Planta Med 2002; 68(6): 539-541
DOI: 10.1055/s-2002-32547
Letter
© Georg Thieme Verlag Stuttgart · New York

Antiviral and Antioxidant Activity of Flavonoids and Proanthocyanidins from Crataegus sinaica

Abdelaaty A. Shahat1, 2 , Paul Cos2 , Tess De Bruyne2 , Sandra Apers2 , Fayza M. Hammouda1 , Shams I. Ismail1 , Safa Azzam1 , Magda Claeys2 , Etienne Goovaerts3 , Luc Pieters2 , Dirk Vanden Berghe2 , Arnold J. Vlietinck2
  • 1Pharmacognosy and Chemistry of Medicinal Plants Department, NRC, Dokki, Cairo, Egypt
  • 2Faculty of Pharmaceutical Sciences, University of Antwerp, Antwerp, Belgium
  • 3Department of Physics, University of Antwerp, Antwerp, Belgium
Weitere Informationen

Publikationsverlauf

August 16, 2001

October 30, 2001

Publikationsdatum:
01. Juli 2002 (online)

Abstract

The antiviral and antioxidant activity of some fractions and of a series of flavonoids and proanthocyanidins obtained from Crataegus sinaica (Rosaceae) was evaluated. The O-glycosidic flavonoids and the oligomeric proanthocyanidins exhibited significant inhibitory activity against herpes simplex virus type 1 (HSV-1), which was shown to be due to an extracellular mechanism for procyanidin C-1. Procyanidin C-1 also had the highest antioxidant activity in both the microsomal lipid peroxidation and the hydroxyl radical scavenging assay. In addition to the previously reported phenolic compounds, the pentacyclic triterpenoid ursolic acid (1) and a tetrameric (2) and pentameric procyanidin (3) are reported for the first time.

References

  • 1 Shahat A A, Hammouda F, Ismail S I, Azzam S A, De Bruyne T, Lasure A, Van Poel B, Pieters L, Vlietinck A. Anti-complementary activity of Crataegus sinaica .  Planta Medica. 1996;  62 10-3
  • 2 Shahat A A, Hammouda F, Ismail S I, Azzam S A, Lemiere G, De Bruyne T, De Swaef S, Pieters L, Vlietinck A. Anti-HIV activity of flavonoids and proanthocyanidins from Crataegus sinaica .  Phytomedicine. 1998;  5 133-6
  • 3 Bézanger-Beauquesne L, Pinkas M, Torck M, Totin F. Plantes Médicinales des Regions Temperés. Paris; Malsine 1990
  • 4 Loew D. Phytotherapy in heart failure.  Phytomedicine. 1997;  4 267-71
  • 5 Schmidt U, Kuhn U, Ploch M, Hübner W D. Efficacy of the Hawthorn (Crataegus) preparation LI 132 in 78 patients with chronic congestive heart failure defined as NYHA functional class II.  Phytomedicine. 1994;  1 17-24
  • 6 Haslam E. Natural polyphenols (vegetable tannins) as drugs: Possible modes of action.  Journal of Natural Products. 1996;  59 205-15
  • 7 Peterhans E. Oxidants and antioxidants in viral diseases: Disease mechanisms and metabolic regulation.  Journal of Nutrition. 1997;  127 S962-5
  • 8 Lin C N, Chung M I, Gan K H, Chinang J R. Studies on the constituents of Formosan Gentianaceous plants. 9. Xanthones from Formosan Gentianaceous plants.  Phytochemistry. 1987;  26 2381-4
  • 9 Morimito S, Nonaka G, Nishioka I. Tannins and related compounds. 38. Isolation and characterization of flavan-3-ol glucosides and procyanidin oligomers from Cassia bark (Cinnamomum cassia Blume).  Chemical Pharmaceutical Bulletin. 1986;  34 633-42
  • 10 Foo L Y, Karchesy J J. Procyanidin tetramers and pentamers from Douglas-fir bark.  Phytochemistry. 1991;  30 667-70
  • 11 De Bruyne T. Two-dimensional NMR investigation and biological evaluation of dimeric proanthocyanidins and related polyphenols. Ph. D. Thesis. University of Antwerp Belgium; 1995
  • 12 De Bruyne T, Pieters L, Witvrouw M, De Clercq E, Vanden Berghe D, Vlietinck A J. Biological evaluation of proanthocyanidin dimers and related polyphenols.  Journal of Natural Products. 1999;  62 954-8
  • 13 Vanden Berghe D AR, Haemers A, Vlietinck A J. Antiviral agents from higher plants and an example of structure-activity relationship of 3-methoxyflavones. In: Colegate SM., Molyneux RJ., editors Bioactive Natural Products. Boca Raton; CRC Press 1993: 405-40
  • 14 Cos P, Calomme M, Sindambiwe J B, De Bruyne T, Cimanga K, Pieters L, Vlietinck A J, Vanden Berghe D. Cytotoxicity and lipid peroxidation-inhibiting activity of flavonoids.  Planta Medica. 2001;  67 515-9
  • 15 Taira J, Ikemoto T, Yoneya T, Hagi A, Makino K. Essential oil phenyl propanoids.  Useful as ·OH scavengers? Free Radical Research Communications. 1992;  16 197-204
  • 16 Cos P. Ph. D. Thesis. University of Antwerp Antwerp, Belgium; 2001

Prof. Dr. L. Pieters

Department of Pharmaceutical Sciences

University of Antwerp

Universiteitsplein 1

2610 Antwerp, Belgium

eMail: pieters@uia.ua.ac.be

Fax: (+32) 3 820 27 09