Isolation, Synthesis and Structures of Ginsenoside Derivatives and Their Anti-Tumor Bioactivity

被引:20
作者
Han, Mei [2 ]
Hou, Jin-Gang [2 ]
Dong, Cheng-Ming [1 ]
Li, Wei [2 ,3 ]
Yu, Hao-Lun [2 ]
Zheng, Yi-Nan [2 ]
Chen, Li [3 ]
机构
[1] Henan Coll Tradit Chinese Med, Dept Pharmaceut Sci, Zhengzhou 450008, Peoples R China
[2] Jilin Agr Univ, Coll Chinese Med Mat, Changchun 130118, Peoples R China
[3] Jilin Univ, Norman Bethune Coll Med, Changchun 130000, Peoples R China
来源
MOLECULES | 2010年 / 15卷 / 01期
关键词
isolation; synthesis; ginsenoside-ORh1; PROLIFERATION; ACTIVATION; APOPTOSIS; LEUKEMIA;
D O I
10.3390/molecules15010399
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
Protopanaxatriol saponins obtained with AB-8 macroporous resin mainly consisted of ginsenosides Rg(1) and Re. A novel mono-ester of ginsenoside-Rh-1 (ginsenoside-ORh1) was synthesized through further enzymatic hydrolysis and octanoyl chloride modifications. A 53% yield was obtained by a facile synthetic method. The structures were identified on the basis of 1D-NMR and 2D-NMR, as well as ESI-TOF-MS mass spectroscopic analyses. The isolated and synthetic compounds were applied in an anti-tumor bioassay, in which ginsenoside ORh1 showed moderate effects on Murine H22 Hepatoma Cells.
引用
收藏
页码:399 / 406
页数:8
相关论文
共 19 条
[1]   Ginseng pharmacology - Multiple constituents and multiple actions [J].
Attele, AS ;
Wu, JA ;
Yuan, CS .
BIOCHEMICAL PHARMACOLOGY, 1999, 58 (11) :1685-1693
[2]   Bariatric surgery - Surgery for weight control in patients with morbid obesity [J].
Balsiger, BM ;
Murr, MM ;
Poggio, JL ;
Sarr, MG .
MEDICAL CLINICS OF NORTH AMERICA, 2000, 84 (02) :477-+
[3]  
Hasegawa H, 2000, BIOL PHARM BULL, V23, P298, DOI 10.1248/bpb.23.298
[4]   Free radical scavenging capacity as related to antioxidant activity and ginsenoside composition of Asian and North American ginseng extracts [J].
Hu, C ;
Kitts, DD .
JOURNAL OF THE AMERICAN OIL CHEMISTS SOCIETY, 2001, 78 (03) :249-255
[5]   Ginseng intestinal metabolite-I (GIM-I) reduces doxorubicin toxicity in the mouse testis [J].
Kang, JK ;
Lee, YJ ;
No, KO ;
Jung, EY ;
Sung, JH ;
Kim, YB ;
Nam, SY .
REPRODUCTIVE TOXICOLOGY, 2002, 16 (03) :291-298
[6]   Increase in the free radical scavenging activities of American ginseng by heat processing and its safety evaluation [J].
Kang, Ki Sung ;
Yamabe, Noriko ;
Kim, Hyun Young ;
Okamoto, Takuya ;
Sei, Yasuo ;
Yokozawa, Takako .
JOURNAL OF ETHNOPHARMACOLOGY, 2007, 113 (02) :225-232
[7]   Weight gain reduction in mice fed Panax ginseng saponin, a pancreatic lipase inhibitor [J].
Karu, Naama ;
Reifen, Ram ;
Kerem, Zohar .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2007, 55 (08) :2824-2828
[8]   Inhibitory effects of the ginsenoside R93 on phorbol ester-induced cyclooxygenase-2 expression, NF-κB activation and tumor promotion [J].
Keum, YS ;
Han, SS ;
Chun, KS ;
Park, KK ;
Park, JH ;
Lee, SK ;
Surh, YJ .
MUTATION RESEARCH-FUNDAMENTAL AND MOLECULAR MECHANISMS OF MUTAGENESIS, 2003, 523 :75-85
[9]   Reversal of P-glycoprotein-mediated multidrug resistance by ginsenoside Rg3 [J].
Kim, SW ;
Kwon, H ;
Chi, DW ;
Shim, JH ;
Park, JD ;
Lee, YH ;
Pyo, S ;
Rhee, DK .
BIOCHEMICAL PHARMACOLOGY, 2003, 65 (01) :75-82
[10]   In vitro induction of differentiation by ginsenosides in F9 teratocarcinoma cells [J].
Lee, YN ;
Lee, HY ;
Chung, HY ;
Kim, SI ;
Lee, SK ;
Park, BC ;
Kim, KW .
EUROPEAN JOURNAL OF CANCER, 1996, 32A (08) :1420-1428