parissaponin I

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 类固醇和类固醇衍生物
• 英文名称: parissaponin I
• 英文别名: parisaponin I；(2S,3R,4R,5R,6S)-2-[(2R,3R,4S,5S,6R)-5-[(2S,3R,4R,5S)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-4-hydroxy-6-(hydroxymethyl)-2-[[(1S,2S,4S,6R,7S,8R,9S,12S,13R,16S)-6-hydroxy-7,9,13-trimethyl-6-[(3R)-3-methyl-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutyl]-5-oxapentacyclo[10.8.0.02,9.04,8.013,18]icos-18-en-16-yl]oxy]oxan-3-yl]oxy-6-methyloxane-3,4,5-triol
• 化学式: C₅₀H₈₂O₂₂
• 分子量: 1035.19
• InChiKey: FAFUWLJMHOPRJO-ZZVCCQRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  72
• 可旋转键数：
  15
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  346
• 氢给体数：
  13
• 氢受体数：
  22

反应信息

• 作为反应物：
  描述：

  parissaponin I 、 蔗糖 在 enzyme of the strain from Arthrobacter nitroguajacolicus, CPCC 203516 作用下， 以 水 、 正丁醇 为溶剂， 反应 24.0h， 生成 (25R)-26-[(O-β-D-fructofuranosyl-(2→6)-β-D-glucopyranosyl)]-22α-hydroxyfurost-5-ene-3-O-α-L-arabinopyranosyl-(1→4)-[α-L-rhamnopyranosyl-(1→2)]-β-D-glucopyranoside
  参考文献：
  名称：

  Selective glycosylation of steroidal saponins by Arthrobacter nitroguajacolicus

  摘要：

  In this study seven strains of the genus Arthrobacter were screened by biotransformation to discover glycosylating patterns on steroid saponins. A strain of Arthrobacter nitroguajacolicus (CPCC 203516) was found to have the ability of fructosylation. Crude enzyme of the strain was extracted for the further study of conversion characteristics and patterns. Sucrose was used as a non-activated sugar donor, and fifteen steroidal saponins were involved. Nine furostan saponins of the substrates were converted, and ten products were isolated and identified. Based on the HR-ESI-MS, 1D, and 2D NMR spectral data, one fructosyl was added to furostan saponins at C-6-OH of 26-O-beta-D-glucopyranosyl by A. nitroguajacolicus for all nine products. One product was distinguished by an additional fructosyl at the position of C-6-OH on the first added fructosyl. Spirostan saponins of the substrates could not be converted. Steroidal saponins embracing a fructosyl are quite rare according to other reports based on similar studies. This study successfully converted furostan saponins into new compounds. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.carres.2014.07.006
• 作为产物：
  描述：

  (25R)-26-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-16β-acetoxy-22-oxo-cholest-5-en-3β-yl-O-[2-O-(2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-4-O-(2,3,5-tri-O-benzoyl-α-arabinofuranosyl)-6-O-benzoyl-β-D-glucopyranoside] 在 lithium hydroxide monohydrate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 6.0h， 以62%的产率得到parissaponin I
  参考文献：
  名称：

  呋喃甾醇糖苷的合成：一种有效的α-葡萄糖苷酶抑制剂的发现†

  摘要：

  已经开发了一种方便的合成糠醛甾醇糖苷的方法，该方法具有高效掺入26- O- β- D-吡喃葡萄糖基单元和易于形成半缩酮环E的特点。七种糠醛甾醇皂苷的总合成包括fun素B使用容易获得的16β-乙酰氧基-22-氧代-26-羟基胆甾醇衍生物作为有效的构建基块可有效地获得，，，，，、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、还评估了合成皂苷的α-葡萄糖苷酶抑制活性，这表明fun药苷B是开发α-葡萄糖苷酶抑制剂的高度潜在的先导。

  DOI：

  10.1039/c6ob01766e

文献信息

• The substrate specificity of a glucoamylase with steroidal saponin-rhamnosidase activity from Curvularia lunata
  作者：Bing Feng、Li-ping Kang、Bai-ping Ma、Bo Quan、Wen-bin Zhou、Yong-ze Wang、Yu Zhao、Yi-xun Liu、Sheng-qi Wang

