DOCSLIB.ORG

Resveratrol 98% Natural (Japanese Knotweed)

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Resveratrol 98% Natural (Japanese Knotweed) Resveratrol 98% Natural (Japanese Knotweed) Cambridge Commodities Chemwatch Hazard Alert Code: 3 Part Number: P33926 Issue Date: 04/03/2019 Version No: 1.1.23.11 Print Date: 29/09/2021 Safety data sheet according to REACH Regulation (EC) No 1907/2006, as amended by UK REACH Regulations SI 2019/758 S.REACH.GB.EN SECTION 1 Identification of the substance / mixture and of the company / undertaking 1.1. Product Identifier Product name Resveratrol 98% Natural (Japanese Knotweed) Chemical Name resveratrol Synonyms Not Available Chemical formula Not Applicable Other means of P33926 identification 1.2. Relevant identified uses of the substance or mixture and uses advised against The pharmacological activities and mechanisms of action of natural phenylpropanoid glycosides (PPGs) extracted from a variety of plants such as antitumor, antivirus, anti-inflammation, antibacteria, antiartherosclerosis, anti-platelet-aggregation, antihypertension, antifatigue, analgesia, hepatoprotection, immunosuppression, protection of sex and learning behavior, protection of neurodegeneration, reverse transformation of tumor cells, inhibition of telomerase and shortening telomere length in tumor cells, effects on enzymes and cytokines, antioxidation, free radical scavenging and fast repair of oxidative damaged DNA, have been reported in the literature. Phenylpropanoids (PPs) belong to the largest group of secondary metabolites produced by plants, mainly, in response to biotic or abiotic stresses such as infections, wounding, UV irradiation, exposure to ozone, pollutants, and other hostile environmental conditions. It is thought that the molecular basis for the protective action of phenylpropanoids in plants is their antioxidant and free radical scavenging properties. These numerous phenolic compounds are major biologically active components of human diet, spices, aromas, wines, beer, essential oils,propolis, and traditional medicine. Phenylpropanoids are ingredients of essential oils including those derived from anis, cinnamon bark, and clove They are often used for fragrances and aromatherapy. Significant correlation (54-86%) between antiplatelet potency and PPs content in the Relevant identified uses oils was found, the key role for this moiety in the control of haemostasis was suggested. As a confirmation of the importance of PP moieties in defining this kind of biological activity, traditional Chinese medicine preparations, identified as remedies to prevent blood stasis and thrombus formation were analyzed for their structure/effect relationships. The PPs isoeugenol, ferulic acid, elemicin, myristicin, ethyl gallate, and dihydroxyacetophenone were recognized as essential platelet protecting compounds. Many of these substances share both the shikimic acid biosynthetic pathway and a common PP backbone. It is thought that some beneficial health effects of PPs such as reducing the risk of cancer,osteoporosis and cardiovascular diseases may depend on their action as estrogen agonists/antagonists via estrogen receptors Estrogen receptor, a nuclear steroid receptor, binds estrogens and regulates the transcription of estrogen-responsive genes by interacting directly with DNA at estrogen response elements (ERE) of their promoters. PPs may act as nonsteroidal anti-inflammatory drug (NSAID)-like compounds. The COX-2 gene expression was dramatically inhibited by the synthesized dimer of ferulic acid. Phenylpropanoid glycosides (aka phenylethanoid glycosides, PPGs) originate from the shikimic acid-phenylpropanoid pathway and include simple monosaccharides,consisting of hydroxycinnamic acid and hydroxyphenylethyl (methoxyphenol) moieties Product code: P33926 Version No: 1.1.23.2 Page 1 of 20 S.REACH.GB.EN Lancaster Way Business Park Safety Data Sheet (Conforms to Regulation (EU) No 2020/878) Ely, Cambridgeshire, CB6 3NX, UK. Chemwatch: 9-638011 +44 (0) 1353 667258 Issue Date: 04/03/2019 [email protected] Print Date: 29/09/2021 www.c-c-l.com bonded to a central beta-glucopyranose by ester and glycosidic linkages, respectively,and more complex di-and trisaccharides with one or two additional sugars linked to the core glucose. Members of this compound class have shown a wide range of biological activity,including inhibition of plant pathogenic bacteria and fungi, antioxidant activity, tumour cell suppression, feeding stimulation of specialist