goodyeroside A | 211107-44-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: goodyeroside A
• 英文别名: (3S)-3-(β-D-glucopyranosyloxy)butanolide；goodyeroside；(4S)-4-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyoxolan-2-one
• CAS: 211107-44-7
• 化学式: C₁₀H₁₆O₈
• 分子量: 264.232
• InChiKey: MQEPWBMWFIVRPS-MBOSOLAWSA-N

物化性质

• 熔点：
  154-155 °C
• 沸点：
  570.2±50.0 °C(Predicted)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  苯甲酰氯 、 goodyeroside A 在 吡啶 作用下， 反应 17.0h， 以90%的产率得到3-O-(2,3,4,6-tetra-O-benzoyl-β-D-glucopyranosyl)-(3S)-3-hydroxy-γ-butyrolactone
  参考文献：
  名称：

  Synthesis of 3‐O‐β‐D‐Glucopyranosyl‐(3R)‐hydroxybutanolide (Kinsenoside) and 3‐O‐β‐D‐Glucopyranosyl‐(3S)‐hydroxybutanolide (Goodyeroside A)

  摘要：

  The first synthesis of 3-O-beta-D-glucopyranosyl-(3R)-hydroxybutanolide (Kinsenoside) and 3-O-beta-D-glucopyranosyl-(3S)-hydroxybutanolide (Goodyeroside A) is described. The diastereomers of the aglycon in 2-O-beta-D-gulucopyranosyl-1,2,4-butanetriol derivatives, which were separable precursors of Kinsenoside and Goodyeroside A, were synthesized from optically nonactive 1,2,4-butanetriol and alpha-D-glucopyranosyl trichloroacetimidate in excellent yields.

  DOI：

  10.1081/car-200050541
• 作为产物：
  描述：

  4-甲氧基苯基Β-D-吡喃葡萄糖苷 在 ammonium cerium (IV) nitrate 、 三氟甲磺酸三甲基硅酯 、 palladium 10% on activated carbon 、 水 、 氢气 、 sodium hydride 、 溶剂黄146 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 乙醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 、 mineral oil 为溶剂， 反应 18.25h， 生成 goodyeroside A
  参考文献：
  名称：

  具有抗炎活性的天然产物人参皂苷类似物的合成

  摘要：

  人参皂苷是来自草药的主要生物活性成分，具有广泛的药理功能。Goodyeroside A 是kinsenoside 的一种差向异构体，仍然很少被探索。在本报告中，我们化学合成了人参皂苷、Goodyeroside A 及其类似物，具有聚糖变异、手性中心的手性反转以及内酰胺对内酯的生物等排置换。在这些化合物中，goodyeroside A 及其甘露糖基对应物表现出优异的抗炎功效。此外，还发现枸杞苷 A 通过抑制 NF-κB 信号通路有效抑制炎症。还探索了构效关系，以进一步开发更有前途的人参皂苷类似物作为候选药物。

  DOI：

  10.1016/j.bmc.2020.115854

文献信息

• Design, Synthesis and Hepatoprotective Activity of Analogs of the Natural Product Goodyeroside A
  作者：Feng Zhang、Bei Han、Peng Li、Ziyun Lin、Dali Yin、Yan Li、Jialiang Zhong、Haihong Huang

  DOI：10.3390/molecules18021933

  日期：——

  Goodyeroside A, a natural product isolated from the Goodyera species, possesses significant hepatoprotective activity and has a novel skeleton not previously observed in other synthetic drugs used for the treatment of hepatitis. Herein, we report a highly stereoselective synthesis of goodyeroside A and related analogs with varying substituents at the α position of the carbonyl group to explore the structure-activity relationships of goodyeroside A. The absolute configuration of analog 5d was confirmed by single crystal X-ray analysis. The results from in vitro and in vivo studies indicate that 5a, the fully acetylated compound of goodyeroside A, is worthy of further investigation as a lead to identify novel hepatoprotective agents.

  Goodyeroside A 是一种从 Goodyera 物种中分离出来的天然产物，具有显著的保肝活性，其新颖的骨架是以前在其他用于治疗肝炎的合成药物中未观察到的。在此，我们报告了一种高度立体选择性的合成方法，即在羰基的 α 位上用不同的取代基合成 goodyeroside A 及相关类似物，以探索 goodyeroside A 的结构-活性关系。体外和体内研究的结果表明，5a 是一种完全乙酰化的好耶罗苷 A 化合物，值得进一步研究，以寻找新型保肝药物。
• Efficient Synthesis of Kinsenoside and Goodyeroside A by a Chemo-Enzymatic Approach
  作者：Yang Zhang、Yihong Xia、Yongji Lai、Fang Tang、Zengwei Luo、Yongbo Xue、Guangmin Yao、Yonghui Zhang、Jinwen Zhang

  DOI：10.3390/molecules191016950

  日期：——

  efficiently by a chemo-enzymatic approach with a total yield of 12.7%. The aglycones, (R)- and (S)-3-hydroxy-γ-butyrolactone, were prepared from D- and L-malic acid by a four-step chemical approach with a yield of 75%, respectively. These butyrolactones were then successfully glycosidated using β-D-glucosidase as a catalyst in a homogeneous organic-water system. Under the optimized enzymatic conditions, the yields

