Antiproliferative and antioxidant activities of a tricin acylated glycoside from sugarcane (Saccharum officinarum) juice

Phytochemistry

Volumn 68, Issue 8, 2007, Pages 1165-1171

  Duarte Almeida, Joaquim Mauricio ^a   Negri, Giuseppina ^b   Salatino, Antonio ^a   de Carvalho, João Ernesto ^c   Lajolo, Franco Maria ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b FEDERAL UNIVERSITY OF SÃO PAULO   (Brazil)

^c UNIVERSITY OF CAMPINAS   (Brazil)

Author keywords

Antioxidant; Antiproliferative; Flavonoids; Orientin; Poaceae; Saccharum officinarum; Sugarcane; Tricin

Indexed keywords

6-HYDROXY-2,5,7,8-TETRAMETHYLCHROMAN-2-CARBOXYLIC ACID; ANTINEOPLASTIC AGENT; ANTIOXIDANT; CHROMAN DERIVATIVE; FLAVONOID; GLUCOSIDE; ORIENTIN; TRICIN 7 O BETA (6'' METHOXYCINNAMIC)GLUCOSIDE; TRICIN-7-O-BETA-(6''-METHOXYCINNAMIC)GLUCOSIDE; TROLOX C; UNCLASSIFIED DRUG;

ARTICLE; CELL PROLIFERATION; CHEMISTRY; COMPARATIVE STUDY; DRUG EFFECT; HUMAN; ISOLATION AND PURIFICATION; SUGARCANE; TUMOR CELL LINE;

ANTINEOPLASTIC AGENTS; ANTIOXIDANTS; CELL LINE, TUMOR; CELL PROLIFERATION; CHROMANS; FLAVONOIDS; GLUCOSIDES; HUMANS; SACCHARUM;

POACEAE; SACCHARUM OFFICINARUM;

EID: 34047257165     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2007.01.015     Document Type: Article

References (30)

