Marine two-headed sphingolipid-like compound rhizochalin inhibits EGF-induced transformation of JB6 P+ Cl41 cells

Lipids

Volumn 44, Issue 9, 2009, Pages 777-785

  Fedorov, Sergey N ^a   Makarieva, Tatyana N ^a   Guzii, Alla G ^a   Shubina, Larisa K ^a   Kwak, Jong Y ^b   Stonik, Valentin A ^a  

^a PACIFIC INSTITUTE OF BIOORGANIC CHEMISTRY   (Russian Federation)

^b Dong A University   (South Korea)

Author keywords

Anticarcinogenic properties; Marine two headed sphingolipid like compound; P53 dependent apoptosis; Tumor cells

Indexed keywords

AGLYCONE; ANTINEOPLASTIC AGENT; EPIDERMAL GROWTH FACTOR; PERACETIC ACID; PROTEIN P53; RHIZOCHALIN; RHIZOCHALININ A; RHIZOCHALININ C; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; CANCER PREVENTION; CELL TRANSFORMATION; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; FLOW CYTOMETRY; HUMAN; HUMAN CELL; MOUSE; NONHUMAN; RHIZOCHALINA INCRUSTATA; SPONGE (PORIFERA); STRUCTURE ACTIVITY RELATION; TUMOR CELL;

ANIMALS; ANTICARCINOGENIC AGENTS; APOPTOSIS; CELL LINE, TUMOR; CELL TRANSFORMATION, NEOPLASTIC; FATTY ALCOHOLS; GLYCOSIDES; HUMANS; LEUKEMIA; MICE; PORIFERA; TUMOR SUPPRESSOR PROTEIN P53;

RHIZOCHALINA;

EID: 70349257239     PISSN: 00244201     EISSN: 15589307     Source Type: Journal    
DOI: 10.1007/s11745-009-3322-6     Document Type: Article

References (67)

