Biochemical, Molecular and Pharmacological Studies of the Wheat (Triticum aestivum L) Flavone, Tricin.
PhD thesis, Concordia University.
Biochemical, Molecular and Pharmacological Studies of the Wheat (Triticum aestivum L) Flavone, Tricin
Amira Moheb, Ph.D.
Concordia University, 2012
Tricin (5,7,4'-trihyroxy-3',5'-dimethoxyflavone), a naturally occurring compound, is a characteristic constituent of the grass family, including cereal grain plants, and has been isolated from rice, oat, maize, and wheat. Apart from being a powerful antioxidant, antimutagenic, and anti-inflammatory agent, tricin has been considered as an efficient chemopreventive agent in growth inhibition of human malignant breast tumour cells and colon cancer cells. However, its high commercial price as a pure compound may hinder further experimentation. Wheat is considered one of the main staple foods in Canada and worldwide, and is the most widely adapted crop to abiotic stresses. The main aim of this study is to investigate the effects of abiotic stress factors, such as cold, drought, and salt treatments, among others, on the biosynthesis and accumulation of tricin in different parts of wheat (Triticum aestivum L), with aim of defining an optimum source for tricin production in this important crop. This thesis consists of four research chapters.
The first chapter focuses on an investigation of the phenolic profile of two varieties of wheat (Triticum aestivum L) leaves grown under normal and cold stress conditions. The leaf ‘phenolomes’ were established for two varieties: the winter wheat (Triticum aestivum L. var Claire) and spring wheat (Triticum aestivum L. var, Bounty) using a combination of HPLC-ESI-MS techniques. Phenolic compounds accumulated at a higher level in the Claire than in the Bounty variety, and detected in significant amounts in the apoplast compartment. The accumulation of a mixture of beneficial flavonoids in cold-acclimated wheat leaves attests to its potential use as an inexpensive supplement of a health-promoting component to the human diet.
The second chapter describes the distribution of tricin in different parts of wheat with the aim to designate a rich source for its utilization. Winter wheat husk was identified as the most valuable part. Its tricin content is considered the highest in any plant materials suggesting the use of winter wheat husk as a good source of tricin. Moreover, the potential anticancer effect of tricin on two cancer cell lines was evaluated where it was revealed to have a selective anticancer effect.
In the third chapter, the selective anticancer effect of several methylated phenolic and flavonoids compounds were tested in vitro on cell cultures, using a LDH-spectrophotometer method to assess the viability of the cell lines. Several candidates were found to possess a remarkable antitumor activity on these malignant cell lines, such as trimethyltricetin, a tricin derivative that exhibited a superior selective activity against human adenocarcinomic alveolar basal epithelial cells (A-549).
In the last chapter, the biosynthesis of tricin is discussed. The expression and the enzyme activity of TaOMT2, the enzyme that catalyzes the methylation of tricetin to tricin, were measured at different wheat developmental stages and in response to different abiotic stresses such as cold, salt and drought. The significant accumulation of tricin in the inflorescences suggests that tricin may play a role in protecting the seeds against biotic and abiotic stresses.
Adams, M., Efferth, T., Bauer, R., 2006. Activity-guided isolation of scopoletin and isoscopoletin, the inhibitory active principles towards CCRF-CEM leukaemia cells and multi-drug resistant CEM/ADR5000 C cells, from Artemisia argyi. Planta Med 72, 862-864.
Agency, C. F. I., 2010. The elements within the nutrition facts table
Andersen, M. M., K. R., 2006. Flavonoids: chemistry, biochemistry and applications. CRC Press, Boca Raton.
Anderson, J. A., Perkin, A. G., 1931. CCCLXV.-The yellow colouring matter of khapli wheat, Triticum dicoccum. J Chem Soc (Resumed), 2624-2625.
Anderson, J. W., Baird, P., Davis Jr, R. H., Ferreri, S., Knudtson, M., Koraym, A., Waters, V., Williams, C. L., 2009. Health benefits of dietary fiber. Nutr Rev 67, 188-205.
Antia, F. P., Abraham, P., 1997. Clinical Dietetics and Nutrition. Oxford University Press, Usa (1998-10-29), 73–77.
Asenstorfer, R. E., Wang, Y., Mares, D. J., 2006. Chemical structure of flavonoid compounds in wheat (Triticum aestivum L.) flour that contribute to the yellow colour of Asian alkaline noodles. J Cereal Sci 43, 108-119.
