Onions: A source of unique dietary flavonoids

Journal of Agricultural and Food Chemistry

Volumn 55, Issue 25, 2007, Pages 10067-10080

  Slimestad, Rune ^a   Fossen, Torgils ^b   Vågen, Ingunn Molund ^c  

^a PlantChem   (Norway)

^b UNIVERSITY OF BERGEN   (Norway)

^c NORWEGIAN INSTITUTE OF BIOECONOMY RESEARCH   (Norway)

Author keywords

Allium cepa; Anthocyanins; Cultivars; Dihydroflavonols; Flavonoids; Flavonols; NMR; Onion; Quantitative content

Indexed keywords

ANTHOCYANIN; FLAVONOID; FLAVONOL DERIVATIVE; QUERCETIN;

CHEMISTRY; COMPARATIVE STUDY; DIET; GLYCOSYLATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ONION; PIGMENTATION; PLANT ROOT; REVIEW; SPECIES DIFFERENCE;

ANTHOCYANINS; DIET; FLAVONOIDS; FLAVONOLS; GLYCOSYLATION; MAGNETIC RESONANCE SPECTROSCOPY; ONIONS; PIGMENTATION; PLANT ROOTS; QUERCETIN; SPECIES SPECIFICITY;

ALLIUM ATRORUBENS; ALLIUM CEPA;

EID: 38049085684     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0712503     Document Type: Review

References (100)

