DOCSLIB.ORG

Anti-Inflammatory Effect of Oligostilbenoids from Vitis Heyneana in LPS-Stimulated RAW 264.7 Macrophages Via Suppressing the NF-Kappa B Activation

Total Page：16

File Type：pdf, Size：1020Kb

Download full-text PDF Read full-text
Anti-Inflammatory Effect of Oligostilbenoids from Vitis Heyneana in LPS-Stimulated RAW 264.7 Macrophages Via Suppressing the NF-Kappa B Activation Anti-inflammatory effect of oligostilbenoids from Vitis heyneana in LPS-stimulated RAW 264.7 macrophages via suppressing the NF-kappa B activation Do Thi Ha; Phung Thanh Long; Tran Thi Hien; Tuan, Dao Trong; Nguyen Thi Thuy An; Nguyen Minh Khoi; Ha Van Oanh; Tran Manh Hung Published in: Chemistry Central Journal DOI: 10.1186/s13065-018-0386-5 Publication date: 2018 Document version Publisher's PDF, also known as Version of record Citation for published version (APA): Do Thi Ha, Phung Thanh Long, Tran Thi Hien, Tuan, D. T., Nguyen Thi Thuy An, Nguyen Minh Khoi, Ha Van Oanh, & Tran Manh Hung (2018). Anti-inflammatory effect of oligostilbenoids from Vitis heyneana in LPS- stimulated RAW 264.7 macrophages via suppressing the NF-kappa B activation. Chemistry Central Journal, 12(1), 1-9. [14]. https://doi.org/10.1186/s13065-018-0386-5 Download date: 26. Sep. 2021 Ha et al. Chemistry Central Journal (2018) 12:14 https://doi.org/10.1186/s13065-018-0386-5 RESEARCH ARTICLE Open Access Anti‑infammatory efect of oligostilbenoids from Vitis heyneana in LPS‑stimulated RAW 264.7 macrophages via suppressing the NF‑κB activation Do Thi Ha1*, Phung Thanh Long1, Tran Thi Hien2,3, Dao Trong Tuan4, Nguyen Thi Thuy An1,5, Nguyen Minh Khoi1, Ha Van Oanh6 and Tran Manh Hung7* Abstract Background: Vitis heyneana is widely distributed in the north of Vietnam, it has been used in Vietnamese traditional medicine as an agent for treatment of arthritis, bronchitis, carbuncles and infammatory conditions, and menstrual irregularities. However, this plant has not been investigated in phytochemical constituents and biological efects, especially in the anti-infammatory property. Results: Bioassay-guided fractionation of the EtOAc soluble fraction from the aerial part of Vitis heyneana resulted in the isolation of a series of oligostilbenoids as piceid (1), 2-r-viniferin (2), betulifol A (3), vitisinol C (4), (-)-trans-ε-viniferin (5), α-viniferin (6), shoreaketon (7), amurensin B (8), vitisinol B (9), and cis-vitisin B (10). Compound 5 showed the most potent inhibitory activities by suppressing LPS-induced COX-2 expression and PGE2 production. This compound exhibited signifcantly reduced LPS-induced nitric oxide (NO) release in a dose-dependent manner. These efects are accompanied with the inhibition of transcription factor NF-κB activation. Conclusion: The results suggested that trans-ε-viniferin exerts anti-infammatory efects via suppression the NF-κB activation in RAW 264.7 cells. Keywords: Vitis heyneana, (-)-Trans-ε-viniferin, COX-2, PGE2, NO, NF-κB Background resveratrol named stilbenoids [3–7]. To date, over 1000 Te genus Vitis (family Vitaceae) is in the major group stilbenoids have been identifed in various plant families with more than 66 species identifed and is distrib- such as Celastraceae, Cyperaceae, Fabaceae, Iritaceae, uted throughout the world [1]. In Vietnam, 6 species Moraceae, Paeoniaceae, and Vitaceae. Te Vitaceae of Vitis genus have been reported until now, including family includes about 900 species within 14–17 gen- V. larbusca L., V. heyneana Roem, & Schult., V. retordii era, primarily in tropical climate [8, 9]. Of these genera, Roman du Caill. Ex Planch. V. vinifera L., V. balansana only fve, the Ampelopsis, Cissus, Cyphostemma, Par- Planch., V. fexuosa Tunb [2]. Typical constituents thenocissus, and Vitis genera reported the presence of in Vitis genus have been reported to be oligomers of stilbenoids. However, chemical constituents of the spe- cies in Vitis genus have been studied the