3-(R)-3-β-D-glucopyranosyloxy-4-hydroxybutanoic acid | 220235-66-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 3-(R)-3-β-D-glucopyranosyloxy-4-hydroxybutanoic acid
• 英文别名: (3r)-3-(beta-d-Glucopyranosyloxy)-4-hydroxybutanoic acid；(3R)-4-hydroxy-3-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybutanoic acid
• CAS: 220235-66-5
• 化学式: C₁₀H₁₈O₉
• 分子量: 282.248
• InChiKey: XBHPIDRJPMHODV-ZGSHZZHUSA-N

物化性质

• 沸点：
  636.4±55.0 °C(Predicted)
• 密度：
  1.62±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  157
• 氢给体数：
  6
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  3-(R)-3-β-D-glucopyranosyloxy-4-hydroxybutanoic acid 在 硫酸 作用下， 以 水 为溶剂， 反应 2.0h， 以11 mg的产率得到金线莲苷
  参考文献：
  名称：

  Butanoic acid glucoside composition of whole body and in vitro plantlets of Anoectochilus formosanus

  摘要：

  A butanoic acid glucoside, 3-O-beta-D-glucopyranosyl-(3R)-4-dihydroxy butanoic acid, with known aliphatic glucosides were isolated from the methanol extract of dried whole plants of Anoectochilus formosanus Hay. Butanoic acid glucosides were formed in 3 types of regenerated plantlets in vitro. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0031-9422(98)00388-4
• 作为产物：
  描述：

  金线莲苷 在 水 作用下， 生成 3-(R)-3-β-D-glucopyranosyloxy-4-hydroxybutanoic acid
  参考文献：
  名称：

  Higher Yielding Isolation of Kinsenoside in Anoectochilus and Its Antihyperliposis Effect.

  摘要：

  通过 HPLC 分析，在粗制药物 Anoectochilus formosanus 和 A. koshunensis 中检测到较高浓度的人参皂甙，即 3-(R)-3-β-D-吡喃葡萄糖氧基丁内酯（1）。在纯化步骤中使用含甲醇的溶剂进行硅胶催化裂解 1 的内酯环时，发生了甲基化反应，生成了甲酯（4），导致 1 难以纯化。在使用高脂饮食大鼠进行的抗脂肪肝试验中，与对照组相比，1 能显著降低大鼠的体重和肝脏重量，并降低肝脏中甘油三酯的含量。另一方面，从古德耶拉（Goodyera）物种中分离出的 1、3-(S)-3-β-D-吡喃葡萄糖基氧基丁内酯（2）的表单体（三者均命名为古德耶拉内酯 A）对抗血脂形成没有作用。在乌拉糖诱导的肥胖小鼠中，1 抑制了体重和肝脏重量的增加，显著改善了肝脏中甘油三酯的水平，还减少了子宫脂肪垫的沉积。

  DOI：

  10.1248/bpb.24.65

文献信息

• Butanoic acid glucoside composition of whole body and in vitro plantlets of Anoectochilus formosanus
  作者：Xiao-Ming Du、Toyokichi Yoshizawa、Yukihiro Shoyama

  DOI：10.1016/s0031-9422(98)00388-4

  日期：1998.12

  A butanoic acid glucoside, 3-O-beta-D-glucopyranosyl-(3R)-4-dihydroxy butanoic acid, with known aliphatic glucosides were isolated from the methanol extract of dried whole plants of Anoectochilus formosanus Hay. Butanoic acid glucosides were formed in 3 types of regenerated plantlets in vitro. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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.
• Higher Yielding Isolation of Kinsenoside in Anoectochilus and Its Antihyperliposis Effect.
  作者：Xiao-Ming DU、Ning-Yi SUN、Takashi TAMURA、Atsushi MOHRI、Minoru SUGIURA、Toyokichi YOSHIZAWA、Nobuto IRINO、Jun HAYASHI、Yukihiro SHOYAMA

  DOI：10.1248/bpb.24.65

  日期：——

  A higher concentration of kinsenoside, 3-(R)-3-β-D-glucopyranosyloxybutanolide (1), was detected in the crude drug Anoectochilus formosanus, and A. koshunensis by HPLC analysis. A methylation reaction occurred to give methyl ester (4) when the lactone ring of 1 was cleaved by silica gel catalysis using methanol containing solvent used in the purification step resulting in difficulty to purify 1. To avoid the cleavage reaction, a reversed-phase or silica gel column without methanol was used to give a high yield of 1. In an anti-hyperliposis assay using high-fat diet rats, 1 significantly reduced the weights of body and liver, and also decreased the triglyceride level in the liver compared to those of control rats. On the other hand, the epimer of 1, 3-(S)-3-β-D-glucopyranosyloxybutanolide (2), trivially named goodyeroside A, which was isolated from Goodyera species, had no effect for anti-hyperliposis. In aurothioglucose-induced obese mouse, 1 suppressed the body and liver weight increase, significantly ameliorated the triglyceride level in the liver, and also reduced the deposition of uterine fat-pads.

  通过 HPLC 分析，在粗制药物 Anoectochilus formosanus 和 A. koshunensis 中检测到较高浓度的人参皂甙，即 3-(R)-3-β-D-吡喃葡萄糖氧基丁内酯（1）。在纯化步骤中使用含甲醇的溶剂进行硅胶催化裂解 1 的内酯环时，发生了甲基化反应，生成了甲酯（4），导致 1 难以纯化。在使用高脂饮食大鼠进行的抗脂肪肝试验中，与对照组相比，1 能显著降低大鼠的体重和肝脏重量，并降低肝脏中甘油三酯的含量。另一方面，从古德耶拉（Goodyera）物种中分离出的 1、3-(S)-3-β-D-吡喃葡萄糖基氧基丁内酯（2）的表单体（三者均命名为古德耶拉内酯 A）对抗血脂形成没有作用。在乌拉糖诱导的肥胖小鼠中，1 抑制了体重和肝脏重量的增加，显著改善了肝脏中甘油三酯的水平，还减少了子宫脂肪垫的沉积。