30-stearyl glycyrrhizin | 135459-36-8

• 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: 30-stearyl glycyrrhizin
• 英文别名: (2S,3S,4S,5R,6R)-6-[(2R,3R,4S,5S,6S)-2-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-4,4,6a,6b,8a,11,14b-heptamethyl-11-octadecoxycarbonyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-6-carboxy-4,5-dihydroxyoxan-3-yl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid
• CAS: 135459-36-8
• 化学式: C₆₀H₉₈O₁₆
• 分子量: 1075.43
• InChiKey: BNHBSCYXNNWQIT-UDXCNHPRSA-N

物化性质

• 沸点：
  1040.3±65.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.9
• 重原子数：
  76
• 可旋转键数：
  25
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  256
• 氢给体数：
  7
• 氢受体数：
  16

反应信息

• 作为反应物：
  描述：

  30-stearyl glycyrrhizin 在 pyridine-SO3 complex 作用下， 以 吡啶 为溶剂， 反应 24.0h， 生成 (2S,3R,4R,5R,6R)-6-[[(3S,4aR,6aR,6bS,8aS,11S,12aR,14aR,14bS)-4,4,6a,6b,8a,11,14b-heptamethyl-11-octadecoxycarbonyl-14-oxo-2,3,4a,5,6,7,8,9,10,12,12a,14a-dodecahydro-1H-picen-3-yl]oxy]-5-[(2R,3R,4S,5R,6S)-6-carboxy-3,4,5-trisulfooxyoxan-2-yl]oxy-3,4-disulfooxyoxane-2-carboxylic acid
  参考文献：
  名称：

  Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds

  摘要：

  Sodium sulfates 11-14, 29-32, 35 and 37 of various alkyl glycyrrhizin and related compounds were synthesized. In vitro anti-HIV activities of the sulfates were compared to the activities of glycyrrhizin 1 in the inhibition of replications of HTLV-III and GUN-4. The activities of the sulfates were increased 11.1, 15.2, 9.1 and 5.0 times for 11-14, 100.0, 125.5, 83.3 and 11.6 times for 29-32, and 11.6 and 50.0 times for 35 and 37. From the relationship between CMC values and anti-HIV activities of the sulfates, it appeared that the sulfates exhibiting more potent antiviral activities had higher micelle forming abilities. Sodium sulfates having a triterpenoid or steroid ring in the molecule showed more potent activities than those of thioglycosides which had no such ring. From the investigation of syncytium formation, we suggest that the active sulfates inhibited HIV-1 infection early in the replication cycle of the virus.

  DOI：

  10.1016/0223-5234(96)89163-x
• 作为产物：
  描述：

  (3beta,20beta)-20-羧基-11-氧代-30-去甲齐墩果-12-烯-3-基 2-O-beta-D-吡喃葡糖基-beta-D-吡喃葡糖苷酸 在 palladium on activated charcoal 氢气 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 、 异丙醇 为溶剂， 85.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 30-stearyl glycyrrhizin
  参考文献：
  名称：

  Targeting of liposomes surface-modified with glycyrrhizin to the liver. I. Preparation and biological disoposition.

  摘要：

  我们认为甘草酸是一种新的脂质体肝靶向配体，因为已知在大鼠静脉注射后，约80%的甘草酸会排泄到胆汁中。为了用甘草酸修饰脂质体表面，合成了30-硬脂酰甘草酸（GLOSt），这是一种脂溶性甘草酸衍生物。通过核磁共振（NMR）、红外（IR）和质谱（MS）鉴定了这种新化合物的结构。从氢化卵磷脂-胆固醇-GLOSt或二鲸蜡磷酸（DCP）（4:4:1）制备了超声处理的脂质体，并以[3H]菊粉作为水相标记物进行标记。通过测量封装效率和平均直径确认，含有GLOSt的超声处理脂质体（GLOSt-SUV）与含有DCP的对照脂质体（对照-SUV）一样，都是小单层脂质体（SUV）类型。在大鼠静脉注射总脂质量为90 μmol/kg体重4小时后，GLOSt-SUV在肝脏中的积累比对照-SUV多4倍（42.4%）。因此，甘草酸被认为是一种有用的脂质体肝靶向新配体。

