A Structure-Activity Study of Antioxidant Compounds from the Stem Bark of Kandis Gaj ah (Garcinia griffithii T. Anders)

  • ELFITA ELFITA UNIVERSITAS SRIWIJAYA
  • DACHRIYANUS DACHRIYANUS UNIVERSITAS ANDALAS
  • SUPRIYATNA SUPRIYATNA UNIVERSITAS PADJADJARAN
  • HUSEIN H. BAHTI UNIVERSITAS PADJADJARAN

Abstract

Four xanthones and two benzophenones from the stem bark of kandis gajah (Garcinia griffithii) by extraction and chromatographic methods have been isolated. The six compounds were determined as: 1,7-dihydroxyxanthone (1), 1,6,7-trihydroxyxanthone (2), 1,6-dihydroxy-3-methoxy-4,7-di-(3-methylbut-2-enyl)xanthone (3), 1,5-dihydroxy-3,6-di-methoxy-2,7-di-(-3-methylbut-2-enyl)xanthone (4), guttipherone I (5), and isoxanthochymol (6). All of the isolated compounds were submitted to antioxidant activity assay using three methods: (i) free radical scavenging method, (ii) xanthine-xanthine oxidase (XO) method, and (iii) nitroblue tetrazolium xanthine oxidase (NBT/ XO). Guttipherone I (5) and isoxanthochymol (6) have strong antioxidant activity (IC50 ≤10.2 µg/mL), 1,6,7-trihydroxyxanthone (2) and 1,6-dihydroxy-3-methoxy-4,7-di-(3-methylbut-2-enyl)xanthone (3) as active compounds (IC50 ≤ 100 µg/mL), while 1,7-dihydroxyxanthone (1) and 1,5-dihydroxy-3,6-dimethoxy-2,7-di-(3-methylbut-2-enyl)xanthone (4) were inactive (IC50 > 100 µg/mL). Base on the data, antioxidant activity of isolated compounds was inhuenced by dihydroxyl groups at ortho position, number of hydroxyl group, and hydroxyl group at para position to C carbonyl at heterocyclic.

References

1. Joseph GS, Jayaprakasha GK, Selvi AT, Jena BS, Sakariah KK. Antiaflatoxigenic and antioxidant activities of Garcinia extracts. Int J Food Microbio. 2005. 101:153-60.

2. Chiang YM, Kuo YH, Oota S, and Fukuyama Y. Xanthones and benzophenones from the stems of Garcinia multiilora. J Nat Prod. 2003. 66: 1070-3.

3. Silva FAM, Borges F, Guimaraes C, Lima JLF, Matos C, Reis S. Phenolic Acids and Derivatives: Studies on the relationship among structure, radical scavenging activity, and physicochemical parameters. J Agri Food Chem. 2000. 48: 2122-6.

4. Ito C, Itoigawa M, Takakura T, Ruangrungsi N, Enjo F, Tokuda H, et al. Chemical constituens of Garcinia fusca: structure elucidation of eight new xanthones and their cancer chemopreventive activity. J Nat Prod. 2003. 66:200-205.

5. Hay AE, Auinond MC, Mallet S, Dumonted V, Litaudon M, Rondeau D, et al. Antioxidant xanthones from Garcinia vieillardi. J Nat Prod. 2004. 67:707-9.

6. Terashima K, Takaya Y, Niwa M. Powerful antioxidative agents based on garcinoic acid from Garcinia kola. Bioorganic and Med Chem. 2002. 10: 1619-25.

7. Heim KE, Tagliaferro AR, Bobilya DJ. Flavonoid antioxidant: chemistry, metabolism and structureactivity relationships. J Nutri Biochem. 2002. 13: 572-84.

8. Yamaguchi F, Saito M, Ariga T, Yoshimura Y, Nakazawa H. Free radical scavenging activity and antiulcer activity ofgarcinol from Garcinia indica fruit rind. JAgri Food Chem. 2000. 48:2320-5.

9. Selvi AT, Joseph GS, Jayaprakasha GK. Inhibition of growth and aflatoxin production in Aspergillus flavus by Garcinia indica extract and its antioxidant activity. Food Microbio. 2003. 20:455-60.

10. Stojanovic S, Sprinz H, Brede O. Efficiency and mechanism of the antioxidant action of trans-resveratrol and its anologues in the radical liposome oxidation. Arch Biochem and Biophys. 2001. 311(1):78-89.

11. Fukumoto LR and Mazza G. Assessing antioxidant and prooxidant activities of phenolic compounds. J Agri Food Chem. 2000. 48:3597-604.

12. Elfita, Supriyatna S, Bahti HH, Dachriyanus. Diprenylated xanthone from the stem bark of Garcinia griffithii. Indo J Chem. 2008. 8(1):97-100.

13. Elfita E, Muharni M, Madyawati L, Darwati D, Ari W, Supriyatna S, et al. Antiplasmodial and other constituents from four Indonesian Garcinia Sp. Phytochemistry. 2009. 70:907-12.

14. Elfita, Supriyatna S, Bahti HH, Dachriyanus. Chemical constituen from the stem bark of Kandis Gajah (Garcinia griffithii T. Anders) and their antioxidant activity. International Seminar on The Role of Chemistry in Industry and Environment, held in UNAND, Padang, 2007.

15. McCune LM and Johns T. Antioxidant Activity in Medicinal Plants Associated with the Symptoms of Diabetes Mellitus Used by the Indigenous Peoples of the North American Boreal Forest. Journal of Ethnopharmacology. 2002. 82: 197-205.

16. Eltita. Santon dan Benzofenon dari Tumbuhan Kandis Gajah (Garcinia griffithii T. Anders) dan Aktivitas Antioksidannya (Disertasi). Bandung: Jurusan Ilmu Kimia Universitas Padjadjaran; 2008. 52-53.

17. Deachathai S, Mahabusaracam W, Phongpacichit S, Taylor WC, Zhang YJ, and Yang CR. Phenolic Compound from the Flowers of Garcinia dulcis. Phytochemistry. 2006. 67: 464-469.
Published
2011-04-30
How to Cite
ELFITA, ELFITA et al. A Structure-Activity Study of Antioxidant Compounds from the Stem Bark of Kandis Gaj ah (Garcinia griffithii T. Anders). JURNAL ILMU KEFARMASIAN INDONESIA, [S.l.], v. 9, n. 1, p. 35-39, apr. 2011. ISSN 2614-6495. Available at: <http://jifi.farmasi.univpancasila.ac.id/index.php/jifi/article/view/323>. Date accessed: 25 feb. 2024.
Section
Articles