107 results on '"Mérillon JM"'
Search Results
2. Glucosyloxybenzyl derivatives of (R)-2-Benzylmalic acid from the aerial parts of Arundina graminifolia (D.Don) Hochr. (Orchidaceae)
- Author
-
Auberon, F, additional, Antheaume, C, additional, Krisa, S, additional, Bonté, F, additional, Mérillon, JM, additional, and Lobstein, A, additional
- Published
- 2016
- Full Text
- View/download PDF
3. Purification of novel stilbene oligomers from vine stalks by centrifugal partition chromatography guided by mass spectrometry
- Author
-
Papastamoulis, Y, primary, Waffo-Téguo, P, additional, Richard, T, additional, Zga, N, additional, Schmitter, JM, additional, and Mérillon, JM, additional
- Published
- 2008
- Full Text
- View/download PDF
4. Purification of hydroxystilbenes from vine stalks cv. Chardonnay by centrifugal partition chromatography
- Author
-
Zga, N, primary, Waffo-Téguo, P, additional, Papastamoulis, Y, additional, Toribio, A, additional, Richard, T, additional, Renault, JH, additional, Monti, JP, additional, and Mérillon, JM, additional
- Published
- 2008
- Full Text
- View/download PDF
5. Resveratrol oligomers from Vitis Vinifera L. stems
- Author
-
Amira-Guebailia, H, primary, Richard, T, additional, Rouaiguia, S, additional, Waffo Tueguo, P, additional, Delaunay, JC, additional, and Mérillon, JM, additional
- Published
- 2007
- Full Text
- View/download PDF
6. Radiolabelled cyanidin 3-O-glucoside is poorly absorbed in the mouse.
- Author
-
Felgines C, Krisa S, Mauray A, Besson C, Lamaison JL, Scalbert A, Mérillon JM, and Texier O
- Published
- 2010
- Full Text
- View/download PDF
7. Immobilized yeast cells and secondary metabolites
- Author
-
Verica Djordjevic, Viktor Nedović, Brian Gibson, Ronnie Willaert, Mérillon , JM., and Ramawat, K.
- Subjects
0106 biological sciences ,Higher alcohols ,0303 health sciences ,Chemistry ,Esters ,01 natural sciences ,Yeast ,03 medical and health sciences ,Bioproduction ,Carbonyl compounds ,Biochemistry ,010608 biotechnology ,Fermentation ,Fatty acids ,030304 developmental biology - Abstract
The use of immobilized cell technology (ICT) is viewed as a promising biotechnological tool to achieve high volumetric productivities of yeast fermentation in bioindustry of alcoholic beverages. During this process a huge number of organic compounds are being formed as yeast secondary metabolites, among which volatile compounds, such as higher alcohols, esters, and vicinal diketones, are the most important flavoring compounds. The objective of this chapter is to summarize the knowledge on the origin of the flavor-active and nonvolatile compounds synthesized by yeast and to describe how the composition of the medium, culture strain, process conditions (temperature, aeration, etc.), bioreactor design, and other critical parameters influence the metabolic activities of yeast cultures. Despite the technological and economic advantages provided by ICT, commercialization of this technology experienced only limited success, mainly due to unpredictable effect of immobilization on yeast physiology. This chapter is an attempt to rationalize and make some conclusions about the impact of cell immobilization on yeast metabolism collected from empirical experiences in production of alcoholic beverages. The knowledge addressing this issue may be of particular benefit to the nascent bioflavor industry.
- Published
- 2017
8. Isolation of Hydrolyzable Tannins from Castanea sativa Using Centrifugal Partition Chromatography.
- Author
-
Métoyer B, Renouf E, Jourdes M, Mérillon JM, and Téguo PW
- Subjects
- Molecular Structure, Wood chemistry, Plant Extracts chemistry, Hydrolyzable Tannins chemistry, Hydrolyzable Tannins isolation & purification, Fagaceae chemistry
- Abstract
Castanea sativa wood is a rich source of hydrolyzable tannins, known for their diverse bioactivities. To investigate these bioactive properties further, it is crucial to isolate and characterize hydrophilic compounds effectively. To address this issue, we developed a centrifugal partition chromatography (CPC) method and applied it to an aqueous C. sativa wood extract. We determined the partition coefficients ( K
D ) of the six major compounds using four butanol-/water-based biphasic solvent systems. Initially, we utilized the n -butanol/propanol/water (3:1:4, v/v/v) systems for the first fractionation step. Subsequently, we employed the water/methyl tert -butyl ether/butanol/acetone (8:5:3:4, v/v/v/v) system to fractionate moderately and highly hydrophilic fractions. We calculated the KD values for major compounds of the most hydrophilic fractions using the butanol/ethanol/water (4:1:5, v/v/v) and butanol/isopropanol/water (2:1:3, v/v/v) systems. In total, we isolated 23 compounds through a combination of CPC, size exclusion chromatography, and preparative HPLC. Among these compounds, six have never been previously described. We characterized them by 1D and 2D NMR experiments and high-resolution mass spectroscopy acquisitions.- Published
- 2024
- Full Text
- View/download PDF
9. Chiral analysis of E-ε-viniferin enantiomers, towards a new chemotaxonomic marker of the vine.
- Author
-
Gabaston J, Buffeteau T, Irvine AD, Gambetta G, Mérillon JM, and Waffo-Téguo P
- Subjects
- Stilbenes analysis, Vitis chemistry, Wine analysis, Benzofurans analysis
- Abstract
Background: The accurate characterization of grapevine cultivars (Vitis vinifera) is crucial for grape growers, winemakers, wine sellers, consumers and authorities, considering that mistakes could involve significant damage to the wine economic system. To avoid any misunderstanding, morphological, molecular and chemical tools are developed to positively identify grape varieties., Results: E-ε-viniferin is a stilbene dimer mainly present in the woody part of grapevine and present as a mixture of two enantiomers: (7aR, 8aR)-(-)-E-ε-viniferin (1) and (7aS, 8aS)-(+)-E-ε-viniferin (2). In addition to phenotypic and genotypic approaches, a chemotaxonomic method using E-ε-viniferin enantiomers as chemical markers of grapevine cultivars was investigated. The isolation and purification of E-ε-viniferin enantiomers by preparative high-performance liquid chromatography (HPLC) and chiral HPLC from 14 red and eight white grapevine cane cultivars enabled us to determine the proportion of each enantiomer and therefore to calculate the enantiomeric excess for each variety. The relative abundance of each E-ε-viniferin enantiomer permitted us to distinguish grape varieties, as well as to establish cultivar relationships and patterns through statistical analysis., Conclusion: This pioneering work highlighting the enantiomeric excess of E-ε-viniferin as a chemical marker of grapevine paves the way for further studies to understand what mechanisms are involved in the production of these enantiomers in grapevine. © 2023 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry., (© 2023 The Authors. Journal of The Science of Food and Agriculture published by John Wiley & Sons Ltd on behalf of Society of Chemical Industry.)
- Published
- 2023
- Full Text
- View/download PDF
10. Arundinosides I-IX and graminifolosides A-B: 2R-benzylmalate and 2R-isobutylmalates derivatives from Arundina graminifolia (D.Don) Hochr. with antioxidant, cytocompatibility and cytoprotective properties.
- Author
-
Auberon F, Olatunji OJ, Waffo-Teguo P, Olatunde OO, Singh S, Bonté F, Mérillon JM, and Lobstein A
- Subjects
- Antioxidants pharmacology, Molecular Structure, Magnetic Resonance Spectroscopy, Antineoplastic Agents, Orchidaceae chemistry
- Abstract
Phytochemical investigation of the underground parts of Arundina graminifolia D.Don Hochr was conducted leading to the isolation of nine new glucosyloxybenzyl 2R-benzylmalate and two new glucosyloxybenzyl 2R-isobutylmalate derivatives. The compounds were purified using chromatographic techniques and their structures were deduced based on spectroscopic techniques including nuclear magnetic resonance and high-resolution mass spectrometry as well as comparing with previous literature. The antioxidant activities of the isolated compounds were also evaluated. The compounds showed potent antioxidant activities in the ABTS radical scavenging, DPPH radical scavenging and FRAP activities. Furthermore, the isolated compounds were observed to exert minimal cytotoxic effects against RAW 264.7 cell, suggesting biocompatibility as well as cytoprotective effects against hydrogen peroxide induced cell toxicity., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier Ltd. All rights reserved.)
- Published
- 2023
- Full Text
- View/download PDF
11. Chiroptical and potential in vitro anti-inflammatory properties of viniferin stereoisomers from grapevine (Vitis vinifera L.).
- Author
-
Buffeteau G, Hornedo-Ortega R, Gabaston J, Daugey N, Palos-Pinto A, Thienpont A, Brotin T, Mérillon JM, Buffeteau T, and Waffo-Teguo P
- Subjects
- Anti-Inflammatory Agents analysis, Anti-Inflammatory Agents pharmacology, Stereoisomerism, Stilbenes chemistry, Vitis chemistry, Wine analysis
- Abstract
Determination of stereochemistry and enantiomeric excess in chiral natural molecules is a research of great interest because enantiomers can exhibit different biological activities. Viniferin stilbene dimers are natural molecules present in grape berries and wine but also, in larger amount, in stalks of grapevine. Four stereoisomers of viniferin stilbene dimers (7aS,8aS)-E-ε-viniferin (1a), (7aR,8aR)-E-ε-viniferin (1b), (7aS,8aR)-E-ω-viniferin (2a), and (7aR,8aS)-E-ω-viniferin (2b) were isolated from grapevine stalks of Cabernet Sauvignon, Merlot and Sauvignon Blanc, using a combination of centrifugal partition chromatography (CPC), preparative and chiral HPLC. The structure elucidation of these molecules was achieved by NMR whereas the absolute configurations of the four stereoisomers were investigated by vibrational circular dichroism spectroscopy in combination with density functional theory (DFT) calculations. This study unambiguously established the (+)-(7aS,8aS) and (+)-(7aR,8aS) configurations for E-ε-viniferin and E-ω-viniferin, respectively. Finally, we show that Cabernet Sauvignon provided the quasi enantiopure (+)-(7aS,8aS)-E-ε-viniferin compound which presents the best anti-inflammatory and anti-oxidant activities., (Copyright © 2022 Elsevier Ltd. All rights reserved.)