1. Middleton, E., Jr.; Kandaswami, C.; Theoharides, T.C. The effects of plant flavonoids on mammalian cells: implications for inflammation, heart disease, and cancer. Pharmacol. Rev. 2000, 52, 673-751.
2. Okamoto, T. Safety of quercetin for clinical application (Review). Int. J. Mol. Med. 2005, 16, 275-278.
3. Brewster, J. L. Onions and other vegetable Alliums. CAB International, Oxon, U.K., 1994; pp 1-236.
4. Harborne, J. B. In Natural Products. Their chemistry and biological significance; Mann, J., Davidson, R. S., Hobbs, J. B., Banthorpe, D. V., Harborne, J. B., Eds.; Longman Scientific & Technical: Essex, England, 1994, p 372.
5. Masuzaki, S.; Shigyo, M.; Yamauchi, N. Complete assignment of structural genes involved in flavonoid biosynthesis influencing bulb color to individual chromosomes of the shallot (Allium cepa L.). Genes Genet. Syst. 2006, 81, 255-263.
6. Masuzaki, S.; Shigyo, M.; Yamauchi, N. Direct comparison between genomic constitution and flavonoid content in Allium multiple alien addition lines reveals chromosomal locations of genes related to biosynthesis from dihydrokaempferol to quercetin glucosides in scaly leaf of shallot (Allium cepa L.). Theor. Appl. Genet. 2006, 112, 607-617.
7. Kim, S.; Bang, H.; Yoo, K.-S.; Pike, L. M. Identification of the fourth allele of the ANS (anthocyanidin synthase) gene and its effect on red color intensity in onions (Allium cepa). Euphytica 2006, 149, 45-51.
8. Takahama, U.; Hirota, S. Deglucosidation of quercetin glucosides to the aglycone and formation of antifungal agents by peroxidase-dependent oxidation of quercetin on browning of onion scales. Plant Cell Physiol. 2000, 41, 1021-1029.
9. Hirota, S.; Shimoda, T.; Takahama, U. Tissue and spatial distribution of flavonol and peroxidase in onion bulbs and stability of flavonol glucosides during boiling of the scales. J. Agric. Food Chem. 1998, 46, 3497-3502.
10. Griffiths, G.; Trueman, L.; Crowther, T.; Thomas, B.; Smith, B. Onions - a global benefit to health. Phytother. Res. 2002, 16, 603-615.
11. Herrmann, K. Review: On the occurrence of flavonol and flavone glycosides in vegetables. Z. Lebensm.-Unters. Forsch. 1988, 186, 1-5.
12. Lanzotti, V. Review: The analysis of onion and garlic. J. Chromatogr. A 2006, 1112, 3-22.
13. Fossen, T.; Andersen, Ø. M. Spectroscopic techniques applied to flavonoids. In Flavonoids. Chemistry, biochemistry and applications; Andersen, Ø. M., Markham, K. R., Eds.; CRC Taylor & Francis: Boca Raton, FL, 2006; pp 37-142.
14. Leuchs, E. F. Farben Farbenkünde 1825, 1, 434.
15. Perkin, A. G.; Hummel, J. J. Occurrence of quercetin in the outer skins of the bulb of the onion. J. Chem. Soc. 1896, 69, 1295-1298.
16. Herrmann, K. Quercetin glycosides of the onion (Allium cepa). Naturwissenschaften 1956, 43, 158.
17. Herrmann, K. Flavonols and phenols in onions (Allium cepa L.). Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1958, 291, 238-247.
18. Steinegger, E.; Casparis, P. Zur Frage der Konstitution des Spiraeosides. Pharm. Acta Helv. 1945, 20, 174-177.
19. Hörhammer, L.; Hansel, R. Über die Stellung der Glukose im Molekul des Spiraeosides. Arch. Pharm. Ber. Dtsch. Pharm. Ges. 1954, 287 (59), 36-38.
20. Koeppen, B. H.; Van der Spuy, J. E. Microbial hydrolysis of quercetin glycosides from the inner scales of the onion. S. Afr. J. Agric. Sci. 1961, 4, 557-563.
21. Brandwein, B. J. The pigments in three cultivars of the common onion (Allium cepa). J. Food Sci. 1965, 30, 680-685.
