Cytochrome P450 CYP71BE5 in grapevine (<i>Vitis vinifera</i>) catalyzes the formation of the spicy aroma compound (−)-rotundone

Takase, Hideki; Sasaki, Kenji; Shinmori, Hideyuki; Shinohara, Akira; Mochizuki, Chihiro; Kobayashi, Hironori; Ikoma, Gen; Saitô, Hiroshi; Matsuo, Hironori; Suzuki, Shunji; Takata, Ryoji

doi:10.1093/jxb/erv496

Cited by 56 publications

(48 citation statements)

References 66 publications

(89 reference statements)

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“…In 2014, the technique did not impact significantly the rotundone concentration and more variability was observed within the data set. The cutting of the fruit bearing cane seems to have slowed down the accumulation of rotundone which can be formed by direct synthesis from ␣-Guaiene (Takase et al, 2016) or accelerated its degradation in Cane in 2013 without this being observed in 2014. Mechanisms involved appear to be complex and rotundone concentration in experimental wines is the resultant of both accumulation and degradationin the berries.…”

Section: Parametermentioning

confidence: 99%

On-vine grape drying combined with irrigation allows to produce red wines with enhanced phenolic and rotundone concentrations

Geffroy

Siebert

Herderich

et al. 2016

Scientia Horticulturae

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Section: Parametermentioning

confidence: 99%

On-vine grape drying combined with irrigation allows to produce red wines with enhanced phenolic and rotundone concentrations

Geffroy

Siebert

Herderich

et al. 2016

Scientia Horticulturae

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“…Meanwhile, an analysis of wines produced from this vineyard over 15 vintages showed that the highest concentration of rotundone was found in wines from cool and wet seasons (Zhang et al ). Whilst other work has started to unravel the genetic elements of the biosynthesis of rotundone (Drew et al , Takase et al ), the question of how this understanding might be applied to the advantage of grapegrowers and winemakers remains uncertain.…”

Section: Introductionmentioning

confidence: 99%

Patterns of within-vineyard spatial variation in the ‘pepper’ compound rotundone are temporally stable from year to year

Bramley

Siebert

Herderich

et al. 2016

Australian Journal of Grape and Wine Research

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Background and Aims: Within-vineyard variation in the concentration of grape berry rotundone has been shown to be spatially structured and related to variation in the land (soil, topography) underlying the vineyard, although its temporal stability has not been evaluated. Our aim here was therefore to ascertain whether patterns of rotundone variation were stable from year to year. This is an important aspect in understanding and exploiting terroir on a vineyard-scale as it informs how targeted management might take advantage of the variation to the benefit of both grapegrowers and winemakers. It also facilitates targeted research into the biophysical factors that may be critical to the formation of rotundone in grapes. Methods and Results: Immediately prior to the commercial harvest of a 6.1 ha vineyard block in the Grampians region of Victoria, 177 geo-referenced samples of grapes were collected in each of three seasons (2012, 2013 and 2015) and analysed for their rotundone concentration. The mean berry rotundone concentration varied 40-fold between seasons, yet spatial analysis of maps of rotundone variation produced for each year indicated that the patterns of spatial variation were stable across seasons. Conclusions: Irrespective of the seasonal factors which affect the mean concentration of berry rotundone, variation in the land (soil, topography) underlying the vineyard is a consistent driver of within-vineyard variation in this important grape-derived flavour and aroma compound. Significance of the Study: This work suggests that targeted vineyard management strategies, including selective harvesting, may be used to manipulate wine stylein this case, the pepperiness of cool climate Shiraz wines. It also suggests that further study of the relationships between the environment and berry composition is warranted in pursuit of a more robust understanding of terroir.

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“…Recently, the mechanism for forming a 12,6b-lactone at the germacrene stage in thapsigargin biosynthesis has been described (Andersen et al, 2017), in which a 6b-hydroxyl group is already present prior to the successive oxidation on the C12, and then the C12 triple oxidation leads to the spontaneous formation of a 12,6blactone ring. Therefore, similarly, to form the 12,8b-lactone ring, it would be possible that the 8b-hydroxylation on germacrene A might occur before the C12 triple oxidation by the GAO, as the enzyme GAO catalyzing the C12 triple oxidation has a broad substrate specificity (Gavira et al, 2013;Eljounaidi et al, 2014;Takase et al, 2016), and may accommodate the 8b-hydroxyl germacrene A as the substrate to facilitate the 12,8b-lactone ring formation. However the co-expression of CYP71BL6 in yeast with the germacrene A synthase LsGAS suggested that CYP71BL6 has no activity with germacrene A (Figure S5).…”

Section: Discussionmentioning

confidence: 99%

Discovery of a non‐stereoselective cytochrome P450 catalyzing either 8α‐ or 8β‐hydroxylation of germacrene A acid from the Chinese medicinal plant, Inula hupehensis

et al. 2017

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These authors contributed equally to this work. SUMMARYSesquiterpene lactones (STLs) are C15 terpenoid natural products with a-methylene c-lactone moiety. A large proportion of STLs in Asteraceae species is derived from the central precursor germacrene A acid (GAA). Formation of the lactone rings depends on the regio-(C6 or C8) and stereoselective (a-or b-)hydroxylations of GAA, producing STLs with four distinct stereo-configurations (12,6a-, 12,6b-, 12,8a-, and 12,8b-olide derivatives of GAA) in nature. Curiously, two configurations of STLs (C12,8a and C12,8b) are simultaneously present in the Chinese medicinal plant, Inula hupehensis. However, how these related yet distinct STL stereo-isomers are co-synthesized in I. hupehensis remains unknown. Here, we describe the functional identification of the I. hupehensis cytochrome P450 (CYP71BL6) that can catalyze the hydroxylation of GAA in either 8a-or 8b-configuration, resulting in the synthesis of both 8a-and 8b-hydroxyl GAAs. Of these two products, only 8a-hydroxyl GAA spontaneously lactonizes to the C12,8a-STL while the 8b-hydroxyl GAA remains stable without lactonization. Chemical structures of the C12,8a-STL, named inunolide, and 8b-hydroxyl GAA were fully elucidated by nuclear magnetic resonance analysis and mass spectrometry. The CYP71BL6 displays 63-66% amino acid identity to the previously reported CYP71BL1/2 catalyzing GAA 6a-or 8b-hydroxylation, indicating CYP71BL6 shares the same evolutionary lineage with other stereoselective cytochrome P450s, but catalyzes hydroxylation in a non-stereoselective manner. We observed that the CYP71BL6 transcript abundance correlates closely to the accumulation of C12,8-STLs in I. hupehensis. The identification of CYP71BL6 provides an insight into the biosynthesis of STLs in Asteraceae.

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

Abstract: HighlightCYP71BE5 from grapevine was identified as a sesquiterpene oxidase capable of transforming α-guaiene to (−)-rotundone, responsible for the characteristic spicy aroma in wines.

Cited by 56 publications

References 66 publications

On-vine grape drying combined with irrigation allows to produce red wines with enhanced phenolic and rotundone concentrations

On-vine grape drying combined with irrigation allows to produce red wines with enhanced phenolic and rotundone concentrations

Patterns of within-vineyard spatial variation in the ‘pepper’ compound rotundone are temporally stable from year to year

Discovery of a non‐stereoselective cytochrome P450 catalyzing either 8α‐ or 8β‐hydroxylation of germacrene A acid from the Chinese medicinal plant, Inula hupehensis

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