Structural characterization of tetranortriterpenes from Pseudrocedrela kotschyi and Trichilia emetica and study of their activity towards the chaperone Hsp90

Phytochemistry

Volumn 75, Issue , 2012, Pages 78-89

  Dal Piaz, Fabrizio ^a   Malafronte, Nicola ^a   Romano, Adriana ^a   Gallotta, Dario ^a   Belisario, Maria Antonietta ^a   Bifulco, Giuseppe ^a   Gualtieri, Maria Josefine ^a   Sanogo, Rokia ^b   De Tommasi, Nunziatina ^a   Pisano, Claudio ^c  

^a UNIVERSITY OF SALERNO   (Italy)

^b Departement Medicine Traditionelle (DMT)   (Italy)

^c Sigma Tau SpA   (Italy)

Author keywords

Hsp90; Limonoids; Meliaceae; Pseudrocedrela kotschyi; SPR; Tetranortriterpenes; Trichilia emetica

Indexed keywords

HEAT SHOCK PROTEIN 90; PLANT EXTRACT; TRITERPENE;

ARTICLE; BINDING SITE; BIOLOGY; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ISOLATION AND PURIFICATION; MELIACEAE; METABOLISM; PLANT ROOT; RUBIACEAE; STRUCTURE ACTIVITY RELATION; SURFACE PLASMON RESONANCE;

BINDING SITES; COMPUTATIONAL BIOLOGY; HSP90 HEAT-SHOCK PROTEINS; MELIACEAE; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PLANT EXTRACTS; PLANT ROOTS; RUBIACEAE; STRUCTURE-ACTIVITY RELATIONSHIP; SURFACE PLASMON RESONANCE; TRITERPENES;

MELIACEAE; TRICHILIA EMETICA;

EID: 84856227300     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.12.002     Document Type: Article

References (58)