herbivores and deterrence of generalist insects. Plant-derived PPGs were found to be effective in the selective inhibition of both tyrosinase activity and melanin synthesis in cultivated melanocytes without cytotoxic effects. The PPGs with antioxidant activities, such as acteoside and martynoside, exhibited antiproliferative, cytotoxic, antimetastatic and immunomodulatory properties Phenylpropanoids fulfill numerous physiological functions, essential for plant growth and development, as well as plant– environment interactions. The phenylpropanoid pathway is one of the most frequently investigated metabolic routes, among secondary metabolite. Phenylpropanoid metabolism generates an enormous array of secondary metabolites, based on the few intermediates of the shikimate pathway). The shikimate pathway is a source of phenylalanine and the entry point leading to the biosynthesis of phenylpropanoids. The so-called central phenylpropanoid pathway is defined by three enzymatic activities: (i) the phenylalanine deamination by phenylalanine ammonia-lyase (PAL) to the trans-cinnamic acid, (ii) the trans-cinnamic acid hydroxylation to the 4-coumarate, as a resulting from cinnamic acid 4-hydroxylase (C4H) activity, and finally (iii) the 4-coumarate conversion to the 4-coumaroyl-CoA by 4-coumarate-CoA ligase (4CL). The cooperating enzymes from the phenylpropanoid pathway were proposed to be organized into complexes called metabolons. The term “metabolon” encompasses multienzymatic complexes bound to the cellular structural elements – membranes. Most metabolon models are based on a dynamic, non-covalent aggregation of components on the endoplasmic reticulum (ER) surface. Organization of enzymes in metabolons is, at the cellular level, a way to optimize biosynthesis. It provides: (i) direct transport of intermediates between successive enzymes, hence increasing local concentration of the substrate around the enzyme active center, (ii) minimization of highly biologically active and potentially toxic intermediates within the cell, as well as (iii) coordination of reactions leading to different branches of pathways with shared enzymes or intermediates. In the phenylpropanoid pathway, intracellular interactions between biosynthetic enzymes were shown for the central phenylpropanoid pathway – where PAL and C4H colocalize in the ER. as well as for particular branches leading to the formation of (iso)flavonoids, monolignols, and anthocyanins. Stilbenoids are a group of naturally occurring phenolic compounds found in various plant species. Stilbenoids exert various biological activities ranging from cardioprotection, neuroprotection, anti-diabetic properties, depigmentation, anti-inflammation, cancer prevention and treatment. Stilbenoids are classified as phytoalexins, which are antimicrobial compounds produced de novo in plants to protect against fungal infection and toxins Although positive results were obtained in most cell culture and animal studies, further human studies are needed to substantiate beneficial effects of stilbenoids. Stilbenoids can be produced by bacteria stilbenoids and in various plants. They are, for example, secondary products of heartwood formation in trees that can act as phytoalexins (antimicrobial and often antioxidative substances). The stilbenoids, resveratrol and pterostilbene thought to exert anticancer effects, target genes with oncogenic function for de novo methylation and silencing, leading to inactivation of related signaling pathways (epigenetic regulation of oncogenic signals) Oligostilbenoids, typically stilbene dimers,trimers, tetramers, hexamers, heptamers and octamers (with various molecular frameworks resulting from different oxidative condensation of resveratrol monomer). show interesting biological activities, such as antibacterial, antiviral, and cytotoxic effects. The phenolic content in wine refers to the phenolic compounds—natural phenol and polyphenols—in wine, which include a large group of several hundred chemical compounds that affect the taste, colour and mouthfeel of wine. These compounds include phenolic acids, stilbenoids, flavonols, dihydroflavonols, anthocyanins, flavanol monomers (catechins) and flavanol polymers (proanthocyanidins). This large group of natural phenols can be broadly separated into two categories, flavonoids and non-flavonoids. Flavonoids include the anthocyanins and tannins which contribute to the color and mouthfeel of the wine. The non-flavonoids include the stilbenoids such as resveratrol and phenolic acids such as benzoic, caffeic and cinnamic acids. Resveratrol is found in highest concentration in the skins of wine grapes. Both red and white wine grape varieties contain resveratrol, but more frequent skin contact and maceration leads to red wines normally having ten times more resveratrol than white wines. Resveratrol and its derivatives produced by grape vines provides defense against microbes, and production can be further artificially stimulated by ultraviolet radiation. Uses advised against Not Applicable 1.3. Details of the supplier of the safety data sheet Registered company name Cambridge Commodities Address Lancaster Way Business Park, Ely, Cambridgeshire
Load more

Recommended publications
  • Synthesis of Vitisin a & D: Thermal Isomerization Enabled by a Persistent Radical Equilibrium
    doi.org/10.26434/chemrxiv.10294826.v1 Synthesis of Vitisin A & D: Thermal Isomerization Enabled by a Persistent Radical Equilibrium Kevin Romero, Mitchell Keylor, Markus Griesser, Xu Zhu, Ethan Strobel, Derek Pratt, Corey Stephenson Submitted date: 12/11/2019 • Posted date: 22/11/2019 Licence: CC BY-NC-ND 4.0 Citation information: Romero, Kevin; Keylor, Mitchell; Griesser, Markus; Zhu, Xu; Strobel, Ethan; Pratt, Derek; et al. (2019): Synthesis of Vitisin A & D: Thermal Isomerization Enabled by a Persistent Radical Equilibrium. ChemRxiv. Preprint. https://doi.org/10.26434/chemrxiv.10294826.v1 The total synthesis of oligomer natural products derived from resveratrol has been achieved through a putative biogenetic bond migration from a presumed common intermediate in a divergent biosynthetic pathway. File list (2) Stephenson_manuscript.pdf (820.13 KiB) view on ChemRxiv download file Stephenson_manuscript.docx (416.19 KiB) view on ChemRxiv download file Synthesis of vitisin A & D: Thermal isomerization enabled by a persistent radical equilibrium Kevin J. Romero,1 Mitchell H. Keylor,1 Markus Griesser,2 Xu Zhu,1 Ethan J. Strobel,1 Derek A. Pratt2,* and Corey R. J. Stephenson1,* 1Department of Chemistry, University of Michigan, 930 North University Avenue, Ann Arbor, Michigan 48109, USA 2Department of Chemistry and Biomolecular Sciences, University of Ottawa, Ottawa, Ontario, Canada K1N 6N5 E-mail: [email protected] Abstract: The first total synthesis of the resveratrol tetramers vitisin A and vitisin D is reported. Electrochemical generation and selec-tive dimerization of persistent radicals is followed by thermal isomerization of the symmetric C8b–C8c dimer to the C3c–C8b isomer, providing rapid entry into the vitisin core.
    [Show full text]
  • Chapter 4. Synthesis of Natural Oligomeric
    CHAPTER 4. SYNTHESIS OF NATURAL OLIGOMERIC STILBENOIDS AND ANALOGUES As mentioned above, stilbene oxidation was carried out with two different techniques: electrochemical oxidation reported in Chapter 3 and via various chemical oxidants in different solvents. The objectives of using these two approaches are to be able to compare their respective merits and develop a biomimetic approach that would mimic what nature does as closely as possible. A comprehensive literature review will summaries published biomimetic oligostilbenoids syntheses based on the author’s approaches as well as non-biomimetic syntheses. This is followed by the results obtained in this study and discussions on establishing the mechanisms involved in the oxidative formation of oligostilbenoids. A comparison will be made with results obtained in the preceding chapter. The structures of prepared oligostilbenoids are confirmed by spectroscopic measurements and/or by comparing with reported spectroscopic data in the literature. Finally, this chapter is completed with an overall conclusion and experimental procedures for oligostilbenoids preparation. 4.1. Oligostilbenoid biomimetic syntheses The work presented below was initiated by the various chemists for different purposes. In some cases the objective was to obtain chemical correlations in order to support proposed structures for newly isolated oligostilbenes. In other instances, metabolic biotransformation of (oligo)stilbenoid alexins by pathogens and/or oxidases was the focus of the investigations. Finally, some groups attempted the biomimetic 76 synthesis of oligostilbenoids as an obvious preparative method. Notwithstanding their objectives, biomimetic syntheses will be presented below by the type of condensing agent, i.e. biological agents (cells or enzymes) or chemical reagents, including one electron oxidants and acid catalysts.
