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
1. [1]
  J.T. James, I.A. Dubery, Molecules 14 (2009) 3922-3941. doi: 10.3390/molecules14103922
2. [2]
  S. Alakurtti, T. Makela, S. Koskimies, J. Yli-Kauhaluoma, Eur. J. Pharm. Sci. 29 (2006) 1-13. doi: 10.1016/j.ejps.2006.04.006
3. [3]
  J. Pollier, A. Goossens, Phytochemistry 77 (2012) 10-15. doi: 10.1016/j.phytochem.2011.12.022
4. [4]
  R. Rodriguez-Rodriguez, Curr. Med. Chem. 22 (2015) 1414-1425. doi: 10.2174/0929867322666141212122921
5. [5]
  M.B. Sporn, K.T. Liby, M.M. Yore, et al., J. Nat. Prod. 74 (2011) 537-545. doi: 10.1021/np100826q
6. [6]
  (a) D.S.Hong, R.Kurzrock, J.G.Supko, etal., Clin.CancerRes.18 (2012)3396-3406;
  (b)M.K. Shanmugam, X.Y. Dai, A.P. Kumar, et al., Cancer Lett. 346 (2014) 206-216.
7. [7]
  F. Yu, Q. Wang, Z. Zhang, et al., J. Med. Chem. 56 (2013) 4300-4319. doi: 10.1021/jm301910a
8. [8]
  L.X. Liu, X.C. Wang, J. Chem. Eng. Data 52 (2007) 2527-2528. doi: 10.1021/je700312r
9. [9]
  K. Xu, F.H. Chu, G.L. Li, et al., Pharmazie 69 (2014) 483-495.
10. [10]
  (a) B. Gidwani, A. Vyas, Biomed. Res. Int. 2015 (2015) 198268;
  (b) S.V. Kurkov, T. Loftsson, Int. J. Pharm. 453 (2013) 167-180.
11. [11]
  (a) H.M. Wang, C.M. Soica, G. Wenz, Nat. Prod. Commun. 7 (2012) 289-291;
  (b) A. Hertrampf, C. Grundemann, S. Jager, et al., Planta Med 78 (2012) 881-889;
  (c) C. Soica, C. Oprean, F. Borcan, et al., Molecules 19 (2014) 4924-4940.
12. [12]
  (a) K. Udo, K. Hokonohara, K. Motoyama, et al., Int. J. Pharm. 388 (2010) 95-100;
  (b) R. Onodera, K. Motoyama, A. Okamatsu, T. Higashi, H. Arima, Sci. Rep. 3 (2013) 1103.
13. [13]
  (a) S. Xiao, Q. Wang, L. Si, et al., ChemMedChem. 9 (2014) 1060-1070;
  (b) S. Xiao, Q. Wang, L. Si, et al., Eur. J. Med. Chem. 124 (2016) 1-9.
14. [14]
  A.J. Pearce, P. Sinay, Angew. Chem. Int. Edit. 39 (2000) 3610-3612.
15. [15]
  D. Vizitiu, C.S. Walkinshaw, B.I. Gorin, G.R.J. Thatcher, J. Org. Chem. 62 (1997) 8760-8766. doi: 10.1021/jo9711549
16. [16]
  D. Martin, J. Navarro del Hierro, D. Villanueva Bermejo, et al., J. Agr. Food Chem. 64 (2016) 8828-8837. doi: 10.1021/acs.jafc.6b04313
17. [17]
  (a) Q. Shi, T.M. Kaiser, Z.W. Dentmon, et al., ACS Med. Chem. Lett. 6 (2015) 518-522;
  (b) F. Lovering, J. Bikker, C. Humblet, J. Med. Chem. 52 (2009) 6752-6756.
18. [18]
  (a) P. Dzubak, M. Hajduch, D. Vydra, et al., Nat. Prod. Rep. 23 (2006) 394-411;
  (b) K.T. Lee, J. Choi, W.T. Jung, et al., J. Agr. Food Chem. 50 (2002) 4190-4193.
19. [19]
  T. Mosmann, J. Immunol. Methods 65 (1983) 55-63. doi: 10.1016/0022-1759(83)90303-4
1. [1]
  Qinwei Lu , Jinjie Lu , Juying Lei , Xubiao Luo , Yanbo Zhou . Cyclodextrin-boosted photocatalytic oxidation for efficient bisphenol A removal. Chinese Chemical Letters, 2025, 36(3): 110017-. doi: 10.1016/j.cclet.2024.110017
2. [2]
