DOCSLIB.ORG

Bioactive Constituents and Medicinal Importance of Genus Alnus

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Bioactive Constituents and Medicinal Importance of Genus Alnus PHCOG REV. REVIEW ARTICLE Bioactive constituents and medicinal importance of genus Alnus Sushil Chandra Sati, Nitin Sati1, O. P. Sati, Department of Chemistry, 1Pharmaceutical Sciences, H.N.B. Garhwal University, Srinagar Garhwal, Uttarakhand, India Submitted: 19-08-2010 Revised: 22-02-2011 Published: 23-12-2011 ABSTRACT The genus Alnus has been reviewed for its chemical constituents and biological activities including traditional importance of some common species. The plants of this genus contain terpenoids, fl avonoids, diarylheptanoids, phenols, steroids, and tannins. Diarylheptanoids are the dominant constituents within the genus Alnus, few of them exhibited antioxidant effects and inhibitory activity against nuclear factor kappaB activation, nitric oxide and tumor necrosis factor-α production, human umbilical vein endothelial cells, farnesyl protein transferase, cell-mediated low-density lipoprotein oxidation, HIF-1 in AGS cells, and the HIV-1-induced cytopathic effect in MT-4 cells. Some ellagitannines showed hepatoprotective activity even in a dose of 1 mg/kg which is ten-fold smaller compared with the dose of traditional fl avonoid-based drugs. The members of genus Alnus are well known for their traditional uses in the treatment of various diseases like cancer, hepatitis, infl ammation of uterus, uterine cancer, rheumatism, dysentery, stomachache, diarrhea, fever, etc. The aim of the present review is to summarize the various researches related to the chemistry and pharmacology of genus Alnus. Key words: Alnus, antioxidant effects, diarylheptanoids, HIV-I, inhibitory activity INTRODUCTION The plants of this genus have been found active against many live-threatening disorders like hepatitis, HIV-1 viral replication, Betulaceae or the Birch family includes six genera of deciduous and cancer. The aim of the present review is to delineate the nut-bearing trees and shrubs, including the birches, alders, hazels, various plants with their chemical constituents and biological hornbeams, and hop-hornbeams, numbering about 130 species. activities. Various traditional uses of some common species These are mostly natives of the temperate Northern Hemisphere, have also been summarized. These informations can create with a few species reaching the Southern Hemisphere in the a center of attention for scientists and herbologists for this Andes in South America. Alnus (alders) is an important genus genus, and consequently this database might play a major role belonging to Betulaceae which comprises 30 species worldwide. in future research. [1,2] Almost all plants of this genus have been traditionally used as folk medicine in Ayurveda, Unani, and Chinese medical systems. TRADITIONAL USES OF ALNUS SPECIES OBJECTIVES OF THE REVIEW The members of genus Alnus are well known for their traditional medicinal values. These have been used for the Alnus is one of the genera having potential medicinal values. treatment of various diseases including cancer and as an Address for correspondence: alterative, astringent, cathartic, emetic, febrifuge, galactogogue, Dr. Sushil Chandra Sati, hemostatic, parasiticide, skin tonic, vermifuge, etc. Alnus japonica Department of Chemistry, H.N.B. Garhwal University, is a popular folk medicine in Korea for cancer and hepatitis.