J. Agric. Food Chem.

2007, 55, 10067–10080

10067

REVIEWS
Onions: A Source of Unique Dietary Flavonoids
RUNE SLIMESTAD,*,† TORGILS FOSSEN,‡
AND INGUNN

MOLUND VÅGEN§

PlantChem, Særheim Research Centre, N-4353 Klepp station, Norway, Department of Chemistry, University of Bergen, Allégt. 41, N-5007 Bergen, Norway, and The Norwegian Institute for Agricultural and Environmental Research, Bioforsk Øst Landvik, Reddalsveien 215, N-4886 Grimstad, Norway

Onion bulbs (Allium cepa L.) are among the richest sources of dietary flavonoids and contribute to a large extent to the overall intake of flavonoids. This review includes a compilation of the existing qualitative and quantitative information about flavonoids reported to occur in onion bulbs, including NMR spectroscopic evidence used for structural characterization. In addition, a summary is given to index onion cultivars according to their content of flavonoids measured as quercetin. Only compounds belonging to the flavonols, the anthocyanins, and the dihydroflavonols have been reported to occur in onion bulbs. Yellow onions contain 270–1187 mg of flavonols per kilogram of fresh weight (FW), whereas red onions contain 415–1917 mg of flavonols per kilogram of FW. Flavonols are the predominant pigments of onions. At least 25 different flavonols have been characterized, and quercetin derivatives are the most important ones in all onion cultivars. Their glycosyl moieties are almost exclusively glucose, which is mainly attached to the 4′, 3, and/or 7-positions of the aglycones. Quercetin 4′-glucoside and quercetin 3,4′-diglucoside are in most cases reported as the main flavonols in recent literature. Analogous derivatives of kaempferol and isorhamnetin have been identified as minor pigments. Recent reports indicate that the outer dry layers of onion bulbs contain oligomeric structures of quercetin in addition to condensation products of quercetin and protocatechuic acid. The anthocyanins of red onions are mainly cyanidin glucosides acylated with malonic acid or nonacylated. Some of these pigments facilitate unique structural features like 4′-glycosylation and unusual substitution patterns of sugar moieties. Altogether at least 25 different anthocyanins have been reported from red onions, including two novel 5-carboxypyranocyanidin-derivatives. The quantitative content of anthocyanins in some red onion cultivars has been reported to be approximately 10% of the total flavonoid content or 39–240 mg kg-1 FW. The dihydroflavonol taxifolin and its 3-, 7-, and 4′-glucosides have been identified in onions. Although the structural diversity of dihydroflavonols characterized from onions is restricted compared with the wide structural assortment of flavonols and anthocyanins identified, they may occur at high concentrations in some cultivars. From bulbs of the cultivar “Tropea”, 5.9 mg of taxifolin 7-glucoside and 98.1 mg of taxifolin have been isolated per kilogram of FW.
KEYWORDS: Onion; Allium cepa; flavonoids; flavonols; anthocyanins; dihydroflavonols; cultivars; quantitative content; NMR

INTRODUCTION

Onion (Allium cepa L.) is one of the most important vegetables worldwide with an estimated annual production of almost 47 million tons in year 2000 (http://faostat.fao.org). The
* Corresponding author. Phone: +47-995-08-228. Fax: +47-51426744. E-mail: rune@plantchem.com. † Særheim Research Centre. ‡ University of Bergen. § The Norwegian Institute for Agricultural and Environmental Research.

main production areas are China, India, United States, Russia, Turkey, and Iran. Consumption per capita differs greatly between countries and areas, but a major trend seems to be that onion consumption is increasing worldwide. Onion has been recognized as an important source of valuable phytonutrients as flavonoids, fructo-oligosaccharides (FOS), and thiosulfinates and other sulphur compounds. Flavonoids continue to attract attention as potentially useful agents with implications for inflammation, cardiovascular diseases, and cancer (1, 2). The common onion belongs to the family Alliaceae and is biennial, but in commercial production it is mainly grown as

10.1021/jf0712503 CCC: $37.00  2007 American Chemical Society Published on Web 11/13/2007

chalcone synthase. quercetin 3. Food Chem.. an annual. and cultivars are commonly divided into groups based on growing latitude. The existing reviews including qualitative flavonoid contents of onions are still relatively incomplete. and isorhamnetin have . Content of potential health-promoting substances. In a preceding review (Herrmann. stem. 3GT. from tropical to cool temperate climates. dihydroflavonol 4-reductase. bulb storage life. This fact is often neglected in studies. DFR. color of the outer scales (yellow. F3H. The distribution with respect to structural diversity and quantities may vary considerably within a plant. red. quercetin 4′-glucoside > isoquercetin . CHI. Flavonoids are present in all terrestrial plants and are found in all plant organs including flower. Transition from leaf growth to bulb formation depends both on temperature and on the day length adaptation of the cultivar. followed by autoxidation to produce protocatechuic acid (8). malonyl coenzyme-A:anthocyanidin 3-O-glucoside-6′′-O-malonyltransferase. Q4′GT. Most of the structures reported prior to 1988 were elucidated by means of thin-layer chromatography and UVabsorption spectroscopy in combination with the use of UV shift reagents and acidic or enzymatic hydrolysis. The bulb consists of the swollen base of the stem and several fleshy leaves or scales. 2007 Reviews Figure 1. and root. white). flavonol synthase. Putative flavonoid biosynthesis pathway in A. Even though onions are among the most important dietary sources of flavonoids (10). 3MaT. This suggests an enzymatic formation of defence substances against infection in the dry skin from quercetin (9).4′-diglucoside. peroxidase in scales oxidize flavonols in the order quercetin . anthocyanidin synthase. Onions are grown in most climate zones around the world. fruit.10068 J. which is why we have chosen to pay special attention to variations among cultivars in this review. leaf. pungency (from mild and sweet to very pungent). the activity is higher in the outer than in the inner scales. F3′H. chalcone isomerase. like flavonoids. UDP glucose: flavonoid 3-O-glucosyltransferase. Moreover. 25. or approximately 70% of the real number of pre-1988 published flavonol structures from onions. ANS. Onions may differ greatly in bulb shape. 1988) only ten different flavonols were included (11). 5). cepa adopted from Masuzaki and co-workers. quercetin 4′-O-glucosyltransferase. Q3GT. No. flavonoid 3′-hydroxylase. 55. With respect to flavonoids. may also vary considerably between cultivars. kaempferol. flavanone 3-hydroxylase. Takahama and Hirota have suggested that quercetin is formed by deglucosidation of its glucosides. FLS. 7). and dry-matter content (3). Few structures were supported with mass-spectral (MS) data or data from nuclear magnetic resonance (NMR) spectroscopic investigations. no review exists that contains a comprehensive compilation of the various flavonoid structures characterized from these sources. CHS. and moreover. The compounds are of a mixed biosynthetic origin with one ring being shikimate-derived and the other being derived from the Krebs cycle (polyketide) (Figure 1) (4. Vol. quercetin 3-O-glucosyltransferase. Agric. only total hydrolyzed amounts of the three flavonol aglycones quercetin. Significant progress has been made with respect to assignment of structural genes involved in the flavonoid biosynthesis of onions (6. A more recent review (12) surveys different groups of compounds that have been reported from onions and garlic.

