Natural aristolactams and aporphine alkaloids as inhibitors of CDK1/Cyclin B and DYRK1A

Molecules

Volumn 18, Issue 3, 2013, Pages 3018-3027

  Marti, Guillaume ^a   Eparvier, Véronique ^a   Morleo, Barbara ^a   Le Ven, Jessica ^a   Apel, Cécile ^a   Bodo, Bernard ^b   Amand, Séverine ^b   Dumontet, Vincent ^a   Lozach, Olivier ^c   Meijer, Laurent ^c,d   Guéritte, Françoise ^a   Litaudon, Marc ^a  

^a CNRS   (France)

^b MUSÉUM NATIONAL D'HISTOIRE NATURELLE   (France)

^c STATION BIOLOGIQUE   (France)

^d Centre de Perharidy   (France)

Author keywords

Aporphinoids and aristolactams; Goniothalamus dumontetii; Kinases inhibitors; Oxandra asbeckii; Siparuna spp.

Indexed keywords

APORPHINE DERIVATIVE; ARISTOLACTAM A; ARISTOLACTAM BII; CYCLIN B; CYCLIN DEPENDENT KINASE 1; DYRK KINASE; INDOLE ALKALOID; LACTAM; PLANT EXTRACT; PROTEIN SERINE THREONINE KINASE; PROTEIN TYROSINE KINASE;

ARTICLE; CHEMISTRY; DRUG ANTAGONISM; NUCLEAR MAGNETIC RESONANCE;

APORPHINES; CDC2 PROTEIN KINASE; CYCLIN B; INDOLE ALKALOIDS; LACTAMS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PLANT EXTRACTS; PROTEIN-SERINE-THREONINE KINASES; PROTEIN-TYROSINE KINASES;

EID: 84875581937     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules18033018     Document Type: Article

References (53)