Baccichetti, F. P., IT), Bordin, Franco, Carlassare, Francesco, Dall'acqua, Francesco, Guiotto, Adriano, Pastorini, Giovanni, Rodighiero, Giovanni (Padua, IT), Rodighiero, Paolo, Vedaldi, Daniela, 1982. Furocoumarin for the photochemotherapy of psoriasis and related skin diseases. Consiglio, Nazionale Delle Ricerche (Rome, IT), United States.
Back, K., 2001a. Hydroxycinnamic acid amides and their possible utilization for enhancing agronomic traits. Plant Pathol J. 17, 123-127.
Back, K., Jang, S. M., Lee, B.-C., Schmidt, A., Strack, D., Kim, K.-M., 2001b. Cloning and characterization of a hydroxycinnamoyl-CoA:Tyramine N-(Hydroxycinnamoyl) transferase induced in response to UV-C and wounding from Capsicum annuum. Plant Cell Physiol. 42, 475-481.
Baublis, A. J., Lu, C., Clydesdale, F. M., Decker, E. A., 2000. Potential of wheat-based breakfast cereals as a source of dietary antioxidants. J Am Coll Nutr. 19, 308S-311S.
Bing, L., Hongxia, D., Maoxin, Z., Di, X., Jingshu, W., 2007. Potential resistance of tricin in rice against brown planthopper Nilaparvata lugens (Stal). Acta Ecologica Sinica 27, 1300-1306.
Bohm, B. A., 1998. Introduction to flavonoids. Harwood Academic Publishers.
Bosanquet AG, B. P., 2004. Ex vivo therapeutic index by drug sensitivity assay using fresh human normal and tumor cells. J Exp Ther Oncol 4, 145-154.
Boyer, J. S., 1982. Plant productivity and environment. Science 218, 443-448.
Bradford, M. M., 1976. A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72, 248-254.
Brazier-Hicks, M., Evans, K. M., Gershater, M. C., Puschmann, H., Steel, P. G., Edwards, R., 2009. The C-glycosylation of flavonoids in cereals. J. Biol. Chem. 284, 17926-17934.
Brouillard, R., Cheminat, A., 1988. Flavonoids and plant color. Prog Clin Biol Res 280, 93-106.
Butsat, S., Siriamornpun, S., 2010. Phenolic acids and antioxidant activities in husk of different thai rice varieties. Food Sci and Technol Internat 16, 329-336.
Cai, H., Al-Fayez, M., Tunstall, R. G., Platton, S., Greaves, P., Steward, W. P., Gescher, A. J., 2005a. The rice bran constituent tricin potently inhibits cyclooxygenase enzymes and interferes with intestinal carcinogenesis in ApcMin mice. Mol Cancer Ther. 4, 1287.
Cai, H., Boocock, D., Steward, W., Gescher, A., 2007. Tissue distribution in mice and metabolism in murine and human liver of apigenin and tricin, flavones with putative cancer chemopreventive properties. Cancer Chemother. Pharmacol 60, 257-266.
Cai, H., Hudson, E. A., Mann, P., Verschoyle, R. D., Greaves, P., Manson, M. M., Steward, W. P., Gescher, A. J., 2004. 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, 1364-1371.
Cai, H., Sale, S., Schmid, R., Britton, R. G., Brown, K., Steward, W. P., Gescher, A. J., 2009. Flavones as colorectal cancer chemopreventive agents--phenol-o-methylation enhances efficacy. Cancer Prev Res 2, 743-750.
Cai, H., Steward, W. P., Gescher, A. J., 2005b. Determination of the putative cancer chemopreventive flavone tricin in plasma and tissues of mice by HPLC with UV–visible detection. Biomed. Chromatogr. 19, 518-522.
Cai, H., Verschoyle, R. D., Steward, W. P., Gescher, A. J., 2003. Determination of the ﬂavone tricin in human plasma by high-performance liquid chromatography. Biomed. Chromatogr. 17, 435-439.
Cavalière, C., Foglia, P., Pastorini, E., Samperi, R., Lagana, A., 2005. Identification and mass spectrometric characterization of glycosylated flavonoids in Triticum durum plants by high-performance liquid chromatography with tandem mass spectrometry. Rapid Commun Mass Spectrom 19, 3143-3158.
Chan, W. L., Lin, Y. C., Zhang, W. H., Tang, P. L., Szeto, Y. S., 1996. One-step synthesis of polyhydroxyflavanones from hydroxyacetophenones and hydroxybenzaldehydes. ChemInform 27.
