Bionic Acids Research Articles

A matrine-based supramolecular ionic salt that enhances the water solubility, transdermal delivery, and bioactivity of salicylic acid

Salicylic acid (H[Sal]) is an attractive bionic acid that is widely used in cosmetics and drugs for the treatment of skin diseases, owing to its excellent anti-acne, anti-inflammatory, antibacterial, oil-control, stratum-corneum-conditioning, and anti-photoaging abilities. However, H[Sal] is a relatively strong irritant and cannot be used on sensitive skin, and its poor water solubility limits the amounts that can be included in formulas, resulting in poor transdermal efficiency and bioavailability. In this study, we develop matrinium salicylate ([Mat][Sal]), a supramolecular ionic salt that is less cytotoxic and irritates the skin less than H[Sal], while exhibiting enhanced water-solubility, transdermal-delivery, and bioactivity properties. The anticancer, antioxidant, anti-inflammatory, and antibacterial properties of [Mat][Sal] are found to be superior or comparable to those of H[Sal]. The molecular structure of [Mat][Sal] is thoroughly investigated, including through single-crystal structure refinement, to gain an in-depth understanding of its properties. Moreover, in-vitro skin penetration experiments show that forming a salt with matrine increase the transdermal efficiency of H[Sal] while not damaging the skin barrier. The transdermal mechanisms of H[Sal] and [Mat][Sal] are studied both experimentally and using molecular dynamics simulations, which show that, compared to H[Sal], [Mat][Sal] reacts more strongly with the skin, and [Sal]− diffuses more rapidly in the skin owing to its higher water solubility and the ion-pair effect. Furthermore, [Mat][Sal] exhibits satisfactory anti-acne capabilities in a clinical-efficacy trial, highlighting its great potential for use in biomedical and cosmetics applications.

The potential of new bionic acids as prebiotics and antimicrobials

A study was made to determine the effect of galactosyl derivatives of hydroxy acids on selected microorganisms with probiotic features and on pathogenic bacteria associated with food, the digestive system and human skin. It was shown that the highest tested concentration (0.05 M) of the gluconic acid and glucoheptonic acid derivatives had a more favorable effect on the development of Lactobacillus bacteria than the corresponding concentration of lactobionic acid. The new bionic acids added to the culture medium at appropriate concentrations (0.05 M or 0.025 M gluconic acid derivative, 0.025 M or 0.0125 M glucoheptonic acid derivative) clearly stimulated the growth of L. brevis strain MG451814.1. The derivatives also supported the formation of biofilm by selected strains of L. acidophilus, L. brevis and L. casei. Antibacterial activity of gluconic and glucoheptonic acid derivatives was observed against selected strains: S. Choleraesuis, S. epidermidis and Staphylococcus aureus. This provides a prospect of limiting the development of antibiotic-resistant strains. It is anticipated that the newly acquired compounds have potential use as ingredients of dietary supplements, pharmaceutical preparations or cosmetics, because of the properties demonstrated as well as their similarity to currently known bionic acids.

Lactobionic Acid as a Potential Food Ingredient: Recent Studies and Applications.

Lactobionic acid (LBA) is a bionic acid naturally found in the "Caspian Sea yogurt" and chemically constituted of a gluconic acid bonded to a galactose. The compound is known for its numerous proven attributes as an antioxidant, chelator, and moisturizer agent. There is a growing interest of the academic community and industry research sectors in the application of LBA as a food ingredient. Thus, this review describes the current methods of LBA production, patents related, general applications and regulations, research statistics, future prospects, and an overview of the challenges faced by the food industry to incorporate the acid in their products. Studies associated to food application and human intake are scarce in the literature. To date, they account for only a small amount of all available research papers and patents on the subject, which is due to LBA prohibitions despite the approval of its salt (calcium lactobionate) and the lack of regulation in most countries. Further studies on the safety of consumption should be carried out in coming years in order to elucidate its toxicological aspects and to extend the technological possibilities of the food processing industry.

Synthesis of the Galactosyl Derivative of Gluconic Acid With the Transglycosylation Activity of β-Galactosidase.

