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All Journal Indonesian Journal of Chemistry Molekul: Jurnal Ilmiah Kimia
Farabi, Kindi
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Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry Materials Science & Nanotechnology

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Morelloflavone and Molecular Docking from Stembark of Chisocheton lasiocarpus and Its Cytotoxic Activity Against Breast Cancer Mcf-7 Cell Lines Nurlelasari, Nurlelasari; Harneti, Desi; Maharani, Rani; Darwati, Darwati; Mayanti, Tri; Farabi, Kindi; Hanafi, Muhammad; Supratman, Unang
Molekul Vol 18 No 2 (2023)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2023.18.2.6845

Abstract

Chisocheton is a plant of the Meliaceae family which has been known as a source of limonoids, triterpenoids, steroids, alkaloids and phenolics. This plant is the second largest in the Meliaceae, with 53 species widely distributed in tropical and subtropical regions including Indonesia. From this genus, compounds that have interesting activities have been found, including anti-inflammatory, antimalarial, cytotoxic, antitumor and anticancer. One of the species that has the potential to find new compounds is Chisocheton lasiocarpus because there are still few phytochemical studies. This study aims to inform the structural elucidation of one of the compounds from the stem bark of C. lasiocarpus, namely morelloflavone and its cytotoxic potential against breast cancer cells using the in silico method against ER-α receptors (PDB code: 3ERD), ER-β (PDB code: 1QKM). ) and HER-2 (GDP code: 3PP0).
The Sesquiterpenoids from Aglaia cucullata Peel Fruit and Their Cytotoxic Activities Against B16-F10 and HeLa Cancer Cell Lines Supratman, Unang; Anjari, Intan Hawina; Harneti, Desi; Naini, Al Arofatus; Farabi, Kindi; Anwar, Risyandi
Molekul Vol 18 No 3 (2023)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2023.18.3.7900

Abstract

Sesquiterpenoids are terpenoid derivative compounds that have a diverse chemical structure and pharmacological effects. Sesquiterpenoids can be found in many plants of Aglaia which is the large source of natural compounds in the Meliaceae family. This research was aimed to elucidate the structure of sesquiterpenoids from the peel fruit of Aglaia cucullata and their cytotoxic activities against two human cancer cell lines. The n-hexane extract was separated and further purified by various chromatographic methods to yiled three sesquiterpenoids. The structure of these sesquiterpenoids were identified by spectroscopy analysis including MS, IR, 1H-NMR, 13C-NMR and DEPT as well as compared with spectral data which reported previously. The sesquiterpenoid compounds 1-3 were identified as spathulenol (1), alismol (2), and 10-oxo-isodauc-3-en-15-al (3). The cytotoxic activity of three sesquiterpenoid compounds were tested against HeLa cervical cancer cell and B16-F10 skin cancer cell using the PrestoBlue method. Compound 2 exhibited the highest activity against both HeLa and B16-F10 cancer cell lines with IC50 48.11 μg/mL and 57.05 μg/mL, respectively.
Triterpenoids From Swietenia mahagoni L Jacq. and Their Cytotoxic Activity against MCF-7 Breast Cancer and CV-1 Normal Kidney Cell Lines Supratman, Unang; Abdullah, Fajar Fauzi; Farabi, Kindi; Nurlelasari, Nurlelasari; Awang, Khalijah; Nafiah, Mohamad Azlan
Molekul Vol 19 No 2 (2024)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2024.19.2.9358

Abstract

ABSTRACT. Triterpenoid is a group of natural products with various remarkable activities, including cytotoxic. One of the sources for this type of compounds is Swietenia genus belong to Meliaceae family. This genus known to contains various secondary metabolites including limonoids, flavonoids, and triterpenoids. Especially for triterpenoid, there is limited report on isolation as well as biological activity from Swietenia genus, such as Swietenia mahagoni. In this research, three triterpenoid compounds have been successively isolated and identified from n-hexane extract, namely, (-)-leucophyllone (1), toonaciliatavarin E (2), and moronic acid (3). All isolated were assed against MCF-7 breast cancer and CV-1 normal kidney cell lines. The result showed that only moronic acid (3) performed moderate activity against two cells with IC50 of 63.10 and 48.04 µM, respectively. The other isolated compounds (1 and 2) showed weak cytotoxicity with IC50 > 500 µM. Based on preliminary structure activity relationship, revealed that pentacyclic triterpenoid (moronic acid, 3) showed stronger cytotoxicity compare with tetracyclic triterpenoids (-)-leucophyllone (1) and toonaciliatavarin E (2). Keyword: Cytotoxicity, MCF-7 and CV-1, Switennia mahagoni, Triterpenoids.
Sesquiterpenoids from The Stem Bark of Aglaia cucullata (Meliaceae) and Their Cytotoxic Activity Against A549 Lung Cancer Cell Lines Mustaqim, Iqbal Wahyu; Harneti, Desi; Naini, Al Arofatus; Hilmayanti, Erina; Darwati, Darwati; Nurlelasari, Nurlelasari; Mayanti, Tri; Maharani, Rani; Farabi, Kindi; Hidayat, Ace Tatang; Supratman, Unang; Fajriah, Sofa; Azmi, Mohamad Nurul; Shiono, Yoshihito
Molekul Vol 19 No 2 (2024)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2024.19.2.9823

