Síntese e avaliação antitumoral do (±)-4-O-demethylKadsurenin M um composto natural e seus análogos/ Synthesis and tumoral test of (±)-4-O-DemethylKadsurenin M a natural compound and analogues

Authors

  • Bruno Hanrry Melo de Oliveira Brazilian Journals Publicações de Periódicos, São José dos Pinhais, Paraná
  • Luiz Andre Araujo Silva
  • Fernando Ferreira Leite
  • Gabrielly Diniz Duarte
  • Samia Sousa Duarte
  • Daiana Karla Frade Silva
  • Marianna Vieira Sobral
  • Luis Cezar Rodrigues

DOI:

https://doi.org/10.34117/bjdv5n10-144

Keywords:

synthesis, kadsurenin, lignans, neolignans

Abstract

The synthesis of neolignan (±)-4-O-DemethylKadsurenin M 2 was achieved through the coupling oxidation of isoeugenol, follow epoxidation of Licarin-A compound 1, one neolignan intermediate. This natural product was analyzed and characterized by NMR 1H and 13C. Compounds 3-5 are derivatives of the compound 1 and together with compound 2 was tested against HL-60 (acute promyelocytic leukemia), HCT-116 (human colorectal carcinoma), MCF-7 (human breast adenocarcinoma) and K562 (chronic myeloid leukemia) cells to evaluate its tumoral activity.

References

A. Mariol, ‘Farmacognosia: da planta ao medicamento’, Porto Alegre, 2007, 6. Ed, p. 1096.

S. Apers, A. Vlietinck, I. Pieters, ‘Lignans and neolignans as lead compounds’, Phytochem. Rev., 2003, 2, 201-217.

M. D. P. Pereira, T. Silva, A. C. C. Aguiar, G. Oliva, R. V. C. Guido, J. K.U. Yokoyama-Yasunaka S. R. B. Uliana, L. M. X. Lopes, ‘Chemical Composition, Antiprotozoal and Cytotoxic Activities of Indole Alkaloids and Benzofuran Neolignan of Aristolochia cordigera’. Planta Med., 2017, 11, 912-920.

L. F. L. Barros, A. Barison, M. J. Salvador, R. de Melo-Silva, E. C. de Cabral, M. N. Eberlin, M. E. A. Stefanello, ‘Constituents of the Leaves of Magnolia ovata’ J. Nat. Prod., 2009, 72, 1529-1532.

L. F. L. Barros, C. A. Ehrenfried, D. Riva, A. Barison, R. de Melo-Silva, M. E. A. Stefanello, ‘Essential oil and other constituents from Magnolia ovata fruit’, Nat. Prod. Commun., 2012, 7, 1365-1367.

J. -L. Li, N. Li, S. -S. Xing, N. Zhang, B. -B. Li, J. -G. Chen, J. -S. Ahn, L. cui, ‘New neo-lignan from Acanthopanax senticosus with protein tyrosine phosphatase 1B inhibitory activity’, Arc. Pharm. Res., 2015, 40, 1265-1270.

G. Li, C. -S. Lee, M. -H. Woo, S. -H. Lee, H. -W. Chang, J. -K. Son, ‘Lignans from the Bark of Machilus thunbergii and Their DNA Topoisomerases I and II Inhibition and Cytotoxicity’ Bio. Pharm. Bull., 2004, 27, 1147-1150.

A. C. Pereira, L. G. Magalhães, U. O. Gonçalves, P. P. Luz, A. C. G. Moraes, V. Rodrigues, P. M. da Matta Guedes, A. A. da Silva Filho, W. R. Cunha, J. K. Bastos, N. P. D. Nanayakkara, M. L. A. e Silva, ‘Schistosomicidal and trypanocidal structure–activity relationships for (±)-licarin A and its (?)- and (+)-enantiomers’, Phytochemistry Elsevier, 2011, 72, 1424-1430.

R. León-Díaz, M. Meckes, S. Said-Fernández, G. M. Molina-Salinas, J. Vargas-Villarreal, J. Torres, J. Luna-Herrera, A. Jiménez-Arellanes, ‘Antimycobacterial neolignans isolated from Aristolochia taliscana’, Mem. Inst. Oswaldo Cruz, 2010, 105, 45-51.

