Phenolic Compounds in Brassica Vegetables
Tóm tắt
Phenolic compounds are a large group of phytochemicals widespread in the plant kingdom. Depending on their structure they can be classified into simple phenols, phenolic acids, hydroxycinnamic acid derivatives and flavonoids. Phenolic compounds have received considerable attention for being potentially protective factors against cancer and heart diseases, in part because of their potent antioxidative properties and their ubiquity in a wide range of commonly consumed foods of plant origin. The Brassicaceae family includes a wide range of horticultural crops, some of them with economic significance and extensively used in the diet throughout the world. The phenolic composition of Brassica vegetables has been recently investigated and, nowadays, the profile of different Brassica species is well established. Here, we review the significance of phenolic compounds as a source of beneficial compounds for human health and the influence of environmental conditions and processing mechanisms on the phenolic composition of Brassica vegetables.
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Tài liệu tham khảo
Podsedek, 2007, Natural antioxidants and antioxidant capacity of Brassica vegetables: A review, Lwt-Food Sci. Technol., 40, 1, 10.1016/j.lwt.2005.07.023
Jahangir, 2009, Health-Affecting Compounds in Brassicaceae, Compr. Rev. Food Sci. Food Saf., 8, 31, 10.1111/j.1541-4337.2008.00065.x
Crozier, A., Clifford, M., and Ashihara, H. (2006). Plant Secondary Metabolites: Occurrence, Structure and Role in the Human Diet, Blackwell.
Hollman, 2000, Flavonols, flavones and flavanols - nature, occurrence and dietary burden, J. Sci. Food Agric., 80, 1081, 10.1002/(SICI)1097-0010(20000515)80:7<1081::AID-JSFA566>3.0.CO;2-G
Aron, 2008, Flavan-3-ols: Nature, occurrence and biological activity, Mol. Nutr. Food Res., 52, 79, 10.1002/mnfr.200700137
Sadilova, 2006, Anthocyanins, colour and antioxidant properties of eggplant (Solanum melongena L.) and violet pepper (Capsicum annuum L.) peel extracts, Z. Naturforsch. C, 61, 527, 10.1515/znc-2006-7-810
McDougall, 2007, Anthocyanins from red cabbage - stability to simulated gastrointestinal digestion, Phytochemistry, 68, 1285, 10.1016/j.phytochem.2007.02.004
Moreno, 2010, Acylated anthocyanins in broccoli sprouts, Food Chem., 123, 358, 10.1016/j.foodchem.2010.04.044
Agati, 2010, Multiple functional roles of flavonoids in photoprotection, New Phytol., 186, 786, 10.1111/j.1469-8137.2010.03269.x
Tatsuzawa, 2006, Acylated cyanidin 3-sambubioside-5-glucosides in three garden plants of the Cruciferae, Phytochemistry, 67, 1287, 10.1016/j.phytochem.2006.05.001
Genna, 2008, Anthocyanin composition of cauliflower (Brassica oleracea L. var. botrytis) and cabbage (B. oleracea L. var. capitata) and its stability in relation to thermal treatments, Food Chem., 107, 136, 10.1016/j.foodchem.2007.07.072
Vallejo, 2004, Characterisation of flavonols in broccoli (Brassica oleracea L. var. italica) by liquid chromatography-UV diode-array detection-electrospray ionisation mass spectrometry, J. Chromatogr., 1054, 181, 10.1016/j.chroma.2004.05.045
Olsen, 2009, Characterization and Quantification of Flavonoids and Hydroxycinnamic Acids in Curly Kale (Brassica oleracea L. convar. acephala var. sabellica) by HPLC-DAD-ESI-MSn, J. Agric. Food Chem., 57, 2816, 10.1021/jf803693t
Lin, 2010, Phenolic Component Profiles of Mustard Greens, Yu Choy, and 15 Other Brassica Vegetables, J. Agric. Food Chem., 58, 6850, 10.1021/jf1004786
Price, 1997, Hydroxycinnamic acid esters from broccoli florets, Phytochemistry, 45, 1683, 10.1016/S0031-9422(97)00246-X
Crozier, 2009, Dietary phenolics: Chemistry, bioavailability and effects on health, Nat. Prod. Rep., 26, 1001, 10.1039/b802662a
Vallejo, 2002, Potential bioactive compounds in health promotion from broccoli cultivars grown in Spain, J. Sci. Food Agric., 82, 1293, 10.1002/jsfa.1183
Moreno, 2010, Flavanols and Anthocyanins in Cardiovascular Health: A Review of Current Evidence, Int. J. Mol. Sci., 11, 1679, 10.3390/ijms11041679
Plumb, 1997, Antioxidant properties of the major polyphenolic compounds in broccoli, Free Radical Res., 27, 429, 10.3109/10715769709065782
Cushnie, 2005, Antimicrobial activity of flavonoids, Int. J. Antimicrob. Agents, 26, 343, 10.1016/j.ijantimicag.2005.09.002
Chu, 2000, Flavonoid content of several vegetables and their antioxidant activity, J. Sci. Food Agric., 80, 561, 10.1002/(SICI)1097-0010(200004)80:5<561::AID-JSFA574>3.0.CO;2-#
Podsedek, 2006, Antioxidant capacity and content of Brassica oleracea dietary antioxidants, Int. J. Food Sci. Technol., 41, 49, 10.1111/j.1365-2621.2006.01260.x
Fukumoto, 2000, Assessing antioxidant and prooxidant activities of phenolic compounds, J. Agric. Food Chem., 48, 3597, 10.1021/jf000220w
Skandrani, 2010, Assessment of phenolic content, free-radical-scavenging capacity genotoxic and anti-genotoxic effect of aqueous extract prepared from Moricandia arvensis leaves, Food Chem. Toxicol., 48, 710, 10.1016/j.fct.2009.11.053
Ackland, 2005, Synergistic antiproliferative action of the flavonols quercetin and kaempferol in cultured human cancer cell lines, In Vivo, 19, 69
Fresco, 2010, The Anticancer Properties of Dietary Polyphenols and its Relation with Apoptosis, Curr. Pharm. Des., 16, 114, 10.2174/138161210789941856
Shen, 2010, ABCG2 reduces ROS-mediated toxicity and inflammation: A potential role in Alzheimer's disease, J. Neurochem., 114, 1590, 10.1111/j.1471-4159.2010.06887.x
Mullen, 2007, Evaluation of phenolic compounds in commercial fruit juices and fruit drinks, J. Agric. Food Chem., 55, 3148, 10.1021/jf062970x
Llorach, 2003, Valorization of cauliflower (Brassica oleracea L. var. botrytis) by-products as a source of antioxidant phenolics, J. Agric. Food Chem., 51, 2181, 10.1021/jf021056a
Kim, 2006, Chemical structure of flavonols in relation to modulation of angiogenesis and immune-endothelial cell adhesion, J. Nutr. Biochem., 17, 165, 10.1016/j.jnutbio.2005.06.006
Jung, 2007, Acetylcholinesterase inhibition by flavonoids from agrimonia pilosa, Molecules, 12, 2130, 10.3390/12092130
Braca, 2003, Antioxidant and free radical scavenging activity of flavonol glycosides from different Aconitum species, J. Ethnopharmacol., 86, 63, 10.1016/S0378-8741(03)00043-6
Ayaz, 2008, Phenolic acid contents of kale (Brassica oleraceae L. var. acephala DC.) extracts and their antioxidant and antibacterial activities, Food Chem., 107, 19, 10.1016/j.foodchem.2007.07.003
Yokozawa, 2002, Antioxidant Effects of isorhamnetin 3,7-Di-O-β-d-glucopyranoside isolated from mustard leaf (Brassica juncea) in Rats with Streptozotocin-Induced Diabetes, J. Agric. Food. Chem., 50, 5490, 10.1021/jf0202133
Guillamon, 2009, Flavonoids as anti-inflammatory agents: Implications in cancer and cardiovascular disease, Inflammation Res., 58, 537, 10.1007/s00011-009-0037-3
Baumert, 2007, Genetic variation for sinapate ester content in winter rapeseed (Brassica napus L.) and development of NIRS calibration equations, Plant Breed., 126, 291, 10.1111/j.1439-0523.2007.01342.x
