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Synthesis of α-Hydroxyisovaleric acid (Hiv) and α-Acetyloxyisovaleric Acid (Ac-Hiv), Precursors of Aureobasidin B, with Improved Yield Rani Maharani; Andi Rahim; Herdanu Rizqullah; Nur Muhammad Miftah; Ace Tatang Hidayat; Achmad Zainuddin; Nurlelasari Nurlelasari; Desi Harneti; Unang Supratman
Chimica et Natura Acta Vol 6, No 3 (2018)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (536.045 KB) | DOI: 10.24198/cna.v6.n3.20855

Abstract

α-Hydroxyisovaleric acid (Ac-Hiv) and α-acetyloxyisovaleric acid (Ac-Hiv) have been successfully synthesized through a diazotisation of amino acid using sodium nitrite with the catalyst of sulfuric acid and acetic acid, respectively. In the synthesis of Hiv, Zubia et al. (2005) mentioned that 3 equivalents of sodium nitrite for the reaction gave the hydroxy acid with a good yield. However, Cohen-Arazi et al. (2008) described that 6 equivalents of sodium nitrite resulted the highest yield. In present study, a variation of equivalents of sodium nitrite (3, 4, 5, 6 eq.) were trialed for the same method of synthesis. Through several experiments, we found that 6 equivalents of sodium nitrite were the best portion among all. This finding was applied into the synthesis of protected Hiv (Ac-Hiv) that was previously reported by Maharani et al. (2017) giving 63% yield when 3 equivalent of sodium nitrite was employed. By increasing the equivalent of sodium nitrite into 6 equivalents, the Ac-Hiv can be synthesized with an improved yield (71%).
Sintesis Tetrapeptida PSSY dengan Metode Fasa Padat Rani Maharani; Siska Mulya Octavia; Achmad Zainuddin; Ace Tatang Hidayat; Dadan Sumiarsa; Desi Harneti; Nurlelasari Nurlelasari; Unang Supratman
Chimica et Natura Acta Vol 7, No 2 (2019)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (220.512 KB) | DOI: 10.24198/cna.v7.n2.26156

Abstract

Senyawa tetrapeptida antioksidan PAGY telah berhasil diisolasi dari kulit ikan amur sturgeon dan telah berhasil disintesis berserta analog PSGY, PFFY, PAFY dan PAIY menggunakan metode SPPS. Uji antioksidan menunjukkan senyawa PSGY lebih aktif dari senyawa PAGY dan senyawa analog lainnya. Penelitian ini bertujuan untuk mensintesis senyawa tetrapeptida PSSY dengan metode SPPS, dan mengetahui aktivitas antioksidan senyawa tetrapeptida hasil sintesis dengan uji DPPH. ibuat dalam dua versi; bahasa Indonesia dan Inggris. Tetrapeptida PSSY telah berhasil disintesis menggunakan strategi SPPS dengan resin 2-klorotritilklorida sebagai padatan penyangga, gugus pelindung Fmoc, dan reagen kopling HATU/HOAt. Padatan PSSY berhasil dimurnikan menghasilkan PSSY 17 mg (13,88%). Setelah dimurnikan, PSSY dikarakterisasi dengan HR-TOF-MS yang memberikan nilai m/z [M+H] 453,2711 yang sesuai untuk PSSY. Uji aktivitas antioksidan dilakukan pada PSSY dengan nilai IC50 sebesar 7,513 mg/mL.
Senyawa Damara-20,24-dien-3-on yang beraktivitas Sitotoksis terhadap Sel Mcf-7 dari Kulit Batang Chisocheton Marcrophyllus (Meliaceae) Nurlelasari Nurlelasari; Nurabi Ferdiana; Subekti Mauluddin; Desi Harneti; Moelyono Moektiwardoyo; Rizky Abdullah; Unang Supratman; Khalijah Awang
Indonesian Journal of Applied Sciences Vol 5, No 3 (2015)
Publisher : Universitas Padjadjaran

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (7656.348 KB) | DOI: 10.24198/ijas.v5i3.15062

