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Fulltext Antibacterial and Antispore Activities of Isolated Compounds from Piper cubeba L

Alqadeeri F, Rukayadi Y, Abbas F, Shaari K

Molecules, 2019 Aug 26;24(17).
PMID: 31454974 DOI: 10.3390/molecules24173095

Piper cubeba L. is the berry of a shrub that is indigenous to Java, Southern Borneo, Sumatra, and other islands in the Indian Ocean. The plant is usually used in folk traditional medicine and is an important ingredient in cooking. The purpose of this study was to isolate and purify the bioactive compounds from P. cubeba L. fractions. In addition, the isolated compounds were tested for their antibacterial and antispore activities against vegetative cells and spores of Bacilluscereus ATCC33019, B. subtilis ATCC6633, B.pumilus ATCC14884, and B.megaterium ATCC14581. The phytochemical investigation of the DCM fraction yielded two known compounds: β-asarone (1), and asaronaldehyde (2) were successfully isolated and identified from the methanol extract and its fractions of P. cubeba L. Results showed that exposing the vegetative cells of Bacillus sp. to isolated compounds resulted in an inhibition zone with a large diameter ranging between 7.21 to 9.61 mm. The range of the minimum inhibitory concentration (MIC) was between 63.0 to 125.0 µg/mL and had minimum bactericidal concentration (MBC) at 250.0 to 500.0 µg/mL against Bacillus sp. Isolated compounds at a concentration of 0.05% inactivated more than 3-Log10 (90.99%) of the spores of Bacillus sp. after an incubation period of four hours, and all the spores were killed at a concentration of 0.1%. The structures were recognizably elucidated based on 1D and 2D-NMR analyses (1H, 13C, COSY, HSQC, and HMBC) and mass spectrometry data. Compounds 1, and 2 were isolated for the first time from this plant. In conclusion, the two compounds show a promising potential of antibacterial and sporicidal activities against Bacillus sp. and thus can be developed as an anti-Bacillus agent.

Matched MeSH terms: Aldehydes/isolation & purification; Aldehydes/pharmacology*
Fulltext Efficient Catalyst One-Pot Synthesis of 7-(Aryl)-10,10-dimethyl-10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione Derivatives Complemented by Antibacterial Activity

Al-Majedy YK, Al-Amiery AA, Kadhum AA, Mohamad AB

Biomed Res Int, 2016;2016:5891703.
PMID: 27563671 DOI: 10.1155/2016/5891703

The problem of bacteria resistance to many known agents has inspired scientists and researchers to discover novel efficient antibacterial drugs. Three rapid, clean, and highly efficient methods were developed for one-pot synthesis of 7-(aryl)-10,10-dimethyl-10,11-dihydrochromeno[4,3-b]chromene-6,8(7H,9H)-dione derivatives. Three components are condensed in the synthesis, 4-hydroxycoumarin, 5,5-dimethyl-1,3-cyclohexanedione, and aromatic aldehydes, using tetrabutylammonium bromide (TBAB), diammonium hydrogen phosphate (DAHP), or ferric chloride (FeCl3), respectively. Each method has different reaction mechanisms according to the catalyst. The present methods have advantages, including one-pot synthesis, excellent yields, short reaction times, and easy isolation of product. All catalysts utilized in our study could be reused several times without losing their catalytic efficiency. All synthesized compounds were fully characterized and evaluated for their antibacterial activity.

Matched MeSH terms: Aldehydes/chemical synthesis; Aldehydes/pharmacology
Fulltext Novel macromolecules derived from coumarin: synthesis and antioxidant activity

Al-Amiery AA, Al-Majedy YK, Kadhum AA, Mohamad AB

Sci Rep, 2015;5:11825.
PMID: 26134661 DOI: 10.1038/srep11825

The rational design of 4-hydroxycoumarins with tailor-made antioxidant activities is required nowadays due to the wide variety of pharmacologically significant, structurally interesting of coumarins and researcher orientation toward green chemistry and natural products. A simple and unique coumarins have been achieved by reaction of 4-hydroxycoumarin with aromatic aldehyde accompanied with the creation of a macromolecules have 2-aminothiazolidin-4-one. The molecular structures of the compounds were characterized by the Fourier transformation infrared and Nuclear magnetic resonance spectroscopies, in addition to CHN analysis. The scavenging abilities of new compounds against stable DPPH radical (DPPH•) and hydrogen peroxide were done and the results show that the compounds exhibited high antioxidant activates.

Matched MeSH terms: Aldehydes
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/pharmacology; Aldehydes/chemistry*
Synthesis, characterization, monoamine oxidase inhibition, molecular docking and dynamic simulations of novel 2,1-benzothiazine-2,2-dioxide derivatives

Ahmad S, Zaib S, Jalil S, Shafiq M, Ahmad M, Sultan S, et al.

