DOCSLIB.ORG

Ellagic Acid: Biological Properties and Biotechnological Development for Production Processes

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Ellagic Acid: Biological Properties and Biotechnological Development for Production Processes African Journal of Biotechnology Vol. 10(22), pp. 4518-4523, 30 May, 2011 Available online at http://www.academicjournals.org/AJB DOI: 10.5897/AJB10.2201 ISSN 1684–5315 © 2011 Academic Journals Review Ellagic acid: Biological properties and biotechnological development for production processes Leonardo Sepúlveda1, Alberto Ascacio1, Raúl Rodríguez-Herrera1, Antonio Aguilera-Carbó2 and Cristóbal N. Aguilar1* 1Department of Food Science and Technology, Universidad Autónoma de Coahuila, Saltillo, Coahuila, México. 2Department of Food Science and Nutrition, Universidad Autónoma Agraria Antonio Narro, Buenavista, Saltillo, Coahuila, México. Accepted 15 April, 2011 Ellagic acid, 2,3,7,8-tetrahydroxy-chromeno[5,4,3-cde]chromene-5,10-dione, is a powerful bioactive compound with many potential pharmacological and industrial applications. In this review, the chemical aspects, biological properties and diverse potential applications of ellagic acid for different industries were described. This review also discussed the advance in ellagitannin biodegradation, focusing on the process of isolation of microorganisms and strain selection, medium and culture optimization, as well as fermentation systems for commercially viable industrial scale production. The performances of various fermentation techniques that have been applied for the production of ellagic acid from residual by-products were compared, while the advantages and disadvantages of each plant source were also discussed. Key words: Ellagic acid, ellagitannin, biodegradation, fungal physiology, solid-state fermentation, submerged fermentation. INTRODUCTION Tannins are polyphenolic compounds present in different Also, these bio-active molecules offer protection against plant species, they are water soluble with molecular masses ruminants due to the formation of complexes between ranging form 500 to 20000 Da (Khanbabaee and Ree, plant tannins and animal proteins such as hydroxyproline- 2001). They are distributed in fruits, stalks, peels, roots rich proteins. Formation of such complexes results in a and leaves (Haslam and Cai, 1994). Concentration and bitter and disagreeable sensation which deters potential kinds of these compounds are determined by plant predators. Molecules present in the plants that are specie. Tannins are considered as secondary metabolites susceptible to microbial degradation, such as proteins in plant physiology and are generally classified into four and polysaccharides, have evolved to become highly groups: gallotannins, ellagitannins, condensed tannins resistant to such degradation when linked to tannins and complex tannins (Khanbabae and Ree, 2001). (Aguilera-Carbo et al., 2009). These phytochemicals are located in the vacuoles of One of the most important roles of tannins is the intact plant cells, and are released upon attack by diverse growth inhibition towards many microorganisms including microorganisms, including viruses, bacteria and fungi, bacteria, yeasts and fungi. They are therefore recalcitrant thereby avoiding potential infection of plant tissues. In to enzyme degradation by most microorganisms. addition, the astringent properties of tannins are well Condensed tannins are more resistant to microbial attack known to stop the infestation of insects (Koide et al., than hydrolysable tannins and are more toxic for 1998). foodborne pathogens (Aguilera-Carbo et al., 2005). Tannins retard the decomposition of solid organic material through inhibition of degrading enzymes of attacking microorganisms. When tannins are complexed with microbial proteins or polysaccharides, the interactions *Corresponding author. E-mail: [email protected]. formed are often irreversible and this characteristics mx. Tel: 52 (844) 4161338. Fax: 52 (844) 415 9534. confer on them the bactericide and bacteriostatic proper- Sepúlveda et al. 4519 four phenolic groups and two lactones, which can act as hydrogen-forming sides and electron acceptors, respectively, and represent the hydrophilic domain (Aguilera-Carbó et al., 2005). Ellagic acid is a compound that has generated commercial interest in recent years due to its properties, applications and benefits to human health. BIOLOGICAL PROPERTIES OF ELLAGIC ACID Antioxidants are compound that can delay, inhibit or prevent the oxidation of compounds, trapping free radi- cals and reducing oxidative stress. The presence of ellagic acid in various commercial products giving anti- oxidant activity has also been reported. These molecules have a variety of benefits for their anti-mutagenic, antimicrobial and antioxidant properties, and inhibitors of human immunodeficiency virus (HIV) (Tatsuo et al., 1998; Feldman et al., 1999; Akiyama et al., 2001; Vattem and Shetty, 2003; Ruibal et al., 2003). Ellagic acid prevents Figure 1. Hexaydroxidiphenic group of the formation of various tumors, this mechanism of action ellagitannins. can be possible because compounds such as ellagi- tannins and ellagic acid, explicitly interact with the cells walls or sites with facility to complex proteins, preventing ties. However, some microorganisms tolerate the the proliferation of metastatic cells (Tatsuo et al., 1998). presence of tannins and/or use these com-pounds as Losso et al. (2004) evaluated the potential cytotoxic and carbon source. That ability is generated by the production anti-proliferative activities of ellagic acid in human cells, of a tannin-degrading enzyme or tannase, produced lung, colon, breast and prostate cancer, and showed that mainly by microorganisms of the genus Aspergillus and doses of 1 to 100 mol/L inhibited the proliferation of the Penicillium (Aguilar et al., 2008). cancers mentioned. It has been demonstrated that ellagic Ellagitannins (ETs) correspond to esters of ellagic acid acid acts, possibly causing apoptosis in cancer cells by with glucose or quinic acid. ETs are generated by inhibiting factors that promote metastasis. Huertz et al. oxidative interaction of gallotannins with at least 2 galoyl (2005) studied a coordinated response between a typical units, originating from a group called hexahydroxy- carcinogen such as benzo [] piren-7, 8-diol-epoxide dyphenic acid (HHDP) (Figure 1). This group is released (BPDE) and ellagic acid, which they see as chemopre- after hydrolysis of ETs, and spontaneously lactonized or ventive agent in some cancers caused by polycyclic rearranged to generate the ellagic acid. There are more aromatic hydrocarbons (PAHs). The authors proposed a than 500 ellagitannin structures reported (Feldman et al., mechanism by which ellagic acid, in the formation of 1999). The ellagitannins are mainly derived from the bark DNA, is adducted by the direct compaction of the of oak (Quercus spp.). Bianco et al. (1998) indicated ET's carcinogen. can be can be classified according to the number of Studies of ellagic acid in cancer cells have demon- HHDP groups in the molecule, as monomeric, oligomeric strated the induction of apoptosis or cell death, and polymeric structures (grade of polymerization). The preventing a continuous tumor growth (Ito et al., 1999). principal molecule for the formation or biosynthesis of This mechanism was proposed by Heather et al. (2007) ETs is pentagaloyl glucose (PGG). The oxidation of this when polyphenol-rich raspberry extracts were made and molecule is carried out enzymatically by plant polyphenol fractioned by chromatography on C18 solid phase, oxidase, which performs the coupling of galoyl groups to reporting that one of the separated compounds identified generate the group HHDP (Figure 2). as ellagic showed the ability to inhibit in vitro, the proliferation of human cervical cancer (HeLa) cells, and the possible mechanism explained was that ellagic acid ELLAGIC ACID from ETs induces apoptosis through intrinsic mito- chondrial pathway. Other studies have identified impor- Ellagic acid (Figure 3) is a molecule with a molecular tant ETs-type phytochemicals in diverse berry fruit weight of 302 gmol-1. It is a molecule that is highly extracts, which are characterized by biological properties thermostable (melting point of 350°C) (Ascacio et al., such as anticancer (colon, prostate and leukemia), anti- 2010), and has four rings representing the lipophilic domain, neuodegenarative, anti-viral, etc. (Mertens-Talcott et al., 4520 Afr. J. Biotechnol. Figure 2. Scheme of PGG oxidation (A) and the ellagitannin telimagrandin II (B) by a phenol oxidase type enzyme (Niemetz et al., 2003). aureus strains (Machado et al., 2002). These biological properties have been attributed to the ETs ability to inhibit gyrase activity which is associated with the cleavage of the DNA strand during replication process (Weidner- Wells et al., 1998). It is pointed out that this bacterium does not have the ability to resist this type of antibacterial action. Also, different concentrations of ellagic acid against the human immunodeficiency virus have been tested, and it demonstrated the ability to inhibit the virus growth and spread due to the ability of ellagic acid to attach to HIV proteins (Notka et al., 2004). Also, viruses do not have the ability to replicate themselves in the presence of ETs; because they inhibit the integrase enzyme involved in the insertion of viral genomic material to host cells (Jegede et al., 2008). This is particular in the Figure 3. Structure of ellagic acid. case of retroviruses, including HIV, were these very specific phytochemicals also inhibit reverse transcriptase activity (Aguilera-Carbó et al., 2009). Therefore, there is 2003; Seeram et al., 2006). Atta-Ur-Rahman
Load more

Recommended publications
  • 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]
  • Inhibitory Activities of Selected Sudanese Medicinal Plants On
    Mohieldin et al. BMC Complementary and Alternative Medicine (2017) 17:224 DOI 10.1186/s12906-017-1735-y RESEARCH ARTICLE Open Access Inhibitory activities of selected Sudanese medicinal plants on Porphyromonas gingivalis and matrix metalloproteinase-9 and isolation of bioactive compounds from Combretum hartmannianum (Schweinf) bark Ebtihal Abdalla M. Mohieldin1,2, Ali Mahmoud Muddathir3* and Tohru Mitsunaga2 Abstract Background: Periodontal diseases are one of the major health problems and among the most important preventable global infectious diseases. Porphyromonas gingivalis is an anaerobic Gram-negative bacterium which has been strongly implicated in the etiology of periodontitis. Additionally, matrix metalloproteinases-9 (MMP-9) is an important factor contributing to periodontal tissue destruction by a variety of mechanisms. The purpose of this study was to evaluate the selected Sudanese medicinal plants against P. gingivalis bacteria and their inhibitory activities on MMP-9. Methods: Sixty two methanolic and 50% ethanolic extracts from 24 plants species were tested for antibacterial activity against P. gingivalis using microplate dilution assay method to determine the minimum inhibitory concentration (MIC). The inhibitory activity of seven methanol extracts selected from the 62 extracts against MMP-9 was determined by Colorimetric Drug Discovery Kit. In search of bioactive lead compounds, Combretum hartmannianum bark which was found to be within the most active plant extracts was subjected to various chromatographic (medium pressure liquid chromatography, column chromatography on a Sephadex LH-20, preparative high performance liquid chromatography) and spectroscopic methods (liquid chromatography-mass spectrometry, Nuclear Magnetic Resonance (NMR)) to isolate and characterize flavogalonic acid dilactone and terchebulin as bioactive compounds. Results: About 80% of the crude extracts provided a MIC value ≤4 mg/ml against bacteria.
    [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]
  • 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]
  • In Vivo Anti-Inflammatory and Antioxidant Properties of Ellagitannin
    View metadata, citation and similar papers at core.ac.uk brought to you by CORE provided by Okayama University Scientific Achievement Repository 1 In vivo anti-inflammatory and antioxidant properties of ellagitannin 2 metabolite urolithin A 3 4 5 Hidekazu Ishimotoa, Mari Shibatab, Yuki Myojinc, Hideyuki Itoa,c,*, Yukio Sugimotob, 6 Akihiro Taid, and Tsutomu Hatanoa 7 8 a Department of Pharmacognosy, Division of Pharmaceutical Sciences, Okayama 9 University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, 1-1-1 10 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan 11 b Department of Pharmacology, Division of Pharmaceutical Sciences, Okayama 12 University Graduate School of Medicine, Dentistry and Pharmaceutical Sciences, 1-1-1 13 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan 14 c Department of Pharmacognosy, Faculty of Pharmaceutical Sciences, Okayama 15 University, 1-1-1 Tsushimanaka, Kita-ku, Okayama 700-8530, Japan 16 d Faculty of Life and Environmental Sciences, Prefectural University of Hiroshima, 562 17 Nanatsuka-cho, Shobara, Hiroshima 727-0023, Japan 18 19 20 *Corresponding Author 21 Phone & fax: +81 86 251 7937; e-mail: [email protected] 22 1 23 ABSTRACT 24 Urolithin A is a major metabolite produced by rats and humans after consumption of 25 pomegranate juice or pure ellagitannin geraniin. In this study, we investigated the 26 anti-inflammatory effect of urolithin A on carrageenan-induced paw edema in mice. The 27 volume of paw edema was reduced at 1 h after oral administration of urolithin A. In 28 addition, plasma in treated mice exhibited significant oxygen radical antioxidant 29 capacity (ORAC) scores with high plasma levels of the unconjugated form at 1 h after 30 oral administration of urolithin A.
    [Show full text]
  • Corilagin in Cancer: a Critical Evaluation of Anticancer Activities and Molecular Mechanisms
    molecules Review Corilagin in Cancer: A Critical Evaluation of Anticancer Activities and Molecular Mechanisms Ashutosh Gupta 1 , Amit Kumar Singh 1 , Ramesh Kumar 1, Risha Ganguly 1, Harvesh Kumar Rana 1, Prabhash Kumar Pandey 1 , Gautam Sethi 2, Anupam Bishayee 3,* and Abhay K. Pandey 1,* 1 Department of Biochemistry, University of Allahabad, Allahabad 211 002, Uttar Pradesh, India; [email protected] (A.G.); [email protected] (A.K.S.); [email protected] (R.K.); [email protected] (R.G.); [email protected] (H.K.R.); [email protected] (P.K.P.) 2 Department of Pharmacology, Yong Loo Lin School of Medicine, National University of Singapore, Singapore 117600, Singapore; [email protected] 3 Lake Erie College of Osteopathic Medicine, Bradenton, FL 34211, USA * Correspondence: [email protected] or [email protected] (A.B.); [email protected] or akpandey23@rediffmail.com (A.K.P.); Tel.: +1-941-782-5729 (A.B.); +91-983-952-1138 (A.K.P.) Academic Editor: Gianni Sacchetti Received: 28 August 2019; Accepted: 16 September 2019; Published: 19 September 2019 Abstract: Corilagin (β-1-O-galloyl-3,6-(R)-hexahydroxydiphenoyl-d-glucose), an ellagitannin, is one of the major bioactive compounds present in various plants. Ellagitannins belong to the hydrolyzable tannins, a group of polyphenols. Corilagin shows broad-spectrum biological, and therapeutic activities, such as antioxidant, anti-inflammatory, hepatoprotective, and antitumor actions. Natural compounds possessing antitumor activities have attracted significant attention for treatment of cancer. Corilagin has shown inhibitory activity against the growth of numerous cancer cells by prompting cell cycle arrest at the G2/M phase and augmented apoptosis.
    [Show full text]
  • Berry Phenolics: Isolation, Analysis, Identification, and Antioxidant Properties
    Berry phenolics: isolation, analysis, identification, and antioxidant properties Petri Kylli ACADEMIC DISSERTATION To be presented, with the permission of the Faculty of Agriculture and Forestry of the University of Helsinki, for public criticism in lecture hall B2, Viikki, on August 26th 2011, at 12 o’clock noon. University of Helsinki Department of Food and Environmental Sciences Food Chemistry Helsinki 2011 Custos: Professor Vieno Piironen Department of Food and Environmental Sciences University of Helsinki Helsinki, Finland Supervisor: Professor Marina Heinonen Department of Food and Environmental Sciences University of Helsinki Helsinki, Finland Reviewers: Ph.D. Pirjo Mattila MTT Agrifood Research Finland Jokioinen, Finland Ph.D. Claudine Manach INRA, Nutrition Humaine Saint-Genes-Champanelle, France Opponent: Professor Anne S. Meyer Department of Chemical and Biochemical Engineering Technical University of Denmark Kgs. Lyngby, Denmark ISBN 978-952-10-7114-0 (paperback) ISBN 978-952-10-7115-7 (pdf; http://ethesis.helsinki.fi) ISSN 0355-1180 Cover picture: Tuuli Koivumäki Unigrafia Helsinki 2011 Kylli, P 2011. Berry phenolics: isolation, analysis, identification, and antioxidant properties (dissertation). EKT-series 1502. University of Helsinki. Department of Food and Environmental Sciences. 90+62 pp. ABSTRACT The main objectives in this thesis were to isolate and identify the phenolic compounds in wild (Sorbus aucuparia) and cultivated rowanberries, European cranberries (Vaccinium microcarpon), lingonberries (Vaccinium vitis-idaea), and cloudberries (Rubus chamaemorus), as well as to investigate the antioxidant activity of phenolics occurring in berries in food oxidation models. In addition, the storage stability of cloudberry ellagitannin isolate was studied. In wild and cultivated rowanberries, the main phenolic compounds were chlorogenic acids and neochlorogenic acids with increasing anthocyanin content depending on the crossing partners.
    [Show full text]
  • Phase II Conjugates of Urolithins Isolated from Human Urine and Potential Role of B-Glucuronidases in Their Disposition S
    Supplemental material to this article can be found at: http://dmd.aspetjournals.org/content/suppl/2017/03/10/dmd.117.075200.DC1 1521-009X/45/6/657–665$25.00 https://doi.org/10.1124/dmd.117.075200 DRUG METABOLISM AND DISPOSITION Drug Metab Dispos 45:657–665, June 2017 Copyright ª 2017 by The American Society for Pharmacology and Experimental Therapeutics Phase II Conjugates of Urolithins Isolated from Human Urine and Potential Role of b-Glucuronidases in Their Disposition s Jakub P. Piwowarski, Iwona Stanisławska, Sebastian Granica, Joanna Stefanska, and Anna K. Kiss Department of Pharmacognosy and Molecular Basis of Phytotherapy, Faculty of Pharmacy (J.P.P., I.S., S.G., A.K.K.), and Department of Pharmaceutical Microbiology, Centre for Preclinical Research and Technology (CePT) (J.S.), Medical University of Warsaw, Warsaw, Poland; Primary Laboratory of Origin: Medical University of Warsaw, Faculty of Pharmacy Received January 24, 2017; accepted March 1, 2017 ABSTRACT In recent years, many xenobiotics derived from natural products tissue, and urine. The aim of this study was to isolate and Downloaded from have been shown to undergo extensive metabolism by gut micro- structurally characterize urolithin conjugates from the urine of a biota. Ellagitannins, which are high molecular polyphenols, are volunteer who ingested ellagitannin-rich natural products, and to metabolized to dibenzo[b,d]pyran-6-one derivatives—urolithins. evaluate the potential role of b-glucuronidase–triggered cleavage These compounds, in contrast with their parental compounds, have in urolithin disposition. Glucuronides of urolithin A, iso-urolithin A, good bioavailability and are found in plasma and urine at micromo- and urolithin B were isolated and shown to be cleaved by the lar concentrations.
