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Review of sialic acid's biochemistry, sources, extraction and functions with special reference to edible bird's nest

Ling AJW, Chang LS, Babji AS, Latip J, Koketsu M, Lim SJ

Food Chem, 2022 Jan 15;367:130755.
PMID: 34390910 DOI: 10.1016/j.foodchem.2021.130755

Sialic acids are a group of nine-carbon α-keto acids. Sialic acid exists in more than 50 forms, with the natural types discovered as N-acetylneuraminic acid (Neu5Ac), deaminoneuraminic acid (2-keto-3-deoxy-nonulononic acid or Kdn), and N-glycolylneuraminic acid (Neu5Gc). Sialic acid level varies depending on the source, where edible bird's nest (EBN), predominantly Neu5Ac, is among the major sources of sialic acid. Due to its high nutritive value and complexity, sialic acid has been studied extensively through acid, aqueous, and enzymatic extraction. Although detection by chromatographic methods or mass spectrometry is common, the isolation and recovery work remained limited. Sialic acid is well-recognised for its bioactivities, including brain and cognition development, immune-enhancing, anti-hypertensive, anticancer, and skin whitening properties. Therefore, sialic acid can be used as a functional ingredient in the various industries. This paper reviews the current trend in the biochemistry, sources, extraction, and functions of sialic acids with special reference to EBN.

Matched MeSH terms: N-Acetylneuraminic Acid*
Docking of sialic acid analogues against influenza A hemagglutinin: a correlational study between experimentally measured and computationally estimated affinities

Al-qattan MN, Mordi MN

J Mol Model, 2010 May;16(5):1047-58.
PMID: 19911202 DOI: 10.1007/s00894-009-0618-7

A molecular docking tool of AutoDock3.05 was evaluated for its ability to reproduce experimentally determined affinities of various sialic acid analogues toward hemagglutinin of influenza A virus. With the exception of those with a C6-modified glycerol side chain, the experimental binding affinities of most sialic acid analogues (C2, C4 and C5-substituted) determined by viral hemadsorption inhibition assay, hemagglutination inhibition assay and nuclear magnetic resonance correlated well with the computationally estimated free energy of binding. Sialic acid analogues with modified glycerol side chains showed only poor correlation between the experimentally determined hemagglutinin inhibitor affinities and AutoDock3.05 scores, suggesting high mobility of the glutamic acid side chain at the glycerol binding pocket, which is difficult to simulate using a flexi-rigid molecular docking approach. In conclusion, except for some glycerol-substituted sialic acid analogues, the results showed the effectiveness of AutoDock3.05 searching and scoring functions in estimating affinities of sialic acid analogues toward influenza A hemagglutinin, making it a reliable tool for screening a database of virtually designed sialic acid analogues for hemagglutinin inhibitors.

Matched MeSH terms: N-Acetylneuraminic Acid/metabolism*
Fulltext Evaluation of serum sialic acid, fucose levels and their ratio in oral squamous cell carcinoma

Chinnannavar SN, Ashok L, Vidya KC, Setty SM, Narasimha GE, Garg R

J Int Soc Prev Community Dent, 2015 Nov-Dec;5(6):446-50.
PMID: 26759796 DOI: 10.4103/2231-0762.169211

Detection of cancer at the early stage is of utmost importance to decrease the morbidity and mortality of the disease. Apart from the conventional biopsy, minimally invasive methods like serum evaluation are used for screening large populations. Thus, this study aimed to estimate serum levels of sialic acid and fucose and their ratio in oral cancer patients and in healthy control group to evaluate their role in diagnosis.

Matched MeSH terms: N-Acetylneuraminic Acid
The interaction of selective plant lectins with neuraminidase-treated and untreated IgA1 from the sera of IgA nephropathy patients

Hashim OH, Shuib AS, Chua CT

Immunol Invest, 2001 Feb;30(1):21-31.
PMID: 11419909

A study on the binding interaction of lectins from Artocarpus heterophyllus (jacalin), Glycine max and Sambucus nigra with standardised quantity of IgA from the IgA nephropathy patients and normal controls was performed. The Glycine max lectin demonstrated higher affinity towards the serum IgA of IgAN patients as compared to normal controls. However, the affinity binding was lower in cases ofjacalin and the Sambucus nigra lectin. When serum samples were treated with neuraminidase, the differential jacalin affinity binding between IgA1 of patients and normal controls was abrogated. Our data are in support of the view that the O-linked oligosaccharide moieties of the patients IgA1 were generally lacking in galactose and sialic acid residues.

