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Phytochemical Study Some Phenolic Compounds from Anisoptera Marginata

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Phytochemical Study Some Phenolic Compounds from Anisoptera Marginata PHYTOCHEMICAL STUDY SOME PHENOLIC COMPOUNDS FROM ANISOPTERA MARGINATA Sri Atun Department of Chemical education, Faculty Mathematic and Natural Science, Yogyakarta State University Karangmalang, Depok, Sleman, Yogyakarta, Indonesia, 55281 Email : [email protected] Abstract Anisoptera is the minor genus of Dipterocarpaceae, consisting of approximately 5 species and distributed in Indonesia especially in Kalimantan and Sumatera. Isolation and structure elucidation of some compounds from stem bark of Anisoptera marginata had been done. The isolation of those compounds was carried out by chromatographyc method and structure elucidation was performed by interpretation of spectroscopic data, including UV, IR, 1H and 13C NMR 1D and 2D, and FABMS. From acetone extract stem bark A. marginata we isolated five known compounds named bergenin (1), (-)-ε-vinipherin (2), (-)-ampelopsin A (3), vaticanol B (4), (-)-hopeaphenol (5), and a glycoside compound named hopeaphenol-O- glycoside (6). Keyword: Resveratrol; Hopeaphenol-O-glycoside; Anisoptera marginata Introduction antibacterial, anticancer, antihepatotoxic, and anti-HIV a,b a,b (Dai, 1998; Ito, 2000 ; Sri Atun, 2005; 2006 ). Dipterocarpaceae is one of the largest families Therefore, the following discussion will focus on the found in the tropical forest Indonesia. The plants are structure diversity of phenolic compounds that have distributed from the west of Indonesia until Papua (Irian been found, and biogenetic relationship, of the Jaya) and mostly in Kalimantan, therefor the timber of compound from Anisoptera marginata. these plants are ussually called “meranti” or “Kayu Kalimantan”. Dipterocarpaceae consists of about 16 Results and Discussion genus and 600 species and until now only few species 1. The diversity phenolic compounds from have been investigated. Some chemical constituents that Anisopteramarginata genus can be found from this plant include arilpropanoid, benzofuran, flavanoid, polyphenol, resveratrol Up to now, only one species plant of the oligomers and terpenoid. The resveratrol oligomer from Anisoptera genus, named Anisoptera marginata that Dipterocarpaceae plants have various structure from have been investigated for chemical structures of this simple structure as it monomer, dimer, trimer, until plant. Five phenolic compounds have been found from hexamer. These structures are very interesting and relative non polar fraction acetone extract stem bark of showed interesting biological activities, such as A. marginata (Sri Atun (2004) consist of bergenin (1), antibacterial, anticancer, antihepatotoxic, and anti-HIV (-)-ε-vinipherin (2), (-)-ampelopsin A (3), vaticanol B ( Sothesswaran, 1993; Dai 1998; Sri Atun, 2004; 2005; (4), and (-)-hopeaphenol (5). Whereas from polar 2006). Thus Dipterocarpaceae plants are very potential fraction, has been found hopheaphnenol-O-glycoside for chemical research in natural product and (5) (Sri Atun, 2009). The isolation of those compounds pharmaceutical industry. was carried out by chromatographyc method, and the Anisoptera is the minor genus of structure elucidation was performed by interpretation of Dipterocarpaceae, consists of approximately 5 species spectroscopic data, including UV, IR, 1H and 13C NMR and distributed in Indonesia only in Kalimantan and 1D and 2D, and FABMS. Hopheaphenol-O- glycoside Sumatera (Conqruis, 1991; Heyne, 1987) and until now (5) is a new compound. It is the first time that can be only one species have been investigated, named found in Dipterocarpaceae family, and the other of Anisoptera marginata (Sri Atun, 2009). This family of these plant. plant is known to produce a variety of resveratrol oligomer. These structures are very interesting and showed interesting biological activities, such as HO HO H O O OH O OH H HO O H H H HO OH H CO HO OH 3 OH H O H OH OH H CH2OH OH OH OH Bergenin (1) (-)-e-Vinipherin (2) (-)-Ampelopsin A (3) HO HO HO OH OH H H O O H OH H HO OH HO OH HH H H O H H HO OH HO H H H H H OH OH OH O OH H OH HO HO Vaticanol B (4) (-)-Hopeaphenol (5) 4a HO H A1 O 12b 12c O H OH 1a 7a D1 4d OH HO 1d H B2 C2 O 1' 8a H H O 10d HO 8b 6' A2 8c H OH H 7b 7c OH 12a D2 H H H 1b H 12d HO HOHO H H B1 OH C1 4b 4c OH HO Hopeaphenol –O-glycos ide (6) 2. Biogenetic relationship of oligoresveratrol oligomer isolated contain a heterocyclic ring named structure from Anisoptera marginata trans-2-aryl-2,3-dihydrobezofuran, originated from Many oligoresveratrol with various types oxidative coupling between two unit of resveratrol of the molecular skeleton have