DOCSLIB.ORG

Walnut Polyphenol

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text

Load more

ORYZA OIL & FAT CHEM ICAL CO., LTD.

WALNUT POLYPHENOL

Hepatoprotective & Anti-oxidative Extract
For Metabolic Syndrome

■

WALNUT POLYPHENOL-P10,P30

(Powder，Food Grade)

■■■■

WALNUT POLYPHENOL-WSP10

(Water-soluble Powder，Food Grade)

WALNUT POLYPHENOL-PC10,PC30

（Powder，Cosmetic Grade）

WALNUT POLYPHENOL-WSPC10

（Water-soluble Powder，Cosmetic Grade）

WALNUT POLYPHENOL-LC

（Water-soluble Liquid，Cosmetic Grade）

■

WALNUT SEED OIL

（Oil，Food&CosmeticGrade）

ORYZA OIL & FAT CHEMICAL CO., LTD

ver. 1.0 HS
W ALNUT POLYPHENOL ver.1.0 HS

WALNUT POLYPHENOL

Hepatoprotective & Anti-oxidative Extract For Metabolic Syndrome

1. Introduction

Recently, there is an increased awareness on metabolic syndrome – a condition characterized by a group of metabolic risk factors in one person. They include abdominal obesity, atherogenic dyslipidemia, elevated blood pressure, insulin resistance, prothrombotic state & proinflammatory state. The dominant underlying risk factors appear to be abdominal obesity and insulin resistance. In addition, non-alcoholic fatty liver disease (NAFLD) is the most commonly associated “liver” manifestation of metabolic syndrome which can progress to advance liver disease (e.g. cirrhosis) with associated morbidity and mortality. Lifestyle therapies such as weight loss significantly improve all aspects of metabolic syndrome, as well as reducing progression of NAFLD and cardiovascular mortality.
Walnut (Juglans regia L. seed) is one the most popular nuts consumed in the world.
It is loaded in polyunsaturated fatty acids – linoleic acid (LA), oleic acid and α-linolenic acid (ALA), an ω3 fatty acid. It has been used since ancient times and epidemiological studies have revealed that incorporating walnuts in a healthy diet reduces the risk of cardiovascular diseases. Recent investigations reported that walnut diet improves the function of blood vessels and lower serum cholesterol. Nevertheless, walnut is rich in micronutrients (vitamins & minerals), plant sterols and polyphenols.
A joint research project was conducted between Oryza Oil & Fat Chemical Co., Ltd. and Pola Chemical Industries, Inc. to study the physiological effects of testa of walnut. Various hydrolysable polyphenolic compounds were identified which are potent antioxidants and liver protective. Correspondingly, Walnut Polyphenol is believed to be beneficial in the treatment of metabolic syndrome.

Outer pericarp

Seed

Seed coat

Endocarp

Fig. 1. Walnuts（Juglans regia L.）

1

W ALNUT POLYPHENOL ver.1.0 HS

2. WALNUT POLYPHENOLS

Most polyphenolic compounds of walnut are loaded in the testa of walnut fruit as illustrated in Fig. 2. These are hydrolysable polyphenolic compounds as shown in Fig. 3 and its principle constituents are as listed in Table 1.

Table 1. Principle Polyphenolic

Total polyphenol （%）

Constituents and Their Respective Distribution in Walnut

Seed coats

(%)

Seeds

Pedunculagin (1) Ellagic acid (5)

Tellimagrandin I (6)

Casuarictin (7)

16.0 15.8
6.6

Dried whole seeds
Whole seeds

  • 0
  • 1
  • 2
  • 3
  • 4

4.1
Tellimagranin II (10)

Rugosin C (11) Casuarinin (12)

Fukuda T. et al., BioFactors, 21,

251-253 (2004).
1.2 1.8 1.0
Fig. 2. The Content of Polyphenols in Walnut (%) （Fukuda T. Polyphenols from walnuts: Structures and functions. IFT 2006 Annual Meeting, Orland, Florida, June 24-28, 2006）

  • OH
  • HO CH2

O

O
HO
HO
OH

  • O
  • OH

OH
HO CH2
OH
HO

  • O
  • HO

HO
O

  • OC
  • CH2
  • CO
  • HO

OC

HO

  • OH
  • O
  • O
  • OC

OH
OO
O

  • OC
  • HO

HO
O

  • OC
  • CH2

OH OH OH

  • O
  • OH
  • O

CO

  • OH
  • HO

HO

  • O
  • O

  • OC
  • OC

HO

  • HO
  • O OC
  • HO

CO

  • OH
  • OH

OC

  • OH
  • HO

HO
OH
HO

2,3-O-(S)-HHDP-D- glucopyranose (2)

