Inhibition of DNA topoisomerases i and II and cytotoxicity of compounds from Ulmus davidiana var. japonica

Archives of Pharmacal Research

Volumn 33, Issue 9, 2010, Pages 1307-1315

  Zheng, Ming Shan ^a,b   Lee, Yeun Kyung ^a   Li, Ying ^a   Hwangbo, Kyoung ^a   Lee, Chong Soon ^a   Kim, Jae Ryong ^c   Lee, Sunny Kyung Seon ^d   Chang, Hyun Wook ^a   Son, Jong Keun ^a  

^a Yeungnam University   (South Korea)

^b YANBIAN UNIVERSITY   (China)

^c Yeungnam University College of Medicine   (South Korea)

^d UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cytotoxicity; Topoisomerase; Ulmus davidiana var. japonica

Indexed keywords

24 ETHYLCHOLESTA 5,22 DIEN 3BETA OL PALMITIC ACID ESTER; 3 O (6 O PALMITORYL)BETA DEXTRO GLUCOPYRANOSYL STIGMASTEROL; 5 METHOXYISOLARICIRESINOL 9 O BETA DEXTRO XYLOPYRANOSIDE; AMPELOPSISIONOSIDE; ANTINEOPLASTIC AGENT; ARACHIDIC ACID; BETULIC ACID; BUTYL ALPHA DEXTRO FRUCTOFURANOSIDE; CATECHIN; CATECHIN 3 O ALPHA LEVO RHAMNOPYRANOSIDE; CATECHIN 7 O ALPHA LEVO RHAMNOPYRANOSIDE; CATECHIN 7 O BETA APIOFURANOSIDE; CATECHIN 7 O BETA DEXTRO GLUCOPYRANOSIDE; DNA TOPOISOMERASE; DNA TOPOISOMERASE (ATP HYDROLYSING); DNA TOPOISOMERASE INHIBITOR; EPIFRIEDELANOL; FRIEDELIN; ISOLARICIRESINOL 9' O BETA DEXTRO XYLOPYRANOSIDE; MASLINIC ACID; NUDIPOSIDE; OLEANOLIC ACID; PROCYANIDIN B3; ROSEOSIDE; SITOGLUSIDE; SITOSTEROL; SITOSTEROL 3 O BETA DEXTRO GLUCOSIDE; SSIORISIDE; STIGMAST 5 ENE 3BETA,4ALPHA DIOL; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTINEOPLASTIC ACTIVITY; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CELL STRAIN HT29; CONTROL GROUP; CONTROLLED STUDY; DRUG ACTIVITY; DRUG CYTOTOXICITY; DRUG INHIBITION; DRUG ISOLATION; DRUG POTENCY; DRUG STRUCTURE; ELM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HUMAN; HUMAN CELL; IC 50; MEDICINAL PLANT; NONHUMAN; PHYSICAL CHEMISTRY; PLANT ROOT; PROTON NUCLEAR MAGNETIC RESONANCE; ULMUS DAVIDIANA; ULTRAVIOLET RADIATION;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; CYCLOHEXANONES; DRUG DISCOVERY; DRUG SCREENING ASSAYS, ANTITUMOR; EICOSANOIC ACIDS; FLAVONOIDS; GLUCOSIDES; HUMANS; INHIBITORY CONCENTRATION 50; MEDICINE, KOREAN TRADITIONAL; MOLECULAR STRUCTURE; NEOPLASMS; PLANT BARK; PLANT EXTRACTS; PLANT ROOTS; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; TOPOISOMERASE I INHIBITORS; TOPOISOMERASE II INHIBITORS; TRITERPENES; ULMUS;

EID: 78449259383     PISSN: 02536269     EISSN: 19763786     Source Type: Journal    
DOI: 10.1007/s12272-010-0903-0     Document Type: Article

References (48)