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AbstrakSenyawa triterpenoid damaran, damara-20,24-dien-3-on telah diisolasi dari kulit batang Chisocheton Marcrophyllus (Meliaceae). Struktur kimia kedua senyawa tersebut telah ditetapkan berdasarkan data spektroskopi dan perbandingan data spektra yang diperoleh dari literatur. Senyawa damara-20,24-dien-3-on menunjukkan aktivitas sitotoksik terhadap sel kanker payudara manusia MCF-7 dengan nilai IC50 28 mM.Kata Kunci : aktivitas sitotoksik, sel MCF-7, triterpenoid damaran, Chisocheton Marcrophyllus,  MeliaceaeAbstractDammarane triterpenoid, damara-20,24-dien-3-on has been isolated from the bark of Chisocheton Marcrophyllus (Meliaceae). Chemical Structure of compound was dtermined on the basic of spektroscopic data and comparison with those spectra data previously reported. Compound damara-20,24-dien-3-on exhibited cytotoxic activity againts MCF-7 human breast cancer cell lines with IC50 value 28 mM respectively.Kata Kunci : cytotoxic activity, MCF-7 cell, dammarane triterpenoid, Chisocheton Marcrophyllus,  Meliaceae
Cytotoxic Assay From Stem Bark Aglaia minahassae and Aglaia simplicifolia Against HeLa Cervical Cancer Cell Lines Nunung Kurniasih; Hersa Milawati; Mohamad Fajar; Rizky Abdulah; Desi Harneti Putri Huspa; Unang Supratman
Indonesian Journal of Pharmaceutical Science and Technology Suppl 1, No. 1 (2018)
Publisher : Indonesian Journal of Pharmaceutical Science and Technology

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (829.03 KB) | DOI: 10.24198/ijpst.v1i1.16116

Abstract

Cervical cancer ranks as the 2nd leading cause of female cancer in Indonesia. One of healing methods is chemotherapy, but this method still has many side e ects and also expensive treatment. Therefore, natural products discoveries need to be developed due to its important role as an alternative for anti- cancer drug. The aim of this research was to get IC50 value from methanol, n-hexane, ethyl acetate, and n-buthanol from stem bark of A. minahassae dan A. simplicifolia. Stem bark of A. minahassae (1.6 kg) and A. simplicifolia (1.1 kg) was grounded by methanol and its extract is successively extracted by n-hexane, ethyl acetate, and n-buthanol. Their extract’s cytotoxicity was then evaluated against HeLa cell lines. This research showed that A. minahassae’s most cytotoxic extract against HeLa cell lines was n-hexane (IC50 = 27.4190 μg/mL) and n-buthanol (IC50 = 4.3924 μg/mL). Meanwhile, A. sim- plicifolia most cytotoxic extract extract against HeLa cell lines was n-hexane (IC50 = 23.3098 μg/mL). Key words: A. minahassae, A. simplicifolia, cytotoxic assay, HeLa cell lines
7-HIDROKSI-6-METOKSI KUMARIN (SKOPOLETIN) DARI KULIT BATANG Chisocheton celebicus (MELIACEAE) Dewa G. Katja; Andre A. Sonda; Desi Harneti P. Huspa; Tri Mayanti; Unang Supratman
Jurnal Kimia (Journal of Chemistry) Vol. 9, No. 2 Juli 2015
Publisher : Program Studi Kimia, FMIPA, Universitas Udayana (Program of Study in Chemistry, Faculty of Mathematics and Natural Sciences, Udayana University), Bali, Indonesia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (72.382 KB) | DOI: 10.24843/JCHEM.2015.v09.i02.p18

