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Eight kinds of phenolic acid conjugated chitooligosaccharides (COSs) were synthesized using hydroxyl benzoic acid and hydroxyl cinnamic acid. These phenolic acid conjugated-COSs with different substitution groups, including p-hydroxyl, 3,4-dihydroxyl, 3-methoxyl-4-hydroxyl and 3,5-dimethoxyl-4-hydroxy groups, were evaluated for their inhibitory act...
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... inhibition pattern of CFA-COS was analysed by Lineweaver-Burk with and without CFA-COS. The inhibi- tion kinetics analysed by Lineweaver-Burk plots indicate that CFA-COS acts as non-competitive inhibitor, which means that CFA-COS can bind either another regulatory site or to the subsite of β-secretase (Figure 3). Moreover, K i value of CFA-COS estimated to be 419.13 ...
Citations
... Their inhibitory role against ACE activity, even at the case of Aβ25-35-induced ACE activity, have been noticed [12]. Chitosan oligosaccharide conjugated with caffeic acid have been found effective in inhibiting the activity of β-site amyloid precursor protein-cleaving enzyme (BACE), the regulatory enzyme of amyloid beta (Aβ) synthesis [13][14]. AD pathogenesis is aggravated through Aβ fibrillization [1,10]. ...
As the number of aged people is increasing globally, so is the case of neurodegenerative disease Alzheimer’s disease (AD). Though different treatment strategy have been applied against AD, success rate is meager. Thus, search for natural compounds capable of withstanding AD progression has received momentum. Present article evaluates the potentiality of chitin and chitosan, the natural bio-polymers, in ameliorating AD. Information presented here would be of immense importance to the AD patients, patients’ care givers, health care providers, researchers and policy makers round the world.
... Chitooligosaccharide (COS), the degradation product of chitosan, has aroused an increasing interest due to its excellent biological properties and potential applications. Of particular importance are its admirable biological activities including anti-microbial (Fernandes et al., 2008), anti-fungal (Mei et al., 2015), anti-oxidant (Ma et al., 2020), anti-inflammatory (Kunanusornchai et al., 2016), anti-obesity (Huang et al., 2015), anti-tumor (Suzuki et al., 1986;Zhao et al., 2019), anti-hypertensive (Huang et al., 2005), anti-HIV-1 (Artan et al., 2010), anti-Alzheimer's (Eom et al., 2013), and immune-enhancing effects (Zhang et al., 2014). It also shows promise as a drug/DNA delivery agent (Kumari et al., 2018;Li et al., 2019a;Wang et al., 2020). ...
Chitosanase is a significant chitosan-degrading enzyme involved in industrial applications, which forms chitooligosaccharides (COS) as reaction products that are known to have various biological activities. In this study, the gene csnS was cloned from a deep-sea bacterium Serratia sp. QD07, as well as over-expressed in Escherichia coli, which is a new chitosanase encoding gene. The recombinant strain was cultured in a 5 L fermenter, which yielded 324 U/mL chitosanases. After purification, CsnS is a cold-adapted enzyme with the highest activity at 60°C, showing 37.5% of the maximal activity at 0°C and 42.6% of the maximal activity at 10°C. It exhibited optimum activity at pH 5.8 and was stable at a pH range of 3.4–8.8. Additionally, CsnS exhibited an endo-type cleavage pattern and hydrolyzed chitosan polymers to yield disaccharides and trisaccharides as the primary reaction products. These results make CsnS a potential candidate for the industrial manufacture of COS.
... Antioxidant, antimicrobial, antifungal, and anti-inflammatory properties of p-coumaric acid and its derivatives were investigated [111]. Eom et al. [112] conjugated p-coumaric acid, among other phenolics, onto chitooligosaccharides (COS-s) via carbodiimide coupling (DDC, HOBt) and performed β-secretase (BACE) assay. The phenolic acid conjugated COS-s possessed elevated BACE inhibitory activity compared to native COS. ...
In this era, there is a global concern in the use of bioactive molecules such as chitosan in the field of antimicrobial and antioxidant benefits. Because of its biodegradability, biological compatibility, antimicrobial, antioxidants activity, and high safety, chitosan could be used in a large number of applications. It could exist in many forms, such as fibers, gels, films, sponges, nanoparticles, and beads. The different biological activities of chitosan and its products are extensively investigated to broaden the application fields in several areas. Chitosan's natural properties depend strongly on water and other solvent solubility. Consequently, the chitosan oligosaccharides with a low polymerization degree are getting significant attention in the pharmaceutical and medical applications because they have lower viscosity and higher water solubility than chitosan. The objective of this review article is to put the antioxidant and antimicrobial properties of chitosan and its derivatives under the spotlight. The impacts of chitosan on physicochemical parameters like molecular weight and deacetylation degree on its bioactivities are also identified. Additionally, other applications of chitosan and its derivatives, including wound healing products, wastewater treatment, and cosmetics, have also been highlighted.