Bionic acids are bioactive compounds demonstrating numerous interesting properties. They are widely produced by chemical or enzymatic oxidation of disaccharides. This paper focuses on the galactosyl derivative of gluconic acid as a result of a new method of bionic acid synthesis which utilises the transglycosylation properties of β-galactosidase and introduces lactose as a substrate. Products obtained in such a process are characterised by different structures (and, potentially, properties) than those resulting from traditional oxidation of disaccharides. The aim of this study is to determine the effect of selected parameters (concentration and ratio of substrates, dose of the enzyme, time, pH, presence of salts) on the course of the reaction carried out with the enzymatic preparation Lactozym, containing β-galactosidase from Kluyveromyces lactis. Research has shown that increased dry matter content in the baseline solution (up to 50%, by mass per volume) and an addition of NaCl contribute to higher yield. On the other hand, reduced content of the derivative is a result of increased pH from 7.0 to 9.0 and an addition of magnesium and manganese salts. Moreover, exceeding the β-galactosidase dose over approx. 35 000 U per 100 g of lactose also leads to reduced yield of the process. The most favourable molar ratio of sodium gluconate to lactose is 2.225:0.675. Depending on the conditions of the synthesis, the product concentration ranged between 17.3 and 118.3 g/L of the reaction mixture, which corresponded to the mass fraction of 6.64-23.7% of dry matter. The data obtained as a result of the present study may be useful for designing an industrial process.

Zymomonas mobilis: a novel platform for future biorefineries.

Biosynthesis of liquid fuels and biomass-based building block chemicals from microorganisms have been regarded as a competitive alternative route to traditional. Zymomonas mobilis possesses a number of desirable characteristics for its special Entner-Doudoroff pathway, which makes it an ideal platform for both metabolic engineering and commercial-scale production of desirable bio-products as the same as Escherichia coli and Saccharomyces cerevisiae based on consideration of future biomass biorefinery. Z. mobilis has been studied extensively on both fundamental and applied level, which will provide a basis for industrial biotechnology in the future. Furthermore, metabolic engineering of Z. mobilis for enhancing bio-ethanol production from biomass resources has been significantly promoted by different methods (i.e. mutagenesis, adaptive laboratory evolution, specific gene knock-out, and metabolic engineering). In addition, the feasibility of representative metabolites, i.e. sorbitol, bionic acid, levan, succinic acid, isobutanol, and isobutanol produced by Z. mobilis and the strategies for strain improvements are also discussed or highlighted in this paper. Moreover, this review will present some guidelines for future developments in the bio-based chemical production using Z. mobilis as a novel industrial platform for future biofineries.

Effects of Cosmetic Formulations Containing Hydroxyacids on Sun-Exposed Skin: Current Applications and Future Developments

This paper describes recent data on the effects of various skin formulations containing hydroxyacids (HAs) and related products on sun-exposed skin. The most frequently used classes of these products, such as α- and β-hydroxyacids, polyhydroxy acids, and bionic acids, are reviewed, and their application in cosmetic formulations is described. Special emphasis is devoted to the safety evaluation of these formulations, particularly on the effects of their prolonged use on sun-exposed skin. We also discuss the important contribution of cosmetic vehicles in these types of studies. Data on the effects of HAs on melanogenesis and tanning are also included. Up-to-date methods and techniques used in those explorations, as well as selected future developments in the cosmetic area, are presented.

Production of lactobionic acid and sorbitol from lactose/fructose substrate using GFOR/ GL enzymes from Zymomonas mobilis cells: A kinetic study

In this work, we have investigated the kinetics of the biotechnological production of lactobionic acid ( LBA) and sorbitol by the catalytic action of glucose–fructose oxidoreductase ( GFOR) and glucono-δ-lactonase ( GL) enzymes. The cells of bacterium Zymomonas mobilis ATCC 29191 containing this enzymatic complex were submitted to permeabilization and reticulation procedures. The effect of the concentration of substrates on the rate of product formation using a mobilized cell system was investigated. The application of higher fructose concentration seems to not affect the initial rate of formation of the bionic acid. Under conditions of low initial concentration of lactose, the experimental kinetic data of the bi-substrate reaction were modelled by assuming a rate equation of the classical ping-pong mechanism. The found kinetic parameters displayed a low affinity of the GFOR enzyme for both substrates. The enzymatic system did not exhibit normal Michaelis–Menten kinetics in response to a change of concentration of lactose, when fructose was held constant, presenting a sigmoid relationship between initial velocity and substrate concentration. A rate equation based on Hill kinetics was used to describe the kinetic behaviour of this enzyme-substituted reaction at higher lactose concentrations. The results from batch experiments using immobilized cells within Ca-alginate beads revealed that there is no pronounced occurrence of mass transfer limitations on LBA production for beads with 1.2 mm in average diameter. This discussion aids for defining the best operating conditions to maximize the productivity for LBA and sorbitol in this bioconversion and also for reducing the complexity of downstream separation processes.

