ginsenoside-Ra₁

• 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: ginsenoside-Ra₁
• 英文别名: (2S,3R,4S,5S,6R)-2-[(2S,3R,4S,5S,6R)-3-[[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-17-[(2S)-2-[(2S,3R,4S,5S,6R)-6-[[(2S,3R,4R,5S)-3,4-dihydroxy-5-[(2S,3R,4S,5R)-3,4,5-trihydroxyoxan-2-yl]oxyoxan-2-yl]oxymethyl]-3,4,5-trihydroxyoxan-2-yl]oxy-6-methylhept-5-en-2-yl]-12-hydroxy-4,4,8,10,14-pentamethyl-2,3,5,6,7,9,11,12,13,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl]oxy]-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-6-(hydroxymethyl)oxane-3,4,5-triol
• 化学式: C₅₈H₉₈O₂₆
• 分子量: 1211.4
• InChiKey: YLOTVUIQEWTDME-WWJNHZDPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  84
• 可旋转键数：
  17
• 环数：
  9.0
• sp3杂化的碳原子比例：
  0.97
• 拓扑面积：
  416
• 氢给体数：
  16
• 氢受体数：
  26

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 ginsenoside-Ra₁ 以 吡啶 为溶剂， 反应 3.0h， 以9 mg的产率得到
  参考文献：
  名称：

  Studies on the saponins of ginseng. IV. On the structure and enzymatic hydrolysis of ginsenoside-Ra1.

  摘要：

  通过薄层色谱法已证实人参中存在人参皂苷-Ra。近期研究表明,人参皂苷-Ra是两种以上皂苷的混合物。其中,人参皂苷-Ra1被分离出来,并通过光谱、化学和酶解水解证据确定其结构为20(S)-原人参二醇3-O-β-D-葡萄糖基(1→2)-β-D-葡萄糖苷-20-O-β-D-木糖基(1→4)-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(1)。 除了化合物K(8)外,在人参皂苷-Ra1的酶解水解过程中还得到了三个原皂苷: - 20(S)-原人参二醇3-O-β-D-葡萄糖苷-20-O-β-D-葡萄糖苷(7) - 20(S)-原人参二醇3-O-β-D-葡萄糖苷-20-O-β-D-木糖基(1→4)-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(9) - 20(S)-原人参二醇20-O-β-D-木糖基(1→4)-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(10) 此外,通过人参皂苷-Rb2(4)的酶解水解获得了: - 20(S)-原人参二醇3-O-β-D-葡萄糖苷-20-O-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(6) - 化合物7和8 文中还讨论了人参皂苷与柚皮苷酶的酶解水解过程。

  DOI：

  10.1248/cpb.30.2393

文献信息

• Studies on the saponins of ginseng. IV. On the structure and enzymatic hydrolysis of ginsenoside-Ra1.
  作者：HARUYO KOIZUMI、SHUICHI SANADA、YOSHITERU IDA、JUNZO SHOJI

  DOI：10.1248/cpb.30.2393

  日期：——

  The presence of ginsenoside-Ra in Ginseng Radix has been demonstrated by thin-layer chromatography. Recently, ginsenoside-Ra was shown to be a mixture of more than two saponins. Among them, ginsenoside-Ra1 was isolated and its structure was determined on the basis of spectral, chemical and enzymatic hydrolysis evidence as 20 (S)-protopanaxadiol 3-O-β-D-glucopyranosyl (1→2)-β-D-glucopyranosido-20-O-β-D-xylopyranosyl (1→4)-α-L-arabinopyranosyl (1→6)-β-D-glucopyranoside (1). Besides compound K (8), three prosapogenins, 20 (S)-protopanaxadiol 3-O-β-D-glucopyranosido-20-O-β-D-glucopyranoside (7), 20 (S)-protopanaxadiol 3-O-β-D-glucopyranosido-20-O-β-D-xylopyranosyl (1→4)-α-L-arabinopyranosyl (1→6)-β-D-glucopyranoside (9), and 20 (S)-protopanaxadiol 20-O-β-D-xylopyranosyl (1→4)-α-L-arabinopyranosyl (1→6)-β-D-glucopyranoside (10) were obtained in the course of enzymatic hydrolysis of ginsenoside-Ra1. Further, 20 (S)-protopanaxadiol 3-O-β-D-glucopyranosido-20-O-α-L-arabinopyranosyl (1→6)-β-D-glucopyranoside (6), 7 and 8 were obtained by enzymatic hydrolysis of ginsenoside-Rb2 (4). The course of enzymatic hydrolysis of ginsenosides with naringinase is also discussed.

  通过薄层色谱法已证实人参中存在人参皂苷-Ra。近期研究表明,人参皂苷-Ra是两种以上皂苷的混合物。其中,人参皂苷-Ra1被分离出来,并通过光谱、化学和酶解水解证据确定其结构为20(S)-原人参二醇3-O-β-D-葡萄糖基(1→2)-β-D-葡萄糖苷-20-O-β-D-木糖基(1→4)-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(1)。 除了化合物K(8)外,在人参皂苷-Ra1的酶解水解过程中还得到了三个原皂苷: - 20(S)-原人参二醇3-O-β-D-葡萄糖苷-20-O-β-D-葡萄糖苷(7) - 20(S)-原人参二醇3-O-β-D-葡萄糖苷-20-O-β-D-木糖基(1→4)-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(9) - 20(S)-原人参二醇20-O-β-D-木糖基(1→4)-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(10) 此外,通过人参皂苷-Rb2(4)的酶解水解获得了: - 20(S)-原人参二醇3-O-β-D-葡萄糖苷-20-O-α-L-阿拉伯糖基(1→6)-β-D-葡萄糖苷(6) - 化合物7和8 文中还讨论了人参皂苷与柚皮苷酶的酶解水解过程。