Planta Med 2001; 67(4): 335-339
DOI: 10.1055/s-2001-14306
Original Paper
Natural Product Chemistry
© Georg Thieme Verlag Stuttgart · New York

New Antioxidant and Antimicrobial Ellagic Acid Derivatives from Pteleopsis hylodendron

 Atta-Ur-Rahman1 , F. N. Ngounou2 , M. Iqbal Choudhary1, , Shahid Malik1 , Talat Makhmoor1 , M. Nur-E-Alam1 , Seema Zareen1 , D. Lontsi2 , J. F. Ayafor2 , B. L. Sondengam2
  • 1 International Center for Chemical Sciences, H. E. J. Research Institute of Chemistry, University of Karachi, Karachi, Pakistan
  • 2 Department of Organic Chemistry, Faculty of Science, University of Yaounde 1, Yaounde, Cameroon
Further Information

Publication History

May 26, 2000

July 02, 2000

Publication Date:
31 December 2001 (online)

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.

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

Prof. M. Iqbal Choudhary

HEJ Research Institute of Chemistry

University of Karachi

Karachi-75270

Pakistan

Email: zainraa@digicom.net.pk

Fax: +92 21 496 3373, 496 3124

    >