Constituents of Plantago major subsp. intermedia with antioxidant and anticholinesterase capacities
The methanol extract of Plantago major subsp. intermedia (Gilib.) Lange afforded 4 known compounds, namely isomartynoside (1), 10-hydroxymajoroside (2), b -sitosterol (3), and ursolic acid (4). Their structures were established by spectroscopic methods. After determination of the total phenolic and flavonoid contents of the methanol extract, the antioxidant potentials of the crude extract and isolated compounds 1-4 were determined by b -carotene bleaching, DPPH free radical and ABTS cation radical scavenging, and cupric reducing antioxidant capacity methods. The methanol extract, rich in phenolic contents, indicated the same DPPH free radical scavenging activity (72% inhibition) as a standard compound, butylated hydroxytoluene, at 100 m g/mL. Isomartynoside (1), a phenylpropanoid glycoside, showed the best inhibition of lipid peroxidation, ABTS cation radical scavenging activity, and cupric reducing antioxidant capacity among the tested samples. The anticholinesterase effects of the methanol extract and isolated compounds 1-4 were established using the Ellman method. A triterpenic acid, ursolic acid (4), exhibited moderate acetyl- (54.01 \pm 0.82%) and butyryl-cholinesterase (68.74 \pm 0.36%) inhibitory activity at 200 m g/mL. Isomartynoside (1) was isolated here for the first time from a Plantago species; the antioxidant and anticholinesterase activities of P. major subsp. intermedia and compounds 1-2 were not previously determined.
Constituents of Plantago major subsp. intermedia with antioxidant and anticholinesterase capacities
The methanol extract of Plantago major subsp. intermedia (Gilib.) Lange afforded 4 known compounds, namely isomartynoside (1), 10-hydroxymajoroside (2), b -sitosterol (3), and ursolic acid (4). Their structures were established by spectroscopic methods. After determination of the total phenolic and flavonoid contents of the methanol extract, the antioxidant potentials of the crude extract and isolated compounds 1-4 were determined by b -carotene bleaching, DPPH free radical and ABTS cation radical scavenging, and cupric reducing antioxidant capacity methods. The methanol extract, rich in phenolic contents, indicated the same DPPH free radical scavenging activity (72% inhibition) as a standard compound, butylated hydroxytoluene, at 100 m g/mL. Isomartynoside (1), a phenylpropanoid glycoside, showed the best inhibition of lipid peroxidation, ABTS cation radical scavenging activity, and cupric reducing antioxidant capacity among the tested samples. The anticholinesterase effects of the methanol extract and isolated compounds 1-4 were established using the Ellman method. A triterpenic acid, ursolic acid (4), exhibited moderate acetyl- (54.01 \pm 0.82%) and butyryl-cholinesterase (68.74 \pm 0.36%) inhibitory activity at 200 m g/mL. Isomartynoside (1) was isolated here for the first time from a Plantago species; the antioxidant and anticholinesterase activities of P. major subsp. intermedia and compounds 1-2 were not previously determined.
___
- 1. Tutel, B. In Flora of Turkey and the East Aegean Islands, Vol.7; Davis, P. H., Ed.; Edinburgh University Press, Edinburgh, 1982.
- 2. Tan, K.; Suda, J. In Flora of Turkey and the East Aegean Islands, Vol. 11 (Suppl.); G¨uner, A.; Ozhatay, N.; Ekim, ¨ T.; Ba¸ser, K. H. C., Eds.; Edinburgh University Press, Edinburgh, 2000.
- 3. Ronsted, N.; G¨obel, E.; Franzyk, H.; Jensen, S. R.; Olsen, C. E. Phytochemistry 2000, 55, 337-348.
- 4. Baytop, T. Therapy with Plants in Turkey (Past and Present), Publications of ˙ Istanbul University, ˙ Istanbul, 1984.
- 5. Samuelsen, A. B. J. Ethnopharmacol. 2000, 71, 1-21.
- 6. Geng, F.; Yang, L.; Chou, G.; Wang, Z. Phytother. Res. 2010, 24, 1088-1094.
- 7. Li, L.; Liu, C.; Liu, Z.; Tsao, R.; Liu, S. Chinese J. Chem. 2009, 27, 541-545.
- 8. Calis, I.; Lahloub, M. F.; Rogenmoser, E.; Sticher, O. Phytochemistry 1984, 23, 2313-2315.
- 9. Handjieva, N.; Taskova, R.; Popov, S. Z. Naturforsch. 1993, 48c, 827-828.
- 10. DellaGreca, M. D.; Monaco, P.; Previtera, L. J. Nat. Prod. 1990, 53, 1430-1435.
- 11. Ogura, M.; Cordell, G. A.; Farnsworth, N. R. Lloydia 1977, 40, 157-168.
- 12. Slinkard, K.; Singleton, V. L. Am. J. Enol. Viticult. 1977, 28, 49-55.
- 13. Moreno, M. I. N.; Isla, M. I.; Sampietro, A. R.; Vattuone, M. A. J. Ethnopharmacol. 2000, 71, 109-114.
- 14. Miller, H. E. J. Am. Oil Chem. Soc. 1971, 48, 91. 15. Blois, M. S. Nature 1958, 181, 1199-1200.
- 16. Re, R.; Pellegrini, N.; Proteggente, A.; Pannala, A.; Yang, M.; Rice-Evans, C. Free Radical Biol. Med. 1999, 26, 1231-1237.
- 17. Apak, R.; G¨u¸cl¨u, K.; Ozy¨ ¨ urek, M.; Karademir, S. E. J. Agric. Food Chem. 2004, 52, 7970-7981.
- 18. Ellman, G. L.; Courtney, K. D.; Andres, V.; Featherstone, R. M. Biochem. Pharmacol. 1961, 7, 88-95.
- 19. Galvez, M.; Martin-Cordero, C.; Houghton, P. J.; Ayuso, M. J. J. Agric. Food Chem. 2005, 53, 1927-1933.
- 20. Stanisavljevic, I. T.; Stojicevic, S. S.; Velickovic, D. T.; Lazic, M. L.; Veljkovic, V. B. Sep. Sci. Technol. 2008, 43, 3652-3662.
- 21. Kisiel, W.; Piozzi, F. Phytochemistry 1999, 51, 1083-1085. 22. Kim, H. J.; Woo, E. R.; Shin, C. G.; Hwang, D. J.; Park, H.; Lee, Y. S. Arch. Pharm. Res. 2001, 24, 286-291.
- 23. Chu, H. B.; Tan, N. H.; Zhang, Y. M. J. Chem. Sci. 2007, 62, 1465-1470.
- 24. Kang, D. G.; Lee, Y. S.; Kim, H. J.; Lee, Y. M.; Lee, H. S. J. Ethnopharmacol. 2003, 89, 151-154.
- 25. De Angel, R. E.; Smith, S. M.; Glickman, R. D.; Perkins, S. N.; Hursting, S. D. Nutr. Cancer 2010, 62, 1074-1086.
- 26. Da Silva Ferreira, D.; Esperandim, V. R.; Toldo, M. P. A.; Saraiva, J.; Cunha, W. R.; De Albuquerque, S. Parasitol. Res. 2010, 106, 985-989.
- 27. Ringbom, T.; Segura, L.; Noreen, Y.; Perera, P.; Bohlin, L. J. Nat. Prod. 1998, 61, 1212-1215.