A trimer plus a dimer-gallate reproduce the bioactivity described for an extract of grape seed procyanidins

Montagut, Gemma; Baiges, Isabel; Valls, Josep; Terra, Ximena; Bas, Josep Maria del; Vitrac, Xavier; Richard, Tristan; Mérillon, Jean‐Michel; Arola, Lluı́s; Blay, Mayte; Bladé, Cinta; Fernández-Larrea, Juan; Pujadas, Gerard; Salvadó, Josepa; Ardévol, Anna

doi:10.1016/j.foodchem.2009.02.044

Cited by 29 publications

(24 citation statements)

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“…Besides the flavan-3-ol monomers (−)-epicatechin and (+)-catechin constituting 17.4% and 9.8%, respectively, procyanidin dimers accounted for 13.1% and procyanidin trimer T2 [(−)-epicatechin-(4β→8)-(−)-epicatechin-(4β→8)-(+)-catechin] for 1.4%. These oligomers are important compounds because of their bioactivity as anti-inflammatory agents [20]. …”

Section: Resultsmentioning

confidence: 99%

Proanthocyanidin Characterization, Antioxidant and Cytotoxic Activities of Three Plants Commonly Used in Traditional Medicine in Costa Rica: Petiveria alliaceae L., Phyllanthus niruri L. and Senna reticulata Willd.

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Arnáez

et al. 2017

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The phenolic composition of aerial parts from Petiveria alliaceae L., Phyllanthus niruri L. and Senna reticulata Willd., species commonly used in Costa Rica as traditional medicines, was studied using UPLC-ESI-TQ-MS on enriched-phenolic extracts. Comparatively, higher values of total phenolic content (TPC), as measured by the Folin-Ciocalteau method, were observed for P. niruri extracts (328.8 gallic acid equivalents/g) than for S. reticulata (79.30 gallic acid equivalents/g) whereas P. alliaceae extract showed the lowest value (13.45 gallic acid equivalents/g). A total of 20 phenolic acids and proanthocyanidins were identified in the extracts, including hydroxybenzoic acids (benzoic, 4-hydroxybenzoic, gallic, prochatechuic, salicylic, syringic and vanillic acids); hydroxycinnamic acids (caffeic, ferulic, and p-coumaric acids); and flavan-3-ols monomers [(+)-catechin and (−)-epicatechin)]. Regarding proanthocyanidin oligomers, five procyanidin dimers (B1, B2, B3, B4, and B5) and one trimer (T2) are reported for the first time in P. niruri, as well as two propelargonidin dimers in S. reticulata. Additionally, P. niruri showed the highest antioxidant DPPH and ORAC values (IC50 of 6.4 μg/mL and 6.5 mmol TE/g respectively), followed by S. reticulata (IC50 of 72.9 μg/mL and 2.68 mmol TE/g respectively) and P. alliaceae extract (IC50 >1000 μg/mL and 1.32 mmol TE/g respectively). Finally, cytotoxicity and selectivity on gastric AGS and colon SW20 adenocarcinoma cell lines were evaluated and the best values were also found for P. niruri (SI = 2.8), followed by S. reticulata (SI = 2.5). Therefore, these results suggest that extracts containing higher proanthocyanidin content also show higher bioactivities. Significant positive correlation was found between TPC and ORAC (R2 = 0.996) as well as between phenolic content as measured by UPLC-DAD and ORAC (R2 = 0.990). These findings show evidence for the first time of the diversity of phenolic acids in P. alliaceae and S. reticulata, and the presence of proanthocyanidins as minor components in latter species. Of particular relevance is the occurrence of proanthocyanidin oligomers in phenolic extracts from P. niruri and their potential bioactivity.

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Section: Resultsmentioning

confidence: 99%

Proanthocyanidin Characterization, Antioxidant and Cytotoxic Activities of Three Plants Commonly Used in Traditional Medicine in Costa Rica: Petiveria alliaceae L., Phyllanthus niruri L. and Senna reticulata Willd.