    [Show full text]
  • Optimization of Bioactive Polyphenols Extraction from Picea Mariana Bark
    molecules Article Optimization of Bioactive Polyphenols Extraction from Picea Mariana Bark Nellie Francezon 1,2, Naamwin-So-Bâwfu Romaric Meda 1,2 and Tatjana Stevanovic 1,2,* 1 Renewable Materials Research Centre, Department of Wood and Forest Sciences, Université Laval, Québec, QC G1V 0A6, Canada; [email protected] (N.F.); [email protected] (N.-S.-B.R.M.) 2 Institute of Nutrition and Functional Food (INAF), Université Laval, Quebec, QC G1V 0A6, Canada * Correspondence: [email protected]; Tel.: +1-418-656-2131 Received: 30 October 2017; Accepted: 30 November 2017; Published: 1 December 2017 Abstract: Reported for its antioxidant, anti-inflammatory and non-toxicity properties, the hot water extract of Picea mariana bark was demonstrated to contain highly valuable bioactive polyphenols. In order to improve the recovery of these molecules, an optimization of the extraction was performed using water. Several extraction parameters were tested and extracts obtained analyzed both in terms of relative amounts of different phytochemical families and of individual molecules concentrations. As a result, low temperature (80 ◦C) and low ratio of bark/water (50 mg/mL) were determined to be the best parameters for an efficient polyphenol extraction and that especially for low molecular mass polyphenols. These were identified as stilbene monomers and derivatives, mainly stilbene glucoside isorhapontin (up to 12.0% of the dry extract), astringin (up to 4.6%), resveratrol (up to 0.3%), isorhapontigenin (up to 3.7%) and resveratrol glucoside piceid (up to 3.1%) which is here reported for the first time for Picea mariana. New stilbene derivatives, piceasides O and P were also characterized herein as new isorhapontin dimers.
    [Show full text]
  • List of Compounds 2018 年12 月
    List of Compounds 2018 年12 月 長良サイエンス株式会社 Nagara Science Co., Ltd. 〒501-1121 岐阜市古市場 840 840 Furuichiba, Gifu 501-1121, JAPAN Phone : +81-58-234-4257、Fax : +81-58-234-4724 E-mail : [email protected] 、http : //www.nsgifu.jp Storage Product Name・Purity・Molecular Formula＝Molecular Weight・〔 CAS Quantity Source Code No. C o n di t i o n s Registry Number 〕 ・Price ( JPY ) NH020102 2－10 ℃ (-)-Epicatechin [ (-)-EC ] ≧99% (HPLC) 10mg 8,000 NH020103 C15H14O6 = 290.27 〔490-46-0〕 100mg 44,000 NH020202 2－10 ℃ (-)-Epigallocatechin [ (-)-EGC ] ≧99% (HPLC) 10mg 12,000 NH020203 C15H14O7 = 306.27 〔970-74-1〕 100mg 66,000 NH020302 2－10 ℃ (-)-Epicatechin gallate [ (-)-ECg ] ≧99% (HPLC) 10mg 12,000 NH020303 C22H18O10 = 442.37 〔1257-08-5〕 100mg 52,000 NH020403 2－10 ℃ (-)-Epigallocatechin gallate [ (-)-EGCg ] ≧98% (HPLC) 100mg 12,000 〔 〕 C22H18O11 = 458.37 989-51-5 NH020602 2－10 ℃ (-)-Epigallocatechin gallate [ (-)-EGCg ] ≧99% (HPLC) 20mg 12,000 NH020603 C22H18O11 = 458.37 〔989-51-5〕 100mg 30,000 NH020502 2－10 ℃ (+)-Catechin hydrate [ (+)-C ] ≧99% (HPLC) 10mg 5,000 NH020503 C15H14O6 ･H2O = 308.28 〔88191-48-4〕 100mg 32,000 NH021102 2－10 ℃ (-)-Catechin [ (-)-C ] ≧98% (HPLC) 10mg 23,000 C15H14O6 = 290.27 〔18829-70-4〕 NH021202 2－10 ℃ (-)-Gallocatechin [ (-)-GC ] ≧98% (HPLC) 10mg 34,000 〔 〕 C15H14O7 = 306.27 3371-27-5 NH021302 － ℃ ≧ 10mg 34,000 2 10 (-)-Catechin gallate [ (-)-Cg ] 98% (HPLC) C22H18O10 = 442.37 〔130405-40-2〕 NH021402 2－10 ℃ (-)-Gallocatechin gallate [ (-)-GCg ] ≧98% (HPLC) 10mg 23,000 C22H18O11 = 458.37 〔4233-96-9〕 NH021502 2－10 ℃ (+)-Epicatechin [ (+)-EC
    [Show full text]
  • Applications of Mass Spectrometry in Natural Product Drug Discovery for Malaria: Targeting Plasmodium Falciparum Thioredoxin Reductase
