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Concept: Tannin

171

Monomeric anthocyanins and polymeric proanthocyanidins (condensed tannins) contribute to important plant traits such as flower and fruit pigmentation, fruit astringency, disease resistance and forage quality. Recent advances in our understanding of the transcriptional control mechanisms that regulate anthocyanin and condensed tannin formation in plants suggest new approaches for the engineering of quality traits associated with these molecules. In particular, MYB family transcription factors are emerging as central players in the coordinated activation of sets of genes specific for the anthocyanin and tannin pathways. Mutations in these genes underlie potentially valuable crop traits, and ectopic over- or under-expression of MYB transcription factors provides routes for engineering of these complex pathways.

Concepts: DNA, Protein, Genetics, Gene expression, Transcription, Plant, RNA polymerase, Tannin

169

BACKGROUND: This study evaluated, using in vitro assays, the antibacterial, antioxidant, and tyrosinase-inhibition activities of methanolic extracts from peels of seven commercially grown pomegranate cultivars. METHODS: Antibacterial activity was tested on Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli and Klebsiella pneumonia) using a microdilution method. Several potential antioxidant activities, including radical-scavenging ability (RSA), ferrous ion chelating (FIC) and ferric ion reducing antioxidant power (FRAP), were evaluated. Tyrosinase enzyme inhibition was investigated against monophenolase (tyrosine) and diphenolase (DOPA), with arbutin and kojic acid as positive controls. Furthermore, phenolic contents including total flavonoid content (TFC), gallotannin content (GTC) and total anthocyanin content (TAC) were determined using colourimetric methods. HPLC-ESI/MSn analysis of phenolic composition of methanolic extracts was also performed. RESULTS: Methanolic peel extracts showed strong broad-spectrum activity against Gram-positive and Gram-negative bacteria, with the minimum inhibitory concentrations (MIC) ranging from 0.2 to 0.78 mg/ml. At the highest concentration tested (1000 mug/ml), radical scavenging activities were significantly higher in Arakta (83.54%), Ganesh (83.56%), and Ruby (83.34%) cultivars (P< 0.05). Dose dependent FIC and FRAP activities were exhibited by all the peel extracts. All extracts also exhibited high inhibition (>50%) against monophenolase and diphenolase activities at the highest screening concentration. The most active peel extract was the Bhagwa cultivar against monophenolase and the Arakta cultivar against diphenolase with IC50 values of 3.66 mug/ml and 15.88 mug/ml, respectively. High amounts of phenolic compounds were found in peel extracts with the highest and lowest total phenolic contents of 295.5 (Ganesh) and 179.3 mg/g dry extract (Molla de Elche), respectively. Catechin, epicatechin, ellagic acid and gallic acid were found in all cultivars, of which ellagic acid was the most abundant comprising of more than 50% of total phenolic compounds detected in each cultivar. CONCLUSIONS: The present study showed that the tested pomegranate peels exhibited strong antibacterial, antioxidant and tyrosinase-inhibition activities. These results suggest that pomegranate fruit peel could be exploited as a potential source of natural antimicrobial and antioxidant agents as well as tyrosinase inhibitors.

Concepts: Bacteria, Microbiology, Escherichia coli, Fruit, Tannin, Gram-negative bacteria, Pomegranate, Ferric

168

Catechins (flavan-3-ols), the most important secondary metabolites in the tea plant, have positive effects on human health and are crucial in defense against pathogens of the tea plant. The aim of this study was to elucidate the biosynthetic pathway of galloylated catechins in the tea plant. The results suggested that galloylated catechins were biosynthesized via 1-O-glucose ester-dependent two-step reactions by acyltransferases, which involved two enzymes, UDP-glucose: galloyl-1-O-β-D-glucosyltransferase (UGGT) and a newly discovered enzyme, epicatechin:1-O-galloyl-β-D-glucose O-galloyltransferase (ECGT). In the first reaction, the galloylated acyl donor β-glucogallin was biosynthesized by UGGT from gallic acid and uridine diphosphate glucose. In the second reaction, galloylated catechins were produced by ECGT catalysis from β-glucogallin and 2,3-cis-flavan-3-ol. 2,3-cis-flavan-3-ol and 1-O-galloyl-β-D-glucose were appropriate substrates of ECGT rather than 2,3-trans-flavan-3-ol and 1,2,3,4,6- pentagalloylglucose. Purification by more than 1641-fold to apparent homogeneity yielded ECGT with an estimated molecular mass of 241 to 121 kDa by gel filtration. Enzyme activity and SDS-PAGE analysis indicated that the native ECGT might be a dimer, trimer or tetramer of 60 and/or 58 kDa monomers, and these monomers represent a heterodimer consisting of pairs of 36- or 34-, and 28-kDa subunits. MALDI-TOF-TOF MS showed that the protein SCPL1199 was identified. Epigallocatechin and epicatechin exhibited higher substrate affinities than β-glucogallin. ECGT had an optimum temperature of 30 and maximal reaction rates between pH 4.0 and 6.0. The enzyme reaction was inhibited dramatically by phenylmethylsulfonyl fluoride, HgCl2, and sodium deoxycholate.

