High-Value Phytochemicals from Grape Cane Waste: Potential. with Medicinal and Anti-Phytopathogenic Applications

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1 High-Value Phytochemicals from Grape Cane Waste: Potential Value-Added Viticultural Sources of Trans-Resveratrol andtransε-viniferin with Medicinal and Anti-Phytopathogenic Applications Sierra Rayne 1, * 1 Ecologica, Marina Way, Penticton, British Columbia, V2A 1H4, Canada. * Author for correspondence: Tel: ; rayne.sierra@gmail.com; Web: 1

2 Introduction Agricultural wastes are a largely ignored source of high-value phytochemicals and value-added industrial products. Effective extraction and commercial application of these compounds could help contribute to sustainability objectives (Das and Singh, 2004). In particular, the global wine and table grape industry, with annual sales of >US$100 billion, generates large quantities of cane pruning waste each year. Typically, these prunings are composted or burned for disposal, often with a net cost to the winery. Reports to date suggest that waste grape canes contain significant levels of a compound class termed the stilbenes. The most well-known member of the grapevine-derived stilbenes is trans-resveratrol (3,5,4 -trihydroxystilbene; 1). This compound has gained significant worldwide attention because of its ability to inhibit or delay a wide variety of diseases (Baur and Sinclair, 2006) that include cardiovascular disease (Bradamante et al., 2004) and cancer (Jang et al., 1997), and to increase stress resistance and lifespans (Baur et al., 2006; Valenzano et al., 2006), and most important to the wine industry, its link to the French paradox (Kopp, 1998). Trans-resveratrol is the first member of the stilbene series to be synthesized in plants by the enzyme stilbene synthase, via the Shikimic pathway, often in response to disease or injury stresses (Langcake and Pryce, 1976; Langcake, 1981; Aggarwal et al., 2004). Oxidative polymerization in the plant produces oligomers of trans-resveratrol, particularly trans-ε-viniferin ( 2). 2

3 HO 1 OH OH HO HO H O H OH OH 2 OH Some of these resveratrol derivatives are also known to have high bioactivities. While less studied than trans-resveratrol, trans-ε -viniferin has been shown to have hepatoprotective (Oshima et al., 1995) and antioxidant (Privat et al., 2002) properties, to induce apoptosis of leukemia B-cells (Billard et al., 2002; Quiney et al., 2004), and inhibit human cytochrome P 450 enzymes (Piver et al., 2003), noradrenaline and 5-hydroxytryptamine uptake, and monoamine oxidase activity (Yanez et al., 2006). Although some dietary sources such as wines, grapes, berries, nuts, and herbal plants contain trans-resveratrol and trans-ε -viniferin, thereby contributing to overall dietary intakes (Baur and Sinclair, 2006), there is increasing demand for additional supplementary products in pure forms, and for commercial applications that exploit the broad-spectrum bioactivity of these compounds. In addition to their well-characterized bioactive properties as nutraceuticals and pharmaceuticals, stilbenes such as trans-resveratrol and trans-ε -viniferin are also known to display significant anti-phytopathogenic properties, such as activity against downy mildew (Plasmopara viticola; Dercks and Creasy, 1989; Hoos et al., 1990; Dai et al., 1995; Pezet et al., 2004), grey mold (Botrytis cinerea; Langcake, 3

4 1981; Hoos and Blaich, 1990; Adrian et al., 1997), Phoma medicaginis (Hipskind and Paiva, 2000), Rhizopus stolonifer (Sarig et al., 1997), and a broad spectrum of microbes and fungi present during postharvest fruit and vegetable storage (Urena et al., 2003; Jimenez et al., 2005). Thus, there is potential to utilize grape cane extracts as anti-phytopathogenic sprays to aid in on-farm sustainability. Such a conceptual approach would involve the replacement of synthetic chemical analogs, and the associated environmental and economic costs. Commercial Assessment Grape canes are pruned annually, and these wastes represent a potentially important global source of trans-resveratrol and trans-ε -viniferin. After extraction, the residue could be used for other value-added purposes, such as production of activated carbon (Corcho-Corral et al., 2005). While limited studies have suggested commercial sources of trans-resveratrol and related stilbenes from other agricultural wastes such as peanut roots (Chen et al., 2002), no work has extended this application to grape prunings. There have only been two previous reports on stilbene concentrations in grape canes. Aaviksaar et al. (2003) and Pussa et al. (2006) found between 0.1 to 4.7 mg/g dry weight (dw) trans-resveratrol and from <0.1 to 1.7 mg/g dw trans-ε- viniferin contents in samples from six Vitis vinifera varieties, with levels increasing throughout the growing season. 4

