RESVERATROL DERIVATIVE COMPOUNDS FROM STEM BARK OF HOPEA AND THEIR BIOLOGICAL ACTIVITY TEST
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1 RESVERATRL DERIVATIVE CMPUNDS FRM STEM BARK F PEA AND TEIR BILGICAL ACTIVITY TEST Sri Atun a, Nurfina Aznam a, Retno Arianingrum a, Takaya Y b, Niwa Masatake b a Department Chemistry education, Universitas Negeri Yogyakarta, Karangmalang, Depok, Sleman, Yogyakarta, b Faculty of Pharmacy, Meijo University, Tempaku, Nagoya, Japan
2 opea is one the main genus of Dipterocarpaceae, consisting of approximately 100 species and widely distributed in Indonesia specially in Kalimantan The local name is cengal, merawan hitam or pengarawan. The plant ussually can be used as material building, plywood etc. This family of plant is known to produce a variety of resveratrol oligomer These structures are very interesting and showed interesting biological activity, such as antibacterial, anticancer, antihepatotoxic, and anti-iv
3 bjective Phytochemical study of resveratrol oligomers from opea mengarawan,. odorata, and. nigra
4 METD F RESEARC Sample: milled dried stem bark Extraction by organic solvent : acetone or methanol EKSTRAK By fractionated (VLC) Fr. A Fr. B Fr. C Fr. D Repeated Chromatography Activity test Pure compounds S-1, S-2, dst elusidasion structure by spektroskopi methode (UV, FT-IR, NMR, MS) BIACTIVE CMPUNDS STRUCTURE MLECULE
5 W T ISLATED CMPUNDS FRM NATURAL PRDUCT Maserated by organic solvent removal of the solvent under reduced pressure Prepared for VLC
6 VLC Series of fraction
7 chromatogram from chromatography coloumn
8 Isolated compounds from. mengarawan (5 Kg) balanocarpol (300 mg) heimiol A (200 mg), vaticanol G (70 mg) vaticanol B (200 mg)
9 Isolated compounds from. odorata (3,8 Kg) balanocarpol (300 mg) hopeaphenol (1500 mg) 4b B1 1b 7b 12a 10a A2 8b 8a 7a 14b B2 1a A1 12b 4a ampelopsin (250 mg) 4a 12a A1 12b 1a 7a B2 8a A2 7c 10a 8b 8c 7b B1 4b C2 12c C1 8d 7d hemlesyanol C (120 mg) 4c D2 D1 12d 4d
10 Isolated compounds from. odorata (3,8 Kg) vaticanol G (200 mg)
11 Spektrum UV dan IR Vaticanol B
12 Spectrum 1 and 13 C NMR of vaticanol B
13 Spectrum - CSY NMR of vaticanol B 12b 7a 7d 7b 8d 8a 8c 7c 8b 8b 7b 7d 7c 8a 8c 8d B1 A2 A1 C1 7b 8a 7a D2 8d B2 7d C2 D1 7a 12b
14 Table 3. Data activity test as hydroxyl radical scavenger Sample IC 50 ( g/ml) Note Balanocarpol 1802,3 Less active eimiol A Less active Vaticanol G active Vaticanol B Less active opheaphenol 61,8 igh active Ampelopsin 4840,0 Less active emlesyanol C 425,5 active Ascorbat acid 83,9 igh active Butylated ydroxy Toluene (BT) 1328,1 Less active
15 Table. 4. LC 50 of some compounds from steam bark of opea against ela-s3 cell No Sample LC 50 g/ml Note 1 Balanocarpol 682,16 Less active 2 eimiol A Very high Not active 3 Vaticanol G Very high Not active 4 Ampelopsin 8,12 Very active 5 Vaticanol B 92,04 Very active 6 opeaphenol 1931,52 Less active 7 emsleyanol C 531,00 Active 8 Doksorubisin (positif control) 96,27 Very active
16 Table. 5. LC 50 of some compounds from steam bark of opea against Raji cell No Sample LC 50 g/ml Note 1 Balanocarpol 277,58 Active 2 eimiol A Very high Not active 3 Vaticanol G 11050,96 Not active 4 Ampelopsin 91,07 Very active 5 Vaticanol B 107,00 Very active 6 opeaphenol 135,64 Active 7 emsleyanol C 166,84 Active 8 Doksorubisin (positif control) 156,64 Active
17 Cytotoxicity test by ela S3 cell lines ela S3 cell lines before experiment ela S3 cell lines after experiment
18 Cytotoxicity test by Raji cell lines Raji cell lines before experiment Raji cell lines after experiment
19 Conclusion This research we concluded that resveratrol derivative isolated from the stem bark of opea consist of dimer, trimer, and tetramer resveratrol. Some compounds have biological activity as antioxidant and cytotoxic effect against Raji and ela-s3 lines cell. opeaphenol showed the highest activity as antioxidant. Whereas ampelopsin and vaticanol B gives the highest cytotoxic effect against ela-s3 and Raji. Acknowledgements This work has been supported by competitive grant (Insentif Riset Dasar, Ristek- 2008), Ministry Reseach and Technology, Republic of Indonesia. The authors are grateful to the experimental Garden in Carita, Pandeglang, Banten, Indonesia and erbarium Bogoriensis for supported the sample and identification of the plant specimen.
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