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Food-grade algae modified Schiff base-chitosan benzaldehyde composite for cationic methyl violet 2B dye removal: RSM statistical parametric optimization

Agha HM, Abdulhameed AS, Jawad AH, Sidik NJ, Aazmi S, Wilson LD, et al.

Int J Phytoremediation, 2024;26(4):459-471.
PMID: 37583281 DOI: 10.1080/15226514.2023.2246596

This work aims to apply the use of food-grade algae (FGA) composited with chitosan-benzaldehyde Schiff base biopolymer (CHA-BD) as a new adsorbent (CHA-BA/FGA) for methyl violet 2B (MV 2B) dye removal from aqueous solutions. The effect of three processing variables, including CHA-BA/FGA dosage (0.02-0.1 g/100 mL), pH solution (4-10), and contact duration (10-120 min) on the removal of MV 2B was investigated using the Box-Behnken design (BBD) model. Kinetic and equilibrium dye adsorption profiles reveal that the uptake of MV 2B dye by CHA-BA/FGA is described by the pseudo-second kinetics and the Langmuir models. The thermodynamics of the adsorption process (ΔG°, ΔH°, and ΔS°) reveal spontaneous and favorable adsorption parameters of MV 2B dye onto the CHA-BA/FGA biocomposite at ambient conditions. The CHA-BA/FGA exhibited the maximum ability to absorb MV 2B of 126.51 mg/g (operating conditions: CHA-BA/FGA dose = 0.09 g/100 mL, solution pH = 8.68, and temperature = 25 °C). Various interactions, including H-bonding, electrostatic forces, π-π stacking, and n-π stacking provide an account of the hypothesized mechanism of MV 2B adsorption onto the surface of CHA-BA/FGA. This research reveals that CHA-BA/FGA with its unique biocomposite structure and favorable adsorption properties can be used to remove harmful cationic dyes from wastewater.

Matched MeSH terms: Benzaldehydes
Fulltext Membrane-associated glucose-methanol-choline oxidoreductase family enzymes PhcC and PhcD are essential for enantioselective catabolism of dehydrodiconiferyl alcohol

Takahashi K, Hirose Y, Kamimura N, Hishiyama S, Hara H, Araki T, et al.

Appl Environ Microbiol, 2015 Dec;81(23):8022-36.
PMID: 26362985 DOI: 10.1128/AEM.02391-15

Sphingobium sp. strain SYK-6 is able to degrade various lignin-derived biaryls, including a phenylcoumaran-type compound, dehydrodiconiferyl alcohol (DCA). In SYK-6 cells, the alcohol group of the B-ring side chain of DCA is initially oxidized to the carboxyl group to generate 3-(2-(4-hydroxy-3-methoxyphenyl)-3-(hydroxymethyl)-7-methoxy-2,3-dihydrobenzofuran-5-yl) acrylic acid (DCA-C). Next, the alcohol group of the A-ring side chain of DCA-C is oxidized to the carboxyl group, and then the resulting metabolite is catabolized through vanillin and 5-formylferulate. In this study, the genes involved in the conversion of DCA-C were identified and characterized. The DCA-C oxidation activities in SYK-6 were enhanced in the presence of flavin adenine dinucleotide and an artificial electron acceptor and were induced ca. 1.6-fold when the cells were grown with DCA. Based on these observations, SLG_09480 (phcC) and SLG_09500 (phcD), encoding glucose-methanol-choline oxidoreductase family proteins, were presumed to encode DCA-C oxidases. Analyses of phcC and phcD mutants indicated that PhcC and PhcD are essential for the conversion of (+)-DCA-C and (-)-DCA-C, respectively. When phcC and phcD were expressed in SYK-6 and Escherichia coli, the gene products were mainly observed in their membrane fractions. The membrane fractions of E. coli that expressed phcC and phcD catalyzed the specific conversion of DCA-C into the corresponding carboxyl derivatives. In the oxidation of DCA-C, PhcC and PhcD effectively utilized ubiquinone derivatives as electron acceptors. Furthermore, the transcription of a putative cytochrome c gene was significantly induced in SYK-6 grown with DCA. The DCA-C oxidation catalyzed by membrane-associated PhcC and PhcD appears to be coupled to the respiratory chain.

Matched MeSH terms: Benzaldehydes
Apoptosis and cell cycle arrest of human colorectal cancer cell line HT-29 induced by vanillin

Ho K, Yazan LS, Ismail N, Ismail M

Cancer Epidemiol, 2009 Aug;33(2):155-60.
PMID: 19679064 DOI: 10.1016/j.canep.2009.06.003

Vanillin is responsible for the flavor and smell of vanilla, a widely used flavoring agent. Previous studies showed that vanillin could enhance the repair of mutations and thus function as an anti-mutagen. However, its role in cancer, a disease that is closely related to mutation has not yet been fully elucidated.

Matched MeSH terms: Benzaldehydes/pharmacology*
Fulltext Vanillin differentially affects azoxymethane-injected rat colon carcinogenesis and gene expression

Ho KL, Chong PP, Yazan LS, Ismail M

J Med Food, 2012 Dec;15(12):1096-102.
PMID: 23216109 DOI: 10.1089/jmf.2012.2245

Vanillin is the substance responsible for the flavor and smell of vanilla, a widely used flavoring agent. Previous studies reported that vanillin is a good antimutagen and anticarcinogen. However, there are also some contradicting findings showing that vanillin was a comutagen and cocarcinogen. This study investigated whether vanillin is an anticarcinogen or a cocarcinogen in rats induced with azoxymethane (AOM). Rats induced with AOM will develop aberrant crypt foci (ACF). AOM-challenged rats were treated with vanillin orally and intraperitoneally at low and high concentrations and ACF density, multiplicity, and distribution were observed. The gene expression of 14 colorectal cancer-related genes was also studied. Results showed that vanillin consumed orally had no effect on ACF. However, high concentrations (300 mg/kg body weight) of vanillin administered through intraperitoneal injection could increase ACF density and ACF multiplicity. ACF were mainly found in the distal colon rather than in the mid-section and proximal colon. The expression of colorectal cancer biomarkers, protooncogenes, recombinational repair, mismatch repair, and cell cycle arrest, and tumor suppressor gene expression were also affected by vanillin. Vanillin was not cocarcinogenic when consumed orally. However, it was cocarcinogenic when being administered intraperitoneally at high concentration. Hence, the use of vanillin in food should be safe but might have cocarcinogenic potential when it is used in high concentration for therapeutic purposes.

Matched MeSH terms: Benzaldehydes/pharmacology*
Fulltext Pharmacophore modelling of vanillin derivatives, favipiravir, chloroquine, hydroxychloroquine, monolaurin and tetrodotoxin as MPro inhibitors of severe acute respiratory syndrome coronavirus-2 (SARS-CoV-2)

Law WY, Asaruddin MR, Bhawani SA, Mohamad S

BMC Res Notes, 2020 Nov 11;13(1):527.
PMID: 33176880 DOI: 10.1186/s13104-020-05379-6

OBJECTIVES: The aim of this study was to use Ligand-based pharmacophore modelling approach for four established antiviral drugs, namely remdesivir, lopinavir, ritonavir and hydroxychloroquine for COVID-19 inhibitors as training sets. In this study Twenty vanillin derivatives together with monolaurin and tetrodotoxin were used as test sets to evaluate as potential SARS-CoV-2 inhibitors. The Structure-based pharmacophore modelling approach was also performed using 5RE6, 5REX and 5RFZ in order to analyse the binding site and ligand-protein complex interactions.
RESULTS: The pharmacophore modelling mode of 5RE6 displayed two Hydrogen Bond Acceptors (HBA) and one Hydrophobic (HY) interaction. Besides, the pharmacophore model of 5REX showed two HBA and two HY interactions. Finally, the pharmacophore model of 5RFZ showed three HBA and one HY interaction. Based on ligand-based approach, 20 Schiff-based vanillin derivatives, showed strong MPro inhibition activity. This was due to their good alignment and common features to PDB-5RE6. Similarly, monolaurin and tetrodotoxin displayed some significant activity against SARS-CoV-2. From structure-based approach, vanillin derivatives (1) to (12) displayed some potent MPro inhibition against SARS-CoV-2. Favipiravir, chloroquine and hydroxychloroquine also showed some significant MPro inhibition.

