benzyl oleanolate 3-O-α-L-arabinopyranoside | 875878-33-4

• 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: benzyl oleanolate 3-O-α-L-arabinopyranoside
• 英文别名: 3-O-β-D-arabinopyranose oleanolic acid benzyl ester；benzyl (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2S,3R,4S,5S)-3,4,5-trihydroxyoxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylate
• CAS: 875878-33-4
• 化学式: C₄₂H₆₂O₇
• 分子量: 678.95
• InChiKey: CQDREFSDTPWHJT-BGLULPNGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.8
• 重原子数：
  49
• 可旋转键数：
  6
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  benzyl oleanolate 3-O-α-L-arabinopyranoside 在 三氟甲磺酸三甲基硅酯 、 对甲苯磺酸 作用下， 以 甲醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 9.0h， 生成 benzyl oleanolate 3-O-2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl-(1→2)-4-O-acetyl-α-L-arabinopyranoside
  参考文献：
  名称：

  Facile Synthesis of the Naturally Cytotoxic Triterpenoid Saponin Patrinia-Glycoside B-II and Its Conformer

  摘要：

  首次以线性 11 步序列 11 完成了天然三萜皂苷 Patrinia-glycoside B-II 即齐墩果酸 3-O-α-L-rhamnopyranosyl-(1→2)-[β-D-Gluco-pyranosyl-(1→3)]-α-L-arabinopyranoside 的化学合成，总收率为 9.4%。研究发现，阿拉伯糖残基的异常 1C4 构象是在制备中间体的过程中通过构象波动产生的。分子机理和量子化学计算表明，在正常条件下，帕特里尼亚糖苷 B-II 及其构象 1 不能相互转化。初步的结构-活性关系研究表明，独特的α-L-吡喃鼠李糖基-(1→2)-α-L-阿拉伯吡喃糖基二糖分子中阿拉伯糖残基的 4C1 椅构象是其对肿瘤具有细胞毒性活性的主要积极因素之一。

  DOI：

  10.3390/molecules181215193
• 作为产物：
  描述：

  溴甲苯 在 三氟甲磺酸三甲基硅酯 、 sodium methylate 、 potassium carbonate 作用下， 以 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 benzyl oleanolate 3-O-α-L-arabinopyranoside
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Raddeanin A, a Triterpene Saponin Isolated from <i>Anemone raddeana</i>

  摘要：

  首先，合成了一种具有细胞毒性的齐墩果酸类三萜皂甙 Raddeanin A，它是从 Anemone raddeana REGEL 中分离出来的。以齐墩果酸为原料，以阿拉伯糖基、葡萄糖基和鼠李糖基三氯乙酰亚氨酸为供体，采用逐步糖基化的方法进行合成。通过 1H-NMR、13C-NMR、IR、MS 和元素分析确认了 Raddeanin A 的化学结构，阐明其结构为 3-O-α-L-rhamnopyranosyl-(1→2)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranoside oleanolic acid。生物活性测试表明，在低浓度范围内，Raddeanin A 对组蛋白去乙酰化酶（HDACs）具有中等程度的抑制活性，这表明 Raddeanin A 的 HDACs 抑制活性可能是其细胞毒性的原因之一。

  DOI：

  10.1248/cpb.c14-00138

文献信息

• 一种改良的Fischer型糖苷化反应在构建皂苷 中糖苷键的应用
  申请人：扬州蓝色生物医药科技有限公司

  公开号：CN104693266B

  公开（公告）日：2018-03-23

  本发明属于有机合成领域，涉及一种皂苷的合成方法，具体涉及一种构建皂苷中糖苷键的方法，包括如下步骤：采用过量的醛糖或酮糖直接与苷元在适合的有机溶剂中，在酸性催化剂作用下，于30oC至回流温度下，反应得到目标产物皂苷。
• Synthesis and antitumor activity evaluation of oleanolic acid saponins bearing an acetylated l-arabinose moiety
  作者：Ye Zhong、Hui-ning Li、Lin Zhou、Hua-sheng Su、Mao-sheng Cheng、Yang Liu

  DOI：10.1016/j.carres.2021.108311

  日期：2021.5

  derivatives bearing acetyl-substituted l-arabinose moiety has been synthesized and screened in vitro for cytotoxicity against ten cancer cell lines and four normal cell lines. The antiproliferative evaluation indicated that synthetic derivatives showed excellent selectivity, as they were toxic against only A431 cell line. Among them, the compound 6 possesses the best inhibitory activity. A series of

