Novel monoterpene disaccharide glycosides of Vitis vinifera grapes and wines

Williams, Patrick J.; Strauss, Christopher R.; Wilson, B.; Massy‐Westropp, Ralph A.

doi:10.1016/0031-9422(82)83034-3

Cited by 267 publications

(157 citation statements)

References 18 publications

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“…The addition of other sugars to the glucose moiety will form disaccharide, trisaccharide, and higher order saccharide glycosides. In grapes, rhamnose and arabinose (Williams et al 1982a) along with apiose (Voirin et al 1990) have been identified as terminal sugars in disaccharide glycosides. Figure 4 shows the structures of identified glycones in grape, together with their names, and common names, when available.…”

Section: Structures Of Glycosidesmentioning

confidence: 99%

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Glycosidically Bound Volatile Aroma Compounds in Grapes and Wine: A Review

Hjelmeland

Ebeler

2014

Am. J. Enol. Vitic.

143

114

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Volatile aroma compounds in plants are typically found both as "free" and "bound" to a sugar moiety. When bound, these compounds are not odor active; however, upon hydrolysis of the glycoside, these compounds may then be volatilized. In grapes and wine, a large proportion of volatile aroma compounds are found in the bound form. A review of glycosides in grapes and in wine is presented with a focus on identified glycoside structures, their biosynthesis, their potential roles in the plant, and methods for their analysis. Studies of these compounds and their concentration changes during the winemaking process are discussed.

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Section: Structures Of Glycosidesmentioning

confidence: 99%

“…While their presence was suggested in 1974 (Cordonnier and Bayonove 1974), it was not until 1982 that these aroma precursors were first identified in grape (Williams et al 1982a). The first evaluations on the sensory properties of glycosides in grapes and wines were done by Anne Noble and coworkers.…”

mentioning

confidence: 99%

Glycosidically Bound Volatile Aroma Compounds in Grapes and Wine: A Review

Hjelmeland

Ebeler

2014

Am. J. Enol. Vitic.

143

114

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“…A considerable proportion of these compounds are in the bound form in the juice and are released during fermentation by the yeast; however, some can become aromatic by chemical rearrangement such as the non-enzymatic rearrangement of hydroxylated linalool derivatives to give several volatile terpenes, including α-terpineol (Williams et al, 1980;Loscos et al, 2007). The oxidation mechanism is known to play a role in some cases in the release and rearrangement of the terpenes (Williams et al, 1982;Marais, 1983).…”

Section: Monoterpenesmentioning

confidence: 99%

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Coetzee

Toit

2015

SAJEV

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Oxidation and the capacity for sufficient ageing potential of white wines are constant problems for winemakers worldwide. In general, it is accepted that certain grape varieties are especially sensitive to oxidation, suggesting that some of the chemical components key to their sensory attributes are strongly modulated by oxygen exposure. Sauvignon blanc is a well-documented example of an oxygen-sensitive wine, and understanding the stability of various compounds is crucial in order to preserve the fresh and fruity characters of Sauvignon blanc wines while preventing the formation of off-odours over a long period of time. Compounds such as the volatile thiols and methoxypyrazines are key aroma compounds responsible for the typical Sauvignon blanc aroma, while other aroma compounds, such as esters, alcohols and acids, can also contribute to the wine aroma. Oxidation-related compounds (such as aldehydes) can occur under certain conditions and it is essential to understand the chemistry behind oxidation to control and manage the development of various characteristics in wine. The sensory interactions occurring between various compounds (both aromatic and non-aromatic) are also important due to enhancing or suppressive effects that can mask certain aroma nuances. This review focuses on the stability of certain compounds of Sauvignon blanc wines during oxidation and ageing and how it affects the aromatic and non-aromatic composition of these wines. ABBREVIATIONS

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“…Hesperetin 7-glucoside, a product of hesperidin hydrolysis by a-L-rhamnosidase, is an important precursor for sweetener production (Manzanares et al, 2001). Furthermore, there is an increasing interest in the use a-L-rhamnosidases to enhance grape juice and wine flavour by release of free monoterpenes from terpenyl glycosides (Williams et al, 1982). Finally, a-L-rhamnosidases can be used to improve the bioavailability of polyphenols, such as hesperidin (Nielsen et al, 2006).…”

Section: Introductionmentioning

confidence: 99%

Physiological and biochemical characterization of the two α-l-rhamnosidases of Lactobacillus plantarum NCC245

et al. 2009

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This work is believed to be the first report on the physiological and biochemical characterization of a-L-rhamnosidases in lactic acid bacteria. A total of 216 strains representing 37 species and eight genera of food-grade bacteria were screened for a-L-rhamnosidase activity. The majority of positive bacteria (25 out of 35) were Lactobacillus plantarum strains, and activity of the L. plantarum strain NCC245 was examined in more detail. The analysis of a-L-rhamnosidase activity under different growth conditions revealed dual regulation of the enzyme activity, involving carbon catabolite repression and induction: the enzyme activity was downregulated by glucose and upregulated by L-rhamnose. The expression of the two a-L-rhamnosidase genes rhaB1 and rhaB2 and two predicted permease genes rhaP1 and rhaP2, identified in a probable operon rhaP2B2P1B1, was repressed by glucose and induced by L-rhamnose, showing regulation at the transcriptional level. The two a-L-rhamnosidase genes were overexpressed and purified from Escherichia coli. RhaB1 activity was maximal at 50 6C and at neutral pH and RhaB2 maximal activity was detected at 60 6C and at pH 5, with high residual activity at 70 6C. Both enzymes showed a preference for the a-1,6 linkage of L-rhamnose to b-D-glucose, hesperidin and rutin being their best substrates, but, surprisingly, no activity was detected towards the a-1,2 linkage in naringin under the tested conditions. In conclusion, we identified and characterized the strain L. plantarum NCC245 and its two a-L-rhamnosidase enzymes, which might be applied for improvement of bioavailability of health-beneficial polyphenols, such as hesperidin, in humans.

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Novel monoterpene disaccharide glycosides of Vitis vinifera grapes and wines

Cited by 267 publications

References 18 publications

Glycosidically Bound Volatile Aroma Compounds in Grapes and Wine: A Review

Glycosidically Bound Volatile Aroma Compounds in Grapes and Wine: A Review

Sauvignon Blanc Wine: Contribution of Ageing and Oxygen on Aromatic and Non-aromatic Compounds and Sensory Composition : A Review

Physiological and biochemical characterization of the two α-l-rhamnosidases of Lactobacillus plantarum NCC245

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