Vitisin A

Percutaneous absorption of resveratrol and its oligomers to relieve psoriasiform lesions: In silico, in vitro and in vivo evaluations.[Pubmed:32512223]

Int J Pharm. 2020 Jul 30;585:119507.

Resveratrol was shown to exert anti-inflammatory effects in experimental models of psoriasis. Several natural oligomers of resveratrol have been extracted from plants. We investigated the antipsoriatic activity of topical administration of resveratrol oligomers and explored the effect of the number of resveratrol subunits on skin absorption to establish the structure-permeation relationship (SPR). Three oligomers, epsilon-viniferin (dimer), ampelopsin C (trimer) and Vitisin A (tetramer), extracted from Vitis thunbergii root were compared to the resveratrol glycoside polydatin. Delivery to porcine skin was assessed in vitro using the Franz cell. Keratinocytes activated with imiquimod (IMQ) were utilized to evaluate cytokine/chemokine inhibition. Topical application of resveratrol and oligomers was characterized in vivo by assessing cutaneous absorption, skin physiology, proinflammatory mediator expression, and histopathology in IMQ-treated mice. Skin deposition decreased as the molecular size and lipophilicity of the permeants increased. Resveratrol exhibited highest absorption, followed by epsilon-viniferin. The monomers resveratrol and polydatin exhibited higher flux across skin than the larger oligomers. In silico modeling revealed the permeants that strongly interacted with stratum corneum (SC) lipids exhibited lower transport to viable skin and the receptor compartment. In vitro, resveratrol and its derivatives had comparable ability to inhibit IMQ-induced IL-1beta, IL-6, and CXCL8 secretion in activated keratinocytes. In vivo, topically applied epsilon-viniferin accumulated at higher levels than resveratrol (0.067 versus 0.029 nmol/mg) in psoriasis-like mouse skin with impaired barrier capacity. Topical epsilon-viniferin alleviated psoriasiform symptoms and reduced IL-23 secretion (by 58% vs. 37%) more effectively than resveratrol. epsilon-Viniferin has potential as an anti-inflammatory agent to prevent or treat psoriasis.

Influence of sequential inoculum of Starmerella bacillaris and Saccharomyces cerevisiae on flavonoid composition of monovarietal Sangiovese wines.[Pubmed:32410256]

Yeast. 2020 May 14.

The selection of Starmerella bacillaris strains to be used with Saccharomyces cerevisiae as mixed cultures has been recently suggested in order to produce wines containing lower ethanol and higher glycerol concentrations and to promote fructose degradation due to their fructophilic character. However, studies about effects of such mixed starter cultures on phenolic compounds, which are responsible for the colour and health-enhancing properties in red wines, are currently lacking. Therefore, in this work, the influence of sequential inoculated fermentation (SIF) with Starm. bacillaris and S. cerevisiae on phenolic content of monovarietal Sangiovese wine was evaluated by fermentations at laboratory scale. Axenic fermentations (AXFs) with S. cerevisiae were performed as control. S. cerevisiae attained higher cell densities in AXF compared with SIF. The experimental wines obtained by SIF showed significant lower ethanol and higher glycerol concentrations, whereas no significant difference was detected in colour intensity. The total phenol index reached significantly lower values in SIF. Furthermore, the wines produced by SIF contained higher concentrations of Vitisin A that has a greater colour stability than the anthocyanin monomer. Finally, a lower content of both free anthocyanins and flavan-3-ols, key compounds for wine quality possessing also health-enhancing properties, was found in wines obtained by SIF. On the contrary, no significant difference was detected on flavonol concentration between SIF and AXF. This study highlighted that the use of sequential inoculum of Starm. bacillaris and S. cerevisiae can contribute to increasing the colour stability of red wines, even if at the expense of compounds with health properties.

Pulsed Electric Field Processing of Red Grapes (cv. Rondinella): Modifications of Phenolic Fraction and Effects on Wine Evolution.[Pubmed:32252247]

Foods. 2020 Apr 2;9(4). pii: foods9040414.

