RESVERATROL DIMERS FROM STEM BARK OF Hopea gregaria AND THEIR CYTOTOXIC PROPERTIES

https://doi.org/10.22146/ijc.21629

Sahidin Sahidin(1*), Euis Holisotan Hakim(2), Yana Maolana Syah(3), Lia Dewi Juliawaty(4), Sjamsul Arifin Achmad(5), Laily Bin Din(6), Jalifah Latip(7)

(1) Department of Chemistry, Faculty of Mathematics and Natural Sciences, Haluoleo University, Kampus Baru Anduonohu, Kendari, South East Sulawesi
(2) Natural Products Research Group, Departement of Chemistry, Institut Teknologi Bandung, Jalan Ganeca 10 Bandung 40132
(3) Natural Products Research Group, Departement of Chemistry, Institut Teknologi Bandung, Jalan Ganeca 10 Bandung 40132
(4) Natural Products Research Group, Departement of Chemistry, Institut Teknologi Bandung, Jalan Ganeca 10 Bandung 40132
(5) Natural Products Research Group, Departement of Chemistry, Institut Teknologi Bandung, Jalan Ganeca 10 Bandung 40132
(6) School of Chemical Sciences & Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor D.E
(7) School of Chemical Sciences & Food Technology, Faculty of Science and Technology, Universi
(*) Corresponding Author

Abstract


Six resveratrol dimers have been isolated from the stem bark of H. gregaria, ampelopsin A (1), balanocarpol (2), ε-viniferin (3), hopeafuran (4), heimiol A (5), and parviflorol (6). The structures of these compounds were determined based on spectroscopic evidence such as UV, IR, 1-D, 2-D NMR and comparison with the reported data. These compound inventions are strengthen conclusion that Hopea tends to produce resveratrol dimers. Biological activity of those compounds against murine leukemia P-388 cells showed that ε-viniferin (3) is the most active compound with IC50 value 5.1 ± 0.3 μg/mL.


Keywords


H. gregaria; resveratrol dimers; murine leukemia P-388 cells

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References

[1] Ashton, P. S., 1983, Flora Malesiana: Spermatophyta I, Martinus Nijhoff, The Hague, 391-436.

[2] Sotheeswaran, S., and Pasupathy, V., 1993, Phytochemistry 32 (5), 1083-1092.

[3] Atun, S., 2004, Fitokimia beberapa spesies Dipterocarpaceae Indonesia dari genus Vatica, Anisoptera, Hopea, and Dipterocarpus, Disertasi Program Doktor, Institut Teknologi Bandung, 76-162.

[4] Tukiran, 2004, Senyawa Mikromolekul dari Beberapa Tumbuhan Meranti (Shorea) Indonesia, Disertasi Program Doktor, Institut Teknologi Bandung, 70-112.

[5] Sahidin, Hakim, E. H., Juliawaty, L. D., Syah, Y. M., Din, L. B., Ghisalberti, E. L., Latip, J., Said, I. M., and Achmad, S. A., 2005, Z. Naturforsch. C, 60c: 718-723

[6] Sahidin,Hakim,E.H., Syah,Y.M., Juliawaty,L.D.,Achmad, S.A., Din, L.B., Latip, J., and Ghisalberti, E.L., 2006, Berita Biologi 8 (2), 107-114.

[7] Coggon, P., McPhail, A.T., and Wallwork, S.C. J., 1970, J. Chem. Soc. (B), 884-897.

[8] Sotheeswaran, S., Sultanbawa, M.U.S., Surendrakumar, S., Balasubramaniam, S., and Bladon, P., 1983, J. Chem. Soc. I, 159-162.

[9] Diyasena, M. N. C., Sotheeswaran, S., and Surendrakumar, S., 1985, J. Chem. Soc. Perkin Trans I, 1807-1809.

[10] Dai, J.R., Hallock, Y.F., Cardellina II, J.H., and Boyd, M.R., 1998, J. Nat. Prod., 61, 351-353.

[11] Sotheeswaran, S., Sultanbawa, M.U.S., Surendrakumar, S., and Bladon, P., 1985, J. Chem. Soc. 4, 159-162.

[12] Nitta, T., Arai, T., Takamatsu, H., Inatomi, Y., Murata, H., Iinuma, M., Tanaka, T., Ito, T., Asai, F., Ibrahim, I., Nakanishi, T., and Watanabe, K., 2002, J. Health Sci., 48(3):273-276.

[13] Kang, H. J., Park, H. Y., Choi, S. W., Yang, E. K., and Lee, W. J., 2003, Experimental and Molecular Medicine, 35 (6), 467-474.

[14] Hirano, Y., Kondo, R., and Sakai, K., 2003, J. Wood Sci., 49(1), 53-58.

[15] Pryce, R. J., and Langcake, P., 1977, Phytochemistry, 16, 1452-1454.

[16] Kitanaka, S., Ikezawa, T., Yasukawa, K., Yamanouchi, S., Takido, M., Sung, H. K., and Kim, I. H., 1990, Chem. Pharm. Bull., 38 (2), 432-435.

[17] Pols, J. R. Z., Freyer, A. J., Killmer, A. J., and Porter, J, R, 2002, J. Nat. Prod., 65, 1554-1559.

[18] Ohguchi, K., Tanaka, T., Ito, T., Iinuma, M., Matsumoto, K., Akao, Y., and Nozawa, Y., 2003, Biosci. Biotech. Biochem., 67 (7), 1587-1589.

[19] Alley, M. C., Scudiero, D. A., Monks, A., Hursey, M. L., Czerwinski, M. J., Fine, D. L., Abbott, B. J., Mayo, J. G., Shoemaker, R. H., and Boyd, M. R. , 1988, Cancer Res., 48: 589-601.

[20] Tanaka, T., Ito, T., Ido, Y., Son, T. K., Nakaya, K., Iinuma, M., Ohyama, M., and Chelladurai, V., 2000, Phytochemistry, 53, 1009-1014.

[21] Ito, T., Tanaka, T., Ido, Y., Nakaya, K., Iinuma, M., and Riswan, S., 2000, Chem. Pharm. Bull., 48 (12), 1001-1005.

[22] Oshima, Y., and Ueno, Y., 1993, Phytochemistry, 33 (1), 179-182.

[23] Tanaka, T., Ito, T., Ido, Y., Nakaya, K., Iinuma, M., and Chelladurai, V., 2001, Chem. Pharm. Bull., 49 (6), 785-787.

[24] Weber, F. J., Wahab, I. A., Marzuki, A., Thomas, N.F., Kadir, A. A., Hadi, A. H.A., Awang, K., Latiff, A.A., Richomme, P., and Delaunay, 2001, Tetrahedron Letter, 42, 4895-4897.

[25] Sako, M., Hosokawa, H., Ito, T., and Iinuma, M., 2004, J. Org. Chem., 69, 2598-2600.

[26] Takaya, Y., Yan, K. X., Tereshima, K., He, Y. H., and Niwa, M., 2002, Tetrahedron, 58, 9265-9721.



DOI: https://doi.org/10.22146/ijc.21629

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