ISOLASI SENYAWA TRITERPENOID DARI EKSTRAK ASETON DAUN Garcinia Celebica L DAN UJI AKTIVITAS ANTIKANKER PAYUDARA (MCF-7)

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ISOLASI SENYAWA TRITERPENOID DARI EKSTRAK ASETON DAUN Garcinia Celebica L DAN UJI AKTIVITAS ANTIKANKER PAYUDARA (MCF-7) ISOLASI SENYAWA TRITERPENOID DARI EKSTRAK ASETON DAUN Garcinia celebica L DAN UJI AKTIVITAS ANTIKANKER PAYUDARA (MCF-7) SKRIPSI AMBAR ILAFAH RAMADHAN PROGRAM STUDI KIMIA FAKULTAS SAINS DAN TEKNOLOGI UNIVERSITAS ISLAM NEGERI SYARIF HIDAYATULLAH JAKARTA 2018 M / 1440 H ISOLASI SENYAWA TRITERPENOID DARI EKSTRAK ASETON DAUN Garcinia celebica L DAN UJI AKTIVITAS ANTIKANKER PAYUDARA (MCF-7) SKRIPSI Sebagai Salah Satu Syarat Memperoleh Gelar Sarjana Sains Program Studi Kimia Fakultas Sains Dan Teknologi Universitas Islam Negeri Syarif Hidayatullah Jakarta Oleh: AMBAR ILAFAH RAMADHAN 11140960000063 PROGRAM STUDI KIMIA FAKULTAS SAINS DAN TEKNOLOGI UNIVERSITAS ISLAM NEGERI SYARIF HIDAYATULLAH JAKARTA 2018 M / 1440 H ABSTRAK AMBAR ILAFAH RAMADHAN. Isolasi Senyawa Triterpenoid dari Ekstrak Aseton Daun Garcinia celebica L dan Uji Aktivitas Antikanker Payudara (MCF-7). Dibimbing oleh SRI HARTATI dan SITI NURBAYTI. Tumbuhan Garcinia celebica merupakan salah satu dari sekitar 450 spesies Garcinia yang mengandung senyawa triterpenoid, depsidon, xanton, dan benzofenon yang berpotensi sebagai terapi kanker. Uji pendahuluan antikanker payudara (MCF-7) terhadap ekstrak aseton daun G .celebica telah dilakukan dengan nilai aktivitas sebesar 94,36% dalam konsentrasi 200 µg/mL dan 83,12% dalam konsentrasi 50 µg/mL. Tujuan penelitian ini adalah mengisolasi dan mengidentifikasi struktur metabolit sekunder dari ekstrak aseton daun G. celebica serta aktivitas antikankernya. Tahapan yang dilakukan adalah fraksinasi menggunakan metode kromatografi, identifikasi struktur dengan spektroskopi UV- Vis, FTIR, LCMS, dan NMR serta uji aktivitas antikanker payudara (MCF-7) dengan metode MTT assays. GC-2 yang diperoleh berupa gum putih sebanyak 20 mg dari 47,7 g ekstrak kasar. Hasil analisis UV-Vis menunjukkan adanya gugus kromofor C=C (λmax 222 nm) dan C=O (λmax 272 nm). Analisis FTIR menunjukkan vibrasi dari gugus fungsi O-H karboksilat (3378,47 cm-1), C-O (1262,46 cm-1), C=O (1686,82 cm-1) dan C=C (1640,33 cm-1). Analisis LCMS menghasilkan puncak + + dominan m/z [M H] 453,4 (BM=452) dengan rumus molekul C30H44O3 diduga merupakan senyawa asam (24E)-3-okso-17,14-friedolanosta-8(9),14(15),24(25)- trien-26-oat. Analisis 1H NMR dan 13C NMR menunjukkan sinyal khas triterpenoid yaitu C=O keton (δc 211,2 C-3), -C=O karbonil karboksilat (δc 173,2 C-26), tiga C=C (δc 145,7 (C-14), 145,5 (C-25), 144,2 (C-9), 126,5 (C-25), 125,0 (C-8) dan 120,3 (C-15), 7 sinyal metil, 2 metin, 9 metilen dan 4 karbon kuartener. Hasil uji antikanker menunjukkan GC-2 memiliki aktivitas antikanker payudara yang sangat kuat dengan nilai IC50 sebesar 24,97 µg/mL. Kata kunci : Aktivitas antikanker, Garcinia celebica, isolasi, karakterisasi ABSTRACT AMBAR ILAFAH RAMADHAN. Isolation of Triterpenoid Compounds from Garcinia celebica L Leaf Acetone Extract and Breast Anticancer (MCF-7) Activity Test. Advisor by SRI HARTATI and SITI SURBAYTI. The Garcinia celebica plant is one of about 450 Garcinia species containing triterpenoid compounds, depsidone, xanthone and benzophenone which have the potential as cancer therapy. Preliminary test of breast anticancer (MCF-7) on the acetone extract of G .celebica leaf was carried out with an activity value of 94.36% in a concentration of 200 µg / mL and 83.12% in a concentration of 50 µg / mL. The purpose of this study was to isolate and identify secondary metabolite structure of G. celebica acetone extract and its anticancer activity. The steps taken were fractionation using chromatography method, structural identification with UV-Vis spectroscopy, FTIR, LCMS, and NMR as well as breast anticancer (MCF-7) activity test using MTT assays method. GC-2 obtained in the form of 20 mg of white gum from 47.7 g of crude extract. UV-Vis analysis shows that there is a chromophore C=C (λmax 222 nm) and C=O (λmax 272 nm). FTIR analysis showed the vibration of OH carboxylic functional groups (3.378,47 cm-1), C-O (1.262,46 cm-1), C=O (1.686,82 cm-1), and C=C (1.640,33 cm-1). The molecular formula C30H44O3 thought to be an acid compound (24E)-3-oxo-17,14-friedolanosta- 8(9),14(15),24(25)-trien-26-oat. The 1H NMR and 13C NMR analysis showed a typical triterpenoid signal, namely C=O ketone (δc 211,2 C-3), -C=O carboxylic carbonyl (δc 173,2 C-26), three C = C (δc 145,7 (C-14), 145,5 (C-25), 144,2 (C-9), 126,5 (C- 25), 125 (C-8) and 120,3 (C-15), 7 methyl signals, 2 metin, 9 methylene and 4 quaternary carbon.The results of anticancer tests showed GC-2 had very strong breast anticancer activity with IC50 value is 24,97 µg / mL. Keywords: Anticancer activity, Garcinia celebica, isolation, characterization KATA PENGANTAR Puji dan syukur penulis panjatkan kepada Allah Yang Maha Esa, karena