Auger, 2010, A Detailed survey of seed coat flavonoids in developing seeds of Brassica napus L, J. Agric. Food Chem., 58, 6246, 10.1021/jf903619v
Scalbert, 2000, Dietary intake and bioavailability of polyphenols, J. Nutr., 130, 2073S, 10.1093/jn/130.8.2073S
Zhao, 2010, Bioavailability of hydroxycinnamates: A brief review of in vivo and in vitro studies, Phytochem. Rev., 9, 133, 10.1007/s11101-009-9145-5
Filesi, 2010, Bioavailability of the Polyphenols: Status and Controversies, Int. J. Mol. Sci., 11, 1321, 10.3390/ijms11041321
Murota, 2003, Antioxidative flavonoid quercetin: Implication of its intestinal absorption and metabolism, Arch. Biochem. Biophys., 417, 12, 10.1016/S0003-9861(03)00284-4
Silberberg, 2006, The bioavailability of polyphenols is highly governed by the capacity of the intestine and of the liver to secrete conjugated metabolites, Eur. J. Nutr., 45, 88, 10.1007/s00394-005-0568-5
Wittemer, 2005, Bioavailability and pharmacokinetics of caffeoylquinic acids and flavonoids after oral administration of Artichoke leaf extracts in humans, Phytomedicine, 12, 28, 10.1016/j.phymed.2003.11.002
Moreno, 2006, Chemical and biological characterisation of nutraceutical compounds of broccoli, J. Pharm. Biomed. Anal., 41, 1508, 10.1016/j.jpba.2006.04.003
Bahorun, 2004, Total phenol, flavonoid, proanthocyanidin and vitamin C levels and antioxidant activities of Mauritian vegetables, J. Sci. Food Agric., 84, 1553, 10.1002/jsfa.1820
Harbaum, 2007, Identification of flavonolds and hydroxycinnamic acids in pak choi varieties (Brassica campestris L. ssp chinensis var. communis) by HPLC-ESI-MSn and NMR and their quantification by HPLC-DAD, J. Agric. Food Chem., 55, 8251, 10.1021/jf071314+
Ferreres, 2005, Phenolic compounds in external leaves of tronchuda cabbage (Brassica oleracea L. var. costata DC), J. Agric. Food Chem., 53, 2901, 10.1021/jf040441s
Llorach, 2003, HPLC-DAD-MS/MS ESI characterization of unusual highly glycosylated acylated flavonoids from cauliflower (Brassica oleracea L. var. botrytis) agroindustrial byproducts, J. Agric. Food Chem., 51, 3895, 10.1021/jf030077h
Gil, 2008, A comparative study of flavonoid compounds, vitamin C, and antioxidant properties of baby leaf Brassicaceae species, J. Agric. Food Chem., 56, 2330, 10.1021/jf072975+
Nielsen, 1998, Kaempferol tetraglucosides from cabbage leaves, Phytochemistry, 49, 2171, 10.1016/S0031-9422(98)00422-1
Price, 1998, Composition and content of flavonol glycosides in broccoli florets (Brassica oleracea) and their fate during cooking, J. Sci. Food Agric., 77, 468, 10.1002/(SICI)1097-0010(199808)77:4<468::AID-JSFA66>3.0.CO;2-B
Romani, 2003, Flavonoids in leaves of black cabbage (Brassica oleracea var. acephala DC. subvar. viridis cv. serotina) grown on different soils and at different elevations, Ital. J. Food Sci., 15, 197
Fernandes, 2007, Chemical and antioxidative assessment of dietary turnip (Brassica rapa var. rapa L.), Food Chem., 105, 1003, 10.1016/j.foodchem.2007.04.063
Francisco, 2009, Simultaneous identification of glucosinolates and phenolic compounds in a representative collection of vegetable Brassica rapa, J. Chromatogr., 1216, 6611, 10.1016/j.chroma.2009.07.055
Velasco, P., Francisco, M., Moreno, D.A., Ferreres, F., García-Viguera, C., and Cartea, M.E. (2010). Phytochemical fingerprinting of vegetable Brassica oleracea and Brassica napus by simultaneous identification of glucosinolates and phenolics. Phytochemical Analysis (in press).
