New Antioxidant and Antimicrobial Ellagic Acid Derivatives from Pteleopsis hylodendron

Abstract

Bioassay-guided isolation of two new compounds, 3,4-methylenedioxy-3′-O-methyl-4′-O-glucoside ellagic acid (1) and the pteleoellagic acid derivative (2), from the stem bark of Pteleopsis hylodendron is reported along with 3,4-methylenedioxy-3′-O-methyl ellagic acid (3), 3,3′-di-O-methyl ellagic acid (4) and 3,3′,4′-tri-O-methyl ellagic acid (5), which were obtained for the first time from this plant. The structures of these compounds were elucidated with the help of spectroscopic studies. Compounds 1 and 4 were found to have significant antioxidant activity, while compounds 1 - 4 showed antibacterial activity against different pathogenic bacteria.

Key words

Pteleopsis hylodendron - Combretaceae - ellagic acids - antioxidant - antibacterial

References

• 1 Irvine F R. Woody Plants of Ghana. London; Oxford University Press 1961: 127-9
• 2 Liben L. Flore du Cameroun. Cameroon; DGRST, Yaounde 1983: 12-5
• 3 Ngounou N F, Atta-ur- Rahman, Choudhary M I, Malik S, Zareen S, Ali R, Lonsti D et al. New saponins from Pteleopsis hylodendron .  Phytochemistry. 1999;  52 917-21
• 4 Smith R C, Reeves J C, Dage R C, Schnettler R A. Antioxidant properties of 2-Imidazolones and 2-Midazolthiones.  Biochem. Pharmacol.. 1987;  36 1457-60
• 5 Fujita Y, Uehara I, Morimoto Y, Nakashima M, Hatano T, Okuda T. Studies on inhibition mechanism of autoxidation by tannins and flavonoids. II. Inhibition mechanism of caffeetannins isolated from leaves of Artemisia species on lipoxygenase dependent lipid peroxdation.  Yakugaku Zasshi. 1988;  108 129-35
• 6 Atta-ur- Rahman, Choudhary M I, Thomsen W J. Manual of Bioassay Techniques for Natural Product Research. Amsterdam; Harward Academic Press 2000 (in press):
• 7 Jurd L. The structure of ellagorubin.  J. Am. Chem. Soc.. 1959;  81 4610-5
• 8 Sato T. Spectral differentiation of 3,3′-di-O-methylellagic acid from 4,4′-di-O-methylellagic acid.  Phytochemistry. 1987;  26 2124-5
• 9 Yang S, Zhou B, Wisse J H, Evans R, Werf H, Miller J S, Kingston D GI. Three new ellagic acid derivatives from the bark of Eschweilera coriacea from the Suriname rainforest.  J. Nat. Prod.. 1998;  61 901-6
• 10 Correa B D, Birchal E, Aguilar V J, Gottlieb O R. Ellagic acids from Vochysiaceae.  Phytochemistry. 1975;  14 1138-9
• 11 Row R, Raju R R. Isolation of 3,4,3′-O-trimethylflavellagic acid from Terminalia paniculata Roth.  Tetrahedron. 1967;  23 879-84
• 12 Correa B D, Guerra B FL, De-Padua P A, Gottlieb R O. Ellagic acids from Callisthene major .  . Phytochemistry. 1985;  24 1860-1
• 13 Khac D D, Tran-Van S, Campos M A, Lallemand J, Fetizon M. Ellagic compounds from Diplopanax stachyanthus .  Phytochemistry. 1990;  29 251-5
• 14 Bindra S R, Satti K N, Suri P O. Isolation and structures of ellagic acid derivatives from Euphorbia acaulis .  Phytochemistry. 1988;  27 2313-5
• 15 Choi Y, Pezzuto M J, Kinghorn D A, Farnsworth R N. Ellagic acid derivatives of Agrostistachys hookeri .  Planta Medica. 1988;  54 511-3
• 16 Pathak M A, Joshi P C. The nature and molecular basis of cutaneous photosensitivity reaction to psoralens and coal tar.  J. Innves. Derm.. 1983;  80 66-74
• 17 Floyd R A. Free-radical events in chemical and biochemical reactions involving carcinogenic arylamines.  Radiat. Res.. 1981;  86 243-5
• 18 Floyd R A. DNA-ferrous iron catalyzed hydroxyl free radical formation from hydrogen peroxide.  Biochem. Biophys. Res. Commun.. 1981;  99 1209-15
• 19 Steinberg D, Parthasarathy S, Carew T E, Khoo J C, Witztem J L. Beyond cholesterol. Modifications of low-density lipoprotein that increase its atherogenicity.  New Engl. J. Med.. 1989;  320 915-24
• 20 Janssen Y MW, van Houten B, Borm P JA, Mossman B T. Cell and tissue responses to oxidative damage.  Lab. Invest.. 1993;  69 261-74
• 21 Yu B P. Cellular defenses against damage from reactive oxygen species.  Biol. Rev.. 1994;  74 139-62
• 22 Fischer-Nielsen A, Jeding I B, Loft S. Radiation induced formation of 8-hydroxy-2′-deoxyguanosine and its prunention by scavengers.  Carcinogenesis. 1994;  15 1606-12