Synthesis of glycosyl ferulate derivatives by amine-promoted glycosylation with regioselective hydrolysis using Novozym 435 and evaluation of their antioxidant properties

Shimotori, Yasutaka; Tsutano, Kyohei; Soga, Kouji; Osawa, Yosuke; Aoyama, Masakazu; Miyakoshi, Tetsuo

doi:10.1016/j.carres.2012.06.019

Cited by 8 publications

(12 citation statements)

References 40 publications

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“…Ferulic acid (4‐hydroxy‐3‐methoxycinnamic acid, FA, Scheme ), one of the ubiquitous compounds in nature, is present in a wide variety of grains, vegetables and fruits (Shimotori et al., ). Besides, FA is the main active ingredient of traditional Chinese medicinal herbs, such as angelica, asafoetida and white peony root (Mao et al., ).…”

Section: Introductionmentioning

confidence: 99%

Ferulic acid: A natural compound as an efficient feed additive for GIFT (Oreochromis niloticus)

Jiang

et al. 2017

Aquacult Nutr

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This study aimed to investigate the effect of dietary ferulic acid (FA) supplementation on growth performance, antioxidant capacity and some physical characteristics of flesh in genetic improvement of farmed tilapia (GIFT) juveniles. Five diets supplemented with 0, 50, 100, 200 and 400 mg/kg FA were prepared. Weight gain was significantly increased, while feed conversion ratio, viscerosomatic index and hepatosomatic index were significantly decreased in fish fed FA diet at 100 mg/kg feed (p < .05). FA supplementation improved hepatic and serum superoxide dismutase and catalase activities, but decreased the malondialdehyde content (p < .05). Furthermore, with the addition of FA, serum triacylglycerol, cholesterol, low‐density lipoprotein cholesterol contents, alanine aminotransferase and aspartate transaminase activities were reduced, whereas serum high‐density lipoprotein cholesterol content, alkaline phosphatase and lysozyme activities were enhanced. The texture profile analysis parameters and water‐holding capacity tended to increase while cooking loss was decreased by dietary FA supplementation (p < .05). These results suggested that dietary FA supplementation increased the growth performance and antioxidant capacity of GIFT, and improved some physical characteristics of flesh and serum biochemical parameters. The optimum dietary FA level was 100 mg/kg in diet.

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Section: Introductionmentioning

confidence: 99%

Ferulic acid: A natural compound as an efficient feed additive for GIFT (Oreochromis niloticus)

Jiang

et al. 2017

Aquacult Nutr

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“…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%

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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“…1−3 Glycosyl esters are important biocompounds, which occur in tea, 4 fruits, 5,6 and vegetables. 6 They function as antioxidants, 5,6 enzyme inhibitors, 6 anticancer agents, 5,7 and sweeteners such as the well-known food additive stevioside. 8 The following methods are used in the preparation of glycosyl esters all of which start from aldosyl hemiacetals: Schmidt glycosylation, 9,10 Mitsunobu reaction, 11−13 and Steglich esterification.…”

Section: ■ Introductionmentioning

confidence: 99%

“…Glycosylation is an important tool in modifying the properties of bioactive molecules, including the transformation of carboxylic acids such as ursolic acid into glycosyl esters. − Glycosyl esters are important biocompounds, which occur in tea, fruits, , and vegetables . They function as antioxidants, , enzyme inhibitors, anticancer agents, , and sweeteners such as the well-known food additive stevioside .…”

Section: Introductionmentioning

confidence: 99%

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 glycosyl ferulate derivatives by amine-promoted glycosylation with regioselective hydrolysis using Novozym 435 and evaluation of their antioxidant properties

Cited by 8 publications

References 40 publications

Ferulic acid: A natural compound as an efficient feed additive for GIFT (Oreochromis niloticus)

Ferulic acid: A natural compound as an efficient feed additive for GIFT (Oreochromis niloticus)

Synthesis and antioxidant property of hydroxycinnamoyl maltodextrin derivatives

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

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