Nielsen, 1993, Acylated flavonol glycosides from cabbage leaves, Phytochemistry, 34, 539, 10.1016/0031-9422(93)80042-Q
Ferreres, 2006, Chemical composition and antioxidant activity of tronchuda cabbage internal leaves, Eur. Food Res. Technol., 222, 88, 10.1007/s00217-005-0104-0
Martinez, 2010, Quality parameters of Brassica spp. grown in northwest Spain, Int. J. Food Sci. Technol., 45, 776, 10.1111/j.1365-2621.2010.02198.x
Sousa, 2005, Influence of two fertilization regimens on the amounts of organic acids and phenolic compounds of tronchuda cabbage (Brassica oleracea L. var. costata DC), J. Agric. Food Chem., 53, 9128, 10.1021/jf051445f
Sousa, 2007, Screening of antioxidant compounds during sprouting of Brassica oleracea L. var. costata DC, Comb. Chem. High Throughput Scr., 10, 377, 10.2174/138620707781662817
Sousa, 2008, Inflorescences of Brassicaceae species as source of bioactive compounds: A comparative study, Food Chem., 110, 953, 10.1016/j.foodchem.2008.02.087
Vallejo, 2003, Health-promoting compounds in broccoli as influenced by refrigerated transport and retail sale period, J. Agric. Food Chem., 51, 3029, 10.1021/jf021065j
Castellari, 2010, Simultaneous evaluation of intact glucosinolates and phenolic compounds by UPLC-DAD-MS/MS in Brassica oleracea L. var. botrytis, Food Chem., 121, 257, 10.1016/j.foodchem.2009.11.081
Heimler, 2006, Antiradical activity and polyphenol composition of local Brassicaceae edible varieties, Food Chem., 99, 464, 10.1016/j.foodchem.2005.07.057
Ferreres, 2009, Screening of antioxidant phenolic compounds produced by in vitro shoots of Brassica oleracea L. var. costata DC, Comb. Chem. High Throughput Scr., 12, 230, 10.2174/138620709787581756
Taveira, 2009, In Vitro Cultures of Brassica oleracea L. var. costata DC: Potential Plant Bioreactor for Antioxidant Phenolic Compounds, J. Agric. Food Chem., 57, 1247, 10.1021/jf803496x
Wu, 2005, Identification and characterization of anthocyanins by high-performance liquid chromatography-electrospray ionization-tandem mass spectrometry in common foods in the United States: Vegetables, nuts, and grains, J. Agric. Food Chem., 53, 3101, 10.1021/jf0478861
Vallejo, 2003, Changes in broccoli (Brassica oleracea L. var. italica) health-promoting compounds with inflorescence development, J. Agric. Food Chem., 51, 3776, 10.1021/jf0212338
Harbaum, 2008, Free and bound phenolic compounds in leaves of pak choi (Brassica campestris L. ssp chinensis var. communis) and Chinese leaf mustard (Brassica juncea Coss), Food Chem., 110, 838, 10.1016/j.foodchem.2008.02.069
Romani, 2006, HPLC-DAD/MS characterization of flavonoids and hydroxycinnamic derivatives in turnip tops (Brassica rapa L. subsp sylvestris L.), J. Agric. Food Chem., 54, 1342, 10.1021/jf052629x
Ferreres, 2008, HPLC-DAD-MS/MS-ESI screening of phenolic compounds in Pieris brassicae L. reared on Brassica rapa var. rapa L, J. Agric. Food Chem., 56, 844, 10.1021/jf072657a
Trokowski, 2010, Determination of Antioxidant Capacity, Phenolic Acids, and Fatty Acid Composition of Rapeseed Varieties, J. Agric. Food Chem., 58, 7502, 10.1021/jf100852x
Khattab, 2010, Determination of Sinapic Acid Derivatives in Canola Extracts Using High-Performance Liquid Chromatography, J. Am. Oil Chem. Soc., 87, 147, 10.1007/s11746-009-1486-0
Li, 2010, Purple Canola: Arabidopsis PAP1 Increases Antioxidants and Phenolics in Brassica napus Leaves, J. Agric. Food Chem., 58, 1639, 10.1021/jf903527y
Harbaum, 2008, Impact of fermentation on phenolic compounds in leaves of pak choi (Brassica campestris L. ssp chinensis var. communis) and Chinese leaf mustard (Brassica juncea coss), J. Agric. Food Chem., 56, 148, 10.1021/jf072428o
Fang, 2008, Changes of phenolic acids and antioxidant activities during potherb mustard (Brassica juncea, Coss.) pickling, Food Chem., 108, 811, 10.1016/j.foodchem.2007.11.033
U, 1935, Genome analysis in Brassica with special reference to the experimental formation of B. napus and peculiar mode of fertilization, Jpn. J. Bot., 7, 389
Aguinagalde, 1992, A chemosystematic survey on wild relatives of Brassica oleracea L, Bot. J. Linn. Soc., 109, 57, 10.1111/j.1095-8339.1992.tb00258.x
Braham, 2005, Antioxidant phenolic glycosides from Moricandia arvensis, J. Nat. Prod., 68, 517, 10.1021/np049581m
Weckerle, 2001, Quercetin 3,3 ',4 '-tri-O-beta-D-glucopyranosides from leaves of Eruca sativa (Mill.), Phytochemistry, 57, 547, 10.1016/S0031-9422(01)00059-0
Bennett, 2006, Ontogenic profiling of glucosinolates, flavonoids, and other secondary metabolites in Eruca sativa (salad rocket), Diplotaxis erucoides (wall rocket), Diplotaxis tenuifolia (wild rocket), and Bunias orientalis (Turkish rocket), J. Agric. Food Chem., 54, 4005, 10.1021/jf052756t
Llorach, 2007, Identification of new flavonoid glycosides and flavonoid profiles to characterize rocket leafy salads (Eruca vesicaria and Diplotaxis tenuifolia), J. Agric. Food Chem., 55, 1356, 10.1021/jf063474b
Onyilagha, 2003, Leaf flavonoids of the cruciferous species, Camelina sativa, Crambe sp. Thlaspi arvense and several other genera of the family Brassicaceae, Biochem. Syst. Ecol., 31, 1309, 10.1016/S0305-1978(03)00074-7
Francisco, 2010, Cooking methods of Brassica rapa affect the preservation of glucosinolates, phenolics and vitamin C, Food Res. Int., 43, 1455, 10.1016/j.foodres.2010.04.024
2008, Effect of hydrothermal treatment on the antioxidant properties of broccoli (Brassica oleracea var. botrytis italica) florets, Food Chem., 109, 393, 10.1016/j.foodchem.2007.12.058
Maggio, 2007, Sulphur fertilization may improve the nutritional value of Brassica rapa L. subsp sylvestris, Eur. J. Agron., 26, 418, 10.1016/j.eja.2006.12.009
Li, 2008, Effects of nitrogen and sulfur on total phenolics and antioxidant activity in two genotypes of leaf mustard, J. Plant Nutr., 31, 1642, 10.1080/01904160802244860
Vallejo, 2003, Effect of climatic and sulphur fertilisation conditions, on phenolic compounds and vitamin C, in the inflorescences of eight broccoli cultivars, Eur. Food Res. Technol., 216, 395, 10.1007/s00217-003-0664-9
