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LIMA SENYAWA FENOLIK DARI KULIT KAYU Dipterocarpus Elongatus (DIPTEROCARPACEAE) DAN SIFAT SITOTOKSIKNYA TERHADAP SEL MURIN LEUKEMIA P-388

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LIMA SENYAWA FENOLIK DARI KULIT KAYU Dipterocarpus Elongatus (DIPTEROCARPACEAE) DAN SIFAT SITOTOKSIKNYA TERHADAP SEL MURIN LEUKEMIA P-388 LIMA SENYAWA FENOLIK DARI KULIT KAYU Dipterocarpus elongatus (DIPTEROCARPACEAE) DAN SIFAT SITOTOKSIKNYA TERHADAP SEL MURIN LEUKEMIA P-388 Muhtadi,1∗) Euis H. Hakim,2) Yana M. Syah,2) Lia D. Juliawaty,2) Sjamsul A. Achmad,2) dan Jalifah Latip3) 1) Fakultas Farmasi, Universitas Muhammadiyah Surakarta, Jalan A. Yani Tromol Pos I Pabelan Kartasura, Surakarta 57102, Indonesia 2) Kelompok Penelitian Kimia Organik Bahan Alam, Departemen Kimia, Institut Teknologi Bandung, Jalan Ganeca 10 Bandung 40132, Indonesia 3) School of Chemical Sciences & Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor D.E., Malaysia ABSTRAK Lima senyawa fenolik, yaitu (-)-laevifonol (1), (-)-α-viniferin (2), (-)-vatikanol A (3), bergenin (4) dan 4’- O-metilgalokatecin (5), telah berhasil diisolasi dari ekstrak aseton kulit batang Dipterocarpus elongatus. Struktur molekul senyawa-senyawa tersebut ditetapkan berdasarkan data spektroskopi UV, IR, 1H NMR dan 13C NMR serta perbandingan dengan data sejenis yang telah dilaporkan. Pengujian aktivitas sitotoksik terhadap sel murin leukemia P-388 dilakukan dengan metode MTT assay. Hasil pengujian aktivitas sitotoksik dari masing-masing senyawa menunjukkan nilai IC50 berturut-turut sebesar >100; 17,5; 27,0; >100 dan 70,0 µg/ml. Kata kunci : Senyawa fenolik, sitotoksik, sel murin P-388, Dipterocarpus elongatus, Dipterocarpaceae ABSTRACT Five phenolic compounds; i.e. (-)-laevifonol, (-)-α-viniferin, (-)-vaticanol A, bergenin and 4’-O- methylgallocathecin were isolated from acetone extracts of the stem bark of Dipterocarpus elongatus. The structure of the isolates were established based on spectroscopic evidence; UV, IR, 1H NMR, 13C NMR, and by comparison with the standard compounds. The cytotoxic activities of these compounds were evaluated against murine leukaemia P-388 cells with MTT assay. The IC50 values of all compounds were >100.0; 17.5; 27.0; >100.0 and 70.0 µg/ml, respectively. Keywords : Phenolic compounds, cytotoxic, murine P-388 cells, Dipterocarpus elongates, Dipterocarpaceae ∗ Alamat korespondensi: Tel.: +62-271-717417 Pes.: 305, Fax: +62-271-715448, E-mail: [email protected] PENDAHULUAN Dipterocarpaceae atau yang lebih dikenal (-)-hemsleyanol D, (-)-miyabenol C, (-)-ε- dengan “meranti, keruwing, atau kamfer” viniferin, (-)-ampelopsin F, isoampelopsin F, adalah merupakan tumbuhan pohon penghasil (-)-shorealakton, dan bergenin (Ito et al., kayu yang sangat unggul kualitasnya. Menurut 2004). Sedangkan dari D. retusus telah Newman et al. (1999), famili berhasil diisolasi (-)-ε-viniferin, (-)-α- Dipterocarpaceae memiliki jumlah spesies viniferin, (-)-vatikanol A bersama-sama yang relatif besar, yaitu terdiri dari 16 genus dengan skopoletin dan bergenin (Muhtadi et dan 600 spesies. Genus utama dari famili ini al., 2005) dan dari D. hasselti telah dilaporkan adalah Shorea, Hopea dan Dipterocarpus, adanya senyawa-senyawa (-)-ε-viniferin, yang masing-masing terdiri dari sekitar 