人参皂苷CY | 83480-65-3

• 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: 人参皂苷CY
• 英文名称: compound Y
• 英文别名: ginsenoside C-Y；(2S,3R,4S,5S,6R)-2-[(2S)-2-[(3S,5R,8R,9R,10R,12R,13R,14R,17S)-3,12-dihydroxy-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]oxy-6-[[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxymethyl]oxane-3,4,5-triol
• CAS: 83480-65-3
• 化学式: C₄₁H₇₀O₁₂
• 分子量: 755.0
• InChiKey: YNBYFOIDLBTOMW-QHNUHGIDSA-N

物化性质

• 沸点：
  845.9±65.0 °C(Predicted)
• 密度：
  1.28±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  53
• 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：
  199
• 氢给体数：
  8
• 氢受体数：
  12

制备方法与用途

人参皂苷CY源自于红参的微生物转化过程，展现出强大的抗肿瘤生物活性。

反应信息

• 作为反应物：
  描述：

  乙酸酐 、 人参皂苷CY 以 吡啶 为溶剂， 反应 3.0h， 以30 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
• 作为产物：
  描述：

  人参皂苷Rb2 、 水 生成 人参皂苷CY 、 D-葡萄糖
  参考文献：
  名称：

  一种新型人参异形杆菌属的鉴定和表征。十一月 β-葡萄糖苷酶，可将人参皂苷 Rb1 转化为稀有的绞股蓝皂苷 XVII 和 LXXV。

  摘要：

  一种新的 β-葡糖苷酶来自从人参农场的土壤中获得的新菌株人参皂苷 (Gsoil 3082(T))，并将基因 bgpA (1,947 bp) 克隆到大肠杆菌中。该酶催化人参皂苷 Rb1 {3-O-[β-D-吡喃葡萄糖基-(1-2)-β-D-吡喃葡萄糖基]-20-O-[β-D-吡喃葡萄糖基-(1-6)-的转化β-D-吡喃葡萄糖基]-20(S)-原人参二醇}到更具药理活性的稀有人参皂苷 gypenoside XVII {3-O-β-D-吡喃葡萄糖基-20-O-[β-D-吡喃葡萄糖基-(1-6) -β-D-吡喃葡萄糖基]-20(S)-原人参二醇}，绞股蓝皂苷 LXXV {20-O-[β-v-吡喃葡萄糖基-(1-6)-β-D-吡喃葡萄糖基]-20(S)-原人参二醇}和 CK [20-O-(β-D-吡喃葡萄糖基)-20(S)-原人参二醇]。bgpA 序列的 BLAST 搜索揭示了与家族 3 糖苷水解酶

  DOI：

  10.1128/aem.00106-10

文献信息

• Enzymatic Biotransformation of Ginsenoside Rb1 and Gypenoside XVII into Ginsenosides Rd and F2 by Recombinant β-glucosidase from Flavobacterium johnsoniae
  作者：Hao Hong、Chang-Hao Cui、Jin-Kwang Kim、Feng-Xie Jin、Sun-Chang Kim、Wan-Taek Im

  DOI：10.5142/jgr.2012.36.4.418

  日期：2012.10.15

  This study focused on the enzymatic biotransformation of the major ginsenoside Rb1 into Rd for the mass production of minor ginsenosides using a novel recombinant $\beta}$-glucosidase from Flavobacterium johnsoniae. The gene (bglF3) consisting of 2,235 bp (744 amino acid residues) was cloned and the recombinant enzyme overexpressed in Escherichia coli BL21(DE3) was characterized. This enzyme could transform ginsenoside Rb1 and gypenoside XVII to the ginsenosides Rd and F2, respectively. The glutathione S-transferase (GST) fused BglF3 was purified with GST-bind agarose resin and characterized. The kinetic parameters for $\beta}$-glucosidase had apparent $K_m$ values of $0.91\pm}0.02$ and $2.84\pm}0.05$ mM and $V_max}$ values of $5.75\pm}0.12$ and $0.71\pm}0.01\mu}mol\cdot}min^-1}\cdot}mg$ of $protein^-1}$ against p-nitrophenyl-$\beta}$-D-glucopyranoside and Rb1, respectively. At optimal conditions of pH 6.0 and $37^\circ}C$, BglF3 could only hydrolyze the outer glucose moiety of ginsenoside Rb1 and gypenoside XVII at the C-20 position of aglycon into ginsenosides Rd and F2, respectively. These results indicate that the recombinant BglF3 could be useful for the mass production of ginsenosides Rd and F2 in the pharmaceutical or cosmetic industry.

