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

Steroids

Volumn 78, Issue 2, 2013, Pages 203-209

  Wang, Peng ^a,b   Bi, Xiu Li ^c   Xu, Jing ^a   Yuan, Hao Nan ^a,b   Piao, Hu Ri ^b   Zhao, Yu Qing ^a  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^b YANBIAN UNIVERSITY   (China)

^c LIAONING UNIVERSITY   (China)

Author keywords

25 OH PPD derivatives; Amino acids; Anti tumor activity; MTT

Indexed keywords

12BETA O (BOC ALANYL) DAMMARANE 3BETA 20,25 TRIOL; 12BETA O (BOC GLYCYL) DAMMARANE 3BETA 20, 25 TRIOL; 12BETA O (BOC METHINYL) DAMMARANE 3BETA 20, 25 TRIOL; 12BETA O (BOC PROLYL) DAMMARANE 3BETA 20,25 TRIOL; 12BETA O (BOC VALYL) DAMMARANE 3BETA 20,25 TRIOL; 25 HYDROXYPROTOPANAXADIOL DERIVATIVE; 3BETA O (ALANYL) DAMMARANE 12BETA 20, 25 TRIOL; 3BETA O (BOC ALANYL) DAMMARANE 12BETA 20,25 TRIOL; 3BETA O (BOC ARGINYL) DAMMARANE 12BETA 20, 25 TRIOL; 3BETA O (BOC GLYCYL) DAMMARANE 12BETA 20,25 TRIOL; 3BETA O (BOC LYSYL) DAMMARANE 12BETA 20, 25 TRIOL; 3BETA O (BOC METHINYL) DAMMARANE 12BETA 20, 25 TRIOL; 3BETA O (BOC PHENYLALANYL) DAMMARANE 12BETA 20, 25 TRIOL; 3BETA O (BOC PROLYL) DAMMARANE 12BETA 20, 25 TRIOL; 3BETA O (BOC VALYL) DAMMARANE 12BETA 20, 25 TRIOL; 3BETA O (GLYCYL) DAMMARANE 20, 25 TRIOL; 3BETA O (METHINYL) DAMMARANE 12BETA 20, 25 TRIOL; 3BETA O (PHENYLALANYL) DAMMARANE 12BETA 20, 25 TRIOL; 3BETA O (PROLYL) DAMMARANE 12BETA 20, 25 TRIOL; 3BETA O (VALYL) DAMMARANE 12BETA 20, 25 TRIOL; AMINO ACID; PROTOPANAXADIOL; UNCLASSIFIED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYTOTOXICITY; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IN VITRO STUDY; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; TUMOR CELL;

AMINO ACIDS; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; DRUG SCREENING ASSAYS, ANTITUMOR; GINSENOSIDES; HUMANS;

EID: 84871449363     PISSN: 0039128X     EISSN: 18785867     Source Type: Journal    
DOI: 10.1016/j.steroids.2012.09.012     Document Type: Article

References (21)

