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Synthesis of oleanolic disaccharide derivatives

Chinese Chemical Letters 2012年第4期23卷 403-406页

作者： Shu Chen Pei Jian Bo Wu Fan Lei Shan Qian Li Hai Yong Wu Key Laboratory of Drug Targeting and Drug Delivery System of the Education Ministry Department of Medicinal ChemistryWest China School of PharmacySichuan UniversityChengdu 610041China Bioengineering College Xihua UniversityChengdu 610039China

oleanolic acid 1 exists widely in food,medicinal herbs and other plants and possesses many attractive biological activities. Recently,some oleanolic derivatives were reported to have interesting anti-tumor ***,using association principle of drug design,OA disaccharide 17 was designed and synthesized by coupling a-L-rhamnopyranosyl-（1→2）-a-L-arabinopyranosyl disaccharide moiety,which has proved to be a unique sugar sequence with strongly antitumor activity,and modified OA with a nitrile at C-17.

关键词： oleanolic acid Rhamnopyranosyl Arabinopyranosyl Anti-tumor Association principle

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Thin Layer Chromatography and Chemometric Studies of Selected Potentilla Species

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American Journal of Analytical Chemistry 2014年第16期5卷 1109-1120页

作者： Ryszard Swieboda Agnieszka Józwiak Grzegorz Józwiak Monika Waksmundzka-Hajnos Department of Inorganic Chemistry Medical UniversityLublinPoland

Herbal medicinal products have a long-standing therapeutic record. To ensure the quality of herbal products specific identification tests which allow experts to discriminate related species and/or potential adulterants/substitutes are required. The purpose of the research was to recommend an original and simple method for the separation of closely related five triterpenic acids (ursolic, oleanolic, tormentic, euscaphic, pomolic acid) and its application to chemotaxonomy studies. 17 standard samples of Potentilla species and 3 test samples were chromatographed (with or without prechromatographic derivatization) on silica gel plates using the mobile phase: chloroform-diethyl ether-methanol-formic acid (30:10:1:0.2 v/v/v/v);they were subsequently derivatized, and visualized in UV 366 nm light. After images received pre-treatment (montaging stack, removal of noise, background subtract, horizontal equalization, two types of warping) exploratory analysis of the investigated Potentilla species fingerprints was processed. The method without prechromatographic derivatization was used to create differential fingerprints. Good results were obtained by the application of r-project iterative algorithm for subtract background and our simple algorithm for warping to image processing of TLC chromatograms for the first time.

关键词： Pomolic acid Ursolic acid Euscaphic acid Tormentic acid oleanolic acid Triterpene acids TLC Fingerprint Potentilla

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Qualitative and quantitative analysis of Chinese herb fructus chaenomelis

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Journal of Nanjing Medical University 2007年第1期21卷 51-54页

作者： Lina Chen School of Pharmacy Nanjing Medical University Nanjing 210029China

To establish reliable methods for evaluating the quality of Chinese herb fructus chaenomelis. Methods： Qualitative analysis by Thin layer chromatography （TLC） , reference substances were Chaenomeles speciosa （Sweet） Nakai and oleanolic acid, a mixed solvent of chloroform-methanol （40 ： 1 ） was employed as the mobile phase,color developing agent was 10% sulfuric acidethanol *** the system of high performance liquid chromatography （HPLC）, a Prontosil Eurobond C18 column （250 mm×4.0 mm,5μm ） was used,the mobile phase was composed of acetonitrile-methanol-0.4% ammonium acetate solution （55 ： 25 ： 20）, the flow rate was 1.0 ml/min with UV detected at 210 nm, the column temperature was maintained at room temperature. Results： In the system of TLC, oleanolic acid was separated successfully. In HPLC, the linear ranges of oleanolic acid and ursolic acid were 5.89-13.73 μg （R=0.9990）and 6.84-15.96μg （R=0.9990）, respectively. The average recoveries of oleanolic acid and ursolic acid were 97.52% （RSD=2 .58% ）, 98.21% （RSD=2.23%）, respectively. Conclusion： The established TLC method can easily distinguish Chinese herb fructus chaenomelis from other commonly used crude drugs of the same family .The HPLC method for determining oleanolic acid and ursolic acid is simple, reproducible, accurate and feasible. The methods reported in this paper can be used scientifically and effectively to evaluate the quality of Chinese herb fructus chaenomelis.

关键词： fructus chaenomelis TLC HPLC oleanolic acid ursolic acid

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A novel screening model for the molecular drug for diabetess and obesity based on tyrosine phosphatase Shpa

A novel screening model for the molecular drug for diabetess...

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“细胞活动生命活力”——中国细胞生物学学会全体会员代表大会暨第十二次学术大会

作者：布燕燕石涛蒙明慧孔贵萍田莹普陈全成姚新生冯根生陈海峰吕忠显厦门大学生命医学研究院

Tyrosine phosphatase Src-homology phosphotyrosyl phosphatase 2(Shp2) was identified as a potential molecular target for therapeutic treatment of diabetes and ***,there is still no systematic research on the enhancers for the Shp2 *** present study established a nove1 powerful mode1 for the high-throughput screening of Shp2 enhancers and successfully identified a new specific Shp2 enhancer, oleanolic acid,from Chinese herbs.

关键词： Shp2 enhancer Screening system Diabetes oleanolic acid

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Low barnacle fouling on leaves of the mangrove plant Sonneratia apetala and possible anti-barnacle defense strategies

Low barnacle fouling on leaves of the mangrove plant Sonnera...

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福建省海洋学会2016年学术年会

作者： Dan-qing Feng Wei Wang Xiang Wang Yan Qiu Cai-huan Ke College of Ocean & Earth Sciences Xiamen University Medical College Xiamen University

A field survey of barnacle fouling on leaves of five co-occurring mangrove plants(Kandelia candel,Bruguiera gymnorrhiza,Rhizophora stylosa,Sonneratia apetala,and Avicennia marina) was conducted in Tongan Bay,southeastern *** leaves of *** were found to be less frequently and less abundantly fouled by barnacles relative to the other mangrove species,implying that *** may possess anti-barnacle *** surface wettability and flexibility of leaves for the five investigated mangrove species were *** the lower surface of *** leaf,the leaves of all these species exhibited low surface wettability,with contact angles of 82° to 94°.The leaf flexibility of *** was similar to that of ***,and both were much greater than those of the other three mangrove *** of all these five mangrove species were also subjected to chemical *** extracts of ***,***,*** and *** showed anti-settlement activities against the barnacle Balanus albicostatus,with EC values respectively of 0.85,10.13,37.03,and 50.67 μg/*** antifouling compound,identified as oleanolic acid,was isolated from the two most active extracts(the *** extract and the *** extract) via bioassay-guided fractionation.A potential multiple defense strategy of *** against barnacle fouling,including low surface wettability,anti-barnacle settlement metabolite of oleanolic acid,and post-settlement detachment of barnacles from its flexible leaves,is proposed in this study.

关键词： Mangrove Barnacle fouling Antifouling defense Sonneratia apetala Surface wettability oleanolic acid

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齐墩果酸抗HSV-1活性及其机制研究

齐墩果酸抗HSV-1活性及其机制研究

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作者：贾娇艳暨南大学

学位级别：硕士

目的:安息香中分离提纯的齐墩果酸(oleanolic acid)化合物体内外抗HSV-1活性,以及抗病毒机制的探究,为开发新型抗HSV-1药物奠定理论基础。方法:通过CCK8实验法在不同细胞上检测了oleanolic acid毒性,利用空斑减数实验、病毒基因组DNA拷... 详细信息

