Identification of 3-hydroxyoctyl β-d-glucoside and absolute configuration of free and bound octane-1,3-diol in apple fruit

Schwab, Wilfried; Scheller, G.; Gerlach, Doris; Schreier, Peter

doi:10.1016/0031-9422(89)85029-0

Cited by 27 publications

(19 citation statements)

References 5 publications

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“…A still relatively new compound is 1,3-octanediol. So far, it has only been reported in apple flavor and French cider (51)(52)(53). In a very recent publication its presence in pear flavor was described (54).…”

Section: Strawberry a Further Fruit Investigated In Our Laboratoriesmentioning

confidence: 99%

The Importance of the Vacuum Headspace Method for the Analysis of Fruit Flavors

Güntert¹,

Krammer²,

Sommer³

et al. 1998

ACS Symposium Series

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The Vacuum Headspace Method is a very gentle work-up procedure especially suited for the analysis of fruits. Comparison of the Simultaneous Distillation-Extraction Method, the Dynamic Headspace Method, and the Vacuum Headspace Method shows clearly the superior performance of the latter with respect to the sensory impression of the resulting extracts. Sensory evaluation of the vacuum headspace extracts of various fruits (e.g., passion fruit, strawberry, pear, peach, raspberry, cherry) leads to very fruit-typical descriptions. Consequently, the qualitative and quantitative flavor patterns of the analyzed fruits represent the genuine fruit flavors very well.The comparison of the different work-up procedures is explained in detail. Moreover, the volatile constituents of various analyzed fruits are shown and discussed. The importance of individual flavor compounds for the respective fruit flavor is indicated. It is explained how these results can serve as the basis for the composition of a new type of fresh-fruit flavors.The analysis of food flavors has been dramatically improved over the past 30 years, mainly through the invention of new work-up procedures, modern separation techniques (high resolution gas chromatography on fused silica capillaries, high performance liquid chromatography), and more sensitive spectroscopic methods (nuclear magnetic resonance, mass spectrometry, fourier transform infrared spectroscopy) some of them being available as hyphenated techniques (HRGC-MS, HRGC-FTIR). This continuous development has, over the years, led to results and publications about virtually every food flavor. Thousands of flavor compounds have been identified in the different foods and are collected in libraries (7).

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Section: Strawberry a Further Fruit Investigated In Our Laboratoriesmentioning

confidence: 99%

The Importance of the Vacuum Headspace Method for the Analysis of Fruit Flavors

Güntert¹,

Krammer²,

Sommer³

et al. 1998

ACS Symposium Series

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“…Concentrations of 1.6 -14.4 mg/kg and Table 1mConcentration of octane-1,3-diol (1), ethyl 3-hydroxyoctanoate (2), methyl 3-hydroxyoctanoate (3), 5(Z)-octene-1,3-diol (4), ethyl 5(Z)-3-hydroxyoctenoate (5) and 1,3-dioxanes (6 -9) in pear fruits (Pyrus communis L.) 0.2 -1.9 mg/kg for 1 and 2, respectively, were detected in seven (1) and two (2) of the pear cultivars under study. Until now, 1 and 4 have only been described as natural ingredients of apples [1,2] and mountain papaya [6]. Two pear cultivars also contained high amounts of 2, 3 and 5 (Table 1).…”

Section: Resultsmentioning

confidence: 99%

“…The 1,3-diols exhibit antimicrobial activity against bacteria and yeast but are harmless to humans [3]. Recent analyses revealed the presence of enantiomerically pure (R)-(+) octane-1,3-diol and (R)-3-hydroxyoctyl β-D-glucopyranoside in the cultivar Jonathan [2]. Both diols are considered intermediated of fatty acid metabolism.…”

Section: Introductionmentioning

confidence: 97%

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Octane-1,3-diol and its derivatives from pear fruits

Beuerle

Schwab

1997

Zeitschrift f�r Lebensmitteluntersuchung und -Forschung A

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AbstractmIn extracts obtained by liquid-liquid extraction from seven pear (Pyrus communis L.) cultivars, octane-1,3-diol, 5(Z)octene-1,3-diol, methyl 3-hydroxyoctanoate, ethyl 3-hydroxyoctanoate and ethyl 5(Z)-3-hydroxyoctenoate were identified by capillary gas chromatography-mass spectrometry. Evaluation of the absolute configuration was achieved by multidimensional gas chromatography, using a polar achiral column (DB-Wax) and a chiral main column (2,3-di-O-acetyl-6-O-tert-butyldimethylsilyl-β-cyclodextrin/OV 1701). Comparison of retention times of synthesized optically enriched reference compounds with those of isolated diols and hydroxy esters revealed (R)-configurations for the 3-hydroxy derivatives, exhibiting enantiomeric excesses greater than 99%. In addition, (2S, 4R)-and (2R, 4R)-2-methyl-4-pentyl-1,3-dioxane as well as (2S, 4R)-and (2R, 4R)-2-methyl-4-(29(Z)-pentenyl)-1,3-dioxane, products formed by acetaldehyde and octane-1,3-diol or 5(Z)-octene-1,3-diol, respectively, were detected in pear fruits.

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“…Several apple cultivars such as Peau de Chien, Douce Moen, and Rheinischer Bohnapfel accumulate high concentrations of the antimicrobial β-glycols R-octane-1,3-diol and its unsaturated analog R-5(Z)-octene-1,3-diol, as well as their glucosylated forms during storage (1)(2)(3). The diols are effective in controlling microorganisms associated with infections in humans and animals (4).…”

mentioning

confidence: 99%

Biosynthesis of R‐(+)‐octane‐1’3‐diol. Crucial role of β‐oxidation in the enantioselective generation of 1’3‐diols in stored apples

Beuerle

Schwab

1999

Lipids

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The biosynthesis of R-octane-1,3-diol and R-5(Z)-octene-1,3-diol, two natural antimicrobial agents in apples and pears, was investigated in stored apples after application of [9,10,12,13-3H]linoleic acid, [9,10,12,13,15,16-3H]linolenic acid, [1-14C]linoleic acid, [U-14C]oleic acid, lipoxygenase-derived metabolites of [9,10,12,13-3H]linoleic acid, 13C18-labeled linoleic acid hydroperoxides, and 2H-labeled octanol derivatives. Analysis of the products and quantification of incorporation and labeling pattern were achieved by high-performance liquid chromatography-radiodetection, capillary gas chromatography (GC)-isotope ratio mass spectrometry, and GC-mass spectrometry analysis. Almost all the applied precursors were partly transformed into R-octane-1,3-diol. Linoleic acid derivatives, still containing the 12,13 cis double bond, and octanol derivatives oxy-functionalized at carbon 3 were the most efficient precursors of the 1,3-diol. The data imply that R-octane-1,3-diol is generated in stored apples in the course of the beta-oxidation from R-3-hydroxy-octanoyl-SCoA originating from 2-cis-octenoyl-SCoA by enoyl-CoA hydratase. In an analogous fashion, R-5(Z)-octene-1,3-diol is formed from the unsaturated intermediate.

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Identification of 3-hydroxyoctyl β-d-glucoside and absolute configuration of free and bound octane-1,3-diol in apple fruit

Cited by 27 publications

References 5 publications

The Importance of the Vacuum Headspace Method for the Analysis of Fruit Flavors

The Importance of the Vacuum Headspace Method for the Analysis of Fruit Flavors

Octane-1,3-diol and its derivatives from pear fruits

Biosynthesis of R‐(+)‐octane‐1’3‐diol. Crucial role of β‐oxidation in the enantioselective generation of 1’3‐diols in stored apples

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