Zhen-zhen Ge

Preparation of A-type proanthocyanidin dimers from peanut skins and persimmon pulp and comparison of the antioxidant activity of A-type and B-type dimers.

We have established a simple method for preparing large quantities of A-type dimers from peanut skin and persimmon for further structure-activity relationship study. Peanut skins were defatted with hexane and oligomeric proanthocyanidins were extracted from it with 20% of methanol, and the extract was fractionated with ethyl acetate. Persimmon tannin was extracted from persimmon with methanol acidified with 1% hydrochloric acid, after removing the sugar and small phenols, the high molecular weight persimmon tannin was partially cleaved with 6.25% hydrochloric acid in methanol. The ethyl acetate fraction from peanut skins and persimmon tannin cleaved products was chromatographed on AB-8 macroporous resin followed by Toyopearl HW-50F resin to yield about 378.3mg of A-type (epi)catechin (EC) dimer from 1 kg dry peanut skins and 34.3mg of A-type (epi)catechin-3-O-gallate (ECG) dimer and 37.7 mg of A-type (epi)gallocatechin-3-O-gallate (EGCG) dimer from 1 kg fresh persimmon fruit. The antioxidant properties of the A-type and B-type dimers were compared in five different assays, namely, 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical, 2,2-azino-bis (3-ethylbenzthiazoline-6-sulfonic acid) (ABTS) radical, hydroxyl radical, lipid peroxidation in mice liver homogenate and erythrocyte hemolysis in rat blood. Our results showed that both A-type and B-type dimers showed high antioxidant potency in a dose-dependent manner. In general, B-type dimers showed higher radical scavenging potency than A-type ones with the same subunits in aqueous systems. But in tissue or lipid systems, A-type dimers showed similar or even higher antioxidant potency than B-type ones.

Comparison of the Efficiency of Five Different Drying Carriers on the Spray Drying of Persimmon Pulp Powders

The aim of this work was to compare the efficiency of different carrier agents (maltodextrin, gum arabic, starch sodium octenyl succinate, whey protein concentrate, and egg albumin) on the powder recovery and physicochemical properties of persimmon powders produced by spray drying. Moisture content, water activity, hygroscopicity, solubility index, total phenol retention, color parameters, particle size, morphology, crystalline state, and sorption isotherms of persimmon powders were determined. No powder was recovered when the persimmon pulp was spray dried alone. The amount of maltodextrin, gum arabic, starch sodium octenyl succinate, whey protein concentrate, and egg albumin needed to obtain a powder recovery of 70% was 45, 30, 30, 25, and 10%, respectively. The use of maltodextrin, gum arabic, and starch sodium octenyl succinate resulted in higher total polyphenol retention and better reconstitution properties, but the powders were paler than those with whey protein concentrate and egg albumin. All carriers could aid the formation of persimmon irregular spherical microcapsules. However, powders produced with maltodextrin and gum arabic had a smoother surface and a more spherical shape than powders produced with other carriers. In addition, powders produced with starch sodium octenyl succinate, whey protein concentrate, and egg albumin were more agglomerated and shriveled compared to those produced with maltodextrin and gum arabic. All experimental data of water adsorption were well fitted to the Guggenheim-Anderson-de Boer (GAB) model.

Persimmon tannin represses 3T3-L1 preadipocyte differentiation via up-regulating expression of miR-27 and down-regulating expression of peroxisome proliferator-activated receptor-γ in the early phase of adipogenesis

