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  1. Various polar tripeptides as asymmetric organocatalyst in direct aldol reactions in aqueous media
    Bayat S, Tejo BA, Salleh AB, Abdmalek E, Normi YM, Abdul Rahman MB
    Chirality, 2013 Nov;25(11):726-34.
    PMID: 23966316 DOI: 10.1002/chir.22205
    A series of tripeptide organocatalysts containing a secondary amine group and two amino acids with polar side chain units were developed and evaluated in the direct asymmetric intermolecular aldol reaction of 4-nitrobenzaldehyde and cyclohexanone. The effectiveness of short polar peptides as asymmetric catalysts in aldol reactions to attain high yields of enantio- and diastereoselective isomers were investigated. In a comparison, glutamic acid and histidine produced higher % ee and yields when they were applied as the second amino acid in short trimeric peptides. These short polar peptides were found to be efficient organocatalysts for the asymmetric aldol addition reaction in aqueous media.
    Matched MeSH terms: Aldehydes/chemistry*
  2. Fulltext A comparative analysis of the influence of human salivary enzymes on odorant concentration in three palm wines
    Lasekan O
    Molecules, 2013 Sep 25;18(10):11809-23.
    PMID: 24071987 DOI: 10.3390/molecules181011809
    The influence of human salivary enzymes on palm wines' odorant concentrations were investigated by the application of aroma extracts dilution analysis (AEDA) and by the calculation of odour activity values (OAVs), respectively. The odorants were quantified by means of stable isotope dilution assays (SIDA), and the degradation profiles of odorants by human saliva were also studied. Results revealed 46 odour-active compounds in the flavour dilution (FD) factor range of 4-256, and all were subsequently identified. Of the 46 odorants, 41 were identified in the Elaeis guineensis wine, 36 in Raphia hookeri wine and 29 in Borassus flabellifer wine. Among the odorants, the highest FD-factors were obtained from acetoin, 2-acetyl-1-pyrroline and 3-isobutyl-2-methoxypyrazine. Among the 13 potent odorants identified, five aroma compounds are reported here as important contributors to palm wine aroma, namely 3-isobutyl-2-methoxy-pyrazine, acetoin, 2-acetyl-1-pyrroline, 3-methylbutylacetate and ethyl hexanoate. Meanwhile, salivary enzymic degradation of odorants was more pronounced among the aldehydes, esters and thiols.
    Matched MeSH terms: Aldehydes/chemistry
  3. Fulltext Total synthesis, cytotoxic effects of damnacanthal, nordamnacanthal and related anthraquinone analogues
    Akhtar MN, Zareen S, Yeap SK, Ho WY, Lo KM, Hasan A, et al.
    Molecules, 2013 Aug 20;18(8):10042-55.
    PMID: 23966087 DOI: 10.3390/molecules180810042
    Naturally occurring anthraquinones, damnacanthal (1) and nordamnacanthal (2) were synthesized with modified reaction steps and investigated for their cytotoxicity against the MCF-7 and K-562 cancer cell lines, respectively. Intermediate analogues 2-bromomethyl-1,3-dimethoxyanthraquinone (5, IC50 = 5.70 ± 0.21 and 8.50 ± 1.18 mg/mL), 2-hydroxymethyl-1,3-dimethoxyanthraquinone (6, IC50 = 12.10 ± 0.14 and 14.00 ± 2.13), 2-formyl-1,3-dimethoxyantharquinone (7, IC50 = 13.10 ± 1.02 and 14.80 ± 0.74), 1,3-dimethoxy-2-methylanthraquinone (4, IC50 = 9.40 ± 3.51 and 28.40 ± 2.33), and 1,3-dihydroxy-2-methylanthraquinone (3, IC50 = 25.60 ± 0.42 and 28.40 ± 0.79) also exhibited moderate cytotoxicity against MCF-7 and K-562 cancer cell lines, respectively. Other structurally related compounds like 1,3-dihydroxyanthraquinone (13a, IC50 = 19.70 ± 0.35 and 14.50 ± 1.28), 1,3-dimethoxyanthraquinone (13b, IC50 = 6.50 ± 0.66 and 5.90 ± 0.95) were also showed good cytotoxicity. The target compound damnacanthal (1) was found to be the most cytotoxic against the MCF-7 and K-562 cancer cell lines, with IC50 values of 3.80 ± 0.57 and 5.50 ± 1.26, respectively. The structures of all compounds were elucidated with the help of detailed spectroscopic techniques.