Pulsed electric field (PEF) is a non-thermal technology able to promote color and polyphenols extraction from grape skins. Most of the publications about PEF in winemaking report data concerning international varieties, poorly considering minor cultivars and the medium/long-term effects of the treatment on wine composition during storage. PEF was applied at different specific energies (2, 10, and 20 kJ kg(-1)) on grapes of the low-color red cv. Rondinella, after crushing-destemming. Pressing yield, the evolution of color, and total phenolic index (TPI) were measured during skin maceration. Moreover, the wines were characterized for basic compositional parameters, color, anthocyanin profile, phenolic composition (glories indices), metal content (Fe, Cr, and Ni), and sensory characters, two and twelve months after the processing, in comparison with untreated samples and pectolytic enzymes (PE). PEF did not affect fermentation evolution, nor did it modify wine basic composition or metal content. Treatments at 10 and 20 kJ kg(-1) led to higher color and TPI in wines, in comparison to PE, because of increased content of anthocyanins and tannins. The sensory evaluation confirmed these findings. Modifications remained stable in wines after twelve months. Glories indices and Vitisin A content highlighted greater potential stability of wine color in PEF-treated wines.

Synthesis of Vitisins A and D Enabled by a Persistent Radical Equilibrium.[Pubmed:32156107]

J Am Chem Soc. 2020 Apr 8;142(14):6499-6504.

The first total synthesis of the resveratrol tetramers Vitisin A and vitisin D is reported. Electrochemical generation and selective dimerization of persistent radicals is followed by thermal isomerization of the symmetric C8b-C8c dimer to the C3c-C8b isomer, providing rapid entry into the vitisin core. Computational results suggest that this synthetic approach mimics Nature's strategy for constructing these complex molecules. Sequential acid-mediated rearrangements consistent with the proposed biogenesis of these compounds afford Vitisin A and vitisin D. The rapid synthesis of these complex molecules will enable further study of their pharmacological potential.

Influence of Saccharomyces and non-Saccharomyces Yeasts in the Formation of Pyranoanthocyanins and Polymeric Pigments during Red Wine Making.[Pubmed:31817948]

Molecules. 2019 Dec 8;24(24). pii: molecules24244490.

Yeast are able to modulate many sensory parameters of wines during red must fermentation. The effect on color and on the formation of derived pigments during fermentation has been studied thoroughly since the 90s. Yeast can increase grape anthocyanin's color by acidification by hyperchromic effect (increase of flavylium molecules). Recent studies with non-Saccharomyces species, as Lachancea thermotolerans, described the intense effect of some strains on anthocyanin's color, and subsequent, stability, by strongly reducing wine's pH during fermentation. Moreover, selected yeast strains of Saccharomyces have been shown to release metabolites such as pyruvic acid or acetaldehyde that promote the formation of Vitisin A and B pyranoanthocyanins during must fermentation. Schizosaccharomyces pombe, because of its specific metabolism, can produce higher concentrations of pyruvate, which enhances the formation of Vitisin A-type derivatives. The hydroxycinnamate decarboxylase activity that some Saccharomyces strains express during fermentation also promotes the formation of vinylphenolic derivatives. Some non-Saccharomyces species, such as S. pombe or P. guilliermondii can also improve the production of these derivatives compared to selected strains of Saccharomyces cerevisiae. Lastly, some yeasts are also able to modulate the formations of polymeric pigments between grape anthocyanins and flavonoids, such as catechins and procyanidins.

The anti-biofilm and anti-virulence activities of trans-resveratrol and oxyresveratrol against uropathogenic Escherichia coli.[Pubmed:31505984]

Biofouling. 2019 Aug;35(7):758-767.

Uropathogenic Escherichia coli (UPEC) is the primary causative agent of urinary tract infections, which are one of the most common infectious disease types in humans. UPEC infections involve bacterial cell adhesion to bladder epithelial cells, and UPEC can also form biofilms on indwelling catheters that are often tolerant to common antibiotics. In this study, the anti-biofilm activities of t-stilbene, stilbestrol, t-resveratrol, oxyresveratrol, epsilon-viniferin, suffruticosol A, and Vitisin A were investigated against UPEC. t-Resveratrol, oxyresveratrol, and epsilon-viniferin, suffruticosol A, and Vitisin A significantly inhibited UPEC biofilm formation at subinhibitory concentrations (10-50 mug ml(-1)). These findings were supported by observations that t-resveratrol and oxyresveratrol reduced fimbriae production and the swarming motility in UPEC. Furthermore, t-resveratrol and oxyresveratrol markedly diminished the hemagglutinating ability of UPEC, and enhanced UPEC killing by human whole blood. The findings show that t-resveratrol, oxyresveratrol, and resveratrol oligomers warrant further attention as antivirulence strategies against persistent UPEC infections.

Pyranoanthocyanins in bilberry (Vaccinium myrtillus L.) wines fermented with Schizosaccharomyces pombe and their evolution during aging.[Pubmed:31494498]

Food Chem. 2020 Feb 1;305:125438.

Fifteen Vitisin A-type pyranoanthocyanins (vAPs) were determined in bilberry wines fermented with Saccharomyces cerevisiae and Schizosaccharomyces pombe by HPLC-DAD and UPLC-DAD-ESI-MS/MS. The fermentation involving S. pombe enhanced the production of vAPs compared to the fermentation with pure S. cerevisiae. The formation of vAPs correlated significantly with the decrease in the content of monomeric anthocyanins and pyruvic acid during 12months of aging. vAPs were more stable than their corresponding monomeric anthocyanins. Methylation in the B-ring and glycosylation with galactose and arabinose further improved the stability of vAPs. Aging for 12months led to depletion of pyruvic acid and reduction of over 50% of monomeric anthocyanins. The content of vAPs increased by 26-54% during the first six months of aging, followed by a 2.2-10.2% reduction over the following six months. More residual pyruvic acid in S. pombe wines after fermentation consequently enhanced the generation of vAPs during aging.

Antibacterial Activities of Metabolites from Vitis rotundifolia (Muscadine) Roots against Fish Pathogenic Bacteria.[Pubmed:30366372]

Molecules. 2018 Oct 25;23(11). pii: molecules23112761.

Enteric septicemia of catfish, columnaris disease and streptococcosis, caused by Edwardsiella ictaluri, Flavobacterium columnare and Streptococcus iniae, respectively, are the most common bacterial diseases of economic significance to the pond-raised channel catfish Ictalurus punctatus industry. Certain management practices are used by catfish farmers to prevent large financial losses from these diseases such as the use of commercial antibiotics. In order to discover environmentally benign alternatives, using a rapid bioassay, we evaluated a crude extract from the roots of muscadine Vitis rotundifolia against these fish pathogenic bacteria and determined that the extract was most active against F. columnare. Subsequently, several isolated compounds from the root extract were isolated. Among these isolated compounds, (+)-hopeaphenol (2) and (+)-Vitisin A (3) were found to be the most active (bacteriostatic activity only) against F. columnare, with 24-h 50% inhibition concentrations of 4.0 +/- 0.7 and 7.7 +/- 0.6 mg/L, respectively, and minimum inhibitory concentrations of 9.1 +/- 0 mg/L for each compound which were approximately 25X less active than the drug control florfenicol. Efficacy testing of 2 and 3 is necessary to further evaluate the potential for these compounds to be used as antibacterial agents for managing columnaris disease.

Effects of the oligostilbenes from Iris lactea Pall. var. chinensis (Fisch.) Koidz on the adipocytes differentiation of 3T3-L1 cells.[Pubmed:29442012]

Pharmazie. 2018 Feb 1;73(2):98-103.

The dried seeds of Iris lactea Pall. var. chinensis (Fisch.) Koidz, an important traditional Chinese medicine, are regarded to have effects of clearing heat, eliminating dampness and pharyngitis and so on. It has been used in the treatment of jaundice, diarrhea, leucorrhea and carbuncles. Previous phytochemical studies of Iris species showed the presence of flavones, isoflavones, triterpenes and stilbenes. In our previous research, we isolated five known oligostilbenes, Vitisin A, vitisin B, vitisin C, vitisin D, and cis-Vitisin A were successfully isolated from Iris lactea for the first time. The aim of this study was to assess the effects of these oligostilbenes on the differentiation and adipogenes in 3T3-L1 cells. Our results showed that Vitisin A, vitisin B, cis-Vitisin A significantly inhibited adipocytes differentiation and reduced lipid accumulation in 3T3-L1 cells. In addition, Vitisin A, vitisin B, cis-Vitisin A strongly suppressed the expression levels of adipocyte-specific genes including peroxisome proliferator activated receptor-gamma (PPARgamma), CCAAT/enhancer binding protein-alpha (C/EBPalpha) and adipocyte fatty acid binding protein 4 (FABP4). In contrast, vitisin C and vitisin D significantly promoted adipogenesis and increased intracellular lipid accumulation, while the two oligostilbenes markedly increased the expression of adipocyte marker genes. In the present study, we found that Vitisin A, vitisin B and cis-Vitisin A inhibit the adipogenesis and adipocytes differentiation by their influence on the expression of PPARgamma, which leads to subsequenet downregulation of PPARgamma mediated adipocyte-specific gene during adipogenesis.

Anti-Inflammatory Effects of Vitisinol A and Four Other Oligostilbenes from Ampelopsis brevipedunculata var. Hancei.[Pubmed:28714918]

Molecules. 2017 Jul 17;22(7). pii: molecules22071195.

In this study, the cytotoxicities and anti-inflammatory activities of five resveratrol derivatives-vitisinol A, (+)-epsilon-viniferin, (+)-Vitisin A, (-)-vitisin B, and (+)-hopeaphenol-isolated from Ampelopsis brevipedunculata var. hancei were evaluated by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) assay and lipopolysaccharide (LPS)-stimulated RAW264.7 cells, respectively. The result from MTT assay analysis indicated that vitisinol A has lower cytotoxicity than the other four well-known oligostilbenes. In the presence of vitisinol A (5 muM), the significant reduction of inflammation product (nitric oxide, NO) in LPS-induced RAW264.7 cells was measured using Griess reaction assay. In addition, the under-expressed inflammation factors cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) in LPS-induced RAW264.7 cells monitored by Western blotting simultaneously suggested that vitisinol A has higher anti-inflammatory effect compared with other resveratrol derivatives. Finally, the anti-inflammatory effect of vitisinol A was further demonstrated on 12-O-tetradecanoylphorbol 13-acetate (TPA)-induced ear edema in mice. As a preliminary functional evaluation of natural product, the anti-inflammatory effect of vitisinol A is the first to be examined and reported by this study.

The Effects of Pre-Fermentative Addition of Oenological Tannins on Wine Components and Sensorial Qualities of Red Wine.[Pubmed:27809234]

Molecules. 2016 Oct 31;21(11). pii: molecules21111445.

Today in the wine industry, oenological tannins are widely used to improve wine quality and prevent oxidation in wine aging. With the development of tannin products, new oenological tannins are developed with many specific functions, such as modifying antioxidant effect, colour stabilization and aroma modifications. The aim of this work is to investigate effects of pre-fermentative addition of oenological tannins on wine colour, anthocyanins, volatile compounds and sensorial properties. In this case, Syrah juice was extracted with classic flash thermovinification from fresh must in order to release more colour and tannins. Three types of oenological tannins, which are, respectively, derived from grape skin, seed (Vitis vinifera) and French oak (Quercus robur and Querrus petraea), were selected to carry out the experiments with seven treatments. Results indicated that tannin treatments significantly improved wine aroma complexity and sensorial properties. However, the concentration of some stable pigments such as Vitisin A, Vitisin A-Ac and Vitisin B was negatively affected by tannin additions. Nevertheless, by means of cluster analysis and principal component analysis, it was observed that higher alcohols were significantly promoted by grape seed tannin while most anthocyanins can be improved by addition of grape tannins. In conclusion, low amount of oenological tannin derived from grape seed is a promising method to be applied especially for young red wine making.