    Applications of mass spectrometry in natural product drug discovery for malaria: Targeting Plasmodium falciparum thioredoxin reductase by Ranjith K. Munigunti A dissertation submitted to the Graduate Faculty of Auburn University in partial fulfillment of the requirements for the Degree of Doctor of Philosophy Auburn, Alabama May 5, 2013 Keywords: Chromatography, mass spectrometry, malaria, Plasmodium falciparum, thioredoxin reductase, thioredoxin Copyright 2013 by Ranjith K. Munigunti Approved by Angela I. Calderón, Chair, Assistant Professor of Pharmacal Sciences C. Randall Clark, Professor of Pharmacal Sciences Jack DeRuiter, Professor of Pharmacal Sciences Forrest Smith, Associate Professor of Pharmacal Sciences Orlando Acevedo, Associate Professor of Chemistry and Biochemistry Abstract Malaria is considered to be the dominant cause of death in low income countries especially in Africa. Malaria caused by Plasmodium falciparum is a most lethal form of the disease because of its rapid spread and the development of drug resistance. The main problem in the treatment of malaria is the emergence of drug resistant malaria parasites. Over the years/decades, natural products have been used for the treatment or prevention of number of diseases. They can serve as compounds of interest both in their natural form and as templates for synthetic modification. Nature has provided a wide variety of compounds that inspired the development of potential therapeutics such as quinine, artemisinin and lapachol as antimalarial agents. As the resistance to known antimalarials is increasing, there is a need to expand the antimalarial drug discovery efforts for new classes of molecules to combat malaria. This research work focuses on the applications of ultrafiltration, mass spectrometry and molecular modeling based approaches to identify inhibitors of Plasmodium falciparum thioredoxin reductase (PfTrxR), our main target and Plasmodium falciparum glutathione reductase (PfGR) as an alternative target for malaria drug discovery.
    [Show full text]
  • Oxyresveratrol의 기원, 생합성, 생물학적 활성 및 약물동력학
    KOREAN J. FOOD SCI. TECHNOL. Vol. 47, No. 5, pp. 545~555 (2015) http://dx.doi.org/10.9721/KJFST.2015.47.5.545 총설 ©The Korean Society of Food Science and Technology Oxyresveratrol의 기원, 생합성, 생물학적 활성 및 약물동력학 임영희·김기현 1·김정근 1,* 고려대학교 보건과학대학 바이오시스템의과학부, 1한국산업기술대학교 생명화학공학과 Source, Biosynthesis, Biological Activities and Pharmacokinetics of Oxyresveratrol 1 1, Young-Hee Lim, Ki-Hyun Kim , and Jeong-Keun Kim * School of Biosystem and Biomedical Science, Korea University 1Department of Chemical Engineering and Biotechnology, Korea Polytechnic University Abstract Oxyresveratrol (trans-2,3',4,5'-tetrahydroxystilbene) has been receiving increasing attention because of its astonishing biological activities, including antihyperlipidemic, neuroprotection, antidiabetic, anticancer, antiinflammation, immunomodulation, antiaging, and antioxidant activities. Oxyresveratrol is a stilbenoid, a type of natural phenol and a phytoalexin produced in the roots, stems, leaves, and fruits of several plants. It was first isolated from the heartwood of Artocarpus lakoocha, and has also been found in various plants, including Smilax china, Morus alba, Varatrum nigrum, Scirpus maritinus, and Maclura pomifera. Oxyresveratrol, an aglycone of mulberroside A, has been produced by microbial biotransformation or enzymatic hydrolysis of a glycosylated stilbene mulberroside A, which is one of the major compounds of the roots of M. alba. Oxyresveratrol shows less cytotoxicity, better antioxidant activity and polarity, and higher cell permeability and bioavailability than resveratrol (trans-3,5,4'-trihydroxystilbene), a well-known antioxidant, suggesting that oxyresveratrol might be a potential candidate for use in health functional food and medicine. This review focuses on the plant sources, chemical characteristics, analysis, biosynthesis, and biological activities of oxyresveratrol as well as describes the perspectives on further exploration of oxyresveratrol.