J. S. Lee, J. Kim, Y. U. Yu, Y. C. Kim, ‘Inhibition of phospholipase C?1 and cancer cell proliferation by lignans and flavans fromMachilus thunbergii’, Arc. Pharm. Res., 2004, 27(10), 1043-1047.

B. -Y. Park, B. -S. Min, O. -K. Kwon, S. -R. Oh, K. -S. Ahn, T. -J. Kim, D. -Y. Kim, K. Bae, H. -K. Lee, ‘Increase of Caspase-3 Activity by Lignans from Machilus thunbergii in HL-60 Cells, Bio. Pharm. Bull., 2004, 27, 1305-1307.

L. C. Rodrigues, J. M. Barbosa-Filho, S. D. G. Marques, F. V. P. Borges, L. A. A. Silva, I. H. B. de Laguna, R. Mioso, ‘Formation of bioactive benzofuran via oxidative coupling, using coconut water (Cocos nucifera L.) as biocatalyst’, Org. Commun., 2017, 10, 72-78.

C. Zhao, J. A. Lercher, ‘Upgrading Pyrolysis Oil over Ni/HZSM-5 by Cascade Reactions’, Angew. Chem., 2012, 51, 5935-1940.

X. Jin, R. Yang, Y. Shang, F. Dai, Y. Qian, L. Cheng, B. Zhou, Z. Liu, ‘Oxidative coupling of cinnamic acid derivatives and their radical-scavenging activities’, Chin. Sci. Bull., 2010, 55, 2885-2890.

P. -Y. Chen, Y. -H. Wu, M. -H. Hsu, T. -P. Wang, E. -C. Wang, ‘Cerium ammonium nitrate-mediated the oxidative dimerization of p-alkenylphenols: a new synthesis of substituted (±)-trans-dihydrobenzofurans’, Tetrahedron, 2013, 69, 653-657.

S. G. Muñoz, Ph.D. Thesis, University of Almeriá, at Almeriá 2006.

J.M. Barbosa-Filho, E. V. L. da-Cunha, M. S. Silva, ‘Complete assignment of the 1H and 13C NMR spectra of some lignoids from Lauraceae’, Magn. Reson. Chem., 1998, 36, 929-935.

I. NASCIMENTO, ‘2,3-Dihydrobenzofuran neolignans from Aristolochia pubescens’, Phytochemistry, 1999, 52, 345-350.

S.C. Roy, K. K. Rana, C. Guin, ‘Short and Stereoselective Total Synthesis of Furano Lignans (±)-Dihydrosesamin, (±)-Lariciresinol Dimethyl Ether, (±)-Acuminatin Methyl Ether, (±)-Sanshodiol Methyl Ether, (±)-Lariciresinol, (±)-Acuminatin, and (±)-Lariciresinol Monomethyl Ether and Furofuran Lignans (±)-Sesamin, (±)-Eudesmin, (±)-Piperitol Methyl Ether, (±)-Pinoresinol, (±)-Piperitol, and (±)-Pinoresinol Monomethyl Ether by Radical Cyclization of Epoxides Using a Transition-Metal Radical Source’, J. Org. Chem., 2002, 67, 3242-3248.

W. M. Yi, W. A. Xin,P. X. Fu, ‘Total Synthesis of (±)-Kadsurenin M†’, J. Chem. Res., 1998, 3, 168-168.

I. R. Nascimento, L. M. X. Lopes, L. B. Davin, N. G. Lewis, ‘Stereoselective Synthesis of 8,9-Licarinediols’, Tetrahedron, 2000, 56, 9181-9193.

T. Mosmann, ‘Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays’, J Immunol. Methods, 1983, 65, 55-63.

Downloads

Published

2019-10-11

How to Cite

Oliveira, B. H. M. de, Silva, L. A. A., Leite, F. F., Duarte, G. D., Duarte, S. S., Silva, D. K. F., Sobral, M. V., & Rodrigues, L. C. (2019). Síntese e avaliação antitumoral do (±)-4-O-demethylKadsurenin M um composto natural e seus análogos/ Synthesis and tumoral test of (±)-4-O-DemethylKadsurenin M a natural compound and analogues. Brazilian Journal of Development, 5(10), 19109–19123. https://doi.org/10.34117/bjdv5n10-144

Issue

Section

Original Papers