Regioselective synthesis and structures of anti-cancer 20(R)-ginsenoside Rg3 derivatives

被引:5
作者
Fan, Hong-Yu [1 ,2 ]
机构
[1] Dalian Fusheng Nat Pharmaceut Dev Co Ltd, Dalian 116600, Peoples R China
[2] Jilin Univ, Dept Pharmacol, Changchun, Jilin, Peoples R China
关键词
Anti-cancer; 20(R)-ginsenoside Rg3; regioselective synthesis; INTESTINAL BACTERIA; GINSENOSIDE RG3; LIQUID-CHROMATOGRAPHY; SAPONINS; METASTASIS; INHIBITION; CANCER; ESTERS; ESTERIFICATION; TRANSFORMATION;
D O I
10.1080/14786419.2019.1569007
中图分类号
O69 [应用化学];
学科分类号
081704 ;
摘要
Regioselective synthesis of three novel palmitates of 20(R)-ginsenoside Rg(3) was accomplished via a facile strategy, along with complete assignment of their H-1 and C-13 NMR resonances by 1D and 2D NMR (H-1-H-1 COSY, DEPT 135, HSQC, HMBC, and NOESY) techniques. The derivatives were tested for in vitro anti-proliferative activities against pancreatic cancer PANC-1 cells. Compounds 2, 3, and 4 exhibited more potent activity than did 20(R)-ginsenoside Rg(3).
引用
收藏
页码:1962 / 1970
页数:9
相关论文
共 50 条
[21]   Ginsenoside Rg3 Inhibition of Thyroid Cancer Metastasis Is Associated with Alternation of Actin Skeleton [J].
Wu, Wenshuang ;
Zhou, Qian ;
Zhao, Wanjun ;
Gong, Yanping ;
Su, Anping ;
Liu, Feng ;
Liu, Yang ;
Li, Zhihui ;
Zhu, Jingqiang .
JOURNAL OF MEDICINAL FOOD, 2018, 21 (09) :849-857
[22]   Effects of ginsenoside Rg3 on epigenetic modification in ovarian cancer cells [J].
Zhao, Lingqin ;
Shou, Huafeng ;
Chen, Lu ;
Gao, Wen ;
Fang, Chenyan ;
Zhang, Ping .
ONCOLOGY REPORTS, 2019, 41 (06) :3209-3218
[23]   Particulate matter-induced lung cancer metastasis is inhibited by ginsenoside Rg3 [J].
Lee, Youn Jung ;
Park, Seung-Ho ;
Oh, Bumjo ;
Yoon, Sung-Jin ;
Lee, Seon-Jin ;
Choi, Song ;
Kim, Min Jeong ;
Kim, Jinhee ;
Cho, Young-Lai ;
Kim, Wantae ;
Ku, Bon Jeong ;
Park, Young-Jun .
JOURNAL OF ENVIRONMENTAL SCIENCES, 2025, 158 :60-71
[24]   Ginsenoside Rg3 inhibits tumor growth in gastric cancer in vitro [J].
Ye, Hongli ;
Xiao, Feng ;
Yu, Haihong ;
Liu, Bin .
JOURNAL OF GASTROENTEROLOGY AND HEPATOLOGY, 2013, 28 :298-298
[25]   Enhanced oral bioavailability and anti-tumour effect of paclitaxel by 20(s)-ginsenoside Rg3 in vivo [J].
Yang, Lei-Qiong ;
Wang, Bin ;
Gan, Hui ;
Fu, Shou-Ting ;
Zhu, Xiao-Xia ;
Wu, Zhuo-Na ;
Zhan, Da-Wei ;
Gu, Ruo-Lan ;
Dou, Gui-Fang ;
Meng, Zhi-Yun .
BIOPHARMACEUTICS & DRUG DISPOSITION, 2012, 33 (08) :425-436
[26]   Anchoring 20(R)-Ginsenoside Rg3 onto Cellulose Nanocrystals To Increase the Hydroxyl Radical Scavenging Activity [J].
Tang, Chunxia ;
Wang, Yulong ;
Long, Yunduo ;
An, Xingye ;
Shen, Jing ;
Ni, Yonghao .
ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2017, 5 (09) :7507-7513
[27]   Conversion of Ginsenoside Rb1 into Six Types of Highly Bioactive Ginsenoside Rg3 and Its Derivatives by FeCl3 Catalysis [J].
Yu, Hongshan ;
Wang, Yu ;
Liu, Chunying ;
Yang, Jiamei ;
Xu, Longquan ;
Li, Guanheng ;
Song, Jianguo ;
Jin, Fengxie .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2018, 66 (09) :901-906
[28]   Ginsenoside Rg3 nanoparticles with permeation enhancing based chitosan derivatives were encapsulated with doxorubicin by thermosensitive hydrogel and anti-cancer evaluation of peritumoral hydrogel injection combined with PD-L1 antibody [J].
Wu, Hao ;
Wei, Guoli ;
Luo, Lixia ;
Li, Lingchang ;
Gao, Yibo ;
Tan, Xiaobin ;
Wang, Sen ;
Chang, Haoxiao ;
Liu, Yuxi ;
Wei, Yingjie ;
Song, Jie ;
Zhang, Zhenhai ;
Huo, Jiege .
BIOMATERIALS RESEARCH, 2022, 26 (01)
[29]   Evaluation of Antifatigue Effects of 20(S)-Ginsenoside Rg3 in Forced Swimming Mice [J].
Li Shanshan ;
Chen Zichao .
INDIAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2018, 80 (03) :510-515
[30]   20(S)-Ginsenoside Rg3 Promotes HeLa Cell Apoptosis by Regulating Autophagy [J].
Bian, Shuai ;
Zhao, Yue ;
Li, Fangyu ;
Lu, Shuyan ;
Wang, Siming ;
Bai, Xueyuan ;
Liu, Meichen ;
Zhao, Daqing ;
Wang, Jiawen ;
Guo, Dean .
MOLECULES, 2019, 24 (20)