β-D-glucopyranosyl 3β-hydroxylup-20(29)-en-28-oate | 22333-85-3

• 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: β-D-glucopyranosyl 3β-hydroxylup-20(29)-en-28-oate
• 英文别名: 28-O-β-D-glucopyranosyl 3β-hydroxy-lup-20(29)-en-28-oate；28-O-β-D-glucopyranosyl betulinic acid；betulinic acid 28-O-β-D-glucoside；betulinic acid 28-O-β-D-glucopyranoside；[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl] (1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylate
• CAS: 22333-85-3
• 化学式: C₃₆H₅₈O₈
• 分子量: 618.852
• InChiKey: GPYJMOFNKRFSHT-XGUXKNSRSA-N

物化性质

• 熔点：
  234 °C
• 沸点：
  694.0±55.0 °C(Predicted)
• 密度：
  1.23±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  44
• 可旋转键数：
  5
• 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

• 作为反应物：
  描述：

  β-D-glucopyranosyl 3β-hydroxylup-20(29)-en-28-oate 在 enzyme β-glucosidase 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 72.0h， 生成 白桦脂酸
  参考文献：
  名称：

  Glucosidation of Betulinic Acid by Cunninghamella Species

  摘要：

  Microbial transformation of the antimelanoma agent betulinic acid (1) was studied. Preparative scale biotransformation with resting-cell suspensions of Cunninghamella species NRRL 5695 resulted in the production of a fungal metabolite of 1, which has been characterized as 28-O-beta-D-glucopyranosyl 3 beta-hydroxy-lup-20(29)-en-28-oate (2) based on spectral and enzymic data. The in vitro cytotoxicity assay of metabolite 2 revealed no activity against several human melanoma cell lines.

  DOI：

  10.1021/np980432b
• 作为产物：
  描述：

  白桦脂醇-3-乙酸酯 在 吡啶 、 氢氧化钾 、 sodium methylate 、 tBuOCrO3H 、 silver(l) oxide 作用下， 以 甲醇 为溶剂， 反应 3.0h， 生成 β-D-glucopyranosyl 3β-hydroxylup-20(29)-en-28-oate
  参考文献：
  名称：

  Synthesis of Glycosides of Lupane-Type Triterpene Acids

  摘要：

  A preparative synthesis of glucosides of the lupane-type triterpene acids betulinic, dihydrobetulinic, betulonic, dihydrobetulonic. and 3,20-dioxo-30-norlupan-28-oic was proposed. Glycosylation of 3-hydroxyacids by alpha-acetohronioglucose (ABG) with Ag2O was performed in pyridine (Py) to form glycosides at C-28, repeated glycosylation of which by these same reagents but in CH2Cl2 generated a glycoside bond at C-3 to form bisglucosides 28- Glucosides of ketoacids were formed in high yields in both Py and CH2Cl2.

  DOI：

  10.1023/b:conc.0000018113.79735.34

文献信息

• Synthesis and antiproliferative properties of new hydrophilic esters of triterpenic acids
  作者：Barbara Eignerova、Michal Tichy、Jana Krasulova、Miroslav Kvasnica、Lucie Rarova、Romana Christova、Milan Urban、Barbara Bednarczyk-Cwynar、Marian Hajduch、Jan Sarek

  DOI：10.1016/j.ejmech.2017.09.041

  日期：2017.11

  To improve the properties of cytotoxic triterpenoid acids 1–5, a large set of hydrophilic esters was synthesized. We choose betulinic acid (1), dihydrobetulinic acid (2), 21-oxoacid 3 along with highly active des-E lupane acids 4 and 5 as a model set of compounds for esterification of which the properties needed to be improved. As ester moieties were used - methoxyethanol and 2-(2-methoxyethoxy)ethanol

  为了提高细胞毒性三萜酸的性质1 - 5，一大组的亲水性酯的合成。我们选择了桦木酸（1），二氢桦木酸（2），21-含氧酸3以及高活性des-E戊烷酸4和5作为酯化化合物的模型集，其性能需要改善。作为酯部分，使用了-甲氧基乙醇和2-（2-甲氧基乙氧基）乙醇和羟基单元（a - d型），吡咯烷基乙醇，哌啶子基乙醇和吗啉代乙醇（f - h型）和单糖基团（i型-升）。结果，获得了56种三萜酸酯（49种新化合物），并测试了它们对四种癌细胞系和正常人成纤维细胞的细胞毒性。所有新化合物在所有测试浓度下均完全溶解，这曾经是母体化合物1和2的问题。 在至少一种癌细胞系中，有16种化合物的IC 50 <10μM，对四种测试的癌细胞系中的至少3种，细胞毒性<10μM。发现化合物3c的活性最高（在MCF7上为1.8μM，在HeLa上为2.8μM，在G-361细胞上为1.6μM），在最高测试浓度（50μM）下对非癌性B
• Antitumor agent
  申请人：The Nisshin OilliO, Ltd.

  公开号：US20030153538A1

  公开（公告）日：2003-08-14

  The present invention relates to an antitumor agent, which comprises, as an effective component, a compound selected from the group consisting of maslinic acid, erythrodiol, uvaol, betulinic acid, betulin and physiologically acceptable salts thereof or derivatives thereof.

  本发明涉及一种抗肿瘤剂，其包括作为有效成分的化合物，所述化合物选自橄榄酸、赤藓醇、尤瓦醇、白桦酸、白桦醇及其生理接受的盐或衍生物的组。
• Feeds and fertilizers containing pentacyclic triterpenes
  申请人：The Nisshin OilliO, Ltd.

  公开号：US20040175447A1

  公开（公告）日：2004-09-09

  The present invention relates to a feed, a fertilizer, a melanogenesis-inhibitory agent for animals and plants and a blackening/browning-inhibitory composition for animals and plants, each comprising, as an effective component, at least one member selected from the group consisting of pentacyclic triterpenes, physiologically acceptable salts thereof and derivatives thereof, which have an excellent melanogenesis-inhibitory effect.

  本发明涉及一种饲料、一种肥料、一种动植物黑色素生成抑制剂和一种动植物黑化/褐化抑制组合物，每种均包括至少一种选自五环三萜、其生理上可接受的盐和衍生物组成的群体中的有效成分，具有出色的黑色素生成抑制效果。
• Glycosylation of Triterpene Alcohols and Acids of the Lupane and A-Secolupane Series
  作者：Eva Klinotová、Václav Křeček、Jiří Klinot、Magdalena Endová、Jana Eisenreichová、Miloš Buděšínský、Martin Štícha

  DOI：10.1135/cccc19971776

  日期：——

  A series of 3- and 28-glucosides and glucosyl esters of betulinic acid (1a), 28-hydroxy-3,4-secolupa-4(23),20(29)-dien-3-oic acid (22a), dimethyl ester of 28-hydroxy-2,3-secolup-20(29)-en-2,3-dioic acid (43a), their 20(29)-dihydro derivatives (1b, 22b, 43b) and several other triterpenes of the lupane (12a, 12b) and 3,4-secolupane series (18a, 18b, 32a) has been prepared by reaction of tetra-O-acetyl-α-D-glucopyranosyl bromide in acetonitrile in the presence of mercury(II) cyanide and subsequent deacetylation of the obtained tetra-O-acetyl-β-D-glucopyranosyl derivatives. In several cases attempted glucosylation in the presence of silver silicate afforded predominantly the corresponding 1,2-orthoacetates of α-D-glucopyranose.

  一系列3-和28-葡萄糖苷和葡萄糖酯的萜烯酸（1a），28-羟基-3,4-环戊二烯-3-酸（22a），28-羟基-2,3-环戊烷-20-二烯-2,3-二酸二甲酯（43a），它们的20（29）-二氢衍生物（1b，22b，43b）和几种其他狼毒萜烯（12a，12b）和3,4-环戊烷系列（18a，18b，32a）已经通过在乙腈中存在汞（II）氰化物的情况下反应四个-O-乙酰-α-D-葡萄糖吡喃溴化物，并随后脱乙酰化所得的四个-O-乙酰-β-D-葡萄糖吡喃衍生物制备。在几种情况下，尝试在银硅酸盐存在下进行葡萄糖化主要得到相应的α-D-葡萄糖吡喃的1,2-正交醋酸酯。
• A New Potent Inhibitor against α-Glucosidase Based on an In Vitro Enzymatic Synthesis Approach
  作者：Huanyu Zhang、Xiance Che、Hongyan Jing、Yaowu Su、Wenqi Yang、Rubing Wang、Guoqi Zhang、Jie Meng、Wei Yuan、Juan Wang、Wenyuan Gao

  DOI：10.3390/molecules29040878

  日期：——

  Inhibiting the activity of intestinal α-glucosidase is considered an effective approach for treating type II diabetes mellitus (T2DM). In this study, we employed an in vitro enzymatic synthesis approach to synthesize four derivatives of natural products (NPs) for the discovery of therapeutic drugs for T2DM. Network pharmacology analysis revealed that the betulinic acid derivative P3 exerted its effects

  抑制肠道α-葡萄糖苷酶活性被认为是治疗II型糖尿病（T2DM）的有效方法。在这项研究中，我们采用体外酶促合成方法合成了四种天然产物（NP）衍生物，用于发现 T2DM 治疗药物。网络药理学分析表明，桦木酸衍生物P3通过多靶点发挥治疗T2DM的作用。神经活性配体-受体相互作用和钙信号通路被确定为参与化合物 P3 对 T2DM 治疗作用的关键信号通路。分子对接、分子动力学（MD）模拟和结合自由能计算结果表明，与阿卡波糖相比，化合物P3与α-葡萄糖苷酶表现出更稳定的结合相互作用和更低的结合能（-41.237 kcal/mol）。此外，化合物P3在各种药代动力学预测模型中表现出优异的特性。因此，P3有望作为T2DM药物开发的先导化合物，值得进一步探索。最后，我们进行定点诱变，实现了桦木酸衍生物的靶向合成。这项工作展示了从通过体外酶促合成技术合成的纳米粒子衍生物中发现新型抗高血糖药物的实用策略，为化合