DOCSLIB.ORG

Peanut-Skin Polyphenols, Procyanidin A1 and Epicatechin-(4 !6)-Epicatechin-(2 !O!7, 4 !8)-Catechin, Exert Cholesterol Micelle-Degrading Activity in Vitro

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Peanut-Skin Polyphenols, Procyanidin A1 and Epicatechin-(4 !6)-Epicatechin-(2 !O!7, 4 !8)-Catechin, Exert Cholesterol Micelle-Degrading Activity in Vitro 121023 (214) Biosci. Biotechnol. Biochem., 77 (6), 121023-1–4, 2013 Note Peanut-Skin Polyphenols, Procyanidin A1 and Epicatechin-(4 !6)-epicatechin-(2 !O!7, 4 !8)-catechin, Exert Cholesterol Micelle-Degrading Activity in Vitro Tomoko TAMURA,1 Naoko INOUE,1 Megumi OZAWA,1 Akiko SHIMIZU-IBUKA,2 Soichi ARAI,1 y Naoki ABE,1 Hiroyuki KOSHINO,3 and Kiyoshi MURA1; 1Department of Nutritional Science, Faculty of Applied Bioscience, Tokyo University of Agriculture, 1-1-1 Sakuragaoka, Setagaya-ku, Tokyo 156-8502, Japan 2Department of Material and Biological Chemistry, Faculty of Science, Yamagata University, 1-4-12 Kojirakawa-machi, Yamagata 990-8560, Japan 3RIKEN Advanced Science Institute, 2-1 Hirosawa, Wako, Saitama 351-0198, Japan Received January 4, 2013; Accepted February 27, 2013; Online Publication, June 7, 2013 [doi:10.1271/bbb.121023] We identified epicatechin-(4 !6)-epicatechin-(2 ! Here we report that a major peanut-skin polyphenol O!7, 4 !8)-catechin (EEC) in the skin of the peanut having a cholesterol micelle-degrading effect is epica- (Arachis hypogaea L.). EEC (a trimer) showed more techin-(4 !6)-epicatechin-(2 !O!7, 4 !8) cate- potent cholesterol micelle-degrading activity than pro- chin (EEC), in addition to the previously identified cyanidinAdvance A1 (a dimer) did in vitro. The hypercholester- View 3) procyanidin A1. olemia suppressing effect of a peanut skin polyphenol on Roasted peanut skin (40 g) was boiled in purified rats fed high-cholesterol diet in our preceding experi- water (1,000 mL) for 30 min, and the supernatant was ments might thus have been due primarily to a micelle taken by decantation and filtration. This treatment was degrading effect in the intestine. done in triplicate, and then the three supernatants were pooled prior to vacuum concentration to 1,000 mL. The Key words: catechin; cholesterol; micellar solubility; total polyphenol in this concentrate was quantified by peanut skin; procyanidin Folin-Ciocalteu assay.6) As catechin equivalent, 4.65 g of polyphenol was obtained from 40 g of peanut skin. A great many polyphenols of food origin are known Then a 50-mL aliquot of the 1,000-mL polyphenol to have physiologic effects, including anti-oxidative, solution was subjectedProofs to filtration with an ultrafilter anti-inflammation, and antimicrobial one.1) These are (MWCO 3000; Advantec, Tokyo). Seventy-five point closely related to stereochemistry. Tatsuno et al.2) five mg of polyphenol was obtained in a lower-molecu- indicated that within the group of procyanidins, the lar-weight (Mr < 3000) fraction, and its filtrate dimers and trimers showed similar suppressive activ- (Mr < 3000) was chromatographed on a TSK-gel ities to TNF- and IL-6, whereas the tetramers showed Toyopearl HW-40 F column (26 Â 800 mm) (Tosoh no such activity. We have found that polyphenols Bioscience, Tokyo) using methanol as the mobile phase. occurring in peanut skin are anti-allergenic by sup- Procyanidin A1 was obtained from the fourth of gel pression of degranulation in immunocytics.3) In this filtration peak as described previously.3) The remaining case, procyanidin A2 showed inhibitory activity like polyphenols in the TSK-gel Toyopearl HW-40 F column procyanidin A1, while (þ)-catechin was not involved were eluted with 