  Yulong Shi , Fenbei Chen , Mengyuan Wu , Xin Zhang , Runze Meng , Kun Wang , Yan Wang , Yuheng Mei , Qionglu Duan , Yinghong Li , Rongmei Gao , Yuhuan Li , Hongbin Deng , Jiandong Jiang , Yanxiang Wang , Danqing Song . Chemical construction and anti-HCoV-OC43 evaluation of novel 10,12-disubstituted aloperine derivatives as dual cofactor inhibitors of TMPRSS2 and SR-B1. Chinese Chemical Letters, 2024, 35(5): 108792-. doi: 10.1016/j.cclet.2023.108792
3. [3]
  Wenyi Mei , Lijuan Xie , Xiaodong Zhang , Cunjian Shi , Fengzhi Wang , Qiqi Fu , Zhenjiang Zhao , Honglin Li , Yufang Xu , Zhuo Chen . Design, synthesis and biological evaluation of fluorescent derivatives of ursolic acid in living cells. Chinese Chemical Letters, 2024, 35(5): 108825-. doi: 10.1016/j.cclet.2023.108825
4. [4]
  Yulin Mao , Jingyu Ma , Jiecheng Ji , Yuliang Wang , Wanhua Wu , Cheng Yang . Crown aldoxime ethers: Their synthesis, structure, acid-catalyzed/photo-induced isomerization and adjustable guest binding. Chinese Chemical Letters, 2024, 35(11): 109927-. doi: 10.1016/j.cclet.2024.109927
5. [5]
  Guoping Yang , Zhoufu Lin , Xize Zhang , Jiawei Cao , Xuejiao Chen , Yufeng Liu , Xiaoling Lin , Ke Li . Assembly of Y(Ⅲ)-containing antimonotungstates induced by malic acid with catalytic activity for the synthesis of imidazoles. Chinese Chemical Letters, 2024, 35(12): 110274-. doi: 10.1016/j.cclet.2024.110274
6. [6]
  Dongdong YANG , Jianhua XUE , Yuanyu YANG , Meixia WU , Yujia BAI , Zongxuan WANG , Qi MA . Design and synthesis of two coordination polymers for the rapid detection of ciprofloxacin based on triphenylpolycarboxylic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2466-2474. doi: 10.11862/CJIC.20240266
7. [7]
  Jiajun Lu , Zhehui Liao , Tongxiang Cao , Shifa Zhu . Synergistic Brønsted/Lewis acid catalyzed atroposelective synthesis of aryl-β-naphthol. Chinese Chemical Letters, 2025, 36(1): 109842-. doi: 10.1016/j.cclet.2024.109842
8. [8]
  Jimin HOU , Mengyang LI , Chunhua GONG , Shaozhuang ZHANG , Caihong ZHAN , Hao XU , Jingli XIE . Synthesis, structures, and properties of metal-organic frameworks based on bipyridyl ligands and isophthalic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 549-560. doi: 10.11862/CJIC.20240348
9. [9]
  Kaimin WANG , Xiong GU , Na DENG , Hongmei YU , Yanqin YE , Yulu MA . Synthesis, structure, fluorescence properties, and Hirshfeld surface analysis of three Zn(Ⅱ)/Cu(Ⅱ) complexes based on 5-(dimethylamino) isophthalic acid. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1397-1408. doi: 10.11862/CJIC.20240009
10. [10]
  Jing LIANG , Qian WANG , Junfeng BAI . Synthesis and structures of cdq-topological quaternary and (4, 4, 8)-c topological quinary Zn-MOFs with both oxalic acid and triazole ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(11): 2186-2192. doi: 10.11862/CJIC.20240177
