New Prenylated Flavanones from Esenbeckia berlandieri ssp. acapulcensis
DOI:
https://doi.org/10.29356/jmcs.v50i2.1305Keywords:
Esenbeckia berlandieri ssp. acapulcensis, rutaceae, prenylflavanonesAbstract
Abstract. Three new (1-3) and four known prenylated flavanones as well as friedelin were isolated from the aerial parts of Esenbeckia berlandieri ssp acapulcensis (Rutaceae). The structures of the new compounds were elucidated as 5,7-dihydroxy-8-(2,3-epoxy-3-methylbutyl) flavanone (1), 5,4´-dihydroxy-7-methoxy-8-(2,3-dihydroxy-3-methylbutyl)flavanone (2), and 5,7,4´-trihydroxy-8-(2,3-dihydroxy-3-methylbutyl)flavanone (3). The isolated flavanones possess diferentially functionalized isoprene units at C-8, and this is the first report of flavanones isolated from Esenbeckia species.
Resumen. Tres flavanonas preniladas novedosas (1-3), cuatro conocidas así como friedelina fueron aisladas de las partes aéreas de
Esenbeckia berlandieri ssp acapulcensis (Rutaceae). Las estructuras de los compuestos nuevos fueron determinadas como 5,7-dihidroxi-8- (2,3-epoxi-3-metilbutil)flavanona (1), 5,4´-dihidroxi-7-metoxi-8-(2,3- dihidroxi-3-metilbutil)flavanona (2) y 5,7,4´-trihidroxi-8-(2,3-dihidroxi-3-metilbutil)flavanona (3). Las flavanonas aisladas poseen isoprenilos con diferente funcionalidad unidos a C-8, y este es el primer reporte de flavanonas aisladas de especies de Esenbeckia.
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References
2. Dreyer, D. L. Phytochemistry 1980, 19, 941-944.
3. Cano, A.; Bucio, J.; Espinoza, M.; Ruiz-Cancino, A. Rev. Soc. Quím. Méx. 2000, 44, 155-157.
4. Oliveira, M. F.; Santana, A.; Conserva, L.; Maia, J.; Guilhon, G. Phytochemistry 1996, 44, 647-649.
5. Guilhon, G.; Baetas, A.; Maia, J.; Conserva, L. Phytochemistry 1994, 37, 1193-1195.
6. Rios, M. Y.; Delgado, G. Biochem. Syst. Ecol. 2002, 30, 697-699.
7. Rios, M. Y.; Rosas-Olmos, E.; Aguilar-Guadarrama, A. B. Biochem. Syst. Ecol. 2002, 30, 367-369.
8. Rios, M. Y.; Aguilar-Guadarrama, A. B.; Delgado, G. Biochem. Syst. Ecol. 2002, 30, 977-979.
9. De Oliveira, P.; Conserva, L.; Brito, A.; Lemos, R. Pharma. Biol. 2005, 43, 53-57.
10. Trani, M.; Carbonetti, A.; Delle Monache, G.; Delle Monache, F. Fitoterapia 2004, 75, 99-102.
11. Rios, M.; Delgado, G. Phytochemistry 1992, 31, 3491-3494.
12. Rios, M.; Delgado, G. J. Nat. Prod. 1992, 55, 1307-1309.
13. Bevalot, E.; Fornet, A.; Moretti, C.; Vaquete, J. Planta Medica 1984, 50, 522-523.
14. Nakatsu, T.; Johns, T.; Kubo, I. J. Nat. Prod. 1990, 53, 1508-1513.
15. Dreyer, D.; Pickering, M.; Cohen, P. Phytochemistry 1972, 11, 705-713.
16. Kubo, Y. J. Chromatogr. 1991, 538, 187-191.
17. Jayaraman, I.; Ghanim, A.; Khan, H. Phytochemistry 1980. 18, 1267-1268.
18. Mitscher, L. A.; Raghev-Rao, G. S.; Khanna, Y.; Veysoglu, T.; Drake, S. Phytochemistry 1983, 22, 573-575.
19. Mitscher, L. A.; Leu, R.; Bathala, M. S.; Wu, W. N.; Beal, J. L.; White, R. Lloydia 1972, 35, 157-159
20. Saitoh, T.; Kinoshita, T.; Shibata, S. Chem. Pharm. Bull. 1976, 24, 752-754
21. Bohlmann, F.; Zdero, Ch.; King, R. M.; Robinson, H. Phytochemistry 1979, 18, 1246-1247.
22. Komatsu, M.; Yokoe, I.; Shirataki, Y. Chem. Pharm. Bull. 1978, 26, 3863-3870.
23. Siddiqui, B. S.; Syed Tarek, A.; Munawwer, R.; Kardar, M. N. Helv. Chim. Acta 2003, 86, 2787-2796
24. Mol, J. N.; Robbins, M. P.; Dixon, R. A.; Veltkamp, E. Phytochemistry 1985, 24, 2267.
25. Gaffield, V.; Lundin, R. E.; Gentili, B.; Robert, M. H. Bioorg. Chem. 1975, 4, 259.
26. Grundon, M. F.; Coll, I. S. Phytochemistry 1975, 14, 143-150
27. It is interesting to note that several years ago Bohlmann [33] proposed that the placement of the prenyl group at C(6) or at C(8) in the flavanone nucleus could be determined by the difference in the chemical shifts of the methyl hydrogens H(4´´) and H(5´´). If this difference was near zero, the prenyl group would be at C(8), while a prenyl group at C(6) would produce different chemical shifts for the methyl groups. These observations are not followed by compounds 1-3. Therefore, additional arguments should be considered for structural assignments.
28. Waterman, P. G.. Phytochemical diversity in the order Rutales, In: Phytochemical Potential of tropical plants (K. R. Downum, et al.). Plenum Press. New York. 1993, 203-233.
29. Kitaoka, M; Kadokawa, M., Sugano, M.; Ichikawa, K.; Taki, M.; Takaishi, S.; Iijima, Y.; Tsutsumi, S.; Boriboon, M.; Akiyama, T. Planta Med. 1998, 64, 511-515.
30. Miyamoto, M.; Matsushita, Y.; Kiyokawa, C.; Fukuda, C.; Iijima, Y.; Sugano, M.; Akiyama, T. Planta Med. 1998, 64, 516-519.
31. Meyer, B. N.; Ferrigni, N, R.; Putnam, J. E.; Jacobsen, L. B.; Nichols, D. E.; McLaughlin, J. L. Planta Med. 1982, 45, 31-34.
32. Mitscher, L.; Leu, R.; Bathala, M.; Wu, W.; Beal, J. Lloydia 1972, 35, 157-166.
33. Bohlmann, F.; Zdero, Ch.; Robinson, H.; King, R. M. Phytochemistry 1981, 20, 2245-2248.
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