Matched MeSH terms: N-Acetylneuraminic Acid/immunology; N-Acetylneuraminic Acid/chemistry
Site-directed fragment-based generation of virtual sialic acid databases against influenza A hemagglutinin

Al-qattan MN, Mordi MN

J Mol Model, 2010 May;16(5):975-91.
PMID: 19856192 DOI: 10.1007/s00894-009-0606-y

In this study fragment-based drug design is combined with molecular docking simulation technique, to design databases of virtual sialic acid (SA) analogues with new substitutions at C2, C5 and C6 positions of SA scaffold. Using spaces occupied by C2, C5 and C6 natural moieties of SA when bound to hemagglutinin (HA) crystallographic structure, new fragments that are commercially available were docked independently in all the pockets. The oriented fragments were then connected to the SA scaffold with or without incorporation of linker molecules. The completed analogues were docked to the whole SA binding site to estimate their binding conformations and affinities, generating three databases of HA-bound SA analogues. Selected new analogues showed higher estimated affinities than the natural SA when tested against H3N2, H5N1 and H1N1 subtypes of influenza A. An improvement in the binding energies indicates that fragment-based drug design when combined with molecular docking simulation is capable to produce virtual analogues that can become lead compound candidates for anti-flu drug discovery program.

Matched MeSH terms: N-Acetylneuraminic Acid/metabolism*
Fulltext Hemagglutinin protein of Asian strains of human influenza virus A H1N1 binds to sialic acid--a major component of human airway receptors

Chua KH, Chai HC

Genet. Mol. Res., 2012;11(1):636-43.
PMID: 22535399 DOI: 10.4238/2012.March.16.1

Hemagglutinin (HA) protein plays an important role in binding the influenza virus to infected cells and therefore mediates infection. Deposited HA sequences of 86 Asian strains of influenza A (H1N1) viruses during the first outbreak were obtained from the NCBI database and compared. Interaction of the HA protein of influenza A (H1N1) virus with the human sialic acid receptor was also studied using bioinformatics. Overall, not more than three single-point amino acid variants/changes were observed in the HA protein region of influenza A (H1N1) virus from Asian countries when a selected group sequence comparison was made. The bioinformatics study showed that the HA protein of influenza A (H1N1) binds to the sialic acid receptor in human airway receptors, possibly key to air-borne infection in humans.

Matched MeSH terms: N-Acetylneuraminic Acid/metabolism*; N-Acetylneuraminic Acid/chemistry
Neuraminidase treatment abrogates the binding abnormality of IgA1 from IgA nephropathy patients and the differential charge distribution of its alpha-heavy chains

Hashim OH, Shuib AS, Chua CT

Nephron, 2001 Dec;89(4):422-5.
PMID: 11721160

We have studied the interaction of the Gal-GalNAc-reactive champedak lectin-C with neuraminidase-treated and untreated IgA1 from IgA nephropathy patients. The binding ability of the lectin to untreated IgA1 from IgA nephropathy patients was significantly lower as compared to the untreated IgA1 from normal controls. This differential lectin-binding capacity was abrogated when the experiment was performed on neuraminidase-treated sera. Treatment of the serum IgA1 with neuraminidase also abrogated the differential charge distribution between the alpha-heavy chains of IgA nephropathy patients and normal controls.

Matched MeSH terms: N-Acetylneuraminic Acid/immunology; N-Acetylneuraminic Acid/metabolism
Fulltext Preliminary study of the nutritional content of Malaysian edible bird’s nest

Norhayati, M.K., Azman, O., Wan Nazaimoon, W.M.