1. H. Achenbach R. Waibel B. Raffelsberger A. M. Ivan 1981 Iridoid and other constituents of Canthium subcordatum Phytochemistry 20 1591 1595 1:CAS:528:DyaL38Xot1Kmsw%3D%3D 10.1016/S0031-9422(00)98538-8
2. M. C. Aguirre C. Delporte N. Backhouse S. Erazo M. E. Letelier B. K. Cassels X. Silva S. Alegria R. Negrete 2006 Topical anti-inflammatory activity of 2alpha-hydroxy pentacyclic triterpene acids from the leaves of Ugni molinae Bioorg. Med. Chem. 14 5673 5677 1:CAS:528:DC%2BD28Xmslyqs78%3D 10.1016/j.bmc.2006.04.021 16697209
3. M. S. Ali S. Mahmud S. Perveen V. U. Ahmad G. H. Rizwani 1999 Epimers from the leaves of Calophyllum inophyllum Phytochemistry 50 1385 1389 1:CAS:528:DyaK1MXjtFChurw%3D 10.1016/S0031-9422(98)00480-4
4. C. W. Chang T. S. Wu Y. S. Hsieh S. C. Kuo P. D. Chao 1999 Terpenoids of Syzygium formosanum J. Nat. Prod. 62 327 328 1:CAS:528:DyaK1MXos1yr 10.1021/np980313w 10075776
5. A. Y. Chen L. F. Liu 1994 DNA topoisomerase: essential enzymes and lethal targets Annu. Rev. Pharmacol. Toxicol. 34 191 218 1:CAS:528:DyaK2cXmt1Sks74%3D 10.1146/annurev.pa.34.040194.001203 8042851
6. I. M. Chung T. D. Khanh O. K. Lee A. Ahmad 2007 Chemical constituents from ajwain seeds (Trachyspermum ammi) and inhibitory acitivity of thymol, lupeol and fatty acids on barnyard grass and radish seeds Chem. Asian J. 19 1524 1534 1:CAS:528:DC%2BD2sXhtlKqt7w%3D
7. P. D'Arpa L. F. Liu 1989 Topoisomerase-targeting antitumor drugs Biochim. Biophys. Acta 989 163 177 2557085
8. S. De Marino N. Borbone F. Zollo A. Ianaro P. Di Meglio M. Iorizzi 2004 Megastigmane and phenolic components from Laurus nobilis L. leaves and their inhibitory effects on nitric oxide production J. Agric. Food Chem. 52 7525 7531 10.1021/jf048782t 15675799
9. L. Y. Foo J. J. Karchesy 1989 Polyphenolic glycosides from Douglas fir inner bark Phytochemistry 28 1237 1240 1:CAS:528:DyaL1MXltlSlu7o%3D 10.1016/0031-9422(89)80217-1
10. M. Fukuda K. Nishio F. Kanzawa H. Ogasawara T. Ishida H. Arioka K. Bojamowski M. Oka N. Saijo 1996 Synergism between cisplatin and topoisomerase I inhibitors, NB-506 and SN-38, in human small cell lung cancer cells Cancer Res. 56 789 793 1:CAS:528:DyaK28XhtVClsb4%3D 8631015
11. K. Hisashi O. Haruo 1989 Configurational studies on hydroxy groups at C-2, 3 and 23 or 24 of oleanene and ursene-type triterpenes by NMR spectroscopy Phytochemistry 28 1703 1710 10.1016/S0031-9422(00)97829-4
12. S. Inoshiri M. Sasaki H. Kohda H. Otsuka K. Yamasaki 1987 Aromatic glycosides from Berchemia racemosa Phytochemistry 26 2811 2814 1:CAS:528:DyaL1cXnt1Sqtg%3D%3D 10.1016/S0031-9422(00)83595-5
13. K. Ishimaru G. I. Nonaka I. Nishioka 1987 Flavan-3-ol and procyanidin glycosides from Quercus miyagii Phytochemistry 26 1167 1170 1:CAS:528: DyaL2sXksFGksb4%3D 10.1016/S0031-9422(00)82371-7
14. U. H. Jin D. Y. Lee D. S. Kim I. S. Lee C. H. Kim 2006 Induction of mitochondria-mediated apoptosis by methanol fraction of Ulmus davidiana Planch (Ulmaceae) in U87 glioblastoma cells Environ. Toxicol. Pharmacol. 22 136 141 1:CAS:528:DC%2BD28XntV2gsL0%3D 10.1016/j.etap.2006.01.005
15. U. H. Jin S. J. Suh S. D. Park K. S. Kim D. Y. Kwon C. H. Kim 2008 Inhibition of mouse osteoblast proliferation and prostaglandin E2 synthesis by Ulmus davidiana Planch (Ulmaceae) Food Chem. Toxicol. 46 2135 2142 1:CAS:528:DC%2BD1cXlvVShsL0%3D 10.1016/j.fct.2008.02.011 18378057