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7-hydroxy-6-methoxy coumarin (scopoletin) has been isolated from the bark of Chisocheton celebicus (Meliacee) using several chromatographic techniques.  The chemical structure of 7-hydroxy-6-methoxy coumarin was identified on the basis of spectroscopic data including UV, IR, 1D-NMR, 2D-NMR and mass along with by comparison with those spectral data previously reported. The discovery of scopoletin from the bark C. celebicus reported for the first time in this study.
Ergosterol Peroxide and Stigmasterol from The Stembark of Aglaia simplicifolia (Meliaceae) and Their Cytotoxic against HeLa Cervical Cancer Cell Lines Nunung Kurniasih; Asep Supriadin; Desi Harneti; Rizky Abdulah; Mohamad Nurul Azmi bin Mohamad Taib; Unang Supratman
Jurnal Kimia Valensi Jurnal Kimia VALENSI Volume 7, No. 1, May 2021
Publisher : Syarif Hidayatullah State Islamic University

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.15408/jkv.v7i1.20068

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Two steroid compounds, ergosterol peroxide (1) and stigmasterol (2) have been isolated from the stembark of Aglaia simplicifolia belong to Meliaceae family. The chemical structures of 1 and 2 were identified based on spectroscopic evidence including UV, IR, 1D NMR, 2D NMR as well as mass spectra and by comparison with those previously reported spectra data. Both compounds were evaluated for their cytotoxic effects against cervical cancer HeLa cells in vitro. Compounds 1 and 2 showed cytotoxicity activity against HeLa cervical cancer cells with IC50 values of 0.80 and 26.42 µM, respectively.
Caryophyllene-Type Sesquiterpenoids from the Stembark of Aglalia harmsiana and Their Cytotoxic Activity Against MCF-7 Breast Cancer Cells Hersa Milawati; Desi Harneti; Rani Maharani; Nurlelasari Nurlelasari; Ace Tatang Hidayat; Mohamad Nurul Azmi; Yoshihito Shiono; Unang Supratman
Molekul Vol 14, No 2 (2019)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (367.192 KB) | DOI: 10.20884/1.jm.2019.14.2.543

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Sesquiterpenoid is a class of terpenoid compounds that have the most abundant diversity of structures and biological activitiesthat can be found in natural resources. Tropical plants are main source of sesquiterpenoid compounds such as Aglaiagenus belong to Meliaceae family. A. harmsianais a species from Aglaiathat only has few previous researchs.  Therefore, the purpose of this study was to isolate and determine the structure of sesquiterpenoid compounds from stem barkA. harmsianaalong withtheir cytotoxic activity against MCF-7 breast cancer cells. The isolation process begins by extracting powder from A. harmsianastembark using n-hexane, ethyl acetate and methanol. All extracts were evaluated for their cytotoxic activity against MCF-7 breast cancer cells, and n-hexane extractsshowed significant cytotoxic activitywith IC50values of 117.86 µg/mL. Therefore, n-hexane extracts were further separated and purified by various chromatographic techniquesto obtain compounds 1and 2. Compounds 1and 2were elucidated their chemical structures by spectroscopic methods includingIR, NMR, and MS as well as bycomparison of data with literatures and identified ascaryophyllene-typesesquiterpenoids, β-caryophylleneoxide (1) and senecrassidiol (2). Compounds 1and 2were submitted for cytotoxic eveluation on MCF-7 breast cancer cells and as a result, β-caryophyllene oxide (1) showed the stronger activity compared to senecrassidiol (2). These finding indicatedthat the cytotoxic activity of caryophyllene-typesesquiterpenoid areinfluenced by the presence of double bonds and configuration of methyl groups.
Two Limonoids from The Seeds of Chisocheton Macrophyllus and Their Cytotoxic Activity Against Mcf-7 Breast Cancer Cells Intan Rahmayanti; Nurlelasari Nurlelasari; Desi Harneti; Rani Maharani; Darwati Darwati; Yoshihito Shiono; Unang Supratman
Molekul Vol 16, No 2 (2021)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (4976.505 KB) | DOI: 10.20884/1.jm.2021.16.2.708