[3] Srinagar Garhwal, Uttarakhand, India. E-mail: [email protected] The bark of Alnus glutinosa is alterative, astringent, cathartic, febrifuge, tonic, and useful in mouth and throat infl ammations, Access this article online the vinegar extract of inner bark of plant produces a useful Quick Response Code: wash to treat lice and a range of skin problems such as scabies Website: and scabs.[4-6] The leaf, roots, and bark of A. nepalensis are used www.phcogrev.com in dysentery, stomach ache, and diarrhea in Indian system of medicine (Ayurveda).[7] A decoction of the root of A. DOI: nepalensis is prescribed to treat diarrhea and paste from the 10.4103/0973-7847.91115 leaves is applied on cuts and wounds as a hemostatic.[8] The mixture of leaves of Alnus jorullensis and branches of Polylepis 174 Pharmacognosy Reviews | July-December 2011 | Vol 5 | Issue 10 Sati, et al.: Bioactive constituent and medicinal importance of genus Alnus racemosa R. et P is used to treat infl ammation of uterus, uterine dien-3-oic acid (14); (23E)-(20S)-20,25,26-trihydroxy-3,4- cancer, and rheumatism.[9] The bark of Alnus hirsuta is used in secodammara-4(28),23-dien-3-oic acid (15); (23E)-(12R,20S)- Korean and Chinese traditional medicine as remedies for fever, 12,20,25-trihydroxy-3,4-secodammara-4(28),23-dien-3-oic acid hemorrhage, alcoholism, and diarrhea.[10,11] The decoction of (16); hirsutanonol 5-O-(6-O-galloyl)-β-D-glucopyranoside A. glutinosa barks is used to treat swelling, infl ammation, and (17); 3-deoxo-hisutanonol 5-O-β-D-gucopyranoside (18); rheumatism. [12] It has also been used as an astringent, bitter, hirsutanonol (19); hirsutanonol 5-O-β-D-glucopyranoside emetic, and hemostatic, and for the treatment of sore throat (20); 3-deoxo-hisutanonol 5-O-(6-O- β-D-apiosyl)- β-D- and pharyngitis.[13,14] Contemporary indigenous healers used the glucopyranoside (21); hirsutenone (22); 7-(3,4-dihydroxyphenyl)- bark of Alnus rubra for various medicinal teas.[15,16] 5-hydroxy-1-(4-hydroxyphenyl)-3-heptanone-5-O-β–D- xylopyranoside (23); 1-(3,4-dihydroxyphenyl)-5-hydroxy-7- CHEMICAL CONSTITUENTS OF GENUS ALNUS (4-hydroxyphenyl)-3-heptanone-5-O-β–D-xylopyranoside (24); 1,7-bis-(3,4-dihydroxyphenyl)-5-hydroxy-3-heptanone- The plants of the genus Alnus contain various types of 5-O-[2-(2-methylbutenoyl)]-β–D-xylopyranoside (25); plant secondary metabolites including terpenoids, fl avonoids, 1,7-bis-(3,4-dihydroxyphenyl)-5-methoxy-3-heptanone (26); diarylheptanoids, phenols, steroids, tannins, and many others. The oregonin (27); β-amyrin (28); 3-O-acetyl- β-amyrin (29); plants and their chemical constituents have been summarized below, 3-O-acetyltaraxerol (30); glutinone (31), lupenone (32); quercitin whereas the chemical structures of various compounds isolated (33); 5-O-methylhirsutanonol (34); glutinol (35); taraxerone (36); alnusjaponins A (37); alnusjaponins B (38); 5-O-galloyl-( )- from different parts of genus Alnus are drawn in Figures 1 to 8. ‾ shikimic acid (39); 2,3-(S)-hexahydroxydiphenoyl-D-glucose Chemical constituents of Alnus japonica (40); 4,6-di-O-galloyl-D-glucose (41); 1,4-di-O-galloyl- β Luteolin 7,4’-dimethyl ether (pillion) (1); scutellarein-6,7,4’- -D-glucose (42); 