Article
Biochemistry & Molecular Biology
Biranty Sy, Stephanie Krisa, Tristan Richard, Arnaud Courtois
Summary: The control of oxidative stress with natural active substances is important in limiting the development of diseases. Resveratrol showed the highest antiradical activity among the tested substances, followed by epsilon-viniferin and vitisin B. Different combinations of these substances displayed additive or synergistic effects, depending on the assay method used.
Article
Agriculture, Multidisciplinary
Ru Wang, Sangram Keshari Lenka, Varun Kumar, Kelem Gashu, Noga Sikron-Persi, Irena Dynkin, David Weiss, Avichai Perl, Aaron Fait, Michal Oren-Shamir
Summary: The study focuses on enhancing the production of stilbenes, specifically the resveratrol dehydrodimer viniferin, by overexpressing stilbene synthase (STS) and providing ample phenylalanine (Phe). Results show that this strategy significantly increases the accumulation of resveratrol and viniferin in plant cell cultures.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2021)
Article
Plant Sciences
Henrique Noronha, Angelica Silva, Virginie Garcia, Kevin Billet, Alberto C. P. Dias, Arnaud Lanoue, Philippe Gallusci, Hernani Geros
Summary: Stilbenoids, important phenylpropanoid compounds synthesized in grapevine in response to stress, have been mainly described in berries. However, this study shows that they can also accumulate in the woody canes during bud burst, and their accumulation is correlated with the increased expression of stilbene synthase genes and the transcription factor VviMYB14. Additionally, there is a general stimulation of the plastidial shikimate pathway.
Article
Agriculture, Multidisciplinary
Paul Besrukow, Jan Irmler, Joachim Schmid, Manfred Stoll, Peter Winterhalter, Ralf Schweiggert, Frank Will
Summary: This study reveals the variability of stilbenoid levels in grape cane, which is influenced by genetic and environmental factors. Different grape varieties and vineyard positions contribute to the variation in stilbenoid levels, and there are also pronounced differences among samples from different years.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Qibin Zhu, Binhao Teng, Ying Chen, Fubao Su, Yanqiu Li, Qingyun Yang, Chunsuo Yao
Summary: A concise and efficient procedure for the total synthesis of natural stilbene dimer (+/-)-epsilon-viniferin was accomplished with high overall yield.
Article
Agriculture, Multidisciplinary
Julien Gabaston, Thierry Buffeteau, Agnes Destrac Irvine, Gregory Gambetta, Jean-Michel Merillon, Pierre Waffo-Teguo
Summary: The accurate identification of grapevine cultivars is crucial, and various tools, including E-ε-viniferin, have been developed. The enantiomeric excess of E-ε-viniferin serves as a chemical marker to distinguish grape varieties and establish cultivar relationships through statistical analysis.
JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE
(2023)
Article
Medicine, Research & Experimental
Jeongyoon Choi, Sung-Yun Choi, Yuni Hong, Young-Eun Han, Soo-Jin Oh, Bonggi Lee, Chun Whan Choi, Min Soo Kim
Summary: This study investigated the pharmaceutical effects of vitisin A on cognitive functions using in vitro, ex vivo, and in vivo experiments. The results showed that vitisin A increased cell viability, restored disrupted long-term potentiation, and ameliorated cognitive and memory functions in mice. Further studies revealed that vitisin A upregulated BDNF-CREB signaling.
BIOMEDICINE & PHARMACOTHERAPY
(2023)
Review
Food Science & Technology
Nawel Benbouguerra, Ruth Hornedo-Ortega, Francois Garcia, Toni El Khawand, Cedric Saucier, Tristan Richard
Summary: Stilbenes are natural phenolic compounds synthesized by plants in response to stress. They are found in grape berries and wine, with potential anti-obesity effects. Optimized analytical methods are essential for accurate detection and quantification of stilbenes.