For the first time. 56–60. 67. 33.4′-diglucoside isorhamnetin 4′-glucoside isorhamnetin 3-glucoside isorhamnetin 3. 63 56–59. 65. 25. Among the more than 8000 known flavonoid structures. 71 21. 39. 67 33 40. 43. 60. 60. 71. of onions. 62 56–59. nearly half of them have been characterized during the last decade (13). 98. 60. 46 43. Vol. 41 43.. 100 21. 20. 60. 39. 21. 29. 100 57. 98 26. 29. 39 36 33. 60.4′-diglucoside kaempferol 3. the anthocyanins.6′′-dimalonylglucoside) cyanidin 3-(dimalonyl)laminariobioside cyanidin 3-(3′′-acetylglucoside) cyanidin 3-(malonyl)(acetyl)glucoside cyanidin 3. 63 57 58 62 62 57.Reviews Table 1. Despite the vast numbers of commercially important anthocyanincontaining onion cultivars. 32 28.4′-triglucoside quercetin 3-rhamnoside quercetin 3-rutinoside kaempferol kaempferol 4′-glucoside kaempferol 3-glucoside kaempferol 7. 51–53.7. 58.5-diglucoside peonidin 3-(6′′-malonylglucoside)-5-glucoside delphinidin 3-glucoside delphinidin 3-glucosylglucoside petunidin glucoside petunidin (glucosylglucoside) 5-carboxypyranocyanidin 3-glucoside 5-carboxypyranocyanidin 3-(6′′-malonylglucoside) Dihydroflavonols taxifolin 4′-glucoside taxifolin taxifolin 7-glucoside taxifolin 3-glucoside J. 59 62 59 59 59 59 52. 26. Flavonoids Reported To Occur in Bulbs of Onion (Allium cepa L. 27. Along with the continuous improvement in methods and instrumentation of isolation and structure determination of flavonoids. No. 60. Food Chem. 98 21–29. 27–29. 37. 2007 10069 refs 15–17. 62. 29. In this review. 50–53. 1 2 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 flavonoids Flavonols quercetin quercetin 4′-glucoside quercetin 3.5-diglucoside cyanidin 3-(malonyl)-glucoside-5-glucoside cyanidin 4′-glucoside cyanidin 3. 17. 67. 34. 29 16. particularly . 56–59. reviews including compilations of anthocyanins or any flavonoids other than flavonols are nonexistent in previous literature. 66. 67. 55. an extended anthology of the numerous quantitative analyses of flavonols. 67 26. Among the 13 different main flavonoid classes.4′-diglucoside quercetin 7-glucoside quercetin 7. 93 27. 34. 21. 46 46 46 21. 99 34. 59 57 59 63 63 63 63 61 61 27 65 65 60 been measured from onions. structural information with increasing levels of precision has become available on an increasing number of flavonoids. 62. Agric. 39. according to that review. and to less extent the dihydroflavonols have been reported from onion bulbs. 35 29. The majority of these structures have been confirmed through NMR investigations. 62. 99 26. 39 26. 26–29. a compilation of more than 50 flavonoids identified in pigmented scales of onions are included (Table 1). 62. 71. 58 58.7-diglucoside quercetin 3. and to some extent anthocyanins and dihydroflavonols.4′-diglucoside quercetin 3-glucoside quercetin 3′-glucoside quercetin 3. 63. 67 21–24.4′-diglucoside cyanidin 3-(3′′-glucosyl-6′′-malonylglucoside)-4′-glucoside cyanidin 7-(3′′-glucosyl-6′′-malonylglucoside)-4′-glucoside peonidin 3-glucoside peonidin 3-(6′′-malonylglucoside) peonidin 3. only compounds belonging to the flavonols. 39.) no. 71 34 29. and chemical shift values for both proton and carbon are reviewed. 28. 28. 38 29 26. Approximately 70% of these compounds have been reported during the last 15 years. 31. 67. 29.4′-diglucoside isorhamnetin myricetin quercetin dimer 4′-glucoside of quercetin dimer condensation products of quercetin and protocatechuic acid quercetin trimer Anthocyanins cyanidin 3-glucoside cyanidin 3-(3′′-glucosylglucoside) ) cyanidin 3-laminariobioside cyanidin 3-(3′′-malonylglucoside) cyanidin 3-(6′′-malonylglucoside) cyanidin 3-(3′′-glucosyl-6′′-malonylglucoside) cyanidin 3-(3′′. 28. 46.

The latter two compounds have not been identified in more recent studies of other onion cultivars. The glycosyl unit(s) of these pigments has in most cases been identified as glucose. Tsushida and Suzuki (26) additionally identified . 2007 Reviews Figure 2. quercetin 3. The presence of quercetin aglycone as one of the main flavonoids in some onion cultivars has been confirmed in later publications (16. They also tentatively indicated the presence of quercetin 5-glucoside and a quercetin 3-diglucoside. Panisset and Tissut (29) identified quercetin 3. These structures have been confirmed in later publications (23– 27).7diglucoside. 1. The structural diversity of the minor flavonols of onions is extensive and includes derivatives of kaempferol. Tissut (28) reported on the occurrence of quercetin 3-glucoside (isoquercitrin. as minor pigments from the cultivars 447. 14). 5.2 (30).2).4′-diglucoside.10070 J. Brandwein (21) isolated quercetin 4′-glucoside and quercetin 3. Altogether at least 25 different flavonols have been characterized from onion bulbs (Figures 2 and 3.1–3. 27.4′-diglucoside. as minor pigments. 947. 55. Abbreviations are as follows: glc ) glucose. Food Chem. Perkin and Hummel (1896) first reported the structure of quercetin. Hygro.4′-diglucoside in addition to the 7. One should however keep in mind that hydrolysis of quercetin glycosides might occur during sample preparation and analysis. rut ) rutinose. 2) in addition to quercetin from pigmented scales of the cultivar “Braunschweiger Dunkelblutrote”. dried pigmented scales of onions have been used to provide yellow coloration of textiles and Easter eggs (14). as minor pigments in the cultivar “Red Creole”. and Superba (29).4′-diglucoside and the 7. and quercetin 3′glucoside. and “Southport Red Globe”.3′. 6.4′pentahydroxyflavone). 8. of quercetin from the cultivars “Southport Yellow Globe”.4′-diglucoside. and the 3-glucoside. The identifications were based on paper chromatography and UV-spectroscopy with shift reagents. 4. 19). A complete NMR spectroscopic assignment of the structure of this compound isolated from onions is lacking in previous literature and has been included in Tables 2. from onion bulbs using cochromatography on TLC. Using TLC. Structures of flavonols (1 through 21) reported to occur in bulbs of onions (Allium cepa L. kaempferol. namely.. Flavonols are the main flavonoids of pigmented scales of onions. 17) identified another main flavonol of onions. Topaz.1–3. rha ) rhamnose. 7.5. Kaempferol had earlier been reported from the light pink Indian cultivar “Malwi” (31). and possibly myricetin. Panisset and Tissut also detected quercetin 7-glucoside. related to different cultivars. kaempferol 4′-glucoside. kaempferol 3-glucoside (astragalin. Omidiji (34) identified isorhamnetin 3-glucoside. 6). 17. The main flavonols are based on quercetin (3. and kaempferol 7. 935. FLAVONOLS OF ONIONS Figure 3. Table 1). isorhamnetin. 21. Herrmann (16. Vol. 17. Harborne (22) reported the 3. The identification of quercetin 4′-glucoside was mainly based on comparison of the physiochemical and paper chromatographic properties with the same compound previously isolated from Filipendula flos spirea and its tetramethylated derivative (18. No. 12. The third major flavonol.4′-diglucoside. 13. is included as one of the main objectives of this review.4′diglucoside of quercetin from an unspecified onion cultivar. quercetin 4′-glucoside (spiraeoside. Koeppen and van der Spuy (20) reported quercetin 4′-glucoside as the main flavonol in the cultivar “Australian Brown”. and isorhamnetin 4′-glucoside. 3. was reported at the same time in two independent papers. 18.). 25. Structures of flavonols (22 through 25) From ancient times. Agric. 29).The structures of the 4′-glucosides of kaempferol (32) and isorhamnetin (33) have more recently been confirmed by NMR spectroscopic studies (Tables 2. Hyper. The presence and amount of aglycone reported can therefore be an overestimate. 15. isolated from pigmented scales of onion bulbs (15).7. in addition to the main pigments quercetin 4′-glucoside and quercetin 3. “Southport White Globe”.