  DOI：

  10.1248/cpb.39.1004

文献信息

• Targeting of liposomes surface-modified with glycyrrhizin to the liver. I. Preparation and biological disoposition.
  作者：Hideki TSUJI、Sayoko OSAKA、Hiroshi KIWADA

  DOI：10.1248/cpb.39.1004

  日期：——

  We consider glycyrrhizin to be a new ligand for liposomes to the liver because it is known that about 80% of glycyrrhizin is excreted into the bile after intravenous administration in rats. In order to modify the liposomal surface with glycyrrhizin, 30-stearyl glycyrrhizin (GLOSt), one of the lipophilic glycyrrhizin derivatives, was synthesized. The structure of this new compound was identified by nuclear magnetic resonance (NMR), infrared (IR) and mass spectra (MS). Sonicated liposomes were prepared from hydrogenated egg phosphatidylcholine-cholesterol-GLOSt or dicetyl phosphate (DCP)(4 : 4 : 1) and were labelled with [3H]inulin as an aqueous marker. It was confirmed by measuring the encapsulation efficiencies and the mean diameters that GLOSt-containing sonicated liposomes (GLOSt-SUV) were SUV-type as well as DCP-containing control liposomes (control-SUV). Four hours after intravenous injection into rats at a dose of 90 μmol as total lipid per kg of rat body weight, GLOSt-SUV showed 4-fold more accumulation (42.4%) in the liver than control-SUV. Therefore, glycyrrhizin is considered to be a useful new ligand on liposomes for targeting to the liver.

  我们认为甘草酸是一种新的脂质体肝靶向配体，因为已知在大鼠静脉注射后，约80%的甘草酸会排泄到胆汁中。为了用甘草酸修饰脂质体表面，合成了30-硬脂酰甘草酸（GLOSt），这是一种脂溶性甘草酸衍生物。通过核磁共振（NMR）、红外（IR）和质谱（MS）鉴定了这种新化合物的结构。从氢化卵磷脂-胆固醇-GLOSt或二鲸蜡磷酸（DCP）（4:4:1）制备了超声处理的脂质体，并以[3H]菊粉作为水相标记物进行标记。通过测量封装效率和平均直径确认，含有GLOSt的超声处理脂质体（GLOSt-SUV）与含有DCP的对照脂质体（对照-SUV）一样，都是小单层脂质体（SUV）类型。在大鼠静脉注射总脂质量为90 μmol/kg体重4小时后，GLOSt-SUV在肝脏中的积累比对照-SUV多4倍（42.4%）。因此，甘草酸被认为是一种有用的脂质体肝靶向新配体。
• Synthetic studies on the relationship between anti-HIV activities and micelle forming abilities of various alkylated glycyrrhetinate diglycoside sodium sulfates and related compounds
  作者：S Saito、T Furumoto、M Ochiai、A Hosono、H Hoshino、U Haraguchi、R Ikeda、N Shimada

  DOI：10.1016/0223-5234(96)89163-x

  日期：1996.1

  Sodium sulfates 11-14, 29-32, 35 and 37 of various alkyl glycyrrhizin and related compounds were synthesized. In vitro anti-HIV activities of the sulfates were compared to the activities of glycyrrhizin 1 in the inhibition of replications of HTLV-III and GUN-4. The activities of the sulfates were increased 11.1, 15.2, 9.1 and 5.0 times for 11-14, 100.0, 125.5, 83.3 and 11.6 times for 29-32, and 11.6 and 50.0 times for 35 and 37. From the relationship between CMC values and anti-HIV activities of the sulfates, it appeared that the sulfates exhibiting more potent antiviral activities had higher micelle forming abilities. Sodium sulfates having a triterpenoid or steroid ring in the molecule showed more potent activities than those of thioglycosides which had no such ring. From the investigation of syncytium formation, we suggest that the active sulfates inhibited HIV-1 infection early in the replication cycle of the virus.