Vomifoliol 9-O-β-d-glucopyranosyl-4-O-β-d-xylopyranosyl-6-O-β-d-glucopyranoside: A trisaccharide glycoside from apple fruit

Herderich, Markus; Feser, Werner; Schreier, Peter

doi:10.1016/0031-9422(92)80035-d

Cited by 11 publications

(4 citation statements)

References 16 publications

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“…An additional β-d-glucose has been identified as the terminal sugar moiety of volatile aroma disaccharide glycosides in other plants (Winterhalter and Skouroumounis 1997). In addition, although identified in other plants, such as tomato (Tikunov et al 2010) and apple (Herderich et al 1992), to date, no higher order saccharides beyond disaccharides have been identified as glycosylated to volatile aroma compounds in grape.…”

Section: Structures Of Glycosidesmentioning

confidence: 99%

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

Hjelmeland

Ebeler

2014

Am. J. Enol. Vitic.

137

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%

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

Hjelmeland

Ebeler

2014

Am. J. Enol. Vitic.

137

114

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“…Analysis of MS/MS spectra of these glycosides revealed two major sugar moieties conjugated to guaiacol, MeSA, and eugenol: (1) a dihexose-pentose moiety, and (2) a malonyl dihexose-pentose moiety. Triglycosides of volatiles consisting of different sugar combinations have been reported in plants before (Herderich et al, 1992;Bilia et al, 1994;Kijima et al, 1997). Also, malonylation of sugar moieties is a common feature in several plants (Withopf et al, 1997;Kazuma et al, 2003;D'Auria et al, 2007;Kogawa et al, 2007).…”

Section: Emission Of Php Volatiles From Tomato Fruit Upon Tissue Disrmentioning

confidence: 99%

A Role for Differential Glycoconjugation in the Emission of Phenylpropanoid Volatiles from Tomato Fruit Discovered Using a Metabolic Data Fusion Approach

Tikunov

Vos²,

González-Paramás³

et al. 2009

Plant Physiology

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A role for differential glycoconjugation in the emission of phenylpropanoid volatiles from ripening tomato fruit (Solanum lycopersicum) upon fruit tissue disruption has been discovered in this study. Application of a multiinstrumental analytical platform for metabolic profiling of fruits from a diverse collection of tomato cultivars revealed that emission of three discriminatory phenylpropanoid volatiles, namely methyl salicylate, guaiacol, and eugenol, took place upon disruption of fruit tissue through cleavage of the corresponding glycoconjugates, identified putatively as hexose-pentosides. However, in certain genotypes, phenylpropanoid volatile emission was arrested due to the corresponding hexose-pentoside precursors having been converted into glycoconjugate species of a higher complexity: dihexose-pentosides and malonyl-dihexose-pentosides. This glycoside conversion was established to occur in tomato fruit during the later phases of fruit ripening and has consequently led to the inability of red fruits of these genotypes to emit key phenylpropanoid volatiles upon fruit tissue disruption. This principle of volatile emission regulation can pave the way to new strategies for controlling tomato fruit flavor and taste.

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“…HR-MS detected a protonated molecule at m/z 387.2021 [M + H] + (calc C 19 H 31 O 9 ). This compound has been assigned as roseoside according to literature values (Herderich et al, 1992; Otsuka et al, 1995; Shen and Terazawa, 2001).…”

Section: Resultsmentioning

confidence: 99%

C13 Megastigmane Derivatives From Epipremnum pinnatum: β-Damascenone Inhibits the Expression of Pro-Inflammatory Cytokines and Leukocyte Adhesion Molecules as Well as NF-κB Signaling

et al. 2019

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In order to identify active constituents and to gain some information regarding their mode of action, extracts from leaves of Epipremnum pinnatum were tested for their ability to inhibit inflammatory gene expression in endothelial- and monocyte-like cells (HUVECtert and THP-1, respectively). Bioactivity-guided fractionation using expression of PTGS2 (COX-2) mRNA as a readout resulted in the isolation of two C13 megastigmane glycosides, gusanlungionoside C (1) and citroside A (3), and the phenylalcohol glycoside phenylmethyl-2-O-(6-O-rhamnosyl)-ß-D-galactopyranoside (2). Further analysis identified six additional megastigmane glycosides and the aglycones β-damascenone (10), megastigmatrienone (11), 3-hydroxy-β-damascenone (12), and 3-oxo-7,8-dihydro-α-ionol (13). Pharmacological analysis demonstrated that 10 inhibits LPS-stimulated induction of mRNAs encoding for proinflammatory cytokines and leukocyte adhesion molecules, such as TNF-α, IL-1β, IL-8, COX-2, E-selectin, ICAM-1, and VCAM-1 in HUVECtert and THP-1 cells. 10 inhibited induction of inflammatory genes in HUVECtert and THP-1 cells treated with different agonists, such as TNF-α, IL-1β, and LPS. In addition to mRNA, also the upregulation of inflammatory proteins was inhibited by 10 as demonstrated by immune assays for cell surface E-selectin and secreted TNF-α. Finally, using a luciferase reporter construct, it was shown, that 10 inhibits NF-κB-dependent transcription. Therefore, we hypothesize that inhibition of NF-κB by β-damascenone (10) may represent one of the mechanisms underlying the in vitro anti-inflammatory activity of Epipremnum pinnatum extracts.

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Vomifoliol 9-O-β-d-glucopyranosyl-4-O-β-d-xylopyranosyl-6-O-β-d-glucopyranoside: A trisaccharide glycoside from apple fruit

Cited by 11 publications

References 16 publications

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

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

A Role for Differential Glycoconjugation in the Emission of Phenylpropanoid Volatiles from Tomato Fruit Discovered Using a Metabolic Data Fusion Approach

C13 Megastigmane Derivatives From Epipremnum pinnatum: β-Damascenone Inhibits the Expression of Pro-Inflammatory Cytokines and Leukocyte Adhesion Molecules as Well as NF-κB Signaling

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