DOCSLIB.ORG

Electronic Supplementary Material (ESI) for Natural Product Reports

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Electronic Supplementary Material (ESI) for Natural Product Reports Electronic Supplementary Material (ESI) for Natural Product Reports. This journal is © The Royal Society of Chemistry 2020 SUPPLEMENTARY INFORMATION Figure S1 Figure S2 Figure S3 Figure S4 Table S1 Table S2 Legends of the figures Figure S1: Biosynthetic pathways to aromatic amino acids and malonyl-CoA from glucose. Abbreviations used: DAHP, 2-keto-3-deoxy-D-arabino-heptulosonate-7-phosphate; ACC, acetyl-CoA carboxylase complex, CM1, chorismate mutase 1; PPA-AT, prephenate aminotransferase; ADT, arogenate dehydratase; ADH, arogenate dehydrogenase Figure S2: Putative relationships between 8-8’ dimeric naturally-occurring stilbenes (according to Stephenson’s group29) Figure S3: Examples of stilbene tetramers resulting from the 3-8’ condensation of e-viniferin. The two tetramers, vitisin A and vitisin B isolated from grapevine root extracts result from the 3-8’ coupling of two oxidized molecules of (-)--viniferin (according to Stephenson’s group29) Figure S4: Hypothetical mechanism for the formation of a stilbene heptamer. The stilbene heptamer pauciflorol D is formed by condensation between the resveratrol 8-10’ tetramer, vaticaphenol A, and an 8-8’ quinone trimer formed by the coupling of three resveratrol hydroxyphenyl radicals C (according to Stephenson’s group29) Pentose Phosphate GLUCOSE Glycolysis Pathway Pathway Erythrose-4-phosphate Phosphoenolpyruvate DAHP synthase Shikimate Pathway Pyruvate DAHP Pyruvate Dehydrogenase Complex Acetyl-CoA COOH ACC CO2 O O HO OH HO SCoA OH Malonyl CoA Shikimate COOH O COOH OH Chorismate Chorismate mutase 1 CM1 COOH COOH O HO Prephenate Arogenate Pathway Prephenate aminotransferase PPA-AT COOH COOH NH2 HO Arogenate Arogenate dehydratase Arogenate dehydrogenase ADT ADH COOH COOH NH2 NH2 HO Tyrosine Phenylalanine Figure S1 HO OH HO Phenanthrenic ring OH HO H OH OH HO H HO H h -2H+ H OH OH H H OH OH OH OH OH (-)-Quadrangularin A OH OH (-)-Parthenocissin A (+)-Laetevirenol A HO HO H H O H O H H HO -2H+ HO H H OH -H2O H OH OH OH O HO OH Vitisinol A Restrytisol A Figure S2 HO HO H H 3-8' COUPLING HO O O HO HO H OH H OH OH HRP / H2O2 A OH OH OH OH OH OH H B HO H OH HO H OH O OH O A H H HO H H H H O O 2 x -Viniferin HO HO O HO Hypothetical Intermediate Vitisin B (Tetramer) B HO H O HO H OH OH OH HO H H OH HO H O OH H OH Vitisin A (Tetramer) Figure S3 HEPTAMER FORMATION OH HO HO OH B1 C2 OH HO H H HO HO [O] B2 OH HO D HO H 2 OH O H OH H H H HO C2 H H HO H OH A1 A2 O D1 H H O OH H OH O HO H Vaticaphenol A HO H -Viniferin HO H OH HO H O OH OH HO O HO H OH E1 OH OH G2 HO H G1 H OH OH [O] H HO H H H E 2 H O OH H HO F2 H OH H F1 OH H HO OH O 102 OH 3 x Resveratrol HO OH Hypothetical Intermediate Pauciflorol D (Stilbene heptamer) Figure S4 Table S1 Antifungal activity of stilbene monomers and oligomers towards various microorganisms Tested stilbenes Microorganisms/structures Inhibiting activity References Cladosporium cuccumerinum (spores) Botrytis cinerea (spores) Resveratrol ED > 870 M 17 Pyricularia oryzae (spores) 50 Plasmopara viticola (zoospore motility) B. cinerea (mycelium) ED50 : 438 M Resveratrol P. oryzae (mycelium) ED50 : 276 M 17 Fusarium oxysporum (mycelium) ED50 : 88 M Resveratrol B. cinerea (spores) ED50 : 390 M 117 Fungal growth Stereum hirsutum inhibition at 490 M Fomitiporia punctata Resveratrol Ineffective or 283 Libertella blepharis stimulator on fungal Phaeomoniella chlamydospora growth at 490 M Phaeoacremonium aleophilum 57.2% growth decrease at 48 M Yeast 16.1% growth Resveratrol Penicillium expansum decrease at 48 M 284 Aspergillus niger 36.4% growth decrease at 48 M Table S1 Antifungal activity of stilbene monomers and oligomers towards various microorganisms (continued) P. viticola ED50 : 192 M (zoospore motility) Resveratrol 282 P. viticola ED50 : 145 M (disease development) Resveratrol B. cinerea (spores) ED50 : 438 M 280 P. viticola Resveratrol ED : 500 M 286 (zoospore motility) 100 P. viticola Resveratrol ED : 484 M 287 (sporulation) 50 Resveratrol B. cinerea (spores) ED50 : 1153 M 281 B. cinerea (spores) ED50 : 70 M Pterostilbene P. oryzae (spores) ED50 : 35 M 112 P. viticola (sporangia release) ED50 : 17.6 M Pterostilbene P. viticola ED50 : 9 M 288 (zoospore motility) Pterostilbene B. cinerea (spores) ED50 : 70 M 289 Pterostilbene B. cinerea (spores) ED50 : 78 M 117 Pterostilbene Esca disease-associated fungi Inhibition of fungal 283 growth (39 to 390 M) Table S1 Antifungal activity of stilbene monomers and oligomers towards various microorganisms (continued) P. viticola Pterostilbene ED : 14.6 M 282 (zoospore motility) 50 Piceatannol ED50 : 254 M Isorhapontigenin ED : 116 M Development of downy mildew 50 290 Astringin ED50 : 705 M Isorhapontin ED50 : 272 M -viniferin B. cinerea (spores) ED : 220 M 50 288 -viniferin B. cinerea (mycelium growth) ED50 : 230 M -viniferin P. viticola (sporulation) ED : 12.7 M 50 282,287 -viniferin P. viticola (sporulation) ED50 : 70 M Glucosylateddimers Piceasides I-L ED50 : 96-147 M Development of downy mildew 290 Ampelopsin A ED50 : 934 M Stilbene tetramers Hopeaphenol ED50 : 18 M Miyabenol C ED : 40 M Development of downy mildew 50 287 Vitisin A ED50 : 20 M Vitisin B ED50 : 12 M Table S2 Metabolic engineering of stilbene pathways in yeast Strain used for Incorporated genes Substrate Stilbenes produced References transformation 4CL from Populus Saccharomyces trichocarpa X Populus p-coumarate Resveratrol (1.45 μg/L) 394 cerevisiae FY23 deltoides, STS from Vitis vinifera 4CL from Nicotiana S.cerevisiae tabacum, STS from V. p-coumarate Resveratrol (5.8 mg/L) 395 CEN.PK113-3b vinifera TAL from Rhodobacter sphaeroides, 4CL::STS- S.cerevisiae 4CL from Arabidopsis p-coumarate Resveratrol (5.25 mg/L) 398 WAT11 thaliana and STS from V. vinifera TAL from Rhodotorula Yarrowia glutinis, 4CL from Tyrosine Resveratrol (1.46 mg/L) 408 lipolytica Streptomyces coelicolor, STS from V. vinifera PAL and CPR from P. S. cerevisiae trichocarpia x P. YPH499 deltoides, C4H and 4CL Phenylalanine Resveratrol (0.31 mg/L) 403 from Glycine max, STS from V. vinifera S. cerevisiae 4CL from A. thaliana, STS p-coumarate Resveratrol (391 mg/L) CEN.PK2–1 from V. vinifera 397 4CL from A. thaliana, STS S. cerevisiae from A. hypogea, ∆PAD1 p-coumarate Resveratrol (3.1 mg/L) 396 W303-1A in S. cerevisiae TAL from R. sphaeroides, S. cerevisiae 4CL::STS, 4CL from A. Tyrosine Resveratrol (3.1 mg/L) 406 WAT11 thaliana and STS from V. vinifera, araE from E. coli Table S2 Metabolic engineering of stilbene pathways in yeast (continued) 4CL::STS, 