1. G.E.L. Brandt, M.D. Schmidt, T.E. Prisinzano, and B.S.J. Blagg Gedunin, a novel Hsp90 inhibitor:semisynthesis of derivatives and preliminary structure-activity relationships J. Med. Chem. 51 2008 6495 6502
2. S.K. Calderwood, M.A. Khaleque, D.B. Sawyer, and D.R. Ciocca Heat shock proteins in cancer: chaperones of tumorigenesis Trends Biochem. Sci. 31 2006 164 172 (Pubitemid 43361923)
3. S.K. Calderwood, and D.R. Ciocca Heat shock proteins: stress proteins with Janus-like properties in cancer Int. J. Hypertherm. 24 2008 31 39 (Pubitemid 351167617)
4. A. Casbarra, L. Birolo, G. Infusini, F. Dal Piaz, M. Svensson, P. Pucci, C. Svanborg, and G. Marino Conformational analysis of HAMLET, the folding variant of human alpha-lactalbumin associated with apoptosis Protein Sci. 13 2004 1322 1330 (Pubitemid 38526097)
5. D.R. Ciocca, S.A. Fuqua, S. Lock-Lim, D.O. Toft, W.J. Welch, and W.L. McGuire Response of human breast cancer cells to heat shock and chemotherapeutic drugs Cancer Res. 52 1992 3648 3654
6. D.R. Ciocca, G.M. Clark, A.K. Tandon, S.A. Fuqua, W.J. Welch, and W.L. McGuire Heat shock protein hsp70 in patients with axillary lymph node-negative breast cancer: prognostic implications J. Natl. Cancer Inst. 85 1993 570 574 (Pubitemid 23110932)
7. P.H. Coombes, D.A. Mulholland, and M. Randrianarivelojosia Phragmalin limonoids from the Madagascan Meliaceae Neobeguea leandreana J. Nat. Prod. 66 2003 735 738 (Pubitemid 36782077)
8. M.A. Cooper Label-free screening of bio-molecular interactions Anal. Bioanal. Chem. 377 2003 834 842 (Pubitemid 40882959)
9. M.N. da Silva, M.S.P. Arruda, K.C.F. Castro, M.F. da Silva, G.F. da Silva, J.B. Fernandes, and P.C. Vieira Limonoids of the phragmalin type from Swietenia macrophylla and their chemotaxonomic significance J. Nat. Prod. 71 2008 1983 1987
10. C. Didelot, D. Lanneau, M. Brunet, A.L. Joly, A. De Thonel, G. Chiosis, and C. Garrido Anti-cancer therapeutic approaches based on intracellular and extracellular heat shock proteins Curr. Med. Chem. 14 2007 2839 2847 (Pubitemid 350201651)
11. M. Ehrnsperger, S. Gräber, M. Gaestel, and J. Buchner Binding of non-native protein to Hsp25 during heat shock creates a reservoir of folding intermediates for reactivation EMBO J. 221 1997 221 229 (Pubitemid 27049380)
12. W. Fiskus, Y. Ren, A. Mohapatra, P. Bali, A. Mandawat, R. Rao, B. Herger, Y. Yang, P. Atadja, J. Wu, and K. Bhalla Hydroxamic acid analogue histone deacetylase inhibitors attenuate estrogen receptor-alpha levels and transcriptional activity: a result of hyperacetylation and inhibition of chaperone function of heat shock protein 90 Clin. Cancer Res. 13 2007 4882 4890 (Pubitemid 47294796)
13. C. Garrido, M. Brunet, C. Didelot, Y. Zermati, E. Schmitt, and G. Kroemer Heat shock proteins 27 and 70: anti-apoptotic proteins with tumorigenic properties Cell Cycle 5 2006 2592 2601 (Pubitemid 44785803)
14. P. George, P. Bali, S. Annavarapu, A. Scuto, W. Fiskus, F. Guo, C. Sigua, G. Sondarva, L. Moscinski, P. Atadja, and K. Bhalla Combination of the histone deacetylase inhibitor LBH589 and the Hsp90 inhibitor 17-AAG is highly active against human CML-BC cells and AML cells with activating mutation of FLT-3 Blood 105 2005 1768 1776 (Pubitemid 40223701)
15. C. Giommarelli, V. Zuco, E. Favini, C. Pisano, F. Dal Piaz, N. De Tommasi, and F. Zunino The enhancement of antiproliferative and proapoptotic activity of HDAC inhibitors by curcumin is mediated by Hsp90 inhibition Cell Mol. Life Sci. 67 2010 995 1004
16. F.R. Garcez, W.S. Garcez, E.D. Rodrigues, V.J. Pott, and N.F. Roque Seco-protolimonoids from Trichilia elegans ssp. Elegans Phytochemistry 42 1996 1399 1403 (Pubitemid 27063288)
17. L. Gunatilaka, S. Vanderlan Bolzani, E. Dagne, G.A. Hofmann, K.J. Randall, F.L. McCabe, M.R. Mattern, and D.J. Kingston Limonoids showing selective toxicity to DNA repair-deficient yeast and other constituents of Trichilia emetica J. Nat. Prod. 61 1998 179 184 (Pubitemid 28136767)
18. M.K. Hadden, D.J. Lubbers, and B.S. Blagg Geldanamycin, radicicol, and chimeric inhibitors of the Hsp90 N-terminal ATP binding site Curr. Top. Med. Chem. 6 2006 1173 1182 (Pubitemid 44110928)
