oleanolic acid trityl ester | 257614-49-6

• 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: oleanolic acid trityl ester
• 英文别名: trityl oleanolic ester；trityl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 257614-49-6
• 化学式: C₄₉H₆₂O₃
• 分子量: 699.029
• InChiKey: XTYGQGPGUORMOP-AIXUNDJFSA-N

物化性质

• 沸点：
  726.4±60.0 °C(Predicted)
• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  12.5
• 重原子数：
  52
• 可旋转键数：
  6
• 环数：
  8.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  oleanolic acid trityl ester 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 6.0h， 生成 androseptoside A
  参考文献：
  名称：

  一系列作为α-葡萄糖苷酶和α-淀粉酶抑制剂的齐墩果酸皂苷的合成与评价

  摘要：

  以一种有效且实用的策略合成了 16 种天然存在的齐墩果酸皂苷及其衍生物，并在体外评估了它们对 α-葡萄糖苷酶和 α-淀粉酶的抑制活性。在所有化合物中，28-O-单糖苷 8 对 α-葡萄糖苷酶表现出显着的抑制活性，IC50 值为 87.3 µM，是抗糖尿病阿卡波糖的 5 倍。根据初步的构效关系，对于 28-O-单糖苷，末端 α-l-吡喃鼠李糖残基的存在增强了 α-葡萄糖苷酶和 α-淀粉酶的抑制活性。此外，对于 3,28-O-bidesmosides，

  DOI：

  10.1002/ardp.201500179
• 作为产物：
  描述：

  齐墩果酸 、 三苯基氯甲烷 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 四氢呋喃 为溶剂， 以100%的产率得到oleanolic acid trityl ester
  参考文献：
  名称：

  First Synthesis of a Bidesmosidic Triterpene Saponin by a Highly Efficient Procedure

  摘要：

  DOI：

  10.1021/ja9926818

文献信息

• Synthesis of flaccidoside II, a bidesmosidic triterpene saponin isolated from Chinese folk medicine Di Wu
  作者：Shuihong Cheng、Yuguo Du、Feihong Bing、Guobin Zhang

  DOI：10.1016/j.carres.2007.11.015

  日期：2008.2

  A total synthesis of flaccidoside II, 3-O-alpha-L-rhamnopyranosyl-(1-->2)-beta-D-xylopyranosyloleanolic acid 28-O-alpha-L-rhamnopyranosyl-(1-->4)-beta-D-glucopyranosyl-(1-->6)-beta-D-glucopyranoside, isolated from Chinese folk medicine Di Wu, has been accomplished from building blocks isopropyl 2-O-acetyl-3,4-di-O-benzoyl-1-thio-beta-D-xylopyranoside, 2,3,4-tri-O-benzoyl-alpha-L-rhamnopyranosyl trichloroacetimidate

  总黄酮苷II，3-O-α-L-鼠李吡喃糖基-（1-> 2）-β-D-吡喃并吡喃基果酸28-O-α-L-鼠李吡喃糖基-（1-> 4）-β -D-吡喃葡萄糖基-（1-> 6）-β-D-吡喃葡萄糖苷是从异丙基2-O-乙酰基-3,4-二-O-苯甲酰基-的结构单元中分离而来的1-硫代-β-D-吡喃吡喃糖苷，2,3,4-三-O-苯甲酰基-α-L-鼠李吡喃糖基三氯乙酰亚胺酸酯，齐墩果酸三苯甲基酯，2,3-二-O-乙酰基-6-O-苯甲酰基乙酯-1-硫代-β-D-吡喃葡萄糖苷和4-甲氧基苯基2,3,4-三-O-乙酰基-β-D-吡喃葡萄糖苷。使用部分保护的硫糖基供体可大大简化目标皂苷的合成。
• Concise Synthesis and Antidiabetic Effect of Three Natural Triterpenoid Saponins Isolated from<i>Fadogia ancylantha</i>(Makoni tea)
  作者：Zi-Li Feng、Shao-Ping Wu、Wen-Hong Li、Tian-Tian Guo、Qing-Chao Liu

  DOI：10.1002/hlca.201500061

  日期：2015.9

  The first concise synthesis of the bidesmosidic oleanolic acid saponins 1–3 isolated from Fadogia ancylantha (Makoni tea) have been accomplished through a ‘one‐pot sequential glycosylation’ strategy with two glycosyl 1‐(trichloroacetimidate)s as glycosyl donors. The synthesized natural products 1–3 were then evaluated for their inhibitory activities against α‐glucosidase, α‐amylase, and lipase. Among