TRENDS IN FOOD SCIENCE & TECHNOLOGY
(2021)
Review
Biochemistry & Molecular Biology
Pauline Beaumont, Arnaud Courtois, Claude Atgie, Tristan Richard, Stephanie Krisa
Summary: Stilbenes, such as ε-viniferin, exhibit anti-inflammatory and anti-oxidative stress activities. Despite its low bioavailability and high metabolism, multiple studies have shown its potential therapeutic effects on various diseases. ε-viniferin could be a promising candidate for future functional foods or supplement foods used for the management of chronic diseases.
JOURNAL OF PHYSIOLOGY AND BIOCHEMISTRY
(2022)
Article
Nutrition & Dietetics
Pauline Beaumont, Chrystel Faure, Arnaud Courtois, Michael Jourdes, Axel Marchal, Pierre-Louis Teissedre, Tristan Richard, Claude Atgie, Stephanie Krisa
Summary: The encapsulation of ε Vin did not significantly alter its pharmacokinetic parameters, but did lead to a notable increase in the half-life of ε VG. Both ε Vin and ε VG were found to accumulate in adipose tissues, with a significant increase in the latter in mesenteric tissue after encapsulation.
Article
Food Science & Technology
C. Medrano-Padial, A. Prieto, M. Puerto, S. Pichardo
Summary: Stilbenes are secondary metabolites produced by plants with important bioactive properties, and are considered as a natural alternative in the wine industry. Despite controversy over the toxicological information on stilbenes, this study found low genotoxicity in in vitro tests, suggesting potential safe use as a product.
FOOD AND CHEMICAL TOXICOLOGY
(2021)
Article
Biochemistry & Molecular Biology
Yuni Hong, Yun-Hyeok Choi, Young-Eun Han, Soo-Jin Oh, Ansoo Lee, Bonggi Lee, Rebecca Magnan, Shi Yong Ryu, Chun Whan Choi, Min Soo Kim
Summary: Ampelopsin A, a major compound found in Vitis vinifera, has been shown to have neuroprotective effects and improve memory impairments caused by hippocampal damage.
Article
Biochemistry & Molecular Biology
Hsiang-Ruei Liao, Chin-Hsuan Lin, Jih-Jung Chen, Fu-Chao Liu, Ching-Ping Tseng
Summary: Epsilon-viniferin inhibits the respiratory burst induced by fMLP in human neutrophils by antagonizing formyl peptide receptor 1 in a reversible and non-competitive manner.
CHEMICO-BIOLOGICAL INTERACTIONS
(2021)
Article
Food Science & Technology
Mirella Noviello, Antonio Francesco Caputi, Giacomo Squeo, Vito Michele Paradiso, Giuseppe Gambacorta, Francesco Caponio
Summary: Vine shoots, a common winery waste, can be a source of bioactive compounds such as stilbenes. The study found that heat treatments had a slight impact on stilbene content, while the variety of vine shoots had a stronger influence.
Article
Biochemistry & Molecular Biology
Ting Zhao, Congbo Huang, Shengzhi Li, Mengqiong Jia, Ling Wang, Yujin Tang, Chaohong Zhang, Yan Li
Summary: In this study, a grape F-box E3 ubiquitin ligase VviKFB07 associated with the metabolism of stilbene and flavonoid was identified. Overexpression of VviKFB07 led to a decrease in flavonol and anthocyanin content in corolla and promoted the accumulation of resveratrol in grape callus. Further experiments confirmed the physical interaction between VviKFB07 and VviCHSs proteins and the involvement of VviKFB07 in the ubiquitination and degradation of VviCHSs protein. These findings clarify the role of ubiquitin ligase VviKFB07 in the synthesis of stilbene and flavonoid in grapes.
Article
Plant Sciences
Robin Huber, Laurence Marcourt, Alexey Koval, Sylvain Schnee, Davide Righi, Emilie Michellod, Vladimir L. Katanaev, Jean-Luc Wolfender, Katia Gindro, Emerson Ferreira Queiroz
Summary: A series of complex phenylpropanoid derivatives were obtained by chemoenzymatic biotransformation. These compounds showed anti-Wnt activity and have potential applications.
