Sains Malaysiana 41(12)(2012): 1571–1577

 

Chemical Constituents of Stem Bark of Shorea faguetiana

(Juzuk Kimia Kulit Batang Shorea faguetiana)

 

 

S. Rohaiza, W.A. Yaacob* & L.B. Din

School of Chemical Sciences and Food Technology, Faculty of Science and Technology

Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia

 

I. Nazlina

School of Biosciences and Biotechnology, Faculty of Science and Technology

Universiti Kebangsaan Malaysia, 43600 UKM Bangi, Selangor, Malaysia

 

Diserahkan: 21 Oktober 2011 /  Diterima: 21 Julai 2012

 

 

ABSTRACT

A phytochemical investigation on the acetone extract of the stem bark of Shorea faguetiana was conducted. The isolation of the chemical compounds was carried out by different chromatographic techniques and their structures were elucidated by spectroscopic methods including UV, IR, NMR and MS, and also by comparison with the literature. Five oligostilbenes were isolated and identified as (-)-ε-viniferin, (-)-α-viniferin, (-)-laevifonol, (-)-ampelopsin E and (-)-hopeaphenol.

 

Keywords: (-)-Ampelopsin E; (-)-α-Viniferin; Dipterocarpaceae; (-)-ε-Viniferin; (-)-Hopeaphenol; (-)-Laevifonol; Oligostilbenes; Shorea faguetiana

 

ABSTRAK

Kajian kimia terhadap ekstrak aseton kulit batang Shorea faguetiana telah dilakukan. Pemisahan sebatian kimia dijalankan dengan menggunakan berbagai teknik kromatografi dan struktur telah ditentukan menggunakan kaedah spektroskopi seperti UL, IM, RMN dan SJ, serta membandingkan data yang diperoleh dengan data kepustakaan. Lima oligostilbena telah dipisahkan dan dikenal pasti sebagai (-)-ε-viniferin, (-)-α-viniferin, (-)-laevifonol, (-)-ampelopsin E dan (-)-hopeafenol.

 

Kata kunci: (-)-Ampelopsin E; (-)-α-Viniferin; Dipterocarpaceae; (-)-ε-Viniferin; (-)-Hopeafenol; (-)-Laevifonol;    Oligostilbena; Shorea faguetiana

 

RUJUKAN

Aminah, N.S., Achmad, S.A., Aimi, N., Ghisalberti, E.L., Hakim, E.H., Kitajima, M., Syah, Y.M. & Takayama, H. 2002. Diptoindonesin A, a new C-glucoside of ε-viniferin from Shorea seminis. Fitoterapia 73: 501-507.

Bokel, M., Diyasena, M.N.C., Gunatilaka, A.A.L., Kraus, W. & Sotheeswaran, S. 1988. Caliculatol, an antifungal resveratrol trimer from Stemonoporus canaliculatus. Phytochemistry 27: 377-380.

Burkill, I.H. 1966. A Dictionary of the Economic Products of Malaysia Peninsula. Kuala Lumpur: Governments of Malaysia and Singapore (2nd edition).

Cronquist, A. 1981. An Integrated System of Classification of Flowering Plants. New York: Columbia University Press.

Dai, J.R., Hallock, Y.F., Cardellin, J.H. & Boyd, M.R. 1998. HIV-inhibitory and cytotoxic oligostilbenes from the leaves of Hopea malibato. J. Nat. Prod. 61: 351-353.

Hadi, S. & Noviany. 2009. The isolation of hopeaphenol, a tetramer stilbene, from Shorea ovalis Blume. Adv. Nat. Appl. Sci. 3: 107-112.

Haryoto. 2008. Oligomer resveratrol dari beberapa spesies Shorea (Dipterocarpaceae) Indonesia. Disertasi Institut Teknologi Bandung, Bandung (unpublished).

Henye, K. 1987. Tumbuhan Berguna Indonesia. Jakarta: Badan Litbang Kehutanan.

Hirano, Y., Kondo, R. & Sakai, K. 2003. Novel stilbenoids isolated from the heartwood of Shorea laeviforia. Japan Wood Sci. 49: 53-58.

Ito, T. 2011. Structures of oligostilbenoids in dipterocarpaceaeous plants and their biological activities. Yakugaku zasshi: J. Pharm. Soc. Japan 13: 93-100.

Ito, T., Tanaka, T., Ido, Y., Nakaya, K.I., Iinuma, M. & Riswan, S. 2000. Stilbenoids isolated from stem bark of Shorea hemsleyana. Chem. Pharm. Bull. 48: 1001-1005.

Jang, M., Cai, L., Udeani, G.O., Slowing, K.V., Thomas, C.F., Beecher, C.W., Fong, H.H.S., Farnsworth, N.R., Kinghorn, A.D., Mehta, R.G., Moon, R.C. & Pezzuto, J.M. 1997. Cancer chemopreventive activity of resveratrol, a natural product derived from grapes. Science 275: 218-220.

