Cytotoxic oleane-type triterpene saponins from Glochidion eriocarpum

Archives of Pharmacal Research

Volumn 35, Issue 1, 2012, Pages 19-26

  Nhiem, Nguyen Xuan ^a,b   Thu, Vu Kim ^b   Van Kiem, Phan ^b   Van Minh, Chau ^b   Tai, Bui Huu ^a,b   Quang, Tran Hong ^a,b   Cuong, Nguyen Xuan ^b   Yen, Pham Hai ^b   Boo, Hye Jin ^c   Kang, Jung Il ^c   Kang, Hee Kyoung ^c   Kim, Young Ho ^a  

^a Chungnam National University   (South Korea)

^b GRADUATE UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Viet Nam)

^c Jeju National University School of Medicine   (South Korea)

Author keywords

Apoptosis; Cytotoxic activity; Euphorbiaceae; Glochidion eriocarpum; Glochierioside; Triterpenoid saponin

Indexed keywords

MITOGEN ACTIVATED PROTEIN KINASE; PROCASPASE 3; PROTEIN BAX; PROTEIN BCL 2; SAPONIN; SYNAPTOPHYSIN; TRITERPENE DERIVATIVE;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CANCER CELL CULTURE; CELL ASSAY; CELL VIABILITY; CHROMATIN CONDENSATION; CONTROLLED STUDY; CYTOTOXICITY; DRUG INHIBITION; DRUG POTENCY; DRUG STRUCTURE; GLOCHIDION ERIOCARPUM; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IC 50; MEDICINAL PLANT; PROTEIN EXPRESSION;

APOPTOSIS; CYTOTOXINS; EUPHORBIACEAE; HCT116 CELLS; HL-60 CELLS; HUMANS; PLANT COMPONENTS, AERIAL; PLANT EXTRACTS; SAPONINS; TRITERPENES;

EID: 84863128309     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-012-0102-2     Document Type: Article

References (35)

