Determination of Anthocyanidins in Berries and Red Wine by High-Performance Liquid Chromatography

Nyman, N.A.; Kumpulainen, Jorma

doi:10.1021/jf010572i

Cited by 136 publications

(98 citation statements)

References 29 publications

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“…1; Bohm, 1998). In strawberry, flavonols kaempferol and quercetin are found, and pelargonidin is the main anthocyanidin (Häkkinen and Tö rrö nen, 2000;Nyman and Kumpulainen, 2001). To further analyze this observation, and to combine the present information, we assembled a table of flavonol and anthocyanidin contents a Refer to peak numbers and retention times (R t ) in Figure 6.…”

Section: Discussionmentioning

confidence: 99%

Expression of Genes Involved in Anthocyanin Biosynthesis in Relation to Anthocyanin, Proanthocyanidin, and Flavonol Levels during Bilberry Fruit Development

Määttä²,

et al. 2002

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The production of anthocyanins in fruit tissues is highly controlled at the developmental level. We have studied the expression of flavonoid biosynthesis genes during the development of bilberry (Vaccinium myrtillus) fruit in relation to the accumulation of anthocyanins, proanthocyanidins, and flavonols in wild berries and in color mutants of bilberry. The cDNA fragments of five genes from the flavonoid pathway, phenylalanine ammonia-lyase, chalcone synthase, flavanone 3-hydroxylase, dihydroflavonol 4-reductase, and anthocyanidin synthase, were isolated from bilberry using the polymerase chain reaction technique, sequenced, and labeled with a digoxigenin-dUTP label. These homologous probes were used for determining the expression of the flavonoid pathway genes in bilberries. The contents of anthocyanins, proanthocyanidins, and flavonols in ripening bilberries were analyzed with high-performance liquid chromatography-diode array detector and were identified using a mass spectrometry interface. Our results demonstrate a correlation between anthocyanin accumulation and expression of the flavonoid pathway genes during the ripening of berries. At the early stages of berry development, procyanidins and quercetin were the major flavonoids, but the levels decreased dramatically during the progress of ripening. During the later stages of ripening, the content of anthocyanins increased strongly and they were the major flavonoids in the ripe berry. The expression of flavonoid pathway genes in the color mutants of bilberry was reduced. A connection between flavonol and anthocyanin synthesis in bilberry was detected in this study and also in previous data collected from flavonol and anthocyanin analyses from other fruits. In accordance with this, models for the connection between flavonol and anthocyanin syntheses in fruit tissues are presented.Fruit development from flower to ripe fruit is a complex process that involves modification of cellular compartments, loss of cell wall structure causing softening, and accumulation of carbohydrates (Brady, 1987). The production of secondary metabolites during the ripening process is an essential phenomenon for the contribution of seed dispersal of the plant in the form of accumulation of pigments and flavor compounds. The significance of secondary products in defense against diseases in developing fruits should also be remembered (Harborne, 1997;Mercier, 1997).Flavonoids are a large group of phenolic secondary metabolites that are widespread among plants and are involved in many plant functions. Anthocyanins, a flavonoid subclass, are the main pigments in flowers and fruits, acting as insect and animal attractants (Bohm, 1998;Harborne and Williams, 2000). Anthocyanins are synthesized via the phenylpropanoid pathway (Fig. 1). Anthocyanin biosynthesis has been extensively studied in several plant species, and, therefore, detailed information of the course of reactions is available. Two classes of genes are required for anthocyanin biosynthesis, the structural genes encoding the enzymes...

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Section: Discussionmentioning

confidence: 99%

Expression of Genes Involved in Anthocyanin Biosynthesis in Relation to Anthocyanin, Proanthocyanidin, and Flavonol Levels during Bilberry Fruit Development

Määttä²,

et al. 2002

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“…In order to obtain the most adequate colour for each foodstuff, some additives are usually employed in their processing (Alcalde-Eon et al 2004). Anthocyanins are a group of natural flavonoids responsible for the red, violet and blue colours of berries and fruits (Nyman & Kumpulainen 2001;Tian et al 2006). As the common antioxidants, anthocyanins may have health benefits in the prevention of chronic and degenerative diseases including heart diseases and cancer (Wu & Prior 2005;Chen et al 2006).…”

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confidence: 99%

Separation and character analysis of anthocyanins from mulberry (Morus alba L.) pomace

Zhang¹,

He²,

QiuHong³

et al. 2011

Czech J. Food Sci.