Applications of hydroxy acids: classification, mechanisms, and photoactivity

Hydroxy acids (HAs) represent a class of compounds which have been widely used in a number of cosmetic and therapeutic formulations in order to achieve a variety of beneficial effects for the skin. We review and discuss the most frequently used classes of these compounds, such as α-hydroxy acids, β-hydroxy acids, polyhydroxy acids, and bionic acids, and describe their applications as cosmetic and therapeutic agents. Special emphasis is devoted to the safety evaluation of these formulations, in particular on the effects of their prolonged use on sun-exposed skin. Furthermore, we summarize the very limited number of studies dealing with the modifications evoked by topical application of products containing HAs on photocarcinogenesis. In spite of the large number of reports on the cosmetic and clinical effects of HAs, their biological mechanism(s) of action still require more clarification. Some of these mechanisms are discussed in this article along with important findings on the effect of HAs on melanogenesis and on tanning. We also emphasize the important contribution of cosmetic vehicles in these types of studies. Thus, HAs play an important role in cosmetic formulations, as well as in many dermatologic applications, such as in treating photoaging, acne, ichthyosis, rosacea, pigmentation disorders, and psoriasis.

New biotransformations of some reducing sugars to the corresponding (di)dehydro(glycosyl) aldoses or aldonic acids using fungal pyranose dehydrogenase

The fungal enzyme pyranose dehydrogenase (PDH) (EC 1.1.99.29) purified to apparent homogeneity from culture media of Agaricus meleagris catalyzed the substrate-dependent C-1, C-2, C-3, C-1,3′ or C-2,3(′) (di)oxidation of a number of mono- and disaccharides with 1,4-benzoquinone as an electron acceptor. d-Ribose, d-allose, d-gulose and d-talose were oxidized to the corresponding aldonic acids. l-Arabinose was converted exclusively to 2-dehydro- l-arabinose ( l- erythro-pentos-2-ulose) whereas d-xylose underwent competing C-2 and C-3 oxidation followed by dioxidation to 2,3-didehydro- d-arabinose ( d- glycero-pentos-2,3-diulose). The major final oxidation products of maltose and cellobiose were the novel compounds 2,3′-didehydromaltose and 2,3′-didehydrocellobiose (α- and β- d- ribo-hexos-3-ulopyranosyl-(1 → 4)- d- arabino-hexos-2-ulose), formed via 2- and 3′-monooxidation intermediates. Minor concomitant (di)oxidation at C-1,(3′) to the corresponding bionic acids also took place. Maltotriose was preferentially oxidized at C-3″ of the terminal glucopyranosyl unit and at C-1 of the reducing moiety. The structures of these sugar oxidation products were established by in situ 1D and 2D NMR spectroscopy and ESI–MS. Based on HPLC analysis, conversions of (glycosyl)aldoses in non-buffered systems were nearly quantitative within 3–24 h, depending on the substrate. As the enzyme allows an easy access to highly reactive di- or tricarbonyl sugars, it might become a useful catalyst in carbohydrate chemistry.

A Biochemical Test for Crown Gall Bacteria

Agrobacterium tumefaciens is the agent for crown gall disease of several plants, thus causing serious economic losses in many countries. Except for its phytopathogenic action, it does not display any characteristic physiological or morphological properties. Its final identification is established by experimentally induced tumours, a procedure which often demands too much time for quick intervention in an epidemic. A quick, easy and specific identification test would be very useful. We wish, therefore, to report that Agrobacterium tumefaciens and A. radiobacter produce 3-ketoglycosides from the corresponding disaccharides and bionic acids. We propose a test based on this property, which is very simple, can be carried out in any phytopathological laboratory with ordinary glassware and chemicals, gives a result after 1–2 days and is, so far as we can judge from our present experience, limited to members of the genus Agrobacterium.

The formation and consumption of lactobionic and maltobionic acids by Pseudomonas species.

It has been shown that amongst 19 strains of 16 differentPseudomonas species four formed an appreciable amount of acid on a solid medium containing maltose, whilst six did the same on a solid medium containing lactose. ForPs. calco-acetica it was proved that this species brings about a rapid conversion of lactose into lactobionic acid (yield±85–90%). The same was found to hold forPs. quercitopyrogallica (yield±90 %), which species, moreover, is also able to convert maltose into maltobionic acid (yields varying between 65 and 80%). An investigation of later phases of these cultures showed that the primarily formed bionates slowly disappear. The two species in question are, therefore, able to spring the oxygen bridge between the two constituent parts of the bionic acids, and this makes it very likely that they are neither entirely devoid of the ability to split the disaccharides into the constituent hexoses.