Kusuma, I.W. & Tachibana, S. 2007. Antifungal compounds isolated from tropical and temperate woods. ACS Symposium Series. 954 (Materials, Chemicals and Energy from Forest Biomass): pp. 377-390.

Latip, J., Zain, W.Z.W.M., Ahmat, N., Yamin, B.M., Yusof, N.I.N., Syah, Y.M. & Achmad, S.A. 2011. Cytotoxic oligostilbenoids from Vatica odorata. Aust. J. Basic Appl. Sci. 5: 113-118.

Li, W.W., Ding, L.S., Li, B.G. & Chen, Y.Z. 1996. Oligostilbenes from Vitis heyneana. Phytochemistry 42: 1163-1165.

Lin, M. & Yao, C.S. 2006. Studies in natural products chemistry 33. Bioactive Natural Products Part M: 601-644.

Misra, L.N. & Ahmad, A. 1997. Triterpenoids from Shorea robusta resin. Phytochemistry 45: 575-578.

Muhtadi Hakim, E.H., Syah, Y.M., Juliawaty, L.D., Achmad, S.A., Said, I.M. & Latip, J. 2005. Tiga senyawa oligostilbenoid dari kulit batang Dipterocarpus retusus Blume (Dipterocarpaceae). Jurnal Matematika dan Sains 10(4): 135-141.

Muhtadi Hakim, E.H., Juliawaty, L.D., Syah, Y.M., Achmad, S.A., Latip, J. & Ghisalberti, E.L. 2006. Cytotoxic resveratrol oligomers from the tree bark of Dipterocarpus hasselti. Fitoterapia 77: 550-555.

Muhtadi Hakim, E.H., Syah, Y.M., Juliawaty, L.D., Achmad, S.A., Said, I.M., Din, L. & Latip, J. 2007. Resveratrol oligomer compounds from the tree bark of Dipterocarpus elongates and cytotoxic effect against murine leukaemia P-388 cells. Proceeding JSChem-ITB-UKM-2007, pp. 459-463.

Nitta, T., Arai, T., Takamatsu, H., Inatom, Y., Murata, H., Iinuma, M., Tanaka, T., Ito, T., Asai, F. & Watabe, K. 2002. Antibacterial activity of extracts prepared from tropical and subtropical plants on methicillin-resistant Staphylococcus aureus. J. Health Sci. 48: 273-276.

Noviany. 2002. Eksplorasi senyawa oligomer stilbenoid dari tumbuhan Shorea multiflora Burck. Tesis S2. Institut Teknologi Bandung, Bandung (unpublished).

Oshima, Y. & Ueno, Y. 1993. Ampelopsins D, E, Hand cis-ampelopsin E, oligostilbenes from Ampelopsis brevipedunculata var. hancei roots. Phytochemistry 33: 179-182.

Saroyobudiono, H., Juliawaty, L.D., Shah, Y.M., Achmad, S.A., Hakim, E.H., Latip, J. & Said, I.M. 2008. Oligostilbenoids from Shorea gibbosa and their cytotoxic properties against P-388 cells. J. Nat. Med. 62: 195-198.

Subeki, N.S., Matsuura, H., Yamasaki, M., Yamato, O., Maede, Y., Katakura, K., Suzuki, M. & Trimurningsih, C. 2005. Anti-babesial activity of some Central Kalimantan plant extracts and active oligostilbenoids from Shorea balangeran. Planta Medica 71: 420-423.

Symington, N. 1974. Foresters Manuals of Dipterocarps. Kuala Lumpur: Universiti Malaya (2nd edition).

Tukiran Achmad, S.A., Hakim, E.H., Makmur, L., Sakai, K., Shimizu, K. & Syah, Y.M. 2005. Oligostilbenoids from Shorea balangeran. Biochem. Syst. Ecol. 33: 631-634.

Varshney, V.K. & Dayal, R. 2006. Chemical constituents of Shorea robusta. Int. J. Chem. Sci. 4: 298-304.

Westphal, P. & Battermann, M. 2010. Shampoos and hair conditioners containing fine wood extracts. PCT Int. Appl. WO 2010079041 A1 20100715.

Wibowo, A., Ahmat, N., Hamzah, A.S., Sufian, A.S., Ismail, N.H., Ahmad, R., Jaafar, F.M. & Takayama, H. 2011. Malaysianol A, a new trimer resveratrol oligomer from the stem bark of Dryobalanops aromatica. Fitoterapia 82(4): 676-681.

Zuraida, W.W.M.Z. 2005. Pengasingan dan pencirian sebatian oligostilbena daripada Vatica odorata (Dipterocapaceae). Tesis Sarjana Sains, Fakulti Sains dan Teknologi, Universiti Kebangsaan Malaysia (unpublished).

 

 

*Pengarang untuk surat-menyurat; email: wanyaa@ukm.my

 

 

 

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