8 7.06 ref 27 chemical shift (ppm).20.2 7 8 6. 8.74. s ) singlet. d. 1.59. d. 8. 1.7 7.14 3′ 5′ 7. d. 13 1 7 2 8 3 5 9 20 18 17 flavonols kaempferol 4′-glc (D) quercetin (M) quercetin 3′-glc (D) quercetin 4′-glc (M) quercetin 3. 3.5 7.35 6.0 6. c Assignments may be reversed. (D/T20) ) DMSO-d6-CF3COOD 80:20. 8. d. d. 7. 1.85. 2. 1.68.18. d. 8.67.36 8.7 6′ 8.83. 8.3 7.8. 9.43 6. dd.9 6. d. s 3. d.19.18. ‘d’.8.7 2′′′ 7. 2.9 6.80. ‘d’.24.71 6. s 3. d.98.77. 8. d. d.08 7. 8. glc ) glucopyranose.04.9 6. 1. 7. d. d.82. 2.0 d.80. 2007 10071 chemical shift (ppm).37.1 ref 43 chemical shift (ppm). 2.44 6.4′-diglc (M/T5) cy 3-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) cy 7-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) pn 3-(6′′-mal-glc) (M/T5) pn 3-(6′′-mal-glc)-5glc (M/T5) 5-Carboxypyranocyanidin 3-(6′′-mal-glc) (D/T20) a (A) ) acetone-d6.0. 1.02. d. 2. in addition to trace amounts of isorhamnetin 3.3 8.4′-diglucoside. d.76.8. d.05 8. 8. d.8 7.0 4′ 5′ 7. kaempferol 3. multiplicity. 2.8 6.16. 1.1 6.23. 22 dimeric flavonols quercetin dimer 4′-glc (A) b 6 6.06 s (b) 9. d. s dd.74. d.4 6.35 6.8.4′-diglc (D) quercetin 3. 2. 2. 2.7. d. 2.8 7.0 6.4′-triglc (D) isorhamnetin (D) isorhamnetin 3-glc (D) isorhamnetin 4′-glc OCH3 6 6. 2.8. 2.5 dd.2 7.47.33 8.33 6′ 7. 2.3 7.9 6.0 OCH3 malonyl ref 57 57 56 s 57 s 56 s 57 s 59 59 59 59 59 4.8 ref 43 chemical shift (ppm).21.8. 1.13.02c 8 5.07 7.23.2 8.8. d.17. ref 32 27 34 27 30 27 30 27 33 34 33 dd. dd.02. 2 dd.44.0 7.0 7.44. d.13. 2.62 7.37. 2. 0.14. dd.0 6.2 7.14 6. 9.03 9. s 59 59 61 dd. chemical shift (ppm). 8.35 8.97 7. d.08 3a 4. 2.37.3 7. s 9.9 7.41. 2 6.37. 2. (M/T5) ) CD3OD-CF3COOD 95:5.4 dd. 8.9 7. 2. 0.64 7.59 3b 6 6.34. 2.9 6.1 8 6.89. 8.22.26.2 7.10 7.12.2 8.92. No.27. d.76. multiplicity. 2. 9.3 8. d.67 7.16.81. d. coupling constant (Hz) no. (D/T10) ) DMSO-d6-CF3COOD 90:10. 8. d.75 7.11. 2. ‘d’ ) semi-doublet. d.04.29.5 7. d. 55. d. dd. 2. 0.8 6′ 8. 8.13. d.8 7. dd. d 1. 3. multiplicity. ‘d’.42. d.20.6. d. d.3 8.13. 2 8.25 8.2 8. dd. 9.29. 19.5-diglc (M/T5) cy 3. 2. s 6. 2. coupling constant (Hz) no.6 7. Vol. d.35. s 6 6. d. dd. d. d. d.1.47. 1. d. 8. 8. 0. 2 8. 7. (M) ) CD3OD.16. d.8 2′ 8.44.2 2′ 8.39.3 8. 35 38 39 40 42 44 50 cy 3.7 6. 2.1. 2.57 7. 8.70.25.72 7. dd ) double doublet.4′-diglc (D) quercetin 7.8 6. d.5. dd.3 7.9 7. 9 7. d.25. dd. each accounting for more than 1% of the total flavonoid content.90 6.8. 0. b Mixture of two stereoisomers.0 6.7 3′′′ 5′′′ 7. d.20.1 2′ 7. 9. 0.8 6.8 7.8 7.8 7. 1.90. 8.20. 1.78.1 7. 8.09.8 7.9 7. 8.04 9. s 9.19. d.2 7.42. coupling constant (Hz) no.08.09.68. d. 25.70.7 8′′ 6. d. 8.02.01.34.13. multiplicity.8 7.2 8. 8.4 ‘d’. 26 27 27 29 30 30 cy cy cy cy cy cy cy anthocyanins 3-glc (M/T5) 3-(3′′-glc-glc) (M/T5) 3-(3′′-glc-glc) (D/T10) 3-(6′′-mal-glc) (M/T5) 3-(3′′-glc-6′′-mal-glc) (D/T10) 3-(3′′-glc-6′′-mal-glc) (M/T5) 3-(3′′-glc-6′′-metmal-glc) (M/T5) 4/β 9. 8.17.35.70.7-diglc (D) quercetin 3.16.74 6.93.2 8.32. 2.04. 1.12 8. s 6. d. 1H NMR Spectral Data of Flavonoids from Onions Recorded in Various Solventsa J.50.0 7. 2. d.26.01. 2.47 6.7 7. and quercetin 7-glucoside as minor pigments.81 7.69.79. 2.99 8. d.9 9. s 3.20 7. 2. 8. and . d. s 8. d.8 7. (D) ) DMSO-d6.9 9. 8.Reviews Table 2. 1.36. 9. 2.. d. Food Chem.77 6.54. dd. dd.0 3′ 4′ 5′ 7.4 6. 8.9. d. d. d. 1. d.5 7. 1.11 8. d. 1.25 6.8 6′ 8.7.99c 2′ 7. 2.98. 1.7 6. 51 dihydroflavonols taxifolin 4′-glc (M) 2 5. 0.13 8. isorhamnetin 4′-glucoside. 3.1 3′ 5′ 7. (T) ) CF3COOD.1 6. 8. 1.00. coupling constant (Hz) no.77.92. 2.50. d.19.95 6. coupling constant (Hz) no. d.82 7.11. dd. 8.92.7. d ) doublet. 2. quercetin 3-glucoside. 9 7. 1. d. dd.29.9 6. multiplicity.80 6. 1.8. 1.9 6. Agric. d.57.99 6. 2. 2.88. d. d. 3. 8.19 s (b) 9. 8.9. d.3 8.64.3 7. d.75.21 6. 23 dimeric flavonols quercetin dimer 4′-glc (A) b 6′′ 6. 2 6. d. 8. d.60.8 6′′′ 7.15.8 8 6.45. 1. d. 1. 2.27 6. s 9. mal ) malonyl. d.04 7.22.02. 8.18. 8. 2 dd. 3.10 7. 1. d. d.6 7.4 3′ 7.50.70.2 8. 0. 2.72.4′-diglucoside. 2.9 7. 2. 8.83. 1.18. d.92 6.75 6. s 4. d.5.89.

