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All Journal VALENSI Indonesian Journal of Chemistry Molekul: Jurnal Ilmiah Kimia
Yoshihito Shiono
Department of Food, Life, and Environmental Science, Faculty of Agriculture, Yamagata University, Tsuruoka, Yamagata 997-8555, Japan
Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry Materials Science & Nanotechnology

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Journal : Indonesian Journal of Chemistry

 1 
Cytotoxic Triterpenoids from the Stembark of Aglaia argentea (Meliaceae) Ace Tatang Hidayat; Kindi Farabi; Desi Harneti; Nurlelasari Nurlelasari; Rani Maharani; Ida Nurfarida; Unang Supratman; Yoshihito Shiono
Indonesian Journal of Chemistry Vol 18, No 1 (2018)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (446.817 KB) | DOI: 10.22146/ijc.25052

Abstract

Four dammarane-type triterpenoid compounds, dammar-24-en-3a-ol (1), 3-epi-cabraleahydroxy lactone (2), (E)-25-hydroperoxydammar-23-en-3b,20-diol (3), and dammar-24-en-3β,20-diol (4), were isolated from the methanolic extract of the stembark of Aglaia argentea. Compounds 1-4 were isolated for first time from this plant. The structure of isolated compounds were elucidated by spectroscopic methods including one and two-dimensional NMR as well as mass spectrometric analysis. Compounds, 1-4, along with a known synthetic analog, 20-hydroxy-dammar-24-en-3-on (5), were evaluated their cytotoxic activity against P-388 murine leukemia cells in vitro. The IC50 values of compounds, 1-5 were 9.09 ± 0.10, 68.53 ± 0.08, 5.89 ± 0.08, 22.40 ± 0.11, and 11.53 ± 0.08 µg/mL, respectively. Among the dammarane-type triterpenoids, compounds 1, 3, 4 and 5 having opened side chain showed the stronger activity, wheres compound 2 with cyclic side chain showed weak or no activity. In addition, compound 3 showed strongest activity, indicate that hydroperoxy group at side chain increase cytotoxic activity.
Cytotoxic Sesquiterpenoids from the Stem Bark of Aglaia harmsiana (Meliaceae) Hersa Milawati; Winda Sukmawati; Desi Harneti; Rani Maharani; Nurlelasari Nurlelasari; Ace Tatang Hidayat; Darwati Darwati; Unang Supratman; Yoshihito Shiono
Indonesian Journal of Chemistry Vol 20, No 6 (2020)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (5103.197 KB) | DOI: 10.22146/ijc.47808

Abstract

Three aromadendrane-type sesquiterpenoids, spathulenol (1), 4β,10α-dihydroxyaromadendrane (2), and 4α,10α-dihydroxyaromadendrane (3) were isolated from the stem bark of Aglaia harmsiana (Meliaceae). Compound 3 was isolated for the first time from Aglaia genus. The chemical structures of isolated compounds were elucidated by various spectroscopic methods, including one and two-dimensional NMR, as well as mass spectroscopy analysis. These sesquiterpenoids 1-3 were evaluated for their cytotoxic activity against MCF-7 breast cancer cell lines. The IC50 value of compound 1-3 were 31.65 ± 0.1, 8.41 ± 0.04 and 2.80 ± 0.02 µM, respectively. Among the aromadendrane-type sesquiterpenoids, compounds 2 and 3, which do not have a double bond, showed higher activity than compound 1. Whereas, compound 3 showed the strongest activity indicate that α configuration of hydroxyl group increases the cytotoxic activity.
Triterpenoids from the Stem Bark of Aglaia cucullata (Meliaceae) and Their Cytotoxic Activity against A549 Lung Cancer Cell Line Desi Harneti; Iqbal Wahyu Mustaqim; Darwati Darwati; Al Arofatus Naini; Purnama Purnama; Erina Hilmayanti; Tri Mayanti; Nurlelasari Nurlelasari; Shabarni Gaffar; Rani Maharani; Kindi Farabi; Unang Supratman; Sofa Fajriah; Mohamad Nurul Azmi; Yoshihito Shiono
Indonesian Journal of Chemistry Vol 23, No 4 (2023)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.78748