4CL from A. S. cerevisiae thaliana and STS from V. Tyrosine Resveratrol (14.4 mg/L) 402 WAT11 vinifera PAL from Rhodosporidium S. cerevisiae toruloides, C4H and 4CL Tyrosine Resveratrol (5.8 mg/L) 407 W303-1A from A. thaliana, STS from A. hypogea, ACC1 from S. cerevisiae TAL from Herpetosiphon aurianticus, 4CL from S. cerevisiae Arabidopsis thaliana and Glucose/ Resveratrol (415.65 with 386 CEN.PK102-5B STS from V. vinifera, Ethanol glucose/531.41 mg/L ScARO4K229L, ScARO7G141S, with ethanol) ACCS659A, S1157A PAL, C4H, ATR2 and 4CL from A. thaliana, STS from V. vinifera, ACS S. cerevisiae from Salmonella enterica, CEN.PK102-5B Resveratrol (800 mg/L) 387 AroL from E. coli, CYB5 Glucose Pinostilbene (5.5 mg/L) from S. cerevisiae Pterostilbene SbROMT from Sorghum (34.93 mg/L) bicolor/VvROMT from V. vinifera, ∆ARO10 in S. cerevisiae Abbreviations used: PAL, phenylalanine ammonia lyase, TAL, tyrosine ammonia lyase, C4H, cinnamate-4-hydroxylase; 4CL, p-coumaroyl-CoA ligase; STS, stilbene synthase; ACC, acetyl-CoA carboxylase complex; ROMT, resveratrol-O- methyltransferase; ARO10, gene encoding the phenylpyruvate decarboxylase; ScARO4K229L and ScARO7G141S genes encoding feedback-inhibition resistant versions of DAHP synthase and chorismate mutase, respectively; araE, arabinose- H+-transporter; PAD1 gene encoding the phenyl acrylic acid decarboxylase; CPR, cytochrome P450 reductases; aroL, shikimate kinase 2..
Load more

Recommended publications
  • 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.
    [Show full text]
  • Spruce Bark Extract As a Sun Protection Agent in Sunscreens
    Mengmeng Sui Spruce bark extract as a Sun protection agent in sunscreens School of Chemical Engineering Master’s Program in Chemical, Biochemical and Materials Engineering Major in Chemical Engineering Master’s thesis for the degree of Master of Science in Technology Submitted for inspection, Espoo 21.07.2018 Thesis supervisor: Prof. Tapani Vuorinen Thesis advisors: M.Sc. (Tech.) Jinze Dou Ph.D. Kavindra Kesari AALTO UNIVERSITY SCHOLLO OF CHEMICAL ENGINEERING ABSTRACT Author: Mengmeng Sui Title: Spruce bark extract as a sun protection agent in sunscreens Date: 21.07. 2018 Language: English Number of pages: 48+7 Master’s programme in Chemical, Biochemical and Materials Engineering Major: Chemical and Process Engineering Supervisor: Prof: Tapani Vuorinen Advisors: M.Sc. (Tech.) Jinze Dou, Ph.D. Kavindra Kesari This study aimed to clarify the feasibility of utilizing spruce inner bark extract as a sun protection agent in sunscreens. Ultrasound-assisted extraction with 60 v-% ethanol was applied to isolate the extract in 25-30 % yield, that was almost independent of the temperature (45-75oC) and time (5-60 min) of the treatment. However, the yield of stilbene glucosides, measured by UV absorption spectroscopy, was highest after ca. 20 min extraction. Nuclear magnetic resonance spectroscopy of the extract showed that it consisted mainly of three stilbene glucosides, astringin, isorhapontin and polydatin (piceid). The maximum overall yield of the stilbene glucosides was > 20 %. Extraction with water gave a much lower yield of the stilbene glucosides. Sunscreens composed of a mixture of vegetable oils, surfactants (fatty acids), glycerin, water and the bark extract were prepared with the low-energy emulsification method.