... The characterization of synthesized conjugates was performed by UV, FTIR, and 1 H NMR data. Caffeic acid conjugated COS and protocatechuic acid conjugated COS have shown a comparatively higher reducing power and radical scavenging (NO and DPPH) activity as compared to COS and other derivatives (Eom et al., 2013). Therefore, caffeic acid conjugated COS can be utilized as an antioxidant compound, that was synthesized by using hydroxyl cinnamic acid and hydroxyl benzoic acid for conjugation with COS. ...
... BACE plays a critical role in reducing the levels of Aβ amyloid peptide in Alzheimer's disease (AD). The results showed that caffeic acid conjugated COS derivative has significantly inhibited the BACE and reduced the risk of AD (Eom et al., 2013). Therefore, engineering of COS and GlcNAc derivatives can significantly improve their biological activities. ...
Chitooligosaccharides (COS) and N-acetyl glucosamine (GlcNAc) are currently of enormous relevance to pharmaceutical, nutraceutical, cosmetics, food, and agriculture industries due to their wide range of biological activities, which include antimicrobial, antitumor, antioxidant, anticoagulant, wound healing, immunoregulatory, and hypocholesterolemic effects. A range of methods have been developed for the synthesis of COS with a specific degree of polymerization along with high production titres. In this respect, chemical, enzymatic, and microbial means, along with modern genetic manipulation techniques, have been extensively explored; however no method has been able to competently produce defined COS and GlcNAc in a mono-system approach. Henceforth, the chitin research has turned toward increased exploration of chemoenzymatic processes for COS and GlcNAc generation. Recent developments in the area of green chemicals, mainly ionic liquids, proved vital for the specified COS and GlcNAc synthesis with better yield and purity. Moreover, engineering of COS and GlcNAc to generate novel derivatives viz. carboxylated, sulfated, phenolic acid conjugated, amino derived COS, etc., further improved their biological activities. Consequently, chemoenzymatic synthesis and engineering of COS and GlcNAc emerged as a useful approach to lead the biologically-active compound-based biomedical research to an advanced prospect in the forthcoming era.
... Chitooligosaccharides possesses the anti-inflammatory activity effect by inhibiting the secretion of certain anti-inflammatory cytokines like TNF-α, IL-2, IL-4, IL-6 in the LPS-stimulated inflammation. Chitosan oligomers helps in promoting phagocytosis process augmenting the immune response [58][59][60]. ...
... In recent years chitooligosaccharides have attracted a lot of interest as a useful agent as a bone-strengthener in osteoporosis [71]. Also the chitooligosaccharides can act as anti-malaria agent and also effective in controlling the glucose level in serum [58]. ...
Chitinase, also known as chitinolytic enzymes, is a group of enzymes that can hydrolyze insoluble chitin, a long-chain polymer of N-acetyl glucosamine. Chitinases are actively present in different organisms such as bacteria, fungi, crustaceans, insects, invertebrates, etc. Chitinases from Streptomyces origin received considerable attention because of the wide range of industrial and biotechnological applications specifically: (i) protection against fungal pathogens, (ii) can be used as an effective biocontrol agent, (iii) protoplast isolation, (iv) chitinase as a mosquitocidal and nematocidal agent, (v) treatment of chitinous waste. Chitooligomers, such as N-acetylglucosamine and chitooligosaccharides produced by the chitinolytic activity of chitinase have been of interest in recent years due to their potential applications in medical, agricultural, and industrial applications. Microbial chitinases are more attractive and contribute for large-scale production to satisfy the demands. Fermentation technology plays a crucial role not only in the large-scale production of enzymes but also reduces the cost of production. In the recent years there is a constant increase in demand for chitooligosaccharides resulted from chitin degradation by chitinase enzyme.
Hence this chapter will mainly focus on diversity, biotechnological application and sustainable bioproduction of chitinases enzyme from Streptomyces origin, their properties, its production and potential applications in industrial and biotechnological sphere.
