Determination of proanthocyanidin A2 content in phenolic polymer isolates by reversed-phase high-performance liquid chromatography

Koerner, Jayma L.; Hsu, Victor L.; Lee, Jungmin; Kennedy, James A.

doi:10.1016/j.chroma.2008.12.086

Cited by 53 publications

(71 citation statements)

References 20 publications

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“…Thiolysis and pholoroglucinolysis are widely used to determine monomeric composition and average DP of PAC ( Waters, & Jones, 2001;Spencer et al, 2007;Tarascou et al, 2011) and have also been used to determine the presence of A-type interflavan bonds (Koerner, Hsu, Lee, & Kennedy, 2009;Tarascou et al, 2011). However there are several problems with these techniques that are unresolved.…”

Section: Discussionmentioning

confidence: 98%

Deconvolution of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry isotope patterns to determine ratios of A-type to B-type interflavan bonds in cranberry proanthocyanidins

et al. 2012

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Section: Discussionmentioning

confidence: 98%

Deconvolution of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry isotope patterns to determine ratios of A-type to B-type interflavan bonds in cranberry proanthocyanidins

et al. 2012

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“…Terminal units were slightly enriched in catechin compared with epicatechin, with the relative amount of epicatechin decreasing over development (37.4 mol % in S3 to 25.6 mol % in S8; Table III). A minor proportion of the fruit PAs had A-type interflavan linkages (Koerner et al, 2009) Table S4). The calculated mDP of the blueberry fruit PAs was relatively stable between S3 and S6 (7-7.5) and then increased to a maximum of 8.5 in S8 fruit (Fig.…”

Section: Quantification and Chemical Characterization Of Pasmentioning

confidence: 99%

“…PA terminal subunits were identified by comparison of HPLC-DAD retention times and absorbance spectra with commercially available flavan-3-ol standards. Phloroglucinol-PA adducts were identified by comparison of HPLC retention times with grape (Vitis vinifera) skin and cranberry (Vaccinium macrocarpon) fruit PA reaction products that have been characterized previously (Koerner et al, 2009). mDP and conversion yield were calculated according to the method of .…”

Section: Soluble Pa Quantification and Determination Of Pa Subunit Comentioning

confidence: 99%

“…For acid cleavage and phloroglucinol derivatization of the PA extracts, the method of Koerner et al (2009) was used with minor modifications. Briefly, the lyophilized semipurified PA powder (approximately 5 mg) was dissolved in a 1-mL solution of 0.1 N methanolic hydrochloric acid containing 100 g L 21 phloroglucinol and 10 g L 21 ascorbic acid.…”

Section: Soluble Pa Quantification and Determination Of Pa Subunit Comentioning

confidence: 99%

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Gene Expression and Metabolite Profiling of Developing Highbush Blueberry Fruit Indicates Transcriptional Regulation of Flavonoid Metabolism and Activation of Abscisic Acid Metabolism