- Published
- 2022
- Full Text
- View/download PDF
12. Anthocyanins Promote Learning through Modulation of Synaptic Plasticity Related Proteins in an Animal Model of Ageing.
- Author
-
Vauzour D, Rendeiro C, D'Amato A, Waffo-Téguo P, Richard T, Mérillon JM, Pontifex MG, Connell E, Müller M, Butler LT, Williams CM, and Spencer JPE
- Abstract
Anthocyanin-rich foods, such as berries, reportedly ameliorate age-related cognitive deficits in both animals and humans. Despite this, investigation into the mechanisms which underpin anthocyanin-mediated learning and memory benefits remains relatively limited. The present study investigates the effects of anthocyanin intake on a spatial working memory paradigm, assessed via the cross-maze apparatus, and relates behavioural test performance to underlying molecular mechanisms. Six-week supplementation with pure anthocyanins (2% w / w ), administered throughout the learning phase of the task, improved both spatial and psychomotor performances in aged rats. Behavioural outputs were accompanied by changes in the expression profile of key proteins integral to synaptic function/maintenance, with upregulation of dystrophin, protein kinase B (PKB/Akt) and tyrosine hydroxylase, and downregulation of apoptotic proteins B-cell lymphoma-extra-large (Bcl-xL) and the phosphorylated rapidly accelerated fibrosarcoma (p-Raf). Separate immunoblot analysis supported these observations, indicating increased activation of extracellular signal-related kinase (ERK1), Akt Ser473, mammalian target of rapamycin (mTOR) Ser2448, activity-regulated cytoskeleton-associated protein (Arc/Arg 3.1) and brain-derived neurotrophic factor (BDNF) in response to anthocyanin treatment, whilst α-E-catenin, c-Jun N-terminal kinase (JNK1) and p38 protein levels decreased. Together, these findings suggest that purified anthocyanin consumption enhances spatial learning and motor coordination in aged animals and can be attributed to the modulation of key synaptic proteins, which support integrity and maintenance of synaptic function.
- Published
- 2021
- Full Text
- View/download PDF
13. Characterization of Stilbene Composition in Grape Berries from Wild Vitis Species in Year-To-Year Harvest.
- Author
-
Gabaston J, Valls Fonayet J, Franc C, Waffo-Teguo P, de Revel G, Hilbert G, Gomès E, Richard T, and Mérillon JM
- Subjects
- Fruit chemistry, Fruit classification, Mass Spectrometry, Molecular Structure, Phenols chemistry, Vitis classification, Plant Extracts chemistry, Stilbenes chemistry, Vitis chemistry
- Abstract
Asian and American Vitis species possess a strong potential for crossbreeding programs, owing to their several resistance properties. Stilbenes are phenolic compounds present in grape berries and are well-known for their main role as phytoalexins and resistance to biotic stresses in plants. However, their identification and quantification in grape berries from wild Vitis remains unexplored. A mass spectrometry multiple reaction monitoring method combined with the analysis of pure standards allowed for the unambiguous characterization of 20 stilbenes in the grape berry skin extracts of nine native Vitis species and one cultivated Vitis vinifera species (cv. Cabernet Sauvignon). A main occurrence of monomeric ( Z -piceid, E -piceid, E -isorhapontin, and E -astringin), dimeric ( E -ε-viniferin, Z -ε-viniferin, and pallidol), and oligomeric (isohopeaphenol and r-viniferin) stilbenes was highlighted. Some stilbenes were clearly characterized for the first time in grape berries, such as the dimers ampelopsin A, E -vitisinol C, and parthenocissin A as well as the tetramers r2-viniferin and r-viniferin. Stilbene composition and content varied widely among several Vitis species and vintage years.
- Published
- 2020
- Full Text
- View/download PDF
14. Impact of polyphenols on receptor-ligand interactions by NMR: the case of neurotensin (NT)-neurotensin receptor fragment (NTS1) complex.
- Author
-
Richard T, Petit E, Pouységu L, Monti JP, Bondon A, Sylla T, Mérillon JM, Quideau S, and Da Costa G
- Subjects
- Ligands, Models, Molecular, Polyphenols, Neurotensin chemistry, Receptors, Neurotensin chemistry
- Abstract
Ligand-receptor interactions can be implicated in many pathological events such as chronic neurodegenerative diseases. Thus, the discovery of molecules disrupting this type of interactions could be an interesting therapeutic approach. Polyphenols are well known for their affinity for proteins and several studies have characterized these direct interactions. But studying the direct influence of multi-therapeutic drugs on a ligand-receptor complex relevant to a neurodegenerative disorder is a challenging issue. Solution NMR, molecular modeling and iterative calculations were used to obtain information about the interaction between a phenolic compound, α-glucogallin (α- 2 ) and a ligand/fragment receptor complex neurotensin (NT) and its receptor NTS1. The α- 2 was shown to bind to NT and a peptidic fragment of its NTS1 receptor, independently. Although the formation of the corresponding ligand-receptor complex did not seem to be affected, this experimental modeling protocol will enable the evaluation of other anti-amyloidogenic compounds such as blockers of NT-NTS1 binding. These types of studies help in understanding the specificity and influence in binding and can provide information to develop new molecules with a putative pharmacological interest.Communicated by Ramaswamy H. Sarma.
- Published
- 2020
- Full Text
- View/download PDF
15. Separation and isolation of major polyphenols from maritime pine (Pinus pinaster) knots by two-step centrifugal partition chromatography monitored by LC-MS and NMR spectroscopy.
- Author
-
Gabaston J, Leborgne C, Waffo-Téguo P, Pedrot E, Richard T, Mérillon JM, and Valls Fonayet J
- Subjects
- Chromatography, Liquid, Magnetic Resonance Spectroscopy, Mass Spectrometry, Polyphenols chemistry, Centrifugation, Pinus chemistry, Polyphenols isolation & purification
- Abstract
Pine knots are a rich source of lignans, flavonoids, and stilbenes. These bioactive compounds are widely known for their roles to combat human disorders but also to protect plants against pathogens. In order to gain knowledge inside their potential activities, a suitable isolation and purification of these high-added value compounds is required. To this end, centrifugal partition chromatography, as a rapid and useful methodology of separation, was employed and developed. The coefficient partition values (K
D ) of six major compounds in nine biphasic solvent systems were determined to evaluate the most appropriate system. Two-step centrifugal partition chromatography was required to separate lignans using ARIZONA system K (n-heptane/ethyl acetate/methanol/water 1:2:1:2, v:v) and to isolate stilbenes and flavonoids using ARIZONA system P (n-heptane/ethyl acetate/methanol/water 6:5:6:5, v:v). Eight one-compound enriched-fractions were obtained as follows: nortrachelogenin (70.1%), secoisolariciresinol (53.7%), isolariciresinol (61.1%), taxifolin (48.4%), pinocembrin (91.3%), pinobanksin (91.1%), pinosylvin (91.4%), and pinosylvin monomethyl ether (91.1%). Additionally, the centrifugal partition chromatography allowed to unravel the composition of pine knot owing to the several fractions generated. Twenty-two compounds were characterized by liquid chromatography-mass spectrometry and NMR spectroscopy, some of which are described for the first time in literature., (© 2020 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.)- Published
- 2020
- Full Text
- View/download PDF
16. New glucosyloxybenzyl 2R-benzylmalate derivatives from the undergrounds parts of Arundina graminifolia (Orchidaceae).
- Author
-
Auberon F, Olatunji OJ, Waffo-Teguo P, Adekoya AE, Bonté F, Mérillon JM, and Lobstein A
- Subjects
- Flowers chemistry, Molecular Structure, Phytochemicals chemistry, Phytochemicals isolation & purification, Plant Roots chemistry, Antioxidants pharmacology, Glycoside Hydrolase Inhibitors pharmacology, Orchidaceae chemistry, Phytochemicals pharmacology
- Abstract
Phytochemical investigation of the underground part of the blossoming tropical orchid Arundina graminifolia led to the isolation of six new glucosyloxybenzyl 2R-benzylmalate derivatives named arundinosides L-Q (1-6) together with 5 known compounds arundinosides D-F, J and K (7-11). The structures of the isolated compounds were determined by extensive spectroscopic data analysis. The anti-α-glucosidase and antioxidant activities of the isolated compounds were determined. The result indicated that compounds 4-6 and 9 showed moderate to weak α-glucosidase inhibitory effects as well as moderate antioxidant effect., (Copyright © 2019 Elsevier B.V. All rights reserved.)
- Published
- 2019
- Full Text
- View/download PDF
17. Wood and roots of major grapevine cultivars and rootstocks: A comparative analysis of stilbenes by UHPLC-DAD-MS/MS and NMR.
- Author
-
Gabaston J, Leborgne C, Waffo-Teguo P, Valls J, Palos Pinto A, Richard T, Cluzet S, and Mérillon JM
- Subjects
- Plant Extracts analysis, Plant Extracts chemistry, Polymerization, Chromatography, High Pressure Liquid methods, Plant Roots chemistry, Proton Magnetic Resonance Spectroscopy methods, Stilbenes analysis, Tandem Mass Spectrometry methods, Vitis chemistry, Wood
- Abstract
Introduction: Grapevine wood and roots are by-products obtained during vineyard management. This plentiful biomass is known to be rich in stilbenes and can be used as a source of high-value compounds as well as active natural extracts. However, the stilbenes in grapevine wood and roots from different cultivars and rootstocks remain to be characterized., Objective: The present study investigated the stilbene content of eight major Vitis vinifera cultivars and six different rootstocks. In addition, the distribution of stilbenes was established for each of seven parts into which the plants were sub-divided., Methodology: For stilbene characterization and quantification purposes, an ultra-high performance liquid chromatography-diode array detector-mass spectrometry (UHPLC-DAD-MS/MS) analysis of different samples was carried out. Moreover, structural data of stilbenes was unambiguously studied by nuclear magnetic resonance (NMR) spectra., Results: Whatever the cultivar/rootstock combination, stilbenes were found to be oligomerized from the aerial part to the root system. Furthermore, stilbene content varied widely depending on the cultivars and rootstocks. For instance, the cultivars Merlot, Tannat and Gamay noir were the richest in stilbenes while the rootstocks Gravesac, Fercal and 3390C contained the highest amounts., Conclusion: These findings provide insight into the knowledge that major grapevine cultivars and rootstocks can be used as a potential source of complex stilbenes., (© 2019 John Wiley & Sons, Ltd.)