    Matched MeSH terms: Aldehydes/chemistry*
  4. Infrared spectrum, structural and optical properties and molecular docking study of 3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbaldehyde
    Mary YS, Panicker CY, Sapnakumari M, Narayana B, Sarojini BK, Al-Saadi AA, et al.
    Spectrochim Acta A Mol Biomol Spectrosc, 2015 Mar 5;138:529-38.
    PMID: 25528512 DOI: 10.1016/j.saa.2014.11.041
    The optimized molecular structure, vibrational frequencies, corresponding vibrational assignments of 3-(4-fluorophenyl)-5-phenyl-4,5-dihydro-1H-pyrazole-1-carbaldehyde have been investigated experimentally and theoretically. The title compound was optimized using at HF and DFT levels of calculations. The B3LYP/6-311++G(d,p) (5D,7F) results and in agreement with experimental infrared bands. The normal modes are assigned using potential energy distribution. The stability of the molecule arising from hyper-conjugative interaction and charge delocalization has been analyzed using natural bonding orbital analysis. The frontier molecular orbital analysis is used to determine the charge transfer within the molecule. From molecular electrostatic potential map, it is evident that the negative electrostatic potential regions are mainly localized over the carbonyl group and mono substituted phenyl ring and are possible sites for electrophilic attack and, positive regions are localized around all para substituted phenyl and pyrazole ring, indicating possible sites for nucleophilic attack. First hyperpolarizability is calculated in order to find its role in nonlinear optics. The geometrical parameters are in agreement with experimental data. From the molecular docking studies, it is evident that the fluorine atom attached to phenyl ring and the carbonyl group attached to pyrazole ring are crucial for binding and the results draw us to the conclusion that the compound might exhibit phosphodiesterase inhibitory activity.
    Matched MeSH terms: Aldehydes/chemistry*
  5. Fulltext Design, synthesis and antiviral potential of 14-aryl/heteroaryl-14H-dibenzo[a,j]xanthenes using an efficient polymer-supported catalyst
    Reddi Mohan Naidu K, Satheesh Krishna B, Anil Kumar M, Arulselvan P, Ibrahim Khalivulla S, Lasekan O
    Molecules, 2012 Jun 18;17(6):7543-55.
    PMID: 22710828 DOI: 10.3390/molecules17067543
    Polyethyleneglycol bound sulfonic acid (PEG-OSO₃H), a chlorosulphonic acid-modified polyethylene glycol was successfully used as an efficient and eco-friendly polymeric catalyst in the synthesis of 14-aryl/heteroaryl-14H-dibenzo[a,j]xanthenes obtained from the reaction of 2-naphthol and carbonyl compounds under solvent-free conditions with short reaction times and excellent yields. The biological properties of these synthesized title compounds revealed that compounds 3b, 3c, 3f and 3i showed highly significant anti-viral activity against tobacco mosaic virus.
    Matched MeSH terms: Aldehydes/chemistry
  6. A new anthraquinone from Morinda citrifolia roots
    Ee GC, Wen YP, Sukari MA, Go R, Lee HL
    Nat Prod Res, 2009;23(14):1322-9.
