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Stilbenes: Chemistry and Pharmacological Properties
1 Journal of Applied Pharmaceutical Research 2015, 3(4): 01-07 JOURNAL OF APPLIED PHARMACEUTICAL RESEARCH ISSN No. 2348 – 0335 www.japtronline.com STILBENES: CHEMISTRY AND PHARMACOLOGICAL PROPERTIES Chetana Roat*, Meenu Saraf Department of Microbiology & Biotechnology, University School of Sciences, Gujarat University, Ahmedabad, Gujarat 380009, India Article Information ABSTRACT: Medicinal plants are the most important source of life saving drugs for the Received: 21st September 2015 majority of the Worlds’ population. The compounds which synthesized in the plant from the Revised: 15th October 2015 secondary metabolisms are called secondary metabolites; exhibit a wide array of biological and Accepted: 29th October 2015 pharmacological properties. Stilbenes a small class of polyphenols, have recently gained the focus of a number of studies in medicine, chemistry as well as have emerged as promising Keywords molecules that potentially affect human health. Stilbenes are relatively simple compounds Stilbene; Chemistry; synthesized by plants and deriving from the phenyalanine/ polymalonate route, the last and key Structures; Biosynthesis pathway; enzyme of this pathway being stilbene synthase. Here, we review the biological significance of Pharmacological properties stilbenes in plants together with their biosynthesis pathway, its chemistry and its pharmacological significances. INTRODUCTION quantities are present in white and rosé wines, i.e. about a tenth Plants are source of several drugs of natural origin and hence of those of red wines. Among these phenolic compounds, are termed as the medicinal plants. These drugs are various trans-resveratrol, belonging to the stilbene family, is a major types of secondary metabolites produced by plants; several of active ingredient which can prevent or slow the progression of them are very important drugs. -
Sphingolipids and Cell Signaling: Relationship Between Health and Disease in the Central Nervous System
Preprints (www.preprints.org) | NOT PEER-REVIEWED | Posted: 6 April 2021 doi:10.20944/preprints202104.0161.v1 Review Sphingolipids and cell signaling: Relationship between health and disease in the central nervous system Andrés Felipe Leal1, Diego A. Suarez1,2, Olga Yaneth Echeverri-Peña1, Sonia Luz Albarracín3, Carlos Javier Alméciga-Díaz1*, Angela Johana Espejo-Mojica1* 1 Institute for the Study of Inborn Errors of Metabolism, Faculty of Science, Pontificia Universidad Javeriana, Bogotá D.C., 110231, Colombia; [email protected] (A.F.L.), [email protected] (D.A.S.), [email protected] (O.Y.E.P.) 2 Faculty of Medicine, Universidad Nacional de Colombia, Bogotá D.C., Colombia; [email protected] (D.A.S.) 3 Nutrition and Biochemistry Department, Faculty of Science, Pontificia Universidad Javeriana, Bogotá D.C., Colombia; [email protected] (S.L.A.) * Correspondence: [email protected]; Tel.: +57-1-3208320 (Ext 4140) (C.J.A-D.). [email protected]; Tel.: +57-1-3208320 (Ext 4099) (A.J.E.M.) Abstract Sphingolipids are lipids derived from an 18-carbons unsaturated amino alcohol, the sphingosine. Ceramide, sphingomyelins, sphingosine-1-phosphates, gangliosides and globosides, are part of this group of lipids that participate in important cellular roles such as structural part of plasmatic and organelle membranes maintaining their function and integrity, cell signaling response, cell growth, cell cycle, cell death, inflammation, cell migration and differentiation, autophagy, angiogenesis, immune system. The metabolism of these lipids involves a broad and complex network of reactions that convert one lipid into others through different specialized enzymes. Impairment of sphingolipids metabolism has been associated with several disorders, from several lysosomal storage diseases, known as sphingolipidoses, to polygenic diseases such as diabetes and Parkinson and Alzheimer diseases. -
