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SINTESIS PREKURSOR SENYAWA BEAUVERICIN, ASAM (2R)-ASETILOKSIISOVALERAT Maharani, Rani; Taufiqqurahman, Taufiqqurahman; Puspitasari, Dina
Chimica et Natura Acta Vol 3, No 3 (2015)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (382.742 KB) | DOI: 10.24198/cna.v3.n3.9217

Abstract

Beauvericin merupakan heksadepsipeptida siklik yang diproduksi oleh berbagai jamur seperti Beauveria bassiana dan Fussarium spp. Penelitian mengenai sintesis senyawa beauvericin telah dilakukan melalui media mikrobiologi, namun sintesis dengan metode sintesis peptida masih belum banyak dilaporkan. Sedikitnya laporan mengenai sintesis senyawa beauvericin disebabkan sulitnya akses terhadap pengadaan material sintesis atau prekursor senyawa yang bersangkutan.Prekursor dari senyawa beauvericin adalah asam amino N-metilfenilalanin dan asam hidroksi isovalerat. Dalam kaitannya dengan sintesis total peptida dalam fase padat yang akan dilakukan, asam hidroksi isovalerat (Hiv) akan sulit ditambahkan ke dalam resin, sehingga senyawa ini harus ditambahkan kedalam resin dalam bentuk depsidipeptida, Fmoc-MePhe-Hiv.Sintesis depsidipeptida ini merupakan rangkaian 4 tahap reaksi, yakni, diazotisasi-perlindungan t-Bu-pelepasan asetiloksi-kopling.Dalam penelitian ini,tahap diazotisasi akan dilaporkan. Asam (2R)-asetiloksiisovalerat disintesis dari D-valin melalui reaksi pembentukan garam diazonium dengan penambahan NaNO2 dan asam asetat.Proses sintesis dikontrol dengan kromatografi lapis dan dimurnikan dengan metode kromatografi kolom terbuka. Produk sintesis dikarakterisasi dengan berbagai teknik spektroskopi meliputi spektrofotometer inframerah, spektroskopi massa (LC-MS),1H-NMR dan 13C-NMR. Senyawa asam (2R)-asetiloksiisovalerat diperoleh dengan rendemen 62,7%.
Sintesis Senyawa 5-(4-klorobenzilidena)imidazolina-2,4-dion Naufal, Muhammad; Maharani, Rani; Wiani, Ika
Chimica et Natura Acta Vol 5, No 1 (2017)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (619.085 KB) | DOI: 10.24198/cna.v5.n1.12820

Abstract

Senyawa benzalhidantoin atau 5-benzilidena-imidazolidina-2,4-dion (3) merupakan senyawa yang dapat diisolasi dari spons merah laut Laxosubrites sp. dan memiliki aktivitas antikejang serta antikanker prostat PC-3M. Senyawa tersebut sudah disintesis sejak beberapa dekade yang lalu dan banyak diteliti bioaktivitasnya, baik di bidang kesehatan maupun pertanian. Penelitian di bidang kesehatan, contohnya sebagai agen antikonvulsan, antivirus, inhibitor EGFR dan antiproliferasi sel A431, antikanker sel HepG2, antimetastatik sel kanker PC-3M, inhibitor enzim tirosinase dan pembentukan melanin serta di bidang pertanian sebagai herbisida dan fungisida. Tujuan dari penelitian ini adalah mensintesis senyawa 5-(4-klorobenzilidena)-imidazolidina-2,4-dion (7) melalui reaksi kondensasi antara hidantoin (1) dengan 4-klorobenzaldehida (2) menggunakan pereaksi natrium bikarbonat dalam etanol, dan etanolamina sebagai katalis basa (metode Eli Lily). Hidantoin (1) dan 4-klorobenzaldehida (2) sebagai senyawa prekursor diperoleh secara komersil. Sintesis dilakukan dengan cara mereaksikan senyawa hidantoin (1) dan 4-klorobenzaldehida (2) secara stokiometri dengan katalis basa etanolamina dalam etanol dan air (modifikasi metode Eli Lily) dan direfluks selama 6 jam. Senyawa hasil sintesis dimurnikan dengan cara rekristalisasi dari etanol panas, diperoleh kristal putih berbentuk jarum 5-(4-klorobenzilidena)-imidazolidina-2,4-dion (7) dengan rendemen 12%. Senyawa tersebut dianalisis dengan menggunakan KLT silika gel GF254, aseton-heksana (1:1 v/v) memberikan harga Rf = 0,625 untuk senyawa (7) dengan titik leleh (TL)=292-294°C (TL lit.=294-296°C). Selanjutnya, senyawa tersebut diidentifikasi strukturnya menggunakan spektroskopi UV, IR, HR-TOF-MS ES+, 1H-NMR dan 13C-NMR, yang menunjukkan konsistensi senyawa hasil sintesis dengan senyawa 5-(4-klorobenzilidena)-imidazolidina-2,4-dion (7).
RESOLUTION OF A RACEMIC ISOLEUCINE MIXTURE BY USING METHYL L-MANDELATE Maharani, Rani; Hidayat, Ace Tatang; Sumiarsa, Dadan; Zainuddin, Achmad; Hidayat, Ika Wiani
Chimica et Natura Acta Vol 4, No 3 (2016)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (237.517 KB) | DOI: 10.24198/cna.v4.n3.10991