- Published
- 2019
- Full Text
- View/download PDF
18. Impact of different elicitors on grapevine leaf metabolism monitored by 1H NMR spectroscopy.
- Author
-
Burdziej A, Da Costa G, Gougeon L, Le Mao I, Bellée A, Corio-Costet MF, Mérillon JM, Richard T, Szakiel A, and Cluzet S
- Subjects
- Cyclopentanes metabolism, Oxylipins metabolism, Plant Leaves chemistry, Principal Component Analysis, Proton Magnetic Resonance Spectroscopy, Salicylic Acid metabolism, Vitis chemistry, Metabolomics, Plant Leaves metabolism, Vitis metabolism
- Abstract
Introduction: Grapevine protection is an important issue in viticulture. To reduce pesticide use, sustainable disease control strategies are proposed, including a promising alternative method based on the elicitor-triggered stimulation of the grapevine natural defense responses. However, detailed investigations are necessary to characterize the impact of such defense induction on the primary metabolism., Objectives: Our aim was to use a metabolomics approach to assess the impact on grapevine of different elicitors dependent on the salicylic acid (SA) and/or jasmonic acid (JA) pathway. For this purpose, leaves of grapevine foliar cuttings were treated with methyl jasmonate, acibenzolar-S-methyl or phosphonates., Methods: According to the elicitor, common and discriminating metabolites were elucidated using
1 H NMR measurements and principal component analysis., Results: A wide range of compounds including carbohydrates, amino acids, organic acids, phenolics and amines were identified. The score plots obtained by combining PC1 versus PC2 and PC1 versus PC3 allowed a clear separation of samples, so metabolite fingerprinting showed an extensive reprogramming of primary metabolic pathways after elicitation., Conclusion: The methods applied were found to be accurate for the rapid determination and differential characterization of plant samples based on their metabolic composition. These investigations can be very useful because the application of plant defense stimulators is gaining greater importance as an alternative strategy to pesticides in the vineyard.- Published
- 2019
- Full Text
- View/download PDF
19. Constraint-Based Modeling Highlights Cell Energy, Redox Status and α-Ketoglutarate Availability as Metabolic Drivers for Anthocyanin Accumulation in Grape Cells Under Nitrogen Limitation.
- Author
-
Soubeyrand E, Colombié S, Beauvoit B, Dai Z, Cluzet S, Hilbert G, Renaud C, Maneta-Peyret L, Dieuaide-Noubhani M, Mérillon JM, Gibon Y, Delrot S, and Gomès E
- Abstract
Anthocyanin biosynthesis is regulated by environmental factors (such as light, temperature, and water availability) and nutrient status (such as carbon, nitrogen, and phosphate nutrition). Previous reports show that low nitrogen availability strongly enhances anthocyanin accumulation in non carbon-limited plant organs or cell suspensions. It has been hypothesized that high carbon-to-nitrogen ratio would lead to an energy excess in plant cells, and that an increase in flavonoid pathway metabolic fluxes would act as an "energy escape valve," helping plant cells to cope with energy and carbon excess. However, this hypothesis has never been tested directly. To this end, we used the grapevine Vitis vinifera L. cultivar Gamay Teinturier (syn. Gamay Freaux or Freaux Tintorier, VIVC #4382) cell suspension line as a model system to study the regulation of anthocyanin accumulation in response to nitrogen supply. The cells were sub-cultured in the presence of either control (25 mM) or low (5 mM) nitrate concentration. Targeted metabolomics and enzyme activity determinations were used to parametrize a constraint-based model describing both the central carbon and nitrogen metabolisms and the flavonoid (phenylpropanoid) pathway connected by the energy (ATP) and reducing power equivalents (NADPH and NADH) cofactors. The flux analysis (2 flux maps generated, for control and low nitrogen in culture medium) clearly showed that in low nitrogen-fed cells all the metabolic fluxes of central metabolism were decreased, whereas fluxes that consume energy and reducing power, were either increased (upper part of glycolysis, shikimate, and flavonoid pathway) or maintained (pentose phosphate pathway). Also, fluxes of flavanone 3β-hydroxylase, flavonol synthase, and anthocyanidin synthase were strongly increased, advocating for a regulation of the flavonoid pathway by alpha-ketoglutarate levels. These results strongly support the hypothesis of anthocyanin biosynthesis acting as an energy escape valve in plant cells, and they open new possibilities to manipulate flavonoid production in plant cells. They do not, however, support a role of anthocyanins as an effective mechanism for coping with carbon excess in high carbon to nitrogen ratio situations in grape cells. Instead, constraint-based modeling output and biomass analysis indicate that carbon excess is dealt with by vacuolar storage of soluble sugars.
- Published
- 2018
- Full Text
- View/download PDF
20. Comparison of the Impact of Two Molecules on Plant Defense and on Efficacy against Botrytis cinerea in the Vineyard: A Plant Defense Inducer (Benzothiadiazole) and a Fungicide (Pyrimethanil).
- Author
-
Bellée A, Cluzet S, Dufour MC, Mérillon JM, and Corio-Costet MF
- Subjects
- Botrytis physiology, Gene Expression Regulation, Plant, Plant Diseases genetics, Plant Diseases immunology, Plant Proteins genetics, Plant Proteins immunology, Vitis genetics, Vitis immunology, Botrytis drug effects, Fungicides, Industrial pharmacology, Plant Diseases microbiology, Pyrimidines pharmacology, Thiadiazoles pharmacology, Vitis microbiology
- Abstract
Grapevine is subject to diseases that affect yield and wine quality caused by various pathogens including Botrytis cinerea. To limit the use of fungicides, an alternative is to use plant elicitors such as benzothiadiazole (BTH). We investigated the effect of a fungicide (Pyrimethanil) and an elicitor (benzothiadiazole) on plant defenses. Applications for two consecutive years in the vineyard significantly reduced gray mold. Two and seven days after treatments, the expressions of 48 genes involved in defenses showed differential modulation (up- or down-regulation) depending on treatment. Some genes were identified as potential markers of protection and were linked to an increase in total polyphenols (TP) in leaves. Surprisingly, the fungicide also induced the expression of defense genes and increased the polyphenol content. This suggests that BTH acts as an efficient elicitor in the vineyard and that Pyrimethanil may act, in part, as a defense-inducing agent on the vine.
- Published
- 2018
- Full Text
- View/download PDF
21. Arundinosides A-G, new glucosyloxybenzyl 2R-benzylmalate derivatives from the aerial parts of Arundina graminifolia.
- Author
-
Auberon F, Olatunji OJ, Krisa S, Herbette G, Antheaume C, Bonté F, Mérillon JM, and Lobstein A
- Subjects
- Animals, Benzyl Compounds isolation & purification, Magnetic Resonance Spectroscopy, Maleates isolation & purification, Molecular Structure, Neuroprotective Agents isolation & purification, PC12 Cells, Plant Components, Aerial chemistry, Rats, Thailand, Benzyl Compounds chemistry, Maleates chemistry, Neuroprotective Agents chemistry, Orchidaceae chemistry
- Abstract
Seven new glucosyloxybenzyl 2R-benzylmalate derivatives, arundinosides A-G (1-7) were isolated from the aerial parts of the bamboo orchid Arundina graminifolia. This is the first occurrence of this class of compounds in the genus Arundina. Their planar structures and absolute configuration were determined by extensive NMR spectroscopic data as well as chemical conversion. Their neuroprotective properties were also evaluated on their potential ability to reduce the beta amyloid damage on PC12 cell model., (Copyright © 2017 Elsevier B.V. All rights reserved.)
- Published
- 2018
- Full Text
- View/download PDF
22. Pinus pinaster Knot: A Source of Polyphenols against Plasmopara viticola.
- Author
-
Gabaston J, Richard T, Cluzet S, Palos Pinto A, Dufour MC, Corio-Costet MF, and Mérillon JM
- Subjects
- Antifungal Agents chemistry, Antifungal Agents isolation & purification, Plant Extracts chemistry, Plant Extracts isolation & purification, Polyphenols chemistry, Polyphenols isolation & purification, Antifungal Agents pharmacology, Oomycetes drug effects, Pinus chemistry, Plant Extracts pharmacology, Polyphenols pharmacology
- Abstract
Pine knot extract from Pinus pinaster byproducts was characterized by UHPLC-DAD-MS and NMR. Fourteen polyphenols divided into four classes were identified as follows: lignans (nortrachelogenin, pinoresinol, matairesinol, isolariciresinol, secoisolariciresinol), flavonoids (pinocembrin, pinobanksin, dihydrokaempferol, taxifolin), stilbenes (pinosylvin, pinosylvin monomethyl ether, pterostilbene), and phenolic acids (caffeic acid, ferulic acid). The antifungal potential of pine knot extract, as well as the main compounds, was tested in vitro against Plasmopara viticola. The ethanolic extract showed a strong antimildew activity. In addition, pinosylvins and pinocembrin demonstrated significant inhibition of zoospore mobility and mildew development. These findings strongly suggest that pine knot is a potential biomass that could be used as a natural antifungal product.
