3-O-β-D-galactopyranosyloleanolic acid | 15596-19-7

• 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
• 英文名称: 3-O-β-D-galactopyranosyloleanolic acid
• 英文别名: (4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-2,2,6a,6b,9,9,12a-heptamethyl-10-[(2R,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
• CAS: 15596-19-7
• 化学式: C₃₆H₅₈O₈
• 分子量: 618.852
• InChiKey: ZNFRITHWVZXJRK-CZVPAOHUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  137
• 氢给体数：
  5
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-O-(2,3,4,6-tetra-O-benzoyl-β-D-galactopyranosyl)oleanolic acid 在 sodium methylate 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 生成 3-O-β-D-galactopyranosyloleanolic acid
  参考文献：
  名称：

  齐墩果酸单糖苷和二糖苷的简便合成。

  摘要：

  齐墩果酸及其苷类是重要的天然产物，具有多种有吸引力的生物活性，如抗肿瘤、抗病毒和抗炎特性。在目前的工作中，15 种带有各种糖基的齐墩果酸皂苷，包括 3-单糖苷、28-单糖苷和 3,28-二糖苷，很容易以高产率合成。选择苄基作为 COOH(28) 基团的保护基团，而不是常用的甲基和烯丙基，以避免最终脱保护的困难。发现碱促进羧酸与溴糖苷的缩合在 28-糖苷的合成中更有效。研究了两种方法并证明在制备 3,28-二糖苷中是可行的。

  DOI：

  10.3390/molecules13071472

文献信息

• Synthesis and Anti-Fungal Activity of Seven Oleanolic Acid Glycosides
  作者：Hanqing Zhao、Guanghui Zong、Jianjun Zhang、Daoquan Wang、Xiaomei Liang

  DOI：10.3390/molecules16021113

  日期：——

  In order to develop potential anti-fungal agents, seven glycoconjugates composed of a-L-rhamnose, 6-deoxy-a-L-talose, b-D-galactose, a-D-mannose, b-D-xylose-(1®4)-6-deoxy-a-L-talose, b-D-galactose-(1®4)-a-L-rhamnose, b-D-galactose-(1®3)-b-D-xylose-(1®4)-6-deoxy-a-L-talose as the glycone and oleanolic acid as the aglycone were synthesized in an efficient and practical way using glycosyl trichloroacetimidates as donors. The structures of the new compounds were confirmed by MS, 1H-NMR and 13C- NMR. Preliminary studies based on means of mycelium growth rate, indicated that all the compounds possess certain fungicidal activity against Sclerotinia sclerotiorum (Lib.) de Bary, Rhizoctonia solani Kuhn, Botrytis cinerea Pers and Phytophthora parasitica Dast.

  为了开发潜在的抗真菌药剂，七种糖苷结合物由 a-L 鼠李糖、6-脱氧-a-L-塔尔糖、b-D-半乳糖、a-D-甘露糖、b-D-木糖-(1®4)-6-脱氧-a-L-塔尔糖、b-D-半乳糖-(1®4)-a-L-鼠李糖组成、以三氯乙酰亚氨酸糖基化合物为供体，高效、实用地合成了以 b-D-半乳糖-(1®3)-b-D-木糖-(1®4)-6-脱氧-a-L-塔罗糖为糖酮、齐墩果酸为苷元的新化合物。新化合物的结构已通过 MS、1H-NMR 和 13C NMR 得到证实。基于菌丝生长速率的初步研究表明，所有化合物都对 Sclerotinia sclerotiorum (Lib.) de Bary、Rhizoctonia solani Kuhn、Botrytis cinerea Pers 和 Phytophthora parasitica Dast 具有一定的杀菌活性。
• USE OF URSOLIC ACID SAPONIN,OLEANOLIC ACID SAPONIN IN PREPARATION OF INCREASING LEUCOCYTES AND/OR PLATELET MEDICINE
  申请人：Guang Bing

  公开号：US20100197898A1

  公开（公告）日：2010-08-05

  The invention provides the use of ursolic acid saponin and oleanolic acid saponin of formula (I) in preparing medicaments for increasing leucocytes and/or platelets. The invention also provides a pharmaceutical composition containing the same compound. The invention utilizes the cheap and accessible ursolic acid and oleanolic acid which are widely present in natural plants as raw materials, introduces monosaccharyls or oligosaccharyls by structural modification. It is proved by pharmacological tests that the compound of formula (I) have an activity of obviously increasing leucocytes and/or platelets.

