Flavonoids and other compounds from Ouratea ferruginea (Ochnaceae) as anticancer and chemopreventive agents

Molecules

Volumn 17, Issue 7, 2012, Pages 7989-8000

  Fidelis, Queli C ^a   Castro, Rosane N ^a   Guilhon, Giselle M S P ^b   Rodrigues, Silvane T ^c   De Salles, Cristiane M C ^a   De Salles, J B ^d   De Carvalho, Mario G ^e  

^a FEDERAL RURAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

^b FEDERAL UNIVERSITY OF PARÁ   (Brazil)

^c EMBRAPA AMAZÔNIA ORIENTAL   (Brazil)

^d Centro Universitário da Zona Oeste UEZO   (Brazil)

^e FEDERAL UNIVERSITY OF RIO DE JANEIRO   (Brazil)

Author keywords

Biflavonoids; Chemopreventive agents; Isoflavones; Ouratea ferruginea

Indexed keywords

7 ETHOXYCOUMARIN DEETHYLASE; ANTINEOPLASTIC AGENT; CYTOCHROME P450; FLAVONOID; GLUTATHIONE TRANSFERASE;

ANIMAL; ARTICLE; BIOCATALYSIS; CHEMISTRY; CHEMOPROPHYLAXIS; DRUG EFFECT; MALE; METABOLISM; OCHNACEAE; RAT; WISTAR RAT;

7-ALKOXYCOUMARIN O-DEALKYLASE; ANIMALS; ANTINEOPLASTIC AGENTS; BIOCATALYSIS; CHEMOPREVENTION; CYTOCHROME P-450 ENZYME SYSTEM; FLAVONOIDS; GLUTATHIONE TRANSFERASE; MALE; OCHNACEAE; RATS; RATS, WISTAR;

EID: 84864612104     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17077989     Document Type: Article

References (35)