Chang, C.-L., Wang, G.-J., Zhang, L.-J., Tsai, W.-J., Chen, R.-Y., Wu, Y.-C., Kuo, Y.-H., 2010. Cardiovascular protective flavonolignans and flavonoids from Calamus quiquesetinervius. Phytochemistry 71, 271-279.
Chiwocha, S. D. S., Abrams, S. R., Ambrose, S. J., Cutler, A. J., Loewen, M., Ross, A. R. S., Kermode, A. R., 2003. A method for profiling classes of plant hormones and their metabolites using liquid chromatography-electrospray ionization tandem mass spectrometry: an analysis of hormone regulation of thermodormancy of lettuce (Lactuca sativa L.) seeds. The Plant Journal 35, 405-417.
Chung, I.-M., Hahn, S.-J., Ahmad, A., 2005. Confirmation of potential herbicidal agents in hulls of rice, Oryza sativa. J Chem Ecol 31, 1339-1352.
Cleveland, L. E., Moshfegh, A. J., Albertson, A. M., Goldman, J. D., 2000. Dietary intake of whole grains. J Am Coll Nutr 19, 331S-338S.
Colombo, R., Yariwake, J. H., Queiroz, E. F., Ndjoko, K., Hostettmann, K., 2006. On-line identiﬁcation of further flavone C- and O-glycosides from sugarcane (Saccharum ofﬁcinarum L., Gramineae) by HPLC-UV-MS. Phytochem Anal 17, 337-343.
Cook, D., Fowler, S., Fiehn, O., Thomashow, M. F., 2004. A prominent role for the CBF cold response pathway in configuring the low-temperature metabolome of Arabidopsis. Proc. Natl. Acad. Sci. USA 101, 15243-15248.
Cotter, R. J., 2004. Time-of-flight mass spectrometry. Encyclopedia of Genetics, Genomics, Proteomics and Bioinformatics. John Wiley & Sons, Ltd.
Craig, W. J., 1999. Health-promoting properties of common herbs. Am J Clin Nutr 70, 491S-499S.
Cummins, I., Brazier-Hicks, M., Stobiecki, M., Franski, R., Edwards, R., 2006. Selective disruption of wheat secondary metabolism by herbicide safeners. Phytochemistry 67, 1722-1730.
Cushnie, T. P. T., Lamb, A. J., 2005. Antimicrobial activity of flavonoids. Int. J. Antimicrob. Agents 26, 343-356.
David W.M, L., 1992. Involvement of plant chitinase in sexual reproduction of higher plants. Phytochemistry 31, 1899-1900.
Davies, J., Caseley, J. C., 1999. Herbicide safeners: a review. Pestic Sci 55, 1043-1058.
Deng, D., Zhang, J., Cooney, J. M., Skinner, M. A., Adaim, A., Jensen, D. J., Stevenson, D. E., 2006. Methylated polyphenols are poor (chemical) antioxidants but can still effectively protect cells from hydrogen peroxide-induced cytotoxicity. FEBS letters 580, 5247-5250.
Dhingra, D., Michael, M., Rajput, H., Patil, R., 2011. Dietary fibre in foods: a review. J Food Sci Technol 48,1-12.
Dixon, R. A., Paiva, N. L., 1995. Stress-Induced Phenylpropanoid Metabolism. Plant Cell 7, 1085-1097.
Dreyer, D. L., Jones, K. C., 1981. Feeding deterrency of flavonoids and related phenolics towards Schizaphis graminum and Myzus persicae: Aphid feeding deterrents in wheat. Phytochemistry 20, 2489-2493.
Du, Y., Chu, H., Wang, M., Chu, I. K., Lo, C., 2009. Identification of flavone phytoalexins and a pathogen-inducible flavone synthase II gene (SbFNSII) in sorghum. J Exp Bot 61, 983-994.
Duarte-Almeida, J. M., Negri, G., Salatino, A., de Carvalho, J. E., Lajolo, F. M., 2007. Antiproliferative and antioxidant activities of a tricin acylated glycoside from sugarcane (Saccharum officinarum) juice. Phytochemistry 68, 1165-1171.
Duarte Silva, I., Gaspar, J., Gomes da Costa, G., Rodrigues, A. S., Laires, A., Rueff, J., 2000. Chemical features of flavonols affecting their genotoxicity. Potential implications in their use as therapeutical agents. Chem. Biol. Interact. 124, 29-51.