22. Harborne, J. B. Plant Polyphenols - XIV. Characterization of flavonoid glycosides by acidic and enzymatic hydrolyses. Phytochemistry 1965, 4, 107-120.
23. Bandyukova, V. A.; Shinkarenko, A. L. Isolation of polyphenol compounds from scales of Allium cepa. Farm. Zh. (Kiev) 1967, 22, 54-57.
24. Tronchet, J. Flavone derivatives of Allium cepa (straw onion). Nature, location and distribution in the bulb and the foliage during development. Ann. Sci. Univ. Besancon, Bot. 1971, 10, 13-22.
25. Smoczkiewiczowa, A.; Nitschke, D. Flawonoidy w Cebuli. Pol. Zesz. Nauk. Akad. Ekon. Pozaniu Ser. I: Prace Zakresu Towaroznawstwa i Chemii 1978, 73, 35-39.
26. Tsushida, T.; Suzuki, M. Isolation of flavonoid-glycosides in onion and identification by chemical synthesis of the glycosides. Nippon Shokuhin Kagaku Kaishi 1995, 42, 100-108.
27. Fossen, T.; Pedersen, A. T.; Andersen, Ø. M. Flavonoids from red onion (Allium cepa). Phytochemistry 1998, 47, 281-285.
28. Ttssut, M. La synthese flavonique dans les tuniques en survie de bulbe d'oignon. Physiol. Vég. 1972, 10, 381-391.
29. Panisset, B.; Tissut, M. Métabolisme des flavonols dans les tuniques isolées de huit variétés d'Oignon: effet d'un traitement par l'acide gibbérellique et l'aminozide. Physiol. Vég. 1983, 21, 49-57.
30. Fossen, T. Unpublished work, 2007.
31. Sood, A. R.; Joshi, K. K. Flavonoid components of Allium cepa. J. Indian Chem. Soc. 1974, 51, 975.
32. Scheer, T.; Wichtl, M. On the occurrence of Kaempferol-4′-O-β- D-glucopyranoside in F. ulmaria and A. cepa. Planta Med. 1987, 53, 573-574.
33. Park, Y.-K.; Lee, C. Y. Identification of isorhamnetin 4′-glucoside in onions. J. Agric. Food Chem. 1996, 44, 34-36.
34. Omidiji, O. Flavonol glycosides in the wet scale of the deep purple onion (Allium cepa L. cv. Red Creole). Discovery Innovation 1993, 5, 139-141.
35. Lachman, J.; Pronek, D.; Hejtmankova, A.; Dudjak, J.; Pivec, V.; Faitova, K. Total polyphenols and main flavonoid antioxidants in different onion (Allium cepa L.) cultivars. Hortic. Sci. (Prague) 2003, 30, 142-147.
36. Fel'dmann, A. L.; Gusar, Z. D.; Markh, A. T. Studies of flavonols and p-coumaric acid in different tissues of onions. Fiziol. Biokhim, Kul't. Rast. 1978, 10, 302-304.
37. Rodrigues, A. S.; Fogliano, V.; Graziani, G.; Mendes, S.; Vale, A. P.; Goncalves, C. Nutritional value of onion regional varieties in northwest Portugal. Electron. J. Environ. Agric. Food Chem. 2003, 2, 519-524.
38. Muminova, B. A.; Batirov, E. Kh.; Yuldashev, M. P.; Inamova, Z. G. Kaempferol glycosides from Allium cepa and Raphanus sativus. Chem. Nat. Compd. 2006, 42, 110.
39. Bonaccorsi, P.; Caristi, C.; Gargiulli, C.; Leuzzi, U. Flavonol glucoside profile of southern Italian red onion (Allium cepa L.). J. Agric. Food Chem. 2005, 53, 2733-2740.
40. Sellappan, S.; Akoh, C.C. Flavonoids and antioxidant capacity of Georgia-grown Vidalia onions. J. Agric. Food Chem. 2002, 50, 5338-5342.
41. Franke, A. A.; Custer, L. J.; Arakaki, C.; Murphy, S. P. Vitamin C and flavonoid levels of fruits and vegetables consumed in Hawaii. J. Food Comp. Anal. 2004, 17, 1-35.
42. Weissenböck, G.; Schnabl, H.; Scharf, H.; Sachs, G. On the properties of fluorescing compounds in guard and epidermal cells of Allium cepa L. Planta 1987, 171, 88-95.
43. Furusawa, M.; Tanaka, T.; Nakaya, K. I.; Iinuma, M.; Tuchiya, H. A new flavonol glucoside from onion. Heterocycles 2002, 57, 2175-2177.
