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Subcritical Water Extraction of Stilbenes from Grapevine By Industrial Crops & Products 126 (2018) 272–279 Contents lists available at ScienceDirect Industrial Crops & Products journal homepage: www.elsevier.com/locate/indcrop Subcritical water extraction of stilbenes from grapevine by-products: A new T green chemistry approach Julien Gabastona, Cécile Leborgnea, Josep Vallsa, Elodie Renoufb, Tristan Richarda, ⁎ Pierre Waffo-Teguoa, Jean-Michel Mérillona,b, a Univ. Bordeaux, Faculté des Sciences Pharmaceutiques, Unité de Recherche Œnologie, EA 4577, USC 1366 INRA, Equipe Molécules d’Intérêt Biologique (Gesvab) - ISVV, 33882, Villenave d’Ornon cedex, France b Polyphénols Biotech (Technology Transfer Unit), ISVV, 33882, Villenave d’Ornon cedex, France ARTICLE INFO ABSTRACT Keywords: Currently, one of the biggest challenges in viticulture is to valorize the huge amount of biomass, especially Polyphenols grapevine waste. Subcritical water is a sustainable and eco-friendly method of extraction based on the use of Stilbenes water as an extracting agent, corresponding to the strategy called "green chemistry". Application of a high Vine by-products temperature and a high pressure maintains the water in its liquid form allowing polar and less polar compounds Subcritical water to be extracted. Stilbenes are low-polarity compounds that normally require organic solvents for their extraction. Eco-extraction This study investigated the possibility of using a subcritical water process to extract complex stilbenes from three vine co-products: cane, wood, and root. Various temperatures (100, 130, 160 and 190 °C) and contact times (5, 15 and 30 min) were tested by accelerated solvent extraction (ASE). The highest stilbene yield was obtained at 160 °C and 5 min for cane (3.62 g/kg dry mass), wood (9.32 g/kg dry mass) and root (12.1 g/kg dry mass). ASE allowed the extraction of monomers, dimers, trimers and tetramers of stilbenes in similar amounts as with conventional organic solvents. In addition, the subcritical extraction conditions led to the formation of an un- common tetrameric stilbene, named vitisin F. The possibility of using “green chemistry” for extracting oligo- meric stilbenes is a step forward in the search for alternatives to organic solvents. 1. Introduction Parliament issued a directive stipulating that waste prevention is the priority in waste management, and that waste recycling should be given For several decades, viticulture has been a predominant economic priority over energy re-use (European Parliament, 2008a). Thus, one of and societal activity, particularly in Europe. France, Italy and Spain are the biggest challenges in agriculture is to create alternatives and va- among the largest producers of wine worldwide generating half of the lorize the huge amount of biomass, especially in viticulture. world's wine production, about 134 million hectoliters out of the 279 Recently, studies have shown innovative applications for vine co- million hectoliters of wine (Eurostat, 2017). However, viticultural products. Extracts of grapevine canes showed in vitro antifungal activ- practices are one of the most productive agricultural activities of ve- ities against the three major vineyard diseases: Plasmopara viticola, getal waste (Valls et al., 2017). Indeed, grapevine canes are pruned Botrytis cinerea and Erysiphe necator (Schnee et al., 2013). Focusing on P. each year generating a large source of biomass. In France, about 1.4 viticola infection, greenhouse and vineyard studies conducted with a million tons of grapevine canes per year are generated (FranceAgrimer, cane extract against downy mildew produced similar results to tradi- 2016) while the Castilla-La Mancha region in Spain produces about tional treatments (Richard et al., 2016). Recent studies of the other 1.15 million tons of cane (Sánchez-Gómez et al., 2014). The replace- vegetative parts of the grapevine have demonstrated that wood and ment of vineyards also generates a large amount of grapevine wood and root extracts are more active against downy mildew than cane extracts root waste. The French vineyards generate about 0.4 million tons of this (Gabaston et al., 2017). Furthermore, extracts of cane and roots exerted biomass per year (ADEME, 2009; ATLAS, 2017). Currently, the diffi- an insecticidal activity against Spodoptera littoralis and Leptinotarsa de- culty of storing byproducts as well as their reprocessing costs has made cemlineata (Gabaston et al., 2018; Pavela et al., 2017). Thus, the use of waste management burdensome. To meet this challenge, the European viticultural co-products in the phytosanitary field has a promising ⁎ Corresponding author at: Univ. Bordeaux, Faculté des Sciences Pharmaceutiques, Unité de Recherche Œnologie, EA 4577, USC 1366 INRA, Equipe Molécules d’Intérêt Biologique (Gesvab) - ISVV, 33882, Villenave d’Ornon cedex, France. E-mail address: [email protected] (J.