HPLC-MS analysis of proanthocyanidin oligomers and other phenolics in 15 strawberry cultivars.

The phenolic compounds of 15 strawberry cultivars grown in Spain were analyzed and quantified: anthocyanins (20.2-47.4 mg/100 g of fw) (cyanidin 3-glucoside and pelargonidin 3-glucoside, 3-rutinoside, and 3-malonyl glucoside), flavonols (1.5-3.4 mg/100 g of fw) (quercetin 3-glucuronide and kaempferol 3-glucoside and 3-p-coumaroyl-glucoside), proanthocyanidins (53.9-163.2 mg/100 g), p-coumaroyl-glucose (0.84-6.70 mg/100 g), ellagitannins (9.67-22.86 mg/100 g) (sanguiin H-6, lambertianin C, and galloyl bis-HHDP-glucose), and ellagic acid glycosides (0.88-2.06 mg/100 g of fw) (two ellagic acid deoxyhexosides). Proanthocyanidins, the main phenolic compounds, were characterized by phloroglucinol degradation. Their mean degree of polymerization ranged from 3.4 for cv. Chiflon to 5.8 for cv. Ventana, the average value being 4.3. The terminal unit of proanthocyanidin oligomers was always (epi)catechin (17.36-29.93%) and (epi)catechin (61.66-75.39%) or (epi)afzelechin (4.50-10.54%) as extension units. Different combinations of (epi)catechin and (epi)afzelechin were detected, and their sequence of linkage was characterized by HPLC-MS-MS. Relative percentages of dimers, trimers, tetramers, and pentamers were evaluated by the extracted ion chromatogram (EIC) analysis.

[1]  Jessica Nilsson,et al.  Antioxidants, low molecular weight carbohydrates, and total antioxidant capacity in strawberries (Fragaria x ananassa): effects of cultivar, ripening, and storage. , 2004, Journal of agricultural and food chemistry.

[2]  A. Wojdyło,et al.  Effect of drying methods with the application of vacuum microwaves on the bioactive compounds, color, and antioxidant activity of strawberry fruits. , 2009, Journal of agricultural and food chemistry.

[3]  R. Törrönen,et al.  Sources and Health Effects of Dietary Ellagitannins , 2009 .

[4]  F. Tomás-Barberán,et al.  The use of acetone as an extraction solvent for anthocyanins from strawberry fruit , 1998 .

[5]  P. Kroon,et al.  High contents of nonextractable polyphenols in fruits suggest that polyphenol contents of plant foods have been underestimated. , 2009, Journal of agricultural and food chemistry.

[6]  C. Fraga,et al.  Influence of oligomer chain length on the antioxidant activity of procyanidins. , 2000, Biochemical and biophysical research communications.

[7]  F. Lajolo,et al.  Bioactive compounds and quantification of total ellagic acid in strawberries (Fragaria x ananassa Duch.) , 2008 .

[8]  S. Hannum.  Potential Impact of Strawberries on Human Health: A Review of the Science , 2004, Critical reviews in food science and nutrition.

[9]  A. Törrönen,et al.  High-performance liquid chromatography (HPLC) analysis of phenolic compounds in berries with diode array and electrospray ionization mass spectrometric (MS) detection: ribes species. , 2003, Journal of agricultural and food chemistry.

[10]  Shiow Y. Wang,et al.  Cultural system affects fruit quality and antioxidant capacity in strawberries. , 2002, Journal of agricultural and food chemistry.

[11]  J. Rivas-Gonzalo,et al.  Quantitative analysis of flavan-3-ols in Spanish foodstuffs and beverages. , 2000, Journal of agricultural and food chemistry.

[12]  M. Heinonen.  Antioxidant activity and antimicrobial effect of berry phenolics--a Finnish perspective. , 2007, Molecular nutrition & food research.

[13]  David Haytowitz,et al.  Screening of foods containing proanthocyanidins and their structural characterization using LC-MS/MS and thiolytic degradation. , 2003, Journal of agricultural and food chemistry.

[14]  R. Wrolstad,et al.  Phenolic composition and antioxidant activities in flesh and achenes of strawberries (Fragaria ananassa). , 2005, Journal of agricultural and food chemistry.

[15]  N. Seeram.  Berry fruits for cancer prevention: current status and future prospects. , 2008, Journal of agricultural and food chemistry.

[16]  J. A. Teixeira,et al.  Comparative Study of Selva and Camarosa Strawberries for the Commercial Market , 2002 .

[17]  Gary Williamson,et al.  Bioavailability and bioefficacy of polyphenols in humans. I. Review of 97 bioavailability studies. , 2005, The American journal of clinical nutrition.

[18]  A. J. Meléndez-Martínez,et al.  Assessment of the differences in the phenolic composition of five strawberry cultivars (Fragaria x ananassa Duch.) grown in two different soilless systems. , 2007, Journal of agricultural and food chemistry.

[19]  G. Beecher,et al.  Fractionation of polymeric procyanidins from lowbush blueberry and quantification of procyanidins in selected foods with an optimized normal-phase HPLC-MS fluorescent detection method. , 2002, Journal of agricultural and food chemistry.

[20]  K. Başer,et al.  Phenolic composition of strawberry genotypes at different maturation stages. , 2004, Journal of agricultural and food chemistry.

[21]  A. Törrönen,et al.  Contents of anthocyanins and ellagitannins in selected foods consumed in Finland. , 2007, Journal of agricultural and food chemistry.

[22]  A. Törrönen,et al.  Content of the flavonols quercetin, myricetin, and kaempferol in 25 edible berries. , 1999, Journal of agricultural and food chemistry.

[23]  M. Kelm,et al.  High-performance liquid chromatography separation and purification of cacao (Theobroma cacao L.) procyanidins according to degree of polymerization using a diol stationary phase. , 2006, Journal of agricultural and food chemistry.

[24]  J. Kennedy,et al.  Analysis of proanthocyanidin cleavage products following acid-catalysis in the presence of excess phloroglucinol. , 2001, Journal of agricultural and food chemistry.

[25]  David Heber,et al.  Identification of phenolic compounds in strawberries by liquid chromatography electrospray ionization mass spectroscopy , 2005 .

[26]  A. Törrönen,et al.  Identification and quantification of phenolic compounds in berries of Fragaria and Rubus species (family Rosaceae). , 2004, Journal of agricultural and food chemistry.

[27]  A. Törrönen,et al.  Content of flavonols and selected phenolic acids in strawberries and Vaccinium species: influence of cultivar, cultivation site and technique , 2000 .

[28]  J. Rivas-Gonzalo,et al.  Anthocyanin pigments in strawberry , 2007 .

[29]  M. Gil,et al.  Changes in strawberry anthocyanins and other polyphenols in response to carbon dioxide treatments , 1997 .

[30]  P. Bridle,et al.  Strawberry juice colour: A study of the quantitative and qualitative pigment composition of juices from 39 genotypes , 1994 .