most. Stilbe- noids possessed various pharmacological activities such *Correspondence: [email protected]; [email protected] as antioxidative, anti-infammatory, and antimicrobial 1 Vietnam National Institute of Medicinal Materials, 3B Quangtrung, Hanoi, Vietnam activities, as well as having cardioprotective, hepatopro- 7 Department of Biomedical Sciences, Institute for Research and Executive tective, and neuroprotective efects [10–14]. Although Education (VNUK), The University of Danang, 41 Le Duan, Haichau district, approximately 100 stilbenoid monomers, dimers, and Danang 551000, Vietnam Full list of author information is available at the end of the article oligomers have been found in all Vitis species, research © The Author(s) 2018. This article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made. The Creative Commons Public Domain Dedication waiver (http://creativecommons.org/ publicdomain/zero/1.0/) applies to the data made available in this article, unless otherwise stated. Ha et al. Chemistry Central Journal (2018) 12:14 Page 2 of 9 on the chemical compositions and biological activities of Vitis genus remains lacking [15]. Our screening anti- infammatory efect of an ethanol extract of 4 Vitis spe- cies including V. heyneana Roem. & Schult. (VH), Vitis vinifera L. (VV); Vitis balansana Planch. (VB), and Vitis labrusca L. (VL) collected in Vietnam via suppression of LPS-induced COX-2 expression found that 96% of ethanol extract of VH exhibited the most activity [16]. Besides, V. heyneana is widely distributed in northern Vietnam, for example in Cao Bang, Lang Son, and Lao Cai provinces. Te stems and roots of this species are traditionally used for the treatment of arthritis, bron- chitis, carbuncles and infammatory conditions, and menstrual irregularities in Vietnamese indigenous peo- ples [17]. So far, few studies have been done to investi- Fig. 1 COX-2 expression efects of V. heyneana extract (VH) and its gate the chemical constituents of VH. Currently, only a fractions (VHH: n-hexane, VHE: ethyl acetate, VHW: water fraction; all 50 µg/mL). Eighteen hours after treating cells with LPS (5 µg/mL) with few studies have referred to the presence of stilbenoids or without fractions in RAW 264.7 cells. Samples were harvested and in VH [17–19]. However, evaluation of anti-infamma- lysated for COX-2 mRNA level by qPCR. Relative changes in the COX-2 tory activities of the VH species have not been studied mRNA expression (*signifcant as compared to control, *, p < 0.05; yet. Tis study reports the anti-infammatory efects of **, p < 0.01; ***, p < 0.001; #signifcant as compared to LPS group, n 4–5) VH extracts and its isolated oligostilbenoids via sup- = pressing LPS-induced COX-2 expression, PGE2 and NO productions, and NF-κB activation in RAW 264.7 macrophages. Screening inhibitory activities of oligostilbenoids by suppressing LPS‑induced COX‑2 expression and PGE2 Results and discussion production in RAW 264.7 macrophages Screening inhibitory activities Te efects of all isolated compounds at concentration To study the cytotoxic efects of extract and its fractions of 10 µM, and a reference agent, meloxicam (20 µM) on cell viability, the RAW 264.7 cells were incubated were further examined on LPS-induced COX-2 protein, and treated a concentration of all materials (50 µg/mL). mRNA expression and LPS-induced PGE2 production in Te results showed that all the extract and fractions that RAW 246.7 cells by reported method with slight modif- induced cell toxicities were negligible at the above con- cation. As the results in Fig. 3, western blotting and real centrations [16]. In order to examine candidate extract/ time-PCR assays revealed that, among the active metabo- fractions inhibiting COX-2 in RAW 264.7 cells, ethanol lites, trans-ε-viniferin (5; 10 µM) potently suppressed V. heyneana extract (VH) and its fractions (n-hexane- LPS-induced COX-2 expression in RAW 246.7 cells