-M. Mérillon). https://doi.org/10.1016/j.indcrop.2018.10.020 Received 20 June 2018; Received in revised form 5 October 2018; Accepted 6 October 2018 0926-6690/ © 2018 Elsevier B.V. All rights reserved. J. Gabaston et al. Industrial Crops & Products 126 (2018) 272–279 future for valorization. Additionally, cane extracts have recently been 2. Materials and methods tested as alternatives to SO2 for winemaking and could be used in the oenological field (Raposo et al., 2018). Canes were also tested as a 2.1. Plant material potential oenological additive as toasted chips in order to produce wines with complexity in terms of flavor and taste (Cebrián-Tarancón Grapevine canes, woods and roots were collected from the “Château et al., 2018). Rochemorin” vineyard in the region of Bordeaux (France) in 2017. We These activities are due notably to the presence of stilbenes in the used a Merlot cultivar grafted on a Riparia Gloire de Montpellier vegetative parts of the grapevine. Stilbenes are polyphenolic com- rootstock. Each part was crushed once on an electric shredder (Bosch, pounds with a C6-C2-C6 structure that are derived from the secondary Stuttgart, Allemagne) and finely ground with a cutting mill (Fritsch, metabolism of plants (Pawlus et al., 2012; Rivière et al., 2012). They Idar-Oberstein, Allemagne). Samples were stored in a dry place until are particularly known for their antimicrobial properties and act as extraction. phytoalexins (i.e. molecules produced by the plant to defend itself) in certain families of plants (Jeandet et al., 2002). Recent work showed 2.2. Extraction procedure the activity of oligomeric stilbenes present in grapevine against several pathogens (Schnee et al., 2013). Vitisins A (r2-viniferin) and B (r-vi- Subcritical water extraction was carried out using an accelerated niferin), hopeaphenol and isohopeaphenol are tetramers that have de- solvent extraction (ASE) apparatus (Dionex Corporation, Sunnyvale, monstrated antifungal properties against downy mildew (Gabaston CA). Extraction was performed at four different temperatures (100, et al., 2017). Another study also reported the efficacy of complex stil- 130, 160 and 190 °C) and three different times of extraction (5, 15 and benes in reducing the growth of grapevine wood decay fungi (Lambert 30 min). All extractions were done with five grams of powder ina et al., 2012). The presence of these complex stilbenes in active extracts 34 mL cartridge containing a fiberglass filter with the following para- is therefore important and their extraction from viticultural co-products meters: pressure, 100 bars; cycle, 1; rinse volume, 30%; purge, 100 s; is a major challenge. extraction solvent, water. Controls were performed on the ASE appa- At present, oligomeric stilbenes have been extracted from plant ratus with five grams of samples and an ethanol-water mixture (85/15; materials by using traditional methods based on organic solvents owing v/v) at 60 °C and one cycle of 5 min. All extractions were carried out in to their polarities. Solvents such as ethanol, methanol, acetone and triplicate on grapevine cane, wood and root. ethyl acetate have been widely used in conventional solid-liquid ex- traction processes (Merken and Beecher, 2000). However, this excessive 2.3. Chemicals and standards consumption of organic solvents has a negative impact on the en- vironment with the generation of toxic waste. Solvents can also impact Extractions with subcritical water were performed with purified human health; for example, methanol was recently classified as a CMR water from an Elga water purification system (High Wycombe, U.K.). (carcinogenic, mutagenic, or toxic for reproduction) product (European Control extractions were carried out with absolute ethanol purchased Parliament, 2008b). In addition, these traditional extraction methods from VWR (Fontenay-sous-bois, France). Analyses were performed with are generally time-consuming and labor-intensive (Choi et al., 2003). LC–MS-grade acetonitrile (VWR, Fontenay-sous-bois, France), formic Therefore, there is renewed interest in the use of sustainable and acid (Fisher Scientific, Loughborough, U.K.) and HPLC-grade methanol environmentally friendly solvents as alternatives to organic solvents, (Sigma-Aldrich, St Louis, MO). Standard isolations were carried out corresponding to a strategy called "green chemistry". These principles with HPLC-grade acetonitrile and trifluoroacetic acid (TFA) obtained tend to reduce the use of organic solvents in favor of clean solvents such from Sigma-Aldrich (St Louis, MO). as water. One of the trends in ecofriendly polyphenol extraction tech- Stilbenes were purified as standards using a Varian
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