1. K. H. Altmann J. Gertsch 2007 Anticancer drugs from naturenatural products as a unique source of new microtubulestabilizing agents Nat. Prod. Rep. 24 327 357 17390000 10.1039/b515619j 1:CAS:528:DC%2BD2sXlt1Oqsro%3D (Pubitemid 46504987)
2. American Cancer Society. Cancer Facts & Figures 2010. Atlanta, p. 2, (2010).
3. R. Bassi R. Heads M. S. Marber J. E. Clark 2008 Targeting p38-MAPK in the ischaemic heart: kill or cure? Curr. Opin. Pharmacol. 8 141 146 18289939 10.1016/j.coph.2008.01.002 1:CAS:528:DC%2BD1cXjtlGksL0%3D
4. Bich, D. H., Chung, D. Q., Chuong, B. X., Dong, N. T., Dam, D. T., Hien, P. V., Lo, V. N., Mai, P. D., Man, P. K., Nhu, D. T., Tap, N., and Toan, T., The Medicinal Plants and Animals in Vietnam. Hanoi Science and Technology Publishing House, Hanoi, Vol. 1, p. 224, (2004).
5. J. Carmichael W. G. DeGraff A. F. Gazdar J. D. Minna J. B. Mitchell 1987 Evaluation of a tetrazolium-based semiautomated colorimetric assay: assessment of radiosensitivity Cancer Res. 47 943 946 3802101 1:CAS:528:DyaL2sXhvFWrsLo%3D (Pubitemid 17027906)
6. P. K. Chan 2007 Acylation with diangeloyl groups at C21-22 positions in triterpenoid saponins is essential for cytotoxicity towards tumor cells Biochem. Pharmacol. 73 341 350 17092489 10.1016/j.bcp.2006.10.007 1:CAS:528: DC%2BD2sXht1Smsg%3D%3D (Pubitemid 44958367)
7. Cheung, E. C. and Slack, R. S., Emerging role for ERK as a key regulator of neuronal apoptosis. Sci STKE 2004, 45 (2004).
8. G. M. Cragg D. J. Newman 2005 Plants as a source of anticancer agents J. Ethnopharmacol. 100 72 79 16009521 10.1016/j.jep.2005.05.011 1:CAS:528:DC%2BD2MXmvVKnsLY%3D (Pubitemid 41073525)
9. S. Elmore 2007 Apoptosis: a review of programmed cell death Toxicol. Pathol. 35 495 516 17562483 10.1080/01926230701320337 1:CAS:528: DC%2BD2sXmtlWmtb4%3D (Pubitemid 46911891)
10. J. Fotie D. S. Bohle M. L. Leimanis E. Georges G. Rukunga A. E. Nkengfack 2005 Lupeol long-chain fatty acid esters with antimalarial activity from Holarrhena floribunda J. Nat. Prod. 69 62 67 10.1021/np050315y
11. S. Fulda K. M. Debatin 2006 Extrinsic versus intrinsic apoptosis pathways in anticancer chemotherapy Oncogene 25 4798 4811 16892092 10.1038/sj.onc. 1209608 1:CAS:528:DC%2BD28Xnsl2hsLc%3D (Pubitemid 44187627)
12. C. Gauthier J. Legault M. Lebrun P. Dufour A. Pichette 2006 Glycosidation of lupane-type triterpenoids as potent in vitro cytotoxic agents Bioorg. Med. Chem. 14 6713 6725 16787747 10.1016/j.bmc.2006.05.075 1:CAS:528: DC%2BD28XosVOiu74%3D (Pubitemid 44233310)
13. P. M. Giang L. T. K. Nhi P. T. Son W. C. Taylor 2008 Glochidioside E, an oleanane saponin from glochidion eriocarpum J. Chem. (Vietnam) 46 784 791
14. D. Hanahan R. A. Weinberg 2000 The hallmarks of cancer Cell 100 57 70 10647931 10.1016/S0092-8674(00)81683-9 1:CAS:528:DC%2BD3cXks1CktA%3D%3D (Pubitemid 30046295)
15. W. H. Hui M. M. Li 1976 An examination of the Euphorbiaceae of Hong Kong. Part 11. Lupene triterpenoids from Glochidion eriocarpum Phytochemistry 15 561 562 10.1016/S0031-9422(00)88976-1 1:CAS:528:DyaE28XlslOltb0%3D
16. H. Inaba Y. Nagaoka Y. Kushima A. Kumagai Y. Matsumoto M. Sakaguchi K. Baba S. Uesato 2008 Comparative examination of anti-proliferative activities of (-)-epigallocatechin gallate and (-)-epigallocatechin against HCT116 colorectal carcinoma cells Biol. Pharm. Bull. 31 79 84 18175946 10.1248/bpb.31.79 1:CAS:528:DC%2BD1cXmtlalur0%3D
17. P. V. Kiem V. K. Thu P. H. Yen N. X. Nhiem N. H. Tung N. X. Cuong C. V. Minh H. T. Huong J. H. Hyun H. K. Kang Y. H. Kim 2009 New triterpenoid saponins from Glochidion eriocarpum and their cytotoxic activity Chem. Pharm. Bull. (Tokyo) 57 102 105 10.1248/cpb.57.102 1:CAS:528:DC%2BD1MXmsVGlt7s%3D
18. D. J. Newman G. M. Cragg 2007 Natural products as sources of new drugs over the last 25 years J. Nat. Prod. 70 461 477 17309302 10.1021/np068054v 1:CAS:528:DC%2BD2sXhvFKrsro%3D (Pubitemid 46595760)
