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…

Oxygen consumption by diferent oenological tanins in a model wine solution

INTRODUCTION: Oenological tannins are widely used in winemaking to improve some characteristics of wines [1] being the antioxidant properties probably one of the main reasons [2]. However, commercial tannins have different botanical sources and chemical composition [3] which probably determines different antioxidant potential. There are some few references about the antioxidant properties of commercial tannins [4] but none of them have really measured the direct oxygen consumption by them. The aim of this work was to measure the kinetics of oxygen consumption by different commercial tannins in order to determine their real capacities to protect wine against oxygen. MATERIAL AND METHODS: 4 different commercial tannins were used: T1: condensed tannin from grape seeds, T2: gallotannin from chinese gallnuts, T3: ellagitannin from oak and T4: tannin from quebracho containing condensed tannins and ellagitannins.

Metabolomics of grape polyphenols as a consequence of post-harvest drying: on-plant dehydration vs warehouse withering

A method of suspect screening analysis to study grape metabolomics, was developed [1]. By performing ultra-high performance liquid chromatography (UHPLC) – high-resolution mass spectrometry (HRMS) analysis of the grape extract, averaging 320-450 putative grape compounds are identified which include mainly polyphenols. Identification of metabolites is performed by a new HRMS-database of putative grape and wine compounds expressly constructed (GrapeMetabolomics) which currently includes around 1,100 entries.

Measurements of the oxygen dissolved in white wines elaborated in barrels without to open the bung of the barrels

Bases on oxoluminescence, we have developed an innovative device for measuring dissolved oxygen in wines in barrels without opening the bung. This system is directly inserted into the wood during the barrel elaboration and can be positioned at different locations of the barrel (the head, the hull …). During two successive vintages we have used this device notably to follow the oxygen dissolved of whites wines elaborated in barrels. This allowed us initially to monitor the oxygen levels of the harvest to bottling the whole elaboration process in barrels of white wines without using techniques of measurement suitable to modify the real values in wines (opening the bung to plunge an oximeter).

Impact of glutathione and elemental sulphur juice addition on the volatile thiol production in South African Sauvignon blanc wine

Three compounds, 3-mercaptohexanol (3MH), 3-mercaptohexyl-acetate (3MHA) and 4-mercapto-4-methylpentan-2-one (4MMP), also known as varietal thiols, have been identified to contribute positively to wine aroma and are responsible for the distinct gooseberry, grapefruit, guava and box tree character found in Sauvignon blanc wines. Certain volatile thiol compounds though, can cause off-aromas of onion, garlic, rubber and rotten egg, this group of molecules is known as reductive sulphur compounds (RSC). This study looks into how the addition of sulphur-compounds to Sauvignon blanc juice contributes to the varietal thiol (3MH and 3MHA) concentration and reductive sulphur compound concentration in South African Sauvignon blanc wine.

The moment of preharvest elicitor application influence its final effect on winegrapes quality

Phenolic compounds are secondary metabolites of grapes. Plants produce a wide variety of this type of metabolites through diverse biosynthesis pathways and their production is sometimes a response to external stimuli, either environmental or biotic stresses. Some of them may act as chemical defenses against pathogens or herbivores and their synthesis is increased when the attack exists. However, it is remarkable that the synthesis of these interesting compounds can be activated even when the stimulus is not present, with the use of elicitors. These are substances that when applied exogenously trigger the biosynthetic pathways conducting to the synthesis of these defense compounds.