VHH, ethyl acetate-VHE and water-VHW) were tested (Fig. 3a, b). Furthermore, ELISA assay confrmed that 5 on COX-2 mRNA expression level by qPCR. As shown in most inhibited the level of LPS-induced PGE2 produc- Fig. 1, the inhibitory efect of COX-2 mRNA was mostly tion in RAW 264.7 cells (Fig. 3c). potently suppressed by VHE and VH. Efects of 5 on COX‑2, iNOS expression and PGE2 Structure identifcation of the isolated compounds production in RAW 264.7 macrophages To investigate the active components from the poten- Considering that the 5 was the most active metabolite, tial fraction, several chromatographic techniques were the efects of this compound was investigated on LPS- applied and ten compounds were obtained after puri- induced PGE2 production in RAW 264.7 cells using fcation. On the basis of NMR spectroscopic analysis, ELISA method with slight modifcation. As the results in and in comparison with the previous studies, the chemi- Fig. 4a show, stimulation of cells resulted in the increase cal structures of these compounds were identifed as of PGE2 production compared with unstimulated vehi- piceid (1), 2-r-viniferin (2), betulifol A (3), vitisinol C cle cells. In the administration of 5 (1–30 µM), the PGE2 (4), (-)-trans-ε-viniferin (5), α-viniferin (6), shoreaketon productions were remarkably reduced in a concentra- (7), amurensin B (8), vitisinol B (9), and cis-vitisin B (10) tion dependent manner (p < 0.05). We further investi- (Fig. 2) [17, 20–26]. gated whether the inhibition efect by the same range of concentration of 5 was related to the gene expression, Ha et al. Chemistry Central Journal (2018) 12:14 Page 3 of 9 4 HO O 11' OH 1 O 11' OH OH 3' 13' 7 6'' 2' OH H 13' 4'' 1 7 10' 5'' O Ha 4' 8 H HO 8 10' 2 1' 9' H O 1 HO H 9 9' HO 2'' 3 5' 4 H
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]
  • 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.
    [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]
  • LIMA SENYAWA FENOLIK DARI KULIT KAYU Dipterocarpus Elongatus (DIPTEROCARPACEAE) DAN SIFAT SITOTOKSIKNYA TERHADAP SEL MURIN LEUKEMIA P-388
    LIMA SENYAWA FENOLIK DARI KULIT KAYU Dipterocarpus elongatus (DIPTEROCARPACEAE) DAN SIFAT SITOTOKSIKNYA TERHADAP SEL MURIN LEUKEMIA P-388 Muhtadi,1∗) Euis H. Hakim,2) Yana M. Syah,2) Lia D. Juliawaty,2) Sjamsul A. Achmad,2) dan Jalifah Latip3) 1) Fakultas Farmasi, Universitas Muhammadiyah Surakarta, Jalan A. Yani Tromol Pos I Pabelan Kartasura, Surakarta 57102, Indonesia 2) Kelompok Penelitian Kimia Organik Bahan Alam, Departemen Kimia, Institut Teknologi Bandung, Jalan Ganeca 10 Bandung 40132, Indonesia 3) School of Chemical Sciences & Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor D.E., Malaysia ABSTRAK Lima senyawa fenolik, yaitu (-)-laevifonol (1), (-)-α-viniferin (2), (-)-vatikanol A (3), bergenin (4) dan 4’- O-metilgalokatecin (5), telah berhasil diisolasi dari ekstrak aseton kulit batang Dipterocarpus elongatus. Struktur molekul senyawa-senyawa tersebut ditetapkan berdasarkan data spektroskopi UV, IR, 1H NMR dan 13C NMR serta perbandingan dengan data sejenis yang telah dilaporkan. Pengujian aktivitas sitotoksik terhadap sel murin leukemia P-388 dilakukan dengan metode MTT assay. Hasil pengujian aktivitas sitotoksik dari masing-masing senyawa menunjukkan nilai IC50 berturut-turut sebesar >100; 17,5; 27,0; >100 dan 70,0 µg/ml. Kata kunci : Senyawa fenolik, sitotoksik, sel murin P-388, Dipterocarpus elongatus, Dipterocarpaceae ABSTRACT Five phenolic compounds; i.e. (-)-laevifonol, (-)-α-viniferin, (-)-vaticanol A, bergenin and 4’-O- methylgallocathecin were isolated from acetone extracts of the stem bark of Dipterocarpus elongatus. The structure of the isolates were established based on spectroscopic evidence; UV, IR, 1H NMR, 13C NMR, and by comparison with the standard compounds. The cytotoxic activities of these compounds were evaluated against murine leukaemia P-388 cells with MTT assay.
    [Show full text]
  • Docteur De L'université De Bordeaux
    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. Alain DECENDIT Maître de Conférences, Université de Bordeaux Directeur de thèse M. Tristan RICHARD Professeur, Université de Bordeaux Membre invité Mme. Stéphanie KRISA Maître de Conférences, Université de Bordeaux Membre invité Extraction et hémisynthèse des stilbènes de la vigne et du vin pour une application en santé humaine et végétale Les stilbènes sont des molécules de défense que produit la vigne pour lutter contre les agents pathogènes. Retrouvés dans le vin, ils acquièrent une valeur ajoutée pour leurs effets bénéfiques avérés en santé humaine. Sachant que l’efficacité des stilbènes contre certains oomycètes et champignons qui infectent la vigne augmente avec leur degré d’oligomérisation, cette thèse avait pour premier objectif d’optimiser et de procéder à des réactions de couplage oxydatif du resvératrol et de l’ɛ-viniférine extraits de sarments de vigne, en présence de sels de métaux, pour la production d’oligomères. Ces réactions d’hémisynthèse ont conduit d’une part à la formation de stilbènes à haut poids moléculaire, et à la production d’extraits à forte activité antifongique contre deux agents pathogènes majeurs de la vigne, Plasmopara viticola et Botrytis cinerea.
    [Show full text]
  • Anti-Inflammatory Effect of Oligostilbenoids
    Ha et al. Chemistry Central Journal (2018) 12:14 https://doi.org/10.1186/s13065-018-0386-5 RESEARCH ARTICLE Open Access Anti‑infammatory efect of oligostilbenoids from Vitis heyneana in LPS‑stimulated RAW 264.7 macrophages via suppressing the NF‑κB activation Do Thi Ha1*, Phung Thanh Long1, Tran Thi Hien2,3, Dao Trong Tuan4, Nguyen Thi Thuy An1,5, Nguyen Minh Khoi1, Ha Van Oanh6 and Tran Manh Hung7* Abstract Background: Vitis heyneana is widely distributed in the north of Vietnam, it has been used in Vietnamese traditional medicine as an agent for treatment of arthritis, bronchitis, carbuncles and infammatory conditions, and menstrual irregularities. However, this plant has not been investigated in phytochemical constituents and biological efects, especially in the anti-infammatory property. Results: Bioassay-guided fractionation of the EtOAc soluble fraction from the aerial part of Vitis heyneana resulted in the isolation of a series of oligostilbenoids as piceid (1), 2-r-viniferin (2), betulifol A (3), vitisinol C (4), (-)-trans-ε-viniferin (5), α-viniferin (6), shoreaketon (7), amurensin B (8), vitisinol B (9), and cis-vitisin B (10). Compound 5 showed the most potent inhibitory activities by suppressing LPS-induced COX-2 expression and PGE2 production. This compound exhibited signifcantly reduced LPS-induced nitric oxide (NO) release in a dose-dependent manner. These efects are accompanied with the inhibition of transcription factor NF-κB activation. Conclusion: The results suggested that trans-ε-viniferin exerts anti-infammatory efects via suppression the NF-κB activation in RAW 264.7 cells. Keywords: Vitis heyneana, (-)-Trans-ε-viniferin, COX-2, PGE2, NO, NF-κB Background resveratrol named stilbenoids [3–7].
    [Show full text]
  • STILBENOID CHEMISTRY from WINE and the GENUS VITIS, a REVIEW Alison D
    06àutiliser-mérillonbis_05b-tomazic 27/06/12 21:23 Page57 STILBENOID CHEMISTRY FROM WINE AND THE GENUS VITIS, A REVIEW Alison D. PAWLUS, Pierre WAFFO-TÉGUO, Jonah SHAVER and Jean-Michel MÉRILLON* GESVAB (EA 3675), Université de Bordeaux, ISVV Bordeaux - Aquitaine, 210 chemin de Leysotte, CS 50008, 33882 Villenave d'Ornon cedex, France Abstract Résumé Stilbenoids are of great interest on account of their many promising Les stilbénoïdes présentent un grand intérêt en raison de leurs nombreuses biological activities, especially in regards to prevention and potential activités biologiques prometteuses, en particulier dans la prévention et le treatment of many chronic diseases associated with aging. The simple traitement de diverses maladies chroniques liées au vieillissement. Le stilbenoid monomer, -resveratrol, has received the most attention due to -resvératrol, monomère stilbénique, a suscité beaucoup d'intérêt de par E E early and biological activities in anti-aging assays. Since ses activités biologiques et . Une des principales sources in vitro in vivo in vitro in vivo , primarily in the form of wine, is a major dietary source of alimentaires en stilbénoïdes est , principalement sous forme Vitis vinifera Vitis vinifera these compounds, there is a tremendous amount of research on resveratrol de vin. De nombreux travaux de recherche ont été menés sur le resvératrol in wine and grapes. Relatively few biological studies have been performed dans le vin et le raisin. À ce jour, relativement peu d'études ont été réalisées on other stilbenoids from , primarily due to the lack of commercial sur les stilbènes du genre autre que le resvératrol, principalement en Vitis Vitis sources of many of these compounds.