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“…47,54 However, the increased serum concentrations of TC and LDL-C, and the decreased level of HDL-C, were found to be greatly ameliorated upon pretreatment with the proanthocyanidin-rich DTX. Studies with animal models reported that proanthocyanidins significantly decrease plasma concentration of TG (in hypotriglyceridemia), TC, and LDL-C along with an increase in HDL-C. 55 Moreover, Montagut et al 56 concluded that proanthocyanidins may be largely responsible for inhibiting TG and Apolipoprotein B secretion (a marker of VLDL) by hepatic cells. It also was found that proanthocyanidins repress the expression of 3-hydroxy-3-methyl-glutaryl-CoA (HMG-CoA) reductase, HMG-CoA synthetase, and other enzymes involved in cholesterol biosynthesis.…”

Section: Discussionmentioning

confidence: 99%

Proanthocyanidin-Rich Date Seed Extract Protects Against Chemically Induced Hepatorenal Toxicity

Ahmed

Alqahtani²,

Al‐Yousef³

et al. 2015

Journal of Medicinal Food

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A hydroacetone extract was prepared from seeds of Phoenix dactylifera L. var. Khalas, which is an industrial by-product of date processing. The proanthocyanidin nature of the extract (coded as DTX) was characterized by phytochemical and nuclear magnetic resonance (NMR) analyses. The total phenol/proanthocyanidin content and antioxidant activity of DTX were estimated by Folin-Ciocalteu, vanillin-sulfuric acid, and 2,2-diphenyl-1-picrylhydrazyl (DPPH) assays, respectively. The hepatorenal protective activity of DTX was evaluated using CCl4-induced toxicity model in rats, in comparison with silymarin (SYL). Results of the histopathological examination and measurements of various hepatorenal serum indices and tissue biochemical markers demonstrated that DTX displayed marked protective potential against CCl4-induced liver and kidney injury at 100 mg/kg/rat. Relative to the control CCl4-intoxicated group, pretreatment with DTX significantly (P<.001) suppressed the elevated serum levels of alanine aminotransferase and aspartate aminotransferase (ALT and AST), alkaline phosphatase (ALP), γ-glutamyl transferase (GGT), total cholesterol (TC), low-density lipoprotein cholesterol (LDL-C), bilirubin, creatinine, and calcium, whereas it significantly (P<.001) increased the diminished serum levels of high-density lipoprotein cholesterol (HDL-C) and total protein (TP). Moreover, DTX significantly decreased malondialdehyde (MDA) formation and increased TP synthesis in hepatorenal tissues compared with the intoxicated control. The improvement in biochemical parameters by DTX was observed in a dose-dependent manner and confirmed by restoration of normal histological features. The acute toxicity test of DTX in rats revealed safety of the extract. This study reveals that DTX enhances the recovery from xenobiotics-induced toxicity initiated by free radicals.

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“…We have also shown that GSPE decreases postprandial plasma TG and apolipoprotein B in mice through a hepatic induction of a farnesoid X receptor (FXR) and the small heterodimer partner (SHP) that in turn down-regulates SREBP1c and other lipogenic genes in the liver (21,22). Furthermore, we have demonstrated that the molecules responsible for the reduced TG synthesis in HepG2 cells treated with GSPE are the sum of a proanthocyanidins trimer and a dimer gallate because they reproduce the GSPE effect (23).…”

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Lipogenesis Is Decreased by Grape Seed Proanthocyanidins According to Liver Proteomics of Rats Fed a High Fat Diet

Baiges

Palmfeldt

Bladé

et al. 2010

Molecular & Cellular Proteomics

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Bioactive proanthocyanidins have been reported to have several beneficial effects on health in relation to metabolic syndrome, type 2 diabetes, and cardiovascular disease. We studied the effect of grape seed proanthocyanidin extract (GSPE) in rats fed a high fat diet (HFD). This is the first study of the effects of flavonoids on the liver proteome of rats suffering from metabolic syndrome. Three groups of rats were fed over a period of 13 weeks either a chow diet (control), an HFD, or a high fat diet supplemented for the last 10 days with GSPE (HFD ؉ GSPE). The liver proteome was fractionated, using a Triton X-114-based two-phase separation, into soluble and membrane protein fractions so that total proteome coverage was considerably improved. The data from isobaric tag for relative and absolute quantitation (

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A trimer plus a dimer-gallate reproduce the bioactivity described for an extract of grape seed procyanidins

Cited by 29 publications

References 28 publications

Proanthocyanidin Characterization, Antioxidant and Cytotoxic Activities of Three Plants Commonly Used in Traditional Medicine in Costa Rica: Petiveria alliaceae L., Phyllanthus niruri L. and Senna reticulata Willd.

Proanthocyanidin Characterization, Antioxidant and Cytotoxic Activities of Three Plants Commonly Used in Traditional Medicine in Costa Rica: Petiveria alliaceae L., Phyllanthus niruri L. and Senna reticulata Willd.

Proanthocyanidin-Rich Date Seed Extract Protects Against Chemically Induced Hepatorenal Toxicity

Lipogenesis Is Decreased by Grape Seed Proanthocyanidins According to Liver Proteomics of Rats Fed a High Fat Diet

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