Abstract

ABSTRACT. Sesquiterpenoids are a class of terpenoid compounds with a remarkable diversity of structures and biological activities. Sesquiterpenoids are primarily found in higher plants, such as the Meliaceae family's Aglaia genus. Aglaia cucullata is a species of Aglaia that is still rarely explored and can potentially contain sesquiterpenoid compounds with cytotoxic activity. Hence, the research intended to isolate sesquiterpenoids from the n-hexane extract of A. cucullata stem bark and evaluate their cytotoxic effect against A549 lung cancer cells. Compounds 1 and 2 were isolated and purified from n-hexane extracts utilizing various chromatographic techniques. The structure of compounds 1 and 2 was determined by analyzing various spectroscopic methods (IR, MS, and NMR) and comparing them to previously reported spectral data. Compound 1 was identified as an isodaucane-type sesquiterpenoid, 10-hydroxy-6,10-epoxy-7(14)-isodaucane, and was first reported in Meliaceae family. Compound 2 was confirmed as an eudesmane-type sesquiterpenoid, eudesm-4(15)-ene-1β,6α-dihydroxy, and was first reported in Aglaia cucullata. Cytotoxic activity of 1 and 2 were investigated in vitro against A549 lung cancer cells using the PrestoBlue assay and resulted in inactive and low cytotoxicity with IC50 values of 292.77 and 90.55 μM, respectively. Key words: Aglaia cucullata, , A549 cell lines, cytotoxic activity, Meliaceae, sesquiterpenoids.
Four Azadirone-Type Limonoids from Chisocheton Pentandrus Stem Bark and Their Cytotoxic Acitivity Against Mcf-7 Breast Cancer Cell Lines Supratman, Unang; Runadi, Dudi; Naini, Al Arofatus; Purnama, Purnama; Mayanti, Tri; Harneti, Desi; Nurlelasari, Nurlelasari; Maharani, Rani; Farabi, Kindi; Nafiah, Mohamad Azlan
Molekul Vol 19 No 2 (2024)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2024.19.2.11085

Abstract

ABSTRACT. Limonoid group belongs to triterpenoid that has undergone further oxidation accompanied by the loss of four carbon atoms to form a furan ring in the chain. This limonoid compound is often found in the Chisocheton genus. Limonoid compounds have been known as compounds with high structural variations and this makes limonoids have diverse and interesting activities, including cytotoxic and anticancer. In the course of our continuing study for limonoid constituents that have cytotoxic activity against cancer cell lines, methanol extract of stem bark from the Chisocheton pentandrus plant provides significant activity. The methanol extract was separated using various chromatographic techniques in the normal and reverse stationary phase to produce four azadirone-type limonoid compounds (1-4). The elucidation structure of 1-4 was determined using spectroscopic methods including, UV-Visible, IR, and 1D-NMR as well as optical rotation. All four known compounds were established as trichilenone acetate (1), toonaciliaton C (2), 11α-acetoxiazadiron (3), and 16β-hydroxydisobinine (4). The cytotoxicity of compounds 1-4 was assessed by examination using the resazurin method, which showed that compound 4 was the promising constituent against the MCF-7 cells with an IC50 value of 43.1 µM and was stronger than its positive control. Keywords: Azadirone-type limonoid, Chisocheton pentandrus, cytotoxic activity, Meliaceae.
Steroids Produced by Endophytic Fungi (Fusarium phaseoli) Isolated from Chisocheton macrophyllus and their Antibacterial Activity against Escherichia coli and Staphylococcus aureuss Katja, Dewa Gede; Sari, Aprilia Permata; Sinaga, Siska Elisahbet; Nurlelasari, Nurlelasari; Farabi, Kindi; Sofian, Ferry Ferdiansyah; Fajriah, Sofa; Naini, Al Arofatus; Supratman, Unang
Molekul Vol 20 No 1 (2025)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2025.20.1.12727

Abstract

ABSTRACT. Steroids are secondary metabolic derivatives of terpenes containing the tetracyclic ring system known to exhibit fascinating pharmacological activity. Steroids are distributed in various genera of endophytic fungi including Fusarium genus which lives inside a higher tree such as Chisocheton macrophyllus. The purpose of this research is to identify and characterize the chemical structure of steroids generated by F. phaseoli, an endophytic fungus obtained from C. macrophyllus roots, as well as to assess their antibacterial activity against Escherichia coli and Staphylococcus aureus. The brown rice medium was fermented with F. phaseoli for six weeks before extraction with ethyl acetate. The extracts yielded four compounds, identified using spectroscopic methods such as FTIR, HRTOF-MS, 1D, and 2D NMR, and then compared to previously described compounds. Compounds 1-4 were identified as ergosterol (1), ergosterol peroxide (2), atroside (3), and cerevisterol (4). The four isolated compounds were evaluated for antibacterial activity against Staphylococcus aureus ATCC 6538 and Escherichia coli ATCC 11229 and displayed activity with MIC50 values of 500 µg/mL. Keywords: Antibacterial activity; Chisocheton macrophyllus; Fusarium phaseoli; steroids.
Dammarane Triterpenoids from Aglaia eximia Miq. and Their Cytotoxic Activity Against P388 Murine Leukemia Cell Farabi, Kindi; Harneti, Desi; Nurlelasari, Nurlelasari; Maharani, Rani; Mayanti, Tri; Hidayat, Ace Tatang; Fajriah, Sofa; Naini, Al Arofatus; Sofian, Ferry Ferdiansyah; Azmi, Mohamad Nurul; Supratman, Unang
Molekul Vol 20 No 1 (2025)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2025.20.1.12796