Zifkin

Jin²,

Ozga³

et al. 2011

Plant Physiology

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Highbush blueberry (Vaccinium corymbosum) fruits contain substantial quantities of flavonoids, which are implicated in a wide range of health benefits. Although the flavonoid constituents of ripe blueberries are known, the molecular genetics underlying their biosynthesis, localization, and changes that occur during development have not been investigated. Two expressed sequence tag libraries from ripening blueberry fruit were constructed as a resource for gene identification and quantitative realtime reverse transcription-polymerase chain reaction primer design. Gene expression profiling by quantitative real-time reverse transcription-polymerase chain reaction showed that flavonoid biosynthetic transcript abundance followed a tightly regulated biphasic pattern, and transcript profiles were consistent with the abundance of the three major classes of flavonoids. Proanthocyanidins (PAs) and corresponding biosynthetic transcripts encoding anthocyanidin reductase and leucoanthocyanidin reductase were most concentrated in young fruit and localized predominantly to the inner fruit tissue containing the seeds and placentae. Mean PA polymer length was seven to 8.5 subunits, linked predominantly via B-type linkages, and was relatively constant throughout development. Flavonol accumulation and localization patterns were similar to those of the PAs, and the B-ring hydroxylation pattern of both was correlated with flavonoid-3#-hydroxylase transcript abundance. By contrast, anthocyanins accumulated late in maturation, which coincided with a peak in flavonoid-3-O-glycosyltransferase and flavonoid-3#5#-hydroxylase transcripts. Transcripts of VcMYBPA1, which likely encodes an R2R3-MYB transcriptional regulator of PA synthesis, were prominent in both phases of development. Furthermore, the initiation of ripening was accompanied by a substantial rise in abscisic acid, a growth regulator that may be an important component of the ripening process and contribute to the regulation of blueberry flavonoid biosynthesis.Highbush blueberry (Vaccinium corymbosum; Ericaceae) is one of the most economically important fruit crops in North America. Blueberry fruit have been the focus of much recent attention due to numerous reports of their positive effects on human health. These benefits are generally attributed to high levels of polyphenolics, in particular the flavonoids (Rasmussen et al., 2005). Highbush blueberries have one of the highest in vitro antioxidant capacities of any fruit or vegetable (Prior and Gu, 2005;Wu et al., 2006). The major health benefits linked to the consumption of blueberries include a reduced risk for cardiovascular (Basu et al., 2010) and neurodegenerative (Neto, 2007) diseases. Furthermore, experiments on rodents suggest that blueberry extracts may also prevent cancer, slow tumor growth, and reverse cognitive and behavioral deficits related to stroke and aging (Lau et al., 2005;Gordillo et al., 2009).The three common types of flavonoids that accumulate in blueberry fruit are the flavonols, anthocya-

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“…The chemical structures of the isolated flavonoids were determined spectroscopically by means of IR, EI/MS, FAB/MS and NMR data as shown in Figure 1. Compounds 1 -8 were identified as lindeglaucol (1), lindeglaucone (2), cilicicone B (3), tamarixetin 3-O-a-Lrhamnoside (4), procyanidin A2 (5), cinnamtannin B1 (6), cinnamtannin D1 (7) and procyanidin A1 (8) with confirmation by comparing their spectroscopic data with those in the literature (Nonaka et al 1983;Kamiya et al 2001;Son et al 2005;Ahmed & Al-Howiriny 2007;Koerner et al 2009;Tomochika et al 2011;Huh et al 2012). …”

Section: Phytochemistrymentioning

confidence: 96%

Flavonoids from Lindera glauca Blume as low-density lipoprotein oxidation inhibitors

Huh

Park

Kang

et al. 2014

Natural Product Research

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In order to identify antioxidant flavonoids from Lindera glauca Blume, we performed phytochemical analysis of L. glauca Blume heartwood and isolated eight flavonoids - lindeglaucol (1), lindeglaucone (2), cilicicone B (3), tamarixetin 3-O-α-L-rhamnoside (4), procyanidin A2 (5), cinnamtannin B1 (6), cinnamtannin D1 (7), and procyanidin A1 (8) - through repeated column chromatography over silica gel (SiO₂), octadecyl silica gel (ODS) and Sephadex LH-20. The chemical structures of compounds 1-8 were elucidated from spectroscopic data (NMR, IR and MS). The low-density lipoprotein oxidation inhibitory activities of the isolated compounds were evaluated in vitro by using the thiobarbituric acid reactive substances assay. Compounds 5-8 exhibited high inhibition activity, comparable to the positive control butyl hydroxyl toluene. Compounds 2 and 3 were slightly less active, while 1 and 4 expressed low activity.

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Determination of proanthocyanidin A2 content in phenolic polymer isolates by reversed-phase high-performance liquid chromatography

Cited by 53 publications

References 20 publications

Deconvolution of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry isotope patterns to determine ratios of A-type to B-type interflavan bonds in cranberry proanthocyanidins

Deconvolution of matrix-assisted laser desorption/ionization time-of-flight mass spectrometry isotope patterns to determine ratios of A-type to B-type interflavan bonds in cranberry proanthocyanidins

Gene Expression and Metabolite Profiling of Developing Highbush Blueberry Fruit Indicates Transcriptional Regulation of Flavonoid Metabolism and Activation of Abscisic Acid Metabolism

Flavonoids from Lindera glauca Blume as low-density lipoprotein oxidation inhibitors

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