AbstractPurpose Currently, obesity has become a worldwide health problem. Adipocyte differentiation is closely associated with the onset of obesity. Our previous studies suggested that persimmon tannin might be a potent anti-adipogenic dietary bioactive compound. However, the mechanism of persimmon tannin on adipocyte differentiation is still unknown. The purpose of this study was to investigate the effect of persimmon tannin on adipogenic differentiation in 3T3-L1 preadipocytes and the underlying mechanisms.MethodsAdipogenic differentiation was induced by cocktail in the presence or absence of persimmon tannin. Intracellular lipid accumulation was determined by Oil red O staining and enzymatic colorimetric methods. Gene expression and protein levels were measured by real time RT-PCR and Western blot.Results Persimmon tannin inhibited intracellular lipid accumulation markedly, and the inhibitory effect was largely limited to the early stage of adipocyte differentiation. Persimmon tannin suppressed the expression of C/EBPα and peroxisome proliferator-activated receptor-γ (PPARγ), significantly. Furthermore, genes related to lipogenesis, such as sterol regulatory element-binding protein 1, were down-regulated by persimmon tannin. In addition, adipocyte fatty acid binding protein (aP2), which is a target gene of PPARγ, was suppressed by persimmon tannin notably. Correspondingly, the expression of miR-27a and miR-27b were up-regulated by persimmon tannin from Day 2 to Day 8 significantly.ConclusionPersimmon tannin inhibited adipocyte differentiation through regulation of PPARγ, C/EBPα and miR-27 in early stage of adipogenesis.

Screening of key antioxidant compounds of longan (Dimocarpus longan Lour.) seed extract by combining online fishing/knockout, activity evaluation, Fourier transform ion cyclotron resonance mass spectrometry, and high-performance liquid chromatography electrospray ionization mass spectrometry methods.

To figure out the key phenolic compounds accounting for the antioxidant effects of longan (Dimocarpus longan Lour.) seed extract, online fishing/knockout method, activity evaluation assays, Fourier transform ion cyclotron resonance mass spectrometry (FT-ICR-MS), and high-performance liquid chromatography electrospray ionization mass spectrometry (HPLC-ESI-MS) analysis were used jointly for the first time. p-Coumaric acid-glycoside, (S)-flavogallonic acid, ellagic acid derivative, and methyl-ellagic acid glucopyranoside were first identified in longan seeds. In addition, our study revealed that ellagic acid as well as its derivative and p-coumaric acid-glycoside had important contribution to the potent antioxidant activity of longan seed extract, while gallic acid, corilagin, (S)-flavogallonic acid, methyl-ellagic acid glucopyranoside, and ethyl gallate showed very little contribution to the total antioxidant activity of longan seed extract. The combining use of the online fishing/knockout method, activity evaluation assays, FT-ICR-MS, and HPLC-ESI-MS analysis is a useful and simple strategy for screening of key bioactive compounds from complex extracts.

A-type dimeric epigallocatechin-3-gallate (EGCG) is a more potent inhibitor against the formation of insulin amyloid fibril than EGCG monomer.

Because fibrillary protein aggregates is regarded to be closely associated with many diseases such as Alzheimers disease, diabetes, and Parkinsons disease, growing interest and researches have been focused on finding potential fibrillation inhibitors. In the present study, the inhibitory effects of epigallocatechin-3-gallate (EGCG) and A-type dimeric epigallocatechin-3-gallate (A-type EGCG dimer) on the formation of insulin fibrillation were compared by multi-dimensional approaches including thioflavin-T (ThT) fluorescence assay, 1-anilinonaphthalene-8-sulfonic (ANS) fluorescence assay, dynamic light scattering (DLS), transmission electron microscopy (TEM), Fourier transform infrared (FTIR) spectroscopy and circular dichroism (CD) spectroscopy. Our results confirmed that A-type EGCG dimer is a more potent inhibitor against the formation of bovine insulin amyloid fibril than EGCG. In addition, A-type EGCG dimer could not only inhibit insulin amyloid fibril formation, but also change the aggregation pathway and induce bovine insulin into amorphous aggregates. The results of the present study may provide a new guide on finding novel anti-amyloidogenic agents.

Comparison of disaggregative effect of A-type EGCG dimer and EGCG monomer on the preformed bovine insulin amyloid fibrils

In the present study, the disruptive effects of epigallocatechin-3-gallate (EGCG) and A-type dimeric epigallocatechin-3-gallate (A-type EGCG dimer) on the preformed bovine insulin amyloid fibrils were studied by several biophysical methods including thioflavin-T (ThT) fluorescence assay, 1-anilinonaphthalene-8-sulfonic (ANS) fluorescence assay, Congo red (CR) binding assay, dynamic light scattering (DLS), transmission electron microscopy (TEM), Gel electrophoresis (SDS-PAGE) and Bradford assay. Our results demonstrated that A-type EGCG dimer showed significantly more potential disaggregative effects on the bovine insulin amyloid fibrils than EGCG. A-type EGCG dimer could not only dramatically promote the disaggregation of the preformed bovine insulin amyloid fibrils, but also restructure the amyloid fibrils into amorphous aggregates. While, EGCG could only shorten and thin the fibrils, but induce no small amorphous aggregates. Our present results provided additional evidence for the more potent disaggregation effects of dimeric polyphenols than monomeric polyphenols and suggested that A-type EGCG dimer seems to have potential application as an excellent anti-amyloidogenic agent.