64. 6.07 3. 9 3. t.14. ddd. d.1.8.99 3.26. dd. d.55. (D/T10) ) DMSO-d6CF3COOD 90:10.42 3. t.5 4. (M/T5) ) CD3OD-CF3COOD 95:5. dd. 9. 9.83.4′-diglc (D) quercetin 7. ddd. t. 9.04.22 3.44 3.16–4.10 3.76. m 3. 1H NMR Spectral Data of Glycosyl Moieties of Flavonoid Glycosides from Onions Recorded in Various Solventsa chemical shift (ppm).44. t. dd.3 3.55.52.9. Together with quercetin 3-rhamnoside.47.16–4.0. 7.53.5. m 3. dd. 9.45–3. 1.6 3.3 3. dd. 11. 3.14. 13 7 2 8 8 3 3 5 5 9 9 9 18 23 glycosyl moiety kaempferol 4′-glc (D) quercetin 3′-glc (D) quercetin 4′-glc (M) quercetin 3. 3.38.0 3. 1.16–4. 7. d. m 3. 4.3 3.75. dd.7 3. 3.4 5.6 3. d. m 3. 7.3 3.0.3.04.23 3.4′-diglc (D) quercetin 3.0. 7. 9. 11. 7. m 3. 7. m 3. 3. t.73.8.65. dd. d ) doublet.9 5.1.54.30 3.7.21–3. m 51 26 27 27 29 30 30 30 30 taxifolin 4′-glc (M) cy cy cy cy cy cy cy cy cy 3-glc (M/T5) 3-(3′′-glc-glc) (D/T10) 3-(3′′-glc-glc) (D/T10) 3-(6′′-mal-glc) (M/T5) 3-(3′′-glc-6′′-mal-glc) (D/T10) 3-(3′′-glc-6′′-mal-glc) (D/T10) 3-(3′′-glc-6′′-mal-glc) (M/T5) 3-(3′′-glc-6′′-mal-glc) (M/T5) 3-(3′′-glc-6′′-metmal-glc) (M/T5) 3.59 3. 3. 12. 3.0. dd. dd. m 3.26 3. 9. m 3.00.1. m Dimeric Flavonols 3. 14. m Dihydroflavonols 3.49.88 3.74. 7. dd.50 3. 9 3.28 4.08.79.1.15.33 3. 3. 8 3. m 3.91. dd. m 3.72 3. 7.54. 6. 5. 2.30 3.56 3.50 3.39.46.4′-diglc (D) quercetin 7.5.65.64. 2.96.0. dd. m 3.60 3.65. 8 4.24 3.46.99. 12.71. 9.25–4. t.48.2. na ) not assigned. t. 8 3.53. dd.7 3. m 3.98. m 3. 2.45. 8.3 3. 8 3.39.0.14. 7. d.7 5. 9.78. glc ) glucopyranose.38 4. d. 4. 12.2 3.8. m 4.58 3.0.67 3. m 3.53.84. 3.45–3. 25. 12.83.23. 6.51–3. d. t.84 3.62. 12.98. 7. 35).69.7 4. 7. 9. m 3. 11. 2. d.84.4′-diglc (D) quercetin 3.98.64. 8 3. m 3.03. 12.46. 7. 12.61 3. 9.52.0 4.81.03 3. 7.91 5. 3.17. d. 7.1. 9.45–3.65.85 3. d. 7.4 4.42.52 Anthocyanins 3. t.00. m 3. 9. 8 4. d. m 4. mal ) malonyl. dd. 7. 11.94. dd.66. 11. d. 7. dd. m 3.69.67 3.43 3.84.4′-triglc (D) quercetin 3.1 27 57 56 56 57 56 56 57 57 59 59 59 59 59 59 59 59 59 59 59 59 59 59 59 61 cy 3-(3′′-glc-6′′-metmal-glc) (M/T5) 35 35 38 38 39 39 39 40 40 40 42 44 44 50 cy 3glc-5-glc (M/T5) cy 3glc-5-glc (M/T5) cy 3-glc-4′-glc (M/T5) cy 3-glc-4′-glc (M/T5) cy 3-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) cy 3-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) cy 3-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) cy 7-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) cy 7-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) cy 7-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) pn 3-(6′′-mal-glc) (M/T5) pn 3-(6′′-mal-glc)-5glc (M/T5) pn 3-(6′′-mal-glc)-5glc (M/T5) 5-carboxypyranocyanidin 3-(6′′-mal-glc) (D/T20) a cy ) cyanidin.1 4. Rodrigues and co-workers (37) reported kaempferol 3-glucoside.0.8.9 3.7 4. d.04.74. d.51.1. dd.0.32 3. 9.43. . 3. dd.12 3.56 3. 7.5 5.21 3. (A) ) acetone-d6.23 3.8. 6. m 3.21. 12.79 3. 9 4.. 6. m 3. dd. m 3. d.43 3. 3.06 3.71. 3.54.0. 3.1.7.0 4. 3.0.75.51–3.46 3.8.11 3.8 3.39.37 5. 7.59. d. 9. dd.38–3.2 4.75. m 3.16–4. m 3.43 3.40.1 3.4′-triglc (D) quercetin 3. 3.8 4.2 3. 7. 9 3.31.25–4. 12. 7.03. m 3. m 3.49. dd. dd. d. No. 2.2.14.9.2 3.39.39 3. t. 4.2 3.16 3. d. m 4.6 3.54.1. 3. Fossen and co-workers (27) isolated quercetin 3. dd.52. 9. dd.14.2. 6.7 5.47.63. 7.2 5. 7. 3. 12. m 3.38. d.67.98. 12. Food Chem.8 3.0 3.48 4.46 3.84.7 5. dd. 9.59 3.38. ddd ) double double doublet.15. 2.18 t 9.19 3.7 5. m 3. dd. (D) ) DMSO-d6.75. 2. 9.7 4.15.9 5.85 5.39. m 3.0. (T) ) CF3COOD.49.3. 2. 3.87 5.85. b Mixture of two stereoisomers.0 4. t. dd.0.78.44. 2.10072 J.54 3.05.3.7 5. 11.43. Agric. 11.2.39.52. d.16. dd.25. 7.8.8.74 4. d. d.08.76 3. dd.69. Vol. 6.5.01.73.53.73 3. t.33.1. 9.21 3. d.49.68. 9 3. m 3. 4. 9 3. t. 9. 7.51.1. t.56 3.76.24. m ref 32 34 27 30 30 27 27 30 30 27 27 27 34 (43) 3. m na H-4 na H-5 H-6 3.51–3.65. 3.0. t ) triplet.2. m 3. dd. 2. 11.00 5. as a minor pigment from the cultivars “Póvoa White” and “Póvoa Red” using HPLC. dd. t. 3. m 3. 3.45–3.34 3. t.61.4′-triglucoside. 3. dd. 9.84.26.0 4.95.64. 12.14.9 3.8 5.0.57 3. multiplicity.7-diglc (D) quercetin 3.7. 12. coupling constant (Hz) no.0 3.69.98.29.4 4. m 3.3 3.59 3.71. t. dd.25–4. 11. 9.40.9 3.49. dd. m 3.8 4. 4. d.42 3. 7.8.19. t.71 5.7 na H-2 H-3 Flavonols na 3.82 4.52.8.5.08.62 3.5 4. 9. 11. 12.17.0. 9.1.17.58 3. 7. m 3. m 3. rutin is the only reported flavonoid from bulbs of onions containing a glycosyl unit other than glucose.67.62. 6. ddd.24.41 3.62.67 3. m 3. 7. 7. 11. 3.4 5. 12. Quercetin 3-rutinoside (rutin.66. d.21 3. in addition to quercetin.7 4.09 5. 2. m 4.4′-triglc (D) isorhamnetin 3-glc (D) quercetin dimer 4′-glcb (A) H-1 4. 12. dd ) double doublet. m 3.15. 1.14. m ) multiplet. m 3. 12.0. m 3. d. 12.64.69. 7. 2.86.08. dd. d. t. 5. m 3. 3.7 5. br t.0 3.84. 11. m 3. d b. 7.25–4. dd.16–4. 7. m 3. 7.36 5.65. m 3. 3. t.85.2.0.38 3.38. 5.37 4.42 3.02. m 3.3. 11. pn ) peonidin. 7. 7.43. m 3. 2007 Reviews Table 2.52.35. 11) has been reported as a minor flavonoid in different onion cultivars (33.45–3.25–4. 11.27 3.37 3.96 3.0.7.8.29 t 9. m 3. d.40. dd.01.71.14 3.7 5.07 3.63.39. d.8. 2. dd. ‘d’ ) semi-doublet.73.41 4. m 3. ddd.7-diglc (D) quercetin 3.46 3.51.3.8. 12.3 4.8 5.1. m 3. kaempferol 4′-glucoside. dd.22 3. m 3. 4. m 3. 10 (36).65.51. 2.48.60.7.53 3.60 3. 6.3. 4. The parts in bold indicate the monosaccharide involved. 3. m 3.62. m 3. 9.02 3.07. d.06. m 3.26 3.7 3.31 3.2 4. 55.7.7. The latter compound was recently isolated from onion sources and its structure confirmed by NMR spectroscopy (38).69.83 3.2. 12.15. dd. t.51 4.2 3.3.47. br s. 7. 8 5. m. 9. 1.79.8 3. dd. dd. 4. 9 3. 1. m 3.3 3. m.0 3.8 4.7 4. m 3.38. 8 3. 9. 7. 8 5. (M) ) CD3OD.53.71. 12.46. 5.

4′-diglc (D) quercetin 3.33 128.32 145.20 109.54 137.95 155.55 136.04 56.44 116.65 168.3 59 42 44 50 164.76 168.83 144.08 94.2 148.6 4 176. mal ) malonyl.10 115.80 156.33 164. 29 30 42 50 anthocyanins cyanidin 3-(6′′-mal-glc) (M/T5) cy 3-(3′′-glc-6′′-mal-glc) (M/T5) cy 3-(3′′-glc-6′′-metmal-glc) (M/T5) pn 3-(6′′-mal-glc) (M/T5) carboxypyrcy 3-(6′′-mal-glc) (D/T20) COOH R β 1 Mal 166.06 165.77 120.34 136.52 94.2 2′ 3′′′ 148.00 na 103.2 na na na 118.15 168.54 121.41 129.36 160.55 137.00 146.56 134.92 146.3 145.4 na 95.79 164.60 104.26 93.40 27 26 26 26 26 27 26 27 30 27 no.3 3 3′′ 92.71 113.77 113.3 na na 117.62 116. in addition to minor amounts of .19 147.8 117. (D) ) DMSO-d6.8 169.6 136.59 168.72 162.22 115.6 ref 43 no.46 147.63 116.11 158.1 3′ 142.1.4 8 94.18 118..05 119.88 134. Vol.86 117.22 115.36 177.96 99. 55.74 147.46 128.4 173.1 2′ 117.17 115.50 147.4′-diglc cyanidin 3-(6′′-mal-glc) (M/T5) cy 3-(3′′-glc-6′′mal-glc) (M/T5) cy 3-(3′′-glc-6′′metmal-glc) (M/T5) cy 3-(3′′-glc-6′′mal-glc)-4′-glc (M/T5) cy 7-(3′′-glc-6′′mal-glc)-4′-glc (M/T5) pn 3-(6′′-mal-glc) (M/T5) pn 3-(6′′-malglc)-5glc (M/T5) carboxypyrcy 3-(6′′-mal-glc) (D/T20) 2 3 4 5 6 7 8 9 10 1′ 2′ 3′ 4′ 5′ 6′ OCH3 ref 57 59 59 57 163.30 145.89 133.86 177.5 na na 117.0 126.94 117.57 136.6 147.57 115.26 99.48 170.72 96. and quercetin 3.01 176.20 160.Reviews Table 3.23 118.69 97.66 103.39 128.46 106.28 149.96 115.and heteronuclear NMR spectroscopic techniques.7 156.07 116.26 121.86 115.66 99.98 121.3 7 7′′ 170.70 27 anthocyanins cyanidin 3-glc (M/T5) cy 3.33 155.84 117.02 124.13 116.37 177.25 109.01 121.13 32 158. carboxypyrcy ) 5-carboxypryanocyanidin.0 146.32 121.65 162.69 159.54 105.22 168.9 119. b Assignments may be reversed.4 4 4′′ 188. 23 dimeric flavonols quercetin dimer 4′-glc 2 145.99 94.69 98. and 2D homo.05 160.9 10 104.49 156.16 156.4 157.34 na na na b 159.91 136.9 4′ 141.45 170.23 121.05 153. cy ) cyanidin.68 165.21 147.07 101.55 156.2 127.6 5′ 6′′′ 120.51 120.34 163.8 a (A) ) acetone-d6.5 na na na na na 123. no.91 59 97.52 103.46 155.44 116.2 8 8′′ 97.35 102.25 158.72 156. Food Chem.52 121.78 148.86 59 39 163.49 115.6 152.50 136.6 10 1′′′ 127.95 117.99 115.08 144.46 160.5-diglc cy 3.32b 164. glc ) glucopyranose. No. (D/T10) ) DMSO-d6-CF3COOD 90:10.03 2 Mal na na 41.22 148.20 103.1 na 101.50 157.86 105.0 3′ 4′′′ 147.06 136.75 145.4 121.40 170.28 ref 57 57 59 59 61 160.16 118. Agric.72 148.22 116.14 153.53 104.4′-diglucoside from pigmented scales of the cultivar “Red Baron”.61 146.7-diglc (D) quercetin 3.12 127.52 146.5 na na na 115.97 156.83 156.21 135.91 145.18 120.59 167.62 121.6 9′′ 160.5 146.60 121.4 95.70 na na 3 Mal 170.89 164.70 103. (D/T20) ) DMSO-d6-CF3COOD 80:20.19 118.52 no.12 124.3 7 165.42 119.19 133.73 148.50 95.48 146.25 98.0 na na 138.1 6′ 120.65 129.47 30 164.59 156.37 115.48 57 164.25 103.48 147.11 129. 26 35 38 29 dimeric flavonols quercetin dimer 4′-glc dihydroflavonols 2 2′′ 101.83 155.5 na na na 159.10 103.72 146.16 98. quercetin 4′-glucoside. The structure determinations were based on acid hydrolysis.36 147.85 161.40 101.39b 165. 23 no.30 168.75 133.67 146.04 104.6 5 5′′ 165.5 4′ 5′′′ 117.6 6′ ref 43 ref taxifolin 4′-glc (M) 85.2 1′ 127.27 103.12 104.40 93.10 162.19 156. na ) not assigned.81 145.8 5′ 118.32 128.70 198.67 120. 2007 C NMR Spectral Data of Flavonoids from Onions Recorded in Various Solventsa flavonols 2 3 4 5 6 7 8 9 10 1′ 2′ 3′ 4′ 5′ 6′ 10073 ref kaempferol 4′-glc (D) quercetin (M) quercetin (D) quercetin 3-glc (D) quercetin 7-glc (D) quercetin 4′-glc (D) quercetin 4′-glc (M) quercetin 3.05 177.97 115.8 na 57.3 148.17 157.24 121.66 162.32 93.4 3 137.25 97. 51 no.77 117.49 95.90 99.2 113.81 147.89 116. The same compounds were reported to occur in a southern Italian onion cultivar.88 168. pn ) peonidin.15 121.11 104.62 162.21 115.6 129.82 176.38 93.54 na 105.05 121.52 121.2 118.50 160.37 147.44 155.31 94.20 176.58 146.52 154.57 155.90 145.1 1′ 2′′′ 117.04 155.45 94.59 174.31 157.8 105.88 98.0 6 6′′ 98.76 168.20 121.37 118.06 146.55 73.22 156.6 158.39 147.00 104. chromatography (TLC and HPLC).8 59 40 na na 139.34 155.71 99.79 148.19 170.7 117.54 na na 113.67b 120.26 157. (M) ) CD3OD.33 118.5 164.62 124.61 145.94 162.01 135.96 116.3 6 99.21 98.3 141.7.89 126.79 153.06 156.47 160.1 na na na na 118.93 159.64 160. (T) ) CF3COOD.42 115. (M/T5) ) CD3OD-CF3COOD 95:5.26 136.61 124.62 117.92 125.1 59 61 165.47 94.7 na 101.7 na na 117.75 161.7 9 157.48 165.51 52.33 175.58 113.58 145.57 147.05 125.0 124.6 9 10′′ 100.31 99.4′-diglc (D) quercetin 7.91 113.96 147.4′-triglc(D) 145.27 137.8 5 162. 13 1 1 6 4 2 2 8 3 5 9 13 J.09 115. 25.46 116.68 164.6 177.45 176.50 94.41 137.43 170.

19 78.15 73.2 71. as one of the main anthocyanins.2 71.36 70. Table 1).39 74.6 102.79 61.41 77.7 78. In an early survey.69 99.32 69. Furusawa and co-workers (43) isolated quercetin and quercetin 4′-glucoside together with novel isomeric quercetin dimers (Figure 3).36 65.4′-diglc (D) quercetin 7.7 74.9 87.6 78.9 102.3 104.50 76.0 71.44 60.87 98. Agric.54 100. Fouassin (50) reported the presence of three cyanidin derivatives in red onion including a cyanidin monoside and a cyanidin diglucoside.52 C-4 69.7 102.13 104.56 69.2 71.0 77.7 62. as well as condensation products of quercetin and protocatechuic acid.7.24 74.08 74. TLC and HPLC analyses. has been preliminarily characterized (40.45 65.88 78. identified cyanidin 3-glucoside.7-diglc (D) quercetin 3. dry scales of onions.2 75.8 64.1 77. and traces of isorhamnetin 3-glucoside. 13 6 4 2 2 8 8 3 3 5 5 9 9 9 23 51 26 29 30 30 35 35 38 38 39 39 39 40 40 40 42 44 44 50 glycosyl moiety flavonols kaempferol 4′-glc (D) quercetin 3-glc (D) quercetin 7-glc (D) quercetin 4′-glc (D) quercetin 4′-glc (M) quercetin 3.4′-diglc (D) quercetin 7.08 71. These dimers were either glucosylated at the 4′-position.2 71.61 60. 25.42 100. However.0 78.28 79.78 C-6 60.89 87. The identification of peonidin 3-arabinoside (21) could not be confirmed by Fuleki (51. The parts in bold indicate the monosaccharide involved.9 75.4′-diglc (D) quercetin 3. Food Chem.32 105.3 75.47 65. (M/T5) ) CD3OD-CF3COOD 95:5.92 77.22 76. Du and coworkers (53) identified a second major anthocyanin as cyanidin 3-(3′′-glucosylglucoside) (also known as cyanidin 3-laminari- . 26. after complete hydrolysis of a red onion extract.2 78. No.61 69.0 77. (T) ) CF3COOD.7 103. Vol.1 75.83 77. 41.64 65.2 78.73 62.7 103.0 71.80 71.96 70.58 74.13 a glc ) glucopyranose.3 70. 103. 2007 13 Reviews Table 3.61 77.6 62.8 105.49 76.83 69.14 77.5 78.92 101.36 77. 45).7.1 70.5 75.5.7 74.93 100.93 75.88 71.56 C-2 73.23 77.96 77.91 75. Robinson and Robinson (48) indicated that the red skins of cv. combined with hydrolytic treatment of flavonoid-containing extracts from onions.8 87.86 61.94 60.3 104.30 ref 32 26 26 26 27 26 26 27 27 30 30 27 27 27 43 27 57 57 57 57 59 59 59 59 59 59 59 59 59 59 59 59 59 59 59 61 Dimeric Flavonols 103.79 74.1 78.76 77. Bate-Smith and coworkers suggested a cyanidin glucoside (49). The compounds are found to interact with lipid bilayers and change the fluidity of liposomal membranes (44. “Sutton’s Blood Red” contained a cyanidin derivative glycosylated with a bioside composed of an unidentified pentose and an unidentified hexose.7 62.72 103.68 99.4 62.3 78.29 78. isorhamnetin 3.3 103.2 71.19 73.2.6 60.36 61.6 77.54 76.6 78. 19.5 74.92 69.4 95.17 74. 18 (39).3 78.38 103.4 65.45 62.6 71. 21.56 70.5 74. however.61 69.13 69.66 73.4′-triglc (D) quercetin dimer 4′-glcb (A) taxifolin 4′-glc (M) cy 3-glc (M/T5) cy 3-(6′′-mal-glc) (M/T5) cy 3-(3′′-glc-6′′-mal-glc) (M/T5) cy 3-(3′′-glc-6′′-mal-glc) (M/T5) cy 3-(3′′-glc-6′′-metmal-glc) (M/T5) cy 3-(3′′-glc-6′′-metmal-glc) (M/T5) cy 3glc-5-glc (M/T5) cy 3glc-5-glc (M/T5) cy 3-glc-4′-glc (M/T5) cy 3-glc-4′-glc (M/T5) cy 3-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) cy 3-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) cy 3-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) cy 7-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) cy 7-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) cy 7-(3′′-glc-6′′-mal-glc)-4′-glc (M/T5) pn 3-(6′′-mal-glc) (M/T5) pn 3-(6′′-mal-glc)-5glc (M/T5) pn 3-(6′′-mal-glc)-5glc (M/T5) 5-carboxypyranocyanidin 3-(6′′-mal-glc) (D/T20) C-1 99. Glycosides of myricetin have hitherto not been detected in onions.60 61.04 62. 24 (Figure 3).15 77. (D/T10) ) DMSO-d6-CF3COOD 90:10.6 74.7 74.14 77.61 71.90 87.6 Dihydroflavonols 104.60 78.7 62. Vandevelde (47) first mentioned red onion as a rich source of anthocyanins.4 62. in addition to minor amounts of peonidin 3-glucoside.4 62.05 C-5 77. of one of the quercetin subunits or nonglucosylated. 55.98 71.10074 J.22 73.5 74.12 77.6 102.3 78.4′-diglucoside. Such compounds have also been isolated by Ly and co-workers (46) who also indicated a trimeric and further dimeric flavonoid structures derived from quercetin.0 78.58 78.13 75.6 62.75 60.05 73.01 75.13 72.58 103.37 78.29 75. From the brownish.0 71.5 65.73 101.4′-triglc (D) quercetin 3.57 77.4 74.5 62.30 101. (M) ) CD3OD.56 77. complex dimeric and trimeric flavonoids isolated from onions have been reported (43–46).63 78.82 74.46 60.5 71.64 62. 41).1 76. ANTHOCYANINS OF ONIONS The qualitative anthocyanin content of red onion cultivars includes a wide structural assortment including several unique flavonoid structures (Figures 4 and 5.55 73.7-diglc (D) quercetin 3.3 77.0 74.5 65.90 75.76 101.4 71.4′-diglc (D) quercetin 3.49 76.33 71.6 76.46 74.7.10 60.7 78.23 101.92 71.33 71.95 69.31 69.68 69.56 77.01 73. b Mixture of two stereoisomers.14 103.19 69.98 60.81 74.39 76..46 73.50 76.8 102. (D) ) DMSO-d6.04 76.9 74.6 74.55 C-3 76. mal ) malonyl.49 77.55 77. 52) who.54 76.77 75.86 99.00 78.81 102. revealed the presence of kaempferol and quercetin glycosides substituted with sulphate and glucuronic acid (42). 22. As a consequence of the significant improvements in methods and instrumentations used for separation and structure elucidation (13). These pigments still await NMR spectroscopic and mass spectral characterization.66 76. myricetin aglycone.0 78.87 Anthocyanins 103.34 105.1 76.44 62.4′-triglc (D) quercetin 3.01 62. 23. 25.28 74. C NMR Spectral Data of Glycosyl Moieties of Flavonoid Glycosides from Onions Recorded in Various Solventsa chemical shift (ppm) no. (A) ) acetone-d6. especially during the last decade.64 73.