Matched MeSH terms: Benzaldehydes/chemistry
Schiff base-nickel, palladium, and platinum complexes derived from N-cyclohexyl hydrazine carbothioamide and 3-hydroxy-4-methoxybenzaldehyde: Selective antiproliferative and proapoptotic effects against colorectal carcinoma

Arafath MA, Al-Suede FSR, Adam F, Al-Juaid S, Khadeer Ahamed MB, Majid AMSA

Drug Dev Res, 2019 09;80(6):778-790.
PMID: 31215682 DOI: 10.1002/ddr.21559

The bidentate N-cyclohexyl-2-(3-hydroxy-4-methoxybenzylidene)hydrazine-1-carbothioamide Schiff base ligand (HL) was coordinated to divalent nickel, palladium and platinum ions to form square planar complexes. The nickel and palladium complexes, [NiL2 ], [PdL2 ] form square planar complexes with 2:1 ligand to metal ratio. The platinum complex, [PtL(dmso)Cl] formed a square planar complex with 1:1 ligand to metal ratio. Platinum undergoes in situ reaction with DMSO before complexing with the ligand in solution. The cytotoxicity of HL, [NiL2 ], [PdL2 ], and [PtL(dmso)Cl] were evaluated against human colon cancer cell line (HCT-116), human cervical cancer (Hela) cell line, melanoma (B16F10) cells, and human normal endothelial cell lines (Eahy926) by MTT assay. The [NiL2 ] complex displayed selective cytotoxic effect against the HCT 116 cancer cell line with IC50 of 7.9 ± 0.2 μM. However, HL, [PdL2 ], and [PtL(dmso)Cl] only exhibited moderate cytotoxic activity with IC50 = 75.9 ± 2.4, 100.0 ± 1.8, and 101.0 ± 3.6 μM, respectively. The potent cytotoxicity of [NiL2 ] was characterized using Hoechst and Rhodamine assays. The nickel complex, [NiL2 ], caused remarkable nuclear condensation and reduction in mitochondrial membrane potential. In addition, molecular docking studies confirms that [NiL2 ] possesses significant binding efficiency with Tyrosine kinase. Altogether, the results revealed that [NiL2 ] exhibits cytotoxicity against the cancer cells via Tyrosine kinase-induced proapoptosis pathway. This study demonstrates that the [NiL2 ] complex could be a promising therapeutic agent against colorectal carcinoma.

Matched MeSH terms: Benzaldehydes/chemistry
Fulltext Synthesis, characterization and biological evaluation of transition metal complexes derived from N, S bidentate ligands

Md Yusof EN, S A Ravoof TB, Tiekink ER, Veerakumarasivam A, Crouse KA, Mohamed Tahir MI, et al.

Int J Mol Sci, 2015 May 15;16(5):11034-54.
PMID: 25988384 DOI: 10.3390/ijms160511034

Two bidentate NS ligands were synthesized by the condensation reaction of S-2-methylbenzyldithiocarbazate (S2MBDTC) with 2-methoxybenzaldehyde (2MB) and 3-methoxybenzaldehyde (3MB). The ligands were reacted separately with acetates of Cu(II), Ni(II) and Zn(II) yielding 1:2 (metal:ligand) complexes. The metal complexes formed were expected to have a general formula of [M(NS)2] where M = Cu2+, Ni2+, and Zn2+. These compounds were characterized by elemental analysis, molar conductivity, magnetic susceptibility and various spectroscopic techniques. The magnetic susceptibility measurements and spectral results supported the predicted coordination geometry in which the Schiff bases behaved as bidentate NS donor ligands coordinating via the azomethine nitrogen and thiolate sulfur. The molecular structures of the isomeric S2M2MBH (1) and S2M3MBH (2) were established by X-ray crystallography to have very similar l-shaped structures. The Schiff bases and their metal complexes were evaluated for their biological activities against estrogen receptor-positive (MCF-7) and estrogen receptor-negative (MDA-MB-231) breast cancer cell lines. Only the Cu(II) complexes showed marked cytotoxicity against the cancer cell lines. Both Schiff bases and other metal complexes were found to be inactive. In concordance with the cytotoxicity studies, the DNA binding studies indicated that Cu(II) complexes have a strong DNA binding affinity.

