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Thiolysis-HPLC analysis of proanthocyanidins
in health foods and their materials |
Ye LI,Huiling LI,Tong CUI, |
College of Food Science
and Technology, Agricultural University of Hebei, Baoding 071001,
China; |
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Abstract Proantocyanidins (PCs) found in plant products, are reported to be beneficial to human health. A thiolysis-HPLC method was developed to determine PC in health foods and the basic PC material, grape seed extract (GSE). PCs were quantitatively resolved by acid-catalysis in the presence of benzyl mercaptan as nucleophiles. The reaction solutions of actual purchased products were injected into an HPLC and the gallic acid (GA), catechin (CT), epicatechin (EC), epicatechin gallate (ECG), epicatechin benzyl sulfide (EC-S), and epicatechin gallate benzyl sulfide (ECG-S) were separated and detected. The HPLC was performed on a Hypersil BDS C18 (4.6 mm id × 250 mm, 5 μm) column at 35°C, formic acid (0.05%) was employed as mobile phase A, and methanol ∶ acetonitrile= 1∶2 (v/v) was employed as mobile phase B. The flow rate of gradient elution was 0.8 mL·min−1, and the DAD detection was carried out at 280 nm. The relative standard deviation of CA, CT, EC, ECG, EGS and ECG-S followed by repeated reactions and injections were between 0.4%–4.2%, and the PC levels in six health foods were between 6.9–161.3 mg·g−1 with the mean degree of polymerization (mDP) 2.2–4.2. In a GSE product, the PC content was 531.4 mg·g−1, and the mDP was 9.0, which although higher than other products tested, was far below the labeled, claimed, concentration. Data showed this method to be accurate and sensitive and can be used for the quality evaluation of actual health products containing PC components.
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Issue Date: 05 September 2010
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Bate-Smith E C (1975). Phytochemistry of proanthocyanidins. Phytochemistry, 14(4): 1107–1113
doi: 10.1016/0031-9422(75)85197-1
|
|
Dueñas M, Sun B, Hernández T, Estrella I, Spranger M I (2003). Proanthocyanidin composition in the seed coat of lentils(Lens culinaris L.). J Agric Food Chem, 51(27): 7999–8004
doi: 10.1021/jf0303215
|
|
Fulcrand H, Remy S, Ouguet J M (1999). Study of wine tannin oligomers by on-line liquid chromatography electro-spray ionizationmass spectrometry. J Agric Food Chem, 47(3): 1023–1028
doi: 10.1021/jf9805496
|
|
Gu L, Kelm M, Hammerstone J F, Beecher G, Cunningham D, Vannozzi S, Prior R L (2002). Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selectedfoods with an optimized normal-phase HPLC-MS fluorescent detectionmethod. J Agric Food Chem, 50(17): 4852–4860
doi: 10.1021/jf020214v
|
|
Guyot S, Marnet N, Drilleau J (2001). Thiolysis-HPLC characterization of apple procyanidins covering a large range of polymerizationstates. J Agric Food Chem, 49(1): 14–20
doi: 10.1021/jf000814z
|
|
Hertog M G, Kromhout D, Aravanis C, Blackburn H, Buzina R, Fidanza F, Giampaoli S, Jansen A, Menotti A, Nedljkovic S (1995). Flavonoid intake and long-term risk of coronary heart disease and cancer in seven countries study. Arch Intern Med, 155(4): 381–386
doi: 10.1001/archinte.155.4.381
|
|
Karonen M, Leikas A, Loponen J, Sinkkonen J, Ossipov V, Pihlaja K (2007). Reversed-phase HPLC-ESI/MS analysis of birch leaf proanthocyanidins after their acidicdegradation in the presence of nucleophiles. Phytochem Anal, 18(5): 378–386
doi: 10.1002/pca.992
|
|
Kennedy J A, Jones G P (2001). Analysis of proanthocyanidin cleavage products following acid-catalysisin the presence of excess phloroglucinol. J Agric Food Chem, 49(4): 1740–1746
doi: 10.1021/jf001030o
|
|
Knekt P, Kumpulainen J, Järvinen R, Rissanen H, Heliövaara M, Reunanen A, Habulinen T, Aromaa A (2002). Flavonoid intake and risk of chronic disease. Am J Clin Nutr, 76(3): 560–568
|
|
Kozikowski A P, Tuckmantel W, George C (2000). Studies in polyphenol chemistry and bioactivity. 2. Establishment of interflavanlinkage regio- and stereochemistry by oxidative degradation of anO-alkylation derivative of procyanidin B2 to (R)-(-)-2,4-diphenylbutyric acid. J Org Chem, 65(17): 5371–5381
doi: 10.1021/jo000485+
|
|
Labarbe B, Cheynier V, Brossaud F, Souquet J M, Moutounet M (1999). Quantitative fractionation of grape proanthocyanidinsaccording to their degree of polymerization. J Agric Food Chem, 47(7): 2719–2723
doi: 10.1021/jf990029q
|
|
Ou B, Hampsch-Woodill M, Flanagan J, Deemer E K, Prior R L, Huang D (2002). Novel fluorometric assay for hydroxyl radical prevention capacity using fluoresceinas the probe. J Agric Food Chem, 50(10): 2772–2777
doi: 10.1021/jf011480w
|
|
Porter L J, Hrstich L N, Chan B G (1986). The conversion of procyanidins and prodelphinidins to cyanidin and delphindin. Phytochemistry, 25(1): 223–230
doi: 10.1016/S0031-9422(00)94533-3
|
|
Rigaud J, Escribano-Bailon M T, Prieur C, Souquet J M, Cheynier V (1993). Normal-phase high-performance liquid chromatographicseparation of procyanidin from cacao beans and grape seeds. J Chromatogr A, 654(2): 255–260
doi: 10.1016/0021-9673(93)83368-3
|
|
Svedstrom U, Vuorela H, Kostiainen R (2002). High-performance liquid chromatographic determination of oligomeric procyanidins fromdimers up to the hexamer in hawthorn. J Chromatogra A, 968(1―2): 53–60
doi: 10.1016/S0021-9673(02)01000-2
|
|
Thompson R S, Jacques D, Haslam E, Tanner R J N (1972). Plant proanthocyanidins. part I. Introduction, the isolation, structure, and distribution in natureof plant procyanidins. J Chem Soc PerkinTrans, 1: 1387–1399
doi: 10.1039/p19720001387
|
|
Vidal S, Meudec E, Cheynier V, Skouroumounis G, Hayasaka Y (2004). Mass spectrometric evidence for the existence of oligomericanthocyanins in grape skins. J Agric Food Chem, 52(23): 7144–7151
doi: 10.1021/jf048939h
|
|
Wojdyło A, Oszmiański J, Laskowski P (2008). Polyphenolic compounds and antioxidant activity of new and old apple varieties. J Agric Food Chem, 56(15): 6520–6530
doi: 10.1021/jf800510j
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