Abstract

ABSTRACT. Triterpenoids are a large group of secondary metabolites commonly found in plants, exhibiting high diversity in both structural features and biological activities. Meliaceae family is knows as a rich source of the triterpenoid compounds. As the most extensive genus within the Meliaceae family, Aglaia is known to contain many bioactive triterpenoid compounds, including cytotoxic triterpenoids. Among the various types of triterpenoids, dammarane is frequently found in Aglaia and has demonstrated potential cytotoxic activity. This purpose of the research was to isolate and structure determination of four dammarane triterpenoids from the methanol extract of Aglaia eximia stem bark. All four compounds were successfully isolated and identified as, dammar-24-en-3a,20-diol (1), 20S,24S-epoxy-dammar-3a,25-diol (2), (E)-dammar-23-en-3a,20,25-triol (3), and (E)-25-hydroperoxydammar-23-en-3a,20-diol (4), respectively. The compounds were analyzed using a combination of spectroscopic techniques, including HRMS (high-resolution mass spectroscopy), FTIR (fourier transform infrared spectroscopy), and NMR (nuclear magnetic resonance, one and two dimensional). Cytotoxicity assays using the MTT method were applied to compounds 1-4. All isolated compounds (1-4) generated moderate cytotoxic activity against P388 murine leukemia cells with IC50 9.09, 11.03, 5.89, and 5.74 μg/mL, respectively. Preliminary structure-activity relationship (SAR) analysis suggested that the presence of hydroxyl and hydroperoxyl groups at C-25 increases cytotoxicity, whereas the cyclization in the side chain to form an epoxide ring decreases cytotoxicity. Keyword: Triterpenoids, Meliaceae, Aglaia eximia, cytotoxicity, P388 murine leukemia cells
Synthesis of Two Analogues of Xylapeptide A and Their Potency as New Antimicrobial Agent Maharani, Rani; Muchlis, Handi Nugraha; Hidayat, Ace Tatang; Al-Anshori, Jamaludin; Nurlelasari, Nurlelasari; Harneti, Desi; Mayanti, Tri; Farabi, Kindi; Supratman, Unang
Indonesian Journal of Chemistry Vol 25, No 5 (2025)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.100353

Abstract

Xylapeptide A, derived from the fungus Xylaria sp. x Sophora tonkinensis, exhibits potent and selective antimicrobial properties. Our research group has successfully synthesized xylapeptide A. In our recent work, two xylapeptide A analogues (An1 and An2) were synthesized using a combination of solid- and solution-phase synthesis methods. The linear precursors of An1 and An2 were synthesized on 2-CTC resin with the Fmoc strategy. The coupling reagents HBTU/HOBt and HATU/HOAt were employed. Subsequently, the linear precursor was cleaved from the resin using either 20% TFA or a TFE mixture, and then cyclized in solution phase with HBTU. The synthesized products were purified using semi-preparative RP-HPLC, giving the percent yields 16% for An1 and 12% for An2. Both compounds were then characterized by HR-ToF-MS, 1H- and 13C-NMR. The synthesized xylapeptide A and its analogues were evaluated against Bacillus cereus, Bacillus subtilis, Staphylococcus aureus, Enterococcus faecalis, Escherichia coli, Klebsiella pneumoniae, and Candida albicans. The result showed that An2, possessing arginine residue, exhibited higher activity compared to xylapeptide A and An1. This research suggests that xylapeptide A analogues hold great promise as novel antimicrobial agents.
Co-Authors Ace Tatang Hidayat Anjari, Intan Hawina Azmi, Mohamad Nurul Darwati Darwati Desi Harneti Putri Huspa Dewa Gede Katja DUDI RUNADI Fajar Fauzi Abdullah Ferry Ferdiansyah Sofian, Ferry Ferdiansyah Hilmayanti, Erina Jamaludin Al-Anshori Khalijah Awang Muchlis, Handi Nugraha Muhammad Hanafi Mustaqim, Iqbal Wahyu Nafiah, Mohamad Azlan Naini, Al Arofatus Nurlelasari Nurlelasari Purnama Purnama Rani Maharani Risyandi Anwar Sari, Aprilia Permata Shiono, Yoshihito Sinaga, Siska Elisahbet Sofa Fajriah Tri Mayanti Unang Supratman