目的:安息香中分离提纯的齐墩果酸(oleanolic acid)化合物体内外抗HSV-1活性,以及抗病毒机制的探究,为开发新型抗HSV-1药物奠定理论基础。方法:通过CCK8实验法在不同细胞上检测了oleanolic acid毒性,利用空斑减数实验、病毒基因组DNA拷贝数、病毒滴度等方法检测了oleanolic acid抗HSV-1活性,通过不同时间点加药探究了oleanolic acid作用阶段,在确定oleanolic acid能够影响解旋酶-引发酶复合物的基础上构建了质粒,并通过si RNA干扰以及过表达确定了oleanolic acid的潜在靶点,最后通过小鼠皮肤带状疱疹模型探究了oleanolic acid的体内抗HSV-1活性。结果:oleanolic acid对Vero细胞和Ha Ca T细胞的毒性不大,IC值分别为39.05μM和37.06μM,空斑减数实验以及病毒滴度和WB结果表明oleanolic acid在不同的细胞上均有抗HSV-1活性,并且oleanolic acid对ACV耐药株也有很好的抗病毒活性,另外机制研究发现oleanolic acid在立即早期阶段发挥更好的抗HSV-1活性,进一步的研究发现oleanolic acid能够显著性的下调解旋酶-引发酶复合物m RNA的表达水平,并且发现UL8是oleanolic acid的潜在靶点,最后体内抗HSV-1实验表明oleanolic acid能够显著性改善小鼠感染HSV-1引起的带状皮肤疱疹,说明oleanolic acid在体内和体外均有抗HSV-1活性。结论:oleanolic acid对于HSV-1正常株和ACV耐药株都有抗病毒活性,并且oleanolic acid在体内也有良好的抗HSV-1活性,机制研究表明oleanolic acid通过UL8发挥抗病毒活性,UL8是oleanolic acid的潜在靶点。

关键词： HSV-1 oleanolic acid UL8 带状皮肤疱疹体内体外抗病毒活性

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A CYP716A enzyme function of oleanane oxidase in biosynthesis of triterpenoid in Polygala tenuifolia willd

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中国药理学与毒理学杂志 2019年第10期 818-818页

作者： ZHANG Fu-sheng MEI Yue-ju WANG Qian-yu PU Ya-jie DU Chen-hui QIN Xue-mei TIAN Hong-ling LIAN Yun-lan LI Min-sheng CHEN Yu MA Cun-gen Modern Research Center for Traditional Chinese Medicine Shanxi University College of Chemistry and Chemical Engineering Shanxi University Shanxi University of Chinese medicine Research Institute of Economics Crop Shanxi Academy of Agriculture Science Shanxi Institute for Food and Drug Control

OBJECTIVE To study the CYP716 A enzyme function of oleanane oxidase in the biosynthesis of triterpenoid in Polygala tenuifolia Willd. METHODS Our research use phylogenetic analysis of different cytochrome P450 monooxygenases（P450 s） related to the biosynthesis of polygala saponin aglycone, we found that CYP716 A249（Gen Bank: KY385302.1） is possibly to play the role of oleanane oxidase, and catalyze theβ-amyrin to formed oleanolic acid, which is the skeleton of polygala saponin aglycone. Therefore, the expression plasmid p RS425-TYS1 p-Ggb AS-TYS1 t was constructed for introducing the b AS into Saccharomyces cerevisiae W303 a to obtain strain Sb1. Then, the plasmid p RS304-ADH1 p-Pt OAS-ADHIt-ALAIp-CPR-ALA1 t was transferred into Sb1 to construct strain Sb1 Pt;, in order to confirm the function of CYP716 A249. Finally, the function of CYP716 A249 enzyme was identified in S. cerevisiae through metabolite detection by ultra performance liquid chromatography-mass spectrometry（UPLC-MS）, gas chromatography-mass spectrometry（GC-MS） and nuclear magnetic resonance（NMR）. CONCLUSION We found that CYP716 A249 is likely to play the role of β-amyrin synthase by phylogenetic analysis, catalyzed the β-amyrin to form oleanolic acid through phylogenetic analysis.

关键词： Polygala tenuifolia CYP716A249 gene expression oleanolic acid biocatalysis

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