16. C. D. Jun H. O. Pae Y. C. Kim S. J. Jeong J. C. Yoo E. J. Lee B. M. Choi S. W. Chae R. K. Park H. T. Chung 1998 Inhibition of nitric oxide synthesis by butanol fraction of the methanol extract of Ulmus davidiana in murine macrophages J. Ethnopharmacol. 62 129 135 1:CAS:528:DyaK1cXkslyku70%3D 10.1016/S0378-8741(98)00063-4 9741885
17. S. K. Kang K. S. Kim Y. S. Byun S. J. Suh U. H. Jin K. H. Kim I. S. Lee C. H. Kim 2006 Effects of Ulmus davidiana Planch on mineralization, bone morphogenetic protein-2, alkaline phosphatase type I collagen, and collagenase-1 in bone cells In Vitro Cell. Dev. Biol. Anim. 42 225 229 10.1290/0510068.1 16948504
18. N. Kohler V. Wray P. Winterhalter 2008 Preparative isolation of procyanidins from grap seed extracts by highspeed counter-current chromatography J. Chromatogr. A 1177 114 125 1:STN:280:DC%2BD2sjlslelug%3D%3D 10.1016/j.chroma.2007.11.028 18054944
19. C. Lavaud G. Massiot J. B. Barrera C. Moretti L. Le Men-Olivier 1994 Triterpene saponins from Myrsine pellucida Phytochemistry 37 1671 1677 1:CAS:528:DyaK2MXksFKisrw%3D 10.1016/S0031-9422(00)89590-4 7766004
20. K. H. Lee J. H. Lee C. H. Cho M. J. Noh Y. B. Kim 2001 Radiosensitizing and topoisomerase I inhibitory effects of Aloe vera, Formitella fraxinea, and Ulmus davidiana extracts Nat. Prod. Sci. 7 60 62 1:CAS:528:DC%2BD3MXotl2ntr4%3D
21. M. K. Lee S. H. Sung H. S. Lee J. H. Cho Y. C. Kim 2001 Lignan and neolignan glycosides from Ulmus davidiana var. japonica Arch. Pharm. Res. 24 198 201 1:CAS:528:DC%2BD38XitlCms7w%3D 10.1007/BF02978256 11440076
22. S. Li R. Y. Chen D. Q. Yu 2007 Study on chemical constituents of Myricaria paniculata I Zhongguo Zhong Yao Za Zhi 32 403 406 1:CAS:528: DC%2BD1cXmvFOhtw%3D%3D 17511145
23. L. F. Liu 1989 DNA topoisomerase poisons as antitumor drugs Annu. Rev. Biochem. 58 351 375 1:CAS:528:DyaL1MXkslSiu70%3D 10.1146/annurev.bi.58.070189. 002031 2549853
24. P. Liu H. Q. Duan Q. Pan Y. W. Zhang Z. Yao 2006 Triterpenes from herb of Potentilla chinesis Zhongguo Zhong Yao Za Zhi 31 1875 1879 1:CAS:528: DC%2BD2sXhtVyntL3J 17285988
25. L. N. Lundgren T. Popoff O. Theander 1981 Dilignol glycosides from needels of Picea abies Phytochemistry 20 1967 1969 1:CAS:528: DyaL38Xot1KlsA%3D%3D 10.1016/0031-9422(81)84046-0
26. Y. H. Moon G. R. Rim 1995 Studies on the constituents of Ulmus parvifolia Korean J. Pharmaco. 26 1 7 1:CAS:528:DyaK2MXmtl2qtb4%3D
27. M. K. Na R. B. An S. M. Lee B. S. Min Y. H. Kim K. H. Bae S. S. Kang 2002 Antioxidant compounds from the stem bark of Sorbus commixta Nat. Prod. Sci. 8 26 29 1:CAS:528:DC%2BD38XjtVOntbo%3D
28. A. Nahrstedt P. Proksch E. E. Conn 1987 (-)-Catechin, flavonol glycosides and flavones from Chamaebatia foliolosa Phytochemistry 26 1546 1547 1:CAS:528:DyaL2sXksFGktLc%3D 10.1016/S0031-9422(00)81860-9
29. A. Pabst D. Barron E. Semon P. Schreier 1992 Two diastereomeric 3-oxo-α-ionol-β-glucosides from raspberry fruit Phytochemistry 31 1649 1652 1:CAS:528:DyaK38XksVOjsL8%3D 10.1016/0031-9422(92)83121-E
30. Y. Pommier 1993 DNA topoisomerase I and II in cancer chemotherapy: update and perspectives Cancer Chemother. Pharmacol. 32 103 108 1:CAS:528: DyaK3sXlvFCru7c%3D 10.1007/BF00685611 8387398
31. M. Potmesil 1994 Camptothecins: from bench research to hospital wards Cancer Res. 54 1431 1439 1:CAS:528:DyaK2cXitVOktbo%3D 8137244