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Limonoids (tetranortriterpenoids) are triterpenoid compounds that lose four terminals in their structural framework. These compounds have a wide variety of structures and interesting activities including anti-inflammatory, anti-cancer, anti-tumor and anti-malarial properties. The purpose of this study was to find limonoid compounds from the Indonesian Chisocheton plant, and one of which is Chisocheton macrophyllus. The dried and powdered seeds of C. macrophyllus (4.5 kg) were extracted with methanol and partitioned successively with n-hexane, ethyl acetate and n-butanol. Evaporation of each extract resulted in the crude extracts of n-hexane (346.6 g), ethyl acetate (60.8 g) and n-butanol (14.6 g). The n-hexane fraction was subjected to a silica gel vacuum-liquid chromatography (VLC) column packed with silica gel 60 using gradient of n-hexane, ethyl acetate and methanol (10% stepwise) to afford thirteen fractions (A-M). Fraction F (4.4 g) was subjected to silica gel column chromatography using gradient of n-hexane and ethyl acetate (5% stepwise). Subfraction F5 (1.2 g) was chromatographed on a column of silica gel eluted with n-hexane: CH2Cl2: EtOAc (2:7.5:0.5) to give compound 1 (19.7 mg) and fraction H (1.8 g) was subjected to silica gel column chromatography using gradient of n-hexane and ethyl acetate (5% stepwise) as eluting solvent to give 2 (12.0 mg). Chemical structures of 1 and 2 were elucidated by spectroscopic methods and determined as 6α-acetoxyepoxyazadiradione (1) and Dysobinin(2). Dysobinin (2) showed weak cytotoxic activity against MCF-7 breast cancer cells with an IC50 value of 228.15 μM
Four Flavan-3-ol Compounds From The Stembark of Chisocheton balansae C.DC. (MELIACEAE) Unang Supratman; Mohamad Fajar; Supriatno Salam; Rani Maharani; Desi Harneti; Nur;lelasari Nurlelasari; Dewa Gede Katja; Agus Safari; Mohamad Nurul Azmi
Molekul Vol 16, No 1 (2021)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (3611.573 KB) | DOI: 10.20884/1.jm.2021.16.1.642

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Chisocheton balansae C.DC., is one of the Meliaceae family plants which is the endemic plants from Soputan Mountain, North Sulawesi, Indonesia. This study was aimed to determine the chemical structure of flavan-3-ol compounds from ethyl acetate extract of C. balansae C.DC stembark. Dried powder of C. balansae C.DC stem bark was extracted consecutively with n-hexane, ethyl acetate, and methanol solvents. Four flavan-3-ol compounds, named catechin (1), epicatechin (2), epigallocatechin-3-O-gallate (3), and epicatechin-3-O-gallate (4) were successfully isolated from ethyl acetate extract. The chemical structure of these isolates was determined by spectroscopic methods (1H-NMR, 13C-NMR, DEPT, and 2D-NMR) and comparison with previous reported spectral data. These compounds are first time reported from this plant.
A Cytotoxic Rocaglate Compound from The Stembark of Aglaia argentea (Meliaceae) Ace Tatang Hidayat; Kindi Farabi; Desi Harneti; Nurlelasari Nurlelasari; Rani Maharani; Tri Mayanti; Unang Supratman; Yoshihito Shiono
Molekul Vol 12, No 2 (2017)
Publisher : Universitas Jenderal Soedirman

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (86.011 KB) | DOI: 10.20884/1.jm.2017.12.2.361