Abstract

A methyl ester of L-mandelic acid was found to be an effective resolving agent for resolution of commercial DL-isoleucine. The resolution was based on Steglich esterification between methyl L-mandelate and Boc-DL-isoleucine. The two resolved isomers were easily separated by using a conventional flash-column chromatography, giving quantitatively good yields. Unfortunately, the methyl L-mandelate was found to be ineffective to resolve four stereoisomers of Fmoc- isoleucine.
Bioactivity Formulation Of Leaf Extract Of Kalanchoe pinnata And Seed Of Azadirachta indica Against Spodoptera litura Paramita, Hedi; Puspasari, Lindung Tri; Maharani, Rani; Supratman, Unang; Hidayat, Yusup; Meliansyah, Rika; Dono, Danar
CROPSAVER - Journal of Plant Protection Vol 1, No 1 (2018)
Publisher : Departemen Hama dan Penyakit Tumbuhan Fakultas Pertanian Universitas Padjadjaran

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

Abstract

The aim of this research is to know the most effective concentration of liquid formulation of Kalanchoe pinnata leaf extract 50 EC and Azadirachta indica seed extract 50 EC against S. litura. The experiment was conducted at the Laboratory of Pesticides and Enviromental Toxicology, Department of Plant Pests and Diseases, Faculty of Agriculture, Universitas Padjadjaran. The concentration were tested of each formulation were 1%, 2%, 3 %, 4%,and control.  The experiment arranged in completely randomized design (CRD) and replicated three times. The results showed that the formulation of A. indica seed extract 50 EC at concentration of 2%, 3%, and 4% effective against S. Litura larvae with mortality of 76.7%, 86.7, and 93.3%  This formulation also causing a decrease in feeding activity, weight, and lenghten the development time of S.litura larvae. Unlike the case with liquid formulations of K. pinnata 50 EC extract which was less toxic and did not show significant differences in feed intake, weight of larvae, and development time of larvae compared control treatment.                Keywords: Toxicity, mortality, growth dearragement, botanical insecticide.
Bioactivity Formulation Of Leaf Extract Of Kalanchoe pinnata And Seed Of Azadirachta indica Against Spodoptera litura Hedi Paramita; Lindung Tri Puspasari; Yusup Hidayat; Rika Meliansyah; Danar Dono; Rani Maharani; Unang Supratman
CROPSAVER Vol 1, No 1 (2018)
Publisher : Departemen Hama dan Penyakit Tumbuhan Fakultas Pertanian Universitas Padjadjaran

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (280.565 KB) | DOI: 10.24198/cs.v1i1.16995

Abstract

The aim of this research is to know the most effective concentration of liquid formulation of Kalanchoe pinnata leaf extract 50 EC and Azadirachta indica seed extract 50 EC against S. litura. The experiment was conducted at the Laboratory of Pesticides and Enviromental Toxicology, Department of Plant Pests and Diseases, Faculty of Agriculture, Universitas Padjadjaran. The concentration were tested of each formulation were 1%, 2%, 3 %, 4%,and control.  The experiment arranged in completely randomized design (CRD) and replicated three times. The results showed that the formulation of A. indica seed extract 50 EC at concentration of 2%, 3%, and 4% effective against S. Litura larvae with mortality of 76.7%, 86.7, and 93.3%  This formulation also causing a decrease in feeding activity, weight, and lenghten the development time of S.litura larvae. Unlike the case with liquid formulations of K. pinnata 50 EC extract which was less toxic and did not show significant differences in feed intake, weight of larvae, and development time of larvae compared control treatment.                Keywords: Toxicity, mortality, growth dearragement, botanical insecticide.
Cytotoxic Steroids From The Stembak of Chisocheton celebicus KOORD Dewa Gede Katja; Desi Harneti; Tri Mayanti; Nurlelasari Nurlelasari; Rani Maharani; Yoshihito Shiono; Unang Supratman
Jurnal Kimia Valensi Jurnal Kimia VALENSI Volume 5, No. 2, November 2019
Publisher : Syarif Hidayatullah State Islamic University

