Synthesis and anti-tumor evaluation of novel 25-hydroxyprotopanaxadiol analogs incorporating natural amino acids

被引:40
作者
Wang, Peng [1 ,2 ]
Bi, Xiu-Li [3 ]
Xu, Jing [1 ]
Yuan, Hao-Nan [1 ,2 ]
Piao, Hu-Ri [2 ]
Zhao, Yu-Qing [1 ]
机构
[1] Shenyang Pharmaceut Univ, Sch Tradit Chinese Mat Med, Shenyang 110016, Peoples R China
[2] Yanbian Univ, Coll Pharm, Minist Educ, Key Lab Nat Resources Changbai Mt & Funct Mol, Yanji 133002, Peoples R China
[3] Liaoning Univ, Sch Life Sci, Shenyang 110036, Peoples R China
基金
美国国家科学基金会;
关键词
25-OH-PPD derivatives; Amino acids; Anti-tumor activity; MTT; INTESTINAL BACTERIAL METABOLITE; PROSTATE-CANCER; PANAX-GINSENG; RAT PLASMA; IN-VITRO; PRODUCT; CELLS; GINSENOSIDES; SAPONINS; THERAPY;
D O I
10.1016/j.steroids.2012.09.012
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
070307 [化学生物学]; 071010 [生物化学与分子生物学];
摘要
In the current study, derivatives of 25-hydroxyprotopanaxadiol (25-OH-PPD) were prepared and their in vitro anti-tumor activities were tested on six different human tumor cell lines by standard MET assay. The results showed that combining an ester group combined with the presence of an amino acid moiety led to a 10-fold improved anti-tumor activity. Compound 1c exhibited the best anti-tumor activity in the in vitro assays. Compounds 2c, 3c, 4c, 5c, 6c and 8b showed better anti-tumor activities compared to the parent compound 25-OH-PPD. The current results may provide useful data for researching and developing new anti-cancer agents. (C) 2012 Elsevier Inc. All rights reserved.
引用
收藏
页码:203 / 209
页数:7
相关论文
共 21 条
[1]
Intestinal bacterial hydrolysis is required for the appearance of compound K in rat plasma after oral administration of ginsenoside Rb1 from Panax ginseng [J].
Akao, T ;
Kida, H ;
Kanaoka, M ;
Hattori, M ;
Kobashi, K .
JOURNAL OF PHARMACY AND PHARMACOLOGY, 1998, 50 (10) :1155-1160
[2]
Ginseng pharmacology - Multiple constituents and multiple actions [J].
Attele, AS ;
Wu, JA ;
Yuan, CS .
BIOCHEMICAL PHARMACOLOGY, 1999, 58 (11) :1685-1693
[3]
Esters of betulin and betulinic acid with amino acids have improved water solubility and are selectively cytotoxic toward cancer cells [J].
Drag-Zalesinska, Malgorzata ;
Kulbacka, Julita ;
Saczko, Jolanta ;
Wysocka, Teresa ;
Zabel, Maciej ;
Surowiak, Pawel ;
Drag, Marcin .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (16) :4814-4817
[4]
Pharmacokinetics and tissue distribution of 25-hydroxyprotopanaxadiol, an anti-cancer compound isolated from Panax ginseng, in athymic mice bearing xenografts of human pancreatic tumors [J].
Hao, Miao ;
Wang, Wei ;
Zhao, Yuqing ;
Zhang, Ruiwen ;
Wang, Hui .
EUROPEAN JOURNAL OF DRUG METABOLISM AND PHARMACOKINETICS, 2011, 35 (3-4) :109-113
[5]
Efficient microwave assisted access to chiral O-(α-protected-aminoacyl)steroids [J].
Katritzky, Alan R. ;
Angrish, Parul .
STEROIDS, 2006, 71 (08) :660-669
[6]
Antitumor promotional effects of a novel intestinal bacterial metabolite (IH-901) derived from the protopanaxadiol-type ginsenosides in mouse skin [J].
Lee, JY ;
Shin, JW ;
Chun, KS ;
Park, KK ;
Chung, WY ;
Bang, YJ ;
Sung, JH ;
Surh, YJ .
CARCINOGENESIS, 2005, 26 (02) :359-367
[7]
Proteomic Analysis of the Anti-Cancer Effect of 20S-Ginsenoside Rg3 in Human Colon Cancer Cell Lines [J].
Lee, Seo Youn ;
Kim, Geun Tae ;
Roh, Si Hun ;
Song, Jin-Su ;
Kim, Hie-Joon ;
Hong, Soon-Sun ;
Kwon, Sung Won ;
Park, Jeong Hill .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2009, 73 (04) :811-816
[8]
Ginsenoside 20(S)-protopanaxadiol inhibits the proliferation and invasion of human fibrosarcoma HT1080 cells [J].
Li, Gang ;
Wang, Zhenhua ;
Sun, Yaxuan ;
Liu, Ke ;
Wang, Ziren .
BASIC & CLINICAL PHARMACOLOGY & TOXICOLOGY, 2006, 98 (06) :588-592
[9]
Synthesis and anti-tumor evaluation of panaxadiol derivatives [J].
Liu, Xue-Kun ;
Ye, Bai-Jun ;
Wu, Yan ;
Lin, Zhen-Hua ;
Zhao, Yu-Qing ;
Piao, Hu-Ri .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (06) :1997-2002
[10]
MOCHIZUKI M, 1995, BIOL PHARM BULL, V18, P1197, DOI 10.1248/bpb.18.1197