Bioorg Chem, 2018 10;80:498-510.
PMID: 29996111 DOI: 10.1016/j.bioorg.2018.04.012

In this research work, we report the synthesis and biological evaluation of two new series of 1-benzyl-4-(benzylidenehydrazono)-3,4-dihydro-1H-benzo[c] [1,2]thiazine 2,2-dioxides and 1-benzyl-4-((1-phenylethylidene)hydrazono)-3,4-dihydro-1H-benzo[c][1,2]thiazine 2,2-dioxides. The synthetic plan involves the mesylation of methyl anthranilate with subsequent N-benzylation of the product. The methyl 2-(N-benzylmethylsulfonamido)benzoate was subjected to cyclization reaction in the presence of sodium hydride to obtain 1-benzyl-1H-benzo[c][1,2]thiazin-4(3H)-one 2,2-dioxide which was treated with hydrazine hydrate to get corresponding hydrazone precursor. Finally, the titled compounds were obtained by reaction of hydrazone with various substituted aldehydes and ketones. The synthesized derivatives were subjected to carry out their inhibition activities against monoamine oxidases along with modelling investigations to evaluate their binding interactions and dynamic stability during the docking studies. The inhibition profile of potent compounds was found as competitive for both the isozymes. The compounds were more selective inhibitors of MAO-A as compared to MAO-B. Moreover, drug likeness profile of the derivatives was evaluated to have an additional insight into the physicochemical properties. The molecular dynamic simulations predicted the behaviour of amino acids with the active site residues.

Matched MeSH terms: Aldehydes
Fulltext A CONVENIENT SYNTHESIS OF 5-ARYLIDENE MELDRUM'S ACID DERIVATIVES VIA KNOEVENAGEL CONDENSATION

Adryana Izzati Adnan, noorhidayah977@uitm.edu.my, Nur Ain Nabilah Ash’ari

Journal of Academia Universiti Teknologi MARA Negeri Sembilan, 2021;9(1):80-84.
MyJurnal

A series of ten 5-arylidene Meldrum’s acid derivatives had been synthesised in excellent yield via Knoevenagel condensation. This method does not require catalyst, or any further purification. Isopropylidene malonate (2,2-dimethyl-1,3-dioxane-4,6-dione), also known as Meldrum’s acid, is utilised as a core skeleton for various kind of reactions. Meldrum’s acid has features of a peculiar ring- opening sequences based on nucleophile-sensitive carbonyl functional groups at C-4 and C-6, which has made it possible for useful synthetic transformations, as well as its high acidity of methylene hydrogen at carbon position C-5. Hence, it allows the compound to be a flexible reagent for further reaction to prepare other derivatives. Therefore, Meldrum’s acid derivatives showed high potential of biological functions, such as antibacterial, antimalarial and antioxidant activities due to the olefinic linkage which played an important role in the enhancement of antimalarial activity. Furthermore, when arylidene Meldrum’s acid transformed to epoxide, the compound showed losses of antimalarial behaviour. Additionally, this compound has unique molecules due to the high acidity of methylene hydrogen at the carbon-5 position to initiate various reactions with different functional groups. In this research, Meldrum’s acid, 3 and ten its 5-arylidene derivatives (4a-e) and (5a-e) were synthesised by using two short and efficient reaction steps. The first step involved the condensation of malonic acid, 1 with acetone, 2 in acetic anhydride and acid via one-pot reaction to give Meldrum’s acid, 3 in 50% overall yield. Having Meldrum’s acid in hand, the reaction was proceeded with the Knoevenagel condensation reaction by using various functional groups, such as aryl aldehydes and aryl amines. All the synthesised compounds were characterised by using 1H and 13C spectroscopy.

Matched MeSH terms: Aldehydes
Fulltext Crystal structure of 5-[4-(di-methyl-amino)-phen-yl]-3-(4-methyl-phen-yl)-4,5-di-hydro-1H-pyrazole-1-carbaldehyde

Adam F, Samshuddin S, Ameram N, Subramaya, Samartha L

Acta Crystallogr E Crystallogr Commun, 2015 Dec 1;71(Pt 12):o1031-2.
PMID: 26870482 DOI: 10.1107/S2056989015023294

The title compound, C19H21N3O, comprises a central pyrazole ring which is N-connected to an aldehyde group and C-connected twice to substituted benzene rings. The pyrazole ring is twisted on the C-C single bond, and the least-squares plane through this ring forms dihedral angles of 82.44 (5) and 4.52 (5)° with the (di-methyl-amino)-benzene and p-tolyl rings, respectively. In the crystal, weak C-H⋯O hydrogen bonds link mol-ecules into supra-molecular tubes along the b axis.

Matched MeSH terms: Aldehydes
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/pharmacology*; Aldehydes/toxicity; Aldehydes/chemistry
Fulltext Cytotoxic effect of damnacanthal, nordamnacanthal, zerumbone and betulinic acid isolated from Malaysian plant sources

International Food Research Journal, 2010;17(3):711-719.
MyJurnal

The present study was to evaluate the toxicity of damnacanthal, nordamnacanthal, betulinic acid and zerumbone isolated from local medicinal plants towards leukemia cell lines and immune cells by using MTT assay and flow cytometry cell cycle analysis. The results showed that damnacanthal significantly inhibited HL-60 cells, CEM-SS and WEHI-3B with the IC50 value of 4.0 µg/mL, 8.0 µg/mL and 3.3 µg/mL, respectively. Nordamnacanthal and betulinic acid showed stronger inhibition towards CEM-SS and HL-60 cells with the IC50 value of 5.7 µg/mL and 5.0 µg/mL, respectively. In contrast, Zerumbone was demonstrated to be more toxic towards those leukemia cells with the IC50 value less than 10 µg/mL. Damnacanthal, nordamnacanthal and betulinic acid were not toxic towards 3T3 and PBMC compared to doxorubicin which showed toxicity effects towards 3T3 and PBMC with the IC50 value of 3.0 µg/mL and 28.0 µg/mL, respectively. The cell cycle analysis exhibited that damnacanthal exerted its toxicity effect towards HL-60 cells by inducing apoptosis with value of 25% after 72 hours treatment. Thus, these compounds could be the potential anticancer drug with less toxic side effect.

Matched MeSH terms: Aldehydes