1. Agrawal P.K., Thakur R.S., and Bansal M.C. Flavonoids. In: Agrawal P.K. (Ed). Carbon-13 NMR of Flavonoids vol. 39 (1989), Elsevier Science Publishers B.V., New York 95-182
2. Agrianual. 2006. FNP consultoria & agroinformativos. São Paulo, 227-228.
3. Amann C.A. The passenger car and the greenhouse-effect. J. Vehicle Des. 13 (1992) 305-334
4. Andrade P., Ferreres F., and Amaral M.T. Analysis of honey phenolic acids by HPLC, its application to honey botanical characterization. J. Liq. Chromatogr. Relat. Technol. 20 (1997) 2281-2288
5. Arabbi P.R., Genovese M.I., and Lajolo F.M. Flavonoids in vegetable foods commonly consumed in Brazil and estimated ingestion by the Brazilian population. J. Agric. Food Chem. 52 (2004) 1124-1131
6. Bouaziz M., Veitch N.C., Grayer R.J., Simmonds M.S.J., and Damak M. Flavonolignans from Hyparrhenia hirta. Phytochemistry 60 (2002) 515-520
7. Brand-Williams W., Cuvelier M.E., and Berset C. Use of free radical method to evaluate antioxidant activity. Lebensm-Wiss. Technol. 28 (1995) 25-30
8. Burda S., and Oleszek W. Antioxidant and antiradical activities of flavonoids. J. Agric. Food Chem. 49 (2001) 2774-2779
9. Cai H., Hudson E.A., Mann P., Vereschoyle R.D., Greaves P., Manson M.M., Steward W.P., and Gesher A.J. Growth-inhibitory and cell cycle-arresting properties of the rice bran constituent tricin in human-derived breast cancer cells in vitro and in nude mice in vivo. Br. J. Cancer 91 (2004) 1364-1371
10. Cai H., Steward W.P., and Gescher A.J. Determination of the putative cancer chemopreventive flavone tricin in plasma and tissue of mice by HPLC with UV-visible detection. J. Biomed. Chromat. 19 (2005) 518-522
11. Colombo R., Yariwake J.H., Queiroz E.F., Hdjoko K., and Hostettmann K. On-line identification of sugarcane (Saccharum officinarum L.) methoxyflavones by liquid chromatography-UV detection using post-column derivatization and liquid chromatography-mass spectrometry. J. Chromatogr. 1082 (2005) 51-59
12. Cuyckens F., and Claeys M. Mass spectrometry on the structural analysis of flavonoids. J. Mass Spectrom. 39 (2004) 1-15
13. Duarte-Almeida J.M., Santos R.J., Genovese M.I., and Lajolo F.M. Evaluation of the antioxidant activity using the β-carotene/linoleic acid system and the DPPH scavenging method. Ciência Tecnol. Ali. 26 (2006) 446-452
14. Hollman P.C.H. Evidence for health benefits of plant phenols: local or systemic effects?. J. Sci. Food Agric. 81 (2001) 842-852
15. Hudson E.A., Dinh P.A., Kokubu T., Simmonds M.S.J., and Gescher A. Characterization of potentially chemopreventive phenols in extracts of brown rice that inhibit the growth of human breast and colon cancer cells. Cancer Epidemiol. Biomarkers Prev. 9 (2000) 1163-1170
16. Kuwabara H., Mouri K., Otsuka H., Kasai R., and Yamasaki K. Tricin from a Malagasy connaraceous plant with potent antihistaminic activity. J. Nat. Prod. 66 (2003) 1273-1275
17. Legaz M.E., Vicente C., and De Armas R. Analisis de poliaminas y fenoles em preparationes comerciales de azúcar. Int. Sugar J. 100 (1998) 433-436
18. Mabry T.J., Markham K.R., and Thomas M.B. The Systematic Identification of Flavonoids (1970), Springer-Verlag, New York
19. Mabry T.J., Liu Y.L., Pearce J., Dellamonica G., Chopin J., Markham K.R., Paton N.H., and Smith P. New flavonoids from sugarcane (saccharum). J. Nat. Prod. 47 (1984) 127-130
20. Miller H.E. A simplified method for the evaluation of antioxidant. J. Am. Oil Chem. Soc. 48 (1971) 91-95
21. Norbaek R., Aaboer D.B.F., Bleeg I.S., Christensen B.T., Kondo T., and Brandt K. Flavone C-glycoside, phenolic acid and nitrogen contents in leaves of barley subject to organic fertilization treatments. J. Agric. Food Chem. 51 (2003) 809-813
22. Skehan P., Storeng R., Scudeiro D., Monks A., McMahon J., Vistica D., Warren J.T., Bokesch H., Kenney S., and Boyd M.R. New colorimetric cytotoxicity assay for anticancer drug screening. J. Nat. Can. Inst. 82 (1990) 1107-1112
23. Smith P., and Paton N.H. Sugarcane flavonoids. Sugar Technol. Rev. 12 (1985) 117-142
24. Stochmal A., Simonet A.M., Macias F.A., and Oleszek W. Alfafa (Medicago sativa L.) flavonoids. 2. Tricin and chrysoeriol glycosides from aerial parts. J. Agric. Food Chem. 49 (2001) 5310-5314
25. Tsao R., Yang R., Xie S., Sockovie E., and Khanizadeh S. Which polyphenolic compounds contribute to the total antioxidant activities of apple?. J. Agric. Food Chem. 53 (2005) 4989-4995
26. Verschoyle R.E., Greaves P., Cai H., Arndt B., Broggini M., D'Incalci M., Riccio E., Doppalapeed R., Kapetanovic I.M., Stewand W.P., and Gescher A.J. Preliminary safety evaluation of the putative cancer chemopreventive agent tricin, a naturally occurring flavone. Cancer Chemother. Pharmacol. 57 (2006) 1-6
27. Wang H.B., Yao H., Bao G.H., Zhang H.P., and Qin G.W. Flavone glucosides with immunomodulatory activity from the leaves of Pleioblastus amarus. Phytochemistry 65 (2004) 969-974
28. Wenzig E., Kunert O., Ferreira D., Schmid M., Schuhly W., Bauer R., and Hiermann A. Flavonolignans from Avena sativa. J. Nat. Prod. 68 (2005) 289-292
29. Williams C.A., Harborne J.B., and Smith P. The taxonomic significance of leaf flavonoids in Saccharum and related genera. Phytochemistry 13 (1974) 1141-1149
30. Yusof S., Shian L.S., and Osman A. Changes in quality of sugar-cane juice upon delayed extraction and storage. Food Chem. 68 (2000) 395-401