    [Show full text]
  • Literature Review Zero Alcohol Red Wine
    A 1876 LI A A U R S T T S R U A L A I A FLAVOURS, FRAGRANCES AND INGREDIENTS 6 1 7 8 7 8 1 6 A I B A L U A S R T B Essential Oils, Botanical Extracts, Cold Pressed Oils, BOTANICAL Infused Oils, Powders, Flours, Fermentations INNOVATIONS LITERATURE REVIEW HEALTH BENEFITS RED WINE ZERO ALCOHOL RED WINE RED WINE EXTRACT POWDER www.botanicalinnovations.com.au EXECUTIVE SUMMARY The term FRENCH PARADOX is used to describe the relatively low incidence of cardiovascular disease in the French population despite the high consumption of red wine. Over the past 27 years numerous clinical studies have found a linkages with the ANTIOXIDANTS in particular, the POLYPHENOLS, RESVERATROL, CATECHINS, QUERCERTIN and ANTHOCYANDINS in red wine and reduced incidences of cardiovascular disease. However, the alcohol in wine limits the benefits of wine. Studies have shown that zero alcohol red wine and red wine extract which contain the same ANTIOXIDANTS including POLYPHENOLS, RESVERATROL, CATECHINS, QUERCERTIN and ANTHOCYANDINS has the same is not more positive health benefits. The following literature review details some of the most recent positive health benefits derived from the ANTIOXIDANTS found in red wine POLYPHENOLS: RESVERATROL, CATECHINS, QUERCERTIN and ANTHOCYANDINS. The positive polyphenolic antioxidant effects of the polyphenols in red wine include: • Cardio Vascular Health Benefits • Increase antioxidants in the cardiovascular system • Assisting blood glucose control • Skin health • Bone Health • Memory • Liking blood and brain health • Benefits
    [Show full text]
  • Molecular Cloning and Functional Characterization of an O-Methyltransferase Catalyzing 4 -O-Methylation of Resveratrol in Acorus
    Journal of Bioscience and Bioengineering VOL. 127 No. 5, 539e543, 2019 www.elsevier.com/locate/jbiosc Molecular cloning and functional characterization of an O-methyltransferase catalyzing 40-O-methylation of resveratrol in Acorus calamus Takao Koeduka,1,* Miki Hatada,1 Hideyuki Suzuki,2 Shiro Suzuki,3 and Kenji Matsui1 Graduate School of Sciences and Technology for Innovation (Agriculture), Department of Biological Chemistry, Yamaguchi University, Yamaguchi 753-8515, Japan,1 Department of Applied Genomics, Kazusa DNA Research Institute, Chiba 292-0818, Japan,2 and Research Institute for Sustainable Humanosphere, Kyoto University, Kyoto 611-0011, Japan3 Received 17 July 2018; accepted 13 October 2018 Available online 22 November 2018 Resveratrol and its methyl ethers, which belong to a class of natural polyphenol stilbenes, play important roles as biologically active compounds in plant defense as well as in human health. Although the biosynthetic pathway of resveratrol has been fully elucidated, the characterization of resveratrol-specific O-methyltransferases remains elusive. In this study, we used RNA-seq analysis to identify a putative aromatic O-methyltransferase gene, AcOMT1,inAcorus calamus. Recombinant AcOMT1 expressed in Escherichia coli showed high 40-O-methylation activity toward resveratrol and its derivative, isorhapontigenin. We purified a reaction product enzymatically formed from resveratrol by AcOMT1 and confirmed it as 40-O-methylresveratrol (deoxyrhapontigenin). Resveratrol and isorhapontigenin were the most preferred substrates with apparent Km values of 1.8 mM and 4.2 mM, respectively. Recombinant AcOMT1 exhibited reduced activity toward other resveratrol derivatives, piceatannol, oxyresveratrol, and pinostilbene. In contrast, re- combinant AcOMT1 exhibited no activity toward pterostilbene or pinosylvin. These results indicate that AcOMT1 showed high 40-O-methylation activity toward stilbenes with non-methylated phloroglucinol rings.
