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Transglycosylation is one of enzymatic methods to improve the physical and biochemical properties of various functional compounds. In this study, stevioside glucosides were synthesized using sucrose as a substrate, stevioside (Ste) as an acceptor, and dextransucrase from Leuconostoc mesenteroides B-512 F/KM. The highest Ste conversion yield of 98% was obtained with 50 mg/mL Ste, 800 mM sucrose, and dextransucrase 4 U/mL at 28 °C for 6 h. The concentration of Ste was unchanged while of Ste-G1 was increased from 7.7 mM to 9.1 mM as the Ste acceptor reaction digest was treated with dextranase from Lipomyces starkeyi. Ste-G1 (13-O-β-sophorosyl-19-O-β-isomaltosyl-steviol), Ste-G2 (13-O-(β-(1→6) glucosyl)-β-glucosylsophorosyl-19-O-β-isomaltosyl-steviol), and Ste-G2' (13-O-β-sophorosyl-19-O-β-isomaltotriosyl-steviol) were determined by NMR. These glucosylated Ste showed increased stabilities at pH 2, 60 °C for 48 h as compared to Ste. Ste-G1, Ste-G2, and Ste-G2' inhibited the insoluble glucan synthesis from sucrose by mutansucrase from Streptococcus muntans by the transfer of the glucosyl group of sucrose to Ste-G1, Ste-G2, and Ste-G2'. The relative water solubility of curcumin, pterostilbene or idebenone was increased by Ste or Ste glucosides treatment. Ste and Ste-G1 restored cell viability in RAW264.7 cells at concentrations up to 8 mg/mL and inhibited nitric oxide production in LPS-induced RAW264.7 cells with IC 50 of 3.29 and 1.87 mg/mL., (Copyright © 2019 Elsevier Inc. All rights reserved.)

Oligosaccharide (OS) is used as a sugar replacement as well as an ingredient in functional foods because of its beneficial effects, mainly on reducing calorie content and promoting intestinal health. By contrast, the effects of OS on inflammation are less well investigated. The purpose of this study was to investigate the effects of sucrose-derived OS on glucose control and inflammation in high fat (HF) diet-fed mice. Male C57BL6 mice were randomly assigned to six treatment groups (n = 10-14 mice per group): 1) lean control (CON), 2) HF control, 3) HF-low sucrose (LS, 100 mg/kg/day), 4) HF-high sucrose (HS, 1000 mg/kg/day), 5) HF-low OS (LOS, 100 mg/kg/day), and 6) HF-high OS (HOS, 1000 mg/kg/day). PBS (vehicle), sucrose, and OS were administered by stomach gavage. Body weight, food intake, and markers of liver function (activities of aspartate aminotransferase and alanine aminotransferase) were not affected by the treatments. HOS treatment decreased levels of serum glucose, insulin, and homeostasis model assessment-insulin resistance compared with sucrose treatment. However, serum adiponectin levels of the HOS group were higher than those of the sucrose groups. Serum levels of the pro-inflammatory cytokines interleukin-6 (IL-6) and fetuin-A were lower in the HOS group than in the sucrose groups. Hepatic gene expression levels of pro-inflammatory cytokines and related factors (fetuin-A, NF-κB, TLR4, TNF-alpha, and IL-6) were decreased and the levels of insulin signaling-related molecules (sirtuin 1, insulin receptor, and Akt) were increased in HOS-treated mice as compared with sucrose-treated mice. These results demonstrate that OS treatment is effective in improving glucose control and inflammation in high fat diet-fed mice., (Copyright © 2016 Elsevier Inc. All rights reserved.)

Over 99% of sucrose in mandarin juice (57.1 g/l in original juice to 428.4 g/l in concentrated juice) was enzymatically converted to glucooligosaccharides using 3 U dextransucrase/ml prepared from Leuconostoc mesenteroides at 28 °C. The oligosaccharide synthesis yields were 51 and 47% for the original and the concentrated mandarin juice, respectively. The degree of polymerization of oligosaccharides in the enzyme-modified juice was 2-7. Calories in the original and modified mandarin juice were 433 and 301 kcal/l (30.5% reduction). Compared with the original juice, the enzyme-modified juice showed 82% decrease of insoluble glucan formation by mutansucrase from Streptococcus mutans. A sensory evaluation of the juices revealed that the original and modified mandarin juices had sweetness values of 4.5 and 4.9 and the same values for overall acceptability.