150, (-)-laevifonol, (-)-α-viniferin, (-)-vatikanol B, 100 dan 75 spesies. Genus lain, seperti Vatica, (-)-hopafenol, dan (+)-diptonindonesin E dari terdiri dari sekitar 15 spesies, sedangkan genus hasil isolasi kulit batangnya (Muhtadi et al., Dryobalanops, Parashorea, dan Upuna 2006). Fakta ini menunjukkan adanya merupakan genus yang memiliki spesies senyawa oligomer resveratrol baru dari genus paling kecil dan di Indonesia, masing-masing ini, dan memberikan peluang untuk terdiri dari 8, 6, dan 1 spesies. Tumbuhan ini mengungkap keragaman kandungan senyawa- terdapat sangat melimpah di wilayah senyawa oligomer resveratrol dalam genus Indonesia, khususnya di Pulau Kalimantan dan Dipterocarpus. juga tersebar di Indonesia bagian barat, Dalam makalah ini akan disampaikan Malaysia, Brunei, dan Filipina, serta ke arah penemuan lima senyawa fenolik dari ekstrak timur hingga Irian Jaya dan Papua Nugini aseton kulit batang tumbuhan D. elongatus (Newman et al., 1999). Korth dan aktivitas sitotoksiknya terhadap sel Kandungan senyawa kimia metabolit murin leukemia P-388. Tiga senyawa dari sekunder tumbuhan famili Dipterocarpaceae jenis oligomer resveratrol, yaitu (-)-laevifonol cukup beragam, meliputi golongan fenol, (1), (-)-α-viniferin (2) dan (-)-vatikanol A (3), seperti oligostilbenoid (oligomer resveratrol), sedangkan dua dari kelompok senyawa yang flavonoid, fenilpropanoid, dan turunan asam lain, yaitu bergenin (4) senyawa turunan asam fenolat, serta golongan non-fenol, yaitu fenolat dan 4’-O-metilgalokatecin (5), triterpenoid (Sotheeswaran and Pasuphaty, senyawa turunan flavan-3-ol. Pemisahan 1993, Hakim, 2002). Senyawa oligomer senyawa-senyawa fenolik dan sifat resveratrol, yang tersusun dari unit monomer sitotoksiknya dari spesies D. elongatus Korth resveratrol, merupakan metabolit sekunder ini merupakan penelitian terbaru yang belum utama dalam famili ini (Sotheeswaran and pernah dilaporkan sebelumnya. Pasuphaty, 1993; Hakim, 2002). Sejauh ini, Penentuan struktur senyawa-senyawa telah dilaporkan berbagai contoh oligomer tersebut ditetapkan berdasarkan data resveratrol dari kelompok dimer, trimer, spektroskopi UV, IR, 1H NMR dan 13C NMR tetramer, heksamer, heptamer, dan oktamer serta perbandingan dengan data sejenis yang resveratrol (Sotheeswaran and Pasuphaty, telah dilaporkan. Sedangkan aktivitas 1993; Ito et al., 2001-a; 2001-b). Kajian kimia sitotoksiknya ditentukan dengan menggunakan khususnya kandungan senyawa fenolik dari sel murin leukemia P-388 berdasarkan metode Dipterocarpus belum banyak dilakukan. MTT dan prosedur standar yang Berdasarkan kajian literatur baru tiga spesies dikembangkan oleh NCI (Hostettmann, 1991). dari genus Dipterocarpus yang telah dilaporkan kandungan senyawa fenoliknya, METODOLOGI PENELITIAN yakni dari D. grandiflorus telah berhasil Bahan diisolasi senyawa-senyawa, yaitu grandifenol Bahan tumbuhan yang digunakan adalah kulit A dan B, (-)-ampelopsin A, (+)-α-viniferin, (- batang D. elongatus Korth, diperoleh dari )-hopeafenol, (-)-vatikanol B, (-)-vatikanol C, kebun percobaan Haurbentes (Jasinga), Bogor, Jawa Barat, pada bulan November 2001. kromatografi radial (eluen CHCl3 : MeOH = 9 Tumbuhan tersebut diidentifikasi oleh staf : 1) diperoleh α-viniferin (2) (53 mg) dan 4’- Herbarium Bogoriensis, Lembaga Ilmu O-metilgalokatecin (5) (11 