Chemical reaction detection of catechins and proanthocyanidins with 4-dimethylaminocinnamaldehyde

Treutter, D.

doi:10.1016/s0021-9673(01)93963-9

Cited by 174 publications

(133 citation statements)

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“…The total flavan-3-ol content was determined using the pdimethylaminocinnamaldehyde (DMACA) assay which gives a highly specific reaction with catechin-type compounds and with procyanidins (Treutter, 1989). The assay was run as follows: 2350 L of methanol was mixed with 100 L DMACA-reagent (2.0 m/v% DMACA dissolved in methanol: 6 N H 2 SO 4 50:50 v/v solution) and with 20 L sample.…”

Section: Total Flavan-3-ol Contentmentioning

confidence: 99%

Antioxidant properties and detailed polyphenol profiling of European hornbeam (Carpinus betulus L.) leaves by multiple antioxidant capacity assays and high-performance liquid chromatography/multistage electrospray mass spectrometry

Hofmann

Nebehaj

Albert

2016

Industrial Crops and Products

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a b s t r a c tAccording to recent studies, the antioxidant and anticancer related properties of European hornbeam (Carpinus betulus L.) leaf extracts are remarkable, making it a possible raw material for medicine, requiring the identification of major active compounds and the assessment of the antioxidant properties of the extracts. In the present work the high-performance liquid chromatographic/multistage mass spectrometric characterization of the antioxidant polyphenolic compounds as well as the evaluation of the seasonal changes in the major antioxidant capacity and related parameters (DPPH, ABTS, FRAP, total phenol content, total flavonoid content and total flavan-3-ol content) have been carried out for the leaves of European hornbeam for the first time. The extracts exhibited the highest antioxidant capacity in August, basing on the FRAP (106.24 ± 3.10 mg AAE/g dw.) and DPPH (IC 50 : 4.63 ± 0.88 g/ml) assays and in May, based on the ABTS (329.78 ± 23.89 mg TE/g dw.) method. From the August extract a total of 171 compounds, including phenolic acids, flavonoid glycosides, tannins, catechins and procyanidins have been characterized and identified. According to the HPLC-PDA peak areas, the most abundant polyphenolic compounds in the August extracts were chlorogenic acid, ellagic acid, ellagitannins, myricetin-, luteolin-, quercetin-and apigenin glycosides. Further research is needed for the elucidation of the compounds which are primarily responsible for the antioxidant properties.

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Section: Total Flavan-3-ol Contentmentioning

confidence: 99%

Antioxidant properties and detailed polyphenol profiling of European hornbeam (Carpinus betulus L.) leaves by multiple antioxidant capacity assays and high-performance liquid chromatography/multistage electrospray mass spectrometry

Hofmann

Nebehaj

Albert

2016

Industrial Crops and Products

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“…However, when stained with dimethylaminocinnamaldehyde (DMACA) reagent, the TT2-expressing lines, but not the vector controls, turned an intense blue-green color ( Fig. 1 C and D), indicative of the presence of PA polymers, oligomers, or precursor flavan-3-ols (17) .…”

Section: Tt2mentioning

confidence: 99%

A transcript profiling approach reveals an epicatechin-specific glucosyltransferase expressed in the seed coat of Medicago truncatula

Pang

Peel

Sharma

et al. 2008

Proc. Natl. Acad. Sci. U.S.A.

177

208

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Expression of the Arabidopsis TRANSPARENT TESTA 2 (TT2) MYB family transcription factor leads to massive accumulation of proanthocyanidins (PAs) in hairy roots of Medicago truncatula. Microarray analysis showed that TT2 induces genes for flavonoid/PA biosynthesis, transcription factors, and a large number of genes of unknown function. A second microarray dataset identified genes that were preferentially expressed in the M. truncatula seed coat. Comparison of the two datasets defines target genes for steps that are yet unidentified in PA biosynthesis and accumulation. Of these genes, a glycosyltransferase, UGT72L1, was active specifically toward the PA precursor (؊)؊epicatechin, and its expression pattern in developing seeds correlated with the presence of epicatechin glucoside and accumulation of PAs. UGT72L1 may be involved in the production of epicatechin 3 -O-glucoside in the seed coat as a key step in PA biosynthesis or its regulation.glucosyltransferase ͉ model legume ͉ proanthocyanidin