44. Furusawa, M.; Tsuchiya, H.; Nagayama, M.; Tanaka, T.; Nakaya, K. I.; Iinuma, M. Anti-platelet and membrane-rigidifying flavonoids in brownish scale of onion. J. Health Sci. 2003, 49, 475-480.
45. Furusawa, M.; Tsuchiya, H.; Nagayama, M.; Tanaka, T.; Oyama, M.; Ito, T.; Iinuma, M.; Takeuchi, H. Cell growth inhibition by membrane-active components in brownish scale of onion. J. Health Sci. 2006, 52, 578-584.
46. Ly, T. N.; Hazama, C.; Shimoyamada, M.; Ando, H.; Kato, K.; Yamauchi, R. Antioxidative compounds from the outer scales of onion. J. Agric. Food Chem. 2005, 53, 8183-8189.
47. Vandevelde, A. J. J. Plasmolysis, Determination of the Toxicity of alcohols. Hand. v. III. Vlammsch. Nat. Geneeskuendig Congres. Antwerp, 481, 1899 From J. Chem. Soc., Abstr. 1900, 78 (II), 302.
48. Robinson, G. M.; Robinson, R. CXCVII. A survey of anthocyanins II. Biochem. J. 1932, 26, 1647-1664.
49. Bate-Smith, E. C. Flavonoid compounds in foods. In Advances in Food Research; Academic Press Inc., New York, 1954; pp 261-300.
50. Foussain, A. Identification par Chromatographie des pigments anthocyaniques des fruits et des legumes. Rev. Ferment. Ind. Aliment. 1956, 11, 173-192.
51. Fuleki, T. The anthocyanins of strawberries, rhubarb, radish and onion. J. Food Sci. 1969, 34, 365-369.
52. Fuleki, T. Anthocyanins in red onion Allium cepa. J. Food Sci. 1971, 36, 101-104.
53. Du, C. T.; Wang, P. L.; Francis, F. J. Cyanidin 3-laminariobioside in Spanish red onion. J. Food Sci. 1974, 39, 1265-1266.
54. Moore, A. B.; Francis, F. J.; Jason, M. E. Acylated anthocyanins in red onions. J. Food Prot. 1982, 45, 590-593.
55. Moore, A. B.; Francis, F. J.; Clydesdale, F. M. Changes in chromatographic profile of anthocyanins of red onion during extraction. J. Food Prot. 1982, 45, 738-743.
56. Terahara, N.; Yamaguchi, M.-A.; Honda, T. Malonylated anthocyanins from bulbs of red onion, Allium cepa L. Biosci., Biotechnol., Biochem. 1994, 58, 1324-1325.
57. Fossen, T.; Andersen, Ø. M.; Øvstedal, D. O.; Pedersen, A. T.; Raknes, Å. Characteristic anthocyanin pattern from onions and other Allium spp. J. Food Sci. 1996, 61, 703-706.
58. Donner, H.; Gao, L.; Mazza, G. Separation and characterization of simple and malonylated anthocyanins in red onions, Allium cepa L. Food Res. Int. 1997, 30, 637-643.
59. Fossen, T.; Slimestad, R.; Andersen, Ø. M. Anthocyanins with 4′-glucosidation from red onion Allium cepa. Phytochemistry 2003, 64, 1367-1374.
60. Ferreres, F.; Gil, M. I.; Tomás-Barberán, F. A. Anthocyanins and flavonoids from shredded red onion and changes during storage in perforated films. Food Res. Int. 1996, 29, 389-395.
61. Fossen, T.; Andersen, Ø. M. Anthocyanins from red onion, Allium cepa, with novel aglycone. Phytochemistry 2003, 62, 1217-1220.
62. Wu, X.; Prior, R. L. 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. 2005, 53, 3101-3113.
63. Gennaro, L.; Leonardi, C.; Esposito, F.; Salucci, M.; Maiani, G.; Quaglia, G.; Fogliano, V. Flavonoid and carbohydrate content in Tropea red onions: effect of homelike peeling and storage. J. Agric. Food Chem. 2002, 50, 1904-1910.
64. Andersen, Ø. M.; Jordheim, M. The Anthocyanins. In Flavonoids. Chemistry, biochemistry and applications; Andersen, Ø. M., Markham, K. R., Eds.; CRC Taylor & Francis: Boca Raton, FL, 2006; pp 471-552.