Malays J Nutr, 2010;16(3):389-396.
MyJurnal

Malaysian edible bird’s nests (EBN) are from the swiflet species, Aerodromus fuciphagus. The objective of this study was to determine and compare the nutrient composition of EBN obtained from different parts of Peninsular Malaysia, collected at three different harvesting seasons, to four commercial brands. A total of 18 raw, unprocessed EBN samples from the North, South and East Coast zones of Peninsular Malaysia and duplicate samples of 4 commercial brands (processed) of EBN samples were analysed. The protein and mineral contents of unprocessed EBN samples between zones and harvesting seasons were comparable. Mean (± SEM) protein content of unprocessed EBN was 61.5 ± 0.6 g/100g and the top four minerals detected were calcium, sodium, magnesium and potassium with mean (± SEM) concentration of 553.1 ± 19.5 mg/100g, 187.9 ± 10.4 mg/100g, 92.9 ± 2.0 mg/100g and 6.3 ± 0.4 mg/100g respectively. Sialic acid content ranged between 0.7 to 1.5%, and remained comparable between samples from different zones and harvesting seasons. The commercial brands were found to contain higher amounts of calcium, sodium, magnesium, potassium and phosphorus compared to unprocessed EBN, warranting further investigation and verification with more samples. Since the nutrient contents of EBN may be affected by seasonal variations and even breeding sites, it is recommended that a more comprehensive study be conducted involving more samples and breeding sites as such data are important to ensure sustainability of the EBN industry in this country.

Matched MeSH terms: N-Acetylneuraminic Acid
Characterization of edible bird's nest of different production, species and geographical origins using nutritional composition, physicochemical properties and antioxidant activities

Quek MC, Chin NL, Yusof YA, Law CL, Tan SW

Food Res Int, 2018 07;109:35-43.
PMID: 29803459 DOI: 10.1016/j.foodres.2018.03.078

Edible bird's nest (EBN) is a precious food made from the solidified saliva of swiftlets. EBN from three types of origin, namely production, swiftlet species and geographical were characterised based on its nutritional composition, physicochemical properties and antioxidant properties. Proximate composition, total phenolic content (TPC) and antioxidant activities were determined following official methods, while mineral and heavy metal contents were obtained by respective atomic adsorption spectrometry (AAS) and inductively coupled plasma-mass spectrometry (ICP-MS). Amino acids profile and sialic acid were determined using high performance liquid chromatography (HPLC). Calcium and sodium were the major elements in EBN samples at averages of 17,267 mg/kg and 13,681 mg/kg, respectively. Despite protein contents were not significantly different; interestingly the total amino acids in A. fuciphagus EBN, 64.57 g/100 g was found to be 23% higher than in A. maximus EBN. EBN from house, A. fuciphagus and Peninsular Malaysia had greater antioxidant activities, 2.33-3.49 mg AAE/g and higher sialic acid, 13.57 g/100 g while those from cave, A. maximus and East Malaysia contained more minerals like calcium and magnesium. The 1, 1-diphenyl-2-picrylhydrazyl (DPPH) free radical scavenging activity and ferric ion reducing antioxidant power (FRAP) of house, A. fuciphagus and Peninsular Malaysia EBNs were approximately 2 times greater than the others. All samples were complied with the Malaysian Standard MS 2334:2011, except for mercury and nitrite. The overall findings suggest that the quality of EBN was varied following the production, species and geographical origins.

Matched MeSH terms: N-Acetylneuraminic Acid
Fulltext High fat diet-induced inflammation and oxidative stress are attenuated by N-acetylneuraminic acid in rats

Yida Z, Imam MU, Ismail M, Ismail N, Ideris A, Abdullah MA

J Biomed Sci, 2015;22:96.
PMID: 26498218 DOI: 10.1186/s12929-015-0211-6

Serum sialic acid levels are positively correlated with coronary artery disease and inflammation. Although sialic acid is a non-specific marker, it is considered sensitive likely due to its influence in sialylation of glycoprotein structures all over the body.