OH

Strictinin (4)

OH
HO HO
OH OH
OH
HO OH

Isostrictinin (3)

OH
HO

Pedunculagin (1)

OH
OH

  • OH
  • OH
  • HO

OH
OH

OH
HO HO

  • O
  • OC

  • CH2
  • HO

HO

  • O
  • O

O
OC

  • O
  • OH

OH OH
CO
HO

HO

  • O
  • O
  • OC

O
OH OH
CH2
HO

HO
O
OC
CH2

  • O
  • OH

OH
O

  • HO
  • OC

  • O
  • OC
  • O

O

  • O
  • OC

O OC

OH

  • O
  • H

  • OC
  • OH

HO
O
HO

HO
O

  • HO
  • OH

HO
CO

  • CO
  • OH

  • OC
  • OH
  • HO

OH OH
OH
O

  • OC
  • OH
  • OH

OH
O
HO

HO
HO HO

Tellimagrandin I (6)
Ellagic acid (5)

  • HO
  • OH

  • OH
  • HO
  • OH

OH

OH
OH

Casuarictin (7)
Stenophyllanin A (8)

HO
HO
OH OH OH
OH OH OH
HO HO

  • O
  • OC
  • O

HO HO

  • OC
  • CH2
  • OH

  • CH2
  • OH

OH
OO

  • O
  • O

O
HO

  • OC
  • O
  • O
  • OC
  • OC
  • O OC

OH

OH OH

  • O
  • O

HO HO

  • O
  • OH

O
OC

  • HO
  • HOOC
  • CH2
  • HO
  • OC

O
OC
OC
OH

OH

  • OC
  • OH

OH
OO
OC

  • OC
  • OH

HO
OH H
HO

  • O
  • HO
  • OH

  • HO
  • OH

  • OH
  • CO

OH

  • OH
  • OH

OH OH
HO HO

  • O
  • OH
  • OC

  • CH2
  • OC
  • OH

O

O
OO
OC

Tellimagrandin II (10)

O OC OH

1,2,3,4,6-Penta-O-galloyl-β- D-glucopyranose (9)

HO HO
OH
HO

  • OH
  • CO
  • HO

OH

  • OC
  • OH

HO HO

Casuarinin (12)

  • OH
  • HO

OH

Rugosin C (11)

Fig. 3. Chemical Structures of Hydrolysable Polyhenolic Compounds of Walnut
2

W ALNUT POLYPHENOL ver.1.0 HS

SOD like activity

SOD様活性

Casuarinin (12)

Csuarinin (12)

54.0

EC50 (µg/mL)

Rugosin C (11)

50.0

Tellimagrandin II (10)

89.0

1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose (9)
Stenophyllanin A (8)

60.0
43.0

Casuarictin (7)

73.0

Tellimagrandin I (6)

42.0

Ellagic acid (5)

28.1

Strictinin (4)

31.0

Isostrictinin (3)

30.0

2,3-O-(HHDP)-D-glucopyranose (2)
Pedunculagin (1)

80.1
50.0

クルミポリフェノール

WALNUT POLYPHENOL

29.5

  • 0
  • 20
  • 40
  • 60
  • 80
  • 100

DPPH radical scavenging activity

DPPHラジカル消去能

Casuarinin (12)

Csuarinin (12)

0.7

50

(µg/mL)

EC
Rugosin C (11)

0.4 0.4

Tellimagrandin II (10)
1,2,3,4,6-Penta-O-galloyl-β-D-glucopyranose (9)
Stenophyllanin A (8)

1.0
0.5
0.4
0.6

Casuarictin (7)
Tellimagrandin I (6)
Ellagic acid (5)

1.2

Strictinin (4)

1.7

Isostrictinin (3)

1.1

2,3-O-(HHDP)-D-glucopyranose (2)
Pedunculagin (1)

2.1
3.7
26.2

WALNUT POLYPHENOL

クルミポリフェノール

  • 0
  • 1
  • 2
  • 3
  • 4
  • 5

  • Fig. 4.
  • (top) SOD Antioxidant Activity of Walnut Polyphenols

(bottom) DPPH Antioxidant Activity of Walnut Polyphenols
Fukuda T., et al., Antioxidative polyphenols from walnuts (Juglans regia L.).

Phytochemistry, 63, 795-801 (2003).