Dykes L., R. L. W., 2007. Phenolic compounds in cereal grains and their health benefits
Cereal Food World 52, 105-111
Estiarte, M., Peñuelas, J., Kimball, B. A., Hendrix, D. L., Pinter Jr, P. J., Wall, G. W., LaMorte, R. L., Hunsaker, D. J., 1999. Free-air CO2 enrichment of wheat: leaf flavonoid concentration throughout the growth cycle. Physiologia Plantarum 105, 423-433.
Farmer, M. J., Czernic, P., Michael, A., Negrel, J., 1999. Identification and characterization of cDNA clones encoding hydroxycinnamoyl-CoA:tyramine N-hydroxycinnamoyltransferase from tobacco. Eur J Biochem 263, 686-694.
Fecht-Christoffers, M. M., Braun, H. P., Lemaitre-Guillier, C., VanDorsselaer, A., Horst, W. J., 2003. Effect of manganese toxicity on the proteome of the leaf apoplast in cowpea. Plant Physiol 133, 1935-1946.
Feng, Y., McDonald, C. E., 1989. Comparison of flavonoids in bran of four classes of wheat. Cereal Chem 66, 516-518.
Fixon-Owoo, S., Levasseur, F., Williams, K., Sabado, T. N., Lowe, M., Klose, M., Joffre Mercier, A., Fields, P., Atkinson, J., 2003. Preparation and biological assessment of hydroxycinnamic acid amides of polyamines. Phytochemistry 63, 315-334.
Floerl, S., Druebert, C., Majcherczyk, A., Karlovsky, P., Kues, U., Polle, A., 2008. Defence reactions in the apoplastic proteome of oilseed rape (Brassica napus var. napus) attenuate Verticillium longisporum growth but not disease symptoms. BMC Plant Biol 8, 129.
Food Directorate Guideline No. 9, Policy respecting dietary fibre in meal replacements In: Heatlth Canada, Nutrition, F. a. (Eds.) 1993.
Forkmann, G., Heller, W., 1999. Biosynthesis of flavonoids. In: Sankawa., U. (Ed.), Comprehensive Natural Products Chemistry, vol. 1. Elsevier, Amsterdam, 714-748
Fowler, D. B., 2008. Cold acclimation threshold induction temperatures in cereals. Crop Sci. 48, 1147-1154.
Galeotti, F., Barile, E., Curir, P., Dolci, M., Lanzotti, V., 2008. Flavonoids from carnation (Dianthus caryophyllus) and their antifungal activity. Phytochemistry Letters 1, 44-48.
García-Mediavilla, V., Crespo, I., Collado, P. S., Esteller, A., Sánchez-Campos, S., Tuñón, M. J., González-Gallego, J., 2007. The anti-inflammatory flavones quercetin and kaempferol cause inhibition of inducible nitric oxide synthase, cyclooxygenase-2 and reactive C-protein, and down-regulation of the nuclear factor kappa B pathway in chang liver cells. Eur. J. Pharmacol. 557, 221-229.
Gicquiaud, L., Hennion, F., Esnault, M. A., 2002. Physiological comparisons among four related bromus species with varying ecological amplitude: polyamine and aromatic amine aomposition in response to salt spray and drought. Plant Biology 4, 746-753.
Gould, K., Lister, C., 2005. Flavonoid functions in plants. Flavonoids. CRC Press, 397-441.
Gray, G. R., Heath, D., 2005. A global reorganization of the metabolome in Arabidopsis during cold acclimation is revealed by metabolic fingerprinting. Physiologia Plantarum 124, 236-248.
Griffith, M., Huner, N. P. A., Espelie, K. E., Kolattukudy, P. E., 1985. Lipid polymers accumulate in the epidermis and mestome sheath cell walls during low temperature development of winter rye leaves. Protoplasma 125, 53-64.
Griffith, M., Yaish, M. W., 2004. Antifreeze proteins in overwintering plants: a tale of two activities. Trends Plant Sci. 9, 399-405.
Grondin, M., Hamel, F., Sarhan, F., Averill-Bates, D. A., 2008. Metabolic activity of cytochrome p450 isoforms in hepatocytes cryopreserved with wheat protein extract. Drug Metab Dispos 36, 2121-2129.
Hahlbrock, K., Scheel, D., 1989. Physiology and molecular biology of phenylpropanoid metabolism. Annu Rev Plant Physiol Plant Mol Biol 40, 347-369.
Harborne, J. B., 1967. Comparative biochemistry of the flavonoids-VI. : Flavonoid patterns in the bignoniaceae and the gesneriaceae. Phytochemistry 6, 1643-1651.
Harborne, J. B., 1988. Plant flavonoids in biology and medicine II. Biochemical, cellular, and medicinal properties Alan R. Liss Publisher, pp. 17-27.