  所述bidesmosidic齐墩果酸皂甙的第一简明合成1 - 3从分离Fadogia ancylantha “ -锅顺序的糖基化一个”具有两个糖基1-（三氯乙酰亚胺酯）S作为糖供体的策略（马科尼茶）已通过来完成的。将合成的天然产物1 - 3然后评价它们对抑制活性α-葡糖苷酶，α-淀粉酶，和脂肪酶。间的测定化合物1 - 3，化合物1表现出较强的α-葡萄糖苷酶和α-淀粉酶抑制，IC 50的160和180μ值中号分别。更以上，化合物2和3显示出对强抑制α葡糖苷酶和脂肪酶，与respectivement IC 50个的170和190μ值中号，以及190和200μ中号。
• Synthesis and cytotoxic activity of the N-acetylglucosamine-bearing triterpenoid saponins
  作者：Peng Wang、Jun Wang、TianTian Guo、Yingxia Li

  DOI：10.1016/j.carres.2010.01.002

  日期：2010.3

  Fourteen ursolic acid and oleanolic acid saponins with N-acetyl-beta-D-glucosamine, and (1 -> 4)-linked and (1 6)-linked N-acetyl-beta-D-glucosamine oligosaccharide residues were synthesized in a convergent manner. The structures of all compounds were confirmed by (1)H NMR and (13)C NMR spectroscopy and by mass spectrometry, and their cytotoxic activities were assayed in three cancer cell lines. Only oleanolic acid-3-yl beta-D-GluNAc showed significant cytotoxicity against HL-60 and BGC-823. (C) 2010 Published by Elsevier Ltd.
• Synthesis and biological evaluation of oleanolic acid derivatives as PTP1B inhibitors
  作者：Qing-Chao Liu、Tian-Tian Guo、Lei Zhang、Yue Yu、Peng Wang、Ju-Fang Yang、Ying-Xia Li

  DOI：10.1016/j.ejmech.2013.03.001

  日期：2013.5

  Twenty-four sugar-substituted oleanolic acid derivatives (1a-1f, 2a-2j, and 3a-3h) were synthesized in a concise and efficient strategy and their effects on the inhibition of protein tyrosine phosphatase 1B (PTP1B) and insulin-sensitizing response were evaluated in vitro. Several derivatives showed moderate to good inhibitory activities against PTP1B, and especially compounds 2f, 2h, 3d and 3e exhibited the most potent inhibitory activities with the IC50 values of 1.91, 12.2, 9.21 and 0.56 mu M against PTP1B, respectively. Furthermore, compounds 2g-2h and 3b-3e displayed good insulin-sensitizing activities with the response values ranging from 21.52% to 59.58%. Structure-activity relationship study of these sugar-substituted oleanolic acid derivatives demonstrated that PTP1B inhibitory activity and insulin-sensitizing response were strongly influenced by both the carbohydrate moiety at the C-3 position and the long acidic chain at C-28 position of oleanolic acid. (C) 2013 Elsevier Masson SAS. All rights reserved.
• Synthesis of oleanolic acid saponins mimicking components of Chinese folk medicine Di Wu
  作者：Xing Huang、Shuihong Cheng、Yuguo Du、Feihong Bing

  DOI：10.1016/j.carres.2009.04.005

  日期：2009.7

  3,28-Di-O-rhamnosylated oleanolic acid saponins, mimicking components of Chinese folk medicine Di Wu, have been designed and synthesized. one-pot glycosylation and 'inverse procedure' technologies have been applied thus significantly simplifying the preparation of desired saponins. The cytotoxic activity of compounds 3-O-[alpha-L-rhamnopyranosyl-(1 -> 2)-beta-D-xylopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl-(1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (3), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl- (1 -> 4)-beta-D-glucopyranosyl-(1 -> 6)-beta-D-glucopyranosyl] ester (4), 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[alpha-L-rhamnopyranosyl] ester (5), and 3-O-[alpha-L-rhamnopyranosyl]oleanolic acid 28-O-[6-O-(alpha-L-rhamnopyranosyl)hexyl] ester (6) was preliminarily evaluated against HL-60 human promyelocytic leukemia cells. The natural saponin 3 and designed saponin 4 exhibited comparable moderate cytotoxic activity under our testing conditions. (C) 2009 Elsevier Ltd. All rights reserved.