80% acetone. The resulting eluate in inhibiting -hexosaminidase release.3) Almost all contained 60.8% polyphenol. Then, the eluate was studies of the mechanism of the cholesterol micelle- purified by chromatography on a YMC gel ODS-AQ degrading effect of the polyphenols have been con- 12S50 column (YMC, Kyoto, Japan) pre-equilibrated ducted with extract solutions containing polyphenol or with solvent A (0.1% formic acid v/v). Elution was with monomeric polyphenols: catechin, epicatechin, and conducted by linear gradient (20%!40% methanol as EGCg. solvent B) at a flow rate of 5 mL/min for 270 min, and We have reported that a peanut-skin polyphenol effect was separated into peaks. A major component of the occurred in the skin at 5% on a dry-matter basis and had main peak of the chromatography was isolated. a serum cholesterol-reducing effect when administrated The primary nuclear magnetic resonance (NMR) to rats fed a high-cholesterol diet, and that the effect was spectra of a major component were recorded by JNM- predominant at lower-molecular-weights.4,5) In addition, ECX 400 (JEOL, Tokyo) at 400 MHz (1H) and at 13 a major portion of dietary cholesterol was found to reach 100 MHz ( C), with methanol-d4 as solvent and the feces after degrading the intestinal cholesterol tetramethylsilane as internal standard at ambient tem- micelle without entry into the blood.5) perature. At that temperature, the 1H-NMR (400 MHz) y To whom correspondence should be addressed. Tel: +81-3-5477-2459; Fax: +81-3-5477-2392; E-mail: [email protected] Abbreviations: DQF-COSY, double-quantum filtered correlation spectroscopy; EEC, epicatechin-(4 !6)-epicatechin-(2 !O!7, 4 !8)- catechin; EGCg, epigallocatechingallate; HMBC, heteronuclear multiple-bond correlation; HPLC, high performance liquid chromatography; HSQC, heteronuclear single-quantum coherence; NMR, nuclear magnetic resonance; NOESY, nuclear overhauser effect correlation spectroscopy; 2D, two- dimensional 121023-2 T. TAMURA et al. spectrum of major component gave a number of broad assignments were achieved by careful spectral analysis. signals, and hence full assignments for structure iden- There are summarized in Table 1. The connectivity of tification were not completed. It has been reported that the inter-unit was confirmed by HMBC correlations trimeric procyanidin with an interflavonoid linkage from H-4 to C-50, C-60, and C70, and also from H-40 to between 4 and 6 or between 4 and 8 has atropisomers C-700, C-800, and C-800a. In the NOESY experiment with owing to slow rotation of the linkage bond at ambient two mixing times (100 ms and 500 ms), several chemical temperature.7) The behavior of the 1H-NMR spectrum in exchange cross peaks were observed for the two our experiment suggested that is component possessed atropisomers. Based on the NMR spectral data, the the 4 - > 6- or the 4 - > 8-interflavonoid linkage. structure of the major component based on chromatog- Further NMR spectral analysis of 1H-(600 MHz), 13C- raphy on the YMC gel ODS-AQ 12S50 column was (150 MHz), and several sets of two-dimensional (2D) determined to be in agreement with the data for an NMR data, including DQF-COSY, HSQC, HMBC, and abundance ratio of a 1:1 mixture of the two atropisomers NOESY, were recorded under low temperature condi- (conformers-1 and -2) of a epicatechin-(4 !6)-epica- tions (À40 C). Under these conditions, two sets of techin-(2 !O!7, 4 !8) catechin, ECC (Fig. 1). 