Facile preparation and characterization of novel oleanane-type triterpene functionalized β-cyclodextrin conjugates |
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作者姓名: | Pingxuan Jiao Shouxin Wang Shuobin Liang Man Li Qianqian Gao Dezhong Ji Yingying Chen Haiwei Li Fuxiang Ran Yongmin Zhang Lihe Zhang Demin Zhou Sulong Xiao |
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作者单位: | State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China;
; State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China;
; School of Pharmacy, Jining Medical University, Rizhao 276826, China;
; Sorbonne Université, Institut Parisien de Chimie Moléculaire, CNRS UMR 8232, 4 place Jussieu, 75005 Paris, France |
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基金项目: | supported by the National Natural Science Foundation of China (Nos. 81573269, 21572015, 21877007, 91753202 and 21702007);and the open funding of the State Key Laboratory of Phytochemistry and Plant Resources in West China |
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摘 要: | Oleanolic acid(OA) and echinocystic acid(EA), two naturally occurring pentacyclic oleanane triterpenes,are gaining increasing attention due to their promising pharmacological activities. Conjugation with amphiphilic α(β)-cyclodextrin(CD) via "click chemistry" can improve their solubility and anti-HCV entry potency. In the present work,four water-soluble β-CD-pentacyclic triterpene conjugates were designed and synthesized, in which OA and EA was coupled to one of the primary hydroxyl groups of β-CD via ester and amide bonds. The structures of the conjugates were unambiguously determined by ~1H NMR, 13C NMR and HRMS or MALDI-TOF-MS. All the conjugates showed lower hydrophobicity(AlogP) than their parent compounds and no significant cytotoxicity was found to HL-60, A549, Hela and Bel-7402 cells at concentrations up to 10 μmol/L. Further anti-HCV entry activity and mechanism studies are under way in our laboratory.
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关 键 词: | Β-CYCLODEXTRIN DIBAL-H Oleanolic ACID Echinocystic ACID Synthesis |
收稿时间: | 1 June 2018 |
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