Reactions of Leuconostoc mesenteroides B-512FMCM dextransucrase with increasing concentrations of sucrose, from 0.1 to 4.0 M, gave a decreasing amount of high-molecular weight dextran (HMWD) (>10(6) Da) with a concomitant increase in low-molecular weight dextran (LMWD) (<10(5) Da). At 0.1 M sucrose, pH 5.5, and 28 degrees C, 99.8% of the dextran had a MW>10(6) Da and at 4.0 M sucrose, 69.9% had a MW<10(5) Da and 30.1% had a MW>10(6) Da, giving a bimodal distribution. The degree of branching increased from 5% for 0.1 M sucrose to 16.6% for 4.0 M sucrose. The temperature had very little effect on the size of the dextran, which was >10(6) Da, but it had a significant effect on the degree of branching, which was 4.8% at 4 degrees C and increased to 14.7% at 45 degrees C. Both the molecular weight (MW) and the degree of branching were not significantly affected by different pH values between 4.5 and 6.0.

The development of consumer-friendly nutraceutical dosage forms is highly important for greater acceptance. In this work, such dosage forms were prepared based on structured emulsions (emulgels), where the olive oil phase was filled within the pectin-based jelly candy. The emulgel-based candies were designed as bi-modal carriers, where oil-soluble curcumin and water-soluble riboflavin were incorporated as the model nutraceuticals. Initially, emulsions were prepared by homogenizing varied concentrations (10% to 30% (w/w)) of olive oil in a 5% (w/w) pectin solution that contained sucrose and citric acid. Herein, pectin acted as a structuring agent-cum-stabilizer. Physico–chemical properties of the developed formulations were thoroughly analyzed. These studies revealed that olive oil interferes with the formation of polymer networks of pectin and the crystallization properties of sugar in candies. This was confirmed by performing FTIR spectroscopy and DSC studies. In vitro disintegration studies showed an insignificant difference in the disintegration behavior of candies, although olive oil concentration was varied. Riboflavin and curcumin were then incorporated into the jelly candy formulations to analyze whether the developed formulations could deliver both hydrophilic and hydrophobic nutraceutical agents. We found that the developed jelly candy formulations were capable of delivering both types of nutraceutical agents. The outcome of the present study may open new directions for designing and developing oral nutraceutical dosage forms. [ABSTRACT FROM AUTHOR]

Gallic acid glycoside was enzymatically synthesized by using dextransucrase and sucrose from gallic acid. After purification by butanol partitioning and preparative HPLC, gallic acid glucoside was detected at m/z 355 (C, H, O, Na) by matrix-assisted laser desorption ionization time-of-flight mass spectrometry. The yield of gallic acid glucoside was found to be 35.7% (114 mM) by response surface methodology using a reaction mixture of 319 mM gallic acid, 355 mM sucrose, and 930 mU/mL dextransucrase. The gallic acid glucoside obtained showed 31% higher anti-lipid peroxidation and stronger inhibition ( Ki = 1.23 mM) against tyrosinase than that shown by gallic acid ( Ki = 1.98 mM). In UVB-irradiated human fibroblast cells, gallic acid glucoside lowered matrix metalloproteinase-1 levels and increased the collagen content, which was indicative of a stronger anti-aging effect than that of gallic acid or arbutin. These results indicated that gallic acid glucoside is likely a superior cosmetic ingredient with skin-whitening and anti-aging functions. [ABSTRACT FROM AUTHOR]