FRONTIERS IN PLANT SCIENCE
(2022)
Article
Chemistry, Organic
Laurence Marcourt, Georges Massiot
Summary: Hemicalide is a marine natural product with unique cytotoxicity, isolated from a sponge in Vanuatu, and its planar structure has been determined by 2D-NMR experiments. The molecule belongs to the polyketide class and has unusual hydroxylated six-membered ring lactones.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Robin Huber, Laurence Marcourt, Luis-Manuel Quiros-Guerrero, Alexandre Luscher, Sylvain Schnee, Emilie Michellod, Verena Ducret, Thilo Kohler, Karl Perron, Jean-Luc Wolfender, Katia Gindro, Emerson Ferreira Queiroz
Summary: A series of complex stilbene dimers were generated through biotransformation of resveratrol, pterostilbene, and their mixture using the enzymatic secretome of Botrytis cinerea Pers. The study isolated enantiomers to determine their absolute configuration and assess the potential impact of stereochemistry on biological properties. The antibacterial activities of the compounds against methicillin-resistant strains of Staphylococcus aureus were evaluated, showing the importance of stereochemistry in their biological effects.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Robin Huber, Alexey Koval, Laurence Marcourt, Margaux Heritier, Sylvain Schnee, Emilie Michellod, Leonardo Scapozza, Vladimir L. Katanaev, Jean-Luc Wolfender, Katia Gindro, Emerson Ferreira Queiroz
Summary: The study obtained a library of complex stilbene derivatives through biotransformation, and comprehensively quantified their inhibitory activity against the oncogenic Wnt pathway. The structure-activity relationships and mechanistic details of these compounds were revealed, providing insights for potential therapeutically relevant compounds targeting this pathway.
FRONTIERS IN CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jean-Luc Wolfender, Arnaud Gaudry, Adriano Rutz, Luis-Manuel Quiros-Guerrero, Louis-Felix Nothias, Emerson Ferreira Queiroz, Emmanuel Defossez, Pierre-Marie Allard
Summary: Metabolomics plays a significant role in chemical ecology and the identification of bioactive natural products. The annotation process of specialized metabolome has improved with advanced analytical techniques, such as LC-MS.
Article
Biochemistry & Molecular Biology
Adrianna Skiba, Ewelina Koziol, Simon Vlad Luca, Barbara Budzynska, Piotr Podlasz, Wietske Van Der Ent, Elham Shojaeinia, Camila V. V. Esguerra, Mohammed Nour, Laurence Marcourt, Jean-Luc Wolfender, Krystyna Skalicka-Wozniak
Summary: Epilepsy affects over 50 million people globally and 30% of patients do not respond to available treatment. Herbal medicines may provide new antiseizure drugs. This study found that the crude leaf extract of Halfordia kendack Guillaumin significantly reduced seizure-like behavior in zebrafish with induced acute seizures. A compound called halfordin was isolated from the extract and showed potential antiseizure effects in locomotor and local field potential analysis, as well as gene expression modulation.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Agriculture, Multidisciplinary
Luiz Leonardo Saldanha, Pierre-Marie Allard, Guilherme Dilarri, Santiago Codesido, Victor Gonzalez-Ruiz, Emerson Ferreira Queiroz, Henrique Ferreira, Jean-Luc Wolfender
Summary: This study investigated the chemical responses of Citrus leaves to Xanthomonas citri infection using a mass spectrometry-based metabolomic approach. It was found that the tryptophan metabolism pathway in Citrus leaves was activated, leading to the accumulation of N-methylated tryptamine derivatives. Additionally, several tryptamine derivatives showed inhibitory effects in vitro against X. citri.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Antonina Klimenko, Robin Huber, Laurence Marcourt, Dmitry Tabakaev, Alexey Koval, Salim Sh. Dautov, Tatyana N. N. Dautova, Jean-Luc Wolfender, Rob Thew, Yuri Khotimchenko, Emerson Ferreira Queiroz, Vladimir L. L. Katanaev
Summary: Through metabolite analysis, we have identified five new chlorin compounds from Ophiura sarsii and O. ooplax, demonstrating their potential applications in photodynamic therapy.
