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Smoke Taint in Wine: How smoke-derived volatiles accumulate in grapevines.

Wildfires have become an increasing problem in the United States in recent years. During the first half of 2017, 58,583 wildfires burned roughly 8.5 million acres, according to the National Interagency Fire Center. (1) Compared to the 10-year average of approximately 6 million acres burned per year by wildfires, the 2017 land loss exceeds this by far. The effects are hazardous, with millions of homes threatened and financial losses that add up to billions of dollars over the past 10 years. (2)

Smoke taint in wine

Unfortunately, more and more fires also strike in famous grapegrowing areas, such as the October 2017 firestorm in Sonoma, Napa and Mendocino counties in California. Apart from the direct danger of losing a vineyard to the fire, there is also an indirect risk of smoke exposure. When smoke from a wildfire is passing over vineyards, vinification of the affected berries can lead to unpalatable wines. These wines convey strong "ashy," "burnt" and "smoky" aromas, with "an excessively drying" backpalate and retro-nasal "ash" perception. (3,4)

Recent studies report on the occurrence of this "smoke taint" in wines from California and Canada, but also from Australia, South Africa and Greece. (5-8) The consequence is a significantly reduced market value, as consumers have been shown to reject smoke-tainted wines. (9)

Smoke-derived volatiles in grapevines

Smoke from wood fire contains small volatile phenols such as guaiacol, 4-methylguaiacol, syringol, m-cresol, o-cresol and p-cresol (see "Smoke-Derived Volatile Phenols and Resveratrol" below) that contribute to the characteristic "burnt" odor. (10,11) Of these compounds, guaiacol, m-cresol and 4-methylguaiacol have the lowest aroma thresholds of 23 [micro]g/L, 20 [micro]g/L and 30 [micro]g/L (BET, or best estimate threshold), respectively, emphasizing why they are considered the primary chemicals associated with smoke taint. (11) The U.S. wine industry has accepted the quantification of guaiacol and 4-methylguaiacol as indicators for smoke taint potential in grape juice and/or wine. It is suggested that they enter grapes mainly through the skins and the waxy cuticle rather than through the leaves. (12)

However, even when the level of indicators was low and the grape juice did not show a specific ashy note, the corresponding wines exhibited smoke taint. (13,14) This is pointing toward the existence of a native grapevine-regulation system that processes the volatile phenols and masks their unpleasant smoky aroma.

Binding of volatile phenols to grape sugars

Juice from grapes affected by smoke was studied in laboratory analyses to discover what occurred with the volatile phenols.15 The experiments demonstrated that the plant had bound the smoky compounds to grape sugars (see "Uptake and Release of Smoke Taint in Grapevines" on page 61). The compounds lost their volatile properties, being now odorless and hidden within the juice. Why is the grapevine processing the smoky volatiles in such a way?

Recently, one cause was discovered by researchers of the Technical University of Munich, Germany. (3) Scientists found enzymes native to the grapevines that convey the binding of grape sugars to the smoky volatiles. These enzymes, called glycosyltransferases (GTs), transfer sugar molecules. In a laboratory environment, the activity of three GTs toward the most important smoke indicator compounds was tested. It was confirmed that the enzyme UGT72B27 processed all indicator compounds with high efficiency.

Natural glycosyltransferase activity

This leads to the question: Why is an enzyme native to the grapevine active on foreign smoky molecules? Here, the researchers found an explanation. They suggested that, under normal circumstances, the enzyme is binding glucose moieties to trans-resveratrol, a naturally occurring metabolite in grapevines. (16) It has been detected in single and sugar-bound form in whole berries and in resulting wines and is usually released by the plant upon pathogen-infection or injury to counteract bacteria and fungi. (17)

Regarding the chemical structure of transresveratrol, certain similarities to the smoky volatiles can be observed immediately. Similar to guaiacol, syringol and o-cresol, trans-resveratrol possesses a basic phenolic structure and functional hydroxyl groups that enable the linkage of a sugar moiety. Therefore, the scientists at the Technical University of Munich argue that the grapevine enzyme cannot distinguish between its natural substrate trans-resveratrol and the foreign smoky molecules. (3) It is processing both.