EC50: 50% effective concentration of sample
3

W ALNUT POLYPHENOL ver.1.0 HS

3. Hepatoprotective Effect of WALNUT POLYPHENOLS

( I ) In vivo

Liver is the second largest organ in the human body. It plays a major role in metabolism of human body including glycogen storage, plasma protein synthesis and drug detoxification. It regulates a wide variety of high volume biochemical reactions and breaks down toxic substances (e.g. chemicals, viruses, alcohol etc) which may result in toxication (Fig. 5).

Fig. 5. Liver Functions and The Effect of Walnut Polyphenols on Liver Health

( a ) The effect of Walnut Polyphenols on CCl4-induced liver damage in mice model
(detoxification)

The effect of Walnut Polyphenols on CCl4-induced liver damage was studied. This

model is a simulated human hepatitis model as a result of oxidative stress and

toxication. Upon liver damage, the liver enzymes GOT (glutamate oxaloacetate transaminase) and GPT (glutamic pyruvic transaminase) infiltrate into the blood stream resulting in elevated serum GOT & GPT levels. Walnut Polyphenols demonstrated a dose dependent lowering effect in GOT & GPT in CCl4-induced liver damage in mice model (Fig. 6). Meanwhile, Walnut Polyphenols is more superior than Curcumin, a commonly used hepatoprotective agent.

10000

GOT

9000

GPT

8000 7000 6000 5000

*
**

4000 3000 2000 1000
0

*
*

**

  • Control
  • 100
  • 200
  • Curcumin 200

Dose （mg/kg）

Fig. 6. The Effect of Walnut Polyphenols on CCl4-induced liver damage in mice model（n=8, mean±S.E., *: p<0.05, **: p<0.01）

4

W ALNUT POLYPHENOL ver.1.0 HS

【Method of Experiment】
Fasting mice (ddY, male, 5-wk old) were orally fed Walnut Polyphenols. One hour later, back of mice were subcutaneously injected with 10% CCl4 previously diluted in olive oil (5ml/kg). Blood samples were collected 20 hours later for measurement of serum GOT and GPT.

( b ) The Effect of Walnut Polyphenols on D-galactosamine–induced liver damage in mice (detoxification)

Recommended publications
  • Tannins: Current Knowledge of Food Sources, Intake, Bioavailability and Biological Effects

    Tannins: Current Knowledge of Food Sources, Intake, Bioavailability and Biological Effects

    S310 DOI 10.1002/mnfr.200900039 Mol. Nutr. Food Res. 2009, 53, S310 – S329 Review Tannins: Current knowledge of food sources, intake, bioavailability and biological effects Jos Serrano1, Riitta Puupponen-Pimi2, Andreas Dauer3, Anna-Marja Aura2 and Fulgencio Saura-Calixto4 1 Universidad Complutense de Madrid, Depto. Nutricin y Bromatologa I, Madrid, Spain 2 VTT Technical Research Center of Finland 3 Hexal AG, Holzkirchen, Germany 4 Consejo Superior de Investigaciones Cientficas, Instituto del Frio, Depto. Metabolismo y Nutricin, Madrid, Spain Tannins are a unique group of phenolic metabolites with molecular weights between 500 and 30000 Da, which are widely distributed in almost all plant foods and beverages. Proanthocyanidins and hydrolysable tannins are the two major groups of these bioactive compounds, but complex tannins containing structural elements of both groups and specific tannins in marine brown algae have also been described. Most literature data on food tannins refer only to oligomeric compounds that are extracted with aqueous-organic solvents, but a significant number of non-extractable tannins are usu- ally not mentioned in the literature. The biological effects of tannins usually depend on their grade of polymerisation and solubility. Highly polymerised tannins exhibit low bioaccessibility in the small intestine and low fermentability by colonic microflora. This review summarises a new approach to analysis of extractable and non-extractable tannins, major food sources, and effects of storage and processing on tannin content and bioavailability. Biological properties such as antioxidant, antimicro- bial and antiviral effects are also described. In addition, the role of tannins in diabetes mellitus has been discussed. Keywords: Bioavailability / Diet / Hydrolysable tannins / Proanthocyanidins / Tannins / Received: November 27, 2007; revised: January 25, 2009; accepted: February 9, 2009 1 Introduction weight having the ability to complex strongly with carbohy- drates and proteins [9].
  • Punica Granatum L