Harborne, J. B., Hall, E., 1964. Plant polyphenols--XII. : The occurrence of tricin and of glycoflavones in grasses. Phytochemistry 3, 421-428.
Harborne, J. B., Williams, C. A., 1969. The identification of orcinol in higher plants in the family ericaceae. Phytochemistry 8, 2223-2226.
Harborne, J. B., Williams, C. A., 1976. Flavonoid patterns in leaves of the Gramineae. Biochem. Syst. Ecol. 4, 267-280.
Hasegawa, T., Tanaka, A., Hosoda, A., Takano, F., Ohta, T., 2008. Antioxidant C-glycosyl flavones from the leaves of Sasa kurilensis var. gigantea. Phytochemistry 69, 1419-1424.
Hatfield, R., Vermerris, W., 2001. Lignin formation in plants. The dilemma of linkage specificity. Plant Physiol 126, 1351-1357
Henderson, B., 1984. Quantitative cytochemistry of lactate dehydrogenase activity.Cell Biochem. Funct. 2, 149-152.
Hertog, M. l. G. L., Hollman, P. C. H., Katan, M. B., Kromhout, D., 1993. Intake of potentially anticarcinogenic flavonoids and their determinants in adults in the Netherlands. Nutr and Cancer 20, 21-29.
HHS, USDA, 2005. Dietary Guidelines for Americans. http:www.health.gov/dietarvnuidelines/dga2005. The U.S. Department of Health and Human Services, 25-28.
Holden, J. M., Bhagwat, S. A., Haytowitz, D. B., Gebhardt, S. E., Dwyer, J. T., Peterson, J., Beecher, G. R., Eldridge, A. L., Balentine, D., 2005. Development of a database of critically evaluated flavonoids data: application of USDA's data quality evaluation system. J Food Comp Anal 18, 829-844.
Hua, S. S. T., Grosjean, O. K., Baker, J. L., 1999. Inhibition of aflatoxin biosynthesis by phenolic compounds. Lett Appl Microbiol 29, 289-291.
Hudson, E. A., Dinh, P. A., Kokubun, T., Simmonds, M. S., Gescher, A., 2000. 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, 1163-1170.
Huner NPA, P. J., Li PH, Carter JV., 1981. Anatomical changes in leaves of Puma rye in response to growth at cold-hardening temperatures. Bot. Gaz. 142, 55-62.
Ibrahim, R. K., 2001. Flavonoids. eLS. John Wiley & Sons, Ltd.
Ibrahim, R. K., Anzellotti, D., 2003. Chapter one: The enzymatic basis of flavonoid biodiversity. Recent Advances in Phytochemistry 37, 1-36.
Ibrahim, R. K., De Luca, V., Khouri, H., Latchinian, L., Brisson, L., Charest, P. M., 1987. Enzymology and compartmentation of polymethylated flavonol glucosides in chrysosplenium americanum. Phytochemistry 26, 1237-1245.
Ibrahim, R. K., Muzac, I., John T. Romeo, R. I. L. V., Vincenzo De, L., 2000. Chapter Eleven The methyltransferase gene superfamily: A tree with multiple branches. Recent Adv Phytochem 34 349-384.
Imin, N., Nizamidin, M., Wu, T., Rolfe, B. G., 2007. Factors involved in root formation in Medicago truncatula. J Exp Bot 58, 439-451.
Jacquemin, G., Shirley, S., Micheau, O., 2010. Combining naturally occurring polyphenols with TNF-related apoptosis-inducing ligand: a promising approach to kill resistant cancer cells? Cell Mol Life Sci 67, 3115-3130.
Jeong, Y. H., Chung, S. Y., Han, A. R., Sung, M. K., Jang, D. S., Lee, J., Kwon, Y., Lee, H. J., Seo, E. K., 2007. P-glycoprotein inhibitory activity of two phenolic compounds, (-)-syringaresinol and tricin from Sasa borealis. Chem Biodivers 4, 12-16.
Jiao, J., Zhang, Y., Liu, C., Liu, J. e., Wu, X., Zhang, Y., 2007. Separation and purification of tricin from an antioxidant product derived from Bamboo leaves. J Agric Food Chem 55, 10086-10092.
Jin, S., Yoshida, M., 2000. Antifungal compound, feruloylagmatine, induced in winter wheat exposed to a low temperature. Biosci Biotechnol Biochem 64, 1614-1617.
Jun-Ping, K., Ling-Li, M., 2008. Antioxidant activi
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