    [Show full text]
  • Author's Accepted Manuscript
    Author’s Accepted Manuscript Terminalia laxiflora and Terminalia brownii contain a broad spectrum of antimycobacterial compounds including ellagitannins, ellagic acid derivatives, triterpenes, fatty acids and fatty alcohols Enass Y.A. Salih, Riitta Julkunen-Tiitto, Anna- Maija Lampi, Markku Kanninen, Olavi Luukkanen, Marketta Sipi, Mari Lehtonen, Heikki Vuorela, Pia www.elsevier.com/locate/jep Fyhrquist PII: S0378-8741(17)32243-2 DOI: https://doi.org/10.1016/j.jep.2018.04.030 Reference: JEP11325 To appear in: Journal of Ethnopharmacology Received date: 12 June 2017 Revised date: 7 December 2017 Accepted date: 21 April 2018 Cite this article as: Enass Y.A. Salih, Riitta Julkunen-Tiitto, Anna-Maija Lampi, Markku Kanninen, Olavi Luukkanen, Marketta Sipi, Mari Lehtonen, Heikki Vuorela and Pia Fyhrquist, Terminalia laxiflora and Terminalia brownii contain a broad spectrum of antimycobacterial compounds including ellagitannins, ellagic acid derivatives, triterpenes, fatty acids and fatty alcohols, Journal of Ethnopharmacology, https://doi.org/10.1016/j.jep.2018.04.030 This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting galley proof before it is published in its final citable form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. Terminalia laxiflora and Terminalia brownii contain a broad spectrum of antimycobacterial compounds including ellagitannins, ellagic acid derivatives, triterpenes, fatty acids and fatty alcohols Enass Y.A.
    [Show full text]
  • Microbial Metabolite Urolithin B Inhibits Recombinant Human Monoamine Oxidase a Enzyme
    H OH metabolites OH Communication Microbial Metabolite Urolithin B Inhibits Recombinant Human Monoamine Oxidase A Enzyme Rajbir Singh 1 , Sandeep Chandrashekharappa 2 , Praveen Kumar Vemula 2, Bodduluri Haribabu 1 and Venkatakrishna Rao Jala 1,* 1 Department of Microbiology and Immunology, James Graham Brown Cancer Center, University of Louisville, Louisville, KY 40202, USA; [email protected] (R.S.); [email protected] (B.H.) 2 Institute for Stem Cell Science and Regenerative Medicine (inStem), University of Agricultural Sciences-Gandhi Krishi Vignan Kendra (UAS-GKVK) Campus, Bellary Road, Bangalore, Karnataka 560065, India; [email protected] (S.C.); [email protected] (P.K.V.) * Correspondence: [email protected] Received: 7 May 2020; Accepted: 17 June 2020; Published: 19 June 2020 Abstract: Urolithins are gut microbial metabolites derived from ellagitannins (ET) and ellagic acid (EA), and shown to exhibit anticancer, anti-inflammatory, anti-microbial, anti-glycative and anti-oxidant activities. Similarly, the parent molecules, ET and EA are reported for their neuroprotection and antidepressant activities. Due to the poor bioavailability of ET and EA, the in vivo functional activities cannot be attributed exclusively to these compounds. Elevated monoamine oxidase (MAO) activities are responsible for the inactivation of monoamine neurotransmitters in neurological disorders, such as depression and Parkinson’s disease. In this study, we examined the inhibitory effects of urolithins (A, B and C) and EA on MAO activity using recombinant human MAO-A and MAO-B enzymes. Urolithin B was found to be a better MAO-A enzyme inhibitor among the tested urolithins and EA with an IC50 value of 0.88 µM, and displaying a mixed mode of inhibition.