Article
Biochemistry & Molecular Biology
Luis-Manuel Quiros-Guerrero, Louis-Felix Nothias, Arnaud Gaudry, Laurence Marcourt, Pierre-Marie Allard, Adriano Rutz, Bruno David, Emerson Ferreira Queiroz, Jean-Luc Wolfender
Summary: Collections of natural extracts have the potential to discover novel natural products, but the prioritization of extracts remains challenging. Inventa is a computational tool that considers mass spectrometry data, spectral annotation, and literature reports to highlight the structural novelty potential within extracts. Application of Inventa to plants from the Celastraceae family identified the roots extract of Pristimera indica as a promising source of potentially novel compounds.
FRONTIERS IN MOLECULAR BIOSCIENCES
(2022)
Article
Microbiology
Alexandre Le Loarer, Remy Marcellin-Gros, Laurent Dufosse, Jerome Bignon, Michel Frederich, Allison Ledoux, Emerson Ferreira Queiroz, Jean-Luc Wolfender, Anne Gauvin-Bialecki, Mireille Fouillaud
Summary: Despite advances in medicine and technology, deadly diseases are still a threat to humanity. To find effective treatments, research is focusing on unexplored habitats with unique biodiversity, such as the marine environment. Studies have shown the potential of bioactive compounds from marine organisms in treating diseases.
Article
Plant Sciences
Hugo Morin, Aurore Chetelat, Stephanie Stolz, Laurence Marcourt, Gaetan Glauser, Jean-Luc Wolfender, Edward E. Farmer
Summary: The connections between wound-response electrical signaling and jasmonate synthesis activation are not known. This study investigated the remodeling of jasmonate precursor pools in the leaf vasculature of Arabidopsis thaliana in response to injury. Metabolomics and NMR were used to analyze galactolipids and jasmonate precursors in undamaged and wounded plants, while DAD1-LIKE LIPASEs (DALLs) that regulate these precursor levels were identified. The study found a novel galactolipid, sn-2-OPDA-MGMG, containing the jasmonate precursor 12-oxo-phytodienoic acid (OPDA), in the veins. It was discovered that electrical signals triggered a rapid reduction of vascular OPDA-MGMGs, sn-2-OPDA-MGMG, and free OPDA pools. In mutant plants with reduced DALL2 function, there was a failure to build resting vascular sn-2-OPDA-MGMG and OPDA pools, resulting in less production of jasmonoyl-isoleucine (JA-Ile) upon wounding. DALL3 acted to suppress excessive JA-Ile production, while dall2 dall3 double mutants greatly reduced jasmonate signaling in leaves distal to wounds.
Article
Plant Sciences
Yong-Qiang Gao, Hugo Morin, Laurence Marcourt, Tsu-Hao Yang, Jean-Luc Wolfender, Edward E. Farmer
Summary: Ricca assays allow the direct introduction of compounds extracted from plants or organisms into the leaf vasculature, enabling the study of plant responses to external stimuli. This study identifies glutamate as the most active elicitor of membrane depolarization and reveals a potential link between GSL breakdown and glutathione in the generation of membrane depolarizing signals. It also suggests that chloride ions may play a role in wound-response membrane potential changes.
Article
Agriculture, Multidisciplinary
Adriano Rutz, Jean-Luc Wolfender
Summary: Recent developments in mass spectrometry-based metabolite profiling have allowed for unprecedented qualitative coverage of complex biological extract composition. However, the use of electrospray ionization in metabolite profiling leads to multiple artifactual signals for a single analyte. In this study, we developed a generic qualitative and quantitative approach using a combination of liquid chromatography-mass spectrometry (LC-MS) and Charged Aerosol Detection (CAD) to annotate and contextualize features in a high-resolution tandem MS dataset. Signals not attributed to CAD peaks are considered minor metabolites. This approach enables the automatic assessment of the composition of single natural extracts or broader collections, facilitating new ingredient registrations or natural-extracts-based drug discovery campaigns.
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
(2023)