- Published
- 2017
- Full Text
- View/download PDF
23. Antioxidant and Cytoprotective Activities of Grapevine Stilbenes.
- Author
-
Biais B, Krisa S, Cluzet S, Da Costa G, Waffo-Teguo P, Mérillon JM, and Richard T
- Subjects
- Animals, Cell Survival drug effects, Molecular Structure, PC12 Cells, Plant Stems chemistry, Protective Agents analysis, Protective Agents pharmacology, Rats, Antioxidants chemistry, Antioxidants pharmacology, Plant Extracts chemistry, Plant Extracts pharmacology, Stilbenes chemistry, Stilbenes pharmacology, Vitis chemistry
- Abstract
Grapevine stem extracts are viticulture byproducts rich in stilbenes that are increasingly studied for their potential biological activities. This study aimed to investigate some biological activities of a grape byproduct with high stilbenoid content and to point out the molecules responsible of these beneficial activities. As a consequence, the extract was subjected to a bioguided fractionation and separation by centrifugal partition chromatography. The obtained fractions were characterized by liquid chromatography coupled to mass spectrometry and nuclear magnetic resonance. Fractions were purified further by column chromatography and resulted in the purification of the main constituents. Thirteen stilbenes have been quantified. The most abundant compounds were ε-viniferin, resveratrol, and, in lesser amounts, isohopeaphenol and ampelopsin A. The extract, fractions, and major stilbenes were tested for their antioxidant activity by oxygen radical absorbance capacity and their cyprotective effects against β-amyloid on rat pheochromocytoma cells. Among them, fraction 5 showed significant antioxidant activity and fraction 2 had a significant cytoprotective effect against β-amyloid-induced toxicity. Two putative inhibitors of β-amyloid toxicity have been identified: ampelopsin A and piceatannol.
- Published
- 2017
- Full Text
- View/download PDF
24. In Vitro Glucuronidation and Sulfation of ε-Viniferin, a Resveratrol Dimer, in Humans and Rats.
- Author
-
Courtois A, Jourdes M, Dupin A, Lapèze C, Renouf E, Biais B, Teissedre PL, Mérillon JM, Richard T, and Krisa S
- Subjects
- Animals, Benzofurans chemistry, Glucuronic Acid chemistry, Glucuronic Acid metabolism, Glucuronides chemistry, Humans, Inactivation, Metabolic, Liver enzymology, Rats, Stilbenes chemistry, Sulfates chemistry, Benzofurans metabolism, Glucuronides metabolism, Stilbenes metabolism, Sulfates metabolism
- Abstract
ε-Viniferin is a resveratrol dimer that possesses antioxidant or anti-inflammatory activities. However little is known about the metabolism of this oligostilbene. This study was thus undertaken as a first approach to identify and characterize the metabolites of ε-viniferin and to describe the kinetic profile of their appearance in humans and rats. The glucuronides and sulfates of ε-viniferin were first obtained by chemical hemi-synthesis and were fully characterized by UPLC-MS and NMR spectroscopy. Then, ε-viniferin was incubated with human or rat S9 liver fractions that led to the formation of four glucuronoconjugates and four sulfoconjugates. In both species, ε-viniferin was subjected to an intense metabolism as 70 to 80% of the molecule was converted to glucuronides and sulfates. In humans, the hepatic clearance of ε-viniferin (V
max /Km ) for glucuronidation and sulfation were 4.98 and 6.35 µL/min/mg protein, respectively, whereas, in rats, the hepatic clearance for glucuronidation was 20.08 vs. 2.59 µL/min/mg protein for sulfation. In humans, three major metabolites were observed: two glucuronides and one sulfate. By contrast, only one major glucuronide was observed in rats. This strong hepatic clearance of ε-viniferin in human and rat could explain its poor bioavailability and could help to characterize its active metabolites.- Published
- 2017
- Full Text
- View/download PDF
25. Stilbenes from Vitis vinifera L. Waste: A Sustainable Tool for Controlling Plasmopara Viticola.
- Author
-
Gabaston J, Cantos-Villar E, Biais B, Waffo-Teguo P, Renouf E, Corio-Costet MF, Richard T, and Mérillon JM
- Subjects
- Fungicides, Industrial chemistry, Fungicides, Industrial isolation & purification, Molecular Structure, Oomycetes growth & development, Plant Diseases microbiology, Plant Diseases prevention & control, Plant Extracts chemistry, Plant Extracts isolation & purification, Plant Roots microbiology, Stilbenes chemistry, Stilbenes isolation & purification, Fungicides, Industrial pharmacology, Oomycetes drug effects, Plant Extracts pharmacology, Stilbenes pharmacology, Vitis chemistry, Waste Products analysis
- Abstract
Stilbene-enriched extracts from Vitis vinifera waste (cane, wood, and root) were characterized by UHPLC-MS. Eleven stilbenes were identified and quantified as follows: ampelopsin A, (E)-piceatannol, pallidol, (E)-resveratrol, hopeaphenol, isohopeaphenol, (E)-ε-viniferin, (E)-miyabenol C, (E)-ω-viniferin, r2-viniferin, and r-viniferin. The fungicide concentration inhibiting 50% of growth of Plasmopara viticola sporulation (IC
50 ) was determined for the extracts and also for the main compounds isolated. r-Viniferin followed by hopeaphenol and r2-viniferin showed low IC50 and thus high efficacy against Plasmopara viticola. Regarding stilbene extracts, wood extract followed by root extract showed the highest antifungal activities. These data suggest that stilbene complex mixtures from Vitis vinifera waste could be used as a cheap source of bioactive stilbenes for the development of natural fungicides.- Published
- 2017
- Full Text
- View/download PDF
26. Two New Stilbenoids from the Aerial Parts of Arundina graminifolia (Orchidaceae).
- Author
-
Auberon F, Olatunji OJ, Krisa S, Antheaume C, Herbette G, Bonté F, Mérillon JM, and Lobstein A
- Subjects
- Amyloid beta-Peptides toxicity, Animals, Cell Survival drug effects, Cytoprotection drug effects, PC12 Cells, Rats, Orchidaceae chemistry, Plant Components, Aerial chemistry, Stilbenes chemistry, Stilbenes isolation & purification, Stilbenes pharmacology
- Abstract
Two new phenanthrene derivatives, a phenanthrenequinone named arundiquinone ( 1 ) and a 9,10-dihydrophenanthrene named arundigramin ( 2 ) together with a known lignin dimer ( 3 ) and seven known stilbenoids ( 4 - 10 ) were isolated from the aerial parts of the Asian orchid Arundina graminifolia . The structures of the isolated compounds were elucidated by spectroscopic methods, including extensive 1D, 2D NMR (heteronuclear single quantum coherence (HSQC), heteronuclear multiple-bond correlation spectroscopy (HMBC), and HR-ESI-MS techniques, as well as comparison with respective literature reports. The cytoprotective activity of the isolated compounds were evaluated for their ability to reduce beta amyloid induced toxicity on undifferentiated PC12 cells. Compound 8 showed moderate cytoprotective activity at 0.5 µmol/L (71% of cell viability) while the other compounds showed no significant activity at the highest concentration tested.
- Published
- 2016
- Full Text
- View/download PDF
27. Hyphenating Centrifugal Partition Chromatography with Nuclear Magnetic Resonance through Automated Solid Phase Extraction.
- Author
-
Bisson J, Brunel M, Badoc A, Da Costa G, Richard T, Mérillon JM, and Waffo-Téguo P
- Abstract
Centrifugal partition chromatography (CPC) and all countercurrent separation apparatus provide chemists with efficient ways to work with complex matrixes, especially in the domain of natural products. However, despite the great advances provided by these techniques, more efficient ways of analyzing the output flow would bring further enhancement. This study describe a hyphenated approach made by coupling NMR with CPC through a hybrid-indirect coupling made possible by using a solid phase extraction (SPE) apparatus intended for high-pressure liquid chromatography (HPLC)-NMR hyphenation. Some hardware changes were needed to adapt the incompatible flow-rates and a reverse-engineering approach that led to the specific software required to control the apparatus. 1D
1 HNMR and1 H-1 H correlation spectroscopy (COSY) spectra were acquired in reasonable time without the need for any solvent-suppression method thanks to the SPE nitrogen drying step. The reduced usage of expensive deuterated solvents from several hundreds of milliliters to the milliliter order is the major improvement of this approach compared to the previously published ones.- Published
- 2016
- Full Text
- View/download PDF
28. Phenolic contents and bioactive potential of peach fruit extracts.
- Author
-
Mokrani A, Krisa S, Cluzet S, Da Costa G, Temsamani H, Renouf E, Mérillon JM, Madani K, Mesnil M, Monvoisin A, and Richard T
- Subjects
- Animals, Antioxidants analysis, Antioxidants pharmacology, Chromatography, Liquid, Fluoresceins, Mass Spectrometry, PC12 Cells, Phenols chemistry, Phenols pharmacology, Rats, Reactive Oxygen Species chemistry, Fruit chemistry, Phenols analysis, Prunus persica
- Abstract
Several cultivars of peach fruit (Prunus persica L.) were investigated. Their phenolic composition and concentration were assessed by LC-MS. Concentrations were calculated in mg per g of dry weight extract. Their antioxidant capacity (Folin-Ciocalteu, ORAC, DPPH, ABTS, PFRAP and ICA), inhibitory property against β-amyloid and α-synuclein fibril formation and protective capacity against Aβ-induced toxicity on PC12 cell lines (viability assessed by MTT assay and intracellular ROS production by DCFH-DA assay) were evaluated. Fifteen different phenolic compounds were identified and quantified. In particular, new isorhamnetin derivatives were identified. Phenolic contents were ranged between 19 and 82mg/g. Spring Belle extract had the highest content and Romea the lowest. Except for the ICA assay, a good correlation between phenolic content and the antioxidant capacities of peach fruit extracts was found, indicating that phenolic compounds are major contributors to their antioxidant capacity. Results indicate that the phenolic extract of peach cultivars inhibits Aβ and αS fibril formation and protects PC12 cell lines against Aβ-induced toxicity., (Copyright © 2016. Published by Elsevier Ltd.)