Zhao, 2009, Comparison of phenolic acids in organically and conventionally grown pak choi (Brassica rapa L. chinensis), J. Sci. Food Agric., 89, 940, 10.1002/jsfa.3534
Young, 2005, Phytochemical phenolics in organically grown vegetables, Mol. Nutr. Food Res., 49, 1136, 10.1002/mnfr.200500080
Podsedek, 2008, Effect of domestic cooking on the red cabbage hydrophilic antioxidants, Int. J. Food Sci. Technol., 43, 1770, 10.1111/j.1365-2621.2007.01697.x
Zhang, 2004, Phenolics, ascorbic acid, carotenoids and antioxidant activity of broccoli and their changes during conventional and microwave cooking, Food Chem., 88, 503, 10.1016/j.foodchem.2004.01.065
Vallejo, 2003, Phenolic compound contents in edible parts of broccoli inflorescences after domestic cooking, J. Sci. Food Agric., 83, 1511, 10.1002/jsfa.1585
Lin, 2005, Textural change and antioxidant properties of broccoli under different cooking treatments, Food Chem., 90, 9, 10.1016/j.foodchem.2004.02.053
Sultana, 2008, Effect of different cooking methods on the antioxidant activity of some vegetables from Pakistan, Int. J. Food Sci. Technol., 43, 560, 10.1111/j.1365-2621.2006.01504.x
Ciska, 2006, Changes in the content of health-promoting compounds and antioxidant activity of broccoli after domestic processing, Food Addit. Contam., 23, 1088, 10.1080/02652030600887594
Natella, 2010, Microwave and traditional cooking methods: Effect of cooking on antioxidant capacity and phenolic compounds content of seven vegetables, J. Food Biochem., 34, 796
Starzynska, 2003, Physiological changes in the antioxidant system of broccoli flower buds senescing during short-term storage, related to temperature and packaging, Plant Sci., 165, 1387, 10.1016/j.plantsci.2003.07.004
Meyer, 1987, A new petunia flower color generated by transformation of a mutant with a maize gene, Nature, 330, 677, 10.1038/330677a0
Jung, 2000, Identification and expression of isoflavone synthase, the key enzyme for biosynthesis of isoflavones in legumes (vol 18, pg 211, 2000), Nat. Biotechnol., 18, 559, 10.1038/72671
Schijlen, 2004, Modification of flavonoid biosynthesis in crop plants, Phytochemistry, 65, 2631, 10.1016/j.phytochem.2004.07.028
Husken, 2005, Reduction of sinapate ester content in transgenic oilseed rape (Brassica napus) by dsRNAi-based suppression of BnSGT1 gene expression, Mol. Breed., 16, 127, 10.1007/s11032-005-6825-8
Milkowski, 2010, Sinapate esters in brassicaceous plants: Biochemistry, molecular biology, evolution and metabolic engineering, Planta, 232, 19, 10.1007/s00425-010-1168-z
Velasco, 1998, Nondestructive assessment of sinapic acid esters in Brassica species: II. Evaluation of germplasm and identification of phenotypes with reduced levels, Crop Sci., 38, 1650, 10.2135/cropsci1998.0011183X003800060039x
Nair, 2000, Identification of a CYP84 family of cytochrome P450-dependent mono-oxygenase genes in Brassica napus and perturbation of their expression for engineering sinapine reduction in the seeds, Plant Physiol., 123, 1623, 10.1104/pp.123.4.1623