1. Hunter, T. Protein kinases and phosphatases: The yin and yang of protein phosphorylation and signaling. Cell 1995, 80, 225-236.
2. Ferrer, I.; Barrachina, M.; Puig, B.; Martinez de Lagran, M.; Marti, E.; Avila, J.; Dierssen, M. Constitutive Dyrk1A is abnormally expressed in Alzheimer disease, Down syndrome, Pick disease, and related transgenic models. Neurobiol. Dis. 2005, 20, 392-400.
3. Becker, W.; Sippl, W. Activation, Regulation and Inhibition of DYRK1A. FEBS J. 2011, 278, 246-256.
4. Wegiel, J.; Gong, C.-X.; Hwang, Y-W. The role of DYRK1A in neurodegenerative diseases. FEBS J. 2011, 278, 236-245.
5. Harper, J.W.; Adams, P.D. Cyclin-dependent kinases. Chem. Rev. 2001, 101, 2511-2526.
6. Knockaert, M.; Greengard, P.; Meijer, L. Pharmacological inhibitors of cyclin-dependent kinases. Trends Pharmacol. Sci. 2002, 23, 417-425.
7. Shapiro, G.I. Cyclin-Dependent Kinase Pathways as Targets for Cancer Treatment. J. Clin. Oncol. 2006, 24, 1770-1783.
8. Malumbres, M.; Barbacid, M. Mammalian cyclin-dependent kinases. Trends Biochem. Sci. 2005, 30, 630-641.
9. Kamb, A. Cyclin-dependent kinase inhibitors and human cancer. Curr. Top. Microbiol. Immunol. 1998, 227, 139-148.
10. Pines, J. Cyclins and cyclin-dependent kinases: Take your partners. Trends Biochem. Sci. 1993, 18, 195-197.
11. Savage, M.J.; Gingrich, D.E. Advances in the development of kinase inhibitor therapeutics for Alzheimer's disease. Drug Dev. Res. 2009, 70, 125-144.
12. Apel, C.; Dumontet, V.; Lozach, O.; Meijer, L.; Guéritte, F.; Litaudon, M. Phenanthrene derivatives from Appendicula reflexa as new CDK1/cyclin B inhibitors Phytochem. Lett. 2012, 5, 814-818.
13. The species G. dumontetii, which was the first representative of the genus Goniothalamus in New Caledonia was discovered in October 1997 by one of us (M.L.) in the "Special Reserve of Nodela Flora" (South Province), and was named in 2007 by R.M.K. Sauders and Munzinger (Bot. J. Linn. Soc. 2007, 155, 497-503), following the chemical and biological studies carried out.
14. Crohare, R.; Priestap, H.A.; Farina, M.; Cedola, M.; Ruveda, E.A. Aristololactams of Aristolochia argentina. Phytochemistry 1974, 13, 1957-1962.
15. Wang, E.-C.; Shih, M.-H.; Liu, M.-C.; Chen, M.-T.; Lee, G.-H. Studies on constituents of Saururus chinensis. Heterocycle 1996, 43, 969-976.
16. Omar, S.; Chee, C.L.; Ahmad, F.; Ni, J.X.; Jaber, H.; Huang, J.; Nakatsu, T. Phenanthrene lactams from Goniothalamus velutinus. Phytochemistry 1992, 31, 4395-4397.
17. Hedge, V.R.; Borges, S.; Patel, M.; Das, P.R.; Wu, B.; Gullo, V.P.; Chan, T.-Z. New potential antitumor compounds from the plant Aristolochia manshuriensis as inhibitors of the CDK2 enzyme. Bioorg. Med. Chem. 2010, 20, 1344-1346.
18. Li, N.; Wu, J.-L.; Hasegawa, T.; Sakai, J.-I.; Bai, L.-M.; Wang, L.-Y.; Kakuta, S.; Furuya, Y.; Ogura, H.; Kataoka, T.; et al. Bioactive lignans from Peperomia duclouxii. J. Nat. Prod. 2007, 70, 544-548.
19. Xiong, L.; Zhu, C.; Li, Y.; Tian, Y.; Lin, S.; Yuan, S.; Hu, J.; Hou, Q.; Chen, N.; Yang, Y.; Shi, J. Lignans and Neolignans from Sinocalamus affinis and Their Absolute Configurations. J. Nat. Prod. 2011, 74, 1188-1200.
20. Ferreira, M.L.R.; de Pascoli, I.C.; Nascimento, I.R.; Lopes, L.M.X.; Zukerman-Schpector, J. Aporphine and bisaporphine alkaloids from Aristolochia lagesiana var. intermedia. Phytochemistry 2010, 71, 469-478.
21. Guinaudeau, H.; Leboeuf, M.; Debray, M.; Cave, A.; Paris, R.R. Alkaloids of Colubrina faralaotra ssp. faralaotra Planta Med. 1975, 27, 304-316.
22. Bhakuni, D.S.; Tewari, S.; Dhar, M.M. Aporphine alkaloids of annona squamosa. Phytochemistry 1972, 11, 1819-1822.
23. Simas, N.K.; Ferrari, S.F.; Pereira, S.N.; Leitao, G.G. Chemicalecological characteristics of herbivory of Siparuna guianensis seeds by buffy-headed marmosets (Callithrix flaviceps) in the Atlantic forest of southeastern Brazil. J. Chem. Ecol. 2001, 27, 93-108.
24. Chen, K.-S.; Wu, Y.-C.; Teng, C.-M.; Ko, F.-N.; Wu, T.-S. Bioactive alkaloids from Illigera luzonensis. J. Nat. Prod. 1997, 60, 645-647.
25. Denisenko, O.N.; Israilov, I.A.; Chelombitko, V.A.; Yunusov, M.S. Alkaloids of Corydalis marschalliana. Chem. Nat. Compd. 1993, 29, 690-691.
26. Kamenati, T.; Sugahara, T.; Fukumoto, K. Studies on total photolytic synthesis of alkaloids - III: The products of photo-pschorr reaction - Total synthesis of isocorydine. Tetrahedron 1971, 27, 5367-5374.
27. Johns, S.R.; Lamberton, J.A. Alkaloids of Phoebe clemensii Allen (family Lauraceae). Aust. J. Chem. 1967, 20, 1277-1281.
28. Stévigny, C.; Block, S.; Pauw-Gillet, M.C.; de Hoffmann, E.; de Llabres, G.; Adjakidje, V.; Quetin-Leclercq, J. Cytotoxic aporphine alkaloids from Cassytha filiformis. Planta Med. 2002, 68, 1042-1044.