95.3% of the sucrose in a feed batch fermentation (300 g/L) was hydrolyzed by Leuconostoc mesenteroides subp. mesenteroides NRRL B-23188 glucansucrase. Further, the glucose of sucrose formed glucooligosaccharides (GOS) of degree of polymerization (DP) over 2, together with 91.6% of the maltose (200 g/L). Lime saccharate (lime sucrate) was used to control the pH during fermentation. The GOS products had DP between 2 and 7. When Streptococcus mutans mutansucrase (0.1 U/mL) reacted with 0.1% sucrose, addition of 0.1 ~ 10% GOS to the mutansucrase reaction digest resulted in a 56 ~ 90% reduction of mutan formation. GOS also reduced E. coli (72.2%) and Salmonella sp. (over 40.0%) growth, when 2.5% GOS was used as a single carbon source, compared to growth using glucose. The calculated glycemic index and glycemic load of GOS was 8 and 1, respectively, based on a 10 g carbohydrate serving. GOS was calculated to have 2.43 kcal/g. After a glucose tolerance test was performed using C57BL/6 mice, we found that mice treated with GOS showed a 59.4% lower increase in plasma glucose than those treated with maltose. [ABSTRACT FROM AUTHOR]

We have previously demonstrated the production of glucooligosaccharides via a fermentation of sucrose with Leuconostoc mesenteroides NRRL B-742 using sodium hydroxide (NaOH) to control the pH. Because NaOH is expensive, we sought to minimize the cost of our process by substituting hydrated lime and saccharate of lime (lime sucrate) in its place. The yield of glucooligosaccharides using either 5 % lime (41.4 ± 0.5 g/100 g) or 5 % lime sucrate (40.0 ± 1.4 g/100 g) were both similar to the NaOH control (42.4 ± 1.5 g/100 g). Based on this, it appears that the cost associated with pH control in our process can be reduced by a factor of approximately 2.4 using lime instead of NaOH. Because our chromatographic stage is based on a Ca-form resin to separate glucooligosaccharides, the use of lime not only negates the need for costly de-salting via ion-exchange (elimination of two ion-exchange sections) prior to separation, but also greatly reduces the resin regeneration cost. [ABSTRACT FROM AUTHOR]

The gene encoding sucrose phosphorylase ( 742sp) in Leuconostoc mesenteroides NRRL B-742 was cloned and expressed in Escherichia coli. The nucleotide sequence of the transformed 742sp comprised an ORF of 1,458 bp giving a protein with calculated molecular mass of 55.3 kDa. 742SPase contains a C-terminal amino acid sequence that is significantly different from those of other Leu. mesenteroides SPases. The purified 742SPase had a specific activity of 1.8 U/mg with a K m of 3 mM with sucrose as a substrate; optimum activity was at 37°C and pH 6.7. The purified 742SPase transferred the glucosyl moiety of sucrose to cytosine monophosphate (CMP). [ABSTRACT FROM AUTHOR]

Two arbutin glucosides were synthesized via the acceptor reaction of a glucansucrase from Leuconostoc mesenteroides B-1299CB with arbutin and sucrose. The glucosides were purified by Bio-gel P-2 column chromatography and high-performance liquid chromatography, and the structures were elucidated as 4-hydroxyphenyl β-isomaltoside (arbutin-G1), 4-hydroxyphenyl β-isomaltotrioside (arbutin-G2), according to the results of 1H, 13C, heteronuclear single-quantum coherence, 1H-1H COSY, and heteronuclear multiple-bond correlation analyses. Arbutin glucoside (4-hydroxyphenyl β-isomaltoside) exhibited slower effects on 1,1-diphenyl-2-picrylhydrazyl radical scavenging and similar effects on tyrosinase inhibition, and increased inhibitory effect on matrix metalloproteinase-1 production induced by UVB than arbutin. [ABSTRACT FROM AUTHOR]

Dextransucrase (FMCMDS) from Leuconostoc mesenteroides B-512FMCM, a dextransucrase constitutive and hyper-producing strain, catalyzes the synthesis of dextran from sucrose. The coding region for fmcmds was isolated and sequenced. It consisted of an open reading frame (ORF) of 4699 bp, coding for a 1527 amino acid protein with a molecular mass of 170 kDa. However, it showed a dextransucrase activity band at 180 kDa in SDS-PAGE. Only one nucleotide changed in the promoter site and two amino acid residues were changed in the structural gene from that of the parent L. mesenteroides NRRL B-512F dsrS; an inducible dextransucrase gene of low productivity. [ABSTRACT FROM AUTHOR]