    [Show full text]
  • Promising Neuroprotective Effects of Oligostilbenes
    Nutrition and Aging 3 (2015) 49–54 49 DOI 10.3233/NUA-150050 IOS Press Promising neuroprotective effects of oligostilbenes Hamza Temsamani, Stephanie´ Krisa, Jean-Michel Merillon´ and Tristan Richard∗ Universit´e de Bordeaux, ISVV, EA 3675 GESVAB, 33140 Villenave d’Ornon, France Abstract. Stilbenes (resveratrol derivatives) are a polyphenol class encountered in a large number of specimens in the vegetal realm. They adopt a variety of structures based on their building block: resveratrol. As the most widely studied stilbene to date, resveratrol has shown multiple beneficial effects on multiple diseases and on neurodegenerative diseases. Except for resveratrol, however, the biological activities of stilbenes have received far less attention, even though some of them have shown promising effects on neurodegenerative disease. This review covers the chemistry of stilbenes and offers a wide insight into their neuroprotective effects. Keywords: Resveratrol, stilbene, oligostilbene, neuroprotection 1. Introduction concerning the derivatives of resveratrol and their pro- tective effects on neurodegenerative diseases. Even if “French paradox” [1] is not universally accepted [2], evidences of beneficial effects of wine consumption on health were validated [3–5] and since 2. Polyphenols and stilbenes then has led to a growing interest in polyphenols. Many of these natural secondary metabolites have been Stilbenes constitute a class of phenolic compounds investigated owing to their beneficial effects on human [16, 17]. Polyphenols are mainly synthesized trough health. Indeed, studies have demonstrated a correlation the shikimate pathway and are characterized by at least between moderate wine consumption and a decrease in one hydroxyl group linked to an aromatic cycle. They the risk of cancer, cardiovascular diseases and neurode- can be divided into two groups: flavonoid and non- generative diseases [6].
    [Show full text]
  • Fflc^Cj^^Lljp^ O Sources and Chemistry of Resveratrol
    fflc^cj^^lljp^ O Sources and Chemistry of Resveratrol Navindra P. Seeram University of California, Los Angeles Vishal V. Kulkarni and Subhash Padhye University of Pune, India CONTENTS Introduction 17 Sources of Resveratrol 18 Structure of Resveratrol 22 Chemical Analyses of Resveratrol 23 Synthesis of Resveratrol 24 Theoretical and SAR Studies of Resveratrol 25 Conclusion 26 References 26 INTRODUCTION Stilbenoids are phenol-based plant metabolites widely represented in nature and implicated with human health benefits against problems such as cancer, inflammation, neurodegenerative disease, and heart disease. Among stilbenes, the phytoalexin resveratrol (3,4',5-trihydroxystilbene; Figure 2.1) has attracted immense attention from biologists and chemists due to its numerous biological properties. Resveratrol is a pivotal molecule in plant biology and plays an important role as the parent molecule of oligo­ mers known as the viniferins [1]. It is also found in nature as closely related analogs, derivatives, and conjugates (Table 2.1) [1-80]. In addition, the inherent structural simplicity of the resveratrol molecule allows for the rational design of new chemotherapeutic agents, and hence a number of its synthetic adducts, analogs, derivatives, and conjugates have been reported (Table 2.1) [1-80]. 17 18 Resveratrol in Health and Disease Trans-resveratrol (frans-3,4',5-trihydroxystilbene) C/s-resveratrol (c/s-3,4',5-trihydroxystilbene) FIGURE 2.1 Chemical structures of trans- and r/.v-resveratrol (3.4'. .5-trihydrox- vstilbene). Numerous efforts have been directed to studies of structure-activity relationships (SARs) of resveratrol and its analogs with the goal of increasing and enhancing their //; V/IY; biological potency and bioavailability.
    [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]
  • Vitis Vinifera Canes, a Source of Stilbenoids Against Downy Mildew Tristan Richard, Assia Abdelli-Belhad, Xavier Vitrac, Pierre Waffo-Téguo, Jean-Michel Merillon
    Vitis vinifera canes, a source of stilbenoids against downy mildew Tristan Richard, Assia Abdelli-Belhad, Xavier Vitrac, Pierre Waffo-Téguo, Jean-Michel Merillon To cite this version: Tristan Richard, Assia Abdelli-Belhad, Xavier Vitrac, Pierre Waffo-Téguo, Jean-Michel Merillon. Vitis vinifera canes, a source of stilbenoids against downy mildew. OENO One, Institut des Sciences de la Vi- gne et du Vin (Université de Bordeaux), 2016, 50 (3), pp.137-143. 10.20870/oeno-one.2016.50.3.1178. hal-01602243 HAL Id: hal-01602243 https://hal.archives-ouvertes.fr/hal-01602243 Submitted on 27 May 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. Distributed under a Creative Commons Attribution - NonCommercial| 4.0 International License 01-mérillon_05b-tomazic 13/10/16 13:31 Page137 VITIS VINIFERA CANES, A SOURCE OF STILBENOIDS AGAINST DOWNY MILDEW Tristan RICHARD 1, Assia ABDELLI-BELHADJ 2, Xavier VITRAC 2, Pierre WAFFO TEGUO 1, Jean-Michel MÉRILLON 1, 2* 1: Université de Bordeaux, Unité de Recherche Œnologie EA 4577, USC 1366 INRA, INP Equipe Molécules d’Intérêt Biologique (Gesvab) - Institut des Sciences de la Vigne et du Vin - CS 50008 210, chemin de Leysotte 33882 Villenave d’Ornon Cedex, France 2: Polyphénols Biotech, Institut des Sciences de la Vigne et du Vin - CS 50008 210, chemin de Leysotte 33882 Villenave d’Ornon Cedex, France Abstract Aim: To investigate the antifungal efficacy of grape cane extracts enriched in stilbenes against Plasmopara viticola by in vivo experiments on grape plants.