    Punica Granatum L

    Research Article Studies on antioxidant activity of red, white, and black pomegranate (Punica granatum L.) peel extract using DPPH radical scavenging method Uswatun Chasanah[1]* 1 Department of Pharmacy, Faculty of Health Science, University of Muhammadiyah Malangg, Malang, East Java, Indonesia * Corresponding Author’s Email: [email protected] ARTICLE INFO ABSTRACT Article History Pomegranate (Punica granatum L.) has high antioxidant activity. In Received September 1, 2020 Indonesia, there are red pomegranate, white pomegranate, and black Revised January 7, 2021 pomegranate. The purpose of this study was to determine the antioxidant Accepted January 14, 2021 activity of red pomegranate peel extract, white pomegranate peel extract, Published February 1, 2021 and black pomegranate peel extract. The extracts prepared by ultrasonic maceration in 96% ethanol, then evaporated until thick extract was Keywords obtained and its antioxidant activity was determined using the DPPH Antioxidant radical scavenging method. This study showed that all pomegranate peel Black pomegranate extract varieties have potent antioxidant activity and the black Red pomegranate pomegranate peel extract has the highest antioxidant power. White pomegranate Peel extract DPPH Doi 10.22219/farmasains.v5i2.13472 1. INTRODUCTION Pomegranate (Punica granatum L.) belongs to the Puricaceae family, a plant originating from the Middle East (Rana, Narzary & Ranade, 2010). All parts of the pomegranate, such as fruit (fruit juice, fruit seeds, peel fruit), leaves, flowers, roots, and bark, have therapeutic effects such as neuroprotective, antioxidant, repair vascular damage, and anti-inflammatory. The clinical application of this plant used in cancers, atherosclerosis, hyperlipidemia, carotid artery stenosis, myocardial perfusion, periodontal disease, bacterial infections, ultraviolet radiation, erectile dysfunction, male infertility, neonatal hypoxic-ischemic brain injury, Alzheimer's disease, and obesity (Jurenka, 2008; Mackler, Heber & Cooper, 2013).
  • Anti-Candida Targets and Cytotoxicity of Casuarinin Isolated from Plinia Cauliflora Leaves in a Bioactivity-Guided Study

    Anti-Candida Targets and Cytotoxicity of Casuarinin Isolated from Plinia Cauliflora Leaves in a Bioactivity-Guided Study

    Molecules 2013, 18, 8095-8108; doi:10.3390/molecules18078095 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Anti-Candida Targets and Cytotoxicity of Casuarinin Isolated from Plinia cauliflora Leaves in a Bioactivity-Guided Study Tatiana M. Souza-Moreira 1, Juliana A. Severi 1,†, Keunsook Lee 2, Kanya Preechasuth 2, Emerson Santos 1, Neil A. R. Gow 2, Carol A. Munro 2, Wagner Vilegas 3 and Rosemeire C. L. R. Pietro 1,* 1 Department of Drugs and Medicines, School of Pharmaceutical Sciences, UNESP-Univ Estadual Paulista, Rodovia Araraquara-Jau, km 1, Araraquara, 14801-902, São Paulo, Brazil; E-Mails: [email protected] (T.M.S.M.); [email protected] (J.A.S.); [email protected] (E.S.) 2 Department of Microbiology, Institute of Medical Sciences, University of Aberdeen, Foresterhill, Aberdeen, AB25 2ZD, Scotland, UK; E-Mails: [email protected] (K.L.); [email protected] (K.P.); [email protected] (N.A.R.G.); [email protected] (C.A.M.) 3 Department of Organic Chemistry, Institute of Chemistry, UNESP-Univ Estadual Paulista, R. Francisco Degni s/n, Araraquara, 14800-900, São Paulo, Brazil; E-Mail: [email protected] (W.V.) † Nowadays this author is at Department of Pharmacy and Nutrition, Centro de Ciências Agrárias, UFES-Univ Federal do Espírito Santo, Alto Universitário, Guararema, 29500-000, Alegre, ES, Brazil. * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +55-16-3301-6965; Fax: +55-16-3301-6990. Received: 27 May 2013; in revised form: 5 July 2013 / Accepted: 5 July 2013 / Published: 9 July 2013 Abstract: In addition to the bio-guided investigation of the antifungal activity of Plinia cauliflora leaves against different Candida species, the major aim of the present study was the search for targets on the fungal cell.
  • Raspberry Pomace - Composition, Properties and Application

