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As stingless bee honey (SBH) is gaining in popularity in the Malaysian market, it is now prone to adulteration. The higher price of SBH compared to floral honey has led to the use of unusual adulterants such as vinegar and even floral honey to mimic the unique taste and appearance of SBH. Since the current AOAC 998.12 method fails to detect these adulterants as their δ

Edible bird's nests (EBNs) are the nests of swiftlets, made from the saliva of the male swiftlet (Aerodramus fuciphagus). Due to their nutritional value, EBNs are recognized as a premium food and highly in demand among the Chinese community. EBNs are commonly adulterated with cheaper ingredients and efforts are being made to combat these activities using different analytical techniques. In this study, nuclear magnetic resonance (1H-NMR) metabolomic fingerprinting combined with chemometrics, particularly principal component analysis (PCA) and orthogonal partial least square-discriminant analysis (OPLS-DA), was employed to detect adulteration in EBNs. Authentic EBN samples from different locations in Malaysia were used and adulteration was simulated using nutrient agar, collagen, gelatine, karaya gum and melamine at 1, 5 and 10% w/w, respectively. Overall, unsupervised PCA was able to distinguish authentic EBNs from those adulterated with nutrient agar, collagen and gelatine down to 5% w/w adulteration level. As for EBN adulterated with karaya gum and melamine, a distinct peak can be observed at 1.91 ppm and 6.10 ppm, respectively. The supervised OPLS-DA predictive model was able to differentiate authentic EBNs from simulated adulterated EBNs with 100% accuracy. Conclusively, 1H-NMR metabolomics combined with chemometrics could be a potential tool for the detection of adulteration in EBN.

As stingless bee honey (SBH) is gaining in popularity in the Malaysian market, it is now prone to adulteration. The higher price of SBH compared to floral honey has led to the use of unusual adulterants such as vinegar and even floral honey to mimic the unique taste and appearance of SBH. Since the current AOAC 998.12 method fails to detect these adulterants as their δ13C values are in the range for C3 plants, untargeted 1H NMR metabolomics was proposed. Principal component analysis of SBH 1H NMR fingerprints was able to distinguish authentic SBHs from adulterated ones down to 1% adulteration level for selected adulterants. Discriminant analysis showed promising results in distinguishing the preliminary datasets of authentic SBHs from the adulterated ones, including discriminating SBHs adulterated with different adulterants derived from C3 and C4 plants. Hence, to assure any emerging adulterant can be detected, all 1H NMR regions should be considered.

The antimicrobial activities of eleven maleimide derivatives were tested in this study. Out of the eleven samples, N-(4fluorophenyl) maleimide, N-(4-chlorophenyl) maleimide and N-(4-bromophenyl) maleimide were synthesized by reacting maleic anhydride with 4-fluorophenylaniline, 4-chlorophenylaniline and 4-bromophenylaniline, respectively in the presence of acetic acid, by refluxing overnight. Crystals were successfully obtained after the products were recrystallized with different mixture of solvents. Their chemical structures were confirmed by infrared spectroscopy (IR), H and C Nuclear Magnetic Resonance (NMR) and melting point determination. Subsequently, all the samples were screened for their biological activity using disc diffusion method. The bacteria chosen for this study were Gram-negative Escherichia coli, Gram-positive Bacillus subtilis and yeast Saccharomyces cerevisae. Positive control for bacteria was streptomycin and nystatin for the yeast. M1 to M6 compounds gave remarkable result at low concentrations whereas M8, M9 and M11 compounds are mostly inactive up to a high concentration. In contrast, the unsubstituted maleimide, M7 was highly reactive towards both bacteria and yeast at low and high concentrations.

Thioureas play an important role in medicinal chemistry and agricultures due to their biological activity such as antibacterial, antifungal, antiviral, herbicides, rodenticides, phenoloxidase enzymatic inhibitors, anti-HIV and anti-tumor agents. In this study, five substituted bis-thioureas have been synthesized. The isophataloyl chloride and 2,6pyridinedicarbonyl dichloride were easily converted to bis-isothiocyanate compound via the reaction with ammonium thiocyanate by solid–liquid phase transfer catalysis of polyethylene glycol-400 (PEG-400). Bis-isothiocyanate compound was reacted with aniline derivatives to produce substituted bis-thioureas in good yield at room temperature. All the novel compounds were obtained as yellow solid after recrystallization using DMF/EtOH/H2O. Their c h e m i c a l structures were confirmed by Infrared spectrosopy (IR), Nuclear Magnetic Resonance (NMR) H and C and mass spectrometry. The five synthesized compounds were screened for antimicrobial activities using disc diffusion method for antimicrobial activity against Gram-positive bacteria (Bacillus Subtilis and Staphylococcus Aureus), Gram-negative bacteria (Escherichia Coli and Salmonella Typhi) and a mold (Aspergillus Niger). All tested compounds showed low antimicrobial activity since the diameter of inhibition zone (IZ) measure was less than positive control inhibition zone.

Synthesis of imine compounds usually results in moderate yield due its reversibility characteristic and prone to hydrolysis. Hence, to increase the formation of imine compound, self-replicating catalyst was introduced. The self-replicating catalyst is the imine product itself. The first imine compound, 4-{[4-(3,5-Dimethyl-phenylcarbamoyl)-benzylidene]-amino}-phenyl)-acetic acid has been synthesized from 4-Amino-N-(3,5-dimethyl-phenyl)-benzamide and (4-formyl-phenyl)-acetic acid. Simultaneously, 4-formylbenzoic acid was reacted with thionyl chloride to produce 4-formylbenzoyl chloride, which was then reacted with 2-amino-4,6-dimethylpyridine in the presence of triethylamine to afford N-(4,6-dimethyl-pyridin-2-yl)-4-formyl-benzamide. N-(4,6-dimethyl-pyridin-2-yl)-4-formyl-benzamide formed then reacted with 4-amino-2-methylbenzoic acid to form the second imine derivative, 4-{[4-(4,6-dimethyl-pyridin-2-ylcarbamoyl)-benzylidene]-amino}-2-methyl-benzoic acid. The concentration time profile for the synthesis of self-replicating imine 1 reveals the classic sigmoidal shape characteristics of an autocatalytic process and the rate of the reaction are higher than that observed in the absence of recognition. In order to demonstrate the nature of self-replicating catalyst, a preformed imine 1 was doped into the reaction mixture of amine 1 and the corresponding aldehyde, 4-formylbenzoic acid. The insertion of substoichiometric amounts (15 mol%) of imine 1 at the start of the reaction has accelerated the rate formation of imine 1.