    [Show full text]
  • 1 TIN TỨC SỰ KIỆN Nghiên Cứu Khoa Học Của Học Sinh Lớp 12 Được Công
    TRUNG TÂM THÔNG TIN - ỨNG DỤNG TIẾN BỘ KHOA HỌC VÀ CÔNG NGHỆ THÔNG TIN PHỤC VỤ QUẢN LÝ NHÀ NHƯỚC VỀ KHOA HỌC VÀ CÔNG NGHỆ BẢN TIN CHỌN LỌC SỐ 07-2020 (09/3/2020 – 15/3/2020) MỤC LỤC TIN TỨC SỰ KIỆN 2 Nghiên cứu khoa học của học sinh lớp 12 được công bố 2 trên tạp chí thuộc danh mục ISI Samsung bắt đầu xây trung tâm R&D 220 triệu USD tại 4 Việt Nam Ứng dụng KH&CN trong cơ giới hóa và chế biến nông 8 nghiệp: Làm sao để đồng bộ? KHOA HỌC VÀ CÔNG NGHỆ THẾ GIỚI 10 Khung kim loại hữu cơ vẫn tách khí dù có sự xuất hiện của 10 nước Hóa thạch biển giúp các nhà khoa học nghiên cứu nóng lên 12 toàn cầu thời xa xưa Vật liệu nano từ đồng có thể tiêu diệt tế bào ung thư ở 14 chuột Miếng vá tim làm bằng polyme dẫn điện có khả năng phục 16 hồi tổn thương tim Công cụ dựa trên kỹ thuật CRISPR mới có thể dò và kiểm 17 soát một số mạch di truyền cùng một lúc KHOA HỌC VÀ CÔNG NGHỆ TRONG NƯỚC 19 Nghiên cứu đặc trưng vật lý của quá trình mất mát vật chất 19 từ sao siêu khổng lồ Nghiên cứu cơ chế tác dụng chống viêm của một số hợp 21 chất oligostilbenoid phân lập từ các loài Nho dại (Vitis sp.) thu hái ở miền Bắc Việt Nam 1 TIN TỨC SỰ KIỆN Nghiên cứu khoa học của học sinh lớp 12 được công bố trên tạp chí thuộc danh mục ISI Học sinh Đào Ngọc Minh Khuê.
    [Show full text]
  • A-VINIFERIN, SUATU TRIMER STILBENOID DARI KULIT BATANG
    107 Advances in Natural and Applied Sciences, 3(1): 107-112, 2009 ISSN 1995-0748 © 2009, A merican Euras ian Network for Scientific Information T his is a refereed journal and all articles are professionally screened and reviewed ORIGINAL ARTICLE The Isolation of Hopeaphenol, a Tetramer Stilbene, from Shorea ovalis Blume Sutopo Hadi and Noviany Department of Chemistry, University of Lampung, Bandar Lampung 35145 Indonesia Sutopo Hadi and Noviany: The Is olation of Hopeaphenol, a Tetramer Stilbene, from Shorea ovalis Blume: Adv. in Nat. Appl. Sci., 3(1): 107-112, 2009 ABSTRACT Hopeaphenol, a tetramer s tilbene, one of the derivatives of oligomeric s tilbene compounds was s ucces s fully isolated and identified from acetone extract of stem bark of Shorea ovalis Blume (Dipterocarpaceae). The isolation of this tetramer stilbene from this Shorea plant has never been done previous ly. The purification methods included extraction, partition, and fractionation with vacuum liquid chromatography and then followed by gravity column chromatography. The structure of the compound isolated was determined based on the analys es of phys ical data, UV and IR s pectros copies and compared to the s tandard compound of hopeaphenol. Key words : Hopeaphenol, Dipterocarpaceae, S. ovalis Blume Introduction Indonesia, the second richest country in the biological diversity after Brazil, is a top country in the tropical forest. However, with this abundant resource, it has, so far, not been fully investigated, although the presence of the tropical forest as the natural resources of chemical substances is invaluable and potentially to be much more developed (Achmad, 1995) The family pla n t o f D ipterocarpaceae is one of the biological divers ities of Indones ian plants and it is widely dis tributed in all parts of Indones ia.