19. A.E. Hay, J.R.A. Ioset, K.M. Hua, D. Diallo, R. Brun, and K. Hostettmann Limonoid orthoacetates and antiprotozoal compounds from the roots of Pseudocedrela kotschyi J. Nat. Prod. 70 2007 9 13
20. H. Hieronymus, J. Lamb, K.N. Ross, X.P. Peng, C. Clement, A. Rodina, M. Nieto, J. Du, K. Stegmaier, S.M. Raj, K.N. Maloney, J. Clardy, W.C. Hahn, G. Chiosis, and T.R. Golub Gene expression signature-based chemical genomic prediction identifies a novel class of Hsp90 pathway modulators Cancer Cell 10 2006 21 30
21. J.L. Holmes, S.Y. Sharp, S. Hobbs, and P. Workman Silencing of Hsp90 cochaperone Aha1 expression decreases client protein activation and increases cellular sensitivity to the Hsp90 inhibitor 17-allylamino-17- demethoxygeldanamycin Cancer Res. 68 2008 1188 1197
22. Hosokawa, N., Hirayoshi, K., Kudo, H., Takechi, H., Aoike, A., Kawai, K., Nagata, K., 1992. Inhibition of the activation of heat shock factor in vivo and in vitro by flavonoids. Mol. Cell. Biol. 12, 3490-3498.
23. R. Howes, X. Barril, B.W. Dymock, K. Grant, C.J. Northfield, A.G. Robertson, A. Surgenor, J. Wayne, L. Wright, K. James, T. Matthews, K.M. Cheung, E. McDonald, P. Workman, and M.J. Drysdale A fluorescence polarization assay for inhibitors of Hsp90 Anal. Biochem. 350 2006 202 213 (Pubitemid 43332820)
24. U. Jakob, H. Lilie, I. Meyer, and J. Buchner Transient interaction of Hsp90 with early unfolding intermediates of citrate synthase J. Biol. Chem. 270 1995 7288 7294
25. Y.L. Janin Heat shock protein 90 inhibitors. A text book example of medicinal chemistry J. Med. Chem. 48 2005 7503 7512 (Pubitemid 41698792)
26. A. Jimenez, C. Villarreal, R.A. Toscano, M. Cook, J.T. Arnason, R. Bye, and R. Mata Limonoids from Swietenia humilis and Guarea grandiflora (Meliaceae) Phytochemistry 49 1998 1981 1988 (Pubitemid 28563807)
27. H. Ji-Sook The Hsp90 chaperone machinery: from structure to drug development BMB Reports 42 2009 623 630
28. B. Johnsson, S. Lofas, and G. Lindquist Immobilization of proteins to a carboxymethyldextran-modified gold surface for biospecific interaction analysis in surface plasmon resonance sensors Anal. Biochem. 198 1991 268 277
29. S.A. Khalid, H. Duddeck, and M. Gonzales-Sierra Isolation and characterization of an antimalarial agent of the neem tree Azadirachta indica J. Nat. Prod. 52 1989 922 927 (Pubitemid 19270605)
30. H. Kimura, H. Yukitake, Y. Tajima, H. Suzuki, T. Chikatsu, S. Morimoto, Y. Funabashi, H. Omae, T. Ito, Y. Yoneda, and M. Takizawa ITZ-1, a client-selective Hsp90 inhibitor, efficiently induces heat shock factor 1 activation Chem. Biol. 17 2010 18 27
31. I. Kubo, and J.A. Klocke An insect growth inhibitor from Trichilia roka (Meliaceae) Experientia 38 1982 639 640
32. A.C. Leite, A.L. Pepe Ambrozin, J.B. Fernandes, P.C. Vieira, M.F. da Silva, and S. de Albuquerque Trypanocidal activity of limonoids and triterpenes from Cedrela fissilis Planta Med. 74 2008 1795 1799
33. G.P. Lotz, H. Lin, A. Harst, and W.M. Obermann Aha1 binds to the middle domain of Hsp90, contributes to client protein activation, and stimulates the ATPase activity of the molecular chaperone J. Biol. Chem. 278 2003 17228 17235 (Pubitemid 36799604)
34. D. Mahalingal, R. Swords, J.S. Carew, S.T. Nawrocki, K. Bhalia, and F.J. Giles Targeting Hsp90 for cancer therapy Br. J. Cancer 100 2009 1523 1529
35. O. Martínez-Iglesias, L. Ruiz-Llorente, R. Sánchez- Martínez, L. García, A. Zambrano, and A. Aranda Histone deacetylase inhibitors: mechanism of action and therapeutic use in cancer Clin. Transl. Oncol. 10 2008 395 398
36. P. Meyer, C. Prodromou, B. Hu, C. Vaughan, S.M. Roe, B. Panaretou, P.W. Piper, and L.H. Pearl Structural and functional analysis of the middle segment of Hsp90: implications for ATP hydrolysis and client protein and cochaperone interactions Mol. Cell 11 2003 647 658 (Pubitemid 36385120)
37. P. Meyer, C. Prodromou, C. Liao, B. Hu, S.M. Roe, C.K. Vaughan, I. Vlasic, B. Panaretou, P.W. Piper, and L.H. Pearl Structural basis for the recruitment of the ATPase activator Aha1 to the Hsp90 chaperone machinery EMBO J. 23 2004 1402 1410
38. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J. Comput. Chem. 19 1998 1639 1662 (Pubitemid 128590223)
