Synthesis and cytotoxicity of oleanolic acid trisaccharide saponins

被引：12

作者：

Wang, Liming ^{[1
,2
,4
]}

Wang, Zengshang ^{[1
,3
]}

Su, Sheng ^{[1
]}

Xing, Ying ^{[3
]}

Li, Yali ^{[3
]}

Li, Ming ^{[2
]}

Liu, Jiangyun ^{[1
]}

Yang, Shilin ^{[1
]}

机构：

[1] Soochow Univ, Coll Pharmaceut Sci, Suzhou 215123, Peoples R China

[2] Ocean Univ China, Sch Med & Pharm, Key Lab Marine Drugs, Minist Educ, Qingdao 266003, Peoples R China

[3] Xinjiang Med Univ, Dept VIP Internal Med, Affiliated Hosp 1, Urumqi 830011, Peoples R China

[4] Jilich Res Ctr, Cent Inst Engn Elect & Analyt Analyt ZEA 3, Wilhelm Johnen Str, D-52425 Julich, Germany

来源：

CARBOHYDRATE RESEARCH | 2017年 / 442卷

基金：

中国国家自然科学基金;

关键词：

Triterpenoid saponin; beta-hederin; Glycosylation; Antiproliferation activity; CHINENSIS BUNGE REGEL; TRITERPENOID SAPONINS; HEDERACOLCHISIDE A(1); HEMOLYTIC-ACTIVITY; IN-VITRO; DERIVATIVES; BEARING;

D O I：

10.1016/j.carres.2017.02.010

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

An array of oleanolic acid-type saponins based on beta-hederin has been synthesized in a linear or one-pot manner. The cell viability assays indicate that synthetic saponins show antiproliferation activities in three cancer cell lines with IC50 values of 2.4-15.1 mu M and hederacolchiside A(1) being the most potent. The results demonstrate that the type of terminal monosaccharides and linkage position have apparent effects on cytotoxicities and selectivities of these saponins against cancer cell lines tested. This study is helpful for future development of more potent anticancer leads. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：9 / 16

页数：8

共 30 条

[1] In vitro activity of hederacolchisid A1 compared with other saponins from Hedera colchica against proliferation of human carcinoma and melanoma cells [J].

Barthomeuf, C ;

Debiton, E ;

Mshvildadze, V ;

Kemertelidze, E ;

Balansard, G .

PLANTA MEDICA, 2002, 68 (08) :672-675

[2] Synthesis, cytotoxicity and haemolytic activity of Pulsatilla saponin A, D derivatives [J].

Chen, Zhong ;

Duan, Huaqing ;

Wang, Minglei ;

Han, Li ;

Liu, Yanli ;

Zhu, Yongming ;

Yang, Shilin .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2015, 25 (12) :2550-2554

[3] Synthesis of β-hederin and Hederacolchiside A1:: triterpenoid saponins bearing a unique cytotoxicity-inducing disaccharide moiety [J].

Cheng, MS ;

Yan, MC ;

Liu, Y ;

Zheng, LG ;

Liu, J .

CARBOHYDRATE RESEARCH, 2006, 341 (01) :60-67

[4] Structure-activity relationships of some hederagenin diglycosides:: Haemolysis, cytotoxicity and apoptosis induction [J].

Chwalek, Martin ;

Lalun, Nathalie ;

Bobichon, Helene ;

Ple, Karen ;

Voutquenne-Nazabadioko, Laurence .

BIOCHIMICA ET BIOPHYSICA ACTA-GENERAL SUBJECTS, 2006, 1760 (09) :1418-1427

[5] New thioglycoside derivatives for use in odourless synthesis of MUXF3 N-glycan fragments related to food allergens [J].

Collot, Mayeul ;

Savreux, Julie ;

Mallet, Jean-Maurice .

TETRAHEDRON, 2008, 64 (07) :1523-1535

[6] Mannosylated saponins based on oleanolic and glycyrrhizic acids. Towards synthetic colloidal antigen delivery systems [J].

Daines, Alison M. ;

Greatrex, Ben W. ;

Hayman, Colin M. ;

Hook, Sarah M. ;

McBurney, Warren T. ;

Rades, Thomas ;

Rendle, Phillip M. ;

Sims, Ian M. .

BIOORGANIC & MEDICINAL CHEMISTRY, 2009, 17 (14) :5207-5218

[7] Highly efficient glycosylation of sapogenins [J].

Deng, SJ ;

Yu, B ;

Xie, JM ;

Hui, YZ .

JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (19) :7265-7266

[8] Synthesis and biological evaluation of Hederacolchiside A1 derivatives as anticancer agents [J].

Fang, Yuanying ;

Yang, Zunhua ;

Ouyang, Hui ;

Wang, Rikang ;

Li, Jun ;

Huang, Hesong ;

Jin, Yi ;

Feng, Yulin ;

Yang, Shilin .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2016, 26 (19) :4576-4579

[9] New triterpenoid saponins from Patrinia scabiosifolia [J].

Gao, Liang ;

Zhang, Lin ;

Wang, Li-Ming ;

Liu, Jiang-Yun ;

Cai, Pei-Lie ;

Yang, Shi-Lin .

JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2012, 14 (04) :333-341

[10] New triterpenoid saponins from Patrinia scabiosaefolia [J].

Gao, Liang ;

Zhang, Lin ;

Li, Nan ;

Liu, Jiang-Yun ;

Cai, Pei-lie ;

Yang, Shi-lin .

CARBOHYDRATE RESEARCH, 2011, 346 (18) :2881-2885

← 1 2 3 →