    PMID: 19735047 DOI: 10.1080/14786410902753138
    An investigation of Morinda citrifolia roots afforded a new anthraquinone, 2-ethoxy-1-hydroxyanthraquinone (1), along with five other known anthraquinones: 1-hydroxy-2-methylanthraquinone (2), damnacanthal (3), nordamnacanthal (4), 2-formyl-1-hydroxyanthraquinone (5) and morindone-6-methyl-ether (6). This is the first report on the isolation of morindone-6-methyl-ether (6) from this plant. The structures of these compounds were elucidated based on spectroscopic analyses such as NMR, MS and IR. Biological evaluation of five pure compounds and all the extracts against the larvae of Aedes aegypti indicated 1-hydroxy-2-methylanthraquinone (2) and damnacanthal (3) were the extracts to exhibit promising larvicidal activities.
    Matched MeSH terms: Aldehydes/chemistry
  7. Fulltext Characterisation of the Convective Hot-Air Drying and Vacuum Microwave Drying of Cassia alata: Antioxidant Activity, Essential Oil Volatile Composition and Quality Studies
    Chua LYW, Chua BL, Figiel A, Chong CH, Wojdyło A, Szumny A, et al.
    Molecules, 2019 Apr 24;24(8).
    PMID: 31022967 DOI: 10.3390/molecules24081625
    The preservation of active constituents in Cassia alata through the removal of moisture is crucial in producing a final product with high antioxidant activity. This study aims to determine the influences of various drying methods and drying conditions on the antioxidant activity, volatiles and phytosterols content of C. alata. The drying methods used were convective drying (CD) at 40 °C, 50 °C and 60 °C; freeze drying; vacuum microwave drying (VMD) at 6, 9 and 12 W/g; and two-stage convective pre-drying followed by vacuum microwave finish drying (CPD-VMFD) at 50 °C and 9 W/g. The drying kinetics of C. alata are best described by the thin-layer model (modified Page model). The highest antioxidant activity, TPC and volatile concentration were achieved with CD at 40 °C. GC-MS analysis identified the presence of 51 volatiles, which were mostly present in all samples but with quantitative variation. The dominant volatiles in fresh C. alata are 2-hexenal (60.28 mg 100 g-1 db), 1-hexanol (18.70 mg 100 g-1 db) and salicylic acid (15.05 mg 100 g-1 db). The concentration of phytosterols in fresh sample was 3647.48 mg 100 g-1 db, and the major phytosterols present in fresh and dried samples were β-sitosterol (1162.24 mg 100 g-1 db). CPD-VMFD was effective in ensuring the preservation of higher phytosterol content in comparison with CD at 50 °C. The final recommendation of a suitable drying method to dehydrate C. alata leaves is CD at 40 °C.
    Matched MeSH terms: Aldehydes/chemistry
  8. Fulltext Changes in Physicochemical Properties and Volatile Compounds of Roselle (Hibiscus sabdariffa L.) Calyx during Different Drying Methods
    Juhari NH, Martens HJ, Petersen MA
    Molecules, 2021 Oct 16;26(20).
    PMID: 34684840 DOI: 10.3390/molecules26206260
    Fresh roselle are high in moisture and deteriorate easily, which makes drying important for extending shelf-life and increasing availability. This study investigated the influence of different drying methods (oven-drying, freeze-drying, vacuum-drying, and sun-drying) on the quality of roselle calyx expressed as physicochemical properties (moisture content, water activity, soluble solids, color), volatile compounds, and microstructure. Oven-drying and freeze-drying reduced moisture content most while vacuum-drying and sun-drying were not as efficient. All drying methods except sun-drying resulted in water activities low enough to ensure safety and quality. Vacuum-drying had no impact on color of the dry calyx and only small impact on color of water extract of calyx. Drying reduced terpenes, aldehydes, and esters but increased furans. This is expected to reduce fruity, floral, spicy, and green odors and increase caramel-like aroma. Sun-drying produced more ketones, alcohols, and esters. Scanning electron microscopy revealed that freeze-drying preserved the cell structure better, and freeze-dried samples resembled fresh samples most compared to other drying techniques. The study concludes that freeze-drying should be considered as a suitable drying method, especially with respect to preservation of structure.
