Cytotoxic studies and in vitro effects of trans-3,4,4',5-tetramethoxystilbene, a bioactive compound isolated from Lonchocarpus punctatus Kunth

  1. Rocío Borges-Argáez
  2. Mirbella Cáceres-Farfán
  3. Nuria De Pedro
  4. Bastien Cautain
  5. José Pérez Del Palacio
  6. Francisca Vicente
  7. Olga Genilloud
  8. Angeles Melguizo
  9. Caridad Díaz
  10. Fernando Reyes
  11. Noureddine El Aouad
  12. Pablo Sansores-Peraza

ISSN: 2395-9525 1405-2768

Year of publication: 2017

Issue: 43

Pages: 165-175

Type: Article

DOI: 10.18387/POLIBOTANICA.43.7 DIALNET GOOGLE SCHOLAR lock_openDialnet editor

More publications in: Polibotánica


The bioassay-guided fractionation of Lonchocarpus punctatus inflorescence extracts led to the purification of the trans (1) and cis (2) isomers of 3,5-dimethoxystilbene, trans-3,4,4’,5-tetramethoxystilbene (3), 4,4’,6’-trimethoxychalcone (4) and 5- hydroxy-7,4’-dimethoxyflavone (5) as their main constituents. the structures of the compounds were established by comparing their nuclear magnetic resonance and mass spectrometry data with that from the literature. among these metabolites, trans-3,4,4’,5-tetramethoxystilbene (3) exhibited potent cytotoxic activity against luminal a (CC50= 2.2 μM), HER2 (CC50= 1.1 μM) and basal triple negative (CC50= 1.8 μM) breast cancer cell lines, but no cytotoxic effects were observed against immortalized hepatocyte cell lines (CC50> 50 μM), and medium (CYP3A4, CYP2C9) and low (CYP2D6) inhibitory properties were observed for P450 isoforms.

Bibliographic References

  • Boatright, W.L., Pyrek, J. St., Song, J., Crum, A.D.. (1998). Identification of trans-3,5-dimethoxystilbene in com- mercial soy protein isolates. Journal of American Oil Chemical Society. 75. 1651
  • Farediah, A., Sohana, A.B., Zainuddin, A.I., Read, R.W.. (1997). Constituents of the leaves of Piper caninum. Planta Medica. 63. 193
  • Gonçalvez de Lima, O., Marini- Bettola, G.B., Sousa, M., De Mello, J.F., Da Silva, E.C., De Oliveira, L.L., Cotias, C.T.. (1975). Antimicrobial substances from higher plants. XLVI. Initial observations on biological effects of extracts from the stembark and rootbark of Lonchocarpus violaceus (L. longistylus), a Mexican Mayan, Guatemalan and Honduran plant. Revista Institucional de Antibioticos. 15. 3-15
  • Holliday, D.L., Speirs, V.. (2011). Choosing the right cell line for breast cancer research. Breast Cancer Research Breast Cancer Research. 13. 215-216
  • Hyun, O.Y., Dae-Yeon, S., Byung, H.H.. (1995). Isolation and characterization of Platelet-activating Factor receptor binding antagonist from biota orientalis. Planta Medica. 61. 37-40
  • Jang, M., Cai, L., Udeani, G.O., Slowing, K.V., Thomas, C.F., Beecher, C.W., Fong, H.H., Farnsworth, N.R., Kinghorn, A.D., Mehta, R.G., Moo, R.C., Pezutto, J.M.. (1997). Cancer chemo- preventive activity of resveratrol, a natural product derived from grapes. Science. 275. 218
  • Kinghorn, D. A., Young-Won, C., Swanson, S.M.. (2009). Discovery of Natural Product anticancer agents from bio- diverse Organisms. Current Opinion in Drug Discovery & Development. 12. 189
  • Lai, C.H., Rao, Y.K., Fang, S.H., Sing, Y.T., Tzeng, Y.M.. (2010). Identification of 3’,4’,5’-trimethoxychalcone analogues as potent inhibitors of Helicobacter pylori-induced inflammation. Bioorganic & Medicinal Chemistry Letters. 20. 5462
  • Li, H., Ka-Kei, W.W., Zheng, Z., Tao-Che, C., Yu, L., Jie-Li, Z., Chun-Wu, Y., Cheng, K.W., Yu, J., Hin-cho, C., Wang, M.. (2009). 2,3 ́,4,4 ́,5 ́-Pentamethoxy- trans-stilbene, a resveratrol derivative, is a potent inducer of apoptosis in colon cancer cells via targeting micro- tubules. Biochemical Pharmacology. 7. 1224
  • Marta, M., Lupi, A., Di Chiara, G., Delle, M.F., Marini-Bettolo, G.B.. (1979). Synthesis of longistyline a, b, c, D and other new prenylated stylbenes. Gazzeta Chimica Italiana. 109. 323-324
  • Mendieta, R.M,, Del Amo, S.. (1981). Plantas medicinales del estado de Yucatán. Instituto Nacional de Investigación sobre Recursos Bióticos. Compañía Editorial Continental. Distrito Federal, México.
  • Perou, C.M., Súrlie, T., Eisen, M.B., Van De Rijn, M., Jeffreyk, S.S., Rees, C.A., Pollack, J.R., Ross, D.T., Johnsen, H., Akslen, L., Flugel, O., Pergamen- Schikov, A., Williams, C., Zhu, S.X., Lunning, P.E., Burresen-Dale, A.L., Brown, P.O., Botstein, D.. (2000). Molecular portraits of human breast tumours. Nature. 406. 747
  • Robeti, M., Pizziranti, D., Simoni, D., Rondanin, R.. (2003). Synthesis and biological eva- luation of resveratrol and analogues as apoptosis inducing agents. Journal of Medicinal Chemistry. 46. 3546