mg). Fraksi D Pengetahuan Indonesia (LIPI) Bogor. (1,72 g) difraksinasi dengan KCV (eluen n- heksana : etilasetat = 3 : 7 – etilasetat : MeOH Jalannya Penelitian = 8 : 2) diperoleh 4 fraksi (D1-D4) berturut- Titik leleh ditentukan dengan ‘micro turut beratnya 137 mg, 125 mg, 383 mg, dan melting point apparatus’. Putaran optik diukur 103 mg. Dari fraksi D3 dan D4 diperoleh dengan polarimeter Perkin-Elmer 341 dalam kristal putih, dan setelah dilakukan MeOH. Spektrum UV dan IR ditetapkan rekristalisasi diperoleh bergenin (4) (106 mg). dengan Cary Varian 100 Conc. dan Perkin- Selanjutnya terhadap sebagian fraksi D3 (283 Elmer Spectrum One FT-IR mg) dilakukan pemisahan dan pemurnian lebih spectrophotometers. Spektrum 1H dan 13C lanjut dengan kromatografi radial (eluen NMR ditentukan dengan spektrofotometer CHCl3 : MeOH = 9 : 1) diperoleh laevifonol JEOL ECP400, yang beroperasi pada 400 (1) (37 mg) dan vatikanol A (3) (15 mg). 1 13 MHz ( H) dan 100 MHz ( C). Kromatografi cair vakum menggunakan Si-gel 60 GF254 Penentuan sifat sitotoksik (Merck), kromatografi radial menggunakan Si- Aktivitas sitotoksik senyawa 1-5 dinyatakan gel 60 PF254 (Merck), dan analisis KLT sebagai IC50, yaitu konsentrasi sampel yang menggunakan plat KLT Kieselgel 60 GF254 dibutuhkan untuk menginhibisi 50% sel murin 0,25 mm (Merck). Pelarut yang digunakan leukemia P-388 melalui pewarnaan pereaksi semuanya berkualitas teknis yang didestilasi. MTT. Uji dilakukan dengan cara menambahkan berbagai konsentrasi ketiga Ekstraksi dan Isolasi senyawa tersebut ke dalam biakan sel murin Serbuk kering kayu batang D. leukemia P-388. Setelah diinkubasi selama 48 elongatus sebanyak 1,6 kg dimaserasi dua kali jam, ke dalam sampel ditambahkan pereaksi dengan pelarut aseton 8 L (masing-masing 1 warna MTT dan diinkubasikan kembali X 24 jam), sehingga diperoleh 41 g ekstrak selama 4 jam. Jumlah sel tumor P-388 yang aseton, setelah itu maserasi dilanjutkan dengan terinhibisi oleh sampel diukur dari serapannya pelarut metanol 1 X 8 L (1 X 24 jam), dengan menggunakan alat pembaca pelat diperoleh 30 g ekstrak metanol. Masing- mikro pada λ 540 nm setelah penambahan masing ekstrak selanjutnya dilarutkan kembali larutan penghenti pertumbuhan. Nilai IC50 dalam campuran MeOH-dietileter untuk dapat dihitung melalui ekstrapolasi garis 50% pengendapan tanin, sehingga diperoleh ekstrak serapan kontrol positif pada kurva serapan aseton kering (21 g) dan ekstrak metanol terhadap berbagai konsentrasi sampel kering (20 g). Gabungan kedua ekstrak (41 g) menggunakan grafik semilogaritma. difraksinasi dengan KCV (eluen n-heksan- (-)-Laevifonol (1), diperoleh sebagai serbuk etilasetat (7 : 3) – etilasetat, MeOH) o 20 putih kecoklatan, t.l. 242 C (terurai), [α]D - menghasilkan lima fraksi utama A-E (masing- o masing 13,02; 4,03; 1,72; 1,72; dan 6,89 g). 135 (c 0,1, MeOH); UV (MeOH) λmaks nm: Fraksi C (1,72 g) selanjutnya dipisahkan 203, 228 (bahu), 284; UV (MeOH+NaOH) λmaks nm: 207, 251 (bahu), 295; IR (KBr) ν dengan menggunakan cara kromatografi radial -1 (eluen klorofrom : MeOH = 9,5 : 0,5 – maks cm : 3411, 1787, 1614, 1514, 1452, 1 etilasetat : MeOH = 8 : 2) sehingga diperoleh 1259, 1125, 835; H NMR (aseton–d6, 400 13 4 fraksi C1-C4 berturut-turut beratnya 247 mg, MHz) δ ppm: lihat Tabel 1;
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