1H NMR signals were observed for the major compo- The conformations of the atropisomers were eluci- nent from peak A, at ratio of abundance of 1:1 of two dated by a NOESY experiment. NOEZY correlations atropisomers (conformers-1 and -2). Complete NMR between H-2 and H-1200 and H-1600 and between H-8 and 1 13 Table 1. H and C NMR Spectral Data for EEC in CD3OD at À40 C 13 1 C-NMR (150 MHz) H-NMR (600 MHz) in CD3OD at À40 C No. conformer-1 conformer-2 conformer-1 conformer-2 2 77.75 76.91 5.48 s 5.03 s Advance3 73.46 72.85 View 3.79 br.s 3.85 br.s 4 36.65 37.41 4.62 br.s 4.64 br.s 4a 103.25 102.28 — — 5 157.96 158.19 — — 6 95.42 95.71 5.83 d (2.3) 5.89 d (2.3) 7 156.79 157.76 — — 8 95.71 95.42 6.16 d (2.3) 5.93 d (2.3) 8a 157.76 157.84 — — 9 132.90 132.59 — — 10 115.08 114.97 6.91 d (1.8) 6.83 d (1.3) 11 145.90 145.75 — — 12 145.54a 145.42 — — 13 115.67 115.49 6.70 d (8.2)Proofs 6.66 d (8.3) 14 119.32 119.01 6.59 dd (8.2, 1.8) 6.61 dd (8.3, 1.3) 20 99.78 100.05 — — 30 67.54 67.65 4.03 s 4.07 d (3.5) 40 29.03 29.48 4.03 s 4.16 d (3.5) 40a 104.06 103.67 — — 50 154.86 154.05 — — 60 111.33 110.58 — — 70 156.31 157.19 — — 80 96.27 97.37 6.19 s 6.01 s 80a 151.92 151.92 — — 110 131.97b 131.99b —— 120 115.40c 115.42c 7.07 d (1.9) 7.09 d (1.9) 130 145.54a 145.58a —— 140 146.67d 146.72d —— 150 115.30e 115.35e 6.78 d (7.8) 6.79 d (8.3) 160 119.69f 119.72f 6.97 dd (7.8, 1.9) 6.99 dd (8.3, 1.9) 200 85.77 85.14 4.35 d (9.2) 4.73 d (8.3) 300 68.91 68.14 3.87 ddd (10.1, 9.2, 5.9) 4.19 ddd (9.2, 8.3, 5.5) 400 31.18 29.24 3.06 dd (16.1, 5.9) 2.99 dd (16.1, 5.5) 2.46 dd (16.1, 10.1) 2.55 dd (16.1, 9.2) 400a 103.67 103.00 — — 500 156.22 156.31 — — 600 96.64 96.39 6.098 s 6.096 s 700 152.20 152.20 — — 800 106.73 106.26 — — 800a 151.76 151.22 — — 1100 129.50 129.91 — — 1200 117.88 115.75 6.72 d (1.4) 6.96 d (1.4) 1300 145.37 146.17 — — 1400 146.45 148.86 — — 1500 118.20 116.54 7.03 d (7.8) 6.85 d (8.2) 1600 119.45 121.11 6.77 dd (7.8, 1.4) 6.89 dd (8.2, 1.4) a–f, These assignments are exchangeable.
Load more

Recommended publications
  • Proanthocyanidin Metabolism, a Mini Review
    Nutrition and Aging 2 (2014) 111–116 111 DOI 10.3233/NUA-140038 IOS Press Proanthocyanidin Metabolism, a mini review Y.Y. Choy and A.L. Waterhouse∗ Viticulture and Enology, University of California, Davis, CA, USA Abstract. There is emerging evidence suggesting that consumption of beverage and food rich in polyphenol may offer protective effects against various neurodegenerative, cardiovascular diseases and cancers. Proanthocyanidins (PACs) are one of the most abundant polyphenol in human diets, but also one of the least absorbed polyphenol mostly due to their size and structure com- plexity. PACs or condensed tannins are oligomers and polymers of monomeric unit flavan-3-ol (+)-catechin or (−)-epicatechin. To date, the absorption and metabolism of PACs are still remains largely unknown. The aim of this mini review was to highlight the absorption and metabolism of PACs, their effect in the gut and sample preparation for analysis. Ultimately, the potential bioactivities derived from the interaction between PACs metabolites and the gut microbiota warrants further investigation. Keywords: Proanthocyanidins, phenolic acids, metabolism, colon 1. Introduction derived subunits. PACs that consists exclusively of (−)-epicatechin, (+)-catechin units, are known as pro- Polyphenols are among the ubiquitous constituents cyanidins because only cyanidin is released in acid, of foods of plant origins and are widely distributed and comprised the largest class of PACs, while those throughout the plant kingdom. Polyphenols can be with gallocatechin units release delphinidin. The size categorized into different groups such as flavonoids, or molecular weight of PACs can be expressed as phenolic acids, stilbenes and lignans. The flavonoids mean degree of polymerization (mDP).