    Matched MeSH terms: Aldehydes/chemistry
  9. Probing 4-(diethylamino)-salicylaldehyde-based thiosemicarbazones as multi-target directed ligands against cholinesterases, carbonic anhydrases and α-glycosidase enzymes
    Hashmi S, Khan S, Shafiq Z, Taslimi P, Ishaq M, Sadeghian N, et al.
    Bioorg Chem, 2021 02;107:104554.
    PMID: 33383322 DOI: 10.1016/j.bioorg.2020.104554
    With the fading of 'one drug-one target' approach, Multi-Target-Directed Ligands (MTDL) has become a central idea in modern Medicinal Chemistry. The present study aimed to design, develop and characterize a novel series of 4-(Diethylamino)-salicylaldehyde based thiosemicarbazones (3a-p) and evaluates their biological activity against cholinesterase, carbonic anhydrases and α-glycosidase enzymes. The hCA I isoform was inhibited by these novel 4-(diethylamino)-salicylaldehyde-based thiosemicarbazones (3a-p) in low nanomolar levels, the Ki of which differed between 407.73 ± 43.71 and 1104.11 ± 80.66 nM. Against the physiologically dominant isoform hCA II, the novel compounds demonstrated Kis varying from 323.04 ± 56.88 to 991.62 ± 77.26 nM. Also, these novel 4-(diethylamino)-salicylaldehyde based thiosemicarbazones (3a-p) effectively inhibited AChE, with Ki values in the range of 121.74 ± 23.52 to 548.63 ± 73.74 nM. For BChE, Ki values were obtained with in the range of 132.85 ± 12.53 to 618.53 ± 74.23 nM. For α-glycosidase, the most effective Ki values of 3b, 3k, and 3g were with Ki values of 77.85 ± 10.64, 96.15 ± 9.64, and 124.95 ± 11.44 nM, respectively. We have identified inhibition mechanism of 3b, 3g, 3k, and 3n on α-glycosidase AChE, hCA I, hCA II, and BChE enzyme activities. Hydrazine-1-carbothioamide and hydroxybenzylidene moieties of compounds play an important role in the inhibition of AChE, hCA I, and hCA II enzymes. Hydroxybenzylidene moieties are critical for inhibition of both BChE and α-glycosidase enzymes. The findings of in vitro and in silico evaluations indicate 4-(diethylamino)-salicylaldehyde-based thiosemicarbazone scaffold to be a promising hit for drug development for multifactorial diseases like Alzheimer's disease.
    Matched MeSH terms: Aldehydes/chemistry
  10. New One-Pot Synthesis of 1,3,5-Triazines: Three-Component Condensation, Dimroth Rearrangement, and Dehydrogenative Aromatization
    Junaid A, Lim FPL, Tiekink ERT, Dolzhenko AV
    ACS Comb Sci, 2019 07 08;21(7):548-555.
    PMID: 31180634 DOI: 10.1021/acscombsci.9b00079
    A new, effective one-pot synthesis of the 6, N2-diaryl-1,3,5-triazine-2,4-diamines under microwave irradiation was developed. The method involved an initial three-component condensation of cyanoguanidine, aromatic aldehydes, and arylamines in the presence of hydrochloric acid. Without isolation, the resulting 1,6-diaryl-1,6-dihydro-1,3,5-triazine-2,4-diamines were treated with a base to initiate Dimroth rearrangement and spontaneous dehydrogenative aromatization, affording the desired compounds. The developed method was found to be sufficiently general in scope, tolerating various aromatic aldehydes and amines; by using their combinations in the first step, a representative library of 110 compounds was successfully prepared and screened for anticancer properties.