Concepts: Molecular biology, Metabolism, Enzyme, Catechin, Camellia sinensis, Green tea, Tannin, White tea

149

Considering the indigenous utilization of Quercus incana Roxb., the present study deals with the investigation of antioxidant, free radical scavenging activity, total phenolic content, and antimicrobial activity of Q. incana Roxb. In vitro antioxidant activity of the plant fractions were determined by 1,1-diphenyl-2-picrylhydrazyl and nitric oxide scavenging method. Total phenolic contents were determined by gallic acid equivalent and antimicrobial activities were determined by agar well diffusion method. It was observed that Q. incana Roxb. showed significant antibacterial activity against Gram-positive and Gram-negative bacteria. n-Butanol fraction showed maximum activity against Micrococcus leuteus with 19 mm zone of inhibition. n-Butanol fraction of Q. incana Roxb. showed immense antifungal activity against Aspergillus niger (32 mm ± 0.55) and A. flavus (28 mm ± 0.45). Similarly n-butanol fraction showed relatively good antioxidant activity with IC50 value of 55.4 ± 0.21 μg/mL. The NO scavenging activity of ethyl acetate fraction (IC50 = 23.21 ± 0.31 μg/mL) was fairly good compared to other fractions. The current study of Q. incana Roxb. suggests the presences of synergetic action of some biological active compounds that may be present in the leaves of medicinal plant. Further studies are needed to better characterize the important active constituents responsible for the antimicrobial, antioxidant and free radical scavenging activity.

Concepts: Bacteria, Microbiology, Radical, Nitric oxide, Tannin, Gram-negative bacteria, Gallic acid, Gram-positive bacteria

139

Nontuberculous mycobacteria (NTM), including Mycobacterium avium complex (MAC), cause opportunistic chronic pulmonary infections. Notably, MAC susceptibility is regulated by various factors, including the host immune system. Persimmon (Ebenaceae Diospyros kaki Thunb.) tannin is a condensed tannin composed of a polymer of catechin groups. It is well known that condensed tannins have high antioxidant activity and bacteriostatic properties. However, it is hypothesized that condensed tannins might need to be digested and/or fermented into smaller molecules in vivo prior to being absorbed into the body to perform beneficial functions. In this study, we evaluated the effects of soluble persimmon-derived tannins on opportunistic MAC disease. Soluble tannins were hydrolyzed and evaluated by the oxygen radical absorbance capacity (ORAC) method. The ORAC value of soluble tannin hydrolysate was approximately five times greater than that of soluble tannin powder. In addition, soluble tannin hydrolysate exhibited high bacteriostatic activity against MAC in vitro. Furthermore, in an in vivo study, MAC infected mice fed a soluble tannin-containing diet showed significantly higher anti-bacterial activity against MAC and less pulmonary granuloma formation compared with those fed a control diet. Tumor necrosis factor α and inducible nitric oxide synthase levels were significantly lower in lungs of the soluble tannin diet group compared with the control diet group. Moreover, proinflammatory cytokines induced by MAC stimulation of bone marrow-derived macrophages were significantly decreased by addition of soluble tannin hydrolysate. These data suggest that soluble tannin from persimmons might attenuate the pathogenesis of pulmonary NTM infection.

Concepts: Immune system, Tuberculosis, Mycobacterium, Nitric oxide, Mycobacterium avium complex, Nontuberculous mycobacteria, Persimmon, Tannin

49

The purpose of this study to examine support for indoor tanning policies and correlates of policy support among young adult women who indoor tan. Non-Hispanic white women ages 18-30 who indoor tanned in the past year (n = 356, M 23.3 age, SD 3.1) recruited in the Washington, DC area from 2013 to 2016 completed measures of indoor tanning behaviors, attitudes, perceptions, beliefs, and policy support. Most women in the sample supported policies to prevent children under the age of 18 from indoor tanning (74.0 %) and stronger warnings about the risks of indoor tanning on tanning devices (77.6 %); only 10.1 % supported a total ban. In multivariable analyses, support for individual indoor tanning policies varied by demographics (e.g., age), frequent indoor tanning behavior, indoor tanning beliefs, and risk perceptions. Non-Hispanic white young adult women who indoor tan, the primary consumers of indoor tanning, and a high-risk population, largely support indoor tanning prevention policies implemented by many state governments and those currently under review for national enactment. Given low levels of support for a total indoor tanning ban, support for other potential policies (e.g., increasing the minimum age to 21) should be investigated to inform future steps to reduce indoor tanning and the associated health risks.

