Physico-chemical studies of resveratrol, methyl-jasmonate and cyclodextrin interactions: an approach to resveratrol bioproduction optimization

Oliva, E.; Mathiron, David; Bertaut, E.-F.; Landy, David; Cailleu, Dominique; Pilard, Serge; Clément, Christophe; Courot, Eric; Bonnet, Véronique; Djedaïni‐Pilard, Florence

doi:10.1039/c7ra11619e

Cited by 16 publications

(24 citation statements)

References 44 publications

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“…First, 1 H DOSY NMR experiments also confirmed the interaction of MOR with α-CD due to variations in the diffusion coefficient D value as displayed in Figure 5 A. The diffusion coefficient can be linked to the translational motion of molecules in solution and its value depends on the size of the object [ 24 ]. The bigger the molecule is, the smaller the D value will be.…”

Section: Resultsmentioning

confidence: 92%

“…Excess amount of MOR were added (20 mg) to a 0.6 mL D 2 O solution containing different α-CD concentrations (from 10 to 50 mM). The suspensions were maintained at 300 K for 24 h, filtered through 0.2 µm cellulose filters from Grace (Columbia, MD, USA) and analysed by a 1 H-NMR quantitative experiment called ERETIC [ 24 ]. First, a 1 H-NMR experiment using zg pulse program (D1 5 s, AQ 4.54 s, TD 64K, NS 8) with a Bruker reference standard triphenylphosphate (TPP) (48.5 mM in aceton-d6)was performed.…”

Section: Methodsmentioning

confidence: 99%

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A Combined Approach of NMR and Mass Spectrometry Techniques Applied to the α-Cyclodextrin/Moringin Complex for a Novel Bioactive Formulation †

et al. 2018

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Moringin, obtained via enzymatic conversion of the glucosinolate precursor glucomoringin, is an uncommon member of the isothiocyanate class, and has been proven to possess a broad range of biological activities such as antitumor activity, protection against neurodegenerative disorders and bactericidal effects. Since moringin is weakly soluble in water and unstable in aqueous medium, cyclodextrins (CDs) were considered for the development of a new moringin formulation, with a view to improving its solubility and stability in aqueous solution for use as an anti-inflammatory. A combined structural study using proton nuclear magnetic resonance (1H-NMR), diffusion-ordered spectroscopy (DOSY) and ion mobility mass spectrometry (IM-MS) is reported, highlighting the formation of a 1:1 α-CD/moringin inclusion complex. The association constant K was determined (1300 M−1 at 300 K). Completion of the structural characterization was performed by T-ROESY and MS/MS experiments, which evidenced the mode of penetration of moringin into α-CD. Finally, the “chaperone-like” properties of α-CD with respect to the stability of moringin have been highlighted.

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Section: Resultsmentioning

confidence: 92%

Section: Methodsmentioning

confidence: 99%

A Combined Approach of NMR and Mass Spectrometry Techniques Applied to the α-Cyclodextrin/Moringin Complex for a Novel Bioactive Formulation †

et al. 2018

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“…The ratio MeJA concentration/biomass is a key element to understand resveratrol production, and the optimal ratio observed in this work was 0.125 mmol/g DW. Furthermore, it has been shown that the solubility of MeJA in the water liquid medium could be enhanced by its complexation with cyclodextrins, and then provoked the highest elicitation response [41].…”

Section: Optimization Of Meja Elicitation In Flask Experimentsmentioning

confidence: 99%

Optimize, Modulate, and Scale-up Resveratrol and Resveratrol Dimers Bioproduction in Vitis labrusca L. Cell Suspension from Flasks to 20 L Bioreactor

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Lemaire

Auger

et al. 2019

Plants

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Resveratrol and its oligomers are biologically active compounds. This work brings new insights for the bioproduction of trans-resveratrol with three dimers, pallidol, trans-ε-viniferin, and trans-δ-viniferin, in cell suspension of Vitis labrusca. Conditions of elicitation by methyl jasmonate were optimized for the production of stilbenes using statistical design of experiment. Bio-production of stilbenes was scaled-up to 5 L and in these conditions, trans-resveratrol concentrations reached 237 mg/L, and for pallidol 114 mg/L. The comparison of different elicitation modes (different elicitors, combination with cyclodextrins or adsorbent resin) allowed to reach particularly high concentrations of target molecules: Resveratrol 6.14 g/L, pallidol 0.90 g/L, δ-viniferin 0.54 g/L, and ε-viniferin 0.50 g/L. Scale-up to 20 L-stirring-bioreactor gave similar growth rates to those observed in shake flask culture, with a high production of resveratrol (4.23 g/L) and δ-viniferin (0.76 g/L). This work provides new strategies for the production of stilbenes in plant cell suspension for biological and commercial evaluation.

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“…This could suggest a potential phenomenon of aggregation of β-CD(C9)2OOMe 1 in aqueous medium. In order to study the dipolar interactions between protons of the CD cavity and those of the fatty chains, a T-ROESY NMR experiment was performed on β-CD(C9)2OOMe 1 in D2O ( Figure 5) [42]. Strong cross-correlation peaks between alkyl protons and protons of CD moiety have been observed revealing interactions of the grafted chains with the CD cavity.…”

Section: Self-organization Propertiesmentioning

confidence: 99%

New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling

et al. 2020

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Bearing grafts based on fatty esters derivatives, lipidyl-cyclodextrins (L-CDs) are compounds able to form water-soluble nano-objects. In this context, bicatenary biobased lipidic-cyclodextrins of low DS were easily synthesized from a fatty ester epoxide by means of alternative methods (ball-milling conditions, use of enzymes). The ring opening reaction of methyl oleate epoxide needs ball-milling and is highly specific of cyclodextrins in solventless conditions. L-CDs are thus composed of complex mixtures that were deciphered by an extensive structural analysis using mainly mass spectrometry and NMR spectroscopy. In addition, as part of their potential use as vectors of active drugs, these products were submitted to an integrity study on in vitro model of the blood-brain-barrier (BBB) and the intestinal epithelium. No toxicity has been observed, suggesting that applications for the vectorization of active ingredients can be expected.

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Physico-chemical studies of resveratrol, methyl-jasmonate and cyclodextrin interactions: an approach to resveratrol bioproduction optimization

Abstract: The role of cyclodextrins in the bioproduction of resveratrol in the presence of methyl-jasmonate is rationalized, leading to solutions for the improvement of bioproduction.

Cited by 16 publications

References 44 publications

A Combined Approach of NMR and Mass Spectrometry Techniques Applied to the α-Cyclodextrin/Moringin Complex for a Novel Bioactive Formulation †

A Combined Approach of NMR and Mass Spectrometry Techniques Applied to the α-Cyclodextrin/Moringin Complex for a Novel Bioactive Formulation †

Optimize, Modulate, and Scale-up Resveratrol and Resveratrol Dimers Bioproduction in Vitis labrusca L. Cell Suspension from Flasks to 20 L Bioreactor

New Lipidyl-Cyclodextrins Obtained by Ring Opening of Methyl Oleate Epoxide Using Ball Milling

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