5 By comparison, grape cluster stems are known to contain higher trans-resveratrol concentrations than grape skins (about 0.05 mg/g dw), but no other part contains higher levels of these high-value phytochemicals than the canes. In a survey of trans-resveratrol contents of grape cluster rachis from nine Vitis vinifera varieties, Melzoch et al. (2001) found levels ranging from to 0.48 mg/g dw, with the highest levels in a white grape cultivar (L. cv. Erilon). No trends in transresveratrol concentrations were observed by grape color. Similarly, Bavaresco et al. (1997) reported trans-resveratrol levels from 0.08 to 0.39 mg g -1 dw in grapevine clusters from eight Vitis vinifera varieties, with no variation in concentrations by grape color and the highest levels in a white cultivar (L. cv. Gewurtraminer). trans-ε -Viniferin concentrations in these varietals were about 0.5 to 6-fold that of trans-resveratrol. Pool et al. (1981) reported similar transresveratrol levels in internode xylem from 14 non-vinifera species (0.02 to 0.14 mg/g dw) and one vinifera cultivar (0.19 mg/g dw; L. cv. Sultanina). At an approximate annual grape cane production rate of 1 ton/ha (USEPA, 1995), with 8,000,000 ha of wine grapes in production worldwide ( and assuming an average trans-resveratrol content of 1 mg/g dw (the average of levels reported to date), the complete global extraction of this compound from agricultural grape pruning waste could reach 8,000 tons/y (or about 825 mg per capita worldwide). With a commercial value of about US$2,000 to US$3,000 per kg (Baur and Sinclair, 2006), trans-resveratrol yields from cane waste could supply a value-added agricultural coproduct worth US$2,000 to US$3,000 per hectare of production, or a global potential ranging up to US$24 billion. 5

6 No information is available on the commercial value of trans-ε -viniferin, but assuming an equivalent market value as trans-resveratrol and average grape cane contents of 0.25 mg/g dw, extraction of this compound could yield an additional US$500 to US$750 per hectare of production (or up to US$6 billion globally). Furthermore, postharvest stilbene contents of grape cane may possibly be increased through exposure to UV light, ozone, or other abiotic stresses. These types of treatments have been shown to increase stilbene levels up to several hundred-fold in grape skins (Artes-Hernandez et al., 2003; Cantos et al., 2000, 2001, 2002, 2003; Gonzalez-Barrio et al., 2006; Sarig et al., 1996) and leaves (Adrian et al., 1996), and peanuts and peanut kernels (Ingham, 1976; Rudolf and Resurreccion, 2005), offering the potential to further maximum economic returns. Conclusions Grape canes as agricultural waste from commercial viticultural activities represent a potentially important source of the well-known medicinal and antiphytopathogenic stilbene compounds trans-resveratrol and trans-ε -viniferin. Reports in the literature suggest that concentrations of these compounds range up to 5 mg/g dw and 2 mg/g dw, respectively, and can be quantitatively extracted from the cane residue using low-cost, environmental benign, and non-toxic aqueous alcoholic solvent systems such as ethanol:water mixtures. With current commercial values of these compounds between US$2,000 to US$3,000 per kg, established stilbene yields from cane waste could represent an agricultural coproduct valued at US$2,000 to US$3,000 per hectare of production. At the 6

7 present worldwide wine grape production of 8,000,000 ha, the extraction of transresveratrol and trans-ε -viniferin from grape cane waste would have an estimated global economic value of >$30 billion. 7

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Effect of storage on stilbenes contents in cv. Pinot Noir grape canes collected at different times before pruning

Effect of storage on stilbenes contents in cv. Pinot Noir grape canes collected at different times before pruning Gicele Sbardelotto De Bona Simone Vincenzi September 25th 29th, 2016 Padova, Italy Global