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Synthesis and Biological Evaluation of N'-Arylidene-4-Hydroxybenzohydrazides against α-Glucosidase Enzyme Danova, Ade; Hermawati, Elvira; Chavasiri, Warinthorn
Jurnal Kartika Kimia Vol 6 No 2 (2023): Jurnal Kartika Kimia
Publisher : Department of Chemistry, Faculty of Sciences and Informatics, University of Jenderal Achmad Yani

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.26874/jkk.v6i2.210

Hydrazides have been reported to have a broad spectrum of bioactivities, such as anticancer, antifungal, antibacterial, and antidiabetic. Thus, our work aimed to synthesize N'-arylidene-4-hydroxybenzohydrazides and investigate their α-glucosidase inhibition. Three compounds (AD-H1-3) were synthesized with a yield of product from 33 to 65% and then characterized using 1H-and 13C-NMR spectroscopy. The in vitro α-glucosidase inhibition demonstrated that AD-H2 possessing two hydroxy groups on arylidene moiety showed the best inhibitory activity against α-glucosidase enzyme with an IC50 value of 14.4 µM compared with acarbose as a positive control with IC50 value of 93.6 µM. Thus, AD-H2 could be a candidate as a lead compound for antidiabetics.

Synthesis, Evaluation, and Molecular Docking Study of 4-Monoacyl Resorcinol Against Tyrosinase Enzyme Danova, Ade; Maulana, Yusuf Eka; Hermawati, Elvira; Chavasiri, Warinthorn
Indonesian Journal of Chemical Research Vol 11 No 2 (2023): Edition for September 2023
Publisher : Jurusan Kimia, Fakultas Sains dan Teknologi, Universitas Pattimura

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.30598//ijcr.2023.11-nov

Tyrosinase is a crucial enzyme in melanin production to protect the skin from ultraviolet, leading to skin cancers. This study synthesized eight compounds of acyl resorcinol with long-chain carbon (1-8) and structurally elucidated by 1H and 13C NMR. The in vitro evaluation of eight synthesized compounds against tyrosinase enzyme showed that 4-heptanoyl resorcinol (6) exhibited high inhibitory activity compared with the kojic acid as standard. In addition, the molecular docking study demonstrated that 6 showed lower binding energy (-7.3 kcal/mol) than kojic acid (-6.9 kcal/mol) and possessed interaction with crucial residues in the active site.

Garciniaxanthone E and 12b-Hydroxy-des-D-garcigerrin A from The Tree Bark Garcinia dulcis and their Inhibitory Properties against Receptor Tyrosine Kinases Kurniadewi, Fera; Aqilah, Amadita Shafa; Kartika, Irma Ratna; Nurjayadi, Muktiningsih; Hermawati, Elvira; Danova, Ade
Jurnal Kimia Valensi Jurnal Kimia VALENSI, Volume 10, No. 1, May 2024
Publisher : Syarif Hidayatullah State Islamic University

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.15408/jkv.v10i1.38159

Two xanthone derivatives, garciniaxanthone E (1) and 12b-Hydroxy-des-D-garcigerrin A (2) have been isolated from ethyl acetate extract of the tree bark of Garcinia dulcis. The Ultraviolet (UV), Infrared (IR), Nuclear Magnetic Resonance (NMR), and Mass Spectrometry (MS) data analysis elucidated the structure of the isolated compounds. This study represents the first evaluation of compounds 1 and 2 in terms of their efficacy against receptor tyrosine kinases. The results showed that compound 1 exhibited weak activity with 12% inhibition against Insulin Receptor (InsR), while compound 2 showed moderate activity with 29% inhibition against epidermal growth factor receptor (EGFR). A molecular docking study targeting EGFR-TK suggests that the hydroxyl group at C-4 on compound 2 can be demolished to raise the inhibitory activity in future research.

Isolation and Transformation of Tefrosin From The Seed of Tephrosia Vogelii With SelectfluorTM Yulvia, Ana; Hermawati, Elvira; Danova, Ade; Oktavianawati, Ika; Reza, Muhammad
Indonesian Chimica Letters Vol. 3 No. 2 (2024)
Publisher : Department of Chemistry, Faculty of Mathematics and Natural Sciences, University of Jember

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.19184/icl.v3i2.4274

In this study, tefrosin (1), a known phenolic compound, was successfully isolated and identified from the seed extract of Tephrosia vogelii. The structure of this compound was determined based on 1D and 2D NMR spectroscopy. Furthermore, the isolated compound was transformed using 0.5 equivalent of selectfluor™ in acetonitrile solvent at 100 oC for 3 hours. The reaction product, namely dehydrotephrosine (2), is new reaction product from selectfluor™ reagent as a catalyst in tertiary alcohol dehydration in aromatic group. This finding highlights the effectiveness of selectfluor™ as a catalyst in dehydration reactions, demonstrating its potential to introduce new chemical properties to compounds. The study underscores the versatility of selectfluor™ and its ability to facilitate the generation of valuable derivatives from phenolic compounds. These results provide insights into the reactivity of tefrosin and offer a new approach for chemical transformations involving phenolic substrates.

Discovery of thymol-fused chalcones as new competitive \(\alpha\)-glucosidase inhibitors: Design, synthesis, biological evaluation, and molecular modeling studies Danova, Ade; Hermawati, Elvira; Chavasiri, Warinthorn; Mujahidin, Didin; Alni, Anita; Roswanda, Robby
Communications in Science and Technology Vol 9 No 2 (2024)
Publisher : Komunitas Ilmuwan dan Profesional Muslim Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.21924/cst.9.2.2024.1497

This study aims to synthesize and evaluate the inhibitory activity of thymol derivatives targeting ?-glucosidase using in vitro and in silico studies. Ten thymol derivatives (2-11) including five new thymol-fused chalcones (7-11) were successfully synthesized. Among them, four compounds (4, 8, 9, 11) showed the best inhibitory activity with IC50 values of 18.45, 13.75, 8.86, and 10.67µM compared with acarbose (IC50 = 832.82 µM), respectively. The kinetic study of three new thymol-fused chalcones (8, 9, 11) exhibited a competitive inhibition. Molecular docking demonstrated the predicted interactions between ligand (8, 9, 11) and ?-glucosidase, which are responsible for inhibiting the enzyme's catalytic abilities. Furthermore, molecular dynamics simulation of the enzyme-ligand 9 complex indicated that this complex was stable in aqueous condition. This research contributes significantly to the understanding of thymol-fused chalcones that may have therapeutic potential and their possible application in the treatment of type 2 diabetes mellitus (T2DM) for further study.

In vitro evaluation, molecular docking, and molecular dynamics studies of resorcinol derivatives against yeast α‐glucosidase Danova, Ade; Hermawati, Elvira; Chavasiri, Warinthorn; Mujahidin, Didin; Musthapa, Iqbal; Kurniadewi, Fera
Indonesian Journal of Biotechnology Vol 30, No 3 (2025)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijbiotech.106495

Nine resorcinol derivatives were evaluated for their ability to inhibit yeast α‐glucosidase using the in vitro method. Three molecular docking programs (Autodock Vina, Autodock4 and DockThor) were employed to determine the binding energies. The results showed that two resorcinol derivatives possessing butanoyl (1) and butyl (9) groups demonstrated good inhibitory activity against α‐glucosidase, with IC50 values of 75.9 and 33.3 µM respectively, compared with other derivatives (2–8) and acarbose (IC50 = 832.8 µM). Furthermore, molecular docking indicated that compounds 1 and 9 had better binding affinities than acarbose and the native ligand. Both compounds showed similar interactions with Asp349 and Glu408, which were associated with acarbose and the native ligand. Moreover, molecular dynamics analysis indicated that compound 9 exhibited greater stability than compound 1 when complexed with α‐glucosidase. Therefore, compound 9 has the potential for further studies, both in vitro and in vivo, to evaluate its toxicity, side effects and efficacy.

Anti-tyrosinase Activity of 3’,4’,5’-Trimethoxychalcones: Experimental and Computational Studies Danova, Ade; Hermawati, Elvira; Chavasiri, Warinthorn; Mujahidin, Didin; Musthapa, Iqbal; Kurniadewi, Fera
Science and Technology Indonesia Vol. 10 No. 4 (2025): October
Publisher : Research Center of Inorganic Materials and Coordination Complexes, FMIPA Universitas Sriwijaya

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.26554/sti.2025.10.4.982-989

Tyrosinase inhibitors are utilized as preservatives in the food industry and skin-lightening agents in the medical and cosmetic sectors. However, there has been little progress in clinical trials owing to challenges such as low bioavailability, significant skin irritation, and instability. Hence, the objective of this study was to evaluate the inhibitory activity of 3’,4’,5’-trimethoxychalcones through in vitro, molecular docking and molecular dynamics studies targeting tyrosinase. Five 3’,4’,5’-trimethoxychalcones (1-5) were evaluated their biological activity against tyrosinase for the first time. Compounds 4 and 5 were excellent inhibitory activity against tyrosinase with IC50 values of 1.9 and 1.7 μm compared with kojic acid and ascorbic acid. Isovanillin and catechol moieties are vital in this present study. This result was supported with molecular docking by shaping interaction in the catalytic site with histidine residues and the stability evaluation of the inhibitor-protein complexes using molecular dynamics simulation. The lipinski’s rules showed a fit with two potential inhibitors (4, 5). Therefore, 3’,4’,5’-trimethoxychalcones possessing isovanillin and catechol parts in the B ring are promising candidate for further study as tyrosinase inhibitors by evaluating their efficacy in vitro and in vivo.

Garciniaxanthone E and 12b-Hydroxy-des-D-garcigerrin A from The Tree Bark Garcinia dulcis and their Inhibitory Properties against Receptor Tyrosine Kinases Kurniadewi, Fera; Aqilah, Amadita Shafa; Kartika, Irma Ratna; Nurjayadi, Muktiningsih; Hermawati, Elvira; Danova, Ade
Jurnal Kimia Valensi Jurnal Kimia VALENSI, Volume 10, No. 1, May 2024
Publisher : Department of Chemistry, Faculty of Science and Technology Syarif Hidayatullah Jakarta State Islamic University

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.15408/jkv.v10i1.38159

Two xanthone derivatives, garciniaxanthone E (1) and 12b-Hydroxy-des-D-garcigerrin A (2) have been isolated from ethyl acetate extract of the tree bark of Garcinia dulcis. The Ultraviolet (UV), Infrared (IR), Nuclear Magnetic Resonance (NMR), and Mass Spectrometry (MS) data analysis elucidated the structure of the isolated compounds. This study represents the first evaluation of compounds 1 and 2 in terms of their efficacy against receptor tyrosine kinases. The results showed that compound 1 exhibited weak activity with 12% inhibition against Insulin Receptor (InsR), while compound 2 showed moderate activity with 29% inhibition against epidermal growth factor receptor (EGFR). A molecular docking study targeting EGFR-TK suggests that the hydroxyl group at C-4 on compound 2 can be demolished to raise the inhibitory activity in future research.

Experimental and Molecular Docking Study of 3′,4′,5′-Trimethoxychalcones Targeting Overexpressed Protein in HCT-116 Colon Cancer Cells Danova, Ade; Wonganan, Piyanuch; Hermawati, Elvira; Kurniadewi, Fera; Musthapa, Iqbal; Chavasiri, Warinthorn
Jurnal Kimia Valensi Jurnal Kimia VALENSI, Volume 11, No. 2, November 2025
Publisher : Department of Chemistry, Faculty of Science and Technology Syarif Hidayatullah Jakarta State Islamic University

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.15408/jkv.v11i2.46483

Cancer poses a substantial global health challenge. Colorectal cancer (CRC) is the second leading cause of cancer-related mortality after lung cancer and is associated with high mortality rates worldwide. Chalcones have attracted significant interest because of their diverse biological properties, including potential anticancer effects. In this study, five 3′,4′,5′-trimethoxychalcones (1-5) were tested against HCT-116 colon cancer cells using an MTT assay for the first time. Molecular docking was conducted to predict molecular interactions targeting three proteins (tubulin, EGFR, and CDK2). Among the five, four compounds (1, 3, 4, and 5) exhibited strong inhibitory activity against HCT-116 colon cells, with IC50 values < 10 µM. Compounds 1-5 showed potency as drug candidates based on the Lipinski rules and pharmacokinetic profiles using SwissADME and pkCSM online tools. Moreover, molecular docking was performed on compound 5 against three protein targets (tubulin, EGFR, CDK2) with binding affinities of -7.4, -7.3, and -8.5 kcal/mol, respectively, and showed major H-bond interactions. Therefore, these results suggest that compound 5 could be a potential inhibitor to be developed in future studies, both in vitro and in vivo, to understand its inhibition mechanism and efficacy.

Study and Characterization of Nitration of Isovanillic Acid Derivatives using NMR and Mass Spectroscopy Hermawati, Elvira; Sa'adah, Pipih Lutfi; Danova, Ade; Mujahidin, Didin; Musthapa, Iqbal
Chimica et Natura Acta Vol 13, No 3 (2025)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.24198/cna.v13.n3.62271

Isovanillic acid and its derivatives serve as precursors in the synthesis of EGFR tyrosine kinase inhibitors, which are used to treat cancer cell lines. A crucial step in this process is the nitration of isovanillic acid through nucleophilic aromatic substitution, resulting in 6-nitroisovanilic acid and its derivatives, which act as intermediates for forming a quinazolinone ring. However, this study revealed that direct nitration of isovanillic acid derivatives led to unexpected products, such as 3-hydroxy-4-methoxy-2,6-dinitrobenzoic acid (1) and 4-(3-(2-methoxy-4-nitrophenoxy)propyl)morpholine (4). Additionally, the optimal conditions for etherification of 2 with N-(3-chloropropyl)morpholine to produce 3 involved using Cs2CO3 in DMF and refluxing for 7 hours, achieving an 89% yield. All synthesized compounds were characterized using NMR spectroscopy, and mass spectrometry was employed for two compounds (3, 4). Compound 1 represents the first report of direct nitration of isovanillic acid. Compound 4 was synthesized for the first time from 3 through a one-pot process involving hydrolysis and decarboxylation, followed by nitration at carbon C-1 without metal catalysis, as confirmed by a NOESY 1D experiment. Moreover, the application of 4 could hold promise for future advancements in medicinal chemistry.

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