Citation: Jiao Pingxuan, Wang Shouxin, Liang Shuobin, Li Man, Gao Qianqian, Ji Dezhong, Chen Yingying, Li Haiwei, Ran Fuxiang, Zhang Yongmin, Zhang Lihe, Zhou Demin, Xiao Sulong. Facile preparation and characterization of novel oleanane-type triterpene functionalized β-cyclodextrin conjugates[J]. Chinese Chemical Letters, ;2019, 30(3): 690-693. doi: 10.1016/j.cclet.2018.10.009 shu

Facile preparation and characterization of novel oleanane-type triterpene functionalized β-cyclodextrin conjugates

Jiao Pingxuan ^a ,
Wang Shouxin ^a,c ,
Liang Shuobin ^a ,
Li Man ^a ,
Gao Qianqian ^a ,
Ji Dezhong ^a ,
Chen Yingying ^a ,
Li Haiwei ^a ,
Ran Fuxiang ^a ,
Zhang Yongmin ^d ,
Zhang Lihe ^a ,
Zhou Demin ^a,**, ,
Xiao Sulong ^a,b,*,

a.
State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Beijing 100191, China
b.
State Key Laboratory of Phytochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, China
c.
School of Pharmacy, Jining Medical University, Rizhao 276826, China
d.
Sorbonne Université, Institut Parisien de Chimie Moléculaire, CNRS UMR 8232, 4 place Jussieu, 75005 Paris, France

^**

deminzhou@bjmu.edu.cn

slxiao@bjmu.edu.cn

Received Date: 1 June 2018
Revised Date: 25 September 2018
Accepted Date: 10 October 2018
Available Online: 11 March 2018

Figures(4)

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.
- β-Cyclodextrin,
- DIBAL-H,
- Oleanolic acid,
- Echinocystic acid,
- Synthesis
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