| 138267-97-7

• 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
• CAS: 138267-97-7；138267-98-8；145781-63-1；145781-64-2
• 化学式: C₄₂H₆₄O₁₅
• 分子量: 808.961
• InChiKey: UESGIOZUTMALSQ-BXZQPDEUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.15
• 重原子数：
  57.0
• 可旋转键数：
  7.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  249.97
• 氢给体数：
  8.0
• 氢受体数：
  13.0

反应信息

• 作为产物：
  描述：

  benzyl 3,4-di-O-benzyl-α-D-glucuronatopyranose 1,2-O-(ethyl orthoacetate) 在 palladium on activated charcoal 吡啶 、 sodium hydroxide 、 三氟甲磺酸三甲基硅酯 、 4 A molecular sieve 、 氢气 、 sodium methylate 、 silver trifluoromethanesulfonate 、 溶剂黄146 、 1,1,3,3-四甲基脲 作用下， 以 二氯甲烷 为溶剂， 反应 74.25h， 生成
  参考文献：
  名称：

  Preparation of Glycyrrhetic Acid Glycosides Having Various .BETA.(1.RAR.2)-Linked Disaccharides and Their Cytoprotective Effects on Carbon Tetrachloride-Induced Hepatic Injury.

  摘要：

  通过逐步构建法分别合成了 2-O-β-D-吡喃葡萄糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃半乳糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃半乳糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃葡萄糖基-β-D-吡喃葡萄糖、2-O-β-D-吡喃葡萄糖基-β-D-吡喃葡萄糖；从葡萄糖醛酸单糖苷到二糖苷。将苷 1-7 和 2-O-(β-D-吡喃葡萄糖基)-β-D-吡喃葡萄糖基-11-氧代甘草甜素-12-烯-30-酸酯（8）的细胞保护活性与天然存在的甘草甜素（9）进行了比较。在这些苷 1-8 中，苷 3 和苷 7 以 β-D-吡喃葡萄糖（glcUA）为唯一的末端糖成分，是比甘草苷 9 更有效的抗肝损伤材料。

  DOI：

  10.1248/cpb.39.2333

文献信息

• Preparation of Glycyrrhetic Acid .BETA.-Glycosides Having .BETA.(1.RAR.2)-Linked Disaccharides by the Use of 2-O-Trichloroacetyl-.BETA.-D-pyranosyl Chlorides and Their Cytoprotective Effects on Hepatic Injury in Vivo.
  作者：Setsuo SAITO、Yuka SASAKI、Kaoru KURODA、Yasunobu HAYASHI、Shigeya SUMITA、Yoichi NAGAMURA、Keiji NISHIDA、Isao ISHIGURO

  DOI：10.1248/cpb.41.539

  日期：——

  Stepwise glycosidation was adopted for the construction of glycyrrhetic acid β-glycosides (27-30) having β(1→2)-linked disaccharides such as 2-O-β-D-flucuronopyranosyl-β-D-glucopyranose, 2-O-β-D-glucuronopyranosyl-β-D-galactopyranose, 2-O-β-D-glucopyranosyl-β-D-glucuronopyranose and 2-O-β-D-galactopyranosyl-β-D-glucuronopyranose. In the first glycosidation, 2-O-trichloroacety-β-D-pyranosyl chlorides (9-11) were utilized as starting sugar derivatives to react with methyl glycyrrhetinate (5) : Glycosidation of 5 with 9 and 10 gave β- and α-monoglycosides (12) and (13), and (15) and (16), respectively. Treatment of the β-glycoside 12 and 15 with ammonia-saturated ether gave products (14) and (17), respectively. The glycosidation of 5 with 11 followed by treatment with ammonia-saturated ether gave compounds (18) and (19), respectively. The second step glycosidations of 14 and 17 with methyl 2, 3, 4-tri-ο-acetyl-α-D-glucuronatopyranosyl bromide (20) gave diglycoside derivatives (23) and (24), respectively, and that of 18 with 2, 3, 4, 6-tetra-O-acetyl-α-D-glucopyranosyl bromide (21) and -α-D-galactopyranosyl bromide (22) gave deglycoside derivatives (25) and (26), respectively. The removal of the protecting groups of 23-26 gave diglycosides 27-30, respectively, having a β-D-glucuronopyranose (β-D-glcUA) as one of two sugar components in the molecules. The cytoprotective effects of the synthesized glycosides 27-30 on carbon tetrachloride (CCl4)-induced hepatotoxicity in vivo were compared with deglycosides 31-33 having only neutral sugar components, and naturally occurring glycyrrhizin (34) having two acidic sugar components (β-D-glcUA). While glycosides 31-33 had no cytoprotective effect, glycosides 27-30 showed potent effects. Especially, 27 and 28, having a β-D-glcUA as the terminal sugar component, were more effective meterials against hepatic injury than glycyrrhizin 34.

