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…

The effect of Nitrogen and Sulphur foliar applications in hot climates

ine nitrogen deficiency can negatively influence the aroma profile and ageing potential of white wines. Canopy management can alter vine microclimate, affect the nitrogen availability and influence the response of leaf senescence. Increasing the nitrogen availability to vines can increase the Yeast Assimilable Nitrogen (YAN) levels in harvested fruit and wine. Studies show that foliar nitrogen and sulphur applications at véraison, on low YAN Sauvignon blanc grapes have an effect on the level of amino acids (Jreij et al. 2009) and on S-containing compounds such as glutathione and thiols (Lacroux et al. 2008), which in turn can influence the formation of major volatiles and the aroma profile of the wine.

Impact of elemental sulfur (S0) residues in Sauvignon blanc juice on the formation of the varietal thiols 3-mercapto hexanol and 3-mercaptohexyl acetate

Elemental sulfur is a fungicide used by grape growers to control the development of powdery mildew, caused by the fungus Erysiphe necator. This compound is effective, cheap and has a low toxicity with no withholding period recommended. However, high levels of S0 residues in the harvested grapes can lead to the formation of reductive sulfur compounds that can impart taints and faults to the wine. Hydrogen sulphide (H2S) is a very volatile and unpleasant sulfur compound which formation is connected to high residues of S0 in juice (10 – 100 mg/L).

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.

Innovations in the use of bentonite in enology: interactions with grape and wine proteins, colloids, polyphenols and aroma compounds.

The use of bentonite in oenology rounds around the limpidity and the stability that determine consumer acceptability. As a matter of fact, the haze formation in wine reduces its commercial value and makes it unacceptable for sale. Stabilization treatments are, therefore, essential to ensure a long-time limpidity and to forecast the formation of deposits in the bottle. Bentonite that is normally used in oenology for clarifying-fining purpose, shows a natural clay-based mineral structure allowing it to swell and to jelly in water and hence in must and wine.

Fingerprinting the origin of rosé wines with a new high throughput polyphenomics method

Wine is a widely consumed alcoholic beverage with a high commercial value. More specifically, the worldwide consumption of rosé wine has increased by 20% since 2002[1]. But because of its high commercial value, it can become a subject of fraud, and authenticity control is necessarily required. More than one hundred polyphenols have been recently quantified in various rosé wines [2]. They are key components defining color, taste and quality of wines. Their amount and composition depend on many different factors such as grape variety, winemaking and age of the wine. In this study, the influence of geographic origin of some rosé French wines was investigated. An original and very fast UPLC-QTOF-MS method was developed and used to predict the geographic origin authenticity of rosé wines.