Synthesis of hydroxycinnamoyl β-d-xylopyranosides and evaluation of their antioxidant properties

Shimotori, Yasutaka; Hoshi, Masayuki; Soga, Kouji; Osawa, Yosuke; Miyakoshi, Tetsuo

doi:10.1016/j.carres.2013.12.014

Cited by 6 publications

(11 citation statements)

References 35 publications

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“…In addition, sinapic acid and ferulic acid have also been grafted to cellulose and xylan, and these prepared polymers displayed good antioxidant activity in inhibiting lipid peroxidation (Trombino et al ., ; Wrigstedt et al ., ). A possible explanation for the higher inhibition potential in the lipid peroxidation assay in this study might be an elevation in the solubility of the test media (Kylli et al ., ; Shimotori et al ., ). Overall, the assays of antioxidant property in this study revealed that hydroxycinnamoyl maltodextrin derivatives were very potent antioxidants.…”

Section: Resultsmentioning

confidence: 99%

“…Many modified polysaccharides have recently been developed as natural macromolecular antioxidants. For example, chitosan, cellulose, oligosaccharide, starch and xylan have been developed as novel potential antioxidants (Kylli et al ., ; Shimotori et al ., , ; Chatterjee et al ., ). Accordingly, the introduction of hydroxycinnamic acid onto maltodextrin provides a new function to a polysaccharide that is widely used in the food and drug industries.…”

Section: Resultsmentioning

confidence: 99%

“…In previous studies, considerable research efforts were focused on the development of these functional food materials. Among them, a serial of phenolic compounds were grafted onto starch, xylan, chitosan and cellulose, and their antioxidant properties were validated (Mathew & Abraham, 2007;Wrigstedt et al, 2010;Shimotori et al, 2012Shimotori et al, , 2014Phan et al, 2015;Woranuch et al, 2015). Those modified polysaccharides, which played an efficient role in drug delivery and nutrition, have seldom been used for food encapsulation.…”

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confidence: 99%

“…Ferulic acid, vanillic acid and caffeic acid, three common hydroxycinnamic acids, served as functional grafting groups were most commonly used to modify some polysaccharides. It has been reported that caffeic acid and ferulic acid can graft onto starch, chitosan and xylan, and the antioxidant activities of the polysaccharides derivatives have been determined (Mathew & Abraham, 2007;Shimotori et al, 2014;Woranuch et al, 2015). Similarly, chitosan vanillic acid conjugate has been developed due to a variety of pharmacological activities of vanillic acid (Chatterjee et al, 2015).…”

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confidence: 99%

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Synthesis and antioxidant property of hydroxycinnamoyl maltodextrin derivatives

Hou

et al. 2016

Int J of Food Sci Tech

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Summary This study was focused on developing new hydroxycinnamoyl maltodextrin derivatives to evaluate their antioxidant activity and cytotoxicity. Vanillic acid, caffeic acid and ferulic acid were covalently attached to maltodextrin. The prepared derivatives were confirmed by ATR‐IR and 1H‐NMR. The thermal characteristics and viscosity were measured by thermogravimetric analysis and viscometer, respectively, and the studies revealed the grafted maltodextrins to be more thermal stable and viscous than the native maltodextrin. Moreover, the scavenging ability of most of the products was higher than 60% at 1 mg mL−1 against DPPH radical. The inhibitory effect of lipid peroxidation of caffeic acid and ferulic acid grafted maltodextrins attained 85% at 0.5 mg mL−1. It was also found that these compounds had no toxic effect (up to 100 μg mL−1) on the HEK 293 cells through the MTT test. These findings suggested that the prepared derivatives could potentially be used as a nontoxic antioxidant in food and drug industries.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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confidence: 99%

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Synthesis and antioxidant property of hydroxycinnamoyl maltodextrin derivatives

Hou

et al. 2016

Int J of Food Sci Tech

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“…octyl (Entries 2 and 3) 241 or 4-nitrophenyl 243 Regioselective deacetylation using enzymes has also been used as a method for generation of partly acetylated xylosides. Enzymes such as porcine liver esterase (PLE), 244 Novozym 435, 245 lipase PS, 137,239,[246][247] and PEG-modified CCL 248…”

Section: Treatment Of Unprotected D-xylose With Ac2o and Naoac Resultmentioning

confidence: 99%

Chemistry of xylopyranosides

Thorsheim

Siegbahn

Johnsson

et al. 2015

Carbohydrate Research

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Xylose is one of the few monosaccharidic building blocks that are used by mammalian cells. In comparison with other monosaccharides, xylose is rather unusual and, so far, only found in two different mammalian structures, i.e. in the Notch receptor and as the linker between protein and glycosaminoglycan (GAG) chains in proteoglycans. Interestingly, simple soluble xylopyranosides can not only initiate the biosynthesis of soluble GAG chains but also function as inhibitors of important enzymes in the biosynthesis of proteoglycans. Furthermore, xylose is a major constituent of hemicellulosic xylans and thus one of the most abundant carbohydrates on Earth. Altogether, this has spurred a strong interest in xylose chemistry. The scope of this review is to describe synthesis of xylopyranosyl donors, as well as protective group chemistry, modifications, and conformational analysis of xylose.

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Stereospecific, High-Yielding, and Green Synthesis of β-Glycosyl Esters

Feng

2015

J. Agric. Food Chem.

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A new method of synthesizing β-glycosyl esters stereospecifically has been developed by treating O-benzyl-protected glycosyl chlorides with Cs2CO3, tetrabutylammomium bromide (TBAB), a carboxylic acid, water, and granular polytetrafluoroethylene (PTFE) at 80 °C under mechanical agitation. D-Glucosyl, D-xylosyl, and D-galactosyl chlorides and 20 carboxylic acids were used to demonstrate the scope of the reaction. Control experiments showed that the water and granular PTFE had indispensable roles. Water-soluble TBAB has been found to be as efficient as N-methyl-N,N,N-trioctyloctan-1-ammonium chloride (Aliquat 336) in the reactions. After scaling up to 5-12 g, all of the products were obtained quantitatively via simple filtration and no organic solvents or chromatography was needed for the entire process.

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Synthesis of hydroxycinnamoyl β-d-xylopyranosides and evaluation of their antioxidant properties

Cited by 6 publications

References 35 publications

Synthesis and antioxidant property of hydroxycinnamoyl maltodextrin derivatives

Synthesis and antioxidant property of hydroxycinnamoyl maltodextrin derivatives

Chemistry of xylopyranosides

Stereospecific, High-Yielding, and Green Synthesis of β-Glycosyl Esters

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