered Yeasts
  作者：Wei Wei、Pingping Wang、Yongjun Wei、Qunfang Liu、Chengshuai Yang、Guoping Zhao、Jianmin Yue、Xing Yan、Zhihua Zhou

  DOI：10.1016/j.molp.2015.05.010

  日期：2015.9

  Ginsenosides, the main pharmacologically active natural compounds in ginseng (Panax ginseng), are mostly the glycosylated products of protopanaxadiol (PPD) and protopanaxatriol (PPT). No uridine diphosphate glycosyltransferase (UGT), which catalyzes PPT to produce PPT-type ginsenosides, has yet been reported. Here, we show that UGTPg1, which has been demonstrated to regio-specifically glycosylate the C20-OH of PPD, also specifically glycosylates the C20-OH of PPT to produce bioactive ginsenoside F1. We report the characterization of four novel UGT genes isolated from P. ginseng, sharing high deduced amino acid identity (>84%) with UGTPg1. We demonstrate that UGTPg100 specifically glycosylates the C6-OH of PPT to produce bioactive ginsenoside Rh1, and UGTPg101 catalyzes PPT to produce F1, followed by the generation of ginsenoside Rg1 from F1. However, UGTPg102 and UGTPg103 were found to have no detectable activity on PPT. Through structural modeling and site-directed mutagenesis, we identified several key amino acids of these UGTs that may play important roles in determining their activities and substrate regio-specificities. Moreover, we constructed yeast recombinants to biosynthesize F1 and Rh1 by introducing the genetically engineered PPT-producing pathway and UGTPg1 or UGTPg100. Our study reveals the possible biosynthetic pathways of PPT-type ginsenosides in Panax plants, and provides a sound manufacturing approach for bioactive PPT-type ginsenosides in yeast via synthetic biology strategies.
• Construction and optimization of microbial cell factories for sustainable production of bioactive dammarenediol-II glucosides
  作者：Zong-Feng Hu、An-Di Gu、Lan Liang、Yan Li、Ting Gong、Jing-Jing Chen、Tian-Jiao Chen、Jin-Ling Yang、Ping Zhu

  DOI：10.1039/c8gc04066d

  日期：——

  L−1 20S-O-Glc-DM were achieved through fed-batch fermentation in a 3 L bioreactor. This is the first study to demonstrate the anti-colon cancer activities of DM glucosides and to achieve the de novo biosynthesis of DM glucosides with high titers in microbial cell factories. This study has established a green and sustainable approach for the industrial production of DM glucosides, which provides promising

  人参皂甙，的主要生物活性成分三七物种，被糖基化在C3-OH和/或原人参二醇的C20-OH（PPD），和C6-OH和/或原人参萜三醇的C20-OH（PPT）生物合成。PPD的直接前体Dammarenediol-II（DM）在C3和C20位置具有两个羟基，但几乎未从人参物种中鉴定出DM苷。在本文中，我们使用了两种重组粗UDP糖基转移酶（转移酶），PgUGT74AE2和UGTPg1从人参，催化DM与UDP-葡萄糖（UDPG）作为糖供体，以产生DM糖苷3-糖基化ö -β- d -吡喃葡萄糖基-dammar-24-ene-3β，20 S-二醇（3β - O -Glc-DM）和20-O - β - D-吡喃葡萄糖基-达玛-24-烯-3β，20 S-二醇（20 S-O -Glc-DM）。在体外和体内测定证明，这两个3β- ö -Glc-DM和20 S-O -Glc-DM显示出比天然人参更高的抗结肠癌活性
• Production of bioactive ginsenoside compound K in metabolically engineered yeast
  作者：Xing Yan、Yun Fan、Wei Wei、Pingping Wang、Qunfang Liu、Yongjun Wei、Lei Zhang、Guoping Zhao、Jianmin Yue、Zhihua Zhou

  DOI：10.1038/cr.2014.28

  日期：2014.6