1. TN Makarieva VA Denisenko VA Stonik YM Milgrom YV Rashkes 1989 Rhizochalin, a novel secondary metabolite of mixed biosynthesis from the sponge Rhizochalina incrustata Tetrahedron Lett 30 6581 6584 10.1016/S0040-4039(01) 89027-4 1:CAS:528:DyaK3cXpsFOlsA%3D%3D
2. F Kong DJ Faulkner 1993 Leucettamols A and B, two antimicrobial lipids from the calcareous sponge Leucetta microraphis J Org Chem 58 970 971 10.1021/jo00056a037 1:CAS:528:DyaK3sXpvVensA%3D%3D
3. RH Willis DJ De Vries 1997 BRS1, a C30 bis-amino, bis-hydroxy polyunsaturated lipid from an Australian calcareous sponge that inhibits protein kinase C Toxicon 35 1125 1129 9248010 10.1016/S0041-0101(96)00218-8 1:CAS:528:DyaK2sXks1Wkt70%3D (Pubitemid 27304198)
4. GM Nicholas TW Hong TF Molinski ML Lerch MT Cancilla CB Lebrilla 1999 Oceanapiside, an antifungal bis-α, ω-amino alcohol glycoside from the marine sponge Oceanapia phillipensis J Nat Prod 62 1678 1681 10654417 10.1021/np990190v 1:CAS:528:DyaK1MXmvVSqsbo%3D (Pubitemid 30030615)
5. BN Zhou MP Mattern RK Johnson DG Kingston 2001 Structure and stereochemistry of a novel bioactive sphingolipid from a Calyx sp Tetrahedron 57 9549 9554 10.1016/S0040-4020(01)00958-9 1:CAS:528:DC%2BD3MXotlWqs7w%3D (Pubitemid 33055637)
6. TN Makarieva VA Denisenko PS Dmitrenok AG Guzii EA Santalova VA Stonik JB MacMillan TF Molinski 2005 Oceanalin A, a hybrid α, ω- bifunctionalized sphingoid tetrahydroisoquinoline β-glycoside from the marine sponge Oceanapia sp Org Lett 7 2897 2900 15987164 10.1021/ol050796c 1:CAS:528:DC%2BD2MXkslSgt7o%3D (Pubitemid 40992591)
7. TN Makarieva AG Guzii VA Denisenko PS Dmitrenok EA Santalova EV Pokanevich TF Molinski VA Stonik 2005 Rhizochalin A, a novel two-headed sphingolipid from the sponge Rhizochalina incrustata J Nat Prod 68 255 257 15730256 10.1021/np049710z 1:CAS:528:DC%2BD2MXptlSktw%3D%3D (Pubitemid 40299818)
8. TN Makarieva PS Dmitrenok AM Zakharenko VA Denisenko AG Guzii R Li CK Skepper TF Molinski VA Stonik 2007 Rhizochalins C and D from the sponge Rhizochalina incrustata. A rare threo-sphingolipid and a facile method for determination of the carbonyl position in α, ω-bifunctionalized ketosphingolipids J Nat Prod 70 1991 1998 18052325 10.1021/np0704811 1:CAS:528:DC%2BD2sXhtlyqs7bO
9. TN Makarieva AM Zakharenko VA Denisenko PS Dmitrenok AG Guzii LK Shubina II Kapustina SN Fedorov 2007 Rhizochalinin A, a new antileukemic two-headed sphingolipid from the sponge Rhizochalina incrustata Chem Nat Comp 43 468 469 10.1007/s10600-007-0164-4 1:CAS:528:DC%2BD2sXht1yisLrM (Pubitemid 350100148)
10. TN Makarieva AG Guzii VA Denisenko PS Dmitrenok VA Stonik 2008 New two-headed sphingolipid-like compounds from the marine sponge Oceanapia sp Rus Chem Bull 57 669 673 10.1007/s11172-008-0106-8 1:CAS:528:DC%2BD1MXjt1WhsLY%3D
11. WK Hong MB Sporn 1997 Recent advances in chemoprevention of cancer Science 278 1073 1077 9353183 10.1126/science.278.5340.1073 1:CAS:528: DyaK2sXnt1Witrk%3D (Pubitemid 27517878)
12. MB Sporn 1976 Approaches to prevention of epithelial cancer during the preneoplastic period Cancer Res 36 2699 2702 1277177 1:STN:280: DyaE283gvVWlsw%3D%3D
13. A Umar JL Viner ET Hawk 2001 The future of colon cancer prevention Ann NY Acad Sci 952 88 108 11795446 1:CAS:528:DC%2BD38XnsFWmtw%3D%3D