    [Show full text]
  • 2019, 17–28 Assessment of Antioxidants by Hplc-Ms in Grapevine Seeds
    Acta Sci. Pol. Hortorum Cultus, 18(6) 2019, 17–28 https://czasopisma.up.lublin.pl/index.php/asphc ISSN 1644-0692 e-ISSN 2545-1405 DOI: 10.24326/asphc.2019.6.2 ORIGINAL PAPER Accepted: 4.03.2019 ASSESSMENT OF ANTIOXIDANTS BY HPLC-MS IN GRAPEVINE SEEDS Lenka Sochorova1, Borivoj Klejdus2, Mojmir Baron1, Tunde Jurikova3, Jiri Mlcek4, Jiri Sochor1, Sezai Ercisli5, Muhammed Kupe5 1 Department of Viticulture and Enology, Faculty of Horticulture, Mendel University in Brno, Valticka 337, CZ-691 44 Lednice, Czech Republic 2 Department of Chemistry and Biochemistry, Faculty of Agronomy, Mendel University in Brno, Zemedelska 1, CZ-613 00 Brno, Czech Republic 3 Department of Natural and Informatics Sciences, Faculty of Central European Studies, Constantine the Philosopher University in Nitra, Drazovska 4, 949 74 Nitra, Slovakia 4 Department of Food Analysis and Chemistry, Faculty of Technology, Tomas Bata University in Zlin, nam. T. G. Masaryka 5555, 760 01 Zlin Czech Republic 5 Department of Horticulture, Agricultural Faculty, Ataturk University, 25240 Erzurum, Turkey ABSTRACT It is well known, that grapevine seeds are rich in significant antioxidants. However, the issue of dealing with the analysis and comparison of antioxidant components in the seeds of Vitis vinifera L. in individual cultivars has not yet been sufficiently studied. The experiment was performed with extracts of three varieties (Blaufränkish, Italian Riesling and Cabernet Moravia) and three interspecific cultivars (Nativa, Marlen and Kofranka). Contents of nine major flavonoids (apigenin, astragalin, hyperoside, isorhamnetin, kaempferol, myricetin, quercetin, quercitrin and rutin) and two procyanidins (procyanidin A2 and procyanidin B1) were assessed by the HPLC/MS method.
    [Show full text]
  • Docking Characterization and in Vitro Inhibitory Activity of Flavan-3-Ols and Dimeric Proanthocyanidins Against the Main Protease Activity of SARS-Cov-2
    ORIGINAL RESEARCH published: 30 November 2020 doi: 10.3389/fpls.2020.601316 Docking Characterization and in vitro Inhibitory Activity of Flavan-3-ols and Dimeric Proanthocyanidins Against the Main Protease Activity of SARS-Cov-2 Yue Zhu and De-Yu Xie* Department of Plant and Microbial Biology, North Carolina State University, Raleigh, NC, United States We report to use the main protease (Mpro) of SARS-Cov-2 to screen plant flavan-3-ols and proanthocyanidins. Twelve compounds, (–)-afzelechin (AF), (–)-epiafzelechin (EAF), (+)-catechin (CA), (–)-epicatechin (EC), (+)-gallocatechin (GC), (–)-epigallocatechin Edited by: (EGC), (+)-catechin-3-O-gallate (CAG), (–)-epicatechin-3-O-gallate (ECG), Guodong Wang, Chinese Academy of Sciences, China (–)-gallocatechin-3-O-gallate (GCG), (–)-epigallocatechin-3-O-gallate (EGCG), Reviewed by: procyanidin A2 (PA2), and procyanidin B2 (PB2), were selected for docking simulation. pro Hiroshi Noguchi, The resulting data predicted that all 12 metabolites could bind to M . The affinity Nihon Pharmaceutical scores of PA2 and PB2 were predicted to be −9.2, followed by ECG, GCG, EGCG, University, Japan Ericsson Coy-Barrera, and CAG, −8.3 to −8.7, and then six flavan-3-ol aglycones, −7.0 to −7.7. Docking Universidad Militar Nueva characterization predicted that these compounds bound to three or four subsites (S1, Granada, Colombia S1′, S2, and S4) in the binding pocket of Mpro via different spatial ways and various *Correspondence: De-Yu Xie formation of one to four hydrogen bonds. In vitro analysis with 10 available compounds pro [email protected] showed that CAG, ECG, GCG, EGCG, and PB2 inhibited the M activity with an IC50 value, 2.98 ± 0.21, 5.21 ± 0.5, 6.38 ± 0.5, 7.51 ± 0.21, and 75.3 ± 1.29 µM, Specialty section: respectively, while CA, EC, EGC, GC, and PA2 did not have inhibitory activities.