  Kinsenoside (1) 和 goodyeroside A (2) 是两种具有多种生物活性的天然立体异构体，已通过化学酶促方法有效合成，总产率为 12.7%。苷元，(R)-和(S)-3-羟基-γ-丁内酯，分别由D-和L-苹果酸通过四步化学方法制备，产率分别为75%。然后在均相有机水系统中使用 β-D-葡萄糖苷酶作为催化剂成功地糖苷化这些丁内酯。在优化后的酶促条件下，酶促步骤中kinsenoside和goodyeroside A的产率均达到16.8%。
• Hepatoprotective Aliphatic Glycosides from Three Goodyera Species.
  作者：Xiao-Ming DU、Ning-Yi SUN、Yang CHEN、Nobuto IRINO、Yukihiro SHOYAMA

  DOI：10.1248/bpb.23.731

  日期：——

  Hepatoprotective aliphatic glycosides 3-(S)-3-β-D-glucopyranosyloxybutanolide (1) and its congener, 3-(S)-3-β-D-glucopyranosyloxy-4-hydroxybutanoic acid (2) were isolated as major constituents from the whole plants of three Goodyera species, G. schlechtendaliana REICHB. fil., G. matsumurana SCHLTR. and G. discolor KER-GAWL. The structures of 1 and 2 have been determined by NMR, MS spectroscopic and chemical means. Compound 1 was converted into its methyl ester form (5) during the purification step, when the lactone ring was cleaved by catalysis of silica gel with the CHCl3-MeOH-H2O as a solvent. On the other hand, 1 was obtained in a high yield by the same purification procedure without MeOH. Based on this fact, a simple and economic method for the purification of 1 was confirmed. Compounds 1 and 2 were found to have a hepatoprotective effect on liver injury induced by carbon tetrachloride in primary cultured rat hepatocytes.

  保肝脂肪族糖苷 3-(S)-3-β-D-吡喃葡萄糖氧基丁内酯 (1) 及其同源物 3-(S)-3-β-D-吡喃葡萄糖氧基-4-羟基丁酸 (2) 作为主要成分从三个 Goodyera 物种 G. schlechtendaliana REICHB 的全株。 fil.，G. matsumurana SCHLTR。 G. KER-GAWL 变色。 1和2的结构已通过NMR、MS光谱和化学手段确定。在纯化步骤中，以CHCl3-MeOH-H2O为溶剂，通过硅胶催化，内酯环裂解，化合物1转化为其甲酯形式(5)。另一方面，在没有MeOH的情况下通过相同的纯化程序以高产率获得1。基于这一事实，确定了一种简单且经济的纯化1的方法。发现化合物1和2对原代培养的大鼠肝细胞由四氯化碳引起的肝损伤具有保肝作用。
• Synthesis of 3‐<i>O</i>‐β‐<scp>D</scp>‐Glucopyranosyl‐(3<i>R</i>)‐hydroxybutanolide (Kinsenoside) and 3‐<i>O</i>‐β‐<scp>D</scp>‐Glucopyranosyl‐(3<i>S</i>)‐hydroxybutanolide (Goodyeroside A)
  作者：Katsuhiko Suzuki、Nobuyuki Suzuki、Masanori Yamaura、Toyokichi Yoshizawa

  DOI：10.1081/car-200050541

  日期：2005.1

  The first synthesis of 3-O-beta-D-glucopyranosyl-(3R)-hydroxybutanolide (Kinsenoside) and 3-O-beta-D-glucopyranosyl-(3S)-hydroxybutanolide (Goodyeroside A) is described. The diastereomers of the aglycon in 2-O-beta-D-gulucopyranosyl-1,2,4-butanetriol derivatives, which were separable precursors of Kinsenoside and Goodyeroside A, were synthesized from optically nonactive 1,2,4-butanetriol and alpha-D-glucopyranosyl trichloroacetimidate in excellent yields.
• Synthesis of nature product kinsenoside analogues with anti-inflammatory activity
  作者：Wei Song、Yong Sun、Lintao Xu、Yajing Sun、Tianlu Li、Peng Peng、Hongxiang Lou

  DOI：10.1016/j.bmc.2020.115854

  日期：2021.1

  medicine with a broad range of pharmacological functions. Goodyeroside A, an epimer of kinsenoside, remains less explored. In this report we chemically synthesized kinsenoside, goodyeroside A and their analogues with glycan variation, chirality inversion at chiral center(s), and bioisosteric replacement of lactone with lactam. Among these compounds, goodyeroside A and its mannosyl counterpart demonstrated

  人参皂苷是来自草药的主要生物活性成分，具有广泛的药理功能。Goodyeroside A 是kinsenoside 的一种差向异构体，仍然很少被探索。在本报告中，我们化学合成了人参皂苷、Goodyeroside A 及其类似物，具有聚糖变异、手性中心的手性反转以及内酰胺对内酯的生物等排置换。在这些化合物中，goodyeroside A 及其甘露糖基对应物表现出优异的抗炎功效。此外，还发现枸杞苷 A 通过抑制 NF-κB 信号通路有效抑制炎症。还探索了构效关系，以进一步开发更有前途的人参皂苷类似物作为候选药物。