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Article ; Online: Semi-synthesis, α-amylase inhibition, and kinetic and molecular docking studies of arylidene-based sesquiterpene coumarins isolated from

Baccari, Wiem / Saidi, Ilyes / Filali, Insaf / Znati, Mansour / Lazrag, Houda / Tounsi, Moncef / Marchal, Axel / Waffo-Teguo, Pierre / Ben Jannet, Hichem

RSC advances

2024 Volume 14, Issue 7, Page(s) 4654–4665

Abstract: Despite all the significant progresses made to enhance the efficacy of the existing bank of drugs used to manage and cure type II diabetes mellitus, there is still a need to search and develop novel bioactive compounds with superior efficacy and minimal ... ...

Abstract	Despite all the significant progresses made to enhance the efficacy of the existing bank of drugs used to manage and cure type II diabetes mellitus, there is still a need to search and develop novel bioactive compounds with superior efficacy and minimal adverse effects. This study describes the valorization of the natural bioactive sesquiterpene coumarin
Language	English
Publishing date	2024-02-05
Publishing country	England
Document type	Journal Article
ISSN	2046-2069
ISSN (online)	2046-2069
DOI	10.1039/d3ra07540k
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Article ; Online: Targeting of Antifungal Metabolites from Grapevine Byproducts by UPLC-HRMS/MS Approaches Using Bioactivity-Based Molecular Networking.

Tardif, Charles / Rouger, Caroline / Miranda, Julie / Ahmed, Omar S / Richard-Forget, Florence / Atanasova, Vessela / Waffo-Teguo, Pierre

Journal of agricultural and food chemistry

2024 Volume 72, Issue 17, Page(s) 9621–9636

Abstract: This study focuses on ... ...

Abstract	This study focuses on countering
MeSH term(s)	Vitis/chemistry ; Vitis/microbiology ; Fusarium/drug effects ; Fusarium/growth & development ; Tandem Mass Spectrometry ; Chromatography, High Pressure Liquid ; Plant Extracts/pharmacology ; Plant Extracts/chemistry ; Fungicides, Industrial/pharmacology ; Fungicides, Industrial/chemistry ; Plant Diseases/microbiology ; Waste Products/analysis
Chemical Substances	Plant Extracts ; Fungicides, Industrial ; Waste Products
Language	English
Publishing date	2024-04-22
Publishing country	United States
Document type	Journal Article
ZDB-ID	241619-0
ISSN	1520-5118 ; 0021-8561
ISSN (online)	1520-5118
ISSN	0021-8561
DOI	10.1021/acs.jafc.3c09531
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Article ; Online: Chiral analysis of E-ε-viniferin enantiomers, towards a new chemotaxonomic marker of the vine.

Gabaston, Julien / Buffeteau, Thierry / Irvine, Agnès Destrac / Gambetta, Gregory / Mérillon, Jean-Michel / Waffo-Téguo, Pierre

Journal of the science of food and agriculture

2023 Volume 103, Issue 5, Page(s) 2295–2303

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. ... ...

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.
MeSH term(s)	Stilbenes/analysis ; Vitis/chemistry ; Wine/analysis ; Benzofurans/analysis
Chemical Substances	epsilon-viniferin (62218-08-0) ; Stilbenes ; Benzofurans
Language	English
Publishing date	2023-01-22
Publishing country	England
Document type	Journal Article
ZDB-ID	184116-6
ISSN	1097-0010 ; 0022-5142
ISSN (online)	1097-0010
ISSN	0022-5142
DOI	10.1002/jsfa.12444
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Article ; Online: An automated accelerated salting-out assisted solvent extraction (A-ASASE) of stilbenoids from Vitis vinifera L. branches: False proof or a proof of concept?

Ahmed, Omar S / Tahanout, Faiza / Marti-Mestres, Gilberte / Weber, Jean-Frédéric / Waffo-Téguo, Pierre

Talanta

2023 Volume 266, Issue Pt 1, Page(s) 124935

Abstract: An automated accelerated salting-out assisted solvent extraction (A-ASASE) was developed. This approach made full use of the advantages of both the accelerated solvent extraction (ASE) technique and salting-out assisted liquid-liquid extraction (SALLE), ... ...