    [Show full text]
  • UC Santa Barbara Dissertation Template
    UNIVERSITY OF CALIFORNIA Santa Barbara A-type Procyanidins and Their Effects on the Aggregation of Tau Prevalent in Alzheimer’s Disease A Thesis submitted in partial satisfaction of the requirements for the degree Master of Science in Biochemistry and Molecular Biology by Michael James Weingart Committee in charge: Professor John Lew, Chair Professor Rolf E. Christoffersen Professor Benjamin E. Reese January 2018 The thesis of Michael James Weingart is approved. ________________________________________ Benjamin E. Reese ________________________________________ Rolf E. Christoffersen ________________________________________ John Lew, Committee Chair January 2018 A-type Procyanidins and Their Effects on the Aggregation of Tau Prevalent in Alzheimer’s Disease Copyright © 2018 by Michael James Weingart iii Acknowledgements Thank you to Professor John Lew and Dylan Peterson for welcoming me into the lab, for giving me the opportunity to work on this project in the first place, and for teaching me pretty much everything I know about lab work. Thank you to Professors Ben Reese and Rolf Christoffersen for taking time out of their schedules to serve on my committee. And thank you to my parents for always being supportive no matter what I decided to pursue. iv Abstract A-type Procyanidins and Their Effects on the Aggregation of Tau Prevalent in Alzheimer’s Disease by Michael James Weingart Alzheimer’s disease (AD) affects over 40 million people worldwide: a number that is expected to grow to over 100 million by 2050.1 Despite this, there is a shortage of AD drugs on the market, with only five having been FDA approved, and no new ones since 2003.2 A major problem is that these drugs are merely symptomatic treatments.
    [Show full text]
  • Masquelier's Grape Seed Extract: from Basic Flavonoid Research to a Well
    Weseler and Bast Nutrition Journal (2017) 16:5 DOI 10.1186/s12937-016-0218-1 REVIEW Open Access Masquelier’s grape seed extract: from basic flavonoid research to a well-characterized food supplement with health benefits Antje R. Weseler* and Aalt Bast Abstract Careful characterization and standardization of the composition of plant-derived food supplements is essential to establish a cause-effect relationship between the intake of that product and its health effect. In this review we follow a specific grape seed extract containing monomeric and oligomeric flavan-3-ols from its creation by Jack Masquelier in 1947 towards a botanical remedy and nutraceutical with proven health benefits. The preparation’s research history parallels the advancing insights in the fields of molecular biology, medicine, plant and nutritional sciences during the last 70 years. Analysis of the extract’s flavanol composition emerged from unspecific colorimetric assays to precise high performance liquid chromatography - mass spectrometry and proton nuclear magnetic resonance fingerprinting techniques. The early recognition of the preparation’s auspicious effects on the permeability of vascular capillaries directed research to unravel the underlying cellular and molecular mechanisms. Recent clinical data revealed a multitude of favorable alterations in the vasculature upon an 8 weeks supplementation whichsummedupinahealthbenefitoftheextractin healthy humans. Changes in gene expression of inflammatory pathways in the volunteers’ leukocytes were suggested to be involved
    [Show full text]
  • Extracts of Peanut Skins As a Source of Bioactive Compounds: Methodology and Applications
    applied sciences Review Extracts of Peanut Skins as a Source of Bioactive Compounds: Methodology and Applications Lisa L. Dean Food Science and Market Quality and Handling Research Unit, USDA, ARS, SEA, Raleigh, NC 27695-7624, USA; [email protected]; Tel.: +1-919-515-9110 Received: 30 October 2020; Accepted: 26 November 2020; Published: 29 November 2020 Featured Application: Optimized extraction of polyphenols from peanut skins. Abstract: Peanut skins are a waste product of the peanut processing industry with little commercial value. They are also significant sources of the polyphenolic compounds that are noted for their bioactivity. The extraction procedures for these compounds range from simple single solvent extracts to sophisticated separation schemes to isolate and identify the large range of compounds present. To take advantage of the bioactivities attributed to the polyphenols present, a range of products both edible and nonedible containing peanut skin extracts have been developed. This review presents the range of studies to date that are dedicated to extracting these compounds from peanut skins and their various applications. Keywords: peanut skins; peanut testa; peanut processing; polyphenols; procyanidins; agricultural waste; bioactivity; antioxidants 1. Introduction The global production of peanuts is projected to be 47 metric tons for the 2020 crop year [1]. In addition to the edible kernel, the peanut seed consists of the woody outer shell and a paper-like substance that surrounds the kernel itself known as the testa or skin. For most peanut products, the skin is removed and discarded [2]. The skin removal is done by a process known as blanching, which subjects the shelled raw peanut kernels to mild dry heat treatment and mechanical abrasion.
