三七皂苷R2(S型) | 80418-25-3

• 物质功能分类: 生物化工 - 提取物 - 植物提取物
• 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
• 中文名称: 三七皂苷R2(S型)
• 中文别名: 三七皂苷R2
• 英文名称: notoginsenoside R2
• 英文别名: 20(S)-notoginsenoside R2；(2S,3R,4S,5R)-2-[(2R,3R,4S,5S,6R)-2-[[(3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-17-[(2S)-2-hydroxy-6-methylhept-5-en-2-yl]-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-6-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-3-yl]oxyoxane-3,4,5-triol
• CAS: 80418-25-3
• 化学式: C₄₁H₇₀O₁₃
• 分子量: 770.999
• InChiKey: FNIRVWPHRMMRQI-PGOMJGFXSA-N

物化性质

• 密度：
  1.31±0.1 g/cm3 (20 ºC 760 Torr)
• 溶解度：
  溶于甲醇；

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  54
• 可旋转键数：
  9
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  219
• 氢给体数：
  9
• 氢受体数：
  13

安全信息

• WGK Germany：
  3

制备方法与用途

生物活性方面，三七皂苷R2（Notoginsenoside R2）是一种新分离的三七皂苷，显示出对6-OHDA诱导的氧化应激和细胞凋亡有保护作用。这种活性成分即(20S)-三七皂苷R2是从三七中提取出来的，并具有显著的神经保护效果。

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  三七皂甙 R1	notoginsenoside R1	80418-24-2	C47H80O18	933.141

• 下游产品

  中文名称	英文名称	CAS号	化学式	分子量
  人参皂苷Rh1	ginsenoside Rh1	63223-86-9	C36H62O9	638.883

反应信息

• 作为反应物：
  描述：

  三七皂苷R2(S型) 在 Sphingomonas sp. JB13 GH39 β-xylosidase 、 水 作用下， 反应 24.0h， 生成 人参皂苷Rh1
  参考文献：
  名称：

  Glycoside Hydrolase Family 39 β-Xylosidases Exhibit β-1,2-Xylosidase Activity for Transformation of Notoginsenosides: A New EC Subsubclass

  摘要：

  beta-1,2-Xylosidase activity has not been recorded as an EC subsubclass. In this study, phylogenetic analysis and multiple sequence alignments revealed that characterized beta-xylosidases of glycoside hydrolase family (GH) 39 were classified into the same subgroup with conserved amino acid residue positions participating in substrate recognition. Protein-ligand docking revealed that seven of these positions were probably essential to bind xylose-glucose, which is linked by a beta-1,2-glycosidic bond. Amino acid residues in five of the seven positions are invariant, while those in two of the seven positions are variable with low frequency. Both the wild-type beta-xylosidase rJB13GH39 and its mutants with mutation at the two positions exhibited beta-1,2-xylosidase activity, as they hydrolyzed o-nitrophenyl-beta-D-xylopyranoside and transformed notoginsenosides R-1 and R-2 to ginsenosides Rg(1) and Rh-1, respectively. The results suggest that all of these characterized GH 39 beta-xylosidases probably show beta-1,2-xylosidase activity, which should be assigned an EC number with these beta-xylosidases as representatives.

  DOI：

  10.1021/acs.jafc.9b00027
• 作为产物：
  描述：

  三七皂甙 R1 在 溶剂黄146 作用下， 以 水 为溶剂， 反应 5.0h， 生成 20(R)-notoginsenoside R2 、 三七皂苷R2(S型)
  参考文献：
  名称：

  Dammarane-saponins of sanchi-ginseng, roots of Panax notoginseng (Burk.) F.H. Chen (araliaceae): Structures of new saponins, notoginsenosides-R1 and -R2, and identification of ginsenosides-Rg2 and -Rh1.