Matched MeSH terms: Benzaldehydes/chemistry
Fulltext Conjugation of benzylvanillin and benzimidazole structure improves DNA binding with enhanced antileukemic properties

Al-Mudaris ZA, Majid AS, Ji D, Al-Mudarris BA, Chen SH, Liang PH, et al.

PLoS One, 2013;8(11):e80983.
PMID: 24260527 DOI: 10.1371/journal.pone.0080983

Benzyl-o-vanillin and benzimidazole nucleus serve as important pharmacophore in drug discovery. The benzyl vanillin (2-(benzyloxy)-3-methoxybenzaldehyde) compound shows anti-proliferative activity in HL60 leukemia cancer cells and can effect cell cycle progression at G2/M phase. Its apoptosis activity was due to disruption of mitochondrial functioning. In this study, we have studied a series of compounds consisting of benzyl vanillin and benzimidazole structures. We hypothesize that by fusing these two structures we can produce compounds that have better anticancer activity with improved specificity particularly towards the leukemia cell line. Here we explored the anticancer activity of three compounds namely 2-(2-benzyloxy-3-methoxyphenyl)-1H-benzimidazole, 2MP, N-1-(2-benzyloxy-3-methoxybenzyl)-2-(2-benzyloxy-3-methoxyphenyl)-1H-benzimidazole, 2XP, and (R) and (S)-1-(2-benzyloxy-3-methoxyphenyl)-2, 2, 2-trichloroethyl benzenesulfonate, 3BS and compared their activity to 2-benzyloxy-3-methoxybenzaldehyde, (Bn1), the parent compound. 2XP and 3BS induces cell death of U937 leukemic cell line through DNA fragmentation that lead to the intrinsic caspase 9 activation. DNA binding study primarily by the equilibrium binding titration assay followed by the Viscosity study reveal the DNA binding through groove region with intrinsic binding constant 7.39 µM/bp and 6.86 µM/bp for 3BS and 2XP respectively. 2XP and 3BS showed strong DNA binding activity by the UV titration method with the computational drug modeling showed that both 2XP and 3BS failed to form any electrostatic linkages except via hydrophobic interaction through the minor groove region of the nucleic acid. The benzylvanillin alone (Bn1) has weak anticancer activity even after it was combined with the benzimidazole (2MP), but after addition of another benzylvanillin structure (2XP), stronger activity was observed. Also, the combination of benzylvanillin with benzenesulfonate (3BS) significantly improved the anticancer activity of Bn1. The present study provides a new insight of benzyl vanillin derivatives as potential anti-leukemic agent.

Matched MeSH terms: Benzaldehydes/chemistry*
Enhanced Catalytic Activity, Facile Synthesis and Characterization Studies of Spinel Mn-Co Aluminate Nano-Catalysts

Bhavani P, Manikandan A, Jaganathan SK, Shankar S, Antony SA

J Nanosci Nanotechnol, 2018 Feb 01;18(2):1388-1395.
PMID: 29448597 DOI: 10.1166/jnn.2018.14112

Undoped and Mn2+ doped CoAl2O4 (MnxCo1-xAl2O4; x = 0.0 to 1.0) spinel nanoparticles were successfully synthesized by a microwave heating method using glycine as the fuel. X-ray powder diffraction (XRD) was confirmed the cubic spinel structure. The average crystallite size of the samples was found to be in the range of 16.46 nm to 20.25 nm calculated by Scherrer's formula. The nano-sized particle-like morphology of the samples was confirmed by high resolution scanning electron microscopy (HR-SEM) and transmission electron microscopy (HR-TEM) analysis. Energy dispersive X-ray (EDX) results showed the pure form of spinel aluminate structure. The band gap energy (Eg) of pure CoAl2O4 was estimated to be 3.68 eV from UV-Visible diffuse reflectance spectroscopy (DRS), and the Eg values increased with increase of Mn2+ ions, due to the smaller grain size. The magnetic hysteresis (M-H) loop showed the superparamagnetic nature, and the magnetization and coercivity values increased with increasing Mn2+ ions, which was confirmed by vibrating sample magnetometer (VSM). All compositions of the nano-catalysts were tested as catalyst successfully for the conversion of benzyl alcohol into benzaldehyde and observed good catalytic activity.