    Raspberry Pomace - Composition, Properties and Application

    View metadata, citation and similar papers at core.ac.uk brought to you by CORE European Journal ISSN 2449-8955 Review Article of Biological Research Raspberry pomace - composition, properties and application Agnieszka Joanna Brodowska Institute of General Food Chemistry, Faculty of Biotechnology and Food Sciences, Łódź University of Technology, Stefanowskiego 4/10, 90-924 Łódź, Poland * Corresponding author: Agnieszka Brodowska; E-mail: [email protected] Received: 19 February 2017; Revised submission: 24 March 2017; Accepted: 03 April 2017 Copyright: © The Author(s) 2017. European Journal of Biological Research © T.M.Karpi ński 2017. This is an open access article licensed under the terms of the Creative Commons Attribution Non-Commercial 4.0 International License, which permits unrestricted, non-commercial use, distribution and reproduction in any medium, provided the work is properly cited. DOI : http://dx.doi.org/10.5281/zenodo.495190 ABSTRACT industry by-product, is considered as a potential food ingredient. Its pomace contains plenty of Raspberry pomace can be valorised due to its valuable components such as carbohydrates, nutritionally favourable effect on human health. proteins, fats, fibre, flavours, pectins, vitamins, It is an important source of polyphenols, ellagic similar to the composition of whole raspberries [2]. acid, ellagitannins, tocopherols, unsaturated fatty Moreover, raspberry pomace is rich in a large group acids, and dietary fibre. Thus, raspberry pomace of various phenolics especially ellagitannins, can be considered as a potential raw material to proanthocyanidins, anthocyanins, flavonols, and receive products rich in polyphenols or dietary phenolic acids (especially, ellagic acid) which are fibre, which can provide healthy properties to food also predominant in berries [3].
  • Classification Et Influences Des Polyphénols Du Boisde Chêne Sur La Qualité Sensorielle Des Vins (Application Du Procédé Oakscan®) Julien Michel

    Classification Et Influences Des Polyphénols Du Boisde Chêne Sur La Qualité Sensorielle Des Vins (Application Du Procédé Oakscan®) Julien Michel

    Classification et influences des polyphénols du boisde chêne sur la qualité sensorielle des vins (Application du procédé OakScan®) Julien Michel To cite this version: Julien Michel. Classification et influences des polyphénols du bois de chêne sur la qualité sensorielle des vins (Application du procédé OakScan®). Ingénierie des aliments. Université de Bordeaux Ségalen (Bordeaux 2), 2012. Français. tel-02811201 HAL Id: tel-02811201 https://hal.inrae.fr/tel-02811201 Submitted on 6 Jun 2020 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. Université Bordeaux Segalen Année 2012 Thèse n° 1989 THESE pour le DOCTORAT DE L’UNIVERSITE BORDEAUX 2 Mention : Sciences, Technologie, Santé Option : Œnologie Présentée et soutenue publiquement le 14 décembre 2012 par MICHEL Julien Né le 8 mars 1984 à Bordeaux, France ****************************** Classification et influences des polyphénols du bois de chêne sur la qualité sensorielle des vins (Application du procédé Oakscan®) ****************************** Membres du Jury M. F. ZAMORA, Professeur, Universitat Rovira i Virgili ......................................... Rapporteur M.J. RICARDO DA SILVA, Professeur, Universidade de Lisbonne ........................ Rapporteur M. B. CHARRIER, Professeur, Université de Pau ..................................................... Examinateur M. M. JOURDES, Maître de Conférences, Université Bordeaux Segalen ................. Examinateur M. P.L.
  • Universidade Federal Do Rio De Janeiro Kim Ohanna

    Universidade Federal Do Rio De Janeiro Kim Ohanna

    UNIVERSIDADE FEDERAL DO RIO DE JANEIRO KIM OHANNA PIMENTA INADA EFFECT OF TECHNOLOGICAL PROCESSES ON PHENOLIC COMPOUNDS CONTENTS OF JABUTICABA (MYRCIARIA JABOTICABA) PEEL AND SEED AND INVESTIGATION OF THEIR ELLAGITANNINS METABOLISM IN HUMANS. RIO DE JANEIRO 2018 Kim Ohanna Pimenta Inada EFFECT OF TECHNOLOGICAL PROCESSES ON PHENOLIC COMPOUNDS CONTENTS OF JABUTICABA (MYRCIARIA JABOTICABA) PEEL AND SEED AND INVESTIGATION OF THEIR ELLAGITANNINS METABOLISM IN HUMANS. Tese de Doutorado apresentada ao Programa de Pós-Graduação em Ciências de Alimentos, Universidade Federal do Rio de Janeiro, como requisito parcial à obtenção do título de Doutor em Ciências de Alimentos Orientadores: Profa. Dra. Mariana Costa Monteiro Prof. Dr. Daniel Perrone Moreira RIO DE JANEIRO 2018 DEDICATION À minha família e às pessoas maravilhosas que apareceram na minha vida. ACKNOWLEDGMENTS Primeiramente, gostaria de agradecer a Deus por ter me dado forças para não desistir e por ter colocado na minha vida “pessoas-anjo”, que me ajudaram e me apoiaram até nos momentos em que eu achava que ia dar tudo errado. Aos meus pais Beth e Miti. Eles não mediram esforços para que eu pudesse receber uma boa educação e para que eu fosse feliz. Logo no início da graduação, a situação financeira ficou bem apertada, mas eles continuaram fazendo de tudo para me ajudar. Foram milhares de favores prestados, marmitas e caronas. Meu pai diz que fez anos de curso de inglês e espanhol, porque passou anos acordando cedo no sábado só para me levar no curso que eu fazia no Fundão. Tinha dia que eu saía do curso morta de fome e quando eu entrava no carro, tinha uma marmita com almoço, com direito até a garrafa de suco.
  • Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy

    Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy

    molecules Article Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy Valtteri Virtanen * , Susanna Räikkönen, Elina Puljula and Maarit Karonen Natural Chemistry Research Group, Department of Chemistry, University of Turku, FI-20014 Turku, Finland; [email protected] (S.R.); [email protected] (E.P.); maarit.karonen@utu.fi (M.K.) * Correspondence: vtjvir@utu.fi; Tel.: +358-29-450-3205 Abstract: Ellagitannins have antimicrobial activity, which might be related to their interactions with membrane lipids. We studied the interactions of 12 different ellagitannins and pentagalloylglucose with a lipid extract of Escherichia coli by high-resolution magic angle spinning NMR spectroscopy. The nuclear Overhauser effect was utilized to measure the cross relaxation rates between ellagitannin and lipid protons. The shifting of lipid signals in 1H NMR spectra of ellagitannin–lipid mixture due to ring current effect was also observed. The ellagitannins that showed interaction with lipids had clear structural similarities. All ellagitannins that had interactions with lipids had glucopy- ranose cores. In addition to the central polyol, the most important structural feature affecting the interaction seemed to be the structural flexibility of the ellagitannin. Even dimeric and trimeric ellagitannins could penetrate to the lipid bilayers if their structures were flexible with free galloyl and hexahydroxydiphenoyl groups. Keywords: E. coli; HR-MAS-NMR; interaction; lipid membrane; tannins; UPLC-DAD-MS Citation: Virtanen, V.; Räikkönen, S.; Puljula, E.; Karonen, M. 1. Introduction Ellagitannin–Lipid Interaction by HR-MAS NMR Spectroscopy. Tannins are a group of specialized plant metabolites, which, when included in the di- Molecules 2021, 26, 373. etary feed of ruminants, have been shown to induce many beneficial effects such as increas- https://doi.org/10.3390/ ing their effective amino acid absorption, lowering their methane production, and acting as molecules26020373 anthelmintics [1–6].
  • "Ellagic Acid, an Anticarcinogen in Fruits, Especially in Strawberries: a Review"

    "Ellagic Acid, an Anticarcinogen in Fruits, Especially in Strawberries: a Review"

    FEATURE Ellagic Acid, an Anticarcinogen in Fruits, Especially in Strawberries: A Review John L. Maasl and Gene J. Galletta2 Fruit Laboratory, U.S. Department of Agriculture, Agricultural Research Service, Beltsville, MD 20705 Gary D. Stoner3 Department of Pathology, Medical College of Ohio, Toledo, OH 43699 The various roles of ellagic acid as an an- digestibility of natural forms of ellagic acid, Mode of inhibition ticarcinogenic plant phenol, including its in- and the distribution and organ accumulation The inhibition of cancer by ellagic acid hibitory effects on chemically induced cancer, or excretion in animal systems is in progress appears to occur through the following its effect on the body, occurrence in plants at several institutions. Recent interest in el- mechanisms: and biosynthesis, allelopathic properties, ac- lagic acid in plant systems has been largely a. Inhibition of the metabolic activation tivity in regulation of plant hormones, for- for fruit-juice processing and wine industry of carcinogens. For example, ellagic acid in- mation of metal complexes, function as an applications. However, new studies also hibits the conversion of polycyclic aromatic antioxidant, insect growth and feeding in- suggest that ellagic acid participates in plant hydrocarbons [e.g., benzo (a) pyrene, 7,12- hibitor, and inheritance are reviewed and hormone regulatory systems, allelopathic and dimethylbenz (a) anthracene, and 3-methyl- discussed in relation to current and future autopathic effects, insect deterrent princi- cholanthrene], nitroso compounds (e.g., N- research. ples, and insect growth inhibition, all of which nitrosobenzylmethylamine and N -methyl- N- Ellagic acid (C14H6O8) is a naturally oc- indicate the urgent need for further research nitrosourea), and aflatoxin B1 into forms that curring phenolic constituent of many species to understand the roles of ellagic acid in the induce genetic damage (Dixit et al., 1985; from a diversity of flowering plant families.
  • Title Total Synthesis of Ellagitannins Through Regioselective