14. LW Wattenberg 1995 What are the critical attributes for cancer chemopreventive agents? Ann NY Acad Sci 768 73 81 8526387 10.1111/j.1749-6632. 1995.tb12111.x 1:CAS:528:DyaK28XitV2isbg%3D (Pubitemid 26078721)
15. TJ Smith J-Y Hong Z-Y Wang CS Yang 1995 How can carcinogenesis be inhibited? Ann NY Acad Sci 768 82 90 8526388 10.1111/j.1749-6632.1995.tb12112.x 1:CAS:528:DyaK28XitV2isbk%3D (Pubitemid 26078722)
16. GJ Kelloff JA Crowell VE Steele RA Lubet CW Boone WA Malone, et al. 1999 Progress in cancer chemoprevention Ann NY Acad Sci 889 1 13 10668477 10.1111/j.1749-6632.1999.tb08718.x 1:CAS:528:DC%2BD3cXnt1SnsA%3D%3D
17. S Gupta K Hastak N Ahmad JS Lewin H Mukhtar 2001 Inhibition of prostate carcinogenesis in TRAMP mice by oral infusion of green tea polyphenols Proc Natl Acad Sci USA 98 10350 10355 11504910 10.1073/pnas.171326098 1:CAS:528:DC%2BD3MXmvFWiu70%3D (Pubitemid 32803023)
18. Y-P Lu Y-R Lou XH Li J-G Xie D Brash M-T Huang, et al. 2000 Stimulatory effect of oral administration of green tea or caffeine on ultraviolet light-induced increases in epidermal wild-type p53, p21 (WAFI/CIPI), and apoptotic sunburn cells in SKH-1 mice Cancer Res 60 4785 4791 10987287 1:CAS:528:DC%2BD3cXmsFWhs78%3D
19. Y-P Lu Y-R Lou XH Li J-G Xie P Yen M-T Huang AH Conney 1997 Inhibitory effect of black tea on the growth of established skin tumors in mice: effects on tumor size, apoptosis, mitosis and bromodeoxyuridine incorporation into DNA Carcinogenesis 18 2163 2169 9395217 10.1093/carcin/18.11.2163 1:CAS:528:DyaK2sXnsl2lu7g%3D (Pubitemid 28134744)
20. HS Samaha GJ Kelloff V Steele CV Rao BS Reddy 1997 Modulation of apoptosis by sulindac, curcumin, phenylethyl-3-methylcaffeate and 6-phenylhexyl isothiocyanate apoptotic index as a biomarker in colon cancer chemoprevention and promotion Cancer Res 57 1301 1305 9102217 1:CAS:528:DyaK2sXit1Ohtbo%3D
21. K Yang SA Lamprecht Y Liu H Shinozaki K Fan D Leung, et al. 2000 Chemoprevention studies on the flavonoids quercetin and rutin in normal and azoxymethane-treated mouse colon Carcinogenesis 21 1655 1660 10964096 10.1093/carcin/21.9.1655 1:CAS:528:DC%2BD3cXmsFKisbY%3D
22. T Tanaka H Kohno K Sakata Y Yamada Y Hirose S Sugie, et al. 2002 Modifying effects of dietary capsaicin and rotenone on 4-nitroquinoline-1-oxide- induced rat tongue carcinogenesis Carcinogenesis 23 1361 1367 12151355 10.1093/carcin/23.8.1361 1:CAS:528:DC%2BD38Xms1Knsbw%3D
23. C Huang WY Ma MR Young N Colburn Z Dong 1998 Shortage of mitogen-activated protein kinase is responsible for resistance to AP-1 transactivation and transformation in mouse JB6 cells Proc Natl Acad Sci USA 95 156 161 9419345 10.1073/pnas.95.1.156 1:CAS:528:DyaK1cXjtlyqsA%3D%3D (Pubitemid 28103923)
24. Z Dong MJ Birrer RG Watts LM Matrisian NH Colburn 1994 Blocking of tumor promoter-induced AP-1 activity inhibits induced transformation in JB6 mouse epidermal cells Proc Natl Acad Sci USA 91 609 613 8290571 10.1073/pnas.91.2.609 1:CAS:528:DyaK2cXhsFKgu7w%3D
25. Z Dong SG Watts Y Sun NH Colburn 1995 Progressive elevation of AP-1 activity during preneoplastic-to-neoplastic progression as modeled in mouse JB6 cell variants Int J Oncol 7 359 364 1:CAS:528:DyaK2MXnsFKqsrY%3D
26. LR Bernstein NH Colburn 1989 AP1/jun function is differentially induced in promotion-sensitive and resistant JB6 cells Science 244 566 569 2541502 10.1126/science.2541502 1:CAS:528:DyaL1MXktVGisbw%3D
