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Compositions of Anthocyanin and Other Flavonoids in Cultured Cells of Rabbiteye Blueberry (Vaccinium Ashei Reade Cv

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Compositions of Anthocyanin and Other Flavonoids in Cultured Cells of Rabbiteye Blueberry (Vaccinium Ashei Reade Cv Food Sci. Technol Res., 10 (3), 239-246, 2004 Compositions of Anthocyanin and Other Flavonoids in Cultured Cells of Rabbiteye Blueberry (Vaccinium ashei Reade cv. Tiiblue) Shioka HAMAMATSU,Kimiko YABE and Yoshihiko NAWA National Food Research Institute, 2-1-12 Kannondai, Tsukuba, Ibaraki 305-8642, Japan Received August 18, 2003 ; Accepted April 2, 2004 Our blueberry cultured cells produce anthocyanins in high quantity (Nawa et al., Biosci. Biotech. Biochem., 57, 770-774, 1993). Using high performance liquid chromatography/mass spectrometry (LC-MS), 14 anthocyanins in the red cells derived from leaves of rabbiteye blueberry cv. Tifblue (Vaccinium ashei Reade) were identified as 3-galactoside (gal), 3-glucoside (glc) and 3-arabinoside (ara) of cyanidin (Cy), delphinidin (Dp), petunidin (Pe), peonidin (Pn) and malvidin (Mv), except for Mv 3-ara. The fruits additionally contained 15 anthocyanins and Mv 3-ara, as a main anthocyanin. The autumn red leaves contained Cy 3-gal, Cy 3-ara and Cy 3-glc. In the red cells and the leaves, derivatives of Cy were the most abundant at 85.7% (Cy 3-gal 49.1%, Cy 3-glc 5.8%, Cy 3-ara 30.9%) and 100% (Cy 3-gal 51.0%, Cy 3-glc 6.5%, Cy 3-ara 42.5%) of the total anthocyanins, respectively. In contrast, the fruits contained Mv derivatives as main components that amounted to 50.9% of the total anthocyanins; Mv 3-gal, Mv 3-ara and Mv 3-glc constituted 21.2, 15.3 and 14.4%, respectively. Cy derivatives in fruit anthocyanins amounted to 18.0% . The red cells produced 107 mg of anthocyaninlIOO g fr wt, which was slightly lower than that of the fruits (129 mg). LC-MS analysis also suggested the presence of quercetin (Q) 3-glc, Q 3-rutinoside, and glycosides of myricetin (M) and Q in the red cells. This analysis showed the presence of (+)-catechin (C) and (-)-epicatechin (EC) in these cells as well as of (+)- C, (-)-EC and chlorogenic acid in the red leaves. These flavonoids and phenolics were also some of the main components in the leaves. Keywords: blueberry, cultured cell, anthocyanins, phenolics, flavonols, LC-MS. Introduction are usually used as a food colorant providing additional Flavonoids are polyphenolic phytochemicals that con- benefits for health. Furthermore, ethanol extracts of stitute a large group of secondary metabolites in plants, and highbush blueberry leaves are approved as food antioxi- are useful diet components. Dietary flavonoids consist dants in Japan, the leaves were reported to contain a higher mainly of anthocyanins, flavonols, flavones, catechins and level of many flavonols including quercetin glycosides than flavanones; they are potent antioxidants, free radical scav- the fruits (Ehlenfeldt & Prior, 2001). Quercetin is one of engers and metal chelators. Thus, certain flavonoids are used the most extensively studied flavonoids because of its bio- for their health promoting properties. Anthocyanins from 10gical properties including the antioxidant activity. the fruit of bilberry (Vaccinium myrtillus) were reported to Production of useful secondary metabolites by plant cells have the ability to decrease the permeability and fragility and tissue cultures is a matter of interest in food biotech- of capillaries, to inhibit urinary tract infection and to nology. Anthocyanin production was reported for the strengthen collagen matrices via cross linkages (Morazzoni cultured cells of grape (Yamakawa et al., 1983, Do & & Bombardelli, 1996; Walt & Dufour, 1997). Pharmaceutical Cormier, 1991), blueberry (Nawa et al., 1993), cranberry preparations of crude extracts of the fruits, including mainly (Vaccinium macrocarpon Ait) (Madhavi et al., 1995), anthocyanins, are used for curing. In the United States, blue- bilberry (Madhavi et al., 1998), strawberry (Asano et al., berries have become of special interest in connection with 2002) and Vaccinium pahalae (Meyer et al., 2002). Koda studies on the total antioxidant activities in food using the et al. reported formation of blue pigment by Clerodendron automated oxygen radical absorbance capacity (ORAC) trichotomum callus (1992), and formation of red pigment procedure; this is because of the high antioxidant capacity by perilla and their utilization as food colors (1993). of blueberry anthocyanins and the wide range of their antho- Formation of crocin by gardenia callus (Nawa & Ohtani, cyanin and flavonol content (Prior et al., 1998; Ehlenfeldt 1992), of lutein and zeaxanthin by bilberry (Madhavi et al., & Prior, 2001). In Japan, anthocyanins of blueberry fruits 1998), and of proanthocyanidins by blueberry cells (Nawa et al., 1993) also were reported. This cell line of blueber- ry showed many kinds of anthocyanins and