Glycosidically bound aroma compounds from two strawberry fruit species, <i>Fragaria vesca f. semperflorens</i> and <i>Fragaria X ananassa</i>, cv. Korona

Wintoch, Herbert; Krammer, Gerhard; Schreier, Peter

doi:10.1002/ffj.2730060309

Cited by 24 publications

(14 citation statements)

References 13 publications

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“…The role of glucosides as precursors of important Ñavour components has been underestimated. However, recognition of their presence and role has grown (Mayerl et al 1989 ;Wu et al 1990aWu et al ,b, 1991Wintoch et al 1991 ;Zabetakis and Holden 1996). The derivatisation of glucosides renders them more volatile and more soluble in organic solvents.…”

Section: Identiðcation and Quantiðcation Of ñAvour Compoundsmentioning

confidence: 97%

“…The derivatised glucosides can be extracted thereafter into the organic phase and analysed by GLC. The analysis of glycosidically bound aroma compounds from two strawberry fruit species after their hydrolysis has been reported (Wintoch et al 1991). The analysis of the glucosides was performed after their per-O-methylation.…”

Section: Identiðcation and Quantiðcation Of ñAvour Compoundsmentioning

confidence: 99%

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Strawberry Flavour: Analysis and Biosynthesis

Zabetakis

Holden

1997

J. Sci. Food Agric.

201

137

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Section: Identiðcation and Quantiðcation Of ñAvour Compoundsmentioning

confidence: 97%

Section: Identiðcation and Quantiðcation Of ñAvour Compoundsmentioning

confidence: 99%

Strawberry Flavour: Analysis and Biosynthesis

Zabetakis

Holden

1997

J. Sci. Food Agric.

201

137

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“…SDS-PAGE confirmed the predicted 65-kD molecular mass of the FaGT2 fusion protein, consisting of a 61.4-kD FaGT2 protein and 3-kD N-terminal tag. Enzyme assays were performed with the purified recombinant protein, and substrates previously identified as glycosylated derivatives in strawberry fruit as well as others not reported (Wintoch et al, 1991). Of the 35 substrates tested, 15 were accepted as substrates by the recombinant enzyme, including benzoic acid, cinnamic acid, and their respective derivatives, whereas about 20 were not accepted, including several flavonoids (quercetin, kaempferol, pelargonidin), alcohols (benzyl alcohol, 2-phenylethanol), nonaromatic acids (2-methylbutyric acid, hexanoic acid, abscisic acid), aromatic acids (indoleacetic acid, naphthylacetic acid [NAA], o-coumaric acid, salicylic acid, 2-amino benzoic acid, gallic acid, Figure 1.…”

Section: Enzymatic Activity Of the Recombinant Fagt2 Enzymementioning

confidence: 99%

Cinnamate Metabolism in Ripening Fruit. Characterization of a UDP-Glucose:Cinnamate Glucosyltransferase from Strawberry

et al. 2006

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Strawberry (Fragaria 3 ananassa) fruit accumulate (hydroxy)cinnamoyl glucose (Glc) esters, which may serve as the biogenetic precursors of diverse secondary metabolites, such as the flavor constituents methyl cinnamate and ethyl cinnamate. Here, we report on the isolation of a cDNA encoding a UDP-Glc:cinnamate glucosyltransferase (Fragaria 3 ananassa glucosyltransferase 2 [FaGT2]) from ripe strawberry cv Elsanta that catalyzes the formation of 1-O-acyl-Glc esters of cinnamic acid, benzoic acid, and their derivatives in vitro. Quantitative real-time PCR analysis indicated that FaGT2 transcripts accumulate to high levels during strawberry fruit ripening and to lower levels in flowers. The levels in fruits positively correlated with the in planta concentration of cinnamoyl, p-coumaroyl, and caffeoyl Glc. In the leaf, high amounts of Glc esters were detected, but FaGT2 mRNA was not observed. The expression of FaGT2 is negatively regulated by auxin, induced by oxidative stress, and by hydroxycinnamic acids. Although FaGT2 glucosylates a number of aromatic acids in vitro, quantitative analysis in transgenic lines containing an antisense construct of FaGT2 under the control of the constitutive 35S cauliflower mosaic virus promoter demonstrated that the enzyme is only involved in the formation of cinnamoyl Glc and p-coumaroyl Glc during ripening.