39. M. Nakatani, T. Iwashita, K. Mizukawa, and T. Hase Trichilinin, a new hexacyclic limonoid from Trichilia roka Heterocycles 26 1987 43 46
40. M. Nakatami, S.A. Abdelgaleil, M.G. Saad, R.C. Huang, M. Doe, and T. Iwagawa Phragmalin limonoids from Chukrasia tabularis Phytochemistry 65 2004 2833 2841 (Pubitemid 39330182)
41. L. Neckers, and K. Neckers Heat-shock protein 90 inhibitors as novel cancer chemotherapeutic agents Expert Opin. Emerg. Drugs 7 2002 277 288 (Pubitemid 35291458)
42. P. Nigro, F. Dal Piaz, D. Gallotta, N. De Tommasi, and M.A. Belisario Inhibition of the thioredoxin system is a basis for the antileukemic potential of 13-hydroxy-15-oxo-zoapatlin Free Radical Biol. Med. 45 2008 875 884
43. S. Ohba, Y. Hirose, K. Yoshida, T. Yazaki, and T. Kawase Inhibition of 90-kD heat shock protein potentiates the cytotoxicity of chemotherapeutic agents in human glioma cells J. Neurosurg. 112 2010 33 42
44. A.W. Opipari, H.M. Hu, R. Yabkowitz, and V.M. Dixit The A20 zinc finger protein protects cells from tumor necrosis factor cytotoxicity J. Biol. Chem. 267 1992 12424 12427
45. B. Panaretou, G. Siligardi, P. Meyer, A. Maloney, J.K. Sullivan, S. Singh, S.H. Millson, P.A. Clarke, S. Naaby-Hansen, R. Stein, R. Cramer, M. Mollapour, P. Workman, P.W. Piper, L.H. Pearl, and C. Prodromou Activation of the ATPase activity of Hsp90 by the stress-regulated cochaperone Aha1 Mol. Cell 10 2002 1307 1318 (Pubitemid 36050873)
46. J. Plescia, W. Salz, F. Xia, M. Pennati, N. Zaffaroni, M.G. Daidone, M. Meli, T. Dohi, P. Fortugno, Y. Nefedova, D.I. Gabrilovich, G. Colombo, and D.C. Altieri Rational design of shepherdin, a novel anticancer agent Cancer Cell 7 2005 457 468 (Pubitemid 40719129)
47. M. Retzlaff, F. Hagn, L. Mitschke, M. Hessling, F. Gugel, H. Kessler, K. Richter, and J. Buchner Asymmetric activation of the Hsp90 dimer by its cochaperone Aha1 Mol. Cell 37 2010 344 354
48. S.M. Roe, C. Prodromou, R. O'Brien, J.E. Ladbury, P.W. Piper, and L.H. Pearl Structural basis for inhibition of the Hsp90 molecular chaperone by the antitumor antibiotics radicicol and geldanamycin J. Med. Chem. 42 1999 260 266 (Pubitemid 29069861)
49. Rohde, M., Daugaard, M., Jensen, M.H., Helin, K., Nylandsted, J., Jaattela, M., 2005. Members of the heat-shock protein 70 family promote cancer cell growth by distinct mechanisms. Genes Dev. 19, 570-582. (Pubitemid 40314989)
50. A. Roy, and S. Saraf Limonoids: overview of significant bioactive triterpenes distributed in plants kingdom Biol. Pharm. Bull. 29 2006 191 201 (Pubitemid 43200882)
51. M.G. Saad, T. Iwagawa, M. Doe, and M. Nakatami Swietenialides, novel ring D opened phragmalin limonoid orthoesters from Swietenia mahogani JACQ Tetrahedron 59 2003 8027 8033 (Pubitemid 37130327)
52. S. Sreeramulu, S.L. Gande, M. Göbel, and H. Schwalbe Molecular mechanism of inhibition of the human protein complex Hsp90-Cdc37, a kinome chaperone-cochaperone, by triterpene celastrol Angew. Chem. Int. Ed. Engl. 48 2009 5853 5855
53. S.K. Tan, H. Osman, K.C. Wong, and P.L. Boey New phragmalin-type limonoids from Swietenia macrophylla King Food Chem. 115 2009 1279 1285
54. O. Trott, and A.J. Olson Autodock Vina: improving the speed and accuracy of docking with a new scoring function, efficient optimization and multithreading J. Comput. Chem. 31 2010 455 461
55. S.J. Uddin, L. Nahar, J.A. Shilpi, M. Shoeb, T. Borkowski, S. Gibbons, M. Middleton, M. Byres, and S.D. Sarker Gedunin, a limonoid from Xylocarpus granatum, inhibits the growth of CaCo-2 colon cancer cell line in vitro Phytother. Res. 21 2007 757 761 (Pubitemid 47217776)
56. Y. Yang, R. Rao, J. Shen, Y. Tang, W. Fiskus, J. Nechtman, P. Atadja, and K. Bhalla Role of acetylation and extracellular location of heat shock protein 90 alpha in tumor cell invasion Cancer Res. 68 2008 4833 4842
57. S.K. Wandinger, K. Richter, and J. Buchner The Hsp90 chaperone machinery J. Biol. Chem. 283 2008 18473 18477
58. J. Wu, Q. Xiao, S. Zhang, X. Li, Z. Xiao, H. Ding, and Q. Li Xyloccensins Q-V, six new 8,9,30-phragmalin ortho ester antifeedants from the Chinese mangrove Xylocarpus granatum Tetrahedron 61 2005 8382 8389 (Pubitemid 41058680)