Enzymatic preparation of melibiose and alkyl β-d-fructofuranosides by commercial lactase

Smrtičová, Hana; Čanigová, Margita; Mastihubová, Mária; Mastihuba, Vladimı́r

doi:10.1016/j.molcatb.2011.04.024

Cited by 10 publications

(8 citation statements)

References 22 publications

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“…Our goal was to find a commercial enzyme preparation that can be used for transfructosylation of tyrosol. Several enzyme preparations used in the food industry possess fructosyltransferase side activity and were applied to the preparation of fructooligosaccharides (FOS) or alkyl β‐ d ‐fructofuranosides . For this reason, a wide screening of commercially available enzyme preparations was carried out.…”

Section: Resultsmentioning

confidence: 99%

Screening of Commercial Enzymes for Transfructosylation of Tyrosol: Effect of Process Conditions and Reaction Network

Hollá

Antošová

Karkeszová

et al. 2019

Biotechnology Journal

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Enzymatic fructosylation of organic acceptors other than saccharides brings new possibilities to synthesize molecules that do not exist in nature. The introduction of fructosyl moiety may lead to glycosides possessing enhanced physicochemical and bioactive properties which could be useful in the pharmaceutical and cosmetic industry. In this work, the regioselective synthesis of tyrosol β‐d‐fructofuranoside (TF) catalyzed by β‐fructofuranosidase is investigated. In the first step, 32 commercial enzyme preparations are screened for fructoside‐hydrolyzing activity. The most active preparations are subsequently examined for fructofuranosyl transfer from sucrose to tyrosol. The best candidate, Novozym 188, is chosen to study the effect of reaction conditions on the product formation in a batch reactor. The effects of substrate concentration, temperature, pH, time, and enzyme dosage on the concentration of TF produced are studied using the design of experiments methodology. The maximal product concentration of 3.8 g L−1 is achieved for the sucrose concentration of 1.5 m, tyrosol concentration of 29 g L−1, temperature of 41 °C, and pH 5.1. Besides the main transfructosylation reaction between sucrose and tyrosol, several side reactions take place. A reaction network includes also the formation of fructooligosaccharides and the hydrolysis of sucrose and all reaction products.

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Section: Resultsmentioning

confidence: 99%

Screening of Commercial Enzymes for Transfructosylation of Tyrosol: Effect of Process Conditions and Reaction Network

Hollá

Antošová

Karkeszová

et al. 2019

Biotechnology Journal

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“…[12] The bioactivity and pharmacological research of the n-butyl-β-D-fructofuranoside mainly focus on transfructosylation activity,[13] and little is known about its antitumor effects. Our study on its antiproliferation activity indicated that the n-butyl-β-D-fructofuranoside significantly inhibited the proliferation of Bel-7402 cells in both time- and dose-dependent manner.…”

Section: Discussionmentioning

confidence: 99%

“…The n-butyl-β-D-fructofuranoside is generally available from plants, such as: Smilax glabra,[ 8 ] Brassica rapa,[ 9 ] songaricum,[ 10 ] and easily synthesized from Bacillus subtilis,[ 11 ] Lactozyme. [ 12 ] The bioactivity and pharmacological research of the n-butyl-β-D-fructofuranoside mainly focus on transfructosylation activity,[ 13 ] and little is known about its antitumor effects. Our study on its antiproliferation activity indicated that the n-butyl-β-D-fructofuranoside significantly inhibited the proliferation of Bel-7402 cells in both time- and dose-dependent manner.…”

Section: Discussionmentioning

confidence: 99%

Antiproliferative effects of n-butyl-β-D-fructofuranoside from Kangaisan on Bel-7402 cells