- Published
- 2016
- Full Text
- View/download PDF
29. Piceatannol and Other Wine Stilbenes: A Pool of Inhibitors against α-Synuclein Aggregation and Cytotoxicity.
- Author
-
Temsamani H, Krisa S, Decossas-Mendoza M, Lambert O, Mérillon JM, and Richard T
- Subjects
- Animals, Benzothiazoles, Cell Survival drug effects, Electrophoresis, Polyacrylamide Gel, Flavonoids pharmacology, Microscopy, Electron, Transmission, PC12 Cells, Parkinson Disease drug therapy, Phenols, Rats, Thiazoles, alpha-Synuclein antagonists & inhibitors, Stilbenes pharmacology, Wine analysis, alpha-Synuclein toxicity
- Abstract
The aggregation of α-synuclein is one on the key pathogenic events in Parkinson's disease. In the present study, we investigated the inhibitory capacities of stilbenes against α-synuclein aggregation and toxicity. Thioflavin T fluorescence, transmission electronic microscopy, and SDS-PAGE analysis were performed to investigate the inhibitory effects of three stilbenes against α-synuclein aggregation: piceatannol, ampelopsin A, and isohopeaphenol. Lipid vesicle permeabilization assays were performed to screen stilbenes for protection against membrane damage induced by aggregated α-synuclein. The viability of PC12 cells was examined using an MTT assay to assess the preventive effects of stilbenes against α-synuclein-induced toxicity. Piceatannol inhibited the formation of α synuclein fibrils and was able to destabilize preformed filaments. It seems to induce the formation of small soluble complexes protecting membranes against α-synuclein-induced damage. Finally, piceatannol protected cells against α-synuclein-induced toxicity. The oligomers tested (ampelopsin A and hopeaphenol) were less active.
- Published
- 2016
- Full Text
- View/download PDF
30. Unusual compounds from Galium mollugo and their inhibitory activities against ROS generation in human fibroblasts.
- Author
-
Chaher N, Krisa S, Delaunay JC, Bernillon S, Pedrot E, Mérillon JM, Atmani D, and Richard T
- Subjects
- Antioxidants analysis, Antioxidants pharmacology, Cell Survival drug effects, Cell Survival physiology, Cells, Cultured, Dose-Response Relationship, Drug, Fibroblasts metabolism, Humans, Plant Components, Aerial, Reactive Oxygen Species metabolism, Fibroblasts drug effects, Galium, Plant Extracts analysis, Plant Extracts pharmacology, Reactive Oxygen Species antagonists & inhibitors
- Abstract
Three unusual dioxatricyclodecenone compounds, mollugoside A, E-mollugoside B and Z-mollugoside B and, together with known flavonoids, were isolated from the aerial parts of Galium mollugo collected in north-eastern Algeria. Their structures were elucidated by analysis of spectroscopic data, including 1D and 2D NMR. Flavonoids and mollugoside A significantly reduced reactive oxygen species (ROS) generation in human fibroblasts., (Copyright © 2015 Elsevier B.V. All rights reserved.)
- Published
- 2016
- Full Text
- View/download PDF
31. Isolation and structure elucidation of bioactive compounds from the roots of the Tunisian Ononis angustissima L.
- Author
-
Ghribi L, Waffo-Téguo P, Cluzet S, Marchal A, Marques J, Mérillon JM, and Ben Jannet H
- Subjects
- Animals, Antioxidants chemistry, Antioxidants isolation & purification, Benzothiazoles antagonists & inhibitors, Biphenyl Compounds antagonists & inhibitors, Cell Survival drug effects, Dose-Response Relationship, Drug, Free Radicals antagonists & inhibitors, Molecular Structure, PC12 Cells, Picrates antagonists & inhibitors, Plant Extracts chemistry, Plant Extracts isolation & purification, Rats, Structure-Activity Relationship, Sulfonic Acids antagonists & inhibitors, Tunisia, Antioxidants pharmacology, Ononis chemistry, Plant Extracts pharmacology, Plant Roots chemistry
- Abstract
A phytochemical investigation of the roots of Ononis angustissima L. (Fabaceae) offered to the bio-guided isolation of new isoflavone 3-(4-(glucopyranosyloxy)-5-hydroxy-2-methoxyphenyl)-7-hydroxy-4H-chromen-4-one 1, together with nine known compounds, ononin 2, formononetin 3, (+)-puerol A-2'-O-β-D-glucose 4, (-)-puerol B-2'-O-β-D-glucopyranose ((-)-sophoraside A) 5, (+)-puerol A 6, (-)-trifolirhizin 7, (-)-trifolirhizin-6'-O-malonate 8, (-)-maackiain 9 and (-)-medicarpin 10. Compounds 2-10 were isolated and identified for the first time in Ononis angustissima. We investigated antioxidant capacities of isolated molecules and results showed that compound 6 exhibited the highest antioxidant activity with IC50 values of 19.53 μg/mL, 28.29 μg/mL and 38.53 μg/mL by DPPH radical, ABTS radical cation and reducing power assay, respectively, and an interesting IC50 (20.45 μg/mL) of 1 against DPPH. In addition, the neuroprotective activity of six isolated molecules (4-7, 9, 10) were evaluated. Following the exposure of PC12 cells to Aβ25-35, compounds 9 and 10 triggered a significant increase of cell viability and in a dose dependent manner., (Copyright © 2015 Elsevier Ltd. All rights reserved.)
- Published
- 2015
- Full Text
- View/download PDF
32. Flavonol profiles in berries of wild Vitis accessions using liquid chromatography coupled to mass spectrometry and nuclear magnetic resonance spectrometry.
- Author
-
Hilbert G, Temsamani H, Bordenave L, Pedrot E, Chaher N, Cluzet S, Delaunay JC, Ollat N, Delrot S, Mérillon JM, Gomès E, and Richard T
- Subjects
- Antioxidants chemistry, Chromatography, High Pressure Liquid methods, Fruit chemistry, Magnetic Resonance Spectroscopy methods, Mass Spectrometry methods, Flavonols chemistry, Vitis chemistry
- Abstract
The flavonol profiles of grape berry skins were analysed in order to assess phenotypic variation between six grapevines belonging to six different species: Vitis vinifera, Vitiscandicans, Vitischampinii, Vitisamurensis, Vitiscinerea and Vitisdoaniana. High-performance liquid chromatography coupled to mass spectrometry (LC-MS) and NMR spectrometry (LC-NMR) were used to separate and identify the flavonols present in these species. The combination of LC-MS and LC-NMR data resulted in the identification of eighteen flavonols. In particular, the new flavonol diglycoside and pentoside derivatives were determined. In addition, the antioxidant capacities of flavonol grape skin extracts were evaluated by using an oxygen radical absorbance capacity method (ORAC)., (Copyright © 2014 Elsevier Ltd. All rights reserved.)
- Published
- 2015
- Full Text
- View/download PDF
33. Development of an analytical methodology using Fourier transform mass spectrometry to discover new structural analogs of wine natural sweeteners.
- Author
-
Marchal A, Génin E, Waffo-Téguo P, Bibès A, Da Costa G, Mérillon JM, and Dubourdieu D
- Subjects
- Biological Products analysis, Biological Products isolation & purification, Chromatography, High Pressure Liquid, Drug Discovery, Isomerism, Sweetening Agents analysis, Sweetening Agents isolation & purification, Biological Products chemistry, Fourier Analysis, Mass Spectrometry methods, Quercus chemistry, Sweetening Agents chemistry, Wine, Wood chemistry
- Abstract
Volatile and non-volatile molecules are directly responsible for the thrill and excitement provided by wine-tasting. Their elucidation requires powerful analytical techniques and innovative methodologies. In a recent work, two novel sweet compounds called quercotriterpenosides (QTT) were identified in oak wood used for wine-ageing. The aim of the present study is to discover structural analogs of such natural sweeteners in oak wood. For this purpose, an analytical approach was developed as an alternative to chemical synthesis. Orbitrap mass spectrometry proved to be a crucial technique both to demonstrate the presence of QTT analogs in oak wood by targeted screening and to guide the purification pathway of these molecules using complementary chromatographic tools. Four compounds were isolated and identified for the first time: two isomers, one glucosyl derivative and one galloyl derivative of QTT. Their tasting showed that only the two new isomers were sweet, thus demonstrating both the pertinence of the strategy and the influence of functional groups on gustatory properties. Finally, this paper presents some developments involving multistage Fourier transform mass spectrometry (FTMS) to provide solid structural information on these functional groups prior to any purification of compounds. Such analytical developments could be particularly useful for research on taste-active or bio-active products., (Copyright © 2014 Elsevier B.V. All rights reserved.)
- Published
- 2015
- Full Text
- View/download PDF
34. Polyphenols from the stems of Morus alba and their inhibitory activity against nitric oxide production by lipopolysaccharide-activated microglia.
- Author
-
Rivière C, Krisa S, Péchamat L, Nassra M, Delaunay JC, Marchal A, Badoc A, Waffo-Téguo P, and Mérillon JM
- Subjects
- Animals, Cell Line, Coumarins pharmacology, Glycosides isolation & purification, Glycosides pharmacology, Lipopolysaccharides, Mice, Microglia metabolism, Molecular Structure, Nitric Oxide metabolism, Plant Stems chemistry, Polyphenols pharmacology, Coumarins isolation & purification, Microglia drug effects, Morus chemistry, Nitric Oxide antagonists & inhibitors, Polyphenols isolation & purification
- Abstract
Neuroinflammatory processes are involved in the pathogenesis of many neurodegenerative disorders. Microglial cells, the main immune cells of the central nervous system, represent a target of interest to search for naturally occurring anti-inflammatory products. In this study, we evaluated the anti-inflammatory properties of polyphenols obtained from the stems of Morus alba. This edible species, known as white mulberry, is frequently studied because of its traditional use in Asian medicine and its richness in different types of polyphenols, some of which are known to be phytoalexins. One new coumarin glycoside, isoscopoletin 6-(6-O-β-apiofuranosyl-β-glucopyranoside) (1) was mainly isolated by CPC (centrifugal partition chromatography) from this plant, together with seven known polyphenols (2-8). Their structures were established on the basis of spectroscopic analyses including extensive 2D NMR studies. The eight isolated compounds were evaluated for their inhibitory activities on nitric oxide (NO) production in lipopolysaccharide (LPS)-induced BV-2 microglial cells. The absence of cell toxicity is checked by a MTT assay., (Copyright © 2014 Elsevier B.V. All rights reserved.)
- Published
- 2014
- Full Text
- View/download PDF
35. Unambiguous Determination of the Absolute Configuration of Dimeric Stilbene Glucosides from the Rhizomes of Gnetum africanum.
