Bo Zou

High molecular weight persimmon tannin ameliorates cognition deficits and attenuates oxidative damage in senescent mice induced by d-galactose

Mice were subcutaneously injected with d-galactose (D-gal, 150 mg/kg per day) for 6 weeks and were administered high molecular weight persimmon condensed tannin (HMWPT) simultaneously. After 6 weeks of treatment, the animal behavior was observed in the open field test and water maze test, and the morphology of hippocampus and skin were checked. Meanwhile, the activities of antioxidant enzymes, the levels of non-enzymatic antioxidants, as well as malondialdehyde (MDA) were evaluated. The results indicated that HMWPT markedly inhibited the d-gal induced learning and memory impairment in both open field test and Morris water maze. Biochemical examination revealed that HMWPT significantly increased the decreased activities of superoxide dismutase (SOD), catalase (CAT), elevated the lowered total anti-oxidation capability (T-AOC), glutathione (GSH) and hydroxyproline (Hyp) contents (p<0.01 or p<0.05), and decreased the raised monoamine oxidase (MAO), total cholinesterase (TChE) activities and MDA level (p<0.01) in serum, liver or brain of aging mice induced by d-gal in a dose-dependent fashion. Furthermore, HMWPT significantly and (p<0.01) attenuated the d-gal induced number decrease, neuronal degeneration and karyopycnosis in cells in the hippocampus and decrease of thickness of skin epidermis and dermis.

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.

Characterization of a highly polymeric proanthocyanidin fraction from persimmon pulp with strong Chinese cobra PLA2 inhibition effects.

Persimmon proanthocyanidin was fractionated on Toyopearl TSK-HW-50-F to yield a fraction with strong inhibition on the catalytic activity and edema-inducing activity and lethality of Chinese cobra PLA(2). Thiolysis suggested that the terminal units included C, EGCG and myricetin, and epicatechin, epigallocatechin, (epi)gallocatechin-3-O-gallate, and (epi)catechin-3-O-gallate occurred as extender units. The mean degree of polymerization was 23.7. MALDI TOF/MS, thioly-HPLC, FTIR and circular dichroism (CD) analyses showed that the fraction had high prodelphinidin content (55%) and a very high degree of 3-O-galloylation (92%). A type linkage is dominant in it and it had 4β linkage of the flavanyl substituent and 4R absolute configuration.

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.

The interaction of a polymeric persimmon proanthocyanidin fraction with Chinese cobra PLA2 and BSA

To elucidate the anti-venom mechanism of persimmon tannin, the interaction between a polymeric persimmon proanthocyanidin fraction (PT40) and phospholipase A2 (PLA2) or bovine serum albumin (BSA) were studied using a competitive binding assay and spectroscopic methods including Fourier transform infrared spectroscopy (FT-IR), circular dichroism (CD), and resonance light scattering (RLS) spectroscopy. The results revealed that PT40 has a higher affinity for PLA2 than for BSA at physiological pH and induced greater conformational changes in PLA2 than in BSA. PT40 covalently bound to PLA2 in a reaction probably involving Lys residues. We propose that the high affinity of PT40 for PLA2 and the covalent modification of PLA2 by PT40 may be responsible for the ability of the tannin to irreversibly inhibit PLA2 catalytic activity, to prevent edema, and to neutralize the lethality of Chinese cobra PLA2 in vivo.

A-type ECG and EGCG dimers disturb the structure of 3T3-L1 cell membrane and strongly inhibit its differentiation by targeting peroxisome proliferator-activated receptor γ with miR-27 involved mechanism

The effects of four proanthocyanidin dimers including epicatechin-(4β→8, 2β→O→7)-epicatechin (A-type EC dimer), epicatechin-(4β→8)-epicatechin (B-type EC dimer), epicatechin-3-gallate-(4β→8, 2β→O→7)-epicatechin-3-gallate (A-type ECG dimer) and epigallocatechin-3-gallate-(4β→8, 2β→O→7)-epigallocatechin-3-gallate (A-type EGCG dimer) on 3T3-L1 preadipocyte cell differentiation and the underlying mechanisms were explored and compared. The results showed that A-type ECG dimer and A-type EGCG dimer significantly reduced the intracellular lipid accumulation in 3T3-L1 preadipocyte cells by targeting miR-27a and miR-27b as well as peroxisome proliferator-activated receptor γ (PPARγ) in the early stage of differentiation, while A-type EC dimer and B-type EC dimer showed little effect. In addition, our results revealed that the inhibitory effects of proanthocyanidin dimers on 3T3-L1 preadipocyte differentiation were highly structure-dependent and the effects were associated with the dimer-membrane interactions. The presence of galloyl moieties and A-type linkage within the structure of proanthocyanidins might be crucial for their inhibitory effect on adipogenesis. The strong disturbing effects of A-type ECG and A type EGCG dimers on the fluidity, hydrophobicity and permeability of membrane of 3T3-L1 preadipocyte cell were at least, in part, responsible for their distinct inhibitory effects on adipocyte hyperplasia.

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.