Abstract

The Aglaia species, which contains triterpenoids, is the most numerous in the Meliaceae family. The A. cucullata species, of which there are only a few known examples, has received scant research attention. This investigation aims to identify triterpenoids in an n-hexane preparation of A. cucullata stem bark and evaluate their effects against the A549 lung cancer cell line. Five dammarane-type triterpenoids were isolated from the A. cucullata trunk bark, which is (1) (20S)-20-hydroxydammar-24-en-3-one, (2) cabraleone, (3) cabralealactone, (4) eichlerianic acid, and (5) (+)-fouquierol. Their chemical structures were determined using infrared, high-resolution mass spectrometry, and nuclear magnetic resonance, as well as through data comparison of the reported compounds. Compound 1 was priorly separated from the Aglaia genus, compounds 2–4 were first isolated from the A. cucullata species, and compound 5 has been reportedly isolated from the Meliaceae family and the Aglaia genus. All substances were tested for their lethal potential against the A549 lung cancer cell type. A seco structure in the A ring of dammarane-type triterpenoid might play an important part in the lethal activity of component 4, which showed the greatest activity with an IC50 value of 32.17 µM against the A549 lung cancer cell line.
Arohynapene A Produced by Penicillium steckii JB-NW-2-1 Isolated from Avicennia marina (Forssk.) Vierh and Its Cytotoxic Activities Yeni Mulyani; Wahyu Syafriansyah; Asri Peni Wulandari; Azmi Azhari; Sari Purbaya; Aprilia Permata Sari; Galih Bayu Pratama; Fajar Fauzi Abdullah; Kindi Farabi; Unang Supratman; Yoshihito Shiono
Indonesian Journal of Chemistry Vol 24, No 2 (2024)
Publisher : Universitas Gadjah Mada

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.22146/ijc.83982

Abstract

Mangrove-associated endophytic fungi are producers of secondary metabolites in unique and diverse structures with interesting biological activities such as antiviral, antifungal, antibacterial, anti-inflammatory, and cytotoxic agents. Endophytes play an important role in the physiological activities of the host plants, influencing the improvement of resistance to stress, insects, nematodes, and diseases. In this study, arohynapene A, a polyketide compound, was successfully isolated from the mangrove-derived fungus Penicillium steckii JB-NW-2-1 obtained from mangrove plant Avicennia marina (Forssk) Vierh. The structure was determined by a spectroscopic method including IR, MS, 1D-, and 2D-NMR techniques. This compound was evaluated for cytotoxic activities using resazurin assay against four cancer cells, HeLa cervical, MCF-7 breast cancer, B16-F10 melanoma, and A549 lung adenocarcinoma. The results showed no significant activities against all cancer cells tested (IC50 > 500 µM).
Co-Authors Ace Tatang Hidayat Ahmad Darmawan Al Arofatus Naini Aprilia Permata Sari Asri Peni Wulandari Azmi Azhari Darwati Darwati Desi Harneti Putri Huspa Dewa Gede Katja Erina Hilmayanti Fajar Fauzi Abdullah Galih Bayu Pratama Gian Primahana Hersa Milawati Ida Nur Farida Ida Nurfarida Iqbal Wahyu Mustaqim Kansy Haikal Khalijah Awang Khlaijah Awang Kindi Farabi Kindi Farabi Kindi Farabi Mohamad Nurul Azmi Nur Insani Amir Nurlelasari Nurlelasari Purnama Purnama Rani Maharani Rani Maharani Rani Maharani Rani Maharani Ricson Pemimpin Hutagaol Sari Purbaya Shabarni Gaffar Sofa Fajriah Sofa Fajriah Sofa Fajriah Tjandrawati Mozef Tri Mayanti Tri Mayanti Unang Supratman Unang Supratman Unang Supratman Wahyu Syafriansyah Winda Sukmawati Yeni Mulyani