    Title Total Synthesis of Ellagitannins Through Regioselective

    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Kyoto University Research Information Repository Total Synthesis of Ellagitannins through Regioselective Title Sequential Functionalization of Unprotected Glucose. Takeuchi, Hironori; Mishiro, Kenji; Ueda, Yoshihiro; Fujimori, Author(s) Yusuke; Furuta, Takumi; Kawabata, Takeo Citation Angewandte Chemie (2015), 54(21): 6177-6180 Issue Date 2015-05-18 URL http://hdl.handle.net/2433/202533 This is the peer reviewed version of the following article:Takeuchi, H., Mishiro, K., Ueda, Y., Fujimori, Y., Furuta, T. and Kawabata, T. (2015), Total Synthesis of Ellagitannins through Regioselective Sequential Functionalization of Unprotected Glucose. Angew. Chem. Int. Right Ed., 54: 6177‒6180, which has been published in final form at http://dx.doi.org/10.1002/anie.201500700. This article may be used for non-commercial purposes in accordance with Wiley Terms and Conditions for Self-Archiving.; The full-text file will be made open to the public on 9 APR 2016 in accordance with publisher's 'Terms and Conditions for Self-Archiving'. Type Journal Article Textversion author Kyoto University COMMUNICATION Total synthesis of ellagitannins via regioselective sequential functionalization of unprotected glucose Hironori Takeuchi, Kenji Mishiro, Yoshihiro Ueda, Yusuke Fujimori, Takumi Furuta and Takeo Kawabata* This paper is dedicated to Professor Emeritus Kaoru Fuji for the celebration of his 77th birthday (Kiju). Abstract: Short-step total syntheses of natural glycosides disclosure of the attractive biological activities of this class of (ellagitannins) have been performed by sequential and natural glycosides engendered a renaissance of the interest in regioselective functionalization of hydroxy groups of unprotected their chemical synthesis.[1-4] Among the ellagitannins, we chose glucose.
  • Print This Article

    Print This Article

    Macedonian Journal of Chemistry and Chemical Engineering, Vol. 38, No. 2, pp. 149–160 (2019) MJCCA9 – 775 ISSN 1857-5552 e-ISSN 1857-5625 Received: April 23, 2019 DOI: 10.20450/mjcce.2019.1775 Accepted: October 8, 2019 Original scientific paper IDENTIFICATION AND QUANTIFICATION OF PHENOLIC COMPOUNDS IN POMEGRANATE JUICES FROM EIGHT MACEDONIAN CULTIVARS Jasmina Petreska Stanoeva1,*, Nina Peneva1, Marina Stefova1, Viktor Gjamovski2 1Institute of Chemistry, Faculty of Natural Sciences and Mathematics, Ss Cyril and Methodius University, Skopje, Republic of Macedonia 2Institute of Agriculture, Ss Cyril and Methodius University, Skopje, Republic of Macedonia [email protected] Punica granatum L. is one of the species enjoying growing interest due to its complex and unique chemical composition that encompasses the presence of anthocyanins, ellagic acid and ellagitannins, gal- lic acid and gallotannins, proanthocyanidins, flavanols and lignans. This combination is deemed respon- sible for a wide range of health-promoting biological activities. This study was focused on the analysis of flavonoids, anthocyanins and phenolic acids in eight pomegranate varieties (Punica granatum) from Macedonia, in two consecutive years. Fruits from each cultivar were washed and manually peeled, and the juice was filtered. NaF (8.5 mg) was added to 100 ml juice as a stabilizer. The samples were centrifuged for 15 min at 3000 rpm and analyzed using an HPLC/DAD/MSn method that was optimized for determination of their polyphenolic fingerprints. The dominant anthocyanin in all pomegranate varieties was cyanidin-3-glucoside followed by cya- nidin and delphinidin 3,5-diglucoside. From the results, it can be concluded that the content of anthocyanins was higher in 2016 compared to 2017.
  • Isolation of Ellagitannin Monomer and Macrocyclic Dimer from Castanopsis Carlesii Leaves

    Isolation of Ellagitannin Monomer and Macrocyclic Dimer from Castanopsis Carlesii Leaves

