2,5-Dimethyl-4-hydroxy-3(2<i>H</i>)-furanone and Derivatives in Strawberries During Ripening

Sanz, Carlos; Richardson, D.G.; Pérez, Antonio José

doi:10.1021/bk-1995-0596.ch024

Cited by 34 publications

(36 citation statements)

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“…It has been reported that furaneol (2,5-dimethyl-4-hydroxy-furane) is the most important component for the strawberry aroma [9,15]. Our results indicated the furaneol concentration to be quite fluctuating throughout the ripening process, probably due to its metabolism.…”

Section: Resultsmentioning

confidence: 50%

“…A small number of researchers have focused their work on changes in the profile of volatile compounds during fruit ripening [6,7,8,9,10]. During the ripening process the capacity to esterify 1-pentanol is developed by the fruit, presumably by enzymatic reactions, although the enzymes responsible have not yet been characterized [6].…”

Section: Introductionmentioning

confidence: 99%

“…The concentration of volatile compounds increased during ripening of Chandler strawberries, and ethyl hexanoate, ethyl butanoate and methyl butanoate were the predominant components present in the fully ripe fruit [8]. The relationship between the degree of maturity and the concentration of 2,5-dimethyl-4-hydroxy-3(2H)-furanone and its derivatives has been investigated in seven strawberry varieties by Sanz et al [9].…”

Section: Introductionmentioning

confidence: 99%

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Changes in flavour and texture during the ripening of strawberries

Azodanlou¹,

Darbellay²,

Luisier³

et al. 2004

European Food Research and Technology

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The amount of total volatile compounds, total acidity, total sugar content (degrees Brix) and fruit firmness were used to characterize the degree of ripeness of three strawberry varieties (Carezza, Darselect and Marmolada). A novel concept using solid phase microextraction (SPME) and measurement of total volatile compounds to distinguish between various stages of strawberry ripeness was applied. The carboxene/polydimethylsiloxane SPME fibre was found to be best suited to differentiate between the stages of ripeness. The amount of total volatile compounds rapidly increased near to maturity (between the three-quarters red stage and the dark-red stage). Most of the volatile compounds identified were esters, followed by aldehydes, and alcohols. The most abundant volatile compounds were propyl butanoate, 3-phenyl-1-propanol, butyl butanoate, isobutyl butanoate, 3-methyl butyl butanoate and isopropyl hexanoate. The concentration of green aroma components such as hexanal, trans-2-hexenol and cis-3-hexenyl acetate progressively decreased during the maturation process until they became minor components in mature strawberries.

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Section: Resultsmentioning

confidence: 50%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Changes in flavour and texture during the ripening of strawberries

Azodanlou¹,

Darbellay²,

Luisier³

et al. 2004

European Food Research and Technology

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“…Therefore, it is concluded that, when cells are grown in conditions that do not favour cell division (eg when the fruit is fully grown), the Ñavour production can be switched on. This conclusion is supported by the report that DMHF and derivatives levels increase sharply during strawberry fruit ripening, when fruit growth is almost completed (Sanz et al 1993). It is also reported that, when strawberry cells were provided with nutrients in minimal quantities, growth is not favoured and they could produce Ñavour compounds (Dziezak 1986).…”

Section: Tissue Culturesmentioning

confidence: 71%

Strawberry Flavour: Analysis and Biosynthesis

Zabetakis

Holden

1997

J. Sci. Food Agric.

201

137

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“…Only recently, it was shown that the SAAT (for strawberry alcohol acylCoA transferase) and FaNES (for Fragaria 3 ananassa nerolidol synthase) genes are involved in strawberry fruit ester and terpene formation, respectively (Aharoni et al, 2000(Aharoni et al, , 2004 and that FaOMT (for Fragaria 3 ananassa O-methyltransferase) encodes an O-methyltransferase responsible for DMMF biosynthesis Wein et al, 2002). The first indications for the enzymatic formation of HDMF in strawberry fruit were provided by studies demonstrating the correlation of fruit ripening stage and HDMF concentration (Sanz et al, 1995). Incorporation experiments showed that, after the application of 15 different water-soluble, radioactively labeled substances, D-[U-14 C]fructose-1,6-diphosphate had the highest incorporation rate into the furanone structures (Roscher et al, 1998) (Schwab, 1998), and studies with D-[2-2 H]glucose demonstrated the involvement of phosphohexose isomerase in the conversion of D-glucose to the furanones, thus confirming the proposal that D-fructose-6-phosphate is a natural precursor of HDMF and DMMF (Wein et al, 2001).…”

Section: Introductionmentioning

confidence: 99%

FaQR, Required for the Biosynthesis of the Strawberry Flavor Compound 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, Encodes an Enone Oxidoreductase

Raab

López‐Ráez

Klein³

et al. 2006

Plant Cell

161

159

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The flavor of strawberry (Fragaria 3 ananassa) fruit is dominated by an uncommon group of aroma compounds with a 2,5-dimethyl-3(H)-furanone structure. We report the characterization of an enzyme involved in the biosynthesis of 4-hydroxy-2,5-dimethyl-3(2H)-furanone (HDMF; Furaneol), the key flavor compound in strawberries. Protein extracts were partially purified, and the observed distribution of enzymatic activity correlated with the presence of a single polypeptide of ;37 kD. Sequence analysis of two peptide fragments showed total identity with the protein sequence of a strongly ripeninginduced, auxin-dependent putative quinone oxidoreductase, Fragaria 3 ananassa quinone oxidoreductase (FaQR). The open reading frame of the FaQR cDNA consists of 969 bp encoding a 322-amino acid protein with a calculated molecular mass of 34.3 kD. Laser capture microdissection followed by RNA extraction and amplification demonstrated the presence of FaQR mRNA in parenchyma tissue of the strawberry fruit. The FaQR protein was functionally expressed in Escherichia coli, and the monomer catalyzed the formation of HDMF. After chemical synthesis and liquid chromatography-tandem mass spectrometry analysis, 4-hydroxy-5-methyl-2-methylene-3(2H)-furanone was confirmed as a substrate of FaQR and the natural precursor of HDMF. This study demonstrates the function of the FaQR enzyme in the biosynthesis of HDMF as enone oxidoreductase and provides a foundation for the improvement of strawberry flavor and the biotechnological production of HDMF.

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2,5-Dimethyl-4-hydroxy-3(2H)-furanone and Derivatives in Strawberries During Ripening

Cited by 34 publications

References 0 publications

Changes in flavour and texture during the ripening of strawberries

Changes in flavour and texture during the ripening of strawberries

Strawberry Flavour: Analysis and Biosynthesis

FaQR, Required for the Biosynthesis of the Strawberry Flavor Compound 4-Hydroxy-2,5-Dimethyl-3(2H)-Furanone, Encodes an Enone Oxidoreductase

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