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (514.577 KB) | DOI: 10.15408/jkv.v5i2.12132

Abstract

In the course of our continuing search for anticancer compounds from Chisocheton species, three steroids, stigmast-5-en-3β-ol (1), stigmast-5-en-3β-ol-3-O-β-D-glucopyranoside (2) and stigmast-5,22-dien-3β-ol-3-O-β-D-glucopyranoside (3), were obtained from the stembark of Chisocheton celebicus. The structures of compound 1-3 were identified with spectroscopic data including IR, 1D-NMR, 2D-NMR and TOF-MS, as well as by comparing with those spectral data previously. Compounds 1-3, were evaluated for their cytotoxic effects against P-388 murine leukemia cells and displayed the cytotoxicity activity with IC50 values of 12.45 ± 0.050, 52.27 ± 0.031 and 62.52 ± 0.076 µg/mL, respectively.
Solid-phase Synthesis of Tetrapeptide on 2-Chlorotrityl Chloride Resin by Using Benzotriazol-1-yl-oxytripyrrolidinophosphonium Hexafluorophosphate as Coupling Reagent Rani Maharani; Nuruzzahra Ammatillah; Gunawan Gunawan; Ace Tatang Hidayat
Jurnal Kimia Valensi Jurnal Kimia VALENSI Volume 2, No. 2, November 2016
Publisher : Syarif Hidayatullah State Islamic University

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.15408/jkv.v2i2.4055

Abstract

Tetrapeptide, OH-Pro-Ala-Gly-Tyr-NH2, was successfully synthesised on 2-chlorotrityl chloride resin by taking advantage of PyBOP (benzotriazol-1-yl-oxytripyrrolidinophosphonium hexafluorophosphate) as coupling reagent. The selection of the peptide as the target of synthesis was due to its interesting bioactivity as antioxidant. The synthesis was undertaken with Fmoc strategy, where Fmoc-proline was added onto the resin at the first place. It is known from the literature that proline can resist from rasemisation when  it was attached on the resin at the first time. Fmoc deprotection step was carried out by employing 20% piperidine in DMF and the reaction mixture was shaken for 30 minutes. Once the proline attached, the next step was to attach amino acids, alanine (Ala), glycine (Gly) and tyrosine(Tyr), subsequently onto the resin until tetrapeptidyl resin was constructed on the resin.  Hydroxyl group of Tyr was protected with t-butyl, which is TFA-labiled. Coupling reaction was undertaken by mixing the amino acid and PyBOP in a mixture of dichloromethane and DMF (1:1) and in the presence of basic DIPEA. Resin cleavage step was carried out by using 95% TFA in water, where t-butyl protecting group on the side chain of Tyr was cleaved at the same time. The analytical RP-HPLC of the final product showed a single peak at 21.9 minutes (20-90% of acetonitrile in water with 0.1% of TFA during 30 minutes), indicating that each coupling has given a good coupling performance and resulting in a pure product. The desired product showed the correct molecular weight with m/z 407.2 [M+H]+ and 429.2 [M+Na]. DOI: http://dx.doi.org/10.15408/jkv.v0i0.4055
Upaya Optimasi Sintesis Pentapeptida Leu-Ala-Asn-Ala-Lys dengan Pengurangan Nilai Loading Resin Rani Maharani; Dessy Yulyani Kurnia; Ace Tatang Hidayat; Jamaludin Al-Anshori; Dadan Sumiarsa; Desi Harneti; Nurlelasari Nurlelasari
Chimica et Natura Acta Vol 8, No 1 (2020)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.24198/cna.v8.n1.28671