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“…In contrast to PA, the synthesis of anthocyanin is more widespread in Arabidopsis, occurring in leaves, flowers, siliques, and four cell layers in maternal tissue of the developing seed (Devic et al, 1999). This indicates that although anthocyanin and PA may be synthesized from a common pathway, the PA-specific genes are regulated differently than the anthocyanin-specific genes.An alternative way of identifying Arabidopsis mutants specifically affected in the PA branch of the flavonoid pathway is to use the aromatic aldehyde reagent p-dimethylaminocinnamaldehyde (DMACA),which specifically reacts with PA polymers, small oligomers, and the immediate PA precursors, the flavan-3,4-diols and flavan-3-ols (McMurrough and McDowell, 1978;Delcour and Janssens de Varabeke, 1985;Garcia-Florenciano et al, 1989;Treutter, 1989). In this paper, we describe a simple screening method using DMACA stain on seed pools of Arabidopsis T-DNA-tagged lines to identify mutants of PA biosynthesis.…”

mentioning

confidence: 99%

“…An alternative way of identifying Arabidopsis mutants specifically affected in the PA branch of the flavonoid pathway is to use the aromatic aldehyde reagent p-dimethylaminocinnamaldehyde (DMACA),which specifically reacts with PA polymers, small oligomers, and the immediate PA precursors, the flavan-3,4-diols and flavan-3-ols (McMurrough and McDowell, 1978;Delcour and Janssens de Varabeke, 1985;Garcia-Florenciano et al, 1989;Treutter, 1989). In this paper, we describe a simple screening method using DMACA stain on seed pools of Arabidopsis T-DNA-tagged lines to identify mutants of PA biosynthesis.…”

mentioning

confidence: 99%

Identification and Biochemical Characterization of Mutants in the Proanthocyanidin Pathway in Arabidopsis

et al. 2002

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Proanthocyanidin (PA), or condensed tannin, is a polymeric flavanol that accumulates in a number of tissues in a wide variety of plants. In Arabidopsis, we found that PA precursors (detected histochemically using OsO 4 ) accumulate in the endothelial cell layer of the seed coat from the two-terminal cell stage of embryo development onwards. To understand how PA is made, we screened mature seed pools of T-DNA-tagged Arabidopsis lines to identify mutants defective in the synthesis of PA and found six tds (tannin-deficient seed) complementation groups defective in PA synthesis. Mutations in these loci disrupt the amount (tds1, tds2, tds3, tds5, and tds6) or location and amount of PA (tds4) in the endothelial cell layer. The PA intermediate epicatechin has been identified in wild type and mutants tds1, tds2, tds3, and tds5 (which do not produce PA) and tds6 (6% of wild-type PA), whereas tds4 (2% of wild-type PA) produces an unidentified dimethylaminocinnamaldehyde-reacting compound, indicating that the mutations may be acting on genes beyond leucoanthocyanidin reductase, the first enzymatic reduction step dedicated to PA synthesis. Two other mutants were identified, an allele of tt7, which has a spotted pattern of PA deposition and produces only 8% of the wild-type level of type PA as propelargonidin, and an allele of tt8 producing no PA. Spotted patterns of PA deposition observed in seed of mutants tds4 and tt7-3 result from altered PA composition and distribution in the cell. Our mutant screen, which was not exhaustive, suggests that the cooperation of many genes is required for successful PA accumulation.Flavonoids are a diverse group of plant secondary metabolites that accumulate in a wide variety of plant tissues and include anthocyanins, flavonols, and the polymeric flavanols known as proanthocyanidins (PAs; Fig. 1). Like their flavanol constituents, PAs are rich in hydrophobic aromatic rings and hydroxyl groups that can interact with biological molecules, particularly proteins, by hydrogen bonds and hydrophobic interactions. Because PAs are polymeric, their interaction with proteins is much stronger than that of monomeric flavanols, presumably because of a "chelate" effect where polymeric PAs can interact with large proteins at multiple sites, increasing the strength of overall molecular interaction as well as minimizing dissociation of the complex once it is formed (Fersht, 1985). This strong interaction of PAs with proteins is probably the basis of their main role in plants and their uses by man.Because PA content of dietary plants can have both positive and negative effects on animal nutrition (Waghorn and Jones, 1989), an important agricultural objective is to manipulate the level of PA in pasture legumes (Morris and Robbins, 1997). When present in bloat-safe forage legumes, PA can bind to and cause the precipitation of dietary proteins, inhibiting the formation of stable proteinaceous foams, thereby preventing bloat (Tanner et al., 1995). Increasing the PA content of pastures such as alfalfa (Medicago s...

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Chemical reaction detection of catechins and proanthocyanidins with 4-dimethylaminocinnamaldehyde

Cited by 174 publications

References 43 publications

Antioxidant properties and detailed polyphenol profiling of European hornbeam (Carpinus betulus L.) leaves by multiple antioxidant capacity assays and high-performance liquid chromatography/multistage electrospray mass spectrometry

Antioxidant properties and detailed polyphenol profiling of European hornbeam (Carpinus betulus L.) leaves by multiple antioxidant capacity assays and high-performance liquid chromatography/multistage electrospray mass spectrometry

A transcript profiling approach reveals an epicatechin-specific glucosyltransferase expressed in the seed coat of Medicago truncatula

Identification and Biochemical Characterization of Mutants in the Proanthocyanidin Pathway in Arabidopsis

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