GM2 Gangliosidoses: Clinical Features, Pathophysiological Aspects, and Current Therapies
International Journal of Molecular Sciences Review GM2 Gangliosidoses: Clinical Features, Pathophysiological Aspects, and Current Therapies Andrés Felipe Leal 1 , Eliana Benincore-Flórez 1, Daniela Solano-Galarza 1, Rafael Guillermo Garzón Jaramillo 1 , Olga Yaneth Echeverri-Peña 1, Diego A. Suarez 1,2, Carlos Javier Alméciga-Díaz 1,* and Angela Johana Espejo-Mojica 1,* 1 Institute for the Study of Inborn Errors of Metabolism, Faculty of Science, Pontificia Universidad Javeriana, Bogotá 110231, Colombia; [email protected] (A.F.L.); [email protected] (E.B.-F.); [email protected] (D.S.-G.); [email protected] (R.G.G.J.); [email protected] (O.Y.E.-P.); [email protected] (D.A.S.) 2 Faculty of Medicine, Universidad Nacional de Colombia, Bogotá 110231, Colombia * Correspondence: [email protected] (C.J.A.-D.); [email protected] (A.J.E.-M.); Tel.: +57-1-3208320 (ext. 4140) (C.J.A.-D.); +57-1-3208320 (ext. 4099) (A.J.E.-M.) Received: 6 July 2020; Accepted: 7 August 2020; Published: 27 August 2020 Abstract: GM2 gangliosidoses are a group of pathologies characterized by GM2 ganglioside accumulation into the lysosome due to mutations on the genes encoding for the β-hexosaminidases subunits or the GM2 activator protein. Three GM2 gangliosidoses have been described: Tay–Sachs disease, Sandhoff disease, and the AB variant. Central nervous system dysfunction is the main characteristic of GM2 gangliosidoses patients that include neurodevelopment alterations, neuroinflammation, and neuronal apoptosis. Currently, there is not approved therapy for GM2 gangliosidoses, but different therapeutic strategies have been studied including hematopoietic stem cell transplantation, enzyme replacement therapy, substrate reduction therapy, pharmacological chaperones, and gene therapy. -
Mouse Model of GM2 Activator Deficiency Manifests Cerebellar Pathology and Motor Impairment
Proc. Natl. Acad. Sci. USA Vol. 94, pp. 8138–8143, July 1997 Medical Sciences Mouse model of GM2 activator deficiency manifests cerebellar pathology and motor impairment (animal modelyGM2 gangliosidosisygene targetingylysosomal storage disease) YUJING LIU*, ALEXANDER HOFFMANN†,ALEXANDER GRINBERG‡,HEINER WESTPHAL‡,MICHAEL P. MCDONALD§, KATHERINE M. MILLER§,JACQUELINE N. CRAWLEY§,KONRAD SANDHOFF†,KINUKO SUZUKI¶, AND RICHARD L. PROIA* *Section on Biochemical Genetics, Genetics and Biochemistry Branch, National Institute of Diabetes and Digestive and Kidney Diseases, ‡Laboratory of Mammalian Genes and Development, National Institute of Child Health and Development, and §Section on Behavioral Neuropharmacology, Experimental Therapeutics Branch, National Institute of Mental Health, National Institutes of Health, Bethesda, MD 20892; †Institut fu¨r Oganische Chemie und Biochemie der Universita¨tBonn, Gerhard-Domagk-Strasse 1, 53121 Bonn, Germany; and ¶Department of Pathology and Laboratory Medicine, and Neuroscience Center, University of North Carolina, Chapel Hill, NC 27599 Communicated by Stuart A. Kornfeld, Washington University School of Medicine, St. Louis, MO, May 12, 1997 (received for review March 21, 1997) ABSTRACT The GM2 activator deficiency (also known as disorder, the respective genetic lesion results in impairment of the AB variant), Tay–Sachs disease, and Sandhoff disease are the the degradation of GM2 ganglioside and related substrates. major forms of the GM2 gangliosidoses, disorders caused by In humans, in vivo GM2 ganglioside degradation requires the defective degradation of GM2 ganglioside. Tay–Sachs and Sand- GM2 activator protein to form a complex with GM2 ganglioside. hoff diseases are caused by mutations in the genes (HEXA and b-Hexosaminidase A then is able to interact with the activator- HEXB) encoding the subunits of b-hexosaminidase A. -
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. -
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. -