Erratum to: Development of suitable standards for quantitative determination of persimmon phenol contents in Folin-Ciocalteu and vanillin assays

Use of gallic acid (GA) as a standard in the Folin-Ciocalteu assay leads to an underestimation of phenol content in persimmon extracts so does the widely used catechin (C) in vanillin assay for determining condensed tannins in persimmon extracts. To develop suitable standards for addressing the issue of accuracy, we prepared highly purified persimmon tannin (PT) and its three fractions (PT20, PT40 and PT60), as well as three characteristic structural subunits of PT including epicatechin-3-gallate-(4β → 8, 2β → O→7)-epicatechin-3-gallate (A-type ECG dimer), epigallocatechin-3-gallate-(4β → 8, 2β → O→7)-epigallocatechin-3-gallate (A-type EGCG dimer) and epicatechin-(4β → 8)-epicatechin (B-type EC dimer). We compared the color yield of commercially available standards including the dimers GA, EGCG, ECG, C and PT and its three fractions in the Folin-Ciocalteu assay and vanillin assay, respectively. Our results suggested that for estimating phenol content in persimmon extracts, EGCG, ECG, C and GA were poor standards in Folin-Ciocalteu assay. We recommended PT40 as the most suitable standard in determining the phenol content of persimmon extracts. In the vanillin assay, A-type EGCG dimer or A-type ECG dimer were superior than the commonly used C as standards, and ECG was also an alternative when A-type EGCG dimer or A-type ECG dimer were not available.

Interactions between highly galloylated persimmon tannins and pectins

The interactions between pectins of different degrees of esterification (DE) and highly galloylated persimmon tannins with average degrees of polymerisation (DP26 and DP5) were investigated by UV-Vis spectrophotometry, dynamic light scattering, transmission electron microscopy, isothermal titration calorimetry and pyrene fluorescence methods Pectins displayed strong effects on the self-aggregation of persimmon tannins and improved the homogeneity of condensed tannin aggregates. The interaction between tannins and pectins may result from hydrogen bonding and hydrophobic interactions; by contrast, electrostatic interactions, which involve charged molecules in general, played no dominant role. In addition, the presence of gallate moieties in the high-polymerisation proanthocyanidin could enhance affinity with highly methylated pectins. Stronger association was observed with the high-polymerisation tannins (DP26) with high-methoxyl pectin (DE74) (Ka=(8.50±3.0)×103M-1) than with low-methylated pectin (DE30) (Ka=(3.62±1.92)×103M-1). The present results are expected to promote the application of the formed complexes as functional ingredients in food.

Understanding the shielding effects of whey protein on mulberry anthocyanins: Insights from multispectral and molecular modelling investigations

Assembling between polyphenols and proteins has been recently spotlighted and this binding is of specific importance in food chemistry since these complexes are typically used in different foodstuffs. A study on the copigmentation among three encapsulation wall-materials, including maltodextrin, gum Arabic, and whey proteins, with mulberry anthocyanins (AC) proved that whey protein (WP) is an outstanding wall-material due to its wrapping and hyperchromicity effects. Additionally, high binding ability of WP with AC was shown to be responsible for its superior copigmentation effects. Accordingly, the underlying shielding mechanism of WP on AC based on their non-covalent assembling was deeply studied using multispectral and computational assays. The fluorometric results demonstrated that a static and heat-stable binding between WP and AC occurred, leading to modification in size, hydrophobicity, and secondary structures of WP. The docking results explained that WP-AC complex was mainly molded via hydrophobic effects of WP surface and subsequently be stabilized by H-bonding and van der Waals forces. These results may contribute to a better understanding on the enhanced colouring proprieties of anthocyanins by using whey proteins.