1. A.S. Attele, J.A. Wu, and C.S. Yuan Ginseng pharmacology: multiple constituents and multiple actions Biochem Pharmacol 58 1999 1685 1693
2. M. Mochizuki, C.Y. Yoo, K. Mtsuzawa, K. Sato, I. Saiki, and S. Tonooda Inhibitory effect of tumor metastasis in mice by saponins, ginsenoside-Rb2, 20(R)- and 20(S)-ginsenoside-Rg3, of red ginseng Biol Pharm Bull 18 1995 1197 1202
3. J.Y. Lee, J.W. Shin, K.S. Chun, K.K. Park, W.Y. Chung, and Y.J. Bang Antitumor promotional effects of a novel intestinal bacterial metabolite (IH-901) derived from the protopanaxadiol-type ginsenosides in mouse skin Carcinogenesis 26 2005 359 367
4. G. Li, Z. Wang, Y. Sun, K. Liu, and Z. Wang Ginsenoside 20(S)-protopanaxadiol inhibits the proliferation and invasion of human fibrosarcoma HT1080 cells Basic Clin Pharmacol Toxicol 98 2006 588 592
5. W. Wang, E.R. Rayburn, and Y.Q. Zhao Novel ginsenosides 25-OH-PPD and 25-OCH3-PPD as experimental therapy for pancreatic cancer: anticancer activity and mechanisms of action Cancer Lett 278 2009 241 248
6. 3 in human colon cancer cell lines Biosci Biotechnol Biochem 73 2009 811 816
7. W. Wang, E.R. Rayburn, and Y.Q. Zhao In vitro anti-cancer activity and structure-activity relationships of natural products isolated from fruits of Panax ginseng Cancer Chemother Pharmacol 59 2007 589 593
8. X.R. Zhang, D. Zhang, J.H. Xu, J.K. Gu, and Y.Q. Zhao Determination of 25-OH-PPD in rat plasma by high-performance liquid chromatography-mass spectrometry and its application in rat pharmacokinetic studies J Chromatogr B Anal Technol Biomed Life Sci 858 2007 65 70
9. M. Hao, W. Wang, Y.Q. Zhao, R.W. Zhang, and H. Wang Pharmacokinetics and tissue distribution of 25-hydroxyprotopanaxadiol, an anti-cancer compound isolated from Panax ginseng, in athymic mice bearing xenografts of human pancreatic tumors Eur J Drug Metab Pharmacokinet 35 2011 109 113
10. W. Wang, E.R. Rayburn, M. Hao, Y.Q. Zhao, D.L. Hill, and R.W. Zhang Experimental therapy of prostate cancer with novel natural product anti-cancer ginsenosides Prostata 68 2008 809 819
11. J.M. Zhao, N. Li, H. Zhang, C. Wu, H.R. Piao, and Y.Q. Zhao Novel dammarane-type sapogenins from Panax ginseng berry and their biological activities J Bioorg Med Chem Lett 21 2011 1027 1031
12. 1 from Panax ginseng Pharm Pharmacol 50 1998 1155 1160
13. C. Wakabayashi, K. Murakami, H. Hasegawa, J. Murata, and I. Saiki An intestinal bacterial metabolite of ginseng protopanaxadiol saponins has the ability to induce apoptosis in tumor cells Biochem Biophys Res Commun 246 1998 725 730
14. 3-PPD], a novel natural product from Panax notoginseng Med Chem 3 2007 51 60
15. W. Wang, H. Wang, E.R. Rayburn, Y.Q. Zhao, D.L. Hill, and R. Zhang 20(S)-25-Methoxyl-dammarane-3β, 12β, 20-triol, a novel natural product for prostate cancer therapy: activity in vitro and in vivo and mechanisms: of action Br J Cancer 26 2008 792 802
16. X.K. Liu, B.J. Ye, Y. Wu, Z.H. Lin, Y.Q. Zhao, and H.R. Piao Synthesis and anti-tumor evaluation of panaxadiol derivatives Eur J Med Chem 46 2011 1997 2002
17. Stefan Schwarz, and René Csuk Synthesis and antitumour activity of glycyrrhetinic acid derivatives Bioorg Med Chem 18 2010 7458 7474
18. M.J. Zhang, X.H. Yuan, L. Ma, J.Y. Zhao, and L.X. Gao Selective deprotection of N-Boc catalyzed by silica gel Chem J Chin Univ 28 2007 2330 2332
19. Malgorzata Drag-Zalesinska, Julita Kulbacka, Jolanta Saczko, Teresa Wysocka, Maciej Zabel, and Pawel Surowiak Esters of betulin and betulinic acid with amino acids have improved water solubility and are selectively cytotoxic toward cancer cells Bioorg Med Chem Lett 19 2009 4814 4817
20. K. Papi Reddy, A.B. Singh, A. Puri, A.K. Srivastava, and T. Narender Synthesis of novel triterpenoid (lupeol) derivatives and their in vivo antihyperglycemic and antidyslipidemic activity Bioorg Med Chem Lett 19 2009 4463 4466
21. Alan R. Katritzky, and Parul Angrish Efficient microwave assisted access to chiral O-(α-protected-aminoacyl) steroids Steroids 71 2006 660 669