Matched MeSH terms: N-Acetylneuraminic Acid/pharmacology*
Fulltext Edible Bird's Nest Supplementation Improves Male Reproductive Parameters of Sprague Dawley Rat

Jaffar FHF, Osman K, Hui CK, Zulkefli AF, Ibrahim SF

Front Pharmacol, 2021;12:631402.
PMID: 33986667 DOI: 10.3389/fphar.2021.631402

Edible bird's nest (EBN) is reported to have a positive in vitro proliferative effect and contain male reproductive hormones. Spermatogonia cells proliferate during spermatogenesis under male reproductive hormones stimulation that include testosterone, follicle-stimulating hormone (FSH), and luteinizing hormone (LH). Characterization of EBN through liquid chromatography-mass spectrometry (LCMS) has found testosterone as a base peak. Six types of amino acids, estradiol and sialic acid were among the major peaks that have been characterized. Based on the presence of these reproductive components, this study evaluated different doses of EBN on sperm parameters and male reproductive hormones of Sprague Dawley rats. Sixteen Sprague Dawley rats at the age of eight weeks were randomly and equally divided into four groups, which are Control, 10 mg/kg BW/d 50 mg/kg BW/d, and 250 mg/kg BW/d EBN group. The rats were fed with EBN enriched pellet daily and water ad-libitum. Rats were sacrificed and the organ was weighed for organ coefficients after eight weeks of treatment. Sperm concentration, percentage of sperm motility, and sperm viability were evaluated. Meanwhile, ELISA method was used to measure testosterone, FSH, and LH. Findings showed that there were no significant differences in organ coefficient between groups. Supplementation of 250 mg/kg BW/d EBN demonstrated a significant increase in sperm concentration, percentage of sperm motility as well as FSH and LH level compared to 10 mg/kg BW/d group. There was a dose-dependent increase in testosterone level but was not significant between groups. Based on these findings, EBN is concluded to have crucial effects on male reproductive parameters.

Matched MeSH terms: N-Acetylneuraminic Acid
Fulltext Edible Bird's Nest Protects Against Hyperglycemia-Induced Oxidative Stress and Endothelial Dysfunction

Murugan DD, Md Zain Z, Choy KW, Zamakshshari NH, Choong MJ, Lim YM, et al.

Front Pharmacol, 2019;10:1624.
PMID: 32116666 DOI: 10.3389/fphar.2019.01624

Increased oxidative stress by hyperglycemia is a major cause of vascular complications in diabetes. Bird's nest, which is made from the saliva of swiftlets has both medicinal and nutritional values dated back to ancient China. However, its role in improving endothelial dysfunction due to diabetes is yet to be elucidated. The present study examined the protective effect and mechanism of action of the aqueous extract of hydrolyzed edible bird nest (HBN) on endothelium in models of diabetes, in vitro and in vivo. Male db/m+ and db/db mice were orally administered with or without HBN and glibenclamide for 28 days, followed by vascular reactivity studies in mouse aortas. Human umbilical vein endothelial cells (HUVECs) and isolated mouse aorta from C57BL/6J were treated with high glucose (HG), HBN, sialic acid (SA), glibenclamide, and apocynin, respectively. The effects of HBN on reactive oxygen species (ROS) production and nitric oxide (NO) bioavailability were assessed by Western blot, 2',7'-dichlorofluorescin-diacetate (DCF-DA), and 4-amino-5-methylamino-2',7' difluorofluorescein (DAF-FM DA) in HUVECs, isolated mouse aorta, and db/db diabetic mice. HBN significantly reversed the endothelial dysfunction in diabetic mice and isolated mouse aorta. HBN normalized ROS over-production of NOX2 and nitrotyrosine, reversed the reduction of anti-oxidant marker, SOD-1 as well as restored NO bioavailability in both HUVECs challenged with HG and in db/db diabetic mice. Similarly, HG-induced elevation of oxidative stress in HUVECs were reversed by SA, glibenclamide, and apocynin. This attests that HBN restores endothelial function and protects endothelial cells against oxidative damage induced by HG in HUVECs, isolated mouse aorta, and db/db diabetic mice via modulating ROS mechanism, which subsequently increases NO bioavailability. This result demonstrates the potential role of HBN in preserving endothelial function and management of micro- or macrovascular complications in diabetes.