- Author
-
Buffeteau T, Cavagnat D, Bisson J, Marchal A, Kapche GD, Battistini I, Da Costa G, Badoc A, Monti JP, Mérillon JM, and Waffo-Téguo P
- Subjects
- Benzofurans chemistry, Benzofurans isolation & purification, Cameroon, Circular Dichroism, Glucosides isolation & purification, Molecular Structure, Neuroprotective Agents chemistry, Neuroprotective Agents pharmacology, Nuclear Magnetic Resonance, Biomolecular, Rhizome chemistry, Stereoisomerism, Stilbenes isolation & purification, Glucosides chemistry, Gnetum chemistry, Neuroprotective Agents isolation & purification, Stilbenes chemistry
- Abstract
Dimeric stilbene glucosides 1-3 [two diastereomers of (-)-gnemonoside A (1a and 1b), (-)-gnemonoside C (2), and (-)-gnemonoside D (3)] as well as a mixture of the two enantiomers of gnetin C (4) were isolated from the rhizomes of Gnetum africanum. The two enantiomers of gnetin C, (+)-4 and (-)-4, were obtained from the aglycones of 1a and 1b, respectively. The configurations of these stilbenoids were investigated by NMR and vibrational circular dichroism (VCD) experiments. The absolute configurations of (-)-1a, (-)-2, (-)-3, and (-)-4 were established as 7aS,8aS by VCD spectroscopy in combination with density functional theory calculations. The antiamyloidogenic activity of the isolated stilbenes was also evaluated versus beta-amyloid fibrils. The four glucosides of gnetin C (1a, 1b, 2, and 3) were found to be the most active compounds, with inhibition percentages of 56, 56, 58, and 54 at 10 μM, respectively.
- Published
- 2014
- Full Text
- View/download PDF
36. Bioactive stilbenes from Vitis vinifera grapevine shoots extracts.
- Author
-
Chaher N, Arraki K, Dillinseger E, Temsamani H, Bernillon S, Pedrot E, Delaunay JC, Mérillon JM, Monti JP, Izard JC, Atmani D, and Richard T
- Subjects
- Agriculture economics, Amyloid beta-Peptides antagonists & inhibitors, Amyloid beta-Peptides metabolism, Benzofurans analysis, Benzofurans chemistry, Benzofurans economics, Benzofurans isolation & purification, Chromatography, High Pressure Liquid, France, Humans, Industrial Waste economics, Molecular Structure, Neuroprotective Agents chemistry, Neuroprotective Agents economics, Neuroprotective Agents isolation & purification, Neuroprotective Agents pharmacology, Nootropic Agents chemistry, Nootropic Agents economics, Nootropic Agents pharmacology, Peptide Fragments antagonists & inhibitors, Peptide Fragments metabolism, Phenols chemistry, Phenols economics, Plant Extracts economics, Protein Aggregates drug effects, Protein Aggregation, Pathological, Spectrometry, Mass, Electrospray Ionization, Stereoisomerism, Stilbenes analysis, Stilbenes chemistry, Stilbenes economics, Stilbenes pharmacology, Stilbestrols, Drug Discovery, Industrial Waste analysis, Nootropic Agents isolation & purification, Plant Extracts chemistry, Plant Shoots chemistry, Stilbenes isolation & purification, Vitis chemistry
- Abstract
Background: Viticultural residues from commercial viticultural activities represent a potentially important source of bioactive stilbenes such as resveratrol. The main aim of the present study was therefore to isolate, identify and perform biological assays against amyloid-β peptide aggregation of original stilbenes from Vitis vinifera shoots., Results: A new resveratrol oligomer, (Z)-cis-miyabenol C (3), was isolated from Vitis vinifera grapevine shoots together with two newly reported oligostilbenes from Vitis vinifera shoots, vitisinol C (1) and (E)-cis-miyabenol C (2), and six known compounds: piceatannol, resveratrol, (E)-ε-viniferin (trans-ε-viniferin), ω-viniferin, vitisinol C and (E)-miyabenol C. The structures of these resveratrol derivatives were established on the basis of detailed spectroscopic analysis including nuclear magnetic resonance experiments. All the newly reported compounds were tested for their anti-aggregative activity against amyloid-β fibril formation. Vitisinol C was found to exert a significant activity against amyloid-β aggregation., Conclusion: Vitis vinifera grapevine shoots are potentially interesting as a source of new bioactive stilbenes, such as vitisinol C., (© 2013 Society of Chemical Industry.)
- Published
- 2014
- Full Text
- View/download PDF
37. The antioxidant properties of new dimer and two monomers of phenolic acid amides isolated from Limoniastrum guyonianum.
- Author
-
Trabelsi N, Oueslati S, Ksouri R, Nassra M, Marchal A, Krisa S, Abdelly C, Mérillon JM, and Waffo-Téguo P
- Subjects
- Amides isolation & purification, Antioxidants chemistry, Antioxidants isolation & purification, Dimerization, Hydroxybenzoates isolation & purification, Magnetic Resonance Spectroscopy, Molecular Structure, Plant Extracts isolation & purification, Amides chemistry, Hydroxybenzoates chemistry, Plant Extracts chemistry, Plumbaginaceae chemistry
- Abstract
Limoniastramide, a new dimer of phenolic acid amide, isolated from Limoniastrum guyonianum, along with two natural monomers N-E-caffeoyl tyramine (1) and N-E-feruloyl tyramine (2), using centrifugal partition chromatography (CPC). Their structures were determined on the basis of spectroscopic data analysis. We investigate the antioxidant activities of Limoniastrum amides using various in vitro assays. Results showed that N-E-feruloyl tyramine and N-E-caffeoyl tyramine exhibited the highest DPPH scavenging activity compared to the dimer (IC50=0.5, 0.6 and 6.5μg/ml, respectively). In addition, they have significant capacities to inhibit the bleaching of β-carotene. Limoniastramide presented the best activity with an IC50 value equal to 8μg/ml. Finally, the N-E-caffeoyl tyramine showed the highest reducing power (EC50=26μg/ml) compared to the other molecules. The present study found that L. guyonianum amides have effective in vitro antioxidant and radical scavenging activity which can be used in pharmacological and food industry due to their antioxidant properties., (Copyright © 2013. Published by Elsevier Ltd.)
- Published
- 2014
- Full Text
- View/download PDF
38. Viniphenol A, a complex resveratrol hexamer from Vitis vinifera stalks: structural elucidation and protective effects against amyloid-β-induced toxicity in PC12 cells.
- Author
-
Papastamoulis Y, Richard T, Nassra M, Badoc A, Krisa S, Harakat D, Monti JP, Mérillon JM, and Waffo-Teguo P
- Subjects
- Amyloid beta-Peptides pharmacology, Animals, Antioxidants pharmacology, Catechin pharmacology, Dioxanes chemistry, Molecular Structure, Nuclear Magnetic Resonance, Biomolecular, PC12 Cells, Rats, Resveratrol, Stilbenes chemistry, Stilbenes isolation & purification, Stilbenes pharmacology, Vitis chemistry
- Abstract
Stilbenes have received much attention during the last two decades following the discovery of resveratrol in wine. Since then, there have been a growing number of papers reporting various biological activities of naturally occurring stilbenes. The aim of this study was to determine new minor stilbenes from Vitis vinifera stalks. Purification of these compounds was achieved by means of centrifugal partition chromatography, a versatile separation technique that does not require a solid stationary phase. Viniphenol A (1), a new resveratrol hexamer, was isolated along with five oligostilbenoids identified in V. vinifera for the first time, ampelopsin C, davidiol A, leachianol F, leachianol G, and E-maackin, a dimer with an unusual dioxane moiety, and 14 known hydroxystilbenes. The structure and stereochemistry of viniphenol A were determined on the basis of spectroscopic data analysis and molecular modeling under NMR constraints. Viniphenol A showed protective effects against amyloid-β-induced toxicity in PC12 cell cultures.
- Published
- 2014
- Full Text
- View/download PDF
39. Grape polyphenols and propolis mixture inhibits inflammatory mediator release from human leukocytes and reduces clinical scores in experimental arthritis.
- Author
-
Mossalayi MD, Rambert J, Renouf E, Micouleau M, and Mérillon JM
- Subjects
- Animals, Anti-Inflammatory Agents pharmacology, Anti-Inflammatory Agents therapeutic use, Apitherapy, Arthritis, Experimental metabolism, Cachexia drug therapy, Drug Therapy, Combination, Female, Fruit, Humans, Inflammation metabolism, Interferon-gamma metabolism, Monokines metabolism, Phytotherapy, Plant Extracts pharmacology, Plant Extracts therapeutic use, Polyphenols pharmacology, Propolis pharmacology, Rats, Rats, Inbred Strains, Transcriptome, Arthritis, Experimental drug therapy, Inflammation drug therapy, Inflammation Mediators metabolism, Leukocytes metabolism, Polyphenols therapeutic use, Propolis therapeutic use, Vitis chemistry
- Abstract
Polyphenols from red fruits and bee-derived propolis (PR) are bioactive natural products in various in vitro and in vivo models. The present study shows that hematotoxicity-free doses of grape polyphenols (GPE) and PR differentially decreased the secretion of pro-inflammatory cytokines from activated human peripheral blood leucocytes. While GPE inhibited the monocytes/macrophage response, propolis decreased both monokines and interferon γ (IFNγ) production. When used together, their distinct effects lead to the attenuation of all inflammatory mediators, as supported by a significant modulation of the transcriptomic profile of pro-inflammatory genes in human leukocytes. To enforce in vitro data, GPE+PR were tested for their ability to improve clinical scores and cachexia in chronic rat adjuvant-induced arthritis (AA). Extracts significantly reduced arthritis scores and cachexia, and this effect was more significant in animals receiving continuous low doses compared to those receiving five different high doses. Animals treated daily had significantly better clinical scores than corticoid-treated rats. Together, these findings indicate that the GPE+PR combination induces potent anti-inflammatory activity due to their complementary immune cell modulation., (Copyright © 2013 Elsevier GmbH. All rights reserved.)