  本发明提供了使用式(I)的熊果酸皂苷和齐墩果酸皂苷制备增加白细胞和/或血小板的药物的方法。本发明还提供了含有相同化合物的制药组合物。本发明利用廉价且易得的熊果酸和齐墩果酸，它们广泛存在于天然植物中作为原料，并通过结构修饰引入单糖或寡糖。药理学试验证明，式(I)化合物具有明显增加白细胞和/或血小板的活性。
• Facile Synthesis of Oleanolic Acid Monoglycosides and Diglycosides
  作者：Yu Sha、Mao-Cai Yan、Jiao Liu、Yang Liu、Mao-Sheng Cheng

  DOI：10.3390/molecules13071472

  日期：——

  condensation of the carboxylic acid with bromo-glycosides was found to be more efficient in the synthesis of 28-glycosides. Two approaches were investigated and proved practicable in the preparation of 3,28- diglycosides. This method is suitable for preparing oleanolic acid glycosides with structural diversity for extensive biological evaluation and structure-activity relationship study, and it also apply new

  齐墩果酸及其苷类是重要的天然产物，具有多种有吸引力的生物活性，如抗肿瘤、抗病毒和抗炎特性。在目前的工作中，15 种带有各种糖基的齐墩果酸皂苷，包括 3-单糖苷、28-单糖苷和 3,28-二糖苷，很容易以高产率合成。选择苄基作为 COOH(28) 基团的保护基团，而不是常用的甲基和烯丙基，以避免最终脱保护的困难。发现碱促进羧酸与溴糖苷的缩合在 28-糖苷的合成中更有效。研究了两种方法并证明在制备 3,28-二糖苷中是可行的。
• Polyacanthoside A, a new oleanane-type triterpenoid saponin with cytotoxic effects from the leaves of <i>Acacia polyacantha</i> (Fabaceae)
  作者：Ghislain Fotso W.、Jean Na-Iya、Armelle Mbaveng T.、Patrick Ango Yves、Ibrahim Demirtas、Victor Kuete、Yeboah Samuel、Bathelemy Ngameni、Thomas Efferth、Bonaventure Ngadjui T.

  DOI：10.1080/14786419.2018.1486312

  日期：2019.12.17

  The chemical investigation of the leaves and stem bark of Acacia polyacantha (Fabaceae) led to the isolation of a new oleanane-type triterpenoid saponin named polyacanthoside A 1 together with fifteen known compounds. Their structures were established from spectral , mainly HRESIMS, 1D NMR and 2D NMR and by comparison with literature data. The cytotoxicity of compound 1 and the analogues 8 as well

  对金合欢（Fabaceae）的叶子和茎皮进行化学研究后，分离出了一种名为聚棘皮苷A 1的新型齐墩果型三萜皂苷和十五种已知化合物。它们的结构由光谱，主要是HRESIMS，1D NMR和2D NMR建立，并与文献数据进行比较。在包括敏感和耐药表型的9种癌细胞系中确定了化合物1和类似物8以及阿霉素的细胞毒性。与类似物8不同，化合物1和阿霉素在所有9种测试的IC 50癌细胞系中均显示出细胞毒性作用化合物1的值范围从8.90μM（对CCRF-CEM白血病细胞）到35.21μM（对HepG2肝癌细胞），对于阿霉素，范围从0.02μM（对CCRF-CEM白血病细胞）到66.83μM（对CEM / ADR5000白血病细胞）。 。
• Synthesis and α-glucosidase inhibitory activity of oleanolic acid derivatives
  作者：Shan Qian、Jiao Hai Li、Yu Wei Zhang、Xin Chen、Yong Wu

  DOI：10.1080/10286020903405456

  日期：2010.1.1

  Glucosidations of oleanolic acid (1) and its dihydroxy-olide derivatives (2) were carried out to provide eight glycosides. All synthesized compounds were evaluated by in vitro -glucosidase inhibitory activity assay. 3-Acetyl dihydroxy-olide oleanolic derivative 15 showed the most potent inhibitory effect. Structure-activity relationships within these compounds are discussed.