    [Show full text]
  • Phenolic Fractions from Vaccinium Vitis-Idaea L. and Their Antioxidant and Anticancer Activities Assessment
    antioxidants Article Phenolic Fractions from Vaccinium vitis-idaea L. and Their Antioxidant and Anticancer Activities Assessment Gabriele Vilkickyte 1,* , Lina Raudone 1,2 and Vilma Petrikaite 3 1 Laboratory of Biopharmaceutical Research, Institute of Pharmaceutical Technologies, Lithuanian University of Health Sciences, Sukileliu av. 13, LT-50162 Kaunas, Lithuania; [email protected] 2 Department of Pharmacognosy, Lithuanian University of Health Sciences, Sukileliu av. 13, LT-50162 Kaunas, Lithuania 3 Laboratory of Drug Targets Histopathology, Institute of Cardiology, Lithuanian University of Health Sciences, Sukileliu av. 13, LT-50162 Kaunas, Lithuania; [email protected] * Correspondence: [email protected]; Tel.: +370-622-34977 Received: 12 November 2020; Accepted: 10 December 2020; Published: 11 December 2020 Abstract: Lingonberry leaves and fruits are associated with a range of potential bioactivities related to their phenolic content and composition, but the identification of major biological activity markers remains limited. The present study aimed at the isolation of lingonberry phenolic fractions and biological activity evaluation of them. Crude dry extracts of lingonberry leaves and fruits were fractionated by chromatography using Sephadex LH-20 and analyzed by validated HPLC-PDA method. For each fraction, the anticancer activity against human clear cell renal cell carcinoma (CaKi-1), human colon adenocarcinoma (HT-29), and human malignant melanoma (IGR39) cell lines was determined using MTT assay, and the radical scavenging, reducing, and chelating activities were investigated using ABTS, FRAP, and FIC assays, respectively. Further, 28 phenolics were identified and quantified in the crude extract of lingonberry leaves and 37 in the extract of fruits. These compounds, during fractionation steps, were selectively eluted into active fractions, enriched with different groups of phenolics—monophenols, anthocyanins, phenolic acids, catechins, flavonols, or proanthocyanidins.
    [Show full text]
  • Peel of Traditional Apple Varieties As a Great Source of Bioactive Compounds: Extraction by Micro-Matrix Solid-Phase Dispersion
    foods Article Peel of Traditional Apple Varieties as a Great Source of Bioactive Compounds: Extraction by Micro-Matrix Solid-Phase Dispersion Ante Lonˇcari´c 1,* , Katarina Matanovi´c 1, Perla Ferrer 2 , Tihomir Kovaˇc 1 , Bojan Šarkanj 3 , Martina Skendrovi´cBabojeli´c 4 and Marta Lores 2 1 Faculty of Food Technology Osijek, Josip Juraj Strossmayer University of Osijek, Franje Kuhaˇca20, HR 31000 Osijek, Croatia; [email protected] (K.M.); [email protected] (T.K.) 2 Faculty of Chemistry, University of Santiago de Compostela, Campus Vida, E-15782 Santiago de Compostela, Spain; [email protected] (P.F.); [email protected] (M.L.) 3 Department of Food Technology, University Centre Koprivnica, University North, Trg dr. Žarka Dolinara 1, 48000 Koprivnica, Croatia; [email protected] 4 Faculty of Agriculture, University of Zagreb, Svetošimunska 25, 10000 Zagreb, Croatia; [email protected] * Correspondence: [email protected]; Tel.: +385-31-544-350 Received: 4 December 2019; Accepted: 8 January 2020; Published: 11 January 2020 Abstract: Micro matrix solid phase dispersion (micro-MSPD) was optimized by response surface methodology for the extraction of polyphenols from the peel of twelve traditional and eight commercial apple varieties grown in Croatia. The optimized micro-MSPD procedure includes the use of 0.2 g of sample, 0.8 g of dispersant, a 57% solution of methanol in water as the solvent and 5 mL of extract volume. The total polyphenolic index (TPI) and antioxidant activity (AA) were measured by spectrophotometric assays. Eighteen polyphenolic compounds were identified in all investigated apples by HPLC-DAD and LC-(ESI)-MS.
