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Archives of Pharmacal Research

, Volume 35, Issue 5, pp 761–767 | Cite as

Flavonol triglycoside and investigation of the antioxidant and cell stimulating activities of Annona muricata Linn.

  • Mahmoud NawwarEmail author
  • Nahla Ayoub
  • Sahar Hussein
  • Amani Hashim
  • Reham El-Sharawy
  • Kristian Wende
  • Manuela Harms
  • Ulrike Lindequist
Research Article Drug Design and Discovery

Abstract

Chemical investigation on leaves of Annona muricata resulted in the isolation of the flavonol triglycoside, quercetin 3-O-α-rhamnosyl-(1″″ → 6″)-β-sophoroside, together with twelve known phenolics. The structures of these compounds were established by 1D- and 2D-nuclear magnetic resonance spectroscopic techniques and mass spectrometry data. The in vitro antioxidant studies of the investigated aqueous ethanol extract and its column fractions were accomplished using the oxygen radical absorbance capacity (ORAC) method. A stimulating effect on HaCaT human keratinocytes by the leaf extract was also assessed. Il-6 production after UV irradiation was not influenced by A. muricata leaf extract.

Key words

Annonaceae Annona muricata Quercetin 3-O-rhamnosylsophoroside Antioxidant UV protection 

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References

  1. Baskar, R., Rajeswari, V., and Kumar, T. S., In vitro antioxidant studies in leaves of Annona species. Indian J. Exp. Biol., 45, 480–485 (2007).PubMedGoogle Scholar
  2. Brever, O., Medicinal plants in tropical West Africa. Cambridge University Press, Cambridge, UK (1986).Google Scholar
  3. Kossouoh, C., Moudachirou, M., Adjakidje, V., Chalchat, J. C., and Figuérédo, G., Comparative study of the chemical composition of the leaves and fruits deriving the essential oil of Hyptis suaveolens (L.) Poit. from Benin. J. Essent. Oil Res., 22, 507–509 (2010).CrossRefGoogle Scholar
  4. Leboeuf, M., Cavé, A., Bhaumik, P. K., Mukherjee, B., and Mukherjee, R., The phytochemistry of the annonaceae. Phytochemistry, 21, 2783–2813 (1980).CrossRefGoogle Scholar
  5. Leboeuf, M., Legueut, C., Cavé, A., Desconclois, J. F., Forgacs, P., and Jacquemin, H., Alkaloids of Annonaceae. XXIX. Alkaloids of Annona muricata. Planta Med., 42, 37–44 (1981).PubMedCrossRefGoogle Scholar
  6. Leopoldini, M., Russo, N., and Toscano, M., The molecular basis of working mechanism of natural polyphenolic antioxidants. Food Chem., 125, 288–306 (2011).CrossRefGoogle Scholar
  7. Lindequist, U., Wende, K., Harms, M., Witt, S., Poerksen, J., and Jülich, W. D., Biological and chemical investigations of Ganoderma pfeifferi and possible application of this new medicinal mushroom in cosmetics Conference Proceedings, 5th International Medicinal Mushroom Conference, Nantong, China, September, 615–622 (2009).Google Scholar
  8. Lucas-Abellán, C., Mercader-Ros, M. T., Zafrilla, M. P., Fortea, M. I., Gabaldón, J. A., and Núñez-Delicado, E., ORAC-fluorescein assay to determine the oxygen radical absorbance capacity of resveratrol complexed in cyclodextrins. J. Agric. Food Chem., 56, 2254–2259 (2008).PubMedCrossRefGoogle Scholar
  9. Mabry, T. J., Markham, K. R., and Thomas, M. B., The Systematic Identification of Flavonoids. Springer, Heidelberg, (1970).Google Scholar
  10. Markham, K. R. and Chari, V. M., The Flavonoids: Advances in Research, ed. Harborn, J. B. and Mabry, T. J., Chapman and Hall, London, Chap. 2, (1982).Google Scholar
  11. Nawwar, M. A. M., El-Mousallamy, A. M. D., and Barakat, H. H., Quercetin 3-glycosides from the leaves of Solanum nigrum. Phytochemistry, 28, 1755–1757 (1989).CrossRefGoogle Scholar
  12. N’Gouemo, P., Koudogbo, B., Pambou Tchivounda, H., Akono-Nguema, C., and Etoua, M. M., Effect of ethanol extract of Annona muricata on pentylenetetrazol-induced convulsive seizures in mice. Phytother. Res., 11, 243–245 (1997).CrossRefGoogle Scholar
  13. Pélisser, Y., Marion, C., Kone, D., Lamaty, G., Menut, C., and Besslere, J. M. J., Volatile components of Annona muricata. Essent. Oil Res., 6, 411–414 (1994).CrossRefGoogle Scholar
  14. Rieser, M. J., Fang, X., Anderson, J. E., Miesbauer, L. R., Smith, D. L., and Mclaughlin, J. L., Three new cytotoxic monotetrahydrofuran-ring acetogenins from Annona muricata. Helv. Chim. Acta, 76, 2433–2444 (1993).CrossRefGoogle Scholar
  15. Strack, D., Meurer, B., Wray, V., Grotjahn, L., Austenfeld, F. A., and Wiermann, R., Quercetin 3-glucosylgalactoside from pollen of Corylus avellana. Phytochemistry, 23, 2970–2971 (1984).CrossRefGoogle Scholar
  16. Yuan, S. S., Chang, H. L., Chen, H. W., Yeh, Y. T., Kao, Y. H., Lin, K. H., Wu, Y. C., and Su, J. H., Annonacin, a mono-tetrahydrofuran acetogenin, arrests cancer cells at the G1 phase and causes cytotoxicity in a Bax- and caspase-3-related pathway. Life Sci., 72, 2853–2861 (2003).PubMedCrossRefGoogle Scholar

Copyright information

© The Pharmaceutical Society of Korea and Springer Netherlands 2012

Authors and Affiliations

  • Mahmoud Nawwar
    • 1
    Email author
  • Nahla Ayoub
    • 2
  • Sahar Hussein
    • 1
  • Amani Hashim
    • 1
  • Reham El-Sharawy
    • 1
  • Kristian Wende
    • 3
  • Manuela Harms
    • 3
  • Ulrike Lindequist
    • 3
  1. 1.Department of Phytochemistry and Plant Systematic, Division of Pharmaceutical IndustriesNational Research CenterDokki, CairoEgypt
  2. 2.Department of Pharmacognosy, Faculty of PharmacyAin-Shams UniversityCairoEgypt
  3. 3.Institut für Pharmazie, Pharmazeutische BiologieErnst-Moritz-Arndt-Universität GreifswaldGreifswaldGermany

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