- Published
- 2014
- Full Text
- View/download PDF
40. Comparative analyses of stilbenoids in canes of major Vitis vinifera L. cultivars.
- Author
-
Lambert C, Richard T, Renouf E, Bisson J, Waffo-Téguo P, Bordenave L, Ollat N, Mérillon JM, and Cluzet S
- Subjects
- Benzofurans analysis, Chromatography, Liquid methods, Phenols analysis, Plant Stems chemistry, Resveratrol, Species Specificity, Polyphenols analysis, Stilbenes analysis, Vitis chemistry
- Abstract
Grapevine canes are rich in resveratrol and its complex derivatives. These compounds have many biological activities and are needed mainly for health purposes. Canes, which are often wasted, can be used to produce these high-value compounds at low cost. We studied sixteen Vitis vinifera L. cultivars among the most widely cultivated ones worldwide. Polyphenols were extracted from their canes and identified by liquid chromatography-nuclear magnetic resonance spectroscopy. We accurately determined the content of E-ε-viniferin, E-resveratrol, E-piceatannol, and vitisin B and, for the first time, that of hopeaphenol and miyabenol C. The canes did not contain these major stilbene compounds in similar proportions, and their abundance and order of abundance varied according to the cultivar. For instance, Pinot noir has very high levels of E-resveratrol and E-ε-viniferin; Gewurztraminer has very high levels of vitisin B, and Carignan and Riesling have very high levels of hopeaphenol. These findings suggest that the right cultivar should be used to obtain the highest yield of a polyphenol of interest.
- Published
- 2013
- Full Text
- View/download PDF
41. Malvidin-3-O-β glucoside, major grape anthocyanin, inhibits human macrophage-derived inflammatory mediators and decreases clinical scores in arthritic rats.
- Author
-
Decendit A, Mamani-Matsuda M, Aumont V, Waffo-Teguo P, Moynet D, Boniface K, Richard E, Krisa S, Rambert J, Mérillon JM, and Mossalayi MD
- Subjects
- Animals, Anthocyanins therapeutic use, Anti-Inflammatory Agents therapeutic use, Arthritis, Experimental metabolism, Arthritis, Experimental physiopathology, Chronic Disease, Cytokines metabolism, Female, Glucosides therapeutic use, Humans, Interleukin-1 antagonists & inhibitors, Interleukin-1 metabolism, Interleukin-6 antagonists & inhibitors, Interleukin-6 metabolism, Leukocytes, Mononuclear drug effects, Leukocytes, Mononuclear metabolism, Macrophage Activation, Macrophages, Peritoneal metabolism, Nitric Oxide biosynthesis, Nitric Oxide Synthase Type II antagonists & inhibitors, Nitric Oxide Synthase Type II metabolism, Polyphenols pharmacology, Rats, Rats, Inbred Lew, Tumor Necrosis Factor-alpha antagonists & inhibitors, Tumor Necrosis Factor-alpha metabolism, Anthocyanins pharmacology, Anti-Inflammatory Agents pharmacology, Arthritis, Experimental drug therapy, Cytokines antagonists & inhibitors, Glucosides pharmacology, Macrophages, Peritoneal drug effects, Nitric Oxide antagonists & inhibitors, Vitis
- Abstract
Polyphenolic anthocyanins are major colorful compounds in red fruits, known to prevent cardiovascular and other diseases. Grape polyphenols are a mixture of various molecules and their exact contribution to above bioactivities remains to be clarified. In the present study, we first analyzed the effect of purified grape-derived compounds on human peripheral blood mononuclear cell (PBMC) survival, proliferation, as well as for their ability to inhibit the activation of human normal macrophages. Data indicated that malvidin-3-O-β glucoside (Malβg), the major grape anthocyanin, is bioactive with no toxicity on human PBMC. Malβg decreased the transcription of genes encoding inflammatory mediators, confirmed by the inhibition of TNFα, IL1, IL-6 and iNOS-derived nitric oxide (NO) secretion from activated macrophages. As Malβg also inhibited inflammatory response of rat macrophages, we investigated the anti-inflammatory potential of Malβg in chronic rat adjuvant-induced arthritis (AIA). Malβg significantly diminished inflammatory cachexia and arthritic paw scores in AIA rats at both therapeutic and preventive levels. In vivo effects of Malβg correlated with down-regulation of NO generation from AIA rats' peritoneal macrophages ex vivo. These data indicate that Malβg, major grape anthocyanin, is a potent anti-inflammatory agent in vitro and in vivo, without detectable toxic effect., (Copyright © 2013 Elsevier Inc. All rights reserved.)
- Published
- 2013
- Full Text
- View/download PDF
42. A faster and a stronger defense response: one of the key elements in grapevine explaining its lower level of susceptibility to Esca?
- Author
-
Lambert C, Khiook IL, Lucas S, Télef-Micouleau N, Mérillon JM, and Cluzet S
- Subjects
- Disease Susceptibility, Gene Expression Regulation, Plant, Plant Leaves genetics, Vitis genetics, Ascomycota, Plant Diseases genetics
- Abstract
Wood diseases like Esca are among the most damaging afflictions in grapevine. The defense mechanisms in this plant-pathogen interaction are not well understood. As some grapevine cultivars have been observed to be less susceptible to Esca than others, understanding the factors involved in this potentially stronger defense response can be of great interest. To lift part of this veil, we elicited Vitis vinifera plants of two cultivars less susceptible to Esca ('Merlot' and 'Carignan') and of one susceptible cultivar ('Cabernet Sauvignon'), and monitored their defense responses at the leaf level. Our model of elicitation consisted in grapevine cuttings absorbing a culture filtrate of one causal agent of Esca, Phaemoniella chlamydospora. This model might reflect the early events occurring in Esca-affected grapevines. The two least susceptible cultivars showed an earlier and stronger defense response than the susceptible one, particularly with regard to induction of the PAL and STS genes, and a higher accumulation of stilbene compounds and some pathogenesis-related proteins.
- Published
- 2013
- Full Text
- View/download PDF
43. Anthocyanin phytochemical profiles and anti-oxidant activities of Vitis candicans and Vitis doaniana.
- Author
-
De la Cruz AA, Hilbert G, Mengin V, Rivière C, Ollat N, Vitrac C, Bordenave L, Decroocq S, Delaunay JC, Mérillon JM, Monti JP, Gomès E, and Richard T
- Subjects
- Anthocyanins pharmacology, Antioxidants pharmacology, Chromatography, High Pressure Liquid, Free Radical Scavengers analysis, Free Radical Scavengers pharmacology, Magnetic Resonance Spectroscopy, Mass Spectrometry, Species Specificity, Vitis classification, Anthocyanins analysis, Antioxidants analysis, Vitis chemistry
- Abstract
Introduction: Grapes are one of the most important fruit crops in the world. The quality of red grape berries greatly depends on skin colour, mainly due to the anthocyanin profile. Today, the American Vitis species have the greatest potential for breeding work. They have multiple resistance properties in comparison with Vitis vinifera but little is known about their anthocyanin content., Objective: To determine the anti-oxidant properties and anthocyanin profile of two American species, Vitis candicans and Vitis doaniana, by using LC-MS(n) and LC-NMR., Methods: Grape extracts were prepared by extraction of berry skins with acidified methanol. The complete structure elucidation of the individual anthocyanins was performed with LC-MS(n) , LC-NMR and NMR experiments. Individual anthocyanins in the extracts were quantified by using malvidin glucoside as external standard. The anti-oxidant activities of grape skin extracts were evaluated by using 1,1-diphenyl-2-picrylhydrazyl (DPPH•) radical scavenging and oxygen radical absorbance capacity (ORAC) assays., Results: By using LC-MS(n) and LC-NMR experiments, 30 anthocyanins were identified and quantified in the two Vitis species, including two new cis-p-coumaroyl derivatives. Vitis candicans and V. doaniana showed significant differences in their anthocyanin profile. These two Vitis species possess low-to-medium anti-oxidant activities in comparison with V. vinifera., Conclusion: The profiles of 30 anthocyanins were established unambiguously in two American Vitis species., (Copyright © 2013 John Wiley & Sons, Ltd.)
- Published
- 2013
- Full Text
- View/download PDF
44. Inhibitory activity of plant stilbenoids against nitric oxide production by lipopolysaccharide-activated microglia.
- Author
-
Nassra M, Krisa S, Papastamoulis Y, Kapche GD, Bisson J, André C, Konsman JP, Schmitter JM, Mérillon JM, and Waffo-Téguo P
- Subjects
- Animals, Anti-Inflammatory Agents chemistry, Benzofurans chemistry, Benzofurans isolation & purification, Benzofurans pharmacology, Cell Line, Cell Survival drug effects, Lipopolysaccharides pharmacology, Microglia drug effects, Microglia metabolism, Neuroprotective Agents chemistry, Nitric Oxide metabolism, Nitric Oxide Synthase Type II drug effects, Nitric Oxide Synthase Type II genetics, Nitric Oxide Synthase Type II metabolism, Phenols chemistry, Phenols isolation & purification, Phenols pharmacology, Plant Extracts chemistry, Plant Extracts isolation & purification, Plant Extracts pharmacology, Plant Roots chemistry, Plant Stems chemistry, Polyphenols pharmacology, Stilbenes chemistry, Stilbenes isolation & purification, Anti-Inflammatory Agents pharmacology, Gnetum chemistry, Moraceae chemistry, Morus chemistry, Neuroprotective Agents pharmacology, Stilbenes pharmacology, Vitis chemistry
- Abstract
Microglia-driven inflammatory processes are thought to play an important role in ageing and several neurological disorders. Since consumption of a diet rich in polyphenols has been associated with anti-inflammatory and neuroprotective effects, we studied the effects of twenty-five stilbenoids isolated from Milicia excelsa, Morus alba, Gnetum africanum, and Vitis vinifera. These compounds were tested at 5 and 10 µM on BV-2 microglial cells stimulated with bacterial lipopolysaccharide. Ten stilbenoids reduced lipopolysaccharide-induced nitric oxide production at 5 and/or 10 µM. Two tetramers, E-vitisin A and E-vitisin B, were the most effective molecules. Moreover, they attenuated the expression of the inducible NO synthase protein and gene., (Georg Thieme Verlag KG Stuttgart · New York.)
- Published
- 2013
- Full Text
- View/download PDF
45. Dietary levels of pure flavonoids improve spatial memory performance and increase hippocampal brain-derived neurotrophic factor.