... There is also a notable decline in cholinergic neurotransmissions as a result of overexpression of acetylcholine esterase (AChE) related to AD etiology [162]. Substantial alternative in vitro studies revealed that COS with MW 3-5 kDa and DD ∼90%, can inhibit β-secretase at IC-50 of 25 μM to 42 μM [163], while aminoethyl-COS and phenolic acid-conjugated COS have higher inhibitory effects on β-secretase at IC50 of 85 μg/mL and 191 μg/mL respectively [101,164], compared to the unmodified COS. It was further revealed that COS can suppress the neurotic processes involved in AD pathogenesis such as oxidative stress-induced neuron apoptosis and glial cell-mediated inflammatory responses. ...
Being the most versatile biopolymer, chitooligosaccharide/chitosan oligosaccharide (COS) has been extensively studied for a range of exceptional biological activities and potential developments of novel medical devices and systems in biomedical and pharmaceutical fields. While possessing intrinsic biocompatibility, mucoadhesive-ness, and non-toxicity it gained more interests in the biomedical development of novel systems, devices, and pharmaceutical formulations. The bioactive relativity of chitosan and COS are of highly significant and thus explored in this paper while highlighting its multiple biological activities and promising biomedical applications. More emphasis is on the molecular weight, degree of acetylation/deacetylation, degree of polymerization and reactive groups in relation to chitin and chitosan. Despite COS wide acceptance and utilization, the associated viscosity and instability are crucial factors that posed a great challenge to researchers. The apparent reason attributed to instability and viscosity could be the presence intrinsic variable oligomers within COS. Due to lack of data on safety and impurity analysis of thermal exposure of COS, we hypothesized that different molecules could be generated with thermal treatment of COS, thus finally suggested a prospective determination of thermal degradation product(s)in COS. Hence the aim of this paper is to highlight COS physicochemical and biological significance with reference to its recent developments and propose a further chemical analysis thermal treated COS. This could trigger future researchers for possible isolation and characterization of distinct biomolecules from COS.
... There is also a notable decline in cholinergic neurotransmissions as a result of overexpression of acetylcholine esterase (AChE) related to AD etiology [189]. Substantial alternative in vitro studies revealed that COS with MW 3-5 kDa and DD 90%, can inhibit β-secretase at IC-50 of 25 μM to 42 μM [57], while aminoethyl-COS and phenolic acid-conjugated COS have higher inhibitory effects on β-secretase at IC50 of 85 μg/ml and 191 μg/ml respectively [190,191], compared to the unmodified COS. It was further revealed that COS could suppress the neurotic processes involved in AD pathogenesis such as oxidative stress-induced neuron apoptosis and glial cell-mediated inflammatory responses. ...
The frequently studied polysaccharide, chitosan oligosaccharide/chitooligosaccharide (COS) is the major degradation product of chitosan/chitin via chemical hydrolysis or enzymatic degradation involving deacetylation and depolymerization processes. Innumerable studies have revealed in the recent decade that COS has various promising biomedical implications in the past analysis, current developments and potential applications in a biomedical, pharmaceutical and agricultural sector. Innovations into COS derivatization has broadened its application in cosmeceutical and nutraceutical productions as well as in water treatment and environmental safety. In relation to its parent biomaterials and other available polysaccharides, COS has low molecular weight (Mw), higher degree of deacetylation (DD), higher degree of polymerization (DP), less viscous and complete water solubility, which endowed it with significant biological properties like antimicrobial, antioxidant, anti-inflammatory and antihypertensive, as well as drug/DNA delivery ability. In addition, it is also revealed to exhibit antidiabetic, anti-obesity, anti-HIV-1, anti-Alzheimer's disease, hypocholesterolemic, calcium absorption and hemostatic effects. Furthermore, COS is shown to have higher cellular transduction and completely absorbable via intestinal epithelium due to its cationic sphere exposed on the more exposed shorter N-glucosamine (N-Glc) units. This paper narrates on the recent developments in COS biomedical applications while paying considerable attention to its physicochemical properties and its chemical composition. Its pharmacokinetic aspects are also briefly discussed while highlighting potential overdose or lethal dosing. In addition, due to its multiple NGlc unit composition and vulnerability to degradation, its safety is given significant attention. Finally, a suggestion is made for extensive study on COS anti-HIV effects with well-refined batches.
... There is also a notable decline in cholinergic neurotransmissions as a result of overexpression of acetylcholine esterase (AChE) related to AD etiology [189]. Substantial alternative in vitro studies revealed that COS with MW 3-5 kDa and DD 90%, can inhibit β-secretase at IC-50 of 25 μM to 42 μM [57], while aminoethyl-COS and phenolic acid-conjugated COS have higher inhibitory effects on β-secretase at IC50 of 85 μg/ml and 191 μg/ml respectively [190,191], compared to the unmodified COS. It was further revealed that COS could suppress the neurotic processes involved in AD pathogenesis such as oxidative stress-induced neuron apoptosis and glial cell-mediated inflammatory responses. ...