Abstract

SCAP1 (Saccostrea Cucullata Antioxidant Peptide 1) dengan urutan asam amino LANAK (Leu-Ala-Asn-Ala-Lys) merupakan pentapeptida yang diisolasi dari hidrolisat tiram dan diketahui memiliki aktivitas antioksidan dengan scavenging radikal DPPH sebesar 83,79 ± 0,53%. Peptida ini telah berhasil dibuat dengan metode sintesis peptida fase padat dengan persen rendemen 8,28%. Rendahnya persen rendemen yang diperoleh disebabkan karena adanya dua residu Ala serta 1 residu Asn yang dapat menyebabkan agregasi. Nilai loading resin yang terlalu besar juga menjadi salah satu penyebab terbentuknya agregasi karena loading resin dilakukan selama 15 jam. Penelitian ini bertujuan untuk menyintesis senyawa SCAP1 dengan pengurangan nilai loading resin. Untuk meningkatkan persen rendemen dari penelitian sebelumnya, pada penelitian ini dilakukan optimasi sintesis terhadap SCAP1. Sintesis dilakukan dengan pengurangan nilai loading resin dengan cara mempersingkat waktu loading resin menjadi 4 jam. Senyawa SCAP1 hasil sintesis memiliki massa crude sebesar 119,5 mg dan berhasil dimurnikan menggunakan RP-HPLC preparatif dengan massa murni 10,6 mg dan rendemen 16%. Penelitian ini menunjukkan bahwa pengurangan loading resin meningkatkan rendemen SCAP1 dari 8,28% menjadi 16%.
RESOLUTION OF A RACEMIC ISOLEUCINE MIXTURE BY USING METHYL L-MANDELATE Rani Maharani; Ace Tatang Hidayat; Dadan Sumiarsa; Achmad Zainuddin; Ika Wiani Hidayat
Chimica et Natura Acta Vol 4, No 3 (2016)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | Full PDF (237.517 KB) | DOI: 10.24198/cna.v4.n3.10991

Abstract

A methyl ester of L-mandelic acid was found to be an effective resolving agent for resolution of commercial DL-isoleucine. The resolution was based on Steglich esterification between methyl L-mandelate and Boc-DL-isoleucine. The two resolved isomers were easily separated by using a conventional flash-column chromatography, giving quantitatively good yields. Unfortunately, the methyl L-mandelate was found to be ineffective to resolve four stereoisomers of Fmoc- isoleucine.
7-hidroksi-6-metoksi Kumarin (Skopoletin) dari Ekstrak Metanol Kulit Batang Chisocheton cumingianus (Meliaceae) Nurlelasari Nurlelasari; Tiara Prima Amalya; Euis Julaeha; Desi Harneti P. Huspa; Rani Maharani; Darwati Darwati; Unang Supratman
Chimica et Natura Acta Vol 8, No 2 (2020)
Publisher : Departemen Kimia

Show Abstract | Download Original | Original Source | Check in Google Scholar | DOI: 10.24198/cna.v8.n2.29563