    Matched MeSH terms: Aldehydes/chemistry
  11. Fulltext Subchronic toxicity, immunoregulation and anti-breast tumor effect of Nordamnacantal, an anthraquinone extracted from the stems of Morinda citrifolia L
    Abu N, Zamberi NR, Yeap SK, Nordin N, Mohamad NE, Romli MF, et al.
    BMC Complement Altern Med, 2018 Jan 27;18(1):31.
    PMID: 29374471 DOI: 10.1186/s12906-018-2102-3
    BACKGROUND: Morinda citrifolia L. that was reported with immunomodulating and cytotoxic effects has been traditionally used to treat multiple illnesses including cancer. An anthraquinone derived from fruits of Morinda citrifolia L., nordamnacanthal, is a promising agent possessing several in vitro biological activities. However, the in vivo anti-tumor effects and the safety profile of nordamnacanthal are yet to be evaluated.

    METHODS: In vitro cytotoxicity of nordamnacanthal was tested using MTT, cell cycle and Annexin V/PI assays on human MCF-7 and MDA-MB231 breast cancer cells. Mice were orally fed with nordamnacanthal daily for 28 days for oral subchronic toxicity study. Then, the in vivo anti-tumor effect was evaluated on 4T1 murine cancer cells-challenged mice. Changes of tumor size and immune parameters were evaluated on the untreated and nordamnacanthal treated mice.

    RESULTS: Nordamnacanthal was found to possess cytotoxic effects on MDA-MB231, MCF-7 and 4T1 cells in vitro. Moreover, based on the cell cycle and Annexin V results, nordamnacanthal managed to induce cell death in both MDA-MB231 and MCF-7 cells. Additionally, no mortality, signs of toxicity and changes of serum liver profile were observed in nordamnacanthal treated mice in the subchronic toxicity study. Furthermore, 50 mg/kg body weight of nordamncanthal successfully delayed the progression of 4T1 tumors in Balb/C mice after 28 days of treatment. Treatment with nordamnacanthal was also able to increase tumor immunity as evidenced by the immunophenotyping of the spleen and YAC-1 cytotoxicity assays.

    CONCLUSION: Nordamnacanthal managed to inhibit the growth and induce cell death in MDA-MB231 and MCF-7 cell lines in vitro and cease the tumor progression of 4T1 cells in vivo. Overall, nordamnacanthal holds interesting anti-cancer properties that can be further explored.

    Matched MeSH terms: Aldehydes/chemistry
  12. Biologically active vallesamine, strychnan, and rhazinilam alkaloids from Alstonia: Pneumatophorine, a nor-secovallesamine with unusual incorporation of a 3-ethylpyridine moiety
    Lim JL, Sim KS, Yong KT, Loong BJ, Ting KN, Lim SH, et al.
    Phytochemistry, 2015 Sep;117:317-24.
    PMID: 26125941 DOI: 10.1016/j.phytochem.2015.06.024
    Four alkaloids comprising two vallesamine, one strychnan, and one pyranopyridine alkaloid, in addition to 32 other known alkaloids were isolated from two Malayan Alstonia species, Alstonia pneumatophora and Alstonia rostrata. The structures of these alkaloids were determined using NMR and MS analyses, and in one instance, confirmed by X-ray diffraction analysis. The nor-6,7-secovallesamine alkaloid, pneumatophorine, is notable for an unusual incorporation of a 3-ethylpyridine moiety in a monoterpenoid indole. The rhazinilam-type alkaloids (rhazinicine, nor-rhazinicine, rhazinal, and rhazinilam) showed strong cytotoxicity toward human KB, HCT-116, MDA-MB-231, and MRC-5 cells, while pneumatophorine, the uleine alkaloid undulifoline, and the strychnan alkaloids, N4-demethylalstogustine and echitamidine, induced concentration dependent relaxation in phenylephrine-precontracted rat aortic rings.
    Matched MeSH terms: Aldehydes/chemistry
  13. Synthesis, bioactivity and binding energy calculations of novel 3-ethoxysalicylaldehyde based thiosemicarbazone derivatives
    Ishaq M, Taslimi P, Shafiq Z, Khan S, Ekhteiari Salmas R, Zangeneh MM, et al.