4,6-(S)-valoneoyl-D-glucose (43); strictinin trimethyl ether (salvigenin) (2); kaempferide (3); isohamnetin (44); gemin D (45); pedunculagin (46); praecoxin A (47); (4); rhamnazin (5); quercetin-7,3’,4’-trimethyl ether (6); the fl osin A (48); stachyurin (49); casuarinin (50); 1,7-bis-(3,4- 3,6,4’-trimethyl ether of 6-hydroxy-kaempferol (7); acacetin dihydroxyphenyl)-heptane-3-O-β-D-glucopyranosyl(1→3)- (8); apigenin-7,4’-dimethyl ether (9); scutellarein-6,4’-dimethyl β-D-xylopyranoside (51); 1,7-bis-(3,4-dihydroxyphenyl)- ether (10); methyl (24E)-3,4-secodammara-4(28),20,24- heptane-3-O-β-D-apiofuranosyl(1→6)-β-D-glucopyranoside trien-26-oic acid-3-oate (11); (24E)-3,4-secodammara- (52); 1,7-bis-(3,4-dihydroxyphenyl)-heptane-5-O-β-D- 4(28),20,24-trien-3,26-dioic acid (12); (20S,24S)-20,24- glucopyranoside (53); 1,7-bis-(3,4-dihydroxyphenyl)-5- dihydroxy-3,4-secodammara-4(28),23-dien-3-oic acid (13); hydroxyheptane (54); 1,7-bis-(3,4-dihydroxyphenyl)-heptane- (23E)-(20S)-20,25-dihydroxy-3,4-secodammara-4(28),23- 3-one-5-O-β-D-glucopyranoside (55); platyphylloside (56); 26 24 21 R2 R3 R 21 CO R 1 R2 R 2 2 O OR 3 HO 26 2' 1' 2 2" OH 20 25 24 19 OH OH , 20 25 R1 R3 12 , 1 3 7 1" H xyl OH 27 12 23 27 24 OH xyl H 3 4' 4" 1 3 R1O2C 1 6" 25 OH R* OH R1O2C HO 2 OH R* = xyl -CO-CHCH3 11 R1 =Me, R2 = H 5" 26 OH CH3 OH 12 R = R = H 29 4 1 2 29 CH2CH3 55 OH glc OH 4 13 R1 = R2 = H, R3= OH H xyl H 153 28 28 R1 R2 R R R5OH2C 3 4 R5 O R4O 21 40 H (S)HHDP HH R3O OR1 24 26 HO CH R OR2 23 2 4 H H G COOH 41 H G R R3 20 2 OH O C C O 42 G HHG H 12 27 3 1 HO OH R1O2C 44 G HH(S)HHDP GO OH 14 R1 = R2 = R3= R4 = H 45 H H G (S)HHDP HO OH HO OH 29 4 15 R1 = R2 = R3= H, R4 = OH OH HO (S)HHDP 16 R1 = R3 = R4 = H, R2 = OH 46 H (S)HHDP (S)HHDP 39 28 28 OH 5' 5" OH HO HO 6' 6" 4" 4' 17 R = 6-O-galloyl--D-glucopyranosyl 2 4 6 20 R = -D-glucopyranosyl HO COOH 3' 1' 1 3 5 7 1" 3" OH HO O 2' 2" O H OH OR HO 5' 5" HO OH O HO O 6' 6" 4" 4' C C OCH2 21 R = 6-O-aplosyl- -D-glucopyranosyl HO HO O O 2 4 6 18 R = -D-glucopyranosyl O CH2 HO 1 3 5 7 C O HO 3' 1' 1" 3" OH HO O OH 2' O 2" O O O C O H O OH OR C O C O O HO O C O HO C O 2' 1' 2" OH OH HOOC R1 R R R 1 3 7 1" 2 1 2 22 OH OH HO OH HO OH H 88 H OH 4' 4" OMe 77 H HO OH HO OH HO OH HO 6" OH HO HO OH 5" 48 47 Figure 1: Chemical structures of compounds isolated from genus Alnus Figure 2: Chemical structures of compounds isolated from genus Alnus Pharmacognosy Reviews | July-December 2011 | Vol 5 | Issue 10 175 Sati, et al.: Bioactive constituent and medicinal importance of genus Alnus OH O H OH OH HO OH O OH OH 5 6' 1' 1 3 9 5 6' 1' 1 3 OH HO 5 R1 5' 2' 6 5' 2' R 6 2 C=O 3' 5" 6" 5" 6" 1 OH HO COOH 3' C 4' 4' O 7 OH O O 1" 1" 7 H3CO O HO O 4" 4" HO O HO O H HO 14 2" 2" H O O 3" 3" O H CO H CO 3 OH 3 79 OH 57 C OCH2 78 HO C H OG HO O HO C O CH2 HO C O HO OH O O OH 29 30 O 49 R1 = OH, R2 = H HO 50 R1 = H, R2 = OH HO 43 21 5 OH OH 25 27 19 9 26 R 1 22 OH 16 10 15 25 26 HO 28 7 27 O OH 3 16 1 6 1 C HO OH HO 10 15 O HO O 7 CH2 O 23 24 6 73 R = OCOCH3 14 O C HO OH 75 R = CH2OH 74 R = OH C O O 76 R = COOH R O HO OH 23 24 58
Load more

Recommended publications
  • Walnut Polyphenol
    ORYZA OIL & FAT CHEMICAL CO., L TD. 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 & Cosmetic Grade） ORYZA OIL & FAT CHEMICAL CO., LTD ver. 1.0 HS WALNUT 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.