Abstract

Keanekaragaman hayati hutan tropis Indonesia merupakan sumber senyawa organik bahan alam seperti limonoid, triterpenoid, seskuiterpenoid, steroid, serta senyawa-senyawa fenolik yang struktur molekulnya beragam dan menunjukkan bioaktivitas yang menarik. Salah satu senyawa yang menarik diteliti adalah senyawa fenolik karena memiliki keberagaman baik fungsi maupun strukturnya. Senyawa fenolik pada tumbuhan dapat dijumpai pada famili Meliaceae. Genus Chisocheton merupakan salah satu tumbuhan dari famili Meliaceae yang memiliki sekitar 53 spesies, diantaranya adalah Chisocheton cumingianus. Chisocheton yang telah banyak diteliti memiliki aktivitas antikanker, antimalaria, antivirus, anti-oksidan, anti-inflamasi, anti-insektisida dan antimikroba. Senyawa-senyawa yang telah banyak diisolasi meliputi limonoid, triterpenoid, dan steroid. Pada paper ini akan disampaikan elusidasi struktur senyawa skopoletin dari kulit batang C. cumingianus. Senyawa skopoletin ini diperoleh dari serbuk kulit batang C. cumingianus yang diekstraksi dengan metode maserasi menggunakan n-heksana, etil asetat, dan metanol yang selanjutnya dipekatkan hingga diperoleh ekstrak pekat. Ekstrak metanol dipisahkan serta dimurnikan dengan berbagai teknik kromatografi hingga diperoleh senyawa skopoletin yang berwarna kuning pucat  (9,1mg). Struktur molekul senyawa hasil isolasi ditentukan dengan metode spektroskopi IR, 1H-NMR, 13C-NMR, dan DEPT serta dibandingkan dengan literatur, maka disimpulkan bahwa isolat F4 merupakan senyawa 7-hidroksi-6-metoksi kumarin (skopoletin).
Co-Authors 10060321019, Dinah Shafira Abasi Ace Tatang Hidayat Achmad Zainuddin Achmad Zainuddin Adhitthana Wiguna Agus Safari Agus Safari Al Arofatus Naini Al Arofatus Naini Alhakim, Ibrahim Almas Widyana Anastasya Firdausi Andi Rahim Aprilia Permata Sari Ari Hardianto Ari Tri Wanodyo Handayani Ariq, Muhammad Ayu Andini Azmi, Mohamad Nurul Celcius Waranmaselembun Dadan Sumiarsa Danar Dono Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati Darwati, Darwati Deden Indra Dinata, Deden Indra Desak Made Malini Desi Harnet Desi Harneti Desi Harneti Putri Huspa Dessy Yulyani Kurnia Dewa Gede Katja Dina Puspitasari Dini Oktaviani DUDI RUNADI Dwi Maulidani Fadhlan Eka Fitri Yanti, Eka Fitri Erina Hilmayanti Erina Hilmayanti Euis Julaeha Euis Julaeha Evan Hadrian Fadillah, Yusuf Fahmi Faturahman Fajar Fauzi Abdullah Fajar Fauzi Abdullah Farabi, Kindi Ferry Ferdiansyah Sofian, Ferry Ferdiansyah Ghina Izdihar Gunawan Gunawan Gunawan, Latifah Hedi Paramita Herdanu Rizqullah Hersa Milawati Hidayatunnisa, Nurul Hikmat Kasmara Hilmayanti, Erina Ika Wiani Intan Rahmayanti Iqbal Wahyu Mustaqim Irwandaru Dananjaya Jamaludin Al-Anshori Khalijah Awang Khalijah Awang Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kindi Farabi Kiswaluyo . Kusumawardhani, Ayuning Dyah Lindung Tri Puspasari Madihah Madihah Magdalena, Ina Melanie Melanie Mohamad Nurul Azmi Mohamad Nurul Azmi Muchlis, Handi Nugraha Muhamad Naufal Muhamad Nurul Azmi Muhamad Nurul Azmi Muhammad Hanafi Muhammad Hanafi Muhammad Hanafi Muhammad Luthfi Muhammad Naufal, Muhammad Muhammad Rijal Alfian Mustaqim, Iqbal Wahyu Mustofa, Hidayat Nurul Muttaqin, Fauzan Zein N, Gilang Kusuma Nadya Thufaila Nafiah, Mohamad Azlan Naini, Al Arofatus Nety Kurniaty Nur Muhammad Miftah Nurlelasari Nurlelasari Nuruzzahra Ammatillah Paramita, Hedi Puji Rahayu Purnama Purnama Purnama Purnama R. Arif Malik Ramadhan Revan Hardiawan Rika Meliansyah Risyandi Anwar Robbaniyyah, Nuzla Af'idatur Ronauli Fitriana Ropidoh, Siti Safri Ishmayana Samuel San Parulian Selly Marita Serlin Sepriyanti Dohare Shabarni Gaffar Shiono, Yoshihito Siska Elisahbet Sinaga Sofa Fajriah Sofa Fajriah Sofa Fajriah Sofa Fajriah Sofa Fajriah Supriatno Salam Taufiqqurahman, Taufiqqurahman Tharysa Rizqika Putri Tiara Prima Amalya Tri Mayanti Tri Mayanti Tri Mayanti Tri Mayanti Ulfa, Kurnia UMAN SUHERMAN, UMAN Unang Supratman Urfa, Salsa Rojana Vita Novianti Wawan Hermawan Wawan Hermawan Winda Sukmawati Winda Sukmawati Yoshihito Shiono Yoshihito Shiono Yoshihito Shiono Yoshihito Shiono Yoshihito Shiono Yoshihito Shiono Yoshihito Shiono Yoshihito Shiono Yusuf Hidayat Yusuf Hidayat Yusup Hidayat Yusup Hidayat