    [Show full text]
  • Anti-Tumor Properties of Methoxylated Analogues of Resveratrol in Malignant MCF-7 but Not in Non-Tumorigenic MCF-10A Mammary Epithelial Cell Lines T ⁎ Annick D
    Toxicology 422 (2019) 35–43 Contents lists available at ScienceDirect Toxicology journal homepage: www.elsevier.com/locate/toxicol Anti-tumor properties of methoxylated analogues of resveratrol in malignant MCF-7 but not in non-tumorigenic MCF-10A mammary epithelial cell lines T ⁎ Annick D. van den Brand , Judith Villevoye, Sandra M. Nijmeijer, Martin van den Berg, Majorie B.M. van Duursen Institute for Risk Assessment Sciences, Toxicology Department, Utrecht University, Yalelaan 104, 3584 CM, Utrecht, the Netherlands ARTICLE INFO ABSTRACT Keywords: Resveratrol is a plant-derived polyphenol that is known for its anti-inflammatory and anti-tumorigenic prop- Cell cycle erties in in vitro and in vivo models. Recent studies show that some resveratrol analogues might be more potent Gene expression anti-tumor agents, which may partly be attributed to their ability to activate the aryl hydrocarbon receptor Breast cancer (AHR). Here, the anti-tumorigenic properties of resveratrol and structural analogues oxyresveratrol, pinos- Resveratrol tilbene, pterostilbene and tetramethoxystilbene (TMS) were studied in vitro, using in the malignant human MCF- 7 breast cancer cell line and non-tumorigenic breast epithelial cell line MCF-10A. Cell viability and migration assays showed that methoxylated analogues of resveratrol are more potent anti- tumorigenic compounds than resveratrol and its hydroxylated analogue oxyresveratrol, with 2,3’,4,5’-tetra- methoxy-trans-stilbene (TMS) being the most potent compound. TMS decreased MCF-7 tumor cell viability with 50% at 3.6 μM and inhibited migration with 37.5 ± 14.8% at 3 μM. In addition, TMS activated the AHR more potently (EC50 in a reporter gene assay 2.0 μM) and induced AHR-mediated induction of cytochrome P450 1A1 (CYP1A1) activity (EC50 value of 0.7 μM) more than resveratrol and the other analogues tested.
    [Show full text]
  • Extraction Et Hémisynthèse De Stilbènes De La Vigne Et Du Vin Pour Une Application En Santé Humaine Et Végétale Toni El Khawand
    Extraction et hémisynthèse de stilbènes de la vigne et du vin pour une application en santé humaine et végétale Toni El Khawand To cite this version: Toni El Khawand. Extraction et hémisynthèse de stilbènes de la vigne et du vin pour une application en santé humaine et végétale. Médecine humaine et pathologie. Université de Bordeaux, 2019. Français. NNT : 2019BORD0402. tel-03083318 HAL Id: tel-03083318 https://tel.archives-ouvertes.fr/tel-03083318 Submitted on 19 Dec 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. THÈSE PRÉSENTÉE POUR OBTENIR LE GRADE DE DOCTEUR DE L’UNIVERSITÉ DE BORDEAUX ÉCOLE DOCTORALE DES SCIENCES DE LA VIE ET DE LA SANTÉ SPÉCIALITÉ ŒNOLOGIE Par Toni EL KHAWAND Extraction et hémisynthèse de stilbènes de la vigne et du vin pour une application en santé humaine et végétale Sous la direction du Dr. Alain DECENDIT la co-direction du Pr. Tristan RICHARD et le co-encadrement du Dr. Stéphanie KRISA Soutenue publiquement le 18 décembre 2019 Membres du jury M. Rémy GHIDOSSI Professeur, Université de Bordeaux Président Mme. Marielle ADRIAN Professeur, Université de Bourgogne Rapporteur Mme. Laurence VOUTQUENNE Professeur, Université de Reims Rapporteur M.