25. 38. Most of the anthocyanins reported to occur in various cultivars of red onion are cyanidin derivatives. minor amounts of acetylated pigments have recently been detected by LC-MS analysis (62). that is. 51. anthocyanins acylated with malonic acid are the quantitatively most significant. The main anthocyanins of all cultivars investigated are exclusively glycosylated at the anthocyanidin 3-position. belonging to the group of pyranoanthocyanins that are regarded as particularly color-stable compared with analogous anthocyanidin glycosides (Figure 5). 54. quercetin 7-glucoside.). More recently. “Sweet Spanish hybrid”. have been identified (57). 55.7.9 mg of taxifolin 7-glucoside. and “Walla Walla”. Among the remaining flavonols. However. who reported the main anthocyanins of this cultivar to be the 3-glucoside. Agric. of the total quercetin content in onion skin was present as quercetin aglycone (66). 58. in more recent literature. from pigmented scales of cv. and 5-carboxypyranocyanidin 3-(6′′-malonylglucoside). QUANTITATIVE AMOUNTS OF FLAVONOIDS IN ONION CULTIVARS Particularly in the early literature.4′-diglucoside. Among the pigments characterized by NMR spectroscopy and mass spectrometry. Food Chem. No. which is cultivated in Southern Italy. quercetin aglycone has been identified as one of the major pigments of several cultivars (17. DIHYDROFLAVONOLS Figure 4. of cyanidin that were recently characterized from pigmented scales of red onion (59) are the only anthocyanins with a glycosyl at the 4′-position (13. and 51%. Fossen and Andersen (61) characterized minor amounts of 5-carboxypyranocyanidin 3-glucoside.4′diglucoside. The 4′-glucoside. 50. lam ) laminariobioside (3-glucosylglucoside). 29. 37. 50%. respectively (26. 61. 37. 35. the 3-arabinoside. the glycosyl moiety of anthocyanins from red onions is restricted to glucose (Tables 2. From bulbs of the cv. “Red Hamburger”.4′-diglucoside. Fossen and co-workers (27) characterized the rare dihydroflavonol taxifolin 4′-glucoside. the predominant flavonol and anthocyanidin aglycones found in pigmented scales of onions. been identified as the main flavonols. and the 3. However.4′-diglucoside have in most instances. 62). However. minor amounts of peonidin 3-(6′′-malonylglucoside)-5-gluco- The dihydroflavonols identified in onions (Figure 6) are all based on taxifolin (3. Vol.5-diglucosides of cyanidin. and these pigments predominate the anthocyanin profiles of red onions. quercetin 3-glucoside. “Red Baron”’ by the application of 1D and 2D NMR spectroscopy. ac ) acetoyl. the 3-(3′′-glucosyl-6′′-malonylglucoside)-4′-glucoside. 55) indicated the presence of significant amounts of anthocyanins acylated with aliphatic acids. and the 7-(3′′-glucosyl-6′′-malonylglucoside)-4′-glucoside. Corea and co-workers (65) isolated 5. 40. 57. and isorhamnetin 4′-glucoside have each been recognized to account for more than 1% of the total flavonoid content (26). derivatives of kaempferol.. the main anthocyanins of several red onion cultivars have been identified as cyanidin 3-(6′′-malonylglucoside). 64). “Early Yellow Globe”. the 3-malonylglucoside. “Tropea”. they may occur at high concentrations in some cultivars (65). 52. 30. In “Carmen hybrid”. The cultivar “Tropea” seems to be exceptional due to a relatively high content of delphinidin derivatives (about 30 % of the total anthocyanin content) and the presence of petunidin derivatives (63). and the 3-malonylarabinoside of cyanidin.1 mg of taxifolin per kilogram of FW. The cultivars Póvoa red and Póvoa white have been indicated to contain exclusively di. in addition to cyanidin 3-glucoside and cyanidin 3-(3′′-glucosylglucoside). Although the structural diversity of dihydroflavonoids characterized from onions is restricted compared with the wide structural assortment of flavonols and anthocyanins identified from the same source. structural evidence for these compounds has not been presented. 40%. 52. “Sweet Spanish Utah”. However. Recently. quercetin 7. respectively. Malonic acid is the main acyl moiety of acylated anthocyanins of red onion cultivars (56–63). although minor amounts of peonidin derivatives have been identified (Table 1) (51. Moore and co-workers (54. 66).3′. however. without determining their identities. Structures of anthocyanins (26 through 48) reported to occur in bulbs of onions (Allium cepa L. 23%. 44 (59). 2007 10075 side. 35.1–3. These two pigments have been shown to account for more than 80–85% of the total flavonoid content in some yellow cultivars.2). According to the recent literature (56–60).and monoglucosyl derivatives of delphinidin and petunidin (37). 53%. in Spanish red onion (cultivar “Morada de Amposta”). the latter two pigments are lacking NMR spectroscopic and mass spectral characterization. however. The identification of cyanidin 3-(3′′-glucosylglucoside) as one of the main anthocyanins in Spanish red onion (53) could not be confirmed by Ferreres and co-workers (60). 43. Abbreviations are as follows: glc ) glucose.4′-pentahydroxyflavanone). 49. Ferreres and co-workers (60) identified taxifolin 3-glucoside. 39%.Reviews J. and 98. 27 (56–59). isorhamnetin. with concentrations from 50 to 1300 and from 36 to 394 mg · kg-1 FW for quercetin 4′-glucoside and quercetin 3. mal ) malonyl. 27). obioside. 39. Although there is some variation regarding the relative quantitative content of individual flavonols in different cultivars. quercetin 4′glucoside and quercetin 3. 28. 53. 67–71). 24%. and myricetin have been reported to comprise altogether 19% and 21% of the total flavonoid contents in . the 3. and peonidin. “Yellow Globe hybrid”.5. These anthocyanins are among the main pigments in all recently investigated cultivars. which exhibits structural analogy to quercetin and cyanidin. and cyanidin 3-(3′′-glucosyl-6′′-malonylglucoside).

69. Moreover.5–6. of the total flavonoid contents in the edible parts of the bulbs. In a study on the cultivar “Stuttgarter Riesen”. 92). respectively.7 mg · kg-1 FW. Rodrigues and coworkers (37) reported that the anthocyanin content of the edible portions of “Póvoa white” and “Póvoa red” were 39. cyanidin 3-laminariobioside 17. respectively.5% flavonols by weight with 67–86% being quercetin aglycone and only to a smaller extent quercetin 4′-glucoside. “Red Bone”. Quercetin derivatives comprised more than 90% of the total flavonol content. and their concentrations increase continuously. Vol. In a screening program involving 75 onion cultivars grown in Texas. Also variation within populations is an important factor as intraspecific differences regarding flavonoid contents have been detected in well-known species (95). and 0. Donner and co-workers reported on the total content of anthocyanins in four cultivars of red onions (58). Abbreviation glc ) glucose. 25. 3% cyanidin 3-(3′′-glucosylglucoside). and 27 mg of myricetin per kilogram of FW. Food Chem. The one with the highest score. The total flavonoid contents in “Red baron” and “Rose” were 803 and 711 mg · kg-1 FW. 11 mg of kaempferol. It has been found that yellow and red onions are exceptional with respect to their high flavonol content (91). According to Fossen and co-workers (57).gov/fnic/foodcomp/Data/ Flav/Flav02-1. 69. the cultivar “Red Baron” contains 51% cyanidin 3-(6′′-malonylglucoside). mainly as the 4′glucoside and the 3.4%. whereas formation of quercetin 3.2 mg of myricetin per kilogram of FW.8% of the total anthocyanin content. and the amounts of compounds bearing the same flavonoid skeleton have been summarized.2% and 0. and soil type affected the total level of flavonols (82). 55. and up to 12 mg of peonidin per kilogram of FW (60. growth stage. respectively (41. Agric. Okamoto and co-workers recently reported on the differences in quercetin content between long-day cultivars and short-day cultivars (94). 6 mg of kaempferol. For instance. it was shown that location.usda. 70. 0–23 mg of delphinidin. contained 219 mg of anthocyanins per 100 g of DW and cyanidin 3-malonylglucoside accounted for 39. In some cases unhydrolyzed extracts have been analyzed on a molar basis. 63.4 and 53. whereas cyanidin 3-(6′′-malonylglucoside) and cyanidin 3-(3′′-glucosyl-6′′-malonylglucoside) contributed to the overall anthocyanin concentration with 15 and 10 mg · kg-1 FW. There appear to be no flavonols in the mesophyll. 50 mg of isorhamnetin. 87–90). The epidermis is found to contain glucosides exclusively.10076 J. Rhodes and Price (68) reported that the anthocyanins of the red cultivar “Red baron” and the pink cultivar “Rose” comprised 9. Quercetin 4′glucoside is believed to be formed first.8%. 2007 Reviews Figure 5.. hydrolyzed extracts of some red and yellow cultivars. 67. respectively. Gennaro and co-workers reported delphinidin 3-glucosylglucoside to be the major pigment in the edible portion of “Tropea” (65 mg · kg-1 FW). and cyanidin 3-glucoside 6. The flavonol concentration decreases from the outer to the inner scales with higher levels in the outer than in the inner epidermis (9. yellow onions contain 214 mg of quercetin. respectively (63). 66. 43 mg of isorhamnetin.4′-diglucoside of quercetin. respectively. the total flavonol content increased during the growth season from 990 to 7900 mg · kg-1 DW (92). This indicates that the sum of several minor/trace pigments. seems to be quantitatively significant. Some red onion cultivars have been found to contain 334 mg of quercetin. whose individual concentrations may be too low to be isolated. No.7%.nal.pdf). Structures of dihydroflavonols (51 through 54) reported to occur in bulbs of onions (Allium cepa L.5%. 22% cyanidin 3-(3′′-glucosyl6′′-malonylglucoside). Outer dry skins contain 2. Figure 6. the . cyanidin 3-malonyllaminariobioside 23.4′-diglucoside follows during storage. Some authors point out the importance of location and genetic factors on the impact of quercetin content (66. 93). based on calculations of quantities of their anthocyanidins has been indicated to be 62–240 mg of cyanidin.usda. The maximum values reported for quercetin in yellow and red onion are 1187 and 1917 mg · kg-1 FW. According to the USDA Database for the Flavonoid Content of Selected Food (http://www.nal. and 18% cyanidin 3-glucoside. Determinations of absolute quantities of anthocyanins in red and pink onion cultivars are sparse in the literature. The long-day cultivars of Rijnsburger type from Northern Europe and their close relatives contain higher concentrations of quercetin glucosides than those of Japanese and North American origins. respectively (http://www. indicating that the corresponding anthocyanin contents of these two cultivars were 74 and 5 mg · kg-1 FW. Determinations of flavonoid content are in most cases based upon analysis of liberated aglycones after hydrolysis of extracts.pdf).). 72–86). Structures of the 5-carboxypyranoanthocyanins 49 and 50.gov/fnic/foodcomp/Data/Flav/Flav021. The anthocyanin content in red onions.