    [Show full text]
  • 3′,4′-Dihydroxyphenyl-Γ-Valerolactone), a Major Microbial Metabolite of Proanthocyanidin, Attenuates THP-1 Monocyte-Endothelial Adhesion
    Article 5-(3′,4′-dihydroxyphenyl-γ-valerolactone), a Major Microbial Metabolite of Proanthocyanidin, Attenuates THP-1 Monocyte-Endothelial Adhesion Charles C. Lee 1,†, Jong Hun Kim 2,†, Ji Seung Kim 3, Yun Sil Oh 3, Seung Min Han 3, Jung Han Yoon Park 2, Ki Won Lee 2,3,* and Chang Yong Lee 1,* 1 Department of Food Science, Cornell University, Ithaca, NY 14853, USA; [email protected] 2 Research Institute of Agriculture and Life Sciences, Seoul National University, Seoul 08826, Korea; [email protected] (J.H.K.); [email protected] (J.H.Y.P.) 3 Major in Biomodulation, Department of Agricultural Biotechnology, Seoul National University, Seoul 08826, Korea; [email protected] (J.S.K.); [email protected] (Y.S.O.); [email protected] (S.M.H.) * Correspondence: [email protected] (K.W.L.); [email protected] (C.Y.L.); Tel.: +82-2-880-4661(K.W.L.); +1-607-255-0114 (C.Y.L.) † These authors contributed equally to this work. Received: 27 April 2017; Accepted: 22 June 2017; Published: 26 June 2017 Abstract: Several metabolomics of polymeric flavan-3-ols have reported that proanthocyanidins are extensively metabolized by gut microbiota. 5-(3′,4′-dihydroxyphenyl)-γ-valerolactone (DHPV) has been reported to be the major microbial metabolite of proanthocyanidins. We demonstrated that DHPV has stronger prevention effect on tumor necrosis factor (TNF)-α-stimulated adhesion of THP- 1 human monocytic cells to human umbilical vein endothelial cells compared to its potential precursors such as procyanidin A1, A2, B1 and B2, (+)catechin, (−)epicatechin and its microbial metabolites such as 3-(3,4-dihydroxyphenyl)propionic acid and 2-(3,4-dihydroxyphenyl)acetic acid.
    [Show full text]
  • Heidker Unr 0139D 12054.Pdf
    University of Nevada, Reno Metabolic Effects of a Grape Seed Procyanidin Extract and its Relation to Bile Acid Homeostasis A dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in Cell and Molecular Biology By Rebecca M. Heidker Dr. Marie-Louise Ricketts/Dissertation Advisor May, 2016 Copyright by Rebecca M. Heidker 2016 All rights reserved THE GRADUATE SCHOOL We recommend that the dissertation prepared under our supervision by REBECCA HEIDKER Entitled Metabolic Effects Of Grape Seed Procyanidin Extract On Risk Factors Of Cardiovascular Disease be accepted in partial fulfillment of the requirements for the degree of DOCTOR OF PHILOSOPHY Marie-Louise Ricketts, Advisor Patricia Berinsone, Committee Member Patricia Ellison, Committee Member Cynthia Mastick, Committee Member Thomas Kidd, Graduate School Representative David W. Zeh, Ph. D., Dean, Graduate School May, 2016 i Abstract Bile acid (BA) recirculation and synthesis are tightly regulated via communication along the gut-liver axis and assist in the regulation of triglyceride (TG) and cholesterol homeostasis. Serum TGs and cholesterol are considered to be treatable risk factors for cardiovascular disease, which is the leading cause of death both globally and in the United States. While pharmaceuticals are common treatment strategies, nearly one-third of the population use complementary and alternative (CAM) therapy alone or in conjunction with medications, consequently it is important that we understand the mechanisms by which CAM treatments function at the molecular level. It was previously demonstrated that one such CAM therapy, namely a grape seed procyanidin extract (GSPE), reduces serum TGs via the farnesoid X receptor (Fxr).