    Bioorg Chem, 2020 07;100:103924.
    PMID: 32442818 DOI: 10.1016/j.bioorg.2020.103924
    In recent decade, the entrance of α-N-heterocyclic thiosemicarbazones derivates (Triapne, COTI-2 and DpC) in clinical trials for cancer and HIV-1 has vastly increased the interests of medicinal chemists towards this class of organic compounds. In the given study, a series of eighteen new (3a-r) 3-ethoxy salicylaldehyde-based thiosemicarbazones (TSC), bearing aryl and cycloalkyl substituents, were synthesized and assayed for their pharmacological potential against carbonic anhydrases (hCA I and hCA II), cholinesterases (AChE and BChE) and α-glycosidase. The hCA I isoform was inhibited by these novel 3-ethoxysalicylaldehyde thiosemicarbazone derivatives (3a-r) in low nanomolar levels, the Ki of which differed between 144.18 ± 26.74 and 454.92 ± 48.32 nM. Against the physiologically dominant isoform hCA II, the novel compounds demonstrated Kis varying from 110.54 ± 14.05 to 444.12 ± 36.08 nM. Also, these novel derivatives (3a-r) effectively inhibited AChE, with Ki values in the range of 385.38 ± 45.03 to 983.04 ± 104.64 nM. For BChE was obtained with Ki values in the range of 400.21 ± 35.68 to 1003.02 ± 154.27 nM. For α-glycosidase the most effective Ki values of 3l, 3n, and 3q were with Ki values of 12.85 ± 1.05, 16.03 ± 2.84, and 19.16 ± 2.66 nM, respectively. Moreover, the synthesized TCSs were simulated using force field methods whereas the binding energies of the selected compounds were estimated using MM-GBSA method. The findings indicate the present novel 3-ethoxy salicylaldehyde-based thiosemicarbazones to be excellent hits for pharmaceutical applications.
    Matched MeSH terms: Aldehydes/chemistry*
  14. Fulltext Composition and Bioactivity of Essential Oil from Citrus grandis (L.) Osbeck 'Mato Peiyu' Leaf
    Tsai ML, Lin CD, Khoo KA, Wang MY, Kuan TK, Lin WC, et al.
    Molecules, 2017 Dec 05;22(12).
    PMID: 29206180 DOI: 10.3390/molecules22122154
    'Mato Peiyu' pomelo (Citrus grandis (L.) Osbeck 'Mato Peiyu') leaves from pruning are currently an agricultural waste. The aim of this study was to isolate essential oils from these leaves through steam distillation (SD) and solvent-free microwave extraction (SFME) and to evaluate their applicability to skin care by analyzing their antimicrobial, antioxidant (diphenyl-1-picrylhydrazyl scavenging assay, β-carotene/linoleic acid assay, and nitric oxide scavenging assay), anti-inflammatory (5-lipoxygenase inhibition assay), and antityrosinase activities. The gas chromatography-mass spectrometry results indicated that the main components of 'Mato Peiyu' leaf essential oils were citronellal and citronellol, with a total percentage of 50.71% and 59.82% for SD and SFME, respectively. The highest bioactivity among all assays was obtained for 5-lipoxygenase inhibition, with an IC50 value of 0.034% (v/v). The MIC90 of the antimicrobial activity of essential oils against Escherichia coli, Pseudomonas aeruginosa, Staphylococcus aureus, and Candida albicans ranged from 0.086% to 0.121% (v/v). Citronellal and citronellol were the main contributors, accounting for at least 54.58% of the essential oil's bioactivity. This paper is the first to report the compositions and bioactivities of 'Mato Peiyu' leaf essential oil, and the results imply that the pomelo leaf essential oil may be applied in skin care.
    Matched MeSH terms: Aldehydes/chemistry
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