Concepts: Psychology, Implementation, White people, Tannin, Sun tanning, Tanning

29

The antioxidant properties of extracts of Sybaris liquorice roots have been assessed using 2,2'-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity assay. The extracts, obtained by Soxhlet extraction (Et(2)O, AcOEt, MeOH and BuOH) of the yellow (inner part) and brown (cortex) root powders ensuing from decortication of the raw dry roots, followed by separation and powderisation, were analysed for their scavenging activity by evaluating the colourimetric decrease in the absorbance of DPPH. The highest antioxidant activity (98.39 ± 0.56%) was observed in the case of the Et(2)O extract of the brown powder, at a concentration of 3.33 mg mL(-1). Moreover, the total phenolic content of the extracts was determined using the Folin-Ciocalteu reagent and expressed as milligram gallic acid equivalent per gram of dry extract. Our results show that the Et(2)O extract of the liquorice root cortex could be used as an attractive natural source of antioxidant additives for food, cosmetic or pharmaceutical applications.

Concepts: Antioxidant, Analytical chemistry, Root, Tannin, Polyphenol antioxidant, Gallic acid, Propyl gallate, Lowry protein assay

29

Tea leaves contain varying amounts of polyphenols of which the majority are catechins. There has been a sizable amount of research on the potential effect of green tea catechins for cancer risk, cardiovascular disease risk and weight loss; all conditions that are relevant to mid-life health. The aim was to produce an overview of the evidence for green tea for these three important health conditions.

Concepts: Medicine, Tea, Catechin, Camellia sinensis, Green tea, Tannin, Polyphenol, Epigallocatechin gallate

28

Alzheimer disease (AD) brain is characterized by extracellular plaques of amyloid β (Aβ) peptide with reactive microglia. This study aimed to determine whether a dietary intervention could attenuate microgliosis. Memory was assessed in 12-mo-old male amyloid precursor protein/presenilin 1 (APP/PS1) transgenic mice via Barnes maze testing followed by division into either a control-fed group provided free access to normal chow and water or a treatment group provided free access to normal chow and drinking water supplemented with pomegranate extract (6.25 mL/L) for 3 mo followed by repeat Barnes maze testing for both groups. Three months of pomegranate feeding decreased the path length to escape of mice compared with their initial 12-mo values (P < 0.05) and their control-fed counterparts (P < 0.05). Brains of the 3-mo study pomegranate-fed mice had lower tumor necrosis factor α (TNF-α) concentrations (P < 0.05) and lower nuclear factor of activated T-cell (NFAT) transcriptional activity (P < 0.05) compared with controls. Brains of the 3-mo pomegranate or control mice were also compared with an additional control group of 12-mo-old mice for histologic analysis. Immunocytochemistry showed that pomegranate- but not control-fed mice had attenuated microgliosis (P < 0.05) and Aβ plaque deposition (P < 0.05) compared with 12-mo-old mice. An additional behavioral study again used 12-mo-old male APP/PS1 mice tested by T-maze followed by division into a control group provided with free access to normal chow and sugar supplemented drinking water or a treatment group provided with normal chow and pomegranate extract-supplemented drinking water (6.25 mL/L) for 1 mo followed by repeat T-maze testing in both groups. One month of pomegranate feeding increased spontaneous alternations versus control-fed mice (P < 0.05). Cell culture experiments verified that 2 polyphenol components of pomegranate extract, punicalagin and ellagic acid, attenuated NFAT activity in a reporter cell line (P < 0.05) and decreased Aβ-stimulated TNF-α secretion by murine microglia (P < 0.05). These data indicate that dietary pomegranate produces brain antiinflammatory effects that may attenuate AD progression.

Concepts: Gene expression, Molecular biology, Tumor necrosis factor-alpha, Tannin, Genetically modified organism, Transgenic plant, Ice-minus bacteria, Pomegranate

28

The butanol-HCl spectrophotometric assay is widely used for quantifying extractable and insoluble condensed tannins (CT, syn. proanthocyanidins) in foods, feeds, and foliage of herbaceous and woody plants, but the method underestimates total CT content when applied directly to plant material. To improve CT quantitation, we tested various cosolvents with butanol-HCl and found that acetone increased anthocyanidin yields from two forage Lotus species having contrasting procyanidin and prodelphinidin compositions. A butanol-HCl-iron assay run with 50% (v/v) acetone gave linear responses with Lotus CT standards and increased estimates of total CT in Lotus herbage and leaves by up to 3.2-fold over the conventional method run without acetone. The use of thiolysis to determine the purity of CT standards further improved quantitation. Gel-state 13C and 1H-13C HSQC NMR spectra of insoluble residues collected after butanol-HCl assays revealed that acetone increased anthocyanidin yields by facilitating complete solubilization of CT from tissue.

Concepts: Plant, Fern, Leaf, Enzyme assay, Tannin, Proanthocyanidin, Oak, Vascular tissue