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Zhang W., He J., Pan Q., Han F., Duan C. (2011): Separation and character analysis of anthocyanins from mulberry (Morus alba L.) pomace. Czech J. Food Sci., 29: 268-276.Mulberry pomace, as a by-product of juice and wine making, was investigated as a potential source of natural anthocyanins. The results showed that anthocyanin contents in mulberry pomace from two varieties were above 250 mg/100 g, that is 74%-79% of that in mulberry whole fruit. Thus, mulberry pomace could be a potential anthocyanins source. The anthocyanins in mulberry pomace had an attractive red colour with the chroma at 5.0 and hue angle at 6.8. Five anthocyanins were identified in mulberry pomace, cyanidin-3-glucoside and cyanidin-3-rutinoside being the major anthocyanins. The method of the separation of the two anthocyanins was studied showing that both anthocyanins with purities above 98% could be well separated on Sephadex LH-20 by eluting with 10% ethanol containing 1% of acetic acid after purification with AB-8 macroporous resin. The recovery of the complete process of both anthocyanins was 57.4%. Cyanidin-3-glucoside and cyanidin-3-rutinoside had more attractive colours and strong antioxidant activities and could be used as potential food colourants and antioxidants.

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“…Little is known about differences in biological potency between individual anthocyanins including their metabolic conjugates, and it is conceivable that methylpetunidin-3-arabinoside or dimethyldelphinidin-3-arabinoside, the major metabolite(s) identified here in colorectal tissue after mirtocyan consumption, may constitute one of several anthocyanin species responsible for pharmacodynamic effects. Comparison of the doses of mirtocyan used here with consumption of anthocyanins in the diet suggests that the 1.4-gram dose containing ∼0.5 gram anthocyanins equates to ∼370 grams fresh bilberries (23). Average daily consumption of anthocyanins with the Western diet has been estimated at around a fifth of that amount (∼100 mg; refs.…”

Section: Discussionmentioning

confidence: 94%

Pilot Study of Oral Anthocyanins for Colorectal Cancer Chemoprevention

Thomasset

Berry

Cai

et al. 2009

Cancer Prevention Research

114

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Naturally occurring anthocyanins possess colorectal cancer chemopreventive properties in rodent models. We investigated whether mirtocyan, an anthocyanin-rich standardized bilberry extract, causes pharmacodynamic changes consistent with chemopreventive efficacy and generates measurable levels of anthocyanins in blood, urine, and target tissue. Twenty-five colorectal cancer patients scheduled to undergo resection of primary tumor or liver metastases received mirtocyan 1.4, 2.8, or 5.6 grams (containing 0.5-2.0 grams anthocyanins) daily for 7 days before surgery. Bilberry anthocyanins were analyzed by high performance liquid chromatography (HPLC) with visible or mass spectrometric detection. Proliferation was determined by immunohistochemistry of Ki-67 in colorectal tumor. Concentrations of insulin-like growth factor (IGF)-I were measured in plasma. Mirtocyan anthocyanins and methyl and glucuronide metabolites were identified in plasma, colorectal tissue, and urine, but not in liver. Anthocyanin concentrations in plasma and urine were roughly dose-dependent, reaching ∼179 ng/gram in tumor tissue at the highest dose. In tumor tissue from all patients on mirtocyan, proliferation was decreased by 7% compared with preintervention values. The low dose caused a small but nonsignificant reduction in circulating IGF-I concentrations. In conclusion, repeated administration of bilberry anthocyanins exerts pharmacodynamic effects and generates concentrations of anthocyanins in humans resembling those seen in Apc Min mice, a model of FAP adenomas sensitive to the chemopreventive properties of anthocyanins. Studies of doses containing <0.5 gram bilberry anthocyanins are necessary to adjudge whether they may be appropriate for development as colorectal cancer chemopreventive agents.

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Determination of Anthocyanidins in Berries and Red Wine by High-Performance Liquid Chromatography

Cited by 136 publications

References 29 publications

Expression of Genes Involved in Anthocyanin Biosynthesis in Relation to Anthocyanin, Proanthocyanidin, and Flavonol Levels during Bilberry Fruit Development

Expression of Genes Involved in Anthocyanin Biosynthesis in Relation to Anthocyanin, Proanthocyanidin, and Flavonol Levels during Bilberry Fruit Development

Separation and character analysis of anthocyanins from mulberry (Morus alba L.) pomace

Pilot Study of Oral Anthocyanins for Colorectal Cancer Chemoprevention

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