Matched MeSH terms: Benzaldehydes
Novel Synthesis and Characterization Studies of Spinel Ni x Co1-xAl₂O₄ (x= 0.0 to 1.0) Nano-Catalysts for the Catalytic Oxidation of Benzyl Alcohol

Suguna S, Shankar S, Jaganathan SK, Manikandan A

J Nanosci Nanotechnol, 2018 Feb 01;18(2):1019-1026.
PMID: 29448527 DOI: 10.1166/jnn.2018.13960

Ni-doped cobalt aluminate NixCo1-xAl2O4 (x = 0.0, 0.2, 0.4, 0.6, 0.8 and 1.0) spinel nanoparticles were successfully synthesized by a simple microwave combustion method using urea as the fuel and as well as reducing agent. X-ray powder diffraction (XRD) was confirmed the formation of single phase, cubic spinel cobalt-nickel aluminate structure without any other impurities. Average crystallite sizes of the samples were found to be in the range of 18.93 nm to 21.47 nm by Scherrer's formula. Fourier transform infrared (FT-IR) spectral analysis was confirmed the corresponding functional groups of the M-O, Al-O and M-Al-O (M = Co and Ni) bonds of spinel NixCo1-xAl2O4 structure. Scanning electron microscope (SEM) and transmission electron microscope (TEM) images was confirmed the particle like nanostructured morphology. Energy band gap (Eg) value was calculated using UV-Visible diffuse reflectance spectra (DRS) and the Eg values increased with increasing Ni2+ dopant from x = 0.2 (3.58 eV) to x = 1.0 (4.15 eV). Vibrating sample magnetometer (VSM) measurements exposed that undoped and Ni-doped CoAl2O4 samples have superparamagnetic behavior and the magnetization (Ms) values were increased with increasing Ni2+ ions. Spinel NixCo1-xAl2O4 samples has been used for the catalytic oxidation of benzyl alcohol into benzaldehyde and was found that the sample Ni0.6Co0.4Al2O4 showed higher conversion 94.37% with 100% selectivity than other samples, which may be due to the smaller particle size and higher surface area.

Matched MeSH terms: Benzaldehydes
Morphological and transcript changes in the biosynthesis of lignin in oil palm (Elaeis guineensis) during Ganoderma boninense infections in vitro

Goh KM, Dickinson M, Supramaniam CV

Physiol Plant, 2018 Mar;162(3):274-289.
PMID: 28940509 DOI: 10.1111/ppl.12645

Lignification of the plant cell wall could serve as the first line of defense against pathogen attack, but the molecular mechanisms of virulence and disease between oil palm and Ganoderma boninense are poorly understood. This study presents the biochemical, histochemical, enzymology and gene expression evidences of enhanced lignin biosynthesis in young oil palm as a response to G. boninense (GBLS strain). Comparative studies with control (T1), wounded (T2) and infected (T3) oil palm plantlets showed significant accumulation of total lignin content and monolignol derivatives (syringaldehyde and vanillin). These derivatives were deposited on the epidermal cell wall of infected plants. Moreover, substantial differences were detected in the activities of enzyme and relative expressions of genes encoding phenylalanine ammonia lyase (EC 4.3.1.24), cinnamate 4-hydroxylase (EC 1.14.13.11), caffeic acid O-methyltransferase (EC 2.1.1.68) and cinnamyl alcohol dehydrogenase (CAD, EC 1.1.1.195). These enzymes are key intermediates dedicated to the biosynthesis of lignin monomers, the guaicyl (G), syringyl (S) and ρ-hydroxyphenyl (H) subunits. Results confirmed an early, biphasic and transient positive induction of all gene intermediates, except for CAD enzyme activities. These differences were visualized by anatomical and metabolic changes in the profile of lignin in the oil palm plantlets such as low G lignin, indicating a potential mechanism for enhanced susceptibility toward G. boninense infection.

Matched MeSH terms: Benzaldehydes/metabolism

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