    [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]
  • 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.
    [Show full text]
  • 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).
    [Show full text]
  • (5)September 2019
    SPECIAL ISSUE VOLUME 12 NUMBER- (5) SEPTEMBER 2019 Print ISSN: 0974-6455 BBRC Online ISSN: 2321-4007 Bioscience Biotechnology CODEN BBRCBA www.bbrc.in Research Communications University Grants Commission (UGC) New Delhi, India Approved Journal Biosc Biotech Res Comm Special Issue Vol 12 (5)September 2019 An International Peer Reviewed Open Access Journal for Rapid Publication Published By: Society For Science and Nature Bhopal, Post Box 78, GPO, 462001 India Indexed by Thomson Reuters, Now Clarivate Analytics USA ISI ESCI SJIF 2019=4.186 Online Content Available: Every 3 Months at www.bbrc.in Registered with the Registrar of Newspapers for India under Reg. No. 498/2007 Bioscience Biotechnology Research Communications SPECIAL ISSUE VOL 12 NO (5) SEP 2019 Food Consumption and It’s Economic Availability in Rural Population 01-06 O.I. Khairullina The Application of Mineral Additives in Different Formulations for Feeding Animals 07-14 L.V. Alekseeva, A.A. Lukianov, P.I. Migulev State Food Security Indicator of Agriculture 15-21 Tatyana M. Yarkova Cassava Peel-specimen Lye-digestion Process Optimization 22-32 G.R. Tsekwi and P.O. Ngoddy The Effectiveness of Concomitant Use of Hmg-Coa Reductase Inhibitors and 33-36 Endothelial Protectors Tatyana A. Denisyuk Innovated Product from Cassava (Manihot Esculenta) and Squid (Loligod Uvauceli) with Different Drying 37-54 Methods and Packaging Materials Aler L. Pagente, MTT E and Sofia C. Naelga, Mahe Ecological Mapping of the Territory on the Basis of Integrated Monitoring 55-66 Nurpeisova M., Bekbassarov
    [Show full text]
  • Mass Spectrometry T ⁎ Raul F
    Food Control 108 (2020) 106821 Contents lists available at ScienceDirect Food Control journal homepage: www.elsevier.com/locate/foodcont A rapid quantification of stilbene content in wine by ultra-high pressure liquid chromatography – Mass spectrometry T ⁎ Raul F. Guerreroa, Josep Valls-Fonayetb, Tristan Richardb, , Emma Cantos-Villara a Instituto de Investigación y Formación Agraria y Pesquera (IFAPA), Centro Rancho de la Merced, Consejería de Agricultura, Pesca y Desarrollo Rural (CAPDA), Junta de Andalucía. Ctra. Trebujena, Km 2.1, 11471, Jerez de la Frontera, Spain b Univ. Bordeaux, ISVV, EA 4577, USC 1366 INRA, Unité de Recherche Œnologie, Molécules d’Intérêt Biologique, 210 chemin de Leysotte, F-33882, Villenave d'Ornon, France ARTICLE INFO ABSTRACT Keywords: Stilbenes are a family of bioactive phenolic compounds. Wine is one of the main sources of stilbenes in diet. Very Stilbene few studies have dealt with a detailed quantitative analysis of stilbenes in wine. Most methodologies reported Viniferin until now have been restricted to the analysis of few stilbenes such as resveratrol and piceid. In this study, a Wine method for the quantification of wine stilbenes has been developed and validated. The method was simple, fast Mass spectrometry and sensitive with LOD between 4 and 28 μg/L. Matrix effects were assessed, and the methodology was validated in terms of precision, accuracy, linearity and repetitiveness. The method was able to quantify, in less than 5 min, fifteen targeted stilbenes in wines including seven monomers, three dimers, one trimer, and four tetramers. The methodology was applied to white and red wines. E-piceid was the main stilbene in white wine (mean 155 μg/L).
    [Show full text]