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AKTIVITAS ANTIOKSIDAN DAN ANTIKANKER SENYAWA GARCINOL DARI EKSTRAK N-HEKSANA KULIT BATANG Garcinia Maingayi Hook

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AKTIVITAS ANTIOKSIDAN DAN ANTIKANKER SENYAWA GARCINOL DARI EKSTRAK N-HEKSANA KULIT BATANG Garcinia Maingayi Hook AKTIVITAS ANTIOKSIDAN DAN ANTIKANKER SENYAWA GARCINOL DARI EKSTRAK N-HEKSANA KULIT BATANG Garcinia maingayi Hook SKRIPSI LUCYTA SARI PROGRAM STUDI KIMIA FAKULTAS SAINS DAN TEKNOLOGI UNIVERSITAS ISLAM NEGERI SYARIF HIDAYATULLAH JAKARTA 2018 M/ 1440 H AKTIVITAS ANTIOKSIDAN DAN ANTIKANKER SENYAWA GARCINOL DARI EKSTRAK N-HEKSANA KULIT BATANG Garcinia maingayi Hook SKRIPSI Sebagai Salah Satu Syarat untuk Memperoleh Gelar Sarjana Sains Program Studi Kimia Fakultas Sains dan Teknologi Universitas Islam Negeri Syarif Hidayatullah Jakarta Oleh: LUCYTA SARI 11140960000068 PROGRAM STUDI KIMIA FAKULTAS SAINS DAN TEKNOLOGI UNIVERSITAS ISLAM NEGERI SYARIF HIDAYATULLAH JAKARTA 2018 M/ 1440 H ABSTRAK LUCYTA SARI. Aktivitas Antioksidan dan Antikanker Senyawa Garcinol dari Ekstrak n-Heksana Kulit Batang Garcinia maingayi Hook. Dibimbing oleh SRI HARTATI dan SITI NURBAYTI Garicinia maingayi Hook merupakan salah satu tanaman obat yang mengandung senyawa xanton, benzofenon, dan triterpenoid yang memiliki aktivitas antioksidan dan antikanker. Uji pendahuluan terhadap ekstrak n-heksana kulit batang G. maingayi menunjukkan aktivitas antioksidan dan antikanker payudara (MCF-7) berturut-turut sebesar 90,51% (100 μg/mL) dan 96,87% (200 μg/mL). Penelitian lanjutan ini dilakukan untuk mengidentifikasi struktur senyawa murni ekstrak n-heksana kulit batang G. maingayi dan menguji aktivitasnya. Isolasi dan fraksinasi senyawa murni dilakukan dengan metode kromatografi kolom. Uji aktivitas antioksidan dan antikanker dilakukan menggunakan metode DPPH (2,2- difenil-1-pikrilhidrazil) dan MTT [3-(4,5-dimetiltiazol-2-il)-2,5-difeniltetrazolium bromida]. Penentuan struktur senyawa menggunakan metode spektroskopi. Isolat GM-1 yang diperoleh berupa kristal jarum kuning pucat dengan titik leleh 122- 124˚C. Analisis isolat GM-1 menggunakan UV-Vis menunjukkan karakteristik senyawa golongan benzofenon dengan λmax 251 nm (kromofor karbonil) dan λmax 355 nm (kromofor aromatik). Spektrum FTIR menunjukkan adanya vibrasi gugus O-H (3.564; 3.274 cm-1), C=O (1.728; 1.623 cm-1), C=C aromatik (1.529 cm-1), C- -1 -1 -1 H aromatik (2.923 cm ), C-H (1.435 cm ) serta CH3 (2.969; 2.872 cm ). Analisis 1 13 H dan C NMR menunjukkan ciri benzofenon terprenilasi pada δH (ppm) 6,58; 6,90; 6,94 (cincin aromatik) dan δH (ppm) 4,91; 5,01; 5,08 (kerangka isoprenil) serta pada δC (ppm) 114,5-128,0; 58,0-209,3 (2 cincin aromatik) dan δC (ppm) 122,8; 123,9; 124,3 (isoprenil). Analisis LC/ESI-MS/MS menunjukkan waktu retensi 8,15 menit serta ion molekul pada m/z 625,3 [M+Na]+ dan 603,3 [M+H]+ sesuai rumus molekul C38H50O6 yang merupakan senyawa garcinol. Hasil uji aktivitas senyawa garcinol menunjukkan aktivitas antioksidan dan antikanker yang sangat kuat dengan nilai IC50 berturut-turut sebesar 16,44 dan 19,13 μg/mL. Kata Kunci : Antikanker, antioksidan, Garcinia maingayi Hook, benzofenon vi ABSTRACT LUCYTA SARI. Antioxidant and Anticancer Activity of Garcinol Compound from n-Hexane Stem Bark Extract of Garcinia maingayi