19. L. K. Nhi N. V. Dau P. T. Son 1999 Contribution to study on chemical components of Glochidion eriocarpum Champ., Euphorbiaceae J. Pharm. (Vietnam) 12 9 10
20. G. Pearson F. Robinson T. Beers Gibson B. E. Xu M. Karandikar K. Berman M. H. Cobb 2001 Mitogenactivated protein (MAP) kinase pathways: regulation and physiological functions Endocr. Rev. 22 153 183 11294822 10.1210/er.22.2.153 1:CAS:528:DC%2BD3MXjsFSntL4%3D (Pubitemid 32458157)
21. P. Puapairoj W. Naengchomnong A. Kijjoa M. M. Pinto M. Pedro M. S. Nascimento A. M. Silva W. Herz 2005 Cytotoxic activity of lupane-type triterpenes from Glochidion sphaerogynum and Glochidion eriocarpum two of which induce apoptosis Planta Med. 71 208 213 15770539 10.1055/s-2005-837818 1:CAS:528:DC%2BD2MXivVCrsrw%3D (Pubitemid 40476775)
22. J. Sarek J. Klinot P. Dzubak E. Klinotova V. Noskova V. Krecek G. Korinkova J. O. Thomson A. Janost'akova S. Wang S. Parsons P. M. Fischer N. Z. Zhelev M. Hajduch 2003 New lupane derived compounds with proapoptotic activity in cancer cells: synthesis and structureactivity relationships J. Med. Chem. 46 5402 5415 14640549 10.1021/jm020854p 1:CAS:528:DC%2BD3sXovVOhtLY%3D (Pubitemid 37490373)
23. R. Seger E. G. Krebs 1995 The MAPK signaling cascade FASEB J. 9 726 735 7601337 1:CAS:528:DyaK2MXmvFCltb0%3D
24. Y. Shi M. Gaestel 2002 In the cellular garden of forking paths: how p38 MAPKs signal for downstream assistance Biol. Chem. 383 1519 1536 12452429 10.1515/BC.2002.173 1:CAS:528:DC%2BD3sXhtVyjsw%3D%3D (Pubitemid 35282972)
25. R. Siegel E. Ward O. Brawley A. J. Jemal 2011 Cancer statistics, 2011 CA Cancer J. Clin. 61 212 236 21685461 10.3322/caac.20121
26. R. Tanaka S. Matsunaga 1988 Triterpene dienols and other constituents from the bark of Phyllanthus flexuosus Phytochemistry 27 2273 2277 10.1016/0031-9422(88)80141-9 1:CAS:528:DyaL1cXlvVOhtLc%3D
27. D. Thibeault C. Gauthier J. Legault J. Bouchard P. Dufour A. Pichette 2007 Synthesis and structure-activity relationship study of cytotoxic germanicane- and lupane-type 3b-O-monodesmosidic saponins starting from betulin Bioorg. Med. Chem. 15 6144 6157 17614290 10.1016/j.bmc.2007.06.033 1:CAS:528:DC%2BD2sXot12nu7g%3D (Pubitemid 47090244)
28. V. K. Thu P. V. Kiem P. H. Yen N. X. Nhiem N. H. Tung N. X. Cuong C. V. Minh H. T. Huong T. V. Lau N. T. Thuan Y. H. Kim 2010 Triterpenoids from aerial parts of Glochidion eriocarpum Nat. Prod. Commun. 5 361 364 20420307 1:CAS:528:DC%2BC3cXjvVCrsrc%3D
29. A. Vickers 2002 Botanical medicines for the treatment of cancer: rationale, overview of current data, and methodological considerations for phase I and II trials Cancer Invest. 20 1069 1079 12449740 10.1081/CNV-120005926 (Pubitemid 35315943)
30. T. Wada J. M. Penninger 2004 Mitogen-activated protein kinases in apoptosis regulation Oncogene 23 2838 2849 15077147 10.1038/sj.onc.1207556 1:CAS:528:DC%2BD2cXivFKmsb8%3D (Pubitemid 38638846)
31. P. Wang S. Ownby Z. Zhang W. Yuan S. Li 2010 Cytotoxicity and inhibition of DNA topoisomerase I of polyhydroxylated triterpenoids and triterpenoid glycosides Bioorg. Med. Chem. Lett. 20 2790 2796 20371180 10.1016/j.bmcl.2010. 03.063 1:CAS:528:DC%2BC3cXkvFequ7o%3D
32. X. Wang J. L. Martindale N. J. Holbrook 2000 Requirement for ERK activation in cisplatin-induced apoptosis J. Biol. Chem. 275 39435 39443 10993883 10.1074/jbc.M004583200 1:CAS:528:DC%2BD3cXptFSrtr0%3D (Pubitemid 32058968)
33. Y. Yang X. Zhu Y. Chen X. Wang R. Chen 2007 p38 and JNK MAPK, but not ERK1/2 MAPK, play important role in colchicines-induced cortical neurons apoptosis Eur. J. Pharmacol. 576 26 33 17716651 10.1016/j.ejphar.2007.07.067 1:CAS:528:DC%2BD2sXhtF2ms7nJ (Pubitemid 47588251)
34. Z. Zhang S. Li 2007 Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L Phytochemistry 68 2075 2086 17599369 10.1016/j.phytochem.2007. 05.020 1:CAS:528:DC%2BD2sXotVahs74%3D (Pubitemid 47068715)
35. K. C. Zimmermann D. R. Green 2001 How cells die: apoptosis pathways J. Allergy Clin. Immunol. 108 99 103 10.1067/mai.2001.117819 (Pubitemid 32978004)