Metabolites-10-00232-V3.Pdf
H OH metabolites OH Article Wood Metabolomic Responses of Wild and Cultivated Grapevine to Infection with Neofusicoccum parvum, a Trunk Disease Pathogen Clément Labois 1,2 , Kim Wilhelm 2,Hélène Laloue 1,Céline Tarnus 1, Christophe Bertsch 1, Mary-Lorène Goddard 1,2,* and Julie Chong 1,* 1 Laboratoire Vigne, Biotechnologies et Environnement (LVBE, EA3991), Université de Haute Alsace, 68000 Colmar, France; [email protected] (C.L.); [email protected] (H.L.); [email protected] (C.T.); [email protected] (C.B.) 2 Laboratoire d’Innovation Moléculaire et Applications, Université de Haute-Alsace, Université de Strasbourg, CNRS, LIMA, UMR 7042, 68093 Mulhouse cedex, France; [email protected] * Correspondence: [email protected] (M.-L.G.); [email protected] (J.C.); Tel.: +33-3-89-33-67-69 (M.-L.G.); +33-3-89-20-31-39 (J.C.) Received: 28 April 2020; Accepted: 30 May 2020; Published: 4 June 2020 Abstract: Grapevine trunk diseases (GTDs), which are associated with complex of xylem-inhabiting fungi, represent one of the major threats to vineyard sustainability currently. Botryosphaeria dieback, one of the major GTDs, is associated with wood colonization by Botryosphaeriaceae fungi, especially Neofusicoccum parvum. We used GC-MS and HPLC-MS to compare the wood metabolomic responses of the susceptible Vitis vinifera subsp. vinifera (V. v. subsp. vinifera) and the tolerant Vitis vinifera subsp. sylvestris (V. v. subsp. sylvestris) after artificial inoculation with Neofusicoccum parvum (N. parvum). N. parvum inoculation triggered major changes in both primary and specialized metabolites in the wood. In both subspecies, infection resulted in a strong decrease in sugars (fructose, glucose, sucrose), whereas sugar alcohol content (mannitol and arabitol) was enhanced. -
Acuminatol and Other Antioxidative Resveratrol Oligomers from the Stem Bark of Shorea Acuminata
Molecules 2012, 17, 9043-9055; doi:10.3390/molecules17089043 OPEN ACCESS molecules ISSN 1420-3049 www.mdpi.com/journal/molecules Article Acuminatol and Other Antioxidative Resveratrol Oligomers from the Stem Bark of Shorea acuminata Norhayati Muhammad 1, Laily B. Din 1, Idin Sahidin 2, Siti Farah Hashim 3, Nazlina Ibrahim 3, Zuriati Zakaria 4 and Wan A. Yaacob 1,* 1 School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM Bangi 43600, Selangor D.E., Malaysia; E-Mails: [email protected] (N.M.); [email protected] (L.B.D.) 2 Faculty of Mathematics and Natural Sciences, Haluoleo University, Kendari 93232, Sulawesi Tenggara, Indonesia; E-Mail: [email protected] 3 School of Biosciences and Biotechnology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, UKM Bangi 43600, Selangor D.E., Malaysia; E-Mails: [email protected] (S.F.H.); [email protected] (N.I.) 4 Malaysia-Japan International Institute of Technology, Universiti Teknologi Malaysia Kuala Lumpur, Jalan Semarak, Kuala Lumpur 54100, Malaysia; E-Mail: [email protected] * Author to whom correspondence should be addressed; E-Mail: [email protected]; Tel.: +603-8921-5424; Fax: +603-8921-5410. Received: 1 June 2012; in revised form: 10 July 2012 / Accepted: 18 July 2012 / Published: 30 July 2012 Abstract: A new resveratrol dimer, acuminatol (1), was isolated along with five known compounds from the acetone extract of the stem bark of Shorea acuminata. Their structures and stereochemistry were determined by spectroscopic methods, which included the extensive use of 2D NMR techniques. All isolated compounds were evaluated for their antioxidant activity using the 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging activity (RSA) and the β-carotene-linoleic acid (BCLA) assays, and compared with those of the standards of ascorbic acid (AscA) and butylated hydroxytoluene (BHT). -
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 -
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. -
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. -
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.