    [Show full text]
  • 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).
    [Show full text]
  • 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.
    [Show full text]
  • 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.
    [Show full text]
  • 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].
    [Show full text]
  • "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.
    [Show full text]
  • 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.
    [Show full text]
  • 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.
    [Show full text]
  • 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.
    [Show full text]
  • Le Bioraffinage De Myrrhis Odorata, Tussilago Farfara Et Calamintha Grandiflora Pour La Production D'aromes Et D'antioxydants
    En vue de l'obtention du DOCTORAT DE L'UNIVERSITÉ DE TOULOUSE Délivré par : Institut National Polytechnique de Toulouse (INP Toulouse) Discipline ou spécialité : Sciences des Agroressources Présentée et soutenue par : Mme DIANA DOBRAVALSKYTE le lundi 25 novembre 2013 Titre : LE BIORAFFINAGE DE MYRRHIS ODORATA, TUSSILAGO FARFARA ET CALAMINTHA GRANDIFLORA POUR LA PRODUCTION D'AROMES ET D'ANTIOXYDANTS. Ecole doctorale : Sciences de la Matière (SM) Unité de recherche : Laboratoire de Chimie Agro-Industrielle (L.C.A.) Directeur(s) de Thèse : M. THIERRY TALOU M. RIMANTAS VENSKUTONIS Rapporteurs : Mme CHANTAL MENUT, UNIVERSITE MONTPELLIER 2 Mme JOLANTA LIESIENE, UNIVERSITE DE TECHNOLOGIE DE KAUNAS Membre(s) du jury : 1 M. ZIGMUNTAS BERESNEVICIUS, UNIVERSITE DE TECHNOLOGIE DE KAUNAS, Président 2 M. ALGIRDAS ZEMAITAITIS, UNIVERSITE DE TECHNOLOGIE DE KAUNAS, Membre 2 Mme GRAZINA JUODEIKIENÉ, UNIVERSITE DE TECHNOLOGIE DE KAUNAS, Membre 2 Mme ISABELLE FOURASTE, UNIVERSITE TOULOUSE 3, Membre 2 Mme RUTA GALABURDA, LATVIA UNIVERSITY OF AGRICULTURE JELGAVA, Membre 2 M. RIMANTAS VENSKUTONIS, UNIVERSITE DE TECHNOLOGIE DE KAUNAS, Membre REMERCIEMENTS Tout d’abord j’adresse mes remerciements aux différents organismes qui ont mis les moyens financiers pour l’aboutissement de cette thèse: aux gouvernements de la Lituanie et la France, ainsi que Campus France avec la bourse d'Excellence Égide Eiffel. Je remercie les Professeurs Dr. Jolanta LIESIENĖ et Dr. Chantal MENUT pour m'avoir fait l'honneur d'être les rapporteurs de ma thèse. Je remercie également les professeurs Dr. Algirdas ŽEMAITAITIS, Dr. Gražina JUODEIKIENĖ, Dr. Zigmuntas Jonas BERESNEVIČIUS, Dr. Isabelle FOURASTÉ, Dr. Audrius Sigitas MARUŠKA et Dr. Ruta GALOBURDA d’avoir participés en tant qu’examinateurs.