27. Dong Z et al (2002) Harvesting cells under anchorage-independent cell transformation conditions for biochemical analyses. Sci STKE PL7
28. C Huang W-Y Ma MI Dawson M Rincon RA Flavell Z Dong 1997 Blocking activator protein-1 activity, but not activating retinoic acid response element, is required for the antitumor promotion effect of retinoic acid Proc Natl Acad Sci USA 94 5826 5830 9159159 10.1073/pnas.94.11.5826 1:CAS:528: DyaK2sXjsFOit74%3D (Pubitemid 27241856)
29. W Johannsen 1911 The genotype conception of heredity Am Nat 45 129 159 10.1086/279202
30. FB Churchill 1974 William Johannsen and the genotype concept J Hist Biol 7 5 30 11610096 10.1007/BF00179291 1:STN:280:DC%2BD3Mrnslakug%3D%3D
31. JA Baltrop TC Owen AH Cory JG Cory 1991 5-(3-Carboxymethoxyphenyl)-2-(4, 5-dimethylthiazolyl)-3-(4-sulfophenyl) tetrazolium, inner salt (MTS) and related analogs of 3-(4, 5-dimethylthiazolyl)-2, 5-diphenyltetrazolium bromide (MTT) reducing to purple water-soluble formazans as cell-viability indicators Bioorg Med Chem Lett 1 611 614 10.1016/S0960-894X(01)81162-8
32. NH Colburn BF Former KA Nelson SH Yuspa 1979 Tumour promoter induces anchorage independence irreversibly Nature 281 589 591 492322 10.1038/281589a0 1:CAS:528:DyaL3cXht1ejtrk%3D (Pubitemid 10242874)
33. J Strickland Y Sun Z Dong NH Colburn 1997 Grafting assay distinguishes promotion sensitive from promotion resistant JB6 cells Carcinogenesis 18 1135 1138 9214594 10.1093/carcin/18.6.1135 1:CAS:528:DyaK2sXktF2ltL0%3D (Pubitemid 28132502)
34. P Irigaray JA Newby R Clapp L Hardell V Howard L Montagnier S Epstein D Belpomme 2007 Lifestyle-related factors and environmental agents causing cancer: an overview Biomed Pharmacother 61 640 658 18055160 10.1016/j.biopha.2007.10. 006 1:CAS:528:DC%2BD2sXhsVCgsrvE (Pubitemid 350245728)
35. B Haefner 2003 Drugs from the deep: marine natural products as drug candidates DDT 8 536 544 12821301 1:CAS:528:DC%2BD3sXkvVCntbw%3D
36. K-H Altman J Gertsch 2007 Anticancer drugs from nature-natural products as a unique source of new microtubule-stabilizing agents Nat Prod Rep 24 327 357 10.1039/b515619j (Pubitemid 46504987)
37. D Delmas A Lancon D Colin B Jannin N Latruffe 2006 Resveratrol as a chemopreventive agent Curr Drug Targets 7 423 442 16611030 10.2174/ 138945006776359331 1:CAS:528:DC%2BD28Xjt1Sitbw%3D (Pubitemid 43744833)
38. YP Lu YR Low JG Xie QY Peng I Liao CS Yang MT Huang 2002 Topical applications of caffeine or (-)-epigallocatechin gallate (EGCG) inhibit carcinogenesis and selectively increase apoptosis in UVB-induced skin tumor in mice Proc Natl Acad Sci USA 99 12455 12460 12205293 10.1073/pnas.182429899 1:CAS:528:DC%2BD38XntlCktrc%3D
39. EA Rogozin KW Lee NJ Kang H Yu M Nomura KI Miyamoto AH Conney AM Bode Z Dong 2008 Inhibitory effects of caffeine analogues on neoplastic transformation: structure-activity relationship Carcinogenesis 29 1228 1234 18195054 10.1093/carcin/bgn016 1:CAS:528:DC%2BD1cXot1Wjsbo%3D (Pubitemid 351958703)
40. SN Fedorov OS Radchenko LK Shubina NN Balaneva AM Bode VA Stonik Z Dong 2006 Evaluation of cancer-preventive activity and structure-activity relationships of 3-demethylubiquinone Q2, isolated from the ascidian Aplidium glabrum, and its synthetic analogs Pharm Res 23 70 81 16320003 10.1007/s11095-005-8813-4 1:CAS:528:DC%2BD28Xht1Cltrg%3D (Pubitemid 43214662)