Abstract	An automated accelerated salting-out assisted solvent extraction (A-ASASE) was developed. This approach made full use of the advantages of both the accelerated solvent extraction (ASE) technique and salting-out assisted liquid-liquid extraction (SALLE), without any modifications at the level of the ASE machine. The A-ASASE combined an automated extraction at high temperature/pressure and an enrichment step using eco-friendly solvents (e.g., water and ethanol) in a fully integrated and simple way that required only low volumes of solvents. The A-ASASE was successfully applied to extract three stilbenoids, namely E-resveratrol, E-ε-viniferin and E-vitisin B, present in grapevine (Vitis vinifera L.) by-products as a proof-of-concept compound. First, factors affecting the yield of stelbenoids by SALLE were investigated by means of a design of experiment model (DOE). The SALLE was then incorporated into ASE. Various ASE operational parameters such as temperature and number of cycles were also investigated. The highest yield was obtained using a mixture of ethanol-water, 70:30 (v/v) at 60 °C, using three extraction cycles and with 5 min of contact each. The highest yields of stilbenoids were 5.87 ± 0.28 g kg
MeSH term(s)	Resveratrol ; Vitis ; Solvents ; Water ; Stilbenes ; Sodium Chloride ; Liquid-Liquid Extraction/methods ; Ethanol ; Chromatography, High Pressure Liquid
Chemical Substances	malvidin-3-O-glucoside-4 vinyl ; Resveratrol (Q369O8926L) ; epsilon-viniferin (62218-08-0) ; Solvents ; Water (059QF0KO0R) ; Stilbenes ; Sodium Chloride (451W47IQ8X) ; Ethanol (3K9958V90M)
Language	English
Publishing date	2023-07-22
Publishing country	Netherlands
Document type	Journal Article
ZDB-ID	1500969-5
ISSN	1873-3573 ; 0039-9140
ISSN (online)	1873-3573
ISSN	0039-9140
DOI	10.1016/j.talanta.2023.124935
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Article ; Online: Chiral analysis of E‐ε‐viniferin enantiomers, towards a new chemotaxonomic marker of the vine

Gabaston, Julien / Buffeteau, Thierry / Irvine, Agnès Destrac / Gambetta, Gregory / Mérillon, Jean‐Michel / Waffo‐Téguo, Pierre

Journal of the Science of Food and Agriculture. 2023 Mar. 30, v. 103, no. 5 p.2295-2303

2023

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. ... ...

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.
Keywords	Vitis vinifera ; agriculture ; chemotaxonomy ; cultivars ; economic systems ; enantiomers ; grapes ; high performance liquid chromatography ; phenotype ; statistical analysis ; stilbenes ; vines ; wines
Language	English
Dates of publication	2023-0330
Size	p. 2295-2303.
Publishing place	John Wiley & Sons, Ltd.
Document type	Article ; Online
Note	JOURNAL ARTICLE
ZDB-ID	184116-6
ISSN	1097-0010 ; 0022-5142
ISSN (online)	1097-0010
ISSN	0022-5142
DOI	10.1002/jsfa.12444
Database	NAL-Catalogue (AGRICOLA)

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Article ; Online: Understanding sweetness of dry wines: First evidence of astilbin isomers in red wines and quantitation in a one-century range of vintages.

Fayad, Syntia / Le Scanff, Marie / Waffo-Teguo, Pierre / Marchal, Axel

Food chemistry

2021 Volume 352, Page(s) 129293

Abstract: Astilbin (2R, 3R) was recently reported to contribute to wine sweetness. As its aglycon contains two stereogenic centers, three other stereoisomers may be present: neoisoastilbin (2S, 3R), isoastilbin (2R, 3S), and neoastilbin (2S, 3S). This work aimed ... ...

Abstract	Astilbin (2R, 3R) was recently reported to contribute to wine sweetness. As its aglycon contains two stereogenic centers, three other stereoisomers may be present: neoisoastilbin (2S, 3R), isoastilbin (2R, 3S), and neoastilbin (2S, 3S). This work aimed at assaying their presence for the first time in wines as well as their taste properties. The isomers were synthesized from astilbin and purified by semi-preparative HPLC. With the four stereoisomers, a sweet taste was perceived whose intensity varied with the configuration. Their content was assayed by developing a UHPLC-Q-Exactive method. The method was applied to screen astilbin and isomers in various wines, especially in different vintages from the same estate. While young wines contained higher concentrations of astilbin than the old ones, the concentrations of the other isomers, mainly neoastilbin, were higher in the old wines, suggesting their formation over time.
MeSH term(s)	Flavonols/analysis ; Flavonols/chemistry ; Humans ; Isomerism ; Taste ; Time Factors ; Wine/analysis
Chemical Substances	Flavonols ; astilbin (29838-67-3)
Language	English
Publishing date	2021-02-15
Publishing country	England
Document type	Journal Article
ZDB-ID	243123-3
ISSN	1873-7072 ; 0308-8146
ISSN (online)	1873-7072
ISSN	0308-8146
DOI	10.1016/j.foodchem.2021.129293
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Article: Naturally occurring phenolic compounds as promising antimycotoxin agents: Where are we now?

Ahmed, Omar S. / Tardif, Charles / Rouger, Caroline / Atanasova, Vessela / Richard‐Forget, Florence / Waffo‐Téguo, Pierre

Comprehensive reviews in food science and food safety. 2022 Mar., v. 21, no. 2

2022

Abstract: Mycotoxins are metabolites produced by molds that contaminate food commodities, are harmful to both humans and animals, as well as cause economic losses. Many countries have set regulatory limits and strict thresholds to control the level of mycotoxins ... ...