Reviews J. Vol. .. Quantitative Flavonol Contents of Various Onion Cultivars Quantified as Milligrams of Quercetin per Kilogram of FWa cultivar Red Baron Karmen 20356G 20355G Kadavan 20354G 4172 Rose 20352G Sweet savannah 4128 XPH 6068 XPH 6023 4101 4157 4122 XPH 6022 4144 TG1015Y XPH 6028 20275G 20277G 4155 4018 TG502 Granex 33 Granex 429 20270G 4143 4130 4141 4120 20272G 4143 4149 Henry special 4146 4122 20303G 20291G 20274G 4127 4124 0001 20288G 20276G 20280G TG502 20290G 4135 20301G Rio Bravo 20253G 20330G Vidalia 20263G 20316G 20338G 20251G 20305G 20259G Albion 20223G 20319G 20240G Contessa 20234G 4168 20216G a contents 930 2549 202 157 153 150 141 719 158 286 286 214 207 179 175 159 157 153 150 150 150 146 145 141 140 139 138 137 137 136 136 135 128 126 124 123 119 116 111 110 108 107 105 100 98 96 95 95 94 93 87 87 85 81 80 77 76 74 74 71 70 50 1 1 <1 <1 <1 <1 <1 ref Red 69 35 83 83 83 83 83 Pink 69 83 Yellow 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 83 White 69 83 83 83 83 83 83 83 cultivar Red Bone Tropea Tropea rossa Rossa Lilia Redwing Morada de Amposta contents 117 390 763 487 582 943 ref 83 63 80 80 80 60 20366G 20357G 20249G 20257G 4145 447 947 935 Hyper Hygro Topaz Superba Rff Nirvana DPS 1032 Yellow 2025 King-Midas SBO 133 Walla Walla Carmen Hybrid Sweet Spanish Hybrid Sweet Spanish Utah Yellow Globe Hybrid Early Yellow Globe Rijnsburger Vsetana Festival Tamara Daytona Dorata Density Castillo Santana Kitamiko Toyohira Kitawase3 Tsukisappu Superkitamomiji CS3–12 Tsukiko22 2935A K83211 Tamara Predator RioRita RNX 10968 Barito Hyskin Summit MSU 826 MSU 2935 MSU 1459 MSU 1654 MSU 4921 MSU4535 20304G 20215G 20221G Ala Gladstone Southport White Hawk 128 118 68 56 54 294 365 282 333 361 326 228 350 217 524 482 133 122 26 59 62 61 25 15 814 1831 526 617 933 979 786 749 292 359 213 366 367 331 436 396 398 145 158 223 276 251 234 221 276 332 394 501 608 1285 <1 <1 <1 180 2 3 1 83 83 83 83 83 29 29 29 29 29 29 29 29 40 40 40 40 40 66 66 66 66 66 66 69 35 80 80 80 80 80 80 86 86 86 86 86 86 86 86 86 35 35 35 35 96 96 96 97 97 97 97 97 97 83 83 83 35 80 80 80 For comparison. No. flavonol content reported as quantities of flavonoid glycosides in the orginal publications have been converted to quantities of the corresponding aglycones. Food Chem. Agric. 25. 2007 10077 Table 4. 55.

Trueman. 2006. Yellow 2025. (9) Hirota. S.. 1998. and white). 603–615. Review: The analysis of onion and garlic. Tables 4and 5 display the reported flavonol content of a range of cultivars from several individual reports. 2000. 25. J. CRC Taylor & Francis: Boca Raton. Yoo. Hobbs. 607–617.5 mg · kg-1 FW quercetin. (3) Brewster. Identification of the fourth allele of the ANS (anthocyanidin synthase) gene and its effect on red color intensity in onions (Allium cepa). Chemistry.. the yellow cultivars.. T. Med. heart disease. K. 255–263. Crowther. reveals the largest variation. B. U. Red cultivars generally contain quite high flavonoid quantities.. (13) Fossen. (5) Masuzaki. FL. The flavonoids were mainly made up of quercetin and isorhamnetin in the form of aglycones and glycosides. cultivars. The content of free quercetin in all these onion cultivars was low (<0. J. Phytother.. S. 434.). J. 149.10078 J. Jr. 46. while white cultivars contain very low amounts of flavonols. (6) Masuzaki. Occurrence of quercetin in the outer skins of the bulb of the onion. Banthorpe. 52. 69. 1.4 mg · kg-1).a global benefit to health. England.. M. No. were analyzed for flavonoid content based on the aglycones as released upon acid hydrolysis. followed by myricetin (28–41 mg · kg-1 FW). the world’s genetic onion resources may represent a huge potential for utilization of flavonoid selection of targeted productions of onion cultivars that possess naturally high concentrations of flavonoids.... Mol... (7) Kim. T. A. pink. The effects of plant flavonoids on mammalian cells: implications for inflammation. pink. (8) Takahama. G. total quercetin content in yellow. Eds. and landraces exist. M. quercetin was the major flavonol aglycone (77–463 mg · kg-1 FW) derived from all cultivars. S. M. (10) Griffiths. J. In Natural Products. Mann. J. Bang. J. The highest amount of free quercetin was detected in the fresh bulbs of “Tropea rossa tonda” (557. Hummel. Quantitative Contents of Specific Flavonoid Structures (mg · kg-1 FW) in Different Onion Cultivars cultivar Karmena Pòvoa red Red Baron Rose Red Baronb unspecific Tropea Rossa Rossa Lilia Redwing Vsetanaa Rijnsburger Cross Bowb unspecific Festival Tamara Daytona Dorata Density Castillo Santana Kitamiko27 Toyohira Kitawase3 Tsukisappu Superkitamomiji CS3–12 Tsukiko22 2935A K83211 Baritoc Hyskinc Summitc Alaa Pòvoa white Albion Gladstone Southport White Hawk que 3. 2005. 16. Andersen. 81. 3497–3502. 2006. yellow. J. Their chemistry and biological significance. Review: On the occurrence of flavonol and flavone glycosides in vegetables.-Unters.4′-diglc rutin Red 157 261 1375 1052 1001 410 11 33 30 que 4′-glc 32234 353 394 302 889 350 126 352 419 23283 360 653 130 374 460 713 725 611 547 254 355 172 344 343 304 364 392 347 337 334 281 265 147 36 1 2 1 que 163 1 9 15 17 20 558 58 77 56 39 29 10 56 67 112 95 65 92 ref 35 37 69 69 70 71 80 80 80 35 69 70 71 80 80 80 80 80 80 86 86 86 86 86 86 86 86 86 96 96 96 35 37 69 80 80 80 2 3 2 Yellow 64 1117 504 170 43 38 41 73 51 49 263 266 208 294 297 276 412 290 356 177 180 157 2 5 6 14 9 6 White 15 109 50 1 0 3 1 1 1 a Reported as mg kg-1 DW. Shimoda. B. Spectroscopic techniques applied to flavonoids. as contents vary from very low to very high. Onions ... Kandaswami. T. 186. Pharmacol.. B. E. 45–51. E. 1–5. Shigyo.. Vol. 1994. U. S. Tissue and spatial distribution of flavonol and peroxidase in onion bulbs and stability of flavonol glucosides during boiling of the scales... Thomas. 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