41. 1-S arrest and apoptosis Cancer Res 67 5914 5920 17575161 10.1158/0008-5472.CAN-06-3723 1:CAS:528:DC%2BD2sXmsFCqt7w%3D (Pubitemid 46985027)
42. SN Fedorov LK Shubina AA Kicha NV Ivanchina JY Kwak JO Jin AM Bode Z Dong VA Stonik 2008 Proapoptotic and anticarcinogenic activities of leviusculoside G from the starfish Henricia leviuscula and probable mechanism Nat Prod Commun 3 1575 1580 1:CAS:528:DC%2BD1cXhtlCnsbfM
43. C Huang WY Ma A Goranson Z Dong 1999 Resveratrol suppresses cell transformation and induces apoptosis through a p53-dependent pathway Carcinogenesis 20 237 242 10069459 10.1093/carcin/20.2.237 1:CAS:528: DyaK1MXhsFWgt7g%3D (Pubitemid 29057555)
44. M Nomura D Ichimatsu S Moritani I Koyama Z Dong K Yokogawa K Miyamoto 2005 Inhibition of epidermal growth factor-induced cell transformation and Akt activation by caffeine Mol Carcinog 44 67 76 16044420 10.1002/mc.20120 1:CAS:528:DC%2BD2MXpvFKku7w%3D (Pubitemid 41216409)
45. J Qin He-Ge Chen Q Yan M Deng Liu Jinping S Doerge W Ma Z Dong DW Li 2008 Protein Phosphatase-2A is a target of epigallocatechin-3-gallate and modulates p53-Bak apoptotic pathway Cancer Res 68 4150 4162 18519674 10.1158/0008-5472. CAN-08-0839 1:CAS:528:DC%2BD1cXmsFKmtLk%3D
46. JM Kyriakis J Avruch 2001 Mammalian mitogen-activated protein kinase signal transduction pathways activated by stress and inflammation Physiol Rev 81 807 869 11274345 1:CAS:528:DC%2BD3MXislCrsb8%3D
47. MM Manson KA Holloway LM Howells EA Hudson SM Plummer MS Squires SA Prigent 2000 Modulation of signal-transduction pathways by chemopreventive agents Biochem Soc Trans 28 7 12 10816090 1:CAS:528:DC%2BD3cXhsVKqsbs%3D
48. P-F Hung B-T Wu H-C Chen Y-H Chen C-L Chen M-H Wu H-C Liu M-J Lee Y-H Kao 2005 Antimitogenic effect of green tea (-)-epigallocatechin gallate on 3T3-L1 preadipocytes depends on the ERK and Cdk2 pathways Am J Physiol Cell Physiol 288 1095 1108 10.1152/ajpcell.00569.2004 (Pubitemid 40559385)
49. 2 kinase and survivin associated with opposite role of p38 mitogen-activated protein kinase and AKT Mol Cancer Ther 6 3039 3048 18025287 10.1158/1535-7163.MCT-07-0281 1:CAS:528:DC%2BD2sXhtlWkt7fJ (Pubitemid 350206782)
50. 2-terminal kinase 1/2 J Pharmacol Exp Ther 325 841 849 18337475 10.1124/jpet.107.135442 1:CAS:528:DC%2BD1cXmsVOrtrY%3D (Pubitemid 351724329)
51. W Bursch F Oberhammer R Schulte-Hermann 1992 Cell death by apoptosis and its protective role against disease Trends Pharmacol Sci 13 245 251 1631963 10.1016/0165-6147(92)90077-J 1:STN:280:DyaK38zjs1eqtw%3D%3D
52. JA Hickman 1992 Apoptosis induced by anticancer drugs Cancer Metastasis Rev 11 121 139 1327566 10.1007/BF00048059 1:CAS:528:DyaK2cXl
53. AJ Levine 1997 p53, the cellular gatekeeper for growth and division Cell 88 323 331 9039259 10.1016/S0092-8674(00)81871-1 1:CAS:528:DyaK2sXhtFahtLg%3D (Pubitemid 27131374)
54. C Prives PA Hall 1999 The p53 pathway J Pathol 187 112 126 10341712 10.1002/(SICI)1096-9896(199901)187:1<112::AID-PATH250>3.0.CO;2-3 1:CAS:528:DyaK1MXmvVKrtQ%3D%3D (Pubitemid 29009841)
55. KH Vousden 2000 p53: death star Cell 103 691 694 11114324 10.1016/S0092-8674(00)00171-9 1:CAS:528:DC%2BD3cXos1Snuro%3D