Matched MeSH terms: N-Acetylneuraminic Acid
Fulltext Effect of Edible Bird's Nest Extract on Lipopolysaccharide-Induced Impairment of Learning and Memory in Wistar Rats

Careena S, Sani D, Tan SN, Lim CW, Hassan S, Norhafizah M, et al.

Evid Based Complement Alternat Med, 2018;2018:9318789.
PMID: 30186358 DOI: 10.1155/2018/9318789

Cognitive disability is a common feature associated with a variety of neurological conditions including Alzheimer's Disease (AD), Parkinson's Disease (PD), brain injury, and stroke. Emerging evidence has demonstrated that neuroinflammation plays an important role in the development of cognitive impairment. Current available therapies are relatively ineffective in treating or preventing cognitive disabilities, thus representing an important, unfulfilled medical need. Hence, developing potential treatment is one of the major areas of research interest. Edible bird's nests (EBN) are nests formed by swiftlet's saliva containing sialic acid, which is believed to improve brain function. This present study was embarked upon to evaluate the learning and memory enhancing potential effect of EBN by using Morris water maze test in a Wistar rat model of LPS-induced neuroinflammation. LPS elicited cognitive impairment in the rats by significantly increasing the escape latency while decreasing the number of entries in the probe trial, which are coupled with increased production of proinflammatory cytokines (TNF-α, IL-1β, and IL-6) and oxidative markers (ROS and TBARS) in the hippocampus. Treatment with EBN (125 mg/kg, 250 mg/kg, and 500 mg/kg; p.o.) effectively reversed the effect of LPS on escape latency and probe trial and, in addition, inhibited the LPS-induced upregulation of proinflammatory cytokines and oxidative markers. These findings are suggestive that there is existence of neuroprotective effect contained inside the edible bird's nest.

Matched MeSH terms: N-Acetylneuraminic Acid
Ethnic differences in correlates of microalbuminuria in NIDDM. The role of the acute-phase response

Islam N, Kazmi F, Chusney GD, Mattock MB, Zaini A, Pickup JC

Diabetes Care, 1998 Mar;21(3):385-8.
PMID: 9540020

OBJECTIVE: To investigate whether microalbuminuria is associated with markers of the acute-phase response in NIDDM and whether there are ethnic differences in this association among the three main racial groups in Malaysia.
RESEARCH DESIGN AND METHODS: NIDDM patients of Chinese, Indian, and Malay origin attending a diabetic clinic in Kuala Lumpur, Malaysia, were matched for age, sex, diabetes duration, and glycemic control (n = 34 in each group). Urinary albumin-to-creatinine ratio was measured in an early morning urine sample. Biochemical measurements included markers of the acute-phase response: serum sialic acid, triglyceride, and (lowered) HDL cholesterol.
RESULTS: The frequency of microalbuminuria did not differ among the Chinese, Indian, and Malay patients (44, 41, and 47%, respectively). In Chinese patients, those with microalbuminuria had evidence of an augmented acute-phase response, with higher serum sialic acid and triglyceride and lower HDL cholesterol levels; and urinary albumin-to-creatinine ratio was correlated with serum sialic acid and triglyceride. The acute-phase response markers were not different in Indians, with microalbuminuria being high in even the normoalbuminuric Indians; only the mean arterial blood pressure was correlated with urinary albumin-to-creatinine ratio in the Indians. Malay NIDDM subjects had an association of microalbuminuria with acute-phase markers, but this was weaker than in the Chinese subjects.
CONCLUSIONS: Microalbuminuria is associated with an acute-phase response in Chinese NIDDM patients in Malaysia, as previously found in Caucasian NIDDM subjects. Elevated urinary albumin excretion has different correlates in other racial groups, such as those originating from the Indian subcontinent. The acute-phase response may have an etiological role in microalbuminuria.

Matched MeSH terms: N-Acetylneuraminic Acid/blood

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