Lou

et al. 2014

Indian J Pharmacol

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Aims:Kangaisan is a powdered compound prescription of Traditional Chinese Medicine which has been used in cancers for many years in Hubei province, China. The purpose of this study was to investigate the antitumor effects of Kangaisan and screen bioactive components.Materials and Methods:3-(4,5-Dimethythiazol-2-yl)-2,5 diphenyl-tetrazolium bromide (MTT) assay, flow cytometry, DNA (Deoxyribonucleic acid) fragmentation assay, Western blot, and real time-polymerase chain reaction were used to investigate the antiproliferation effect of n-butyl-β-D-fructofuranoside on Bel-7402 cells.Statistical Analysis:All experiments were performed in triplicate and the results were expressed as mean ± standard deviation. Statistical analysis was performed with analysis of variance using Origin 8.0 software.Results:It was illustrated that treatment of Bel-7402 cells with various concentrations of n-butyl-β-D-fructofuranoside resulted in growth inhibition in both a dose-dependent and time-dependent manner. The arrest of G0/G1 phase was also induced (P < 0.05). The increasing of sub-G1 cell population indicated the apoplectic characteristic (P < 0.05). Furthermore, the emerging of DNA fragmentation and the increase of Bax/Bcl-2 ratio and p53 expression suggested the possible mitochondrial apoptotic pathway (P < 0.05).Conclusions:The results illustrate that Kangaisan showed anticancer effects and n-butyl-β-D-fructofuranoside extracted from Kangaisan can suppress Bel-7402 cells via interfering cell cycle and by inducing apoptosis.

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“…Among these enzymes, β-fructofuranosidase (also called invertase, EC 3.2.1.26), a member of glycoside hydrolase family 68 (GH68) that catalyzes the hydrolysis and transfructosylation of sucrose, has been reported to catalyze the hydrolysis of raffinose (α- d -galactopyranosyl-(1→6)-α- d -glucopyranosyl-(1→2)-β- d -fructofuranoside) to produce melibiose . A commercial lactase named Lactozyme 3000L (Novozymes, produced by Klyuveromyces lactis) has also been found to possess β-fructofuranosidase activity and converts raffinose to melibiose …”

Section: Introductionmentioning

confidence: 99%

“…8 A commercial lactase named Lactozyme 3000L (Novozymes, produced by Klyuveromyces lactis) has also been found to possess β-fructofuranosidase activity and converts raffinose to melibiose. 9 In addition to those enzymes described above, levansucrase (EC 2.4.1.10, sucrose:2,6-β-D-fructan 6-β-D-fructosyltransferase), which is also a member of GH68 that catalyzes the formation of levan and fructooligosaccharides (FOS) from sucrose, could also catalyze the synthesis of melibiose from raffinose. 10 The crystal structure of levansucrase complexed with sucrose obtained from Bacillus subtilis was the earliest crystal structure resolved and reported across the entire GH68 family, 11 which was followed by the resolutions of the 3D structure of levansucrase from Gluconacetobacter diazotrophicus, 12 Bacillus megaterium, 13 and Erwinia anylovora.…”

Section: ■ Introductionmentioning

confidence: 99%

Enzymatic Production of Melibiose from Raffinose by the Levansucrase from Leuconostoc mesenteroides B-512 FMC

Liu

et al. 2017

J. Agric. Food Chem.

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Melibiose, which is an important reducing disaccharide formed by α-1,6 linkage between galactose and glucose, has been proven to have beneficial applications in both medicine and agriculture. In this study, a characterized levansucrase from Leuconostoc mesenteroides B-512 FMC was further used to study the bioproduction of melibiose from raffinose. The reaction conditions were optimized for melibiose synthesis. The optimal pH, temperature, substrate concentration, ratio of substrates, and units of enzymes were determined as pH 6.0, 45 °C, 210 g/L, 1:1 (210 g/L:210 g/L), and 5 U/mL, respectively. The transfructosylation product of raffinose was determined to be melibiose by FTIR and NMR. A high raffinose concentration was found to strongly favor the production of melibiose. When 210 g/L raffinose and 210 g/L lactose were catalyzed using 5 U/mL purified levansucrase at pH 6.0 and 45 °C, the maximal yield of melibiose was 88 g/L.

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Enzymatic preparation of melibiose and alkyl β-d-fructofuranosides by commercial lactase

Cited by 10 publications

References 22 publications

Screening of Commercial Enzymes for Transfructosylation of Tyrosol: Effect of Process Conditions and Reaction Network

Screening of Commercial Enzymes for Transfructosylation of Tyrosol: Effect of Process Conditions and Reaction Network

Antiproliferative effects of n-butyl-β-D-fructofuranoside from Kangaisan on Bel-7402 cells

Enzymatic Production of Melibiose from Raffinose by the Levansucrase from Leuconostoc mesenteroides B-512 FMC

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