1. Salvador, G.S.; Cervi, A.C.; Santos dos, E.P. Flórula do morro dos perdidos, serra de araçatuba, estado do paraná, brasil: Ochnaceae. Estud. Biol. 2005, 27, 13-17.
2. Suzart, L.R.; Daniel, J.F.S.; Carvalho, M.G.; Kaplan, M.A.C. Biodiversidade flavonoídica e aspectos farmacológicos em espécies dos gêneros Ouratea e Luxemburgia (Ochnaceae). Quim. Nova 2007, 30, 984-987.
3. de Carvalho, M.G.; Velandia, J.R.; de Oliveira, J.C.C.; Echevarria, A.; Braz-Filho, R.; Grynberg, N.F. Chemical structure, Cytotoxic Antitumour Activities of Biflavonoids from Brazilian Ouratea (Ochnaceae). In Phytochemical and Pharmacologiy II of the Series "Recent Progress in Medicinal Plants"; Majumdar, D.K., Govil, J.N., Singh, V.K., Eds.; SCI Tech Publishing LLC: Houston, TX, USA, 2002; Volume 8, pp. 77-92.
4. Moon, Y.J.; Wang, X.; Morris, M.E. Dietary flavonoids: Effects on xenobiotic and carcinogen metabolism. Toxicol. in Vitro 2006, 20, 187-210. (Pubitemid 43087702)
5. Wang, J.F.; Zhang, C.C.; Chou, K.C.; Wei, D.Q. Structure of cytochrome P450s and personalized drug. Curr. Med. Chem. 2009, 16, 232-244.
6. Hayes, J.D.; Pulford, D.J. The glutathione S-transferase supergene family: Regulation of GST and the contribution of the isoenzymes to cancer chemoprotection and drug resistance. Crit. Rev. Biochem. Mol. Biol. 1995, 30, 521-600.
7. Ames, B.N.; Shigenaga, M.K.; Hagen, T.M. Oxidants, antioxidants, and the degenerative diseases of aging. Proc. Natl. Acad. Sci. USA 1993, 90, 7915-7922. (Pubitemid 23260825)
8. 13C NMR spectra of pentacyclic triterpenoids-A compilation and some salient features. Phytochemistry 1994, 37, 1517-1575.
9. 13C chemical shift assignments. Magn. Reson. Chem. 2000, 38, 977-980.
10. Rubinstein, I.; Goad, L.J.; Clague, A.D.H.; Mulheirn, L.J. The 220 MHz NMR spectra of phytosterols. Phytochemistry 1976, 15, 195-200.
11. Benedek, B.; Weniger, B.; Parejo, I.; Bastida, J.; Arango, G.J.; Lobstein, A.; Codina, C. Antioxidant activity of isoflavones and biflavones isolated from Godoya antioquiensis. Arzneim.-Forsch. 2006, 56, 661-664. (Pubitemid 44521103)
12. McCormick, S.; Robson, K.; Bohm, B. Flavonoids of Wyethia angustifolia and W. helenioides. Phytochemistry 1986, 25, 1723-1726.
13. Tahara, S.; Moriyama, M.; Ingham, J.L.; Mizutani, J. 5, 7, 3′, 4′, 5′-pentaoxygenated and 2′, 6′-diprenylated isoflavones from Piscidia erythrina. Phytochemistry 1991, 30, 2769-2775.
14. Pettit, G.R.; Melody, N.; Thornhill, A.; Knight, J.C.; Groy, T.L.; Herald, C.L. Antineoplastic agents. 579. synthesis and cancer cell growth evaluation of E-Stilstatin 3: A resveratrol structural modification. J. Nat. Prod. 2009, 72, 1637-1642.
15. Harasawa, A.; Tagashira, A. Isolation of 2, 6-dimethoxy-1, 4-benzoquinone from Hydrangea (Hydrangea macrophylla Seringe var. otaksa Makino) and its deodorant activity against methyl mercaptan. Biosci. Biotech. Biochem. 1994, 58, 2073-2074.
16. Kim, H.; Ralph, J. NMR analysis of lignins in CAD-deficient plants. Part 1. Incorporation of hydroxycinnamaldehydes and hydroxybenzaldehydes into lignins. Org. Biomol. Chem. 2003, 1, 268-281.
17. Harborne, J.B.; Mabry, T.J. The Flavonoids: Advances in Research; Chapman and Hall: New York, NY, USA, 1982; p. 116.
18. 13C NMR Studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids. Phytochemistry 1987, 26, 3335-3337.
19. Sivaraman, L.; Leatham, M.P.; Yee, J.; Wilkens, L.R.; Lau, A.F.; Le Marchand, L. CYP1A1 genetic polymorphisms and in situ colorectal cancer. Cancer Res. 1994, 54, 3692-3695. (Pubitemid 24241180)
20. Raunio, H.; Rautio, A.; Gullstén, H.; Pelkonen, O. Polymorphisms of CYP2A6 and its practical consequences. Br. J. Clin. Pharmacol. 2001, 52, 357-363. (Pubitemid 32939440)
21. Udomsuk, L.; Jarukamjorn, K. Factors influencing regulation of CYP2B expression. Thai. Pharm. Health Sci. J. 2009, 4, 524-531.
22. Guengerich, F.P.; Shimada, T. Oxidation of toxic and carcinogenic chemicals by human cytochrome P-450 enzymes. Chem. Res. Toxicol. 1991, 4, 391-407.
23. Moon, J.Y.; Lee, D.W.; Park, K.H. Inhibition of 7-ethoxycoumarin O-deethylase activity in rat liver microsomes by naturally occurring flavonoids: Structure-activity relationships. Xenobiotica 1998, 28, 117-126.
24. Androutsopoulos, V.P.; Papakyriakou, A.; Vourloumis, D.; Spandidos, D.A. Comparative CYP1A1 and CYP1B1 substrate and inhibitor profile of dietary flavonoids. Bioorg. Med. Chem. 2011, 19, 2842-2849.
25. Androutsopoulos, V.P.; Papakyriakou, A.; Vourloumis, D.; Tsatsakis, A.M.; Spandidos, D.A. Dietary flavonoids in cancer therapy and prevention: Substrates and inhibitors of cytochrome P450 CYP1 enzymes. Pharmacol. Ther. 2010, 126, 9-20.
26. Chan, H.Y.; Wang, H.; Leung, L.K. The red clover (Trifolium pratense) isoflavone biochanin A modulates the biotransformation pathways of 7, 12- dimethylbenz[a]anthracene. Br. J. Nutr. 2003, 90, 87-92. (Pubitemid 36903406)
27. Leung, H.Y.; Wang, Y.; Chan, H.Y.; Leung, L.K. Developing a high-throughput system for the screening of cytochrome P450 1A1-inhibitory polyphenols. Toxicol. In Vitro 2007, 21, 996-1002. (Pubitemid 47238242)
28. Wen, X.; Walle, U.K.; Walle, T. 5, 7-Dimethoxyflavone downregulates CYP1A1 expression and benzo[a]pyrene-induced DNA binding in Hep G2 cells. Carcinogenesis 2005, 26, 803-809. (Pubitemid 41214343)
29. Surh, Y.J.; Lee, E.; Lee, J.M. Chemoprotective properties of some pungent ingredients present in red pepper and ginger. Mutat. Res. 1998, 402, 259-267. (Pubitemid 28440282)
30. Ghazali, R.; Waring, R.H. Effects of flavonoids on glutathione-S- transferase in human blood platelets, rat liver, rat kidney, and HT-29 colon adenocarcinoma cell-lines: Potential in drug metabolism and chemoprevention. Med. Sci. Res. 1999, 27, 449-451. (Pubitemid 29391095)
31. Volm, V. Multidrug resistance and its reversal. Anticancer Res. 1998, 18, 2905-2918.
32. Hayes, J.D.; Flanagan, J.U.; Jowsey, I.R. Glutathione transferases. Ann. Rev. Pharmacol. Toxicol. 2005, 45, 51-88. (Pubitemid 40261798)
33. Greenlee, W.F.; Poland, A. An improved assay of 7-ethoxycoumarin O-deethylase activity: Induction of hepatic enzyme activity in C57BL/6J and DBA/2J mice by phenobarbital, 3-methylcholanthrene and 2, 3, 7, 8-tetrachlorodibenzo-p-dioxin. J. Pharmacol. Exp. Ther. 1978, 205, 596-605. (Pubitemid 8393079)
34. Peterson, G.L. A simplification of the protein assay method of lowry et al. which is more generally applicable. Anal. Biochem. 1977, 83, 346-356. (Pubitemid 8269786)
35. Habig, W.H.; Pabst, M.J.; Jakoby, W.B. Glutathione S-Transferases: The first enzymatic in mercapturic acid formation. J. Biol. Chem. 1974, 249, 7130-7139.