  甲小号轴承乙酰基取代的齐墩果酸衍生物的eries升-arabinose部分已经合成和筛选体外针对10癌细胞系和四个正常细胞系的细胞毒性。抗增殖评估表明合成衍生物显示出极好的选择性，因为它们仅对 A431 细胞系有毒。其中，化合物6具有最好的抑制活性。一系列药理实验表明，化合物6显着诱导A431细胞凋亡和细胞周期阻滞，可作为进一步研究的潜在先导候选物。
• Synthesis and Tumor Cytotoxicity of Novel Amide Derivatives of β-Hederin
  作者：Yang Liu、Wen-Xiang Lu、Mao-Cai Yan、Yang Yu、Takashi Ikejima、Mao-Sheng Cheng

  DOI：10.3390/molecules15117871

  日期：——

  Thirteen novel triterpenoid saponins, designed as amide derivatives of the natural cytotoxic saponin β-hederin, were synthesized by a stepwise glycosylation strategy. The in vitro cytotoxic activity of these compounds was evaluated against five different tumor cell lines. Most of the evaluated compounds showed effective inhibitory activity against at least one tumor cell line at micromolar concentrations. The preliminary structure-activity relationships (SAR) indicate that mide derivatization at C-28 resulted in highly cytotoxic derivatives on specific tumor cell lines, and also resulted in an increase in the antitumor selectivity of β-hederin.

  通过逐步糖基化策略合成了 13 种新型三萜皂苷，设计为天然细胞毒性皂苷 β-常春藤素的酰胺衍生物。针对五种不同的肿瘤细胞系评估了这些化合物的体外细胞毒活性。大多数评估的化合物在微摩尔浓度下对至少一种肿瘤细胞系表现出有效的抑制活性。初步的构效关系（SAR）表明，C-28位点的mide衍生化产生了对特定肿瘤细胞系具有高度细胞毒性的衍生物，并且还导致β-常春藤素的抗肿瘤选择性增加。
• Facile Synthesis of Four Natural Triterpene Saponins with Important Antitumor Activity
  作者：Tiantian Guo、Qingchao Liu、Lei Zhang、Peng Wang、Yingxia Li

  DOI：10.1080/00397910903576602

  日期：2011.1.25

  The first synthesis of four natural triterpene saponins, which exhibit significant antitumor activities, was concisely achieved by adopting a stepwise glycosylation. The key intermediate 13 was afforded via Bu2SnO-mediated regioseletive benzoylation. During the preparation of the target compounds, it was found that the α-L-arabinopyranosyl unit in intermediates 17 and 20 existed in the unusual 1 C

  通过采用逐步糖基化，首次合成了四种具有显着抗肿瘤活性的天然三萜皂苷。关键中间体 13 是通过 Bu2SnO 介导的区域选择性苯甲酰化得到的。在目标化合物的制备过程中，发现中间体17和20中的α-L-阿拉伯吡喃糖基单元以异常的1 C 4 构象存在，去除苯甲酰基后，α-L-阿拉伯吡喃糖基单元在典型的 4 C 1 形式。
• Synthesis, biological evaluation and structure-activity relationship studies of hederacolchiside E and its derivatives as potential anti-Alzheimer agents
  作者：Hui-ning Li、Yang Liu、Zuo-peng Zhang、Zhi-peng Wang、Jing-zheng Hao、Feng-ran Li、Zhan-fang Fan、Li-bo Zou、Mao-sheng Cheng

  DOI：10.1016/j.ejmech.2017.11.040

  日期：2018.1

  Inspired by the previously reported neuroprotective activity of hederacolchiside E (1), we synthesized hederacolchiside E for the first time along with eleven of its derivatives. The neuroprotective effects of these compounds were further evaluated against H2O2- and A beta(1-42)-induced injury using cell-based assays. The derivatives showed obvious differences in activity due to structural variations, and two of them exhibited better neuroprotective effects than 1 in the A beta(1-42)-induced injury model. Compound 7 was the most active derivative and had a relatively simple chemical structure. Moreover, 1 and 7 can significantly reduce the release of lactate dehydrogenase (LDH), level of intracellular reactive oxygen species (ROS) and extent of malondialdehyde (MDA) increase resulting from A beta(1-42) treatment, which demonstrated that these kinds of compounds show neuroprotective effects in Alzheimer's disease (AD) models via modulating oxidative stress. Compound 7 could be used as promising lead for the development of a new type of neuroprotective agent against AD. (C) 2017 Elsevier Masson SAS. All rights reserved.