- A focused multiple reaction monitoring (MRM) quantitative method for bioactive grapevine stilbenes by ultra-high-performance liquid chromatography coupled to triple-quadrupole mass spectrometry (UHPLC-QqQ)
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Grapevine stilbenes are a family of polyphenols which derive from trans-resveratrol having antifungal and antimicrobial properties, thus being considered as phytoalexins. In addition to their diverse bioactive properties in animal models, they highlight a strong potential in human health maintenance and promotion. Due to this relevance, highly-specific qualitative and quantitative methods of analysis are necessary to accurately analyze stilbenes in different matrices derived from grapevine. Here, we developed a rapid, sensitive, and specific analysis method using ultra-high-performance liquid chromatography coupled to triple-quadrupole mass spectrometry (UHPLC-QqQ) in MRM mode to detect and quantify five grapevine stilbenes, trans-resveratrol, trans-piceid, trans-piceatannol, trans-pterostilbene, and trans-?-viniferin, whose interest in relation to human health is continuously growing. The method was optimized to minimize in-source fragmentation of piceid and to avoid co-elution of cis-piceid and trans-resveratrol, as both are detected with resveratrol transitions. The applicability of the developed method of stilbene analysis was tested successfully in different complex matrices including cellular extracts of Vitis vinifera cell cultures, reaction media of biotransformation assays, and red wine.
- Hurtado-Gaitán, Elías,Sellés-Marchart, Susana,Martínez-Márquez, Ascensión,Samper-Herrero, Antonio,Bru-Martínez, Roque
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- Syntheses of polyfunctionalized resveratrol derivatives using Wittig and Heck protocols
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Improved protocols for Wittig reaction and palladium-catalyzed Heck coupling give expedient access to a series of unprecedented polyfunctionalized artificial-resveratrol derivatives. In the modified Wittig protocol, trimethylsilyl was used as a highly valuable protective group of the phenolic functions of starting aromatic materials. A clean O-alkylation of hydroxylated stilbenes with ethylene carbonate was also conducted. Thus, Wittig reaction followed by hydroxyethylation take place one-pot with only carbon dioxide as waste. Additionally, a palladium-catalyzed Heck coupling strategy was developed by using ferrocenyl phosphane ligands, and multi-functionalized hydroxylated stilbenes were obtained without the need of any protection/deprotection sequence. Up to six functional groups are introduced by these procedures, which limit the number of reactions steps, the waste toxicity, and the use of costly reagents.
- Chalal, Malik,Vervandier-Fasseur, Dominique,Meunier, Philippe,Cattey, Hélène,Hierso, Jean-Cyrille
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p. 3899 - 3907
(2012/07/14)
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- Complete NMR data of methoxylated cis- and trans-stilbenes as well as 1,2-diphenylethanes
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Resveratrol is a polyphenol isolated from many natural sources including grapes, mulberries, eucalyptus, spruce, lilies, and peanuts. The hydroxyl groups in polyphenols can be substituted with various functional groups, allowing production of multiple derivatives. NMR spectroscopy is used to identify new derivatives. Since the complete NMR data of the known derivatives can be useful for identification of the newly isolated derivatives, here, we report the synthesis of 14 methoxylated stilbenes and four 1,2-diphenylethanes and their NMR data.
- Jo, Geunhyeong,Hyun, Jiye,Hwang, Doseok,Lee, Young Han,Koh, Dongsoo,Lim, Yoongho
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p. 374 - 377
(2011/12/04)
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- Determination and imaging of metabolites from Vitis vinifera leaves by laser desorption/ionisation time-of-flight mass spectrometry
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Analysis of grapevine phytoalexins at the surface of Vitis vinifera leaves has been achieved by laser desorption/ionisation time-of-flight mass spectrometry (LDI-ToFMS) without matrix deposition. This simple and rapid sampling method was successfully applied to map small organic compounds at the surface of grapevine leaves. It was also demonstrated that the laser wavelength is a highly critical parameter. Both 266 and 337nm laser wavelengths were used but the 266nm wavelength gave increased spatial resolution and better sensitivity for the detection of the targeted metabolites (resveratrol and linked stilbene compounds). Mass spectrometry imaging of grapevine Cabernet Sauvignon leaves revealed specific locations with respect to Plasmopara viticola pathogen infection or light illumination.