  DOI：10.1016/j.tet.2007.04.076

  日期：2007.7

  In previous work, we studied and reported that an enzyme from Curvularia lunata 3.4381 had the novel specificity to hydrolyze the terminal rhamnosyl at C-3 position of steroidal saponin and obtained four transformed products; the enzyme was purified and ascertained as glucoamylase (EC 3.2.1.3 GA). In this work, the enzyme exhibiting steroidal saponin-rhamnosidase activity was systematically studied on 21 steroidal saponins and 6 ginsenosides. The results showed that the alpha-1,2-linked end-rhamnosyl residues at C-3 position of steroidal saponins could be hydrolyzed to corresponding secondary steroidal saponins, among which 18 compounds were isolated and identified, including 3 new secondary compounds. For the furostanosides having glucosyl residues at the C-26 position, hydrolysis occurred first at end- rhamnosyl at C-3 position to produce secondary furostanosides. The reaction of hydrolyzing glucosyl at C-26 position depended considerably on longer reaction times yielding the corresponding secondary spirostanosides ( without rhamnosyl and glucosyl residues). The enzyme had the strict specificity for the terminal alpha-1,2-linked rhamnosyl residues of linear chain, or the terminal alpha-1,2-linked rhamnosyl residues with branched chain of 1,4-linked glycosyl residues of sugar chain at C-3 position of steroidal saponins, it was not specific for different aglycones, different glycons, and the number of glycon of sugar chain of steroidal saponin. The end- rhamnosyl of ginsenosides and p-nitrophenyl-a-L-rhamnopyranoside (pNPR) could not be hydrolyzed by the enzyme from C. lunata. (c) 2007 Elsevier Ltd. All rights reserved.
• Synthesis of furostanol glycosides: discovery of a potent α-glucosidase inhibitor
  作者：Peng Wang、Jiejie Hao、Xiuli Zhang、Cong Wang、Huashi Guan、Ming Li

  DOI：10.1039/c6ob01766e

  日期：——

  A convenient approach to the synthesis of furostanol glycosides has been developed with the features of both highly efficient incorporation of a 26-O-β-D-glucopyranosyl unit and ready formation of hemiketal ring E. The total syntheses of seven furostanol saponins including funlioside B, lilioglycoside, protobioside I, protodioscin, pallidifloside I, coreajaponins A and parisaponin I are efficiently

  已经开发了一种方便的合成糠醛甾醇糖苷的方法，该方法具有高效掺入26- O- β- D-吡喃葡萄糖基单元和易于形成半缩酮环E的特点。七种糠醛甾醇皂苷的总合成包括fun素B使用容易获得的16β-乙酰氧基-22-氧代-26-羟基胆甾醇衍生物作为有效的构建基块可有效地获得，，，，，、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、、还评估了合成皂苷的α-葡萄糖苷酶抑制活性，这表明fun药苷B是开发α-葡萄糖苷酶抑制剂的高度潜在的先导。
• Selective glycosylation of steroidal saponins by Arthrobacter nitroguajacolicus
  作者：Jing-yuan Liu、Li Lu、Li-ping Kang、Yi-xun Liu、Yang Zhao、Cheng-qi Xiong、Yu-qin Zhang、Li-yan Yu、Bai-ping Ma

  DOI：10.1016/j.carres.2014.07.006

  日期：2015.1

  In this study seven strains of the genus Arthrobacter were screened by biotransformation to discover glycosylating patterns on steroid saponins. A strain of Arthrobacter nitroguajacolicus (CPCC 203516) was found to have the ability of fructosylation. Crude enzyme of the strain was extracted for the further study of conversion characteristics and patterns. Sucrose was used as a non-activated sugar donor, and fifteen steroidal saponins were involved. Nine furostan saponins of the substrates were converted, and ten products were isolated and identified. Based on the HR-ESI-MS, 1D, and 2D NMR spectral data, one fructosyl was added to furostan saponins at C-6-OH of 26-O-beta-D-glucopyranosyl by A. nitroguajacolicus for all nine products. One product was distinguished by an additional fructosyl at the position of C-6-OH on the first added fructosyl. Spirostan saponins of the substrates could not be converted. Steroidal saponins embracing a fructosyl are quite rare according to other reports based on similar studies. This study successfully converted furostan saponins into new compounds. (C) 2014 Elsevier Ltd. All rights reserved.