65. Corea, G.; Fatturusso, E.; Lanzotti, V.; Capasso, R.; Izzo, A. A. Antispasmodic Saponins from Bulbs of Red Onion, Allium cepa L. Var. Tropea. J. Agric. Food Chem. 2005, 53, 935-940.
66. Bilyk, A.; Cooper, P. L.; Sapers, G. M. Varietal differences in distribution of quercetin and kaempferol in onion (Allium cepa L.) tissue. J. Agric. Food Chem. 1984, 32, 274-276.
67. Tsushida, T.; Suzuki, M. Content of flavonol glucosides and some properties of enzymes metabolizing the glucosides in onion. J. Jpn. Soc. Food Sci. Technol. 1996, 43, 642-649.
68. Rhodes, M. J.; Price, K. R. Analytical problems in the study of flavonoid compounds in onions. Food Chem. 1996, 57, 113-117.
69. Price, K. R.; Rhodes, M. J. C. Analysis of the major flavonol glycosides present in four varieties of onion (Allium cepa) and changes in composition resulting from autolysis. J. Sci. Food Agric. 1997, 74, 331-339.
70. Price, K. R.; Bacon, J. R.; Rhodes, M. J. C. Effect of storage and domestic processing on the content and composition of flavonol glucosides in onion (Allium cepa). J. Agric. Food Chem. 1997, 45, 938-942.
71. Kiviranta, J.; Huovinen, K.; Hiltunen, R. Variation of phenolic substances in onion. Acta Pharm. Fennica 1988, 97, 67-72.
72. Crozier, A.; Lean, M. E. J.; McDonald, M. S.; Black, C. Quantitative analysis of the flavonoid content of commercial tomatoes, onions, lettuce, and celery. J. Agric. Food Chem. 1997, 45, 590-595.
73. Ewald, C.; Fjelkner-Modig, S.; Johansson, K.; Sjöholm, I.; Åkesson, B. Effect of processing on major flavonoids in processed onions, green beans, and peas. Food Chem. 1999, 64, 231-235.
74. Hertog, M. G. L.; Hollman, P. C. H.; Katan, M. B. Content of potentially anticarcinogenic flavonoids of 28 vegetables and fruits commonly consumed in The Netherlands. J. Agric. Food Chem. 1992, 40, 2379-2383.
75. Hertog, M. G. L.; Hollman, P. C. H.; Venema, D. P. Optimization of a quantitative HPLC determination of potentially anticarcinogenic flavonoids in vegetables and fruits. J. Agric. Food Chem. 1992, 40, 1591-1598.
76. Justesen, U.; Knuthsen, P.; Leth, T. Quantitative analysis of flavonols, flavones, and flavanones in fruits, vegetables and beverages by high-performance liquid chromatography with photo-diode array and mass spectrometric detection. J. Chromatogr. A 1998, 799, 101-110.
77. Lombard, K.; Peffley, E.; Geoffriau, E.; Thompson, L.; Herring, A. Quercetin in onion (Allium cepa L.) after heat-treatment simulating home preparation. J. Food Comp. Anal. 2005, 18, 571-581.
78. Lugasi, A.; Hovari, J. Flavonoid aglycons in foods of plant origin I. Vegetables. Acta Aliment. 2000, 29, 345-352.
79. Makris, D. P.; Rossiter, J. T. Domestic processing of onion bulbs (Allium cepa) and asparagus spears (Asparagus officinalis): Effect on flavonol content and antioxidant status. J. Agric. Food Chem. 2001, 49, 3216-3222.
80. Marotti, M.; Piccaglia, R. Characterization of Flavonoids in Different Cultivars of Onion (Allium cepa L.). J. Food Sci. 2002, 67, 1229-1232.
81. Mattila, P.; Astola, J.; Kumpulainen, J. Determination of flavonoids in plant material by HPLC with diode-array and electro-array detection. J. Agric. Food Chem. 2000, 48, 5834-5841.
82. Patil, B. S.; Pike, L. M.; Hamilton, B. K. Changes in Quercetin Concentration in Onion (Allium cepa L.) Owing to Location, Growth Stage and Soil Type. New Phytol. 1995, 130, 349-355.
83. Patil, B. S.; Pike, L. M.; Yoo, K. S. Variation in the quercetin content in different colored onions (Allium cepa L.). J. Am. Soc. Hortic. Sci. 1995, 120, 909-913.