29. Buchanan, M.S.; Carroll, A.R.; Pass, D.; Quinn, R.J. Aporphine Alkaloids from the Chinese Tree Neolitsea aurata var. paraciculata. Nat. Prod. Com. 2007, 2, 255-259.
30. Orito, K.; Uchiito, S.; Satoh, Y.; Tatsuzawa, T.; Harada, R.; Tokuda, M. Aryl Radical Cyclizations of 1-(2'-Bromobenzyl)isoquinolines with AIBN-Bu3SnH: Formation of Aporphines and Indolo[2,1-a]isoquinolines. Org. Lett. 2000, 2, 307-310.
31. Hocquemiller, R.; Rasamizafy, S.; Cavé, A.; Moretti, C. Alcaloïdes des Annonacees XXXVII: Alcaloïdes du Guatteria scandens. J. Nat. Prod. 1983, 46, 335-341.
32. Montenegro, H.; Gutierrrez, M.; Romero, L.I.; Ortega-Barria, E.; Capson, T.L.; Cubilla Rios, L. Aporphine alkaloids from Guatteria spp. with leishmanicidal activity. Planta Med. 2003, 69, 677-679.
33. Gunawardana, Y.A.; Geewanda, P.; Huck-Meng, L.; Bick, I.; Ralph, C. Alkaloids of Hedycarya angustifolia. Heterocycles 1987, 26, 447-456.
34. Sobarzo-Sanchez, E.; Cassels, B.K.; Saitz-Barria, C.; Jullian, C. Oxazine- and oxazole-fused derivatives of the alkaloid boldine and their complete structural and spectral assignments by HMQC and HMBC experiments. Magn. Reson. Chem. 2001, 39, 361-368.
35. Braz-F, R.; Gabriel, S.J.; Gomes, C.M.R.; Gottlieb, O.R.; Bichara, M.D.G.A.; Maia J.G.S. Oxoaporphine alkaloids from Fusea longifolia and Siparuna guianensis. Phytochemistry 1976, 15, 1187-1188.
36. Guinaudeau, H.; Leboeuf, M.; Cavé, A. Aporphine Alkaloids. II. .J. Nat. Prod. 1979, 42, 325-360.
37. Guinaudeau, H.; Leboeuf, M.; Cavé, A. Aporphinoid Alkaloids, III. J. Nat. Prod. 1983, 46, 761-835.
38. Guinaudeau, H.; Leboeuf, M.; Cavé, A. Aporphinoid alkaloids. J. Nat. Prod. 1994, 57, 1033-1135.
39. Castedo, L.; Tojo, G. Phenantrene Alkaloids. In The Alkaloid; Brossi, A., Ed.; Academic: New York, NY, USA, 1990; Volume 39, pp. 99-138.
40. Chen, Z.-L.; Zhu, D.-Y. Aristolochia Alkaloids. In The Alkaloids: Chemistry and Pharmacology; Brossi, A., Ed.; New York, NY, USA, 1987; Volume 31, pp. 29-65.
41. Kumar, V.; Poonam, P.A.K.; Parmar, V.S. Naturally occurring aristolactams, aristolochic acids and dioxoaporphines and their biological activities. Nat. Prod. Rep. 2003, 20, 565-583.
42. Bentley, K.W. β-Phenylethylamines and the isoquinoline alkaloids. Nat. Prod. Rep. 2006, 23, 444-463.
43. Zhang, Y.-N.; Zhong, X.-G.; Zheng, Z.-P.; Hu, X.-D.; Zuo, J.-P.; Hu, L.-H. Discovery and synthesis of new immunosuppressive alkaloids from the stem of Fissistigma oldhamii (Hemsl.) Merr. Bioorg. Med. Chem. 2007, 15, 988-996.
44. Choi, Y.L.; Kim, J.K.; Choi, S.-U.; Min, Y.-K.; Bae, M.-A.; Kim, B.T.; Heo, J.-N. Synthesis of aristolactam analogues and evaluation of their antitumor activity. Bioorg. Med. Chem. Lett. 2009, 19, 3036-3040.
45. Hedge, V.R.; Borges, S.; Pu, H.; Patel, M.; Gullo, V.P.; Wu, B.; Kirchmeier, P.; William, M.J.; Madison, V.; Fischmann, T.; Chan, T.-Z. Semi-synthetic aristolactams - inhibitors of CDK2 enzyme. Bioorg. Med. Chem. Lett. 2010, 20, 1384-1387.
46. Li, L.; Wang, X.; Chen, J.; Ding, H.; Zhang, Y.; Hu, T.-C. Hu, L.-H.; Jiang, H.-L.; Shen, X. The natural product Aristolactam AIIIa as a new ligand targeting the polo-box domain of polo-like kinase 1 potently inhibits cancer cell proliferation. Acta Pharm. Sin. 2009, 30, 1443-1453.
47. Swaffar, D.S.; Holley, C.J.; Fitch, R.W.; Elkin, K.R.; Zhang, C.; Sturgill, J.P.; Menachery, M.D. Phytochemical investigation and in vitro cytotoxic evaluation of alkaloids from Abuta rufescens. Planta Med. 2012, 78, 230-232.
48. Costa, E.V.; Pinheiro, M.L.B.; Barison, A.; Maia, B.H.L.N.S.; Campos, F.R.; Salvador, M.J.; Cabral, E.C.; Eberlin, M.N. Alkaloids from the bark of Guatteria hispida and their evaluation as antioxidant and antimicrobial agents. J. Nat. Prod. 2010, 73, 1180-1183.
49. Chang, H.-C.; Chang, F.-R.; Wu, Y.-C.; Lai, Y.-H. Anti-cancer effect of liriodenine on human lung cancer cells. Kaohsiung J. Med. Sci. 2004, 20, 365-371.
50. Chen, C.-Y.; Chen, S.-Y.; Chen, C.-H. Liriodenine induces G1/S cell cycle arrest in human colon cancer cells via nitric oxide- and p53-mediated pathway. Process Biochem. 2012, 47, 1460-1468.
51. Kim, K.H.; Moon, E.; Choi, S.U.; Kim, S.Y.; Lee, K.R. Biological evaluation of phenolic constituents from the trunk of Berberis koreana. Bioorg. Med. Chem. Lett. 2011, 21, 2270-2273.
52. Li, F.; Awale, S.; Tezuka, Y.; Kadota, S. Cytotoxic constituents from Brazilian red propolis and their structure-activity relationship. Bioorg. Med. Chem. 2008, 16, 5434-5440.
53. Beauchard, A.; Ferandin, Y.; Frère, S.; Lozach, O.; Blairvacq, M.; Meijer, L.; Thiéry, V.; Besson, T. Synthesis of novel 5-substituted indirubins as potential inhibitor of protein kinases. Bioorg. Med. Chem. 2006, 14, 6434-6443.