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
[41]   Characterization of the changes in eicosanoid profiles of activated macrophages treated with 20(S)-ginsenoside Rg3 [J].
Lee, Jae Won ;
Choi, Yu Ri ;
Mok, Hyuck Jun ;
Seong, Hyun-A ;
Lee, Dae Young ;
Kim, Geum-Soog ;
Yoon, Ji Hye ;
Kim, Kwang Pyo ;
Kim, Hyung Don .
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 2017, 1065 :14-19
[42]   Synergistic effects of ginsenoside Rg3 and cyclophosphamine on tumor growth and angiogenesis in lung cancer [J].
Li Hang ;
Wang Jun ;
Guan Yanfeng ;
Yang Wenjun ;
Aiying ;
Suo Aiying ;
Chu Meihua ;
Wang Chenyu ;
Jiang Jing ;
Zhai Shengping ;
Mao Qishan .
AFRICAN JOURNAL OF BIOTECHNOLOGY, 2011, 10 (49) :10040-10044
[43]   Ginsenoside 20(R)-Rg3 enhances natural killer cell activity by increasing activating receptor expression through the MAPK/ERK signaling pathway [J].
Lee, Yunhee ;
Park, Arum ;
Park, Young-Jun ;
Jung, Haiyoung ;
Kim, Tae-Don ;
Noh, Ji-Yoon ;
Choi, Inpyo ;
Lee, Seungjin ;
Yoon, Suk Ran .
INTERNATIONAL IMMUNOPHARMACOLOGY, 2022, 107
[44]   Ginsenoside Rg3 attenuates cell migration via inhibition of aquaporin 1 expression in PC-3M prostate cancer cells [J].
Pan, Xue-Yang ;
Guo, Hao ;
Han, Jing ;
Hao, Feng ;
An, Yu ;
Xu, Yan ;
Xiaokaiti, Yilixiati ;
Pan, Yan ;
Li, Xue-Jun .
EUROPEAN JOURNAL OF PHARMACOLOGY, 2012, 683 (1-3) :27-34
[45]   Antioxidative, anti-inflammatory, and matrix metalloproteinase inhibitory activities of 20(S)-ginsenoside Rg3 in cultured mammalian cell lines [J].
Yu-Mi Shin ;
Hyun-Joo Jung ;
Woo-Yong Choi ;
Chang-Jin Lim .
Molecular Biology Reports, 2013, 40 :269-279
[46]   Antioxidative, anti-inflammatory, and matrix metalloproteinase inhibitory activities of 20(S)-ginsenoside Rg3 in cultured mammalian cell lines [J].
Shin, Yu-Mi ;
Jung, Hyun-Joo ;
Choi, Woo-Yong ;
Lim, Chang-Jin .
MOLECULAR BIOLOGY REPORTS, 2013, 40 (01) :269-279
[47]   Engineering UDP-Glycosyltransferase UGTPg29 for the Efficient Synthesis of Ginsenoside Rg3 from Protopanaxadiol [J].
He, Huichang ;
Chen, Jiajie ;
Xie, Jiangtao ;
Ding, Jiajie ;
Pan, Huayi ;
Li, Yan ;
Jia, Honghua .
APPLIED BIOCHEMISTRY AND BIOTECHNOLOGY, 2025, 197 (01) :355-369
[48]   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].
Hao Wu ;
Guoli Wei ;
Lixia Luo ;
Lingchang Li ;
Yibo Gao ;
Xiaobin Tan ;
Sen Wang ;
Haoxiao Chang ;
Yuxi Liu ;
Yingjie Wei ;
Jie Song ;
Zhenhai Zhang ;
Jiege Huo .
Biomaterials Research, 26
[49]   Toxicity of a novel anti-tumor agent 20(S)-ginsenoside Rg3: A 26-week intramuscular repeated administration study in Beagle dogs [J].
Liu, J. -P. ;
Lu, D. ;
Nicholson, Richard C. ;
Li, P. -Y. ;
Wang, F. .
FOOD AND CHEMICAL TOXICOLOGY, 2011, 49 (08) :1718-1727
[50]   A 26-week 20(S)-ginsenoside Rg3 oral toxicity study in Beagle dogs [J].
Gao, Yonglin ;
Wang, Guangfei ;
Wang, Tong ;
Li, Guisheng ;
Lin, Jian ;
Sun, Liqin ;
Wu, Xuran ;
Sun, Xilin ;
Wang, Hongbo ;
Li, Chunmei ;
Tian, Jingwei ;
Zhu, Jing ;
Wang, Kezhou ;
Cho, Susan .
REGULATORY TOXICOLOGY AND PHARMACOLOGY, 2020, 110