Problems for the winegrower

One might think that this intrinsic grapevine activity is an advantage, as the smoky volatiles are rendered non-smoky and masked by the binding to a sugar molecule. However, during winemaking, the bound smoke compounds are cleaved (hydrolyzed) from sugar molecules, thus allowing the smoky volatile phenol aromas and flavors to be released into wine (see "Uptake and Release of Smoke Taint in Grapevine"). Hydrolysis of the sugar bond can occur throughout the winemaking process including during fermentation, aging and storage. In fact, there can be a dramatic progressive release of the smoky compounds. It has been shown that the level of guaiacol can increase from 4.3 [micro]g/L in control (unsmoked) wine up to 388.3 [micro]g/L in wines exposed to smoke applications from juice stage to completion of malolactic fermentation. (18)

The hydrolysis reaction has been proposed to be executed primarily by enzymes such as [beta]-glucosidase, which are native to wine yeasts and wine bacteria. However, acid hydrolysis cannot be ruled out as a possible mechanism for release of the smoky phenols. Furthermore, it has been shown that upon consumption of smoke-affected wine enzymes in human saliva can also cleave off remaining sugars, causing an unpleasant retro-nasal ash perception. (8) This explains why wines can have ashy notes, even when the unfermented grape juice did initially not show hints of an unpleasant aroma.

Future prospects and possible solutions

Thanks to wine research, we now know how such a taste can develop. In the future, a grapevine variety could be bred to produce less GT enzyme. Alternately, a second sugar molecule could be added to prevent release of the smoky aroma, or yeasts not able to cleave the sugarbound volatiles could be searched.

From a practical point of view, it would be desirable to develop a process specifically to remove the smoky volatiles or their sugar-bound forms from juice and wine without removing beneficial flavors and aromas. Unfortunately, many valuable flavor/aroma compounds are chemically highly similar to the smoky phenols, which is why the development of such a method would be very difficult.

By means of genetic engineering, the grapevine gene responsible for production of the GT could be removed. However, consumers in certain areas such as Europe tend to reject genetically modified foods and beverages. Meanwhile, winegrowers and winemakers can take steps to minimize the sensory impacts of smoke exposure. Detailed advisory sheets are available online from the Department of Agriculture and Food in Western Australia and the Australian Wine Research Institute. (19)

KEY POINTS

Smoke from wood fire contains volatile phenols with an ashy aroma that enters the grapes mainly through skins and the waxy cuticle.

Native grapevine enzymes called glycosyltransferases bind sugar molecules to the volatile phenols, rendering them odorless and hidden within the juice.

During fermentation of the grape juice and upon consumption of the wine, the sugar molecules are cleaved off, leading to a progressive release of the smoke compounds and creating an unpalatable taste.

Katja Hartl is lecturer and researcher in the Department of Biotechnology of Natural Products at Technical University of Munich in Freising, Germany. She specializes in enzymatic activities and the availability of single and sugar-bound secondary metabolites in crop plants including the grapevine.

Wilfried Schwab is professor and head of the Biotechnology of Natural Products Department at Technical University of Munich in Freising, Germany. His research interests are enzymes and secondary metabolites in plants, metabolic engineering and whole-cell biocatalysis of bioactive plant compounds.

Please Note: Illustration(s) are not available due to copyright restrictions.

Caption: SMOKE-DERIVED VOLATILE PHENOLS AND RESVERATROL Chemical structures of characteristic smoky aroma volatiles found in smoke from wood fire (guaiacol, 4-methylguaiacol, syringol, o-cresol, m-cresol, and p-cresol), and the naturally occurring grapevine metabolite frans-resveratrol.

Caption: UPTAKE AND RELEASE OF SMOKE TAINT IN GRAPEVINES The above sequence is responsible for the uptake and release of smoke taint in grapevines. Sugars are added by a process called glycosylation and are cleaved off again during fermentation.
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Title Annotation:GRAPEGROWING: PRACTICAL WINERY & VINEYARD
Comment:Smoke Taint in Wine: How smoke-derived volatiles accumulate in grapevines.(GRAPEGROWING: PRACTICAL WINERY & VINEYARD)
Author:Hartl, Katja; Schwab, Wilfried
Publication:Wines & Vines
Date:Feb 1, 2018
Words:1363
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