    [Show full text]
  • Profile of Bioactive Compounds in Nymphaea Alba L. Leaves Growing
    Bakr et al. BMC Complementary and Alternative Medicine (2017) 17:52 DOI 10.1186/s12906-017-1561-2 RESEARCH ARTICLE Open Access Profile of bioactive compounds in Nymphaea alba L. leaves growing in Egypt: hepatoprotective, antioxidant and anti-inflammatory activity Riham Omar Bakr1*, Mona Mohamed El-Naa2, Soumaya Saad Zaghloul1 and Mahmoud Mohamed Omar3,4 Abstract Background: Nymphaea alba L. represents an interesting field of study. Flowers have antioxidant and hepatoprotective effects, rhizomes constituents showed cytotoxic activity against liver cell carcinoma, while several Nymphaea species have been reported for their hepatoprotective effects. Leaves of N. alba have not been studied before. Therefore, in this study, in-depth characterization of the leaf phytoconstituents as well as its antioxidant and hepatoprotective activities have been performed where N. alba leaf extract was evaluated as a possible therapeutic alternative in hepatic disorders. Methods: The aqueous ethanolic extract (AEE, 70%) was investigated for its polyphenolic content identified by high-resolution electrospray ionisation mass spectrometry (HRESI-MS/MS), while the petroleum ether fraction was saponified, and the lipid profile was analysed using gas liquid chromatography (GLC) analysis and compared with reference standards. The hepatoprotective activity of two doses of the extract (100 and 200 mg/kg; P.O.) for 5 days was evaluated against CCl4-induced hepatotoxicity in male Wistar albino rats, incomparisonwithsilymarin.Liverfunctiontests; aspartate aminotransferase (AST), alanine aminotransferase (ALT), alkaline phosphatase (ALP), gamma glutamyl transpeptidase (GGT) and total bilirubin were performed. Oxidative stress parameters; malondialdehyde (MDA), reduced glutathione (GSH), catalase (CAT), superoxide dismutase (SOD), total antioxidant capacity (TAC) as well as inflammatory mediator; tumour necrosis factor (TNF)-α were detected in the liver homogenate.
    [Show full text]
  • Traditional Applications of Tannin Rich Extracts Supported by Scientific Data: Chemical Composition, Bioavailability and Bioaccessibility
    foods Review Traditional Applications of Tannin Rich Extracts Supported by Scientific Data: Chemical Composition, Bioavailability and Bioaccessibility Maria Fraga-Corral 1,2 , Paz Otero 1,3 , Lucia Cassani 1,4 , Javier Echave 1 , Paula Garcia-Oliveira 1,2 , Maria Carpena 1 , Franklin Chamorro 1, Catarina Lourenço-Lopes 1, Miguel A. Prieto 1,* and Jesus Simal-Gandara 1,* 1 Nutrition and Bromatology Group, Analytical and Food Chemistry Department, Faculty of Food Science and Technology, Ourense Campus, University of Vigo, 32004 Ourense, Spain; [email protected] (M.F.-C.); [email protected] (P.O.); [email protected] (L.C.); [email protected] (J.E.); [email protected] (P.G.-O.); [email protected] (M.C.); [email protected] (F.C.); [email protected] (C.L.-L.) 2 Centro de Investigação de Montanha (CIMO), Campus de Santa Apolonia, Instituto Politécnico de Bragança, 5300-253 Bragança, Portugal 3 Department of Pharmacology, Pharmacy and Pharmaceutical Technology, Faculty of Veterinary, University of Santiago of Compostela, 27002 Lugo, Spain 4 Research Group of Food Engineering, Faculty of Engineering, National University of Mar del Plata, Mar del Plata RA7600, Argentina * Correspondence: [email protected] (M.A.P.); [email protected] (J.S.-G.) Abstract: Tannins are polyphenolic compounds historically utilized in textile and adhesive industries, Citation: Fraga-Corral, M.; Otero, P.; but also in traditional human and animal medicines or foodstuffs. Since 20th-century, advances in Cassani, L.; Echave, J.; analytical chemistry have allowed disclosure of the chemical nature of these molecules. The chemical Garcia-Oliveira, P.; Carpena, M.; profile of extracts obtained from previously selected species was investigated to try to establish a Chamorro, F.; Lourenço-Lopes, C.; bridge between traditional background and scientific data.
    [Show full text]