32. L. V. Rubinstein R. H. Shoemaker K. D. Paul R. M. Simon S. Tosini P. Skehan D. A. Scudiero A. Monks M. R. Boyd 1990 Comparison of in vitro anticancer-drug-screening data generated with a lines J. Nat. Cancer Inst. 82 1113 1118 1:CAS:528:DyaK3cXltVylsLw%3D 10.1093/jnci/82.13.1113 2359137
33. S. Sang H. Kikuzaki K. Lapsley R. T. Rosen N. Nakatani C. T. Ho 2002 Sphingolipid and other constituents from almond nuts (Prunus amygdalus Batsch) J. Agric. Food Chem. 50 4709 4712 1:CAS:528:DC%2BD38Xks1aru7w%3D 10.1021/jf020262f 12137501
34. 13C NMR resonances of oleanolic acid, 18-oleanolic acid, ursolic acid and their 11-oxo derivatives Magn. Reson. Chem. 41 636 638 1:CAS:528:DC%2BD3sXlvFSiur8%3D 10.1002/mrc.1214
35. A. A. Siddiqui S. M. Wani R. Rajesh V. Alagarsamy 2006 Phytochemical and pharmacological investigation of Hibiscus rosasinensis Linn Indian J. Pharm. Sci. 68 588 593 1:CAS:528:DC%2BD2sXhtVKhurjE 10.4103/0250-474X.29625
36. W. J. Slichenmyer E. K. Rowinsky R. C. Donehower S. H. Kaufmann 1993 The current status of camptothecin analogues as antitumor agents J. Natl. Cancer Inst. 85 271 291 1:CAS:528:DyaK3sXit1CksL0%3D 10.1093/jnci/85.4.271 8381186
37. E. Smite H. Pan L. N. Lundgren 1995 Lignan glycosides from inner bark of Betula pendula Phytochemistry 40 341 343 1:CAS:528:DyaK2MXotVequr4%3D 10.1016/0031-9422(95)00057-E
38. S. J. Suh W. S. Yun K. S. Kim U. H. Jin J. K. Kim M. S. Kim D. Y. Kwon C. H. Kim 2007 Stimulative effect of Ulmus davidiana Planch (Ulmaceae) on osteoblastic MC3T3-E1 cells J. Ethnopharmacol. 109 480 485 10.1016/j.jep.2006. 08.030 17030479
39. K. Suzuki F. Shono H. Kai T. Uno M. Uyeda 2000 Inhibition of topoisomerases by fatty acids J.Enzym. Inhib. 15 357 366 1:CAS:528: DC%2BD3cXkslOrsbo%3D 10.1080/14756360009040693 10995067
40. I. Tarascou K. Barathieu Y. Andr I. Pianet E. J. Dufourc E. Fouquet 2006 An improved synthesis of procyanidin dimers: regio- and stereocontrol of the interflavan bond European J. Org. Chem. 23 5367 5377 10.1002/ejoc.200600668
41. D. Umlauf J. Zapp H. Becker K. P. Adam 2004 Biosynthesis of the irregular monoterpene artemisia ketone, the sesquiterpene germacrene D and other isoprenoids in Tanacetum vulgare L. (Asteraceae) Phytochemistry 65 2463 2470 1:CAS:528:DC%2BD2cXnslKhs70%3D 10.1016/j.phytochem.2004.08.019 15381410
42. D. Wang M. Xia Z. Cui 2006 New triterpenoids isolated from the root bark of Ulmus pumila L Chem. Pharm. Bull. 54 775 778 10.1248/cpb.54.775 16755042
43. J. C. Wang 1996 DNA topoisomerases Annu. Rev. Biochem. 65 635 692 1:CAS:528:DyaK28XktFamur0%3D 10.1146/annurev.bi.65.070196.003223 8811192
44. W. D. Xie X. Gao Z. J. Jia 2007 A new C-10 acetylene and a new triterpenoid from Conyza canadensis Arch. Pharm. Res. 30 547 551 1:CAS:528:DC%2BD2sXms1alsb8%3D 10.1007/BF02977646 17615671
45. S. W. Yoo J. S. Kim S. S. Kang K. H. Son H. W. Chang H. P. Kim K. Bae C. O. Lee 2002 Constituents of the fruits and leaves of Euodia daniellii Arch. Pharm. Res. 25 824 830 1:CAS:528:DC%2BD3sXht1amsw%3D%3D 10.1007/BF02976999 12510833
46. K. Yoshinari Y. Sashida H. Shimomura 1989 Two new lignan xylosides from the barks of Prunus ssiori and Prunus padus Chem. Pharm. Bull. 37 3301 3303 1:CAS:528:DyaK3cXhvFGhsb0%3D
47. K. Yumiko A. Toshihiro Y. Ken T. Michio T. Toshitake 1995 Structures of five hydroxylated sterols from the seeds of Trichosanthes kirilowii Maxim Chem. Pharm. Bull. 43 1813 1817
48. C. Z. Zhang X. Z. Xu C. Li 1996 Fructosides from Cynomorium songaricum Phytochemistry 41 975 976 1:CAS:528:DyaK28XhtVWntbk%3D 10.1016/0031-9422(95) 00705-9