Abstract: In this study, two quercetin-α-d-glucopyranosides were synthesized via the acceptor reaction of a glucansucrase obtained from Leuconostoc mesenteroides B-1299CB, with quercetin and sucrose. The two transfer products were purified via HPLC, and the structures of the products were identified as quercetin-4′-O-α-d-glucopyranoside (Q-G1) and quercetin-3′-O-α-d-glucopyranoside (Q-G1′), in accordance with the results of 1H, 13C, HSQC, H-H COSY, HMBC analyses. The primary product (Q-G1) evidenced slower effects on DPPH radical-scavenging activity (SC50 =25.2μM) than was seen with quercetin (SC50 =6.5μM). The water solubility of Q-G1 was 12.7mM, whereas the quercetin was barely soluble in water. The K i value of Q-G1 (674.5μM) was almost identical to that of quercetin (673.3μM) with regard to tyrosinase inhibition effects. [Copyright &y& Elsevier]

Abstract: A method is presented for synthesizing thermo-, acid-stable oligosaccharides (TASO) from sucrose (2.5–4M) using a dextransucrase prepared from Leuconostoc mesenteroides B-512FMCM. The degree of polymerization (DP) of oligosaccharides synthesized was from 2 to 11. TASO resisted hydrolysis of its glycosidic linkages at 140°C and pH 6.0 for 1h. It was stable at pH''s ranging from 2 to 4 at 120°C. These oligosaccharides effectively inhibited the formation of insoluble glucan, the growth and acid production of Streptococcus sobrinus. However, it stimulated the growth of probiotic organisms such as Bifidobaterium sp. TASO potentially can be used as sweeteners for the food and beverages where thermo- and acid-stable properties are required and as potential inhibitors of dental caries. [Copyright &y& Elsevier]

Abstract: Glucansucrases from Leuconostoc mesenteroides catalyze the transfer of glucosyl units from sucrose to other carbohydrates by acceptor reaction. We modified salicyl alcohol, phenol and salicin by using various glucansucrases and with sucrose as a donor of glucosyl residues. Salicin, phenyl glucose, isosalicin, isomaltosyl salicyl alcohol, and a homologous series of oligosaccharides, connected to the acceptors and differing from one another by one or more glucose residues, were produced as major reaction products. By using salicin and salicyl alcohol as acceptors, B-1355C2 and B-1299CB-BF563 dextransucrases synthesized most widely diverse products, producing more than 12 and 9 different kinds of saccharides, respectively. With phenol, two acceptor products and oligosaccharides were synthesized by using the B-1299CB-BF563 dextransucrase. Salicyl derivatives, as acceptor products, showed higher anti-coagulation activity compared with that of salicin or salicyl alcohol that were used as acceptors. [Copyright &y& Elsevier]

To develop a new transfer product of sucrose, sucrose was modified to maltosyl-sucrose using the transglycosylation activity of maltogenic amylase from Bacillus stearothermophilus (BSMA). The transglycosylation reaction was conducted with maltotriose and sucrose as the donor and acceptor, respectively. The presence of various sucrose transfer products was confirmed by thin layer chromatography (TLC) and high performance anion exchange chromatography (HPAEC). The sucrose transfer products were isolated by alkali-degradation followed by charcoal column chromatography using 20% (v/v) ethanol, then purified by ion exchange and Biogel P-2 gel permeation chromatographies. The structures of the major transfer products were determined to be 6G-α-maltosyl-sucrose (maltosyl-sucrose 1) and 6F-α-maltosyl-sucrose (maltosyl-sucrose 2) by LC-MS and 13C NMR. The mixture of maltosyl-sucrose 1 and 2 showed low sweetness, high hygroscopicity, low Maillard reactivity, and high acid and heat stability. Furthermore, it had an inhibitory effect on mutansucrase and water-insoluble glucan formation. These results indicated that the mixture of maltosyl-sucrose 1 and 2 is a suitable sugar substitute useful for various food products. [Copyright &y& Elsevier]