56. Z He W-Y Ma T Hashimoto AM Bode CS Yang Z Dong 2003 Induction of apoptosis by caffeine is mediated by the p53, Bax, and caspase 3 pathways Cancer Res 63 4396 4401 12907610 1:CAS:528:DC%2BD3sXmtFeku7g%3D
57. G Song YB Mao QF Cai LM Yao GL Ouyang SD Bao 2005 Curcumin induces human HT-29 colon adenocarcinoma cell apoptosis by activating p53 and regulating apoptosis-related protein expression Braz J Med Biol Res 38 1791 1798 16302093 10.1590/S0100-879X2005001200007 1:CAS:528:DC%2BD28XitFKjuw%3D%3D
58. S Tanigawa M Fujii D-X Hou 2008 Stabilization of p53 is involved in quercetin-induced cell cycle arrest and apoptosis in HepG2 cells Biosci Biotechnol Biochem 72 797 804 18323654 10.1271/bbb.70680 1:CAS:528: DC%2BD1cXksFejtL0%3D
59. SK Katiyar AM Roy MS Baliga 2005 Silymatin induces apoptosis primarily through a p53-dependent pathway involving Bcl-2/Bax, cytochrome c release, and caspase activation Mol Cancer Ther 4 207 216 15713892 1:CAS:528: DC%2BD2MXhtleku7o%3D
60. S Dhanalakshmi C Agarwal RP Singh R Agarwal 2005 Silibinin up-regulates DNA-protein kinase-dependent p53 activation to enhance UVB-induced apoptosis in mouse epithelial JB6 Cells JBC 280 20375 20383 10.1074/jbc.M414640200 1:CAS:528:DC%2BD2MXktlCmu74%3D (Pubitemid 40776736)
61. K Ito T Nakazato K Yamato Y Miyakawa T Yamada N Hozumi K Segawa Y Ikeda M Kizaki 2004 Induction of apoptosis in leukemic cells by homovanillic acid derivative, capsaicin, through oxidative stress: implication of phosphorylation of p53 at Ser-15 residue by reactive oxygen species Cancer Res 64 1071 1078 14871840 10.1158/0008-5472.CAN-03-1670 1:CAS:528:DC%2BD2cXhtFCgsbg%3D (Pubitemid 38176912)
62. C Corbiere B Liagre F Terro J-L Beneytout 2004 Induction of antiproliferative effect by diosgenin through activation of p53, release of apoptosis-inducing factor (AIF) and modulation of caspase-3 activity in different human cancer cells Cell Res 14 188 196 15225412 10.1038/sj.cr.7290219 1:CAS:528:DC%2BD2cXmt1CgsLs%3D (Pubitemid 43231816)
63. JC Hsu A Dev A Wing C Brew LF Bjeldanes GL Firestone 2006 Indole-3-carbinol mediated cell cycle arrest of LNCaP human prostate cancer cells required the induced production of activated p53 tumor suppressor protein Biochem Pharmacol 72 1714 1723 16970927 10.1016/j.bcp.2006.08.012 1:CAS:528:DC%2BD28Xht1CqtLjE (Pubitemid 44765004)
64. 3 and p53 mediate sulforafane-induced cell cycle delay and apoptosis in non-transformed human T-lymphocytes Cell Mol Life Sci 59 2004 2012 12530531 10.1007/PL00012523 1:CAS:528:DC%2BD38Xps1enurk%3D (Pubitemid 36015873)
65. H Gali-Muhtasib M Diab-Assaf C Boltze J Al-Hmaria R Hartig A Roessner R Schneider-Stock 2004 Thymoquinone extracted from black seed triggers apoptotic cell death in human colorectal cancer cells via a p53-dependent mechanism Int J Oncol 25 857 866 15375533 1:CAS:528:DC%2BD2cXovFWlurY%3D
66. C Huang WY Ma J Li SS Hecht Z Dong 1998 Essential role of p53 in phenethyl isothiocyanate-induced apoptosis Cancer Res 58 4102 4106 9751619 1:CAS:528:DyaK1cXmtlCks7w%3D
67. SN Fedorov AM Bode VA Stonik IA Gorshkova PC Schmid OS Radchenko EV Berdyshev Z Dong 2004 Marine alkaloid polycarpine and its synthetic derivative dimethylpolycarpine induce apoptosis in JB6 cells through p53- and caspase 3-dependent pathways Pharm Res 21 2307 2319 15648263 10.1007/s11095-004-7683-5 1:CAS:528:DC%2BD2MXjslyisg%3D%3D (Pubitemid 40568445)