other flavonoids, E-mail: [email protected]. jp although they were not identified in detail. We used liquid 240 S. HAMAMATSU et al. chromatography - mass spectrometry (LC-MS) technique Co., Milford, Massachusetts) and the whole was washed for analyses of flavonoids in cultured red cells, fruits, and with 1.5 ml of 1% formic acid three times. The adsorbed leaves of rabbiteye blueberry cv. Titblue. pigments were eluted with l(~o formic acid-methanol, and In this work, we describe the identification of antho- the eluates were used as crude extracts for further analysis. cyanins, flavonols and other phenolics compounds in these Semi-preparative HPLC of anthocyanins The crude cultured cells, fruits, and leaves of rabbiteye blueberry cv. extract from commercial fruits was applied onto a Shim- Tiiblue and demonstrate the parallel ability of cell cultures pack PRC-ODS (H) column (200 x 250 mm, Shimadzu, to produce the same flavonoids in vitro. Tokyo) connected to a guard column (Shim-pack GPRC- ODS, 15 x 15 mm) by eluting with a linear gradient of water- Materials and Methods acetonitrile-methanol-formic acid (40:22.5 :22.5 : 10, v/v) in Chemicals Authentic Cy 3-glc, Cy 3-gal, Mv 3-glc, water-formic acid (90:10, v/v) from an initial 10 to 60% Peo 3-glc, hesperidin, quercetin (Q) 3-glc, Q 3-rhamnoside for 40 min at a flow rate of 1.3 ml/min at 25'C, followed (rha), Q 3-rutinoside (rutin), kaempferol (K) 3-glc, and by an elution with a gradient from 60 to 80% for the next myricetin (M) 3-rham were purchased from Extrasynthase 3 min. Resultant eluates were used as standard anthocyanin S. A. (Impasse Jacquard, Genay, France). (+)-catechin ((+)- samples for analytical HPLC and LC-MS analyses. C), (-)-epicatechin ((-)-EC) were from Kurita Kogyo Co. Hydrolysis of anthocyanins and TLC of sugar moiety (Tokyo), and chlorogenic acid was from Sigma Chemical Anthocyanin samples after semi-preparative HPLC were Co. (St. Louis, MO). fully hydrolyzed with 2M HCI for 30 min at 100'C, and the Plant materials Rabbiteye blueberry (Vaccinium resulting sugar moiety was analyzed with a cellulose thin- ashei Reade cv. Titblue) was planted at the Agricultural and layer (0.1 mm thickness, 10 x 20 cm, Merck KGaA, Forestry Research Center, University of Tsukuba. Fruits and Darmstadt, Germany) with a solvent mixture of ethyl autumn red leaves were harvested in July 2001 and acetate-pyridine-water (40: 1 1 :6, v/v), then compared with December 2000, respectively. Fruits on the market also the authentic rhamnose, xylose, arabinose, glucose and were used to prepare anthocyanins as a standard sample. galactose, according to the method described by Asano et Samples were usually frozen and stored at -20'C until al. (2002). assayed. Analytical HPLC of anthocyanins Anthocyanins in Red-cell suspension culture Red cells were derived the crude extracts were analyzed with a Shim-pack CLC- from a cell line of blueberry callus from young leaf sections ODS (M) column (4.5 x 250 mm, Shimadzu, Tokyo) con- of rabbiteye blueberry cv. Titblue which had been culti- nected to a guard column (Shim-pack CLC-GODS (4), 4.0 vated at a farm in Chiba city (Nawa et al., 1993). The cell x 100 mm) by eluting with a linear gradient of water-ace- line was maintained for over 10 years on Murashige-Skoog tonitrile-methanol-formic acid (40:22.5:22.5:10, v/v) in (MS) medium (pH 5.7) (Murashige & Skoog, 1962) sup- water-formic acid (90:10, v/v) from an initial 10 to 60% plemented with 0.2 mg/1 of 2,4-dichlorophenoxyacetic acid for 40 min at a flow rate of 1.0 ml/min at 25'C, followed (2, 4-D), 3% (w/v) sucrose, 0.2% (w/v) Gelrite (Wako Pure by an elution with a gradient from 60 to 80% for the next Chemical Industries, Ltd., Osaka) at 25'C under white flu- 3 min. Elution of anthocyanins was monitored at 530 nm. orescent light (2,000 Iux, 10 h). Suspension cultures of the Each anthocyanin content was calculated by area of the red cells were obtained by inoculation of red callus into 50 HPLC peak using Cy 3-glc as standard. Cy 3-glc is an ml of MS Iiquid medium supplemented with 0.2 mg/1 of 2, abundant component of many anthocyanin-producing 4-D, 3% sucrose, and followed by aeration with an orbital cultured cells and many autumn red leaves. motion shaker at 1 10 rpm at 25'C under white fluorescent LC-MS analysis of anthocyanins and other flavonoids light (2,000 Iux, 10 h). Five ml of cell suspension (about Anthocyanins and other flavonoids were analyzed by LC- 0.75 g fresh weight) was inoculated into the same fresh MS with Hitachi M-1200AP equipment using a Shim-pack medium and sub-cultured at 12-day intervals. Subculture CLC-ODS (M) column. The analytical conditions for the was repeated three times to obtain settled cultures. Cells mass spectrometry were as follows: atmospheric pressure (about 0.5 to I g fresh weight in 5 ml) from a settled culture chemical ionization (APCI) probe; positive ion mode; mul- were proliferated for 9 days at logarithmic phase.
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