    [Show full text]
  • Phenol Biological Metabolites As Food Intake Biomarkers, a Pending Signature for a Complete Understanding of the Beneficial Effe
    nutrients Review Phenol Biological Metabolites as Food Intake Biomarkers, a Pending Signature for a Complete Understanding of the Beneficial Effects of the Mediterranean Diet Juana I. Mosele 1,2 and Maria-Jose Motilva 3,* 1 Cátedra de Fisicoquímica, Departamento de Química Analítica y Fisicoquímica, Facultad de Farmacia y Bioquímica, Universidad de Buenos Aires, Buenos Aires C1113AAD, Argentina; [email protected] 2 CONICET-Universidad de Buenos Aires, Instituto de Bioquímica y Medicina Molecular (IBIMOL), Buenos Aires C1113AAD, Argentina 3 Instituto de Ciencias de La Vid y del Vino (ICVV), Consejo Superior de Investigaciones Científicas (CSIC), Gobierno de La Rioja, Universidad de La Rioja, 26007 Logroño, Spain * Correspondence: [email protected] Abstract: The Mediterranean diet (MD) has become a dietary pattern of reference due to its preventive effects against chronic diseases, especially relevant in cardiovascular diseases (CVD). Establishing an objective tool to determine the degree of adherence to the MD is a pending task and deserves consideration. The central axis that distinguishes the MD from other dietary patterns is the choice and modality of food consumption. Identification of intake biomarkers of commonly consumed foods is a key strategy for estimating the degree of adherence to the MD and understanding the protective mechanisms that lead to a positive impact on health. Throughout this review we propose potential candidates to be validated as MD adherence biomarkers, with particular focus on the metabolites derived from the phenolic compounds that are associated with the consumption of Citation: Mosele, J.I.; Motilva, M.-J. typical Mediterranean plant foods. Certain phenolic metabolites are good indicators of the intake Phenol Biological Metabolites as Food of specific foods, but others denote the intake of a wide-range of foods.
    [Show full text]
  • Ellagitannins in Cancer Chemoprevention and Therapy
    toxins Review Ellagitannins in Cancer Chemoprevention and Therapy Tariq Ismail 1, Cinzia Calcabrini 2,3, Anna Rita Diaz 2, Carmela Fimognari 3, Eleonora Turrini 3, Elena Catanzaro 3, Saeed Akhtar 1 and Piero Sestili 2,* 1 Institute of Food Science & Nutrition, Faculty of Agricultural Sciences and Technology, Bahauddin Zakariya University, Bosan Road, Multan 60800, Punjab, Pakistan; [email protected] (T.I.); [email protected] (S.A.) 2 Department of Biomolecular Sciences, University of Urbino Carlo Bo, Via I Maggetti 26, 61029 Urbino (PU), Italy; [email protected] 3 Department for Life Quality Studies, Alma Mater Studiorum-University of Bologna, Corso d'Augusto 237, 47921 Rimini (RN), Italy; [email protected] (C.C.); carmela.fi[email protected] (C.F.); [email protected] (E.T.); [email protected] (E.C.) * Correspondence: [email protected]; Tel.: +39-(0)-722-303-414 Academic Editor: Jia-You Fang Received: 31 March 2016; Accepted: 9 May 2016; Published: 13 May 2016 Abstract: It is universally accepted that diets rich in fruit and vegetables lead to reduction in the risk of common forms of cancer and are useful in cancer prevention. Indeed edible vegetables and fruits contain a wide variety of phytochemicals with proven antioxidant, anti-carcinogenic, and chemopreventive activity; moreover, some of these phytochemicals also display direct antiproliferative activity towards tumor cells, with the additional advantage of high tolerability and low toxicity. The most important dietary phytochemicals are isothiocyanates, ellagitannins (ET), polyphenols, indoles, flavonoids, retinoids, tocopherols. Among this very wide panel of compounds, ET represent an important class of phytochemicals which are being increasingly investigated for their chemopreventive and anticancer activities.
    [Show full text]