    HETEROCYCLES, Vol. 86, No. 1, 2012 381 HETEROCYCLES, Vol. 86, No. 1, 2012, pp. 381 - 389. © 2012 The Japan Institute of Heterocyclic Chemistry Received, 9th June, 2012, Accepted, 20th July, 2012, Published online, 24th July, 2012 DOI: 10.3987/COM-12-S(N)29 ISOLATION OF ELLAGITANNIN MONOMER AND MACROCYCLIC DIMER FROM CASTANOPSIS CARLESII LEAVES Yong-Lin Huang,a,b Takashi Tanaka,*,a Yosuke Matsuo,a Isao Kouno,a Dian-Peng Li,b and Gen-ichiro Nonakac aGraduate School of Biomedical Sciences, Nagasaki University, 1-14 Bunkyo-Machi, Nagasaki 852-8521, Japan; [email protected] bGuangxi Key Laboratory of Functional Phytochemicals Research and Utilization, Guangxi Institute of Botany, Guilin 541006, China c Usaien Pharmaceutical Company, Ltd., 1-4-6 Zaimoku, Saga 840-0055, Japan Abstract – In a phytochemical and chemotaxonomical investigation of Castanopsis species (Fagaceae), new monomeric and dimeric ellagitannins, named carlesiins A (1) and B (2), were isolated from fresh leaves of Castanopsis carlesii along with 55 known compounds. Carlesiin A was identified as 1-O-galloyl-4,6-(S)-tergalloyl-β-D-glucose. Carlesiin B is a macrocyclic ellagitannin dimer with a symmetrical structure composed of two tergalloyl and two glucopyranose moieties. Their structures were elucidated based on spectroscopic and chemical evidence. INTRODUCTION The species in the Castanopsis (Fagaceae) genus are evergreen trees that are found in East Asia, sometimes as the dominant species in a forest. These trees are often used as forestry or ornamental trees, and the wood is an important construction material. There are about 120 species in the genus, but the chemical compositions of only a few species have been studied.
  • 1 Universidade Federal Do Rio De Janeiro Instituto De

    1 Universidade Federal Do Rio De Janeiro Instituto De

    UNIVERSIDADE FEDERAL DO RIO DE JANEIRO INSTITUTO DE QUÍMICA PROGRAMA DE PÓS-GRADUAÇÃO EM CIÊNCIA DE ALIMENTOS Ana Beatriz Neves Martins DEVELOPMENT AND STABILITY OF JABUTICABA (MYRCIARIA JABOTICABA) JUICE OBTAINED BY STEAM EXTRACTION RIO DE JANEIRO 2018 1 Ana Beatriz Neves Martins DEVELOPMENT AND STABILITY OF JABUTICABA (MYRCIARIA JABOTICABA) JUICE OBTAINED BY STEAM EXTRACTION Dissertação de Mestrado apresentada ao Programa de Pós-graduação em Ciência de Alimentos do Instituto de Química, da Universidade Federal do Rio de Janeiro como parte dos requisitos necessários à obtenção do título de Mestre em Ciência de Alimentos. Orientadores: Prof.ª Mariana Costa Monteiro Prof. Daniel Perrone Moreira RIO DE JANEIRO 2018 2 3 Ana Beatriz Neves Martins DEVELOPMENT AND STABILITY OF JABUTICABA (MYRCIARIA JABOTICABA) JUICE OBTAINED BY STEAM EXTRACTION Dissertação de Mestrado apresentada ao Programa de Pós-graduação em Ciência de Alimentos do Instituto de Química, da Universidade Federal do Rio de Janeiro como parte dos requisitos necessários à obtenção do título de Mestre em Ciência de Alimentos. Aprovada por: ______________________________________________________ Presidente, Profª. Mariana Costa Monteiro, INJC/UFRJ ______________________________________________________ Profª. Maria Lúcia Mendes Lopes, INJC/UFRJ ______________________________________________________ Profª. Lourdes Maria Correa Cabral, EMPBRAPA RIO DE JANEIRO 2018 4 ACKNOLEDGEMENTS Ninguém passa por essa vida sem alguém pra dividir momentos, sorrisos ou choros. Então, se eu cheguei até aqui, foi porque jamais estive sozinha, e não poderia deixar de agradecer aqueles que estiveram comigo, fisicamente ou em pensamento. Primeiramente gostaria de agradecer aos meus pais, Claudia e Ricardo, por tudo. Pelo amor, pela amizade, pela incansável dedicação, pelos valores passados e por todo esforço pra que eu pudesse ter uma boa educação.