- Author
-
Rendeiro C, Vauzour D, Rattray M, Waffo-Téguo P, Mérillon JM, Butler LT, Williams CM, and Spencer JP
- Subjects
- Animals, Anthocyanins pharmacology, Blueberry Plants chemistry, Body Weight drug effects, Brain-Derived Neurotrophic Factor genetics, Feeding Behavior drug effects, Gene Expression Regulation drug effects, Hippocampus drug effects, Male, Plant Extracts pharmacology, RNA, Messenger genetics, RNA, Messenger metabolism, Rats, Rats, Wistar, Brain-Derived Neurotrophic Factor metabolism, Diet, Flavonoids pharmacology, Hippocampus metabolism, Memory drug effects
- Abstract
Evidence suggests that flavonoid-rich foods are capable of inducing improvements in memory and cognition in animals and humans. However, there is a lack of clarity concerning whether flavonoids are the causal agents in inducing such behavioral responses. Here we show that supplementation with pure anthocyanins or pure flavanols for 6 weeks, at levels similar to that found in blueberry (2% w/w), results in an enhancement of spatial memory in 18 month old rats. Pure flavanols and pure anthocyanins were observed to induce significant improvements in spatial working memory (p = 0.002 and p = 0.006 respectively), to a similar extent to that following blueberry supplementation (p = 0.002). These behavioral changes were paralleled by increases in hippocampal brain-derived neurotrophic factor (R = 0.46, p<0.01), suggesting a common mechanism for the enhancement of memory. However, unlike protein levels of BDNF, the regional enhancement of BDNF mRNA expression in the hippocampus appeared to be predominantly enhanced by anthocyanins. Our data support the claim that flavonoids are likely causal agents in mediating the cognitive effects of flavonoid-rich foods.
- Published
- 2013
- Full Text
- View/download PDF
46. Chemical dereplication of wine stilbenoids using high performance liquid chromatography-nuclear magnetic resonance spectroscopy.
- Author
-
Pawlus AD, Cantos-Villar E, Richard T, Bisson J, Poupard P, Papastamoulis Y, Monti JP, Teissedre PL, Waffo-Téguo P, and Mérillon JM
- Subjects
- Mass Spectrometry, Chromatography, High Pressure Liquid methods, Magnetic Resonance Spectroscopy methods, Stilbenes analysis, Wine analysis
- Abstract
Wine is a major dietary source of numerous potentially health promoting stilbenoids that have been the subject of many qualitative and quantitative studies. However, our initial HPLC-MS analyses of crude wine samples demonstrated the presence of compounds with molecular weights matching characteristic stilbenoid dimers, trimers, and tetramers that were unaccounted for in the literature. Due to the likelihood that these are known compounds, a chemical dereplication method is highly desirable. We developed such a method using LC-DAD-MS monitored fractionation steps, using adsorption and centrifugal partition chromatography (CPC), to obtain fractions rich in stilbenoids for analysis in stopped-flow LC-NMR. (1)H NMR spectra and MS data were cross-referenced with our laboratory database and the literature for identification. This method yielded highly useful structural information, allowing the characterization of previously unidentified stilbenoids in wine, ampelopsin C, isohopeaphenol, quadrangularin A, and E-ω-viniferin. These results demonstrate the usefulness of stop-flow LC-NMR in conjunction with LC-MS guided fractionation for the dereplication of compounds of interest in general, and specifically for expanding the current knowledge of wine chemistry., (Copyright © 2013 Elsevier B.V. All rights reserved.)
- Published
- 2013
- Full Text
- View/download PDF
47. Identification and quantification of furanocoumarins in stem bark and wood of eight Algerian varieties of Ficus carica by RP-HPLC-DAD and RP-HPLC-DAD-MS.
- Author
-
Rouaiguia-Bouakkaz S, Amira-Guebailia H, Rivière C, Delaunay JC, Waffo-Téguo P, and Mérillon JM
- Subjects
- Algeria, Plant Bark chemistry, Plant Stems chemistry, Chromatography, High Pressure Liquid methods, Ficus chemistry, Furocoumarins analysis
- Abstract
Furanocoumarins are the major phytoalexins of Ficus carica and are effective natural drug candidates for treatment of several types of cancer and skin disease. The objectives of this study were to analyze and quantify linear furanocoumarins, mainly psoralen and bergapten, in wood and bark of stems from eight Algerian varieties of fig and to establish the differences in the content of these metabolites in the eight local samples. Psoralen and bergapten contents in the stem bark and wood (in microg/g DW) varied respectively from 146.6 to 1110.3 and from 395.7 to 1671.8 for psoralen, and from 114.3 to 524.0 and from 144.2 to 718.6 for bergapten. This study fills a gap in our knowledge of furanocoumarin distribution in different parts of the fig tree. Psoralen and bergapten concentrations were higher in the wood than in the stem bark. Most of the dark fruited fig trees produce these two coumarins more than the green ones.
- Published
- 2013
48. Stilbenoid profiles of canes from Vitis and Muscadinia species.
- Author
-
Pawlus AD, Sahli R, Bisson J, Rivière C, Delaunay JC, Richard T, Gomès E, Bordenave L, Waffo-Téguo P, and Mérillon JM
- Subjects
- Benzofurans chemistry, Chromatography, High Pressure Liquid, Flavonoids chemistry, Glucosides chemistry, Magnetic Resonance Spectroscopy, Phenols chemistry, Resveratrol, Vitis classification, Stilbenes chemistry, Vitis chemistry
- Abstract
We present stilbenoid profiles of canes from 16 grapevines. Fifteen stilbenoids were obtained through isolation and structure identification using MS, NMR, and [α](D) or as commercial standards. An HPLC-UV method for the simultaneous quantification of nine of these stilbenoids was developed and applied to canes of Vitis amurensis, Vitis arizonica, Vitis berlandieri, Vitis betulifolia, Vitis cinerea, Vitis × champini, Vitis × doaniana, Vitis labrusca, Vitis candicans (syn. Vitis mustangensis), Vitis riparia, Vitis rupestris, Vitis vinifera, Muscadinia rotundifolia, and a V. vinifera × M. rotundifolia hybrid. In these species, E-ampelopsin E, E-amurensin B, E-piceid, E-piceatannol, E-resveratrol, E-resveratroloside, E-ε-viniferin, E-ω-viniferin, and E-vitisin B were quantified, when found in sufficient amounts. Total concentrations ranged from ~2.2 to 19.5 g/kg of dry weight. Additional stilbenoids, E-3,5,4'-trihydroxystilbene 2-C-glucoside, Z-ampelopsin E, Z-trans-miyabenol C, E-trans-miyabenol C, scirpusin A, and Z-vitisin B, were identified but not quantified. Our results indicate that canes, particularly those of non-vinifera species, have substantial quantities of valuable, health-promoting stilbenoids.
- Published
- 2013
- Full Text
- View/download PDF
49. Phenolics and their antifungal role in grapevine wood decay: focus on the Botryosphaeriaceae family.
- Author
-
Lambert C, Bisson J, Waffo-Téguo P, Papastamoulis Y, Richard T, Corio-Costet MF, Mérillon JM, and Cluzet S
- Subjects
- Benzofurans pharmacology, Host-Pathogen Interactions physiology, Inhibitory Concentration 50, Stilbenes analysis, Stilbenes metabolism, Stilbenes pharmacology, Wine, Wood microbiology, Antifungal Agents pharmacology, Ascomycota drug effects, Ascomycota pathogenicity, Phenols pharmacology, Plant Diseases microbiology, Plant Stems microbiology, Vitis microbiology
- Abstract
The interaction between Vitis vinifera and trunk disease fungi requires better understanding. We studied the role of phenolics as possible plant defense compounds in this context. The impact of 24 grapevine phenolic compounds was determined on 6 major wood decay fungi by an in vitro agar plate assay. Hydroxystilbenoids, especially oligomers such as miyabenol C, isohopeaphenol, and vitisin A and B, greatly reduced the growth of the fungi, except that of Phaeoacremonium aleophilum . A detailed investigation in 10 Botryosphaeriaceae strains revealed that all of the studied members of this family display a common susceptibility to phenolics that is more or less significant. Then we undertook a quantitative analysis of stilbenoid content in grapevine plantlets inoculated with Botryosphaeriaceae to investigate whether in planta these fungi have to counteract the most active phenolics. On the basis of our results, the possible role of phenolics in grapevine defense against trunk disease agents is discussed.
- Published
- 2012
- Full Text
- View/download PDF
50. Isolation of powerful antioxidants from the medicinal halophyte Limoniastrum guyonianum.
- Author
-
Trabelsi N, Oueslati S, Falleh H, Waffo-Téguo P, Papastamoulis Y, Mérillon JM, Abdelly C, and Ksouri R
- Subjects
- Antioxidants chemistry, Arizona, Plant Extracts chemistry, Plants, Medicinal genetics, Plumbaginaceae genetics, Salt-Tolerant Plants, Antioxidants isolation & purification, Plant Extracts isolation & purification, Plants, Medicinal chemistry, Plumbaginaceae chemistry
- Abstract
The antioxidant capacities of the crude extract, aqueous and ethyl acetate partitions of Limoniastrum guyonianum Boiss. (Zita) were investigated in this study. The ethyl acetate phase exhibited a significant antioxidant activity as judged by total antioxidant activity, DPPH test and reducing power. Fractionation of this extract by centrifugal partition chromatography (CPC) using quaternary Arizona solvent systems composed of n-heptane/ethyl acetate/methanol/water led to ten fractions. The antioxidant capacities of these fractions were assessed using the same previous tests. Fraction 8 showed the highest antioxidant capacity (1291.1mg GAE/g DR), the power ability to quench DPPH radical (IC(50)=2μg/ml) and to reduce Fe(3+) (EC(50)=65μg/ml). From this fraction, three powerful flavonoids were isolated (1-3): gallocatechin (1), epigallocatechin (2) and epigallocatechin-3-O-gallate (3). These findings suggest that the antioxidative property of L. guynianum is may be related to the presence of these flavonoids, which can be used in various industrial fields., (Copyright © 2012 Elsevier Ltd. All rights reserved.)
- Published
- 2012
- Full Text
- View/download PDF
Catalog
Discovery Service for Jio Institute Digital Library
For full access to our library's resources, please sign in.