Hook. Supervised by SRI HARTATI and SITI NURBAYTI Garcinia maingayi Hook is medicinal plants which containing xanthones, benzophenones, and triterpenoids. Preliminary evaluation of antioxidant and anticancer activity (MCF-7) from n-hexane extract of stem bark G. maingayi showing IC50 90,51% (100 μg/mL) and 96,87% (200 μg/mL), respectively. This advanced research aimed to identify the structure of pure compound from n-hexane extract of stem bark G. maingayi and to determine their activity. Isolation and fractionation of pure compound using column chromatography method. Determination of antioxidant and anticancer activity was tested by DPPH (2,2- diphenylpicrylhydrazyl) and MTT [3-(4,5-dimethylthiazol-2-yl)-2,5- diphenyltetrazolium bromide]. Structural elucidation of isolate was performed by spectroscopic methods. Isolate GM-1 was obtained as a pale yellow needles and melting point temperature 122-124˚C. UV Vis spectrum showed the characteristics of benzophenones λmax 251 nm (carbonyl chromophore) and λmax 355 nm (aromatic chromophore). FTIR spectrum showed the vibration of O-H function group (3.564; 3.274 cm-1), C=O (1.728; 1.623 cm-1), aromatic C=C (1.529 cm-1), aromatic C-H -1 -1 -1 1 13 (2.923 cm ), C-H (1.435 cm ) and CH3 (2.969; 2.872 cm ). H and C NMR spectra showed the characteristics of isoprenylated benzophenones at δH (ppm) 6,58; 6,90; 6,94 (aromatic rings) and δH (ppm) 4,91; 5,01; 5,08 (isoprenyl) and signal at δC (ppm) 114,5-128,0; 58,0-209,3 (2 aromatic rings) and δC (ppm) 122,8; 123,9; 124,3 (isoprenyl). The LC/ESI-MS/MS spectrum gave a retention time at 8,15 minutes and molecular ion at m/z 625,3 [M+Na]+ and 603,3 [M+H]+ according to molecular formula C38H50O6 known as garcinol. Bioactivity assay showed a strong antioxidant and anticancer with IC50 = 16,44 and 19,13 μg/mL, respectively. Keywords: Anticancer, antioxidant, Garcinia maingayi Hook, benzophenone vii KATA PENGANTAR Bismillaahirrohmaanirrohim Assalamualaikum Warahmatullah Wabarakatuh Puji dan syukur penulis sampaikan kehadirat Allah SWT, atas segala nikmatNya sehingga penulis mampu menyelesaikan penelitian dan skripsi yang berjudul “Aktivitas Antioksidan dan Antikanker Senyawa Garcinol dari Ekstrak n-Heksana Kulit Batang Garcinia maingayi Hook”. Skripsi ini disusun untuk memenuhi salah satu syarat kelulusan dalam menempuh pendidikan Strata 1 (S1) pada Program Studi Kimia Fakultas Sains dan Teknologi UIN Syarif Hidayatullah Jakarta. Penelitian serta penulisan skripsi ini juga tidak lepas dari adanya bantuan berbagai pihak. Pada kesempatan ini penulis ingin menyampaikan ucapan terima kasih atas bantuan dan kerjasamanya kepada: 1. Dr. Sri Hartati, M.Si selaku pembimbing I yang selalu mendampingi dan memberikan arahan kepada penulis sehingga penulisan skripsi ini dapat terselesaikan. 2. Dr. Siti Nurbayti, M.Si selaku pembimbing II sekaligus dosen pembimbing akademik yang telah membimbing dan memberikan saran kepada penulis sehingga skripsi ini dapat diselesaikan dengan baik. 3. Tarso Rudiana, M.Si selaku penguji I yang telah memberikan saran dan masukan kepada penulis sehingga penulisan skripsi ini bisa terstruktur dengan baik. 4. Dr. Hendrawati, M.Si selaku penguji II yang telah memberikan saran dan masukan yang bermanfaat sehingga skripsi ini bisa disusun dengan lebih baik. viii 5. Drs. Dede Sukandar, M.Si selaku Ketua Program Studi Kimia, Fakultas Sains dan Teknologi, Universitas Islam Negeri Syarif Hidayatullah Jakarta. 