Abstract	Mycotoxins are metabolites produced by molds that contaminate food commodities, are harmful to both humans and animals, as well as cause economic losses. Many countries have set regulatory limits and strict thresholds to control the level of mycotoxins in food and feedstuffs. New technologies and strategies have been developed to inhibit toxigenic fungal invasion and to decontaminate mycotoxins. However, many of these strategies do not sufficiently detoxify mycotoxins and leave residual toxic by‐products. This review focuses on the use of phenolic compounds obtained from botanical extracts as promising bioagents to inhibit fungal growth and/or to limit mycotoxin yields. The mechanism of these botanicals, legislation concerning their use, and their safety are also discussed. In addition, recent strategies to overcome stability and solubility constraints of phenolic compounds to be used in food and feed stuffs are also mentioned.
Keywords	biological control agents ; decontamination ; feeds ; food safety ; fungal growth ; fungi ; laws and regulations ; metabolites ; mycotoxins ; solubility ; toxicity
Language	English
Dates of publication	2022-03
Size	p. 1161-1197.
Publishing place	John Wiley & Sons, Ltd
Document type	Article
Note	JOURNAL ARTICLE
ZDB-ID	2185829-9
ISSN	1541-4337
ISSN	1541-4337
DOI	10.1111/1541-4337.12891
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Article ; Online: Untargeted LC-HRMS profiling followed by targeted fractionation to discover new taste-active compounds in spirits.

Winstel, Delphine / Bahammou, Delphine / Albertin, Warren / Waffo-Téguo, Pierre / Marchal, Axel

Food chemistry

2021 Volume 359, Page(s) 129825

Abstract: Taste is a key driver of food and beverage acceptability due to its role in consumers' pleasure. The great interest that natural food and beverages now arouse lies notably in the complexity of their taste, which in turn is related to a wide range of ... ...

Abstract	Taste is a key driver of food and beverage acceptability due to its role in consumers' pleasure. The great interest that natural food and beverages now arouse lies notably in the complexity of their taste, which in turn is related to a wide range of taste-active compounds. Going beyond the classic divide between targeted and untargeted strategies, an integrative methodology to spirits was applied. Untargeted profiling of several cognac spirits was implemented by LC-HRMS to identify compounds of interest among hundreds of ions. A targeted fractionation protocol was then developed. By using HRMS and NMR, dihydrodehydrodiconiferyl alcohol was identified and described for the first time in spirits and oak wood. It was characterized as sweet at 2 mg/L in two matrices and was quantified in spirits up to 4 mg/L. These findings demonstrated how this methodology is relevant and effective to discover new taste-active compounds.
MeSH term(s)	Alcoholic Beverages/analysis ; Chemical Fractionation ; Chromatography, Liquid ; Food Analysis/methods ; Humans ; Mass Spectrometry ; Quercus/chemistry ; Taste ; Wood/chemistry
Language	English
Publishing date	2021-04-20
Publishing country	England
Document type	Journal Article
ZDB-ID	243123-3
ISSN	1873-7072 ; 0308-8146
ISSN (online)	1873-7072
ISSN	0308-8146
DOI	10.1016/j.foodchem.2021.129825
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Article ; Online: Naturally occurring phenolic compounds as promising antimycotoxin agents: Where are we now?

Ahmed, Omar S / Tardif, Charles / Rouger, Caroline / Atanasova, Vessela / Richard-Forget, Florence / Waffo-Téguo, Pierre

Comprehensive reviews in food science and food safety

2022 Volume 21, Issue 2, Page(s) 1161–1197

Abstract	Mycotoxins are metabolites produced by molds that contaminate food commodities, are harmful to both humans and animals, as well as cause economic losses. Many countries have set regulatory limits and strict thresholds to control the level of mycotoxins in food and feedstuffs. New technologies and strategies have been developed to inhibit toxigenic fungal invasion and to decontaminate mycotoxins. However, many of these strategies do not sufficiently detoxify mycotoxins and leave residual toxic by-products. This review focuses on the use of phenolic compounds obtained from botanical extracts as promising bioagents to inhibit fungal growth and/or to limit mycotoxin yields. The mechanism of these botanicals, legislation concerning their use, and their safety are also discussed. In addition, recent strategies to overcome stability and solubility constraints of phenolic compounds to be used in food and feed stuffs are also mentioned.
MeSH term(s)	Animals ; Food Contamination/analysis ; Food Contamination/prevention & control ; Fungi ; Mycotoxins/analysis
Chemical Substances	Mycotoxins
Language	English
Publishing date	2022-01-29
Publishing country	United States
Document type	Journal Article ; Review
ZDB-ID	2185829-9
ISSN	1541-4337 ; 1541-4337
ISSN (online)	1541-4337
ISSN	1541-4337
DOI	10.1111/1541-4337.12891
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Article ; Online: 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.

Auberon, Florence / Olatunji, Opeyemi Joshua / Waffo-Teguo, Pierre / Olatunde, Oladipupo Odunayo / Singh, Sudarshan / Bonté, Frédéric / Mérillon, Jean-Michel / Lobstein, Annelise

Phytochemistry

2022 Volume 206, Page(s) 113504

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 ...

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.
Language	English
Publishing date	2022-11-18
Publishing country	England
Document type	Journal Article
ZDB-ID	208884-8
ISSN	1873-3700 ; 0031-9422
ISSN (online)	1873-3700
ISSN	0031-9422
DOI	10.1016/j.phytochem.2022.113504
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