    [Show full text]
  • Inhibition of Pancreatic Α-Amylase by Resveratrol Derivatives: Biological Activity and Molecular Modelling Evidence for Cooperativity Between Viniferin Enantiomers
    molecules Article Inhibition of Pancreatic α-amylase by Resveratrol Derivatives: Biological Activity and Molecular Modelling Evidence for Cooperativity between Viniferin Enantiomers Luce M. Mattio 1 , Mauro Marengo 1, Chiara Parravicini 2, Ivano Eberini 2, Sabrina Dallavalle 1, Francesco Bonomi 1, Stefania Iametti 1 and Andrea Pinto 1,* 1 Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, Via Celoria 2, 20133 Milano, Italy 2 Department of Pharmacological and Biomolecular Sciences (DiSFeB) & cDSRC, University of Milan, Via Balzaretti 9, 20133 Milano, Italy * Correspondence: [email protected]; Tel.: +39-02-50316814 Received: 6 August 2019; Accepted: 2 September 2019; Published: 5 September 2019 Abstract: To improve the current understanding of the role of stilbenoids in the management of diabetes, the inhibition of the pancreatic α-amylase by resveratrol derivatives was investigated. To approach in a systematic way, the mechanistic and structural aspects of the interaction, potential bioactive agents were prepared as single molecules, that were used for the biological evaluation of the determinants of inhibitory binding. Some dimeric stilbenoids—in particular, viniferin isomers— were found to be better than the reference drug acarbose in inhibiting the pancreatic α-amylase. Racemic mixtures of viniferins were more effective inhibitors than the respective isolated pure enantiomers at an equivalent total concentration, and displayed cooperative effects not observed with the individual enantiomers. The molecular docking analysis provided a thermodynamics-based rationale for the measured inhibitory ability and for the observed synergistic effects. Indeed, the binding of additional ligands on the surface of the alpha-amylase was found to decrease the dissociation constant of inhibitors bound to the active site of the enzyme, thus providing a mechanistic rationale for the observed inhibitory synergies.
    [Show full text]
  • And Dehydro-Ε-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria Monocytogenes
    International Journal of Molecular Sciences Article Structural Requirements of Benzofuran Derivatives Dehydro-δ- and Dehydro-"-Viniferin for Antimicrobial Activity Against the Foodborne Pathogen Listeria monocytogenes Giorgia Catinella 1, Luce M. Mattio 1 , Loana Musso 1, Stefania Arioli 1 , Diego Mora 1 , Giovanni Luca Beretta 2 , Nadia Zaffaroni 2 , Andrea Pinto 1,* and Sabrina Dallavalle 1 1 Department of Food, Environmental and Nutritional Sciences (DeFENS), University of Milan, Via Celoria 2, 20133 Milan, Italy; [email protected] (G.C.); [email protected] (L.M.M.); [email protected] (L.M.); [email protected] (S.A.); [email protected] (D.M.); [email protected] (S.D.) 2 Molecular Pharmacology Unit, Department of Applied Research and Technological Development, Fondazione IRCCS Istituto Nazionale Tumori, Via Amadeo 42, 20133 Milan, Italy; [email protected] (G.L.B.); nadia.zaff[email protected] (N.Z.) * Correspondence: [email protected] Received: 15 February 2020; Accepted: 19 March 2020; Published: 21 March 2020 Abstract: In a recent study,we investigated the antimicrobial activity of a collection of resveratrol-derived monomers and dimers against a series of foodborne pathogens. Out of the tested molecules, dehydro-δ-viniferin and dehydro-"-viniferin emerged as the most promising derivatives. To define the structural elements essential to the antimicrobial activity against the foodborne pathogen L. monocytogenes Scott A as a model Gram-positive microorganism, the synthesis of a series of simplified benzofuran-containing derivatives was carried out. The systematic removal of the aromatic moieties of the parent molecules allowed a deeper insight into the most relevant structural features affecting the activity.
    [Show full text]