Natural Product Sciences

The Korean Society of Pharmacognosy (한국생약학회)
권호 표지

Chemical Constituents of Helichrysum conglobatum Growing in Egypt

  • El-Ghazooly, Maged G. (Faculty of Pharmacy, Pharmacognosy Department, University of Alexandria, Alexandria, Egypt Chemical Constituents of Egypyian Helichrysum conglobatum) ;
  • El-Lakany, Abdalla M. (Faculty of Pharmacy, Pharmacognosy Department, University of Alexandria, Alexandria, Egypt Chemical Constituents of Egypyian Helichrysum conglobatum) ;
  • Abou-Shoer, Mohamed I. (Faculty of Pharmacy, Pharmacognosy Department, University of Alexandria, Alexandria, Egypt Chemical Constituents of Egypyian Helichrysum conglobatum) ;
  • Aly, Amal H. (Faculty of Pharmacy, Pharmacognosy Department, University of Alexandria, Alexandria, Egypt Chemical Constituents of Egypyian Helichrysum conglobatum)
  • Published : 2003.12.01
Download PDF
⟨ Previous Next ⟩

Abstract

Five aromatic compounds, of which two are new glucosides, and six flavonols were isolated and identified for the first time from the flower heads and aerial shoots of Helichrysum conglobatum (Asteraceae). Their structures were established on the basis of chemical and spectroscopic methods including UV, MS, 1D- and 2D-NMR. Some fractions and isolates were screened for anti-microbial activities. This is the first report of the isolation of the chemical constituents of this species.

Keywords

References

  1. Agrawal, P. K. 'Studies in organic chemistry 39. Carbon-I3 NMR of flavonoids', Elsevier, Amsterdam, Oxford, New York, Tokyo (1989)
  2. Asakawa, Y., Toyota, M. and Harrison, L. J. 'Isotachin A and isotachin B, two sulphur-containing acrylates from the liverwort Isotachis japonica', Phytochemistry, 24(7), 1505-1508 (1985) https://doi.org/10.1016/S0031-9422(00)81055-9
  3. Benayache, S., Benayache, F., Dendougui, H. