Macrowine 2021
IVES 9 IVES Conference Series 9 Cytochrome P450 CYP71BE5 from grapevine (Vitis vinifera) catalyzes the formation of the spicy aroma compound, (-)-rotundone

Cytochrome P450 CYP71BE5 from grapevine (Vitis vinifera) catalyzes the formation of the spicy aroma compound, (-)-rotundone

Abstract

(-)-Rotundone, an oxygenated sesquiterpene, is a potent odorant molecule with a characteristic spicy aroma existing in various plants including grapes1. It is considered as a significant compound notably in wines and grapes because of its low sensory threshold (16 ng L-1 in red wine, 8 ng L-1 in water) and aroma properties. (-)-Rotundone was first identified in red wine made from the grape cultivar Syrah (regionally called Shiraz) in Australia1, and then it was found in several grape varieties such as Duras, Grüner Veltliner, Schioppettino and Vespolina from Europe2, 3. Several environmental factors affecting the accumulation of (-)-Rotundone during the grape maturation, were reported such as ambient temperature4, soil properties and topography5, soil moisture from irrigation and light exposure in the bunch zone by leaf removal2. However, the biosynthetic pathway of (-)-rotundone in grapevine has been unclarified to date. In this study, we report the identification of VvSTO2 as a α-guaiene 2-oxidase which can transform α-guaiene to (-)-rotundone in the grape cultivar Syrah6. It is a cytochrome P450 (CYP) belonging to the CYP 71BE subfamily, which overlaps with the very large CYP71D family and, to the best of our knowledge, this is the first functional characterization of an enzyme from this family. VvSTO2 generated (-)-rotundone as the major reaction product with α-guaiene, and presumably (2R)-rotundol and (2S)-rotundol as the intermediate compounds to synthesize (-)-rotundone were found at trace levels in vitro enzyme assay. This result suggests that this enzyme can catalyze a one-step oxidation of α-guaiene to (-)-rotundone or a two-step oxidation via a rapid second oxidation from (2R)-rotundol and (2S)-rotundol to (-)-rotundone. VvSTO2 was expressed at a higher level in the Syrah grape exocarp (skin) in accord with the localization of (-)-rotundone accumulation in grape berries. α-Guaiene was also detected in the Syrah grape exocarp at an extremely high concentration. These findings suggest that (-)-rotundone accumulation is regulated by the VvSTO2 expression along with the availability of α-guaiene as a precursor. VvSTO2 expression during grape maturation was considerably higher in Syrah grape exocarp compared to Merlot grape exocarp, consistent with the patterns of α-guaiene and (-)-rotundone accumulation. On the basis of these findings, we propose that VvSTO2 may be a key enzyme in the biosynthesis of (-)-rotundone in grapevines by acting as a α-guaiene 2-oxidase. [References] [1] Wood, C., et al. 2008. J. Agric. Food Chem. 56, 3738-44. [2] Geffroy, O., et al. 2014. Aust. J. Grape Wine Res. 20, 401-408. [3] Mattivi, F., et al. 2011. Rapid Commun. Mass Spectrom. 25, 483-8. [4] Caputi, L., et al. 2011. J. Agric. Food Chem. 59, 5565-71. [5] Scarlett, N.J., et al. 2014. Aust. J. Grape Wine Res. 20, 214-222. [6] Takase, H., et al. 2015. J. Exp. Bot, in press.

Publication date: May 17, 2024

Issue: Macrowine 2016

Type: Poster

Authors

Hideki Takase*, Akira Shinohara, Akira Shinohara, Gen Ikoma, Hideyuki Shinmori, Hironori Kobayashi, Hironori Matsuo, Hiroshi Saito, Kanako Sasaki, Ryoji Takata

*Research Laboratories for Wine

Contact the author

Tags

IVES Conference Series | Macrowine | Macrowine 2016

Citation

Related articles…

Influence of methyl jasmonate foliar application to vineyard on grape volatile composition over three consecutive vintages

An alternative to improve grape quality is the application to the vineyard of elicitors. Although these compounds were first used to increase resistance of plants against pathogens, it has been found that they are also able to induce mechanisms involved in the synthesis of phenolic compounds and some amino acids. However, researches about the influence of elicitors on grape volatile composition are scarcely. Therefore, the aim of this work was to study the influence of methyl jasmonate (MeJ) foliar application on grape aroma composition over three consecutive vintages. MeJ was applied to Tempranillo grapevines at a concentration of 10 mM in 2013, 2014, and 2015 years. Control plants were sprayed with water.

Influence of wood chips addition during alcoholic fermentation on wine phenolic composition

This study investigates the effect of wood chips addition during the alcoholic fermentation on the phenolic
composition of the produced wines. A series of wood chips, originating from American, French, Slavonia
oak and Acacia were added at the beginning of wine alcoholic fermentation. Besides, a mixture consisting
of 50% French and 50% Americal oak chips were added during the experimentation. The wine samples
were analyzed one month after the end of malolactic fermentation, examining various chemical
parameters such as total anthocyanins, total phenolic content, tannins combined with protein (BSA) and
ellagitannin content.

Comparison of fortified, sfursat and passito winemaking techniques for the enhancement of the oenological potential of the black grape cultivar Moscato nero d’Acqui (Vitis vinifera L.)

One of the key factors of the economical development of viticulture and wine industry in specific limited areas is the exploitation of ancient, local grape varieties. Therefore, in recent years the growing interest to rediscover minor varieties, previously cultivated, has promoted many studies. With this regard, the focus of this study was the Vitis vinifera L. cultivar Moscato nero d’Acqui, nowadays found only in old vineyards in the Acqui zone (North-West Italy). In particular, the aims of this work were: i) to investigate secondary metabolites profile of the grapes, and ii) to evaluate the attitude to the production of special wines.

Glutathione content evolution during spontaneous alcoholic fermentations of Sangiovese grapes

Glutathione is a tripeptide (γ-Glu-Cys-Gly), which can occur in grapes, in must and in wine prevalently in the reduced form as well as in the oxidized form as glutathione disulfide. The importance of the reduced form of glutathione lies in its antioxidant activity. In must, it limits browning by reducing o-quinones produced by polyphenol oxidase activity on hydroxycinnamic acids; in wine, it exerts a protective effect on various aromatic compounds. Glutathione concentration in wine is lower than in grape juice and variable as it depends on several factors, ranging from the native content of grapes to winemaking technique.

Enological evaluation of the attitude of the grapevine fumin to give varietal wines

Initiatives have been ongoing in recent years to safeguard biodiversity in the oenological sector via a process of enhancement of ancient varieties, under a pressure of a market strongly oriented towards production deriving from native vines of specific geographical zones. In that sense, Aosta Valley
(Italy) has raised the need to preserve and characterize its minority vine varieties which have the potentiality to give varietal wines. Fumin represents the 7% of the production of the region with 16 hectares of vineyards and 753 hectolitres of derived wine. Due to its large phenolic potential, strong astringency and deep colour, it has long been, and is still today, assembled or blended with other varieties as occurs, for example, for the Torrette.