been isolated mainly to produce (-)-ε-viniferin (2) as an immediate from some species of Dipterocarpaceae. The precursor. Further couplings of (-)-ε-viniferin (2) biogenetic relationship of all compounds isolated produce other resveratrol oligomers. The biogenetic from some species of Dipterocarpaceae may be relationship between these oligoresveratrol isolated suggested to follow one primary biogenetic in this study is shown in Figure 1. pathway. Generally, the structures of the resveratrol HO 4a H 12b A1 O 12c O H OH 1a 7a D1 4d OH HO 1d H B2 C2 1' 8a H HO O 10d HO 8b 6' OH A2 7b 8c OH H H 7c D2 H 12a H H 1b H 12d HOHO HO H H B1 OH 6 C1 4b 4c OH HO HO H O HO O H OH OH H H H HO H H OH H OH HO HO OH OH OH 5 HO HO H H H O HO HO HO OH O H O H OH H H H H H HO OH HO HO OH OH OH H H HO HO 2 H O H HO OH 4 3 HO HO OH OH Resveratrol (7) O HO O COOH H COOH OH H CO NH2 3 HO OHH O OH 1 CH2OH Karbohidrat Fig. 1. Biogenetic relationship of phenolic compounds from A. marginata 3. Biological activity of oligoresveratrol isolated as phytoalexins, an antimicrobial compounds from Dipterocarpaceae family compound produced by a plants in response to infection or certain other types of physiological Oligoresveratrol is a compound found in stimuli from Vitis vinifera leaves in the year 1977 the Dipterocarpaceae family, which has some (Langcake, 1977). Researchers have shown that useful bioactivities. Resveratrol (1) is the first resveratrol (1) has a chemopreventive activity compound that was found. For the first time, it was against cancer cells (Jang, 1997). Various biological activities of oligoresveratrol compounds Polyphenols from Dipterocarpaceae have been also reported, for example, ε-viniferin species, copalliferol A and stemonoporol, J. (2), showed activity against antimicrobial some Chem. Soc., 4, 699-702. type of microorganism (Sothesswaran, 1993). A Sotheeswaran, S., M.U.S Sultanbawa, S. number of other oligoresveratrol showed activity Surendrakumar, P. Bladon ,1985, against sitotoxic as cancer cell lines, such as (-)- Polyphenol from Dipterocarpaceae species ampelopsin A (3), hopeaphenol (5), are cytotoxic vaticaffinol and - viniferin, J. Chem. Soc. against KB cells carsinoma epidermoid (Tanaka, 4, 159-162. 2000; Ito, 2001â; Ito, 2001b; Seo, 1999), (Dai, 1998). Vaticanol B (4) is cytotoxic against as Hela Sri Atun. 2004. Fitokimia beberapa species S3 and Raji cell lines (Sri Atun, 2008) Dipterocarpaceae Indonesia dari genus Vatica, Anisoptera, Hopea, dan Dipterocarpus. [Disertasi]. Bandung: FPS Institut Teknologi Bandung. Conclusion Sri Atun, Nurfina, Retno A, Niwa M., 2005, A Molecular structure phenolic compounds which trimer stilbenoids compound from stem bark have been found in the A, marginata included gallat Hopea nigra (Dipterocarpaceae), Indo. J. acid derivative, and oligomer resveratrol included Chem, 5 (3), 211-214. dimer, trimer and tetramer with resveratrol. The Sri Atun, Nurfina, Retno A., Niwa M., 2006, structures of the oligoresveratrol isolated contain a Balanocarpol and Heimiol A, two resveratrol heterocyclic ring named trans-2-aryl-2,3- dimers from stem bark Hopea mengarawan dihydrobezofuran, originated from oxidative (Dipterocarpaceae), Indo. J. Chem, 6 (1), 75 – coupling between two unit of resveratrol to 78. produce (-)-ε-viniferin (2) and other compounds. Sri Atun, Sjamsul A.A, Niwa.M, Retno A, Nurfina These structures are very interesting and many A., 2006, Oligostilbenoids from Hopea compounds showed interesting biological activities, mengarawan (Dipterocarpaceae), Biochem. such as antibacterial, anticancer, antihepatotoxic, System. And Ecol, 34, 642-644. and anti-HIV Sri Atun, Nurfina Aznam, Retno Arianingrum, Takaya Y., Niwa Masatake, 2008. Journal of Physical Science, Vol. 19, No. 2, (in press) Sri Atun, 2009, Hopheaphenol –O-glycoside, a References compounds isolated from stem bark Anisoptera marginata (Dipterocarpaceae), Cronquist A. 1981. An Integrated System of Indo. J. Chem, 6 (1), 151-157. Classification of Flowering Plants, Columbia In Press, New York, 316 – 318. Dai, J.R., Y.F Hallock., J.H. Cardellina , M.R. Boyd 1998, HIV-Inhihibitory and cytotoxic oligostilbenoids isolated from the leaves of Hopea malibato, J. Nat. Prod., 61, 351- 353. Heyne K. 1987, Tumbuhan berguna Indonesia, Badan Litbang Kehutanan, Jakarta, jilid III, 1390 – 1443. Ito, T, T. Tanaka, Y. Ido; K. Nakaya, M. Linuma, S. Riswan 2000a, Stilbenoids isolated from stem bark of Shorea hemsleyana, Chem. Pharm. Bull. 48, 1001-1005. Ito T., T. Tanaka, Y. Ido, K. Nakaya, M. Iinuma, S. Riswan 2000b, Four new stilbene C- glycosides isolated from the stem bark of Shorea hemsleyana, Chem. Pharm. Bull. 48, 1959-1963 Sotheeswaran, S., M.U.S. Sultanbawa, S. Surendrakumar, P. Bladon 1983, .
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