84. Sampson, L.; Rimm, E.; Hollman, P. C. H.; de Vries, J. H. M.; Katan, M.B. Flavonol and flavone intakes in US health professionals. J. Am. Diet. Assoc. 2002, 102, 1414-1420.
85. Vinson, J. A.; Hao, Y.; Su, X.; Zubik, L. Phenol Antioxidant Quantity and Quality in Foods: Vegetables. J. Agric. Food Chem. 1998, 46, 3630-3634.
86. Yamada, K.; Naemura, A.; Sawashita, N.; Noguchi, Y.; Yamamoto, J. An onion cultivar has natural antithrombotic effect as assessed by thrombosis/thrombolysis models in rodents. Thromb. Res. 2004, 114, 213-220.
87. Arabbi, P. R.; Genovese, M. I.; Lajolo, F. M. Flavonoids in vegetable foods commonly consumed in Brazil and estimated ingestion by the Brazilian population. J. Agric. Food Chem. 2004, 52, 1124-1131.
88. Bahroun, T.; Luximon-Ramma, A.; Crozier, A.; Arouma, O. Total phenol, flavonoid, proanthocyanidin and vitamin C levels and antioxidant activities of Mauritian vegetables. J. Sci. Food Agric. 2004, 84, 1553-1561.
89. Crozier, A.; Burns, J.; Aziz, A. A.; Stewart, A. J.; Rabiasz, H. S.; Jenkins, G. I.; Edwards, C. A.; Lean, M. E. J. Antioxidant flavonols from fruits, vegetables and beverages: measurements and bioavailability. Biol. Res. 2000, 33, 79-88.
90. Wu, X.; Beecher, G. R.; Holden, J. M.; Haytowitz, D. B.; Gebhardt, S. E.; Prior, R. L. Concentrations of anthocyanins in common foods in the United States and estimation of normal consumption. J. Agric. Food Chem. 2006, 54, 4069-4075.
91. Herrmann, K. Flavonols and flavones in food plants: A review. J. Food Technol. 1976, 11, 433-448.
92. Starke, H.; Herrmann, K. Flavonole und Flavone der Gemüsearten. VI. Über das Verhalten der Flavonole in der Zwiebel. Z. Lebensm. Unters.-Forsch. 1976, 161, 137-142.
93. Leighton, T.; Ginther, C.; Fluss, L.; Harter, W. K.; Cansado, J.; Notario, V. Molecular characterisation of quercetin and quercetin glycosides in Allium vegetables: Their effects on malignant cell transformation. In Phenolic Compounds in Food and their effects on Health. II Antioxidants and cancer prevention; Huang, M.-T., Ho, C.-T., Lee, C.Y., Eds.; ACS Symposium Series 507; American Chemical Society, Washington, DC, 1992; pp 220-238.
94. Okamoto, D.; Noguchi, Y.; Muro, T.; Morishita, M. Genetic variation of quercetin glucoside content in onion (Allium cepa L.). J. Jpn. Soc. Hortic. Sci. 2006, 71, 100-108.
95. Harborne, J. B. Nature, distribution and function of plant flavonoids. Prog. Clin. Biol. Res. 1986, 213, 15-24.
96. Mogren, L. In Quercetin content in yellow onion (Allium cepa L); Acta Universitatis Agriculturae Sueciae, Alnarp, Sweden, 2006; Vol. 96, p 23.
97. Trammell, K. W.; Peterson, C. E. Quantitative differences in the flavonol content of yellow onion, Allium cepa L. J. Agric. Food Chem. 1976, 101, 205-207.
98. Wang, J.; Sporns, P. MALDI-TOF MS analysis of food flavonol glycosides. J. Agric. Food Chem. 2000, 48, 1657-1662.
99. Aziz, A. A.; Edwards, C. A.; Lean, M. E. J.; Crozier, A. Absorption and excretion of conjugated flavonols, including quercetin-4′-O-β- glucoside and isorhamnetin-4′-O-β-glucoside by human volunteers after the consumption of onions. Free Radical Res. 1998, 29, 257-269.
100. Kenmochi, K.; Katayama, O. Studies on the utilization of plant pigments. I. Anthocyanin pigments of red garlic (Allium sativum) and red onion (Allium cepa). Nippon Shokuhin Kogyo Gakkai-Shi 1975, 22, 598-605.