  采用分步糖苷化法构建了具有β(1→2)连接的二糖的甘草酸β-糖苷（27-30），这些二糖包括2-O-β-D-氟尿喹喃糖基-β-D-葡萄糖、2-O-β-D-古糖喹喃糖基-β-D-半乳糖、2-O-β-D-葡萄糖喹喃糖基-β-D-古糖和2-O-β-D-半乳糖喹喃糖基-β-D-古糖。在第一次糖苷化中，使用了2-O-三氯乙酰-β-D-吡喃糖氯化物（9-11）作为起始糖衍生物，与甘草酸甲酯（5）反应：5与9和10的糖苷化分别得到了β-和α-单糖苷（12）和（13），以及（15）和（16）。 β-糖苷12和15与氨饱和醚反应后分别得到产物（14）和（17）。5与11的糖苷化，再与氨饱和醚反应，分别得到了化合物（18）和（19）。14和17与甲基2, 3, 4-三-O-乙酰-α-D-古糖喹喃糖溴化物（20）的第二步糖苷化分别得到二糖苷衍生物（23）和（24），而18与2, 3, 4, 6-四-O-乙酰-α-D-葡萄糖喹喃糖溴化物（21）和-α-D-半乳糖喹喃糖溴化物（22）的糖苷化分别得到去糖苷衍生物（25）和（26）。去除23-26的保护基团分别得到二糖苷27-30，这些化合物在分子中有一个β-D-古糖喹喃糖（β-D-glcUA）作为两个糖组分之一。合成的糖苷27-30对四氯化碳（CCl4）诱导的肝毒性在体内的细胞保护作用与去糖苷31-33（只有中性糖组分）及天然存在的甘草苷（34，具有两个酸性糖组分 β-D-glcUA）进行了比较。虽然糖苷31-33没有细胞保护作用，但糖苷27-30显示出显著的作用。尤其是，27和28作为末端糖组分具有β-D-glcUA，比甘草苷34对肝损伤的保护效果更佳。
• Galactosylation of Monosaccharide Derivatives of Glycyrrhetinic Acid by UDP-Glycosyltransferase GmSGT2 from <i>Glycine max</i>
  作者：Yanan Gao、Liang Zhang、Xudong Feng、Xiaofei Liu、Fang Guo、Bo Lv、Chun Li

  DOI：10.1021/acs.jafc.0c03842

  日期：2020.8.12

  Glycyrrhetinic acid (GA), a pentacyclic triterpenoid aglycone, is the major functional component in licorice which mainly exists in the form of functional glycosides in licorice. The introduction of a sugar moiety to the C-3 OH of GA to yield glycosylated derivatives has been reported, but the late-stage glycosylation of GA-3-O-sugar to form rare GA glycosides with more complexed glycosyl decoration has been rarely reported. In this study, a unique UDP-galactosyltransferase GmSGT2 from Glycine max was found to transfer a galactose to the C2 position of the sugar moiety of GA-3-O-monoglucuronide (GAMG) and GA-3-O-monoglucose. In addition to UDP-galactose, GmSGT2 also recognizes UDP-glucose, UDP-xylose, and UDP-arabinose with relative activities of 32.1-89.2%. Based on a test of 12 typical natural products, GmSGT2 showed high specificity toward the pentacyclic triterpenoid skeleton as the sugar acceptor. Molecular docking was performed to elucidate the substrate recognition mechanism of GmSGT2 toward GAMG.