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“…The loss of the ability to produce a-pinene also leads to the loss of other characteristic flavor components (myrtenol and its derivatives) of wild strawberry species (Wintoch et al, 1991) in cultivated strawberries, despite the fact that the FaPINH gene encoding the enzyme catalyzing the hydroxylation of a-pinene to myrtenol is still expressed in the ripe fruit of the cultivated species.…”

Section: Loss Of Several Monoterpenes Including Myrtenol By the Culmentioning

confidence: 99%

“…Myrtenol, a monoterpene alcohol formed by the C10 hydroxylation of a-pinene (Figures 2A and 2C), has previously been described as one of the few compounds that may contribute to the typical aroma of the wild strawberry species (Honkanen and Hirvi, 1990). By contrast, cultivated strawberry varieties have never been reported to produce or emit myrtenol (Pyysalo et al, 1979;Hirvi and Honkanen, 1982;Honkanen and Hirvi, 1990;Wintoch et al, 1991;Zabetakis and Holden, 1997).…”

Section: The Fvpins Gene Encodes the Enzyme Catalyzing The Biosynthesmentioning

confidence: 99%

Gain and Loss of Fruit Flavor Compounds Produced by Wild and Cultivated Strawberry Species

Aharoni¹,

Giri

Verstappen³

et al. 2004

Plant Cell

438

357

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The blends of flavor compounds produced by fruits serve as biological perfumes used to attract living creatures, including humans. They include hundreds of metabolites and vary in their characteristic fruit flavor composition. The molecular mechanisms by which fruit flavor and aroma compounds are gained and lost during evolution and domestication are largely unknown. Here, we report on processes that may have been responsible for the evolution of diversity in strawberry (Fragaria spp) fruit flavor components. Whereas the terpenoid profile of cultivated strawberry species is dominated by the monoterpene linalool and the sesquiterpene nerolidol, fruit of wild strawberry species emit mainly olefinic monoterpenes and myrtenyl acetate, which are not found in the cultivated species. We used cDNA microarray analysis to identify the F. ananassa Nerolidol Synthase1 (FaNES1) gene in cultivated strawberry and showed that the recombinant FaNES1 enzyme produced in Escherichia coli cells is capable of generating both linalool and nerolidol when supplied with geranyl diphosphate (GPP) or farnesyl diphosphate (FPP), respectively. Characterization of additional genes that are very similar to FaNES1 from both the wild and cultivated strawberry species (FaNES2 and F. vesca NES1) showed that only FaNES1 is exclusively present and highly expressed in the fruit of cultivated (octaploid) varieties. It encodes a protein truncated at its N terminus. Green fluorescent protein localization experiments suggest that a change in subcellular localization led to the FaNES1 enzyme encountering both GPP and FPP, allowing it to produce linalool and nerolidol. Conversely, an insertional mutation affected the expression of a terpene synthase gene that differs from that in the cultivated species (termed F. ananassa Pinene Synthase). It encodes an enzyme capable of catalyzing the biosynthesis of the typical wild species monoterpenes, such as a-pinene and b-myrcene, and caused the loss of these compounds in the cultivated strawberries. The loss of a-pinene also further influenced the fruit flavor profile because it was no longer available as a substrate for the production of the downstream compounds myrtenol and myrtenyl acetate. This phenomenon was demonstrated by cloning and characterizing a cytochrome P450 gene (Pinene Hydroxylase) that encodes the enzyme catalyzing the C10 hydroxylation of a-pinene to myrtenol. The findings shed light on the molecular evolutionary mechanisms resulting in different flavor profiles that are eventually selected for in domesticated species.

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Glycosidically bound aroma compounds from two strawberry fruit species, Fragaria vesca f. semperflorens and Fragaria X ananassa, cv. Korona

Cited by 24 publications

References 13 publications

Strawberry Flavour: Analysis and Biosynthesis

Strawberry Flavour: Analysis and Biosynthesis

Cinnamate Metabolism in Ripening Fruit. Characterization of a UDP-Glucose:Cinnamate Glucosyltransferase from Strawberry

Gain and Loss of Fruit Flavor Compounds Produced by Wild and Cultivated Strawberry Species

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