- Hamm, Gregory,Carre, Vincent,Poutaraud, Anne,Maunit, Benoit,Frache, Gilles,Merdinoglu, Didier,Muller, Jean-Francois
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scheme or table
p. 335 - 342
(2011/10/12)
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- Synthesis of radiolabeled stilbene derivatives as new potential PET probes for aryl hydrocarbon receptor in cancers
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New carbon-11 and fluorine-18 labeled stilbene derivatives, cis-3,5-dimethoxy-4′-[11C]methoxystilbene (4′-[11C]8a), cis-3,4′,5-trimethoxy-3′-[11C]methoxystilbene (3′-[11C]8b), trans-3,5-dimethoxy-4′-[11C]methoxystilbene (4′-[11C]10a), trans-3,4′,5-trimethoxy-3′-[11C]methoxystilbene (3′-[11C]10b), cis-3,5-dimethoxy-4′-[18F]fluorostilbene (4′-[18F]12a), and trans-3,5-dimethoxy-4′-[18F]fluorostilbene (4′-[18F]13a), were designed and synthesized as potential PET probes for aryl hydrocarbon receptor (AhR) in cancers.
- Gao, Mingzhang,Wang, Min,Miller, Kathy D.,Sledge, George W.,Hutchins, Gary D.,Zheng, Qi-Huang
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p. 5767 - 5772
(2007/10/03)
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- Synthesis and biological evaluation of resveratrol and analogues as apoptosis-inducing agents
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Resveratrol 1 (3,4′,5-trihydroxy-trans-stilbene), a phytoalexin present in grapes and other food products, has recently been suggested as a potential cancer chemopreventive agent based on its striking inhibitory effects on cellular events associated with cancer initiation, promotion, and progression. This triphenolic stilbene has also displayed in vitro growth inhibition in a number of human cancer cell lines. In this context, a series of cis- and trans-stilbene-based resveratrols were prepared with the aim of discovering new lead compounds with clinical potential. All the synthesized compounds were tested in vitro for cell growth inhibition and the ability to induce apoptosis in HL60 promyelocytic leukemia cells. The tested trans-stilbene derivatives were less potent than their corresponding cis isomers, except for trans-resveratrol, whose cis isomer was less active. The best results were obtained with compounds 11b and 7b, the cis-3,5-dimethoxy derivatives of rhapontigenin 10a (3,5,3′-trihydroxy-4′methoxy-transstilbene) and its 3′-amino derivative 10b, respectively, which showed apoptotic activity at nanomolar concentrations. The corresponding trans isomers 12b and 8b were less active both as antiproliferative and as apoptosis-inducing agents. Of interest, 11b and 7b were active toward resistant HL60R cells and their activity was higher than that of several classic chemotherapeutic agents. The flow cytometry assay showed that at 50 nM compounds 7b or 11b were able to recruit almost all cells in the apoptotic sub-G0-G1 peek, thus suggesting that the main mechanism of cytotoxicity of these compounds could be the activation of apoptosis. These data indicate unambiguously that structural alteration of the stilbene motif of resveratrol can be extremely effective in producing potent apoptosis-inducing agents.
- Roberti, Marinella,Pizzirani, Daniela,Simoni, Daniele,Rondanin, Riccardo,Baruchello, Riccardo,Bonora, Caterina,Buscemi, Filippo,Grimaudo, Stefania,Tolomeo, Manlio
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p. 3546 - 3554
(2007/10/03)
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- Antineoplastic agents. 465. Structural modification of resveratrol: Sodium resverastatin phosphate
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As an extension of structure/activity investigations of resveratrol (1), phenstatin (2c), and the cancer antiangiogenesis drug sodium combretastatin A-4 phosphate (2b), syntheses of certain related stilbenes (14) and benzophenones (16) were undertaken. The trimethyl ether derivative of (Z)-resveratrol (4a) exhibited the strongest activity (GI50 = 0.01-0.001 μg/mL) against a minipanel of human cancer cell lines. A monodemethylated derivative (14c) was converted to prodrug 14n (sodium resverastatin phosphate) for further biological evaluation. The antitubulin and antimicrobial activities of selected compounds were also evaluated.
- Pettit, George R.,Grealish, Matthew P.,Jung, M. Katherine,Hamel, Ernest,Pettit, Robin K.,Chapuis, J.-Charles,Schmidt, Jean M.
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p. 2534 - 2542
(2007/10/03)
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