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The Aglaia genus belong to Meliceae family is unique plant species because the presence of rocaglate and rocaglamide which is so far isolated only from Aglaia genus, indicate that type of this compound as a chemical marker for the genus of Aglaia. This type of compound known to have strong activity, such as insecticide and cytotoxic. This study describe the isolation, structure elucidation, and cytotoxic activity of an isolated rocaglate compound. Dried stembark of A. argentea extracted with methanol and partition between n-hexane, ethyl acetate, and n-butanol, respectively The extracts were tested against P-388 murine leukemia cells and the ethyl acetat showed strongest activity with IC50 value of 15.5 mg/mL. The ethyl acetate then was separated and purified with chromatography technique to obtain isolated compound 1. The chemical structure of isolated  compounds were elucidated by spectroscopic methods including one and two-dimensional NMR as well as high-resolution mass spectrometric analysis and identified as a methyl rocaglate. Compound  1 showed strong cytotoxic activity with an IC50 value of < 0.1 μg/mL.
Co-Authors Ace Tatang Hidayat Ace Tatang Hidayat Ace Tatang Hidayat Achmad Zainuddin Ade Zuhrotun Agus Safari Agus Safari Agus Safari Agus Safari Al Arofatus Naini Anastasya Firdausi Andi Rahim Andre A. Sonda Anjari, Intan Hawina Annisa Abdiwijaya Qaromah Aprilia Permata Sari Asep Supriadin Asri Peni Wulandari Asri Peni Wulandari, Asri Peni Azmi Azhari, Azmi Azmi, Mohamad Nurul Celcius Waranmaselembun Christina Marpaung Dadan Sumiarsa Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati, Darwati, Darwati Dessy Yulyani Kurnia Dewa Gede Katja Dewa Gede Katja Dini Oktaviani DUDI RUNADI Dudi Runadi Erina Hilmayanti Euis Julaeha Euis Julaeha Evan Hadrian Faizah Maira Fajar, Mohamad Farabi, Kindi Ferry Ferdiansyah Sofian, Ferry Ferdiansyah Ghina Izdihar Gunawan, Latifah Hadi Kuncoro Harizon Harizon Herdanu Rizqullah Hersa Milawati Hersa Milawati Hersa Milawati Hideo Hayashi Hideo Hayashi Hideo Hayashi Hilmayanti, Erina Hutagaol, Ricson Pemimpin Ida Nur Farida Ida Nurfarida Ihsan Rahadian Intan Hawina Anjari Intan Rahmayanti Iqbal Wahyu Mustaqim Jamaludin Al-Anshori Julinton Sianturi Julinton Sianturi Kansy Haikal Karen Kezia Lolowang Khalijah Awang Khalijah Awang Khalijah Awang Khalijah Awang Khalijah Awang Khalijah Awang Khalijah Awang Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Mayshah Purnamasari Milawati, Hersa Moelyono Moektiwardoyo Mohamad Fajar Mohamad Fajar Mohamad Nurul Azmi Mohamad Nurul Azmi Mohamad Nurul Azmi Mohamad Nurul Azmi Mohamad Nurul Azmi bin Mohamad Taib Muchlis, Handi Nugraha Muhamad Nurul Azmi Muhammad Hanafi Muhammad Hanafi Mustaqim, Iqbal Wahyu Mustofa, Hidayat Nurul Nafiah, Mohamad Azlan Naini, Al Arofatus Nulelasari Nurlelasari Nunung Kurniasih Nunung Kurniasih Nunung Kurniasih, Nunung Nur Muhammad Miftah Nurabi Ferdiana Nurlelasari Nurlelasari Nurlelasari Nurlelasari Nurlelasari Nurlelasari Pratama, Galih Bayu Primahana, Gian Purbaya, Sari Purnama Purnama Purnama Purnama Purnama Purnama Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Rani Maharani Ricson Pemimpin Hutagaol Risyandi Anwar Rizky Abdulah Rizky Abdullah Ronauli Fitriana Safri Ishmayana Salam, Supriatno Sari, Aprilia Permata Shabarni Gaffar Shiono, Yoshihito Sianturi, Julinton Siska Mulya Octavia Siska Mulya Octavia Siti Hani Pratiwi Sofa Fajriah Sofa Fajriah Sofa Fajriah Srikandi, Srikandi Subekti Mauluddin Supriatno Salam Tiara Prima Amalya Tjandrawati Mozef Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Unang Supratman Vidia Afina Nuraini Winda Sukmawati Winda Sukmawati Yeni Mulyani Yoshihito shiono Yoshihito Shiono Yoshihito Shiono Yoshihito Shiono Yoshihito Shiono Yoshihito Shiono Yoshihito Shiono Yoshihito Shiono