  本研究的重点是利用从约翰逊黄杆菌（Flavobacterium johnsoniae）中提取的新型重组$\beta}$-葡萄糖苷酶，将主要人参皂苷Rb1酶促生物转化为Rd，从而大规模生产次要人参皂苷。克隆了由 2,235 bp（744 个氨基酸残基）组成的基因（bglF3），并对在大肠杆菌 BL21（DE3）中过表达的重组酶进行了鉴定。该酶可将人参皂苷 Rb1 和人参皂苷 XVII 分别转化为人参皂苷 Rd 和人参皂苷 F2。用 GST 结合琼脂糖树脂纯化了融合谷胱甘肽 S 转移酶（GST）的 BglF3，并对其进行了鉴定。$\beta}$-葡萄糖苷酶的动力学参数的表观$K_m$值为$0.91\pm}0.02和$2.84\pm}0.05 mM，$V_max}$值为$5.75\pm}0.12$ 和 $0.71\pm}0.01\mu}mol\cdot}min^-1}\cdot}mg$ 的 $protein^-1}$ 分别对对硝基苯-$\beta}$-D-吡喃葡萄糖苷和 Rb1 起作用。在pH 6.0和$37^\circ}C$的最佳条件下，BglF3只能将人参皂苷Rb1的外层葡萄糖分子和苷元C-20位上的天麻皂苷XVII分别水解为人参皂苷Rd和F2。这些结果表明，重组 BglF3 可用于制药或化妆品行业人参皂甙 Rd 和 F2 的大规模生产。
• Kinetics of a Cloned Special Ginsenosidase Hydrolyzing 3-O-Glucoside of Multi-Protopanaxadiol-Type Ginsenosides, Named Ginsenosidase Type III
  作者：Xue-Feng Jin

  DOI：10.4014/jmb.1107.07066

  日期：2012.3.28

  In this paper, the kinetics of a cloned special glucosidase, named ginsenosidase type III hydrolyzing 3-O-glucoside of multi-protopanaxadiol (PPD)-type ginsenosides, were investigated. The gene (hgpA) encoding this enzyme was cloned from a Terrabacter ginsenosidimutans strain and then expressed in E. coli cells. Ginsenosidase type III was able to hydrolyze 3-O-glucoside of multi-PPD-type ginsenosides. For instance, it was able to hydrolyze the 3-O-beta-D-(1 -> 2)-glucopyranosyl of Rb1 to gypenoside XVII, and then to further hydrolyze the 3-O-beta-D-glucopyranosyl of gypenoside XVII to gypenoside LXXV. Similarly, the enzyme could hydrolyze the glucopyranosyls linked to the 3-O-position of Rb2, Rc, Rd, Rb3, and Rg3. With a larger enzyme reaction K. value, there was a slower enzyme reaction speed; and the larger the enzyme reaction V-max value, the faster the enzyme reaction speed was. The K-m values from small to large were 3.85 mM for Rc, 4.08 mM for Rb1, 8.85 mM for Rb3, 9.09 mM for Rb2, 9.70 mM for Rg3(S), 11.4 mM for Rd and 12.9 mM for F2; and V-max value from large to small was 23.2 mM/h for Rc, 16.6 mM/h for Rb1, 14.6 mM/h for Rb3, 14.3 mM/h for Rb2, 1.81 mM/h for Rg3(S), 1.40 mM/h for Rd, and 0.41 mM/h for F2. According to the V-max and K-m values of the ginsenosidase type III, the hydrolysis speed of these substrates by the enzyme was Rc>Rb1>Rb3>Rb2>Rg3(S)>Rd>F2 in order.
• 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。
• Identification and Characterization of a Novel<i>Terrabacter ginsenosidimutans</i>sp. nov. β-Glucosidase That Transforms Ginsenoside Rb1 into the Rare Gypenosides XVII and LXXV
  作者：Dong-Shan An、Chang-Hao Cui、Hyung-Gwan Lee、Liang Wang、Sun Chang Kim、Sung-Taik Lee、Fengxie Jin、Hongshan Yu、Young-Won Chin、Hyeong-Kyu Lee、Wan-Taek Im、Song-Gun Kim

  DOI：10.1128/aem.00106-10

  日期：2010.9

  hydrolysis of the two glucose moieties attached to the C-3 position of ginsenoside Rb1, and the outer glucose attached to the C-20 position at pH 7.0 and 37 degrees C. These cleavages occurred in a defined order, with the outer glucose of C-3 cleaved first, followed by the inner glucose of C-3, and finally the outer glucose of C-20. These results indicated that BgpA selectively and sequentially converts ginsenoside

  一种新的 β-葡糖苷酶来自从人参农场的土壤中获得的新菌株人参皂苷 (Gsoil 3082(T))，并将基因 bgpA (1,947 bp) 克隆到大肠杆菌中。该酶催化人参皂苷 Rb1 3-O-[β-D-吡喃葡萄糖基-(1-2)-β-D-吡喃葡萄糖基]-20-O-[β-D-吡喃葡萄糖基-(1-6)-的转化β-D-吡喃葡萄糖基]-20(S)-原人参二醇}到更具药理活性的稀有人参皂苷 gypenoside XVII 3-O-β-D-吡喃葡萄糖基-20-O-[β-D-吡喃葡萄糖基-(1-6) -β-D-吡喃葡萄糖基]-20(S)-原人参二醇}，绞股蓝皂苷 LXXV 20-O-[β-v-吡喃葡萄糖基-(1-6)-β-D-吡喃葡萄糖基]-20(S)-原人参二醇}和 CK [20-O-(β-D-吡喃葡萄糖基)-20(S)-原人参二醇]。bgpA 序列的 BLAST 搜索揭示了与家族 3 糖苷水解酶