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All Journal Indonesian Journal of Chemistry Makara Journal of Science Molekul: Jurnal Ilmiah Kimia
Azmi, Mohamad Nurul
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Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry Materials Science & Nanotechnology

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Limonoids Isolated from Chisocheton pentandrus (Meliaceae) Stembarks and its Cytotoxicity Towards MCF-7 Breast Cancer Cell Line Runadi, Dudi; Anjari, Intan Hawina; Purnama, Purnama; Nurlelasari, Nurlelasari; Harneti, Desi; Mayanti, Tri; Harizon, Harizon; Hidayat, Ace Tatang; Salam, Supriatno; Azmi, Mohamad Nurul; Supratman, Unang
Makara Journal of Science Vol. 28, No. 2
Publisher : UI Scholars Hub

Show Abstract | Download Original | Original Source | Check in Google Scholar

Abstract

Chisocheton is a large source of limonoids with various pharmacological effects, such as antiviral, antibacterial, antimalarial, antifungal, and cytotoxic activities. This study aimed to isolate, elucidate, and evaluate the cytotoxicity of limonoids from C. pentandrus stembarks. Isolation was carried out using various separation methods including extraction and column chromatography. Spectral data were analyzed by FT-IR, UV, DEPT 135°, 1H, 13C-NMR, and HRTOF-MS and compared with those previously reported to determine the chemical structure.The obtained limonoids were lasiocarpine (1), lasiocarpine B (2), pentandricine (3), and 16β-hydroxydysobinin (4); all of which were successfully isolated from C. pentandrus for the first time. The cytotoxic activity of these limonoids were also evaluated against Michigan Cancer Foundation-7 (MCF-7) breast cancer cells using PrestoBlue method. Lasiocarpine A revealed the strongest cytotoxicity with an IC50 of 42.62 µM in moderate level.
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.
The Cytotoxic Evaluation of Steroids Isolated from Dysoxylum alliaceum (Blume) Blume ex A.Juss. Riyadi, Sandra Amalia; Naini, Al Arofatus; Mayanti, Tri; Lesmana, Ronny; Azmi, Mohamad Nurul; Supratman, Unang
Molekul Vol 19 No 3 (2024)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.20884/1.jm.2024.19.3.11439

Abstract

Dysoxylum alliaceum belongs to the Dysoxylum genus (Meliaceae) and there are few reports concerning the phytochemical components of this plant. To examine the chemical constituents of Dysoxylum alliaceum stem bark, a phytochemical study has been conducted and identified five known steroids, 3β,16β-dihydroxy-24(S)-methyl cholestenol (1), ergosta-5,22-dien-3β-ol (2), ergosta-7,24(28)-dien-3β-ol (3), 22(E)-ergosta-6,22-dien-3β,5α,8α-triol (4), and 20α-dihydroprogesterone (5) from its ethanolic extract. Spectroscopic data such as FT-IR, HR-ESI-MS, 1D, and 2D NMR as well as comparison with previously published spectral data were used to identify the chemical structures of compounds 1–5. Furthermore, these steroids 1-5 were assessed in vitro regarding their cytotoxic effect against A549 lung cancer cell lines and revealed weak to inactive with IC50 values ranging from 68.52 to >150 µM. Keywords: A549 cell lines, cytotoxic evaluation, Dysoxylum alliaceum (blume) blume ex a.juss, meliaceae, steroid
Sesquiterpenoids from Dysoxylum amooroides Stem Bark: Isolation, Structure Determination, and Cytotoxicity Against MCF-7 Breast Cancer Cells Gunawan, Latifah; Mustofa, Hidayat Nurul; Naini, Al Arofatus; Harneti, Desi; Hidayat, Ace Tatang; Nurlelasari, Nurlelasari; Maharani, Rani; Mayanti, Tri; Fajriah, Sofa; Awang, Khalijah; Azmi, Mohamad Nurul; Supratman, Unang
Indonesian Journal of Chemistry Vol 25, No 1 (2025)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.99121

Abstract

Three sesquiterpenoids, guaianediol (1), alismol (2), and spathulenol (3), were isolated from the n-hexane and ethyl acetate extracts of the stem bark of Dysoxylum amooroides. The three compounds were found in D. amooroides species for the first time. The structures of the isolated compounds were identified and established based on an extensive spectroscopic analysis involving HR-TOF-ESI-MS, IR, and NMR data, as well as a comparison with the previously reported works of literature. Compounds 1-3 were further assessed for cytotoxic effects against MCF-7 breast cancer cells. Guaianediol (1) showed inactive activity with IC50 > 100 µM, alismol (2) showed weak activity with IC50 value of 82.1 µM and spathulenol (3) showed considerable activity with an IC50 value of 15.2 µM. A brief structure-activity relationship and comparison with the previous works were also discussed to understand better the role of guaiane- and aromadendrane-type sesquiterpenoids in the biological activity perspective.
Extraction and Characterization of Phenolic Compounds from the Stem Bark of Sonneratia caseolaris (Lythraceae) and Their Potential Antibacterial Activity Harizon, Harizon; Kurnia, Dikdik; Sumiarsa, Dadan; Herlina, Tati; Sinaga, Siska Elisahbet; Shiono, Yoshihito; Azmi, Mohamad Nurul; Supratman, Unang
Indonesian Journal of Chemistry Vol 25, No 2 (2025)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.98976

Abstract

The ethyl acetate fraction separated from the stembark of Sonneratia caseolaris retrieved three phenolic compounds, including quercetin-3-O-glucoside (1), quercetin (2), and 1-O-(2,4-dihydroxybenzoyl)-β-D-glucopyranose (3). For the first time, compounds 1 and 3 were discovered from Sonneratia genus. Data from various spectroscopic techniques, including mass spectroscopy and one- and two-dimensional NMR, were used to identify their chemical structures. Antibacterial activity has also been assessed for all compounds against Staphylococcus aureus ATCC 25175 and Streptococcus mutans ATCC 6538. Compounds 1–3 displayed varying levels of antibacterial activity against S. aureus and S. mutans. However, all compounds exhibited lower efficacy compared to the control, with their minimum inhibitory concentration (MIC) values ranging from 71.25 to greater than 100 µg/mL. This study provides a foundation for optimizing S. caseolaris phenolic compounds as antibacterial agents and highlights the need for comparative studies within the Sonneratia genus to identify potent bioactive candidates through structural modification or synergistic approaches.
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
Co-Authors Ace Tatang Hidayat Anjari, Intan Hawina Dadan Sumiarsa Darwati Darwati Desi Harneti Putri Huspa Dikdik Kurnia DUDI RUNADI Farabi, Kindi Ferry Ferdiansyah Sofian, Ferry Ferdiansyah Gunawan, Latifah Harizon Harizon Hilmayanti, Erina Khalijah Awang Mustaqim, Iqbal Wahyu Mustofa, Hidayat Nurul Naini, Al Arofatus Nurlelasari Nurlelasari Purnama Purnama Rani Maharani Ronny Lesmana Salam, Supriatno Sandra Amalia Riyadi Shiono, Yoshihito Sinaga, Siska Elisahbet Sofa Fajriah Tati Herlina Tri Mayanti Unang Supratman