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

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Diketopiperazine Cyclo-(S-Pro-R-Leu) Produced by Periconia pseudobyssoides K5 Isolated from Toona sureni (Meliaceae) and its Heme Polymerization Inhibition Activity Azhari, Azmi; Harneti, Desi; Wulandari, Asri Peni; Mulyani, Yeni; Purbaya, Sari; Sari, Aprilia Permata; Pratama, Galih Bayu; Supratman, Unang; Shiono, Yoshihito
Makara Journal of Science Vol. 27, No. 1
Publisher : UI Scholars Hub

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Abstract

Fungi endophytes are living microorganisms colonizing inside the internal tissue of a plant and provide ecological benefits for their host. Endophytes provide various metabolites for plant adaptation toward biotic and abiotic stresses and have tremendous pharmacological activities. Toona sureni (T. sureni) (Meliaceae) belongs to the Toona genera and is reported to have antimalarial activity. To determine the compounds produced by the endophytic fungus from this plant, we isolated a compound from Periconia pseudobyssoides (P. pseudobyssoides) K5 endophytes from the stem bark of T. sureni. Diketopiperazine cyclo-(S-Pro-R-Leu), a non-ribosomal peptide, was isolated from brown rice fermented at 28 ± 2 ℃ for 30 days. The structure was determined by spectroscopic methods including fourier-transform infrared spectroscopy, mass spectrometry, and 1D and 2D nuclear magnetic resonance techniques. This compound was evaluated for heme polymerization inhibition activity (HPIA) with an IC50 value of 9.89 ± 0.24 mmol/L compared with positive control chloroquine phosphate with an IC50 value of 3.08 ± 0.58 mmol/L. This compound has been categorized as having low activity three times lower than positive control chloroquine phosphate. This information provides new leads about the compound diketopiperazine cyclo-(S-Pro-R-Leu) produced by P. pseudobyssoides K5 endophytes having low activity in inhibiting heme polymerization. In the future, to explore the potency of this compound as antimalarial agent, the other antimalarial test such as lactate dehydrogenase assay might be useful.
Cholestan Steroids from The Stem Bark of Aglaia angustifolia Miq and Their Cytotoxic Activity against MCF-7 Breast Cancer Cell Lines Hutagaol, Ricson Pemimpin; Mozef, Tjandrawati; Fajriah, Sofa; Primahana, Gian; Supratman, Unang; Harneti, Desi; Hidayat, Ace Tatang; Awang, Khalijah; Shiono, Yoshihito
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.2023.18.2.6205

Abstract

With about 120 species, Aglaia is one of the largest genera of the plant family Meliaceae (the mahogany plants). Various Aglaia species have been investigated since the 1960s for their phytochemical constituents and biological properties. This research objective was to find secondary metabolites that have activity as anti-breast cancer compounds from endemic Indonesian Aglaia, such as Aglaia angustifolia Miq. Two cholestan type steroids, stigmast-5en-3α-acetat (1), as a new steroid with α-sterochemistry of acetyl moiety at C-3 and 23a-homostigmast-5en-3β-ol (2), with unusual side chain were isolated for the first time from the stem bark of Aglaia angustifolia Miq or known as segara tree in Kalimantan. The chemical structures of two steroids were identified with spectroscopic data, including IR, NMR (1H, 13C, DEPT 135°, HMQC, HMBC, NOESY, 1H-1H COSY) and HRTOF-MS, as well as by comparing with previously reported spectral data. These two steroids were isolated for the first time from this genus. Steroids 1 and 2 were evaluated for cytotoxic activity against MCF-7 breast cancer cells and showed weak activity with IC50 values of 829.0 and 903.0 µg/mL, respectively.
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.
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.
Co-Authors Ace Tatang Hidayat Asri Peni Wulandari, Asri Peni Azmi Azhari, Azmi Azmi, Mohamad Nurul Dadan Sumiarsa Darwati Darwati Desi Harneti Putri Huspa Dikdik Kurnia Farabi, Kindi Harizon Harizon Hilmayanti, Erina Hutagaol, Ricson Pemimpin Khalijah Awang Mustaqim, Iqbal Wahyu Naini, Al Arofatus Nurlelasari Nurlelasari Pratama, Galih Bayu Primahana, Gian Purbaya, Sari Rani Maharani Sari, Aprilia Permata Sinaga, Siska Elisahbet Sofa Fajriah Tati Herlina Tjandrawati Mozef Tri Mayanti Unang Supratman Yeni Mulyani