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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

Author-ID : 2589836

Biochemistry, Genetics & Molecular Biology Chemical Engineering, Chemistry & Bioengineering Chemistry Materials Science & Nanotechnology

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Articles

Dammarane-Type Triterpenoids from The Stembark of Aglaia argentea (Meliaceae) Ace Tatang Hidayat; Kindi Farabi; Ida Nur Farida; Kansy Haikal; Nurlelasari Nurlelasari; Desi Harneti Putri Huspa; Rani Maharani; Unang Supratman; Yoshihito Shiono
Jurnal Kimia Valensi Jurnal Kimia VALENSI Volume 4, No. 1, Mei 2018
Publisher : Syarif Hidayatullah State Islamic University

Two dammarane-type triterpenoids, 20S,24S-epoxy-3α,25-dihydroxydammarane (1) and 3α-acetyl-20S,24S-epoxy-3α,25-dihydroxydammarane (2), have been isolated from the stembark of Aglaia argentea. The chemical structure of compounds (1 and 2) were identified by spectroscopic evidences including UV, IR, 1D-NMR, 2D-NMR and MS as well as by comparing with previously reported spectral data. Those compounds were isolated from this plant for first time. Compounds (1 and 2) showed cytotoxic activity against P-388 murine leukemia cells with IC50 values of 23.96 and 8.14 mM, respectively.DOI:http://dx.doi.org/10.15408/jkv.v4i1.7065

Steroids from The Stem Bark of Dysoxylum nutans (Meliaceae) and Their Cytotoxic Effect Against MCF-7 Breast Cancer Cell Lines Tri Mayanti; Nur Insani Amir; Dewa Gede Katja; Sofa Fajriah; Ahmad Darmawan; Unang Supratman; Khlaijah Awang; Yoshihito Shiono
Jurnal Kimia Valensi Jurnal Kimia VALENSI Volume 6, No. 2, November 2020
Publisher : Syarif Hidayatullah State Islamic University

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.15408/jkv.v6i2.15976

Three steroids, 3α-hydroxystigmast-5(6), 22-diene-7-one (1), stigmasterol (2) and 3-hydroxy-7β-methoxystigmast-5(6)-ene (3), were isolated from the stem bark of Dysoxylum nutans. The chemical structures were identified by spectroscopic data, which includes IR, 1D-NMR, 2D-NMR, and HR-TOFMS as well as by comparing previously reported spectral data. Compounds 1-3 were tested for cytotoxic effect against MCF-7 breast cancer cell lines and compound 1 showed the strongest cytotoxic activity with an IC50 value of 20.13 ± 0.06 μM.

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

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

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.

Cholestan Steroids from The Stem Bark of Aglaia angustifolia Miq and Their Cytotoxic Activity against MCF-7 Breast Cancer Cell Lines Ricson Pemimpin Hutagaol; Tjandrawati Mozef; Sofa Fajriah; Gian Primahana; Unang Supratman; Desi Harneti; Ace Tatang Hidayat; Khalijah Awang; Yoshihito Shiono
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

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.

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

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

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

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