    [Show full text]
  • Metabolism of Stilbenoids by Human Faecal Microbiota
    molecules Article Metabolism of Stilbenoids by Human Faecal Microbiota Veronika Jarosova 1,2 , Ondrej Vesely 1, Petr Marsik 1, Jose Diogenes Jaimes 1 , Karel Smejkal 3, Pavel Kloucek 1 and Jaroslav Havlik 1,* 1 Department of Food Science, Czech University of Life Sciences Prague, Kamycka 129, 165 00 Prague 6–Suchdol, Czech Republic; [email protected] (V.J.); [email protected] (O.V.); [email protected] (P.M.); [email protected] (J.D.J.); [email protected] (P.K.) 2 Department of Microbiology, Nutrition and Dietetics, Czech University of Life Sciences Prague, Kamycka 129, 165 00 Prague 6–Suchdol, Czech Republic 3 Department of Natural Drugs, Faculty of Pharmacy, University of Veterinary and Pharmaceutical Sciences Brno, Palackeho 1946/1, 612 42 Brno, Czech Republic; [email protected] * Correspondence: [email protected]; Tel.: +420-777-558-468 Academic Editors: Pedro Mena and Rafael Llorach Asunción Received: 18 February 2019; Accepted: 18 March 2019; Published: 23 March 2019 Abstract: Stilbenoids are dietary phenolics with notable biological effects on humans. Epidemiological, clinical, and nutritional studies from recent years have confirmed the significant biological effects of stilbenoids, such as oxidative stress protection and the prevention of degenerative diseases, including cancer, cardiovascular diseases, and neurodegenerative diseases. Stilbenoids are intensively metabolically transformed by colon microbiota, and their corresponding metabolites might show different or stronger biological activity than their parent molecules. The aim of the present study was to determine the metabolism of six stilbenoids (resveratrol, oxyresveratrol, piceatannol, thunalbene, batatasin III, and pinostilbene), mediated by colon microbiota. Stilbenoids were fermented in an in vitro faecal fermentation system using fresh faeces from five different donors as an inoculum.
    [Show full text]
  • Isorhapontigenin, a Resveratrol Analogue Selectively Inhibits ADP-Stimulated Platelet Activation
    Isorhapontigenin, a resveratrol analogue selectively inhibits ADP-stimulated platelet activation Article Accepted Version Creative Commons: Attribution-Noncommercial-No Derivative Works 4.0 Ravishankar, D., Albadawi, D., Chaggar, V., Patra, P., Williams, H., Salamah, M., Vaiyapuri, R., Dash, P., Patel, K., Watson, K. and Vaiyapuri, S. (2019) Isorhapontigenin, a resveratrol analogue selectively inhibits ADP-stimulated platelet activation. European Journal of Pharmacology, 862. 172627. ISSN 0014-2999 doi: https://doi.org/10.1016/j.ejphar.2019.172627 Available at http://centaur.reading.ac.uk/85806/ It is advisable to refer to the publisher’s version if you intend to cite from the work. See Guidance on citing . To link to this article DOI: http://dx.doi.org/10.1016/j.ejphar.2019.172627 Publisher: Elsevier All outputs in CentAUR are protected by Intellectual Property Rights law, including copyright law. Copyright and IPR is retained by the creators or other copyright holders. Terms and conditions for use of this material are defined in the End User Agreement . www.reading.ac.uk/centaur CentAUR Central Archive at the University of Reading Reading’s research outputs online Isorhapontigenin, a resveratrol analogue selectively inhibits ADP-stimulated platelet activation 1 1 1 1 Divyashree Ravishankar , Dina A I Albadawi , Vishaant Chaggar , Pabitra H Patra , Harry F Williams1, Maryam Salamah1, Rajendran Vaiyapuri2, Philip R Dash3, Ketan Patel3, Kimberly A Watson3, Sakthivel Vaiyapuri1♯ 1School of Pharmacy, University of Reading, Reading, UK 2School of Pharmacy, University of Reading Malaysia, Johor, Malaysia 3School of Biological Sciences, University of Reading, Reading, UK Corresponding Author ♯Sakthivel Vaiyapuri, School of Pharmacy, University of Reading, Reading, UK Tel: +44 (0)118 378 8015 E-mail address: [email protected] 1 Abstract Isorhapontigenin is a polyphenolic compound found in Chinese herbs and grapes.
    [Show full text]