berkat rahmat dan hidayah-Nya penulis dapat menyelesaikan skripsi yang berjudul “Isolasi Senyawa Triterpenoid dari Ekstrak Aseton Daun Garcinia celebica L dan Uji Aktivitas Antikanker Payudara (MCF-7)” Penulis menyadari bahwa terselesaikannya skripsi ini tak lepas dari bantuan dan peranan banyak pihak. Pada kesempatan ini, penulis mengucapkan terima kasih kepada: 1. Dr. Sri Hartati, M.Si selaku Pembimbing I yang telah memberikan pengarahan serta bimbingannya baik dalam teknis di lapangan maupun dalam menyelesaikan skripsi ini. 2. Dr. Siti Nurbayti, M.Si selaku Pembimbing II dan Pembimbing Akademik yang telah memberikan pengarahan serta bimbingannya sehingga banyak membantu penulis dalam menyelesaikan skripsi ini. 3. Tarso Rudiana, M.Si sebagai Penguji I yang telah memberikan saran serta masukan yang bermanfaat. 4. Nurhasni, M.Si sebagai Penguji II yang telah memberikan saran serta masukan yang bermanfaat. 5. Drs. Dede Sukandar, M.Si selaku Ketua Program Studi Kimia Fakultas Sains dan Teknologi UIN Syarif Hidayatullah Jakarta. 6. Dr. Agus Salim, M.Si selaku Dekan Fakultas Sains dan Teknologi UIN Syarif Hidayatullah Jakarta. 7. Isalmi Aziz, M.T selaku Sekretaris Program Studi Kimia Fakultas Sains dan Teknologi UIN Syarif Hidayatullah Jakarta. v 8. Bapak, Ibu, dan Adik tercinta atas segala doa, pengorbanan, nasihat dan motivasinya kepada penulis. 9. Segenap dosen Program Studi Kimia atas ilmu pengetahuan dan pegalaman hidup yang dengan ikhlas diajarkan dan diberikan kepada penulis. 10. Sahabat tersayang Esti, Ayu, Kak Yeni, Lucyta, Isni, Chinta, Nur Fauziyah, Nurlathifah, Afriana, Nur Azizah, Nur Ana, Indah, dan Nadhia yang senantiasa memberi bantuan, dukungan, nasihat dan motivasinya kepada penulis. 11. Teman–teman Kimia Angkatan 2014 yang senantiasa memberi dukungan, motivasi, dan keceriaan kepada penulis. 12. Serta semua pihak yang telah membantu secara langsung dan tidak langsung, yang tidak dapat disebutkan satu persatu. Penulis berharap skripsi ini dapat bermanfaat bagi penulis dan umumnya bagi kemajuan ilmu dan teknologi. Jakarta, Oktober 2018 Ambar Ilafah Ramadhan vi DAFTAR ISI Halaman KATA PENGANTAR ............................................................................................ v DAFTAR ISI ........................................................................................................ vii DAFTAR GAMBAR .............................................................................................. x DAFTAR TABEL ............................................................................................... xii DAFTAR LAMPIRAN ...................................................................................... xiii BAB I PENDAHULUAN ....................................................................................... 1 1.1 Latar Belakang ............................................................................................... 1 1.2 Rumusan Masalah .......................................................................................... 5 1.3 Hipotesis ........................................................................................................ 5 1.4 Tujuan Penelitian ........................................................................................... 6 1.5 Manfaat Penelitian ......................................................................................... 6 BAB II TINJAUAN PUSTAKA ........................................................................... 7 2.1 Tinjauan Umum Tumbuhan Garcinia celebica L ......................................... 7 2.1.1 Fitokimia Tumbuhan Garcinia ......................................................... 8 2.1.3 Aktivitas Biologis Metabolit Sekunder dari Garcinia .................... 18 2.2 Metode Isolasi Senyawa Aktif ..................................................................... 20 2.2.1 Ekstraksi .......................................................................................... 20 2.2.2 Kromatografi Lapis Tipis ................................................................ 21 2.3.3 Kromatografi Kolom ....................................................................... 22 2.3 Karakterisasi Struktur dengan Metode Spektroskopi .................................. 23 2.4.1 Spektroskopi UV-Vis ...................................................................... 24 2.4.2 Spektroskopi FTIR .......................................................................... 25 2.4.3 Spektroskopi Massa (MS) ............................................................... 26 2.4.4 Spektroskopi 1H NMR dan 13C NMR ............................................. 27 vii BAB III METODE PENELITIAN ..................................................................... 29 3.1 Tempat dan Waktu Penelitian ...................................................................... 29 3.2 Alat dan Bahan ...........................................................................................
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