The frequently studied polysaccharide, chitosan oligosaccharide/chitooligosaccharide (COS) is the major degradation product of chitosan/chitin via chemical hydrolysis or enzymatic degradation involving deacetylation and depolymerization processes. Innumerable studies have revealed in the recent decade that COS has various promising biomedical implications in the past analysis, current developments and potential applications in a bio-medical, pharmaceutical and agricultural sector. Innovations into COS derivatization has broadened its application in cosmeceutical and nutraceutical productions as well as in water treatment and environmental safety. In relation to its parent biomaterials and other available polysaccharides, COS has low molecular weight (Mw), higher degree of deacetylation (DD), higher degree of polymerization (DP), less viscous and complete water sol-ubility, which endowed it with significant biological properties like antimicrobial, antioxidant, anti-inflammatory and antihypertensive, as well as drug/DNA delivery ability. In addition, it is also revealed to exhibit antidiabetic, anti-obesity, anti-HIV-1, anti-Alzheimer's disease, hypocholesterolemic, calcium absorption and hemostatic effects. Furthermore, COS is shown to have higher cellular transduction and completely absorbable via intestinal epithelium due to its cationic sphere exposed on the more exposed shorter N-glucosamine (N-Glc) units. This paper narrates the recent developments in COS biomedical applications while paying considerable attention to its physicochemical properties and its chemical composition. Its pharmacokinetic aspects are also briefly discussed while highlighting potential overdose or lethal dosing. In addition, due to its multiple NGlc unit composition and vulnerability to degradation, its safety is given significant attention. Finally, a suggestion is made for extensive study on COS anti-HIV effects with well-refined batches.
... Resveratrol treatment protected against memory loss and brain pathology in 3xTg-AD mice and induced cognitive enhancement in healthy wild type mice, an observation that might be related to the modulation of BACE1 [33]. Furthermore, the hydroxycinnamic acid, caffeic acid conjugated to chito-oligosaccharides has the potential to be used as BACE 1 inhibitors to reduce the risk of AD [54]. A combination of caffeic acid/caffeic acid phenethyl ester can also restore acrolein-induced BACE 1 changes in HT22 mouse hippocampal cells [37]. ...
Alzheimer’s and Parkinson’s diseases are the most common age-related and predominantly idiopathic neurodegenerative disorders of unknown pathogenesis. Although there are both clinical and neuropathological features of these diseases that are different, they also share some common aetiologies, such as protein aggregation, mitochondrial dysfunction, oxidative stress, and neuroinflammation. Epidemiological, in vitro and in vivo evidences suggest an inverse correlation between wine consumption and the incidence of neurodegenerative disorders. Wine benefits are, in large part, attributable to the intake of specific polyphenols, which mediate cell function under both normal and pathological conditions. In this review, we aim to provide an overview of the role that wine consumption plays in delaying neurodegenerative disorders. We discuss animal and in vitro studies in support of these actions and we consider how their biological mechanisms at the cellular level may underpin their physiological effects. Together, these data indicate that polyphenols present in wine may hold neuroprotective potential in delaying the onset of neurodegenerative disorders.
... Recently, Dai et al. proposed that COS exerted its neuroprotective effect partly through suppressing β-site amyloid precursor protein-cleaving enzyme 1 (BACE1) expression and enzymatic activity [112]. Eom et al. prepared various phenolic acid-conjugated COS like hydroxyl cinnamic acid and hydroxyl benzoic acid to explore their inhibitory effect on BACE, and the results indicated that caffeic acid-conjugated COS was most effective in repressing BACE and ameliorating AD [113]. Jia et al. established an Aβ 1-42 rat model of AD and orally administrated rats with COS of various concentrations for 15 days in order to verify the effect of COS on AD. ...
Chitooligosaccharide (COS), which is acknowledged for possessing multiple functions, is a kind of low-molecular-weight polymer prepared by degrading chitosan via enzymatic, chemical methods, etc. COS has comprehensive applications in various fields including food, agriculture, pharmacy, clinical therapy, and environmental industries. Besides having excellent properties such as biodegradability, biocompatibility, adsorptive abilities and non-toxicity like chitin and chitosan, COS has better solubility. In addition, COS has strong biological functions including anti-inflammatory, antitumor, immunomodulatory, neuroprotective effects, etc. The present paper has summarized the preparation methods, analytical techniques and biological functions to provide an overall understanding of the application of COS.