11. [11]
  Yuexiang Liu , Xiangqiao Yang , Tong Lin , Guantian Yang , Xiaoyong Xu , Bubing Zeng , Zhong Li , Weiping Zhu , Xuhong Qian . Efficient continuous synthesis of 2-[3-(trifluoromethyl)phenyl]malonic acid, a key intermediate of Triflumezopyrim, coupling with esterification-condensation-hydrolysis. Chinese Chemical Letters, 2025, 36(1): 109747-. doi: 10.1016/j.cclet.2024.109747
12. [12]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
13. [13]
  Ao Sun , Zipeng Li , Shuchun Li , Xiangbao Meng , Zhongtang Li , Zhongjun Li . Stereoselective synthesis of α-3-deoxy-D-manno-oct-2-ulosonic acid (α-Kdo) derivatives using a C3-p-tolylthio-substituted Kdo fluoride donor. Chinese Chemical Letters, 2025, 36(3): 109972-. doi: 10.1016/j.cclet.2024.109972
14. [14]
  Jing Guo , Zhi-Guo Lu , Rui-Chen Zhao , Bao-Ku Li , Xin Zhang . Nucleic acid therapy for metabolic-related diseases. Chinese Chemical Letters, 2025, 36(3): 109875-. doi: 10.1016/j.cclet.2024.109875
15. [15]
  Runze Liu , Yankai Bian , Weili Dai . Qualitative and quantitative analysis of Brønsted and Lewis acid sites in zeolites: A combined probe-assisted 1H MAS NMR and NH3-TPD investigation. Chinese Journal of Structural Chemistry, 2024, 43(4): 100250-100250. doi: 10.1016/j.cjsc.2024.100250
16. [16]
  Huipeng Zhao , Xiaoqiang Du . Polyoxometalates as the redox anolyte for efficient conversion of biomass to formic acid. Chinese Journal of Structural Chemistry, 2024, 43(2): 100246-100246. doi: 10.1016/j.cjsc.2024.100246
17. [17]
  Dan-Ying Xing , Xiao-Dan Zhao , Chuan-Shu He , Bo Lai . Kinetic study and DFT calculation on the tetracycline abatement by peracetic acid. Chinese Chemical Letters, 2024, 35(9): 109436-. doi: 10.1016/j.cclet.2023.109436
18. [18]
  Lihang Wang , Mary Li Javier , Chunshan Luo , Tingsheng Lu , Shudan Yao , Bing Qiu , Yun Wang , Yunfeng Lin . Research advances of tetrahedral framework nucleic acid-based systems in biomedicine. Chinese Chemical Letters, 2024, 35(11): 109591-. doi: 10.1016/j.cclet.2024.109591
19. [19]
  Siwei Wang , Wei-Lei Zhou , Yong Chen . Cucurbituril and cyclodextrin co-confinement-based multilevel assembly for single-molecule phosphorescence resonance energy transfer behavior. Chinese Chemical Letters, 2024, 35(12): 110261-. doi: 10.1016/j.cclet.2024.110261
20. [20]
  Hanqing Zhang , Xiaoxia Wang , Chen Chen , Xianfeng Yang , Chungli Dong , Yucheng Huang , Xiaoliang Zhao , Dongjiang Yang . Selective CO2-to-formic acid electrochemical conversion by modulating electronic environment of copper phthalocyanine with defective graphene. Chinese Journal of Structural Chemistry, 2023, 42(10): 100089-100089. doi: 10.1016/j.cjsc.2023.100089

Get Citation

PDF

XML

Metrics

PDF Downloads(2)
Abstract views(637)
HTML views(37)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142