  摘要：

  通过反相高效液相色谱法，从中国云南栽培的三七根中分离出两种新的达玛烷皂苷，分别命名为三七皂苷-R1（5）和-R2（7S）。通过反相高效液相色谱法，确定了这两种皂苷的结构为 20 (S)-protopanaxatriol 6-[O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranoside (5) 和 20 (S)-protopanaxatriol 6-O-β-D-xylopyranosyl (1→2)-β-D-glucopyranoside (7S)、主要通过 13C NMR 光谱法和质谱法分别对其进行了分析。除这些皂苷外，还分离鉴定了两种已知的皂苷，人参皂苷-Rh1（12）和-Rg2（13），这两种皂苷之前已从人参根中分离出来。

  DOI：

  10.1248/cpb.29.2844

文献信息

• Glycoside Hydrolase Family 39 β-Xylosidases Exhibit β-1,2-Xylosidase Activity for Transformation of Notoginsenosides: A New EC Subsubclass
  作者：Rui Zhang、Na Li、Shujing Xu、Xiaowei Han、Chunyan Li、Xin Wei、Yu Liu、Tao Tu、Xianghua Tang、Junpei Zhou、Zunxi Huang

  DOI：10.1021/acs.jafc.9b00027

  日期：2019.3.20

  beta-1,2-Xylosidase activity has not been recorded as an EC subsubclass. In this study, phylogenetic analysis and multiple sequence alignments revealed that characterized beta-xylosidases of glycoside hydrolase family (GH) 39 were classified into the same subgroup with conserved amino acid residue positions participating in substrate recognition. Protein-ligand docking revealed that seven of these positions were probably essential to bind xylose-glucose, which is linked by a beta-1,2-glycosidic bond. Amino acid residues in five of the seven positions are invariant, while those in two of the seven positions are variable with low frequency. Both the wild-type beta-xylosidase rJB13GH39 and its mutants with mutation at the two positions exhibited beta-1,2-xylosidase activity, as they hydrolyzed o-nitrophenyl-beta-D-xylopyranoside and transformed notoginsenosides R-1 and R-2 to ginsenosides Rg(1) and Rh-1, respectively. The results suggest that all of these characterized GH 39 beta-xylosidases probably show beta-1,2-xylosidase activity, which should be assigned an EC number with these beta-xylosidases as representatives.
• Dammarane-saponins of sanchi-ginseng, roots of Panax notoginseng (Burk.) F.H. Chen (araliaceae): Structures of new saponins, notoginsenosides-R1 and -R2, and identification of ginsenosides-Rg2 and -Rh1.
  作者：JUN ZHOU、MINGZHU WU、SHIGENORI TANIYASU、HIROMICHI BESSO、OSAMU TANAKA、YUICHIRO SARUWATARI、TOHRU FUWA

  DOI：10.1248/cpb.29.2844

  日期：——

  From Sanchi-Ginseng, roots of Panax notoginseng cultivated in Yunnan, China, two new dammarane-saponins named notoginsenosides-R1 (5) and -R2 (7S) were isolated by means of reverse phase high performance liquid chromatography. The structures of these saponins were established as 20 (S)-protopanaxatriol 6-[O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranoside (5) and 20 (S)-protopanaxatriol 6-O-β-D-xylopyranosyl (1→2)-β-D-glucopyranoside (7S), respectively, mainly by 13C NMR spectroscopy and mass spectrometry. In connection with this study, assignments of carbon signals of ginsenoside-Rf (11), a minor saponin of Ginseng roots, were substantiated by the application of selective deuteration of the sugar moiety as reported by Stuart et al. Besides these saponins, two known saponins, ginsenosides-Rh1 (12) and -Rg2 (13) which have previously been isolated from Ginseng roots, were also isolated and identified.

  通过反相高效液相色谱法，从中国云南栽培的三七根中分离出两种新的达玛烷皂苷，分别命名为三七皂苷-R1（5）和-R2（7S）。通过反相高效液相色谱法，确定了这两种皂苷的结构为 20 (S)-protopanaxatriol 6-[O-β-D-xylopyranosyl-(1→2)-β-D-glucopyranosyl]-20-O-β-D-glucopyranoside (5) 和 20 (S)-protopanaxatriol 6-O-β-D-xylopyranosyl (1→2)-β-D-glucopyranoside (7S)、主要通过 13C NMR 光谱法和质谱法分别对其进行了分析。除这些皂苷外，还分离鉴定了两种已知的皂苷，人参皂苷-Rh1（12）和-Rg2（13），这两种皂苷之前已从人参根中分离出来。