    [Show full text]
  • Identification of Proanthocyanidins from Litchi (Litchi Chinensis Sonn.) Pulp by LC-ESI- Q-TOF-MS and Their Antioxidant Activity
    RESEARCH ARTICLE Identification of Proanthocyanidins from Litchi (Litchi chinensis Sonn.) Pulp by LC-ESI- Q-TOF-MS and Their Antioxidant Activity Qiang Lv1, Fenglei Luo1, Xiaoyong Zhao1, Yu Liu2, Guibing Hu3, Chongde Sun1, Xian Li1*, Kunsong Chen1 1 Laboratory of Fruit Quality Biology/The State Agriculture Ministry Laboratory of Horticultural Plant Growth, Development and Quality Improvement, Zhejiang University, Zijingang Campus, Hangzhou, PR China, 2 College of Life Sciences, Zhejiang University, Zijingang Campus, Hangzhou, PR China, 3 College of Horticulture, South China Agricultural University, Guangzhou, Guangdong, China * [email protected] Abstract Content of total proanthocyanidins as well as total phenolics, flavonoids, antioxidant activi- ties were evaluated for litchi (Litchi chinensis Sonn.) pulp of 32 cultivars. One cultivar, OPEN ACCESS Hemaoli, showed the highest total proanthocyanidins and total phenolics, and DPPH or Citation: Lv Q, Luo F, Zhao X, Liu Y, Hu G, Sun C, et ABTS radical scavenging activities. ESI-MS and NMR analysis of the Hemaoli pulp crude al. (2015) Identification of Proanthocyanidins from epi Litchi (Litchi chinensis Sonn.) Pulp by LC-ESI-Q- extracts (HPCE) showed that procyandins composed of ( )catechin unites with degree of TOF-MS and Their Antioxidant Activity. PLoS ONE polymerization (DP) of 2–6 were dominant proanthocyanidins in HPCE. After the HPCE 10(3): e0120480. doi:10.1371/journal.pone.0120480 was fractionated by a Sephadex LH-20 column, 32 procyanidins were identified by LC-ESI- Academic Editor: Hitoshi Ashida, Kobe University, Q-TOF-MS in litchi pulp for the first time. Quantification of individual procyanidin in HPCE in- JAPAN dicated that epicatechin, procyanidin B2, procyanidin C1 and A-type procyanidin trimer Received: August 15, 2014 were the main procyanidins.
    [Show full text]
  • Water-Based Extraction of Bioactive Principles from Hawthorn, Blackcurrant Leaves and Chrysanthellum Americanum
    Water-Based Extraction of Bioactive Principles from Hawthorn, Blackcurrant Leaves and Chrysanthellum Americanum : from Experimental Laboratory Research to Homemade Preparations Phu Cao Ngoc To cite this version: Phu Cao Ngoc. Water-Based Extraction of Bioactive Principles from Hawthorn, Blackcurrant Leaves and Chrysanthellum Americanum : from Experimental Laboratory Research to Homemade Prepa- rations. Analytical chemistry. Université Montpellier, 2020. English. NNT : 2020MONTS051. tel-03173592 HAL Id: tel-03173592 https://tel.archives-ouvertes.fr/tel-03173592 Submitted on 18 Mar 2021 HAL is a multi-disciplinary open access L’archive ouverte pluridisciplinaire HAL, est archive for the deposit and dissemination of sci- destinée au dépôt et à la diffusion de documents entific research documents, whether they are pub- scientifiques de niveau recherche, publiés ou non, lished or not. The documents may come from émanant des établissements d’enseignement et de teaching and research institutions in France or recherche français ou étrangers, des laboratoires abroad, or from public or private research centers. publics ou privés. THÈSE POUR OBTENIR LE GRADE DE DOCTEUR DE L’UNIVERSITÉ DE MONTPELLIER En Chimie Analytique École doctorale sciences Chimiques Balard ED 459 Unité de recherche Institut des Biomolecules Max Mousseron Water-Based Extraction of Bioactive Principles from Hawthorn, Blackcurrant Leaves and Chrysanthellum americanum: from Experimental Laboratory Research to Homemade Preparations Présentée par Phu Cao Ngoc Le 27 Novembre 2020
    [Show full text]