6. Dr. Agus Salim, M.Si selaku Dekan Fakultas Sains dan Teknologi Universitas Islam Negeri Syarif Hidayatullah Jakarta 7. Seluruh dosen Program Studi Kimia dan laboran yang telah memberikan ilmu serta membimbing dalam bidang akademik 8. Orang tua dan keluarga yang telah memberikan dukungan serta doa sehingga penulis dalam penelitian ini. 9. Ambar Ilafah Ramadhan, Halwa Salasila, Nur Fauziyah, Afriana Awdady, Nurlathifah, teman seperjuangan dalam riset di Laboratorium Kimia Bahan Alam, Pusat Penelitian Kimia Lembaga Ilmu Pengetahuan Indonesia (LIPI) Puspiptek-Serpong yang selalu membantu dan memberikan semangat. 10. Isni Putri Setyoningsih, Chinta Permatasari Supiandi, dan teman-teman Kimia angkatan 2014 yang selalu memberikan semangat dan dukungan. Penulis berharap semoga skripsi ini dapat bermanfaat dan menjadi salah satu sumbangan pengetahuan dalam pengembangan ilmu pengetahuan di Indonesia, khususnya di bidang ilmu Kimia. Jakarta, Oktober 2018 Lucyta Sari ix DAFTAR ISI Halaman KATA PENGANTAR ........................................................................................ viii DAFTAR ISI ...........................................................................................................x DAFTAR GAMBAR .......................................................................................... xiii DAFTAR TABEL ................................................................................................xv DAFTAR LAMPIRAN ...................................................................................... xvi BAB I PENDAHULUAN .......................................................................................1 1.1 Latar Belakang ................................................................................................. 1 1.2 Rumusan Masalah ............................................................................................ 5 1.3 Hipotesis Penelitian ......................................................................................... 6 1.4 Tujuan Penelitian ............................................................................................. 6 1.5 Manfaat Penelitian ........................................................................................... 6 BAB II TINJAUAN PUSTAKA ...........................................................................7 2.1 Tinjauan Umum Tumbuhan Garcinia ............................................................. 7 2.1.1 Habitat dan Persebaran ........................................................................... 8 2.1.2 Manfaat Tradisional ................................................................................ 9 2.1.3 Kandungan Senyawa Kimia Tumbuhan Garcinia................................ 10 2.1.4 Aktivitas Biologis Metabolit Sekunder Tumbuhan Garcinia............... 17 2.2 Uji Aktivitas Antioksidan Metode Peredaman Radikal Bebas DPPH ........... 21 2.3 Uji Antikanker Metode MTT [3-(4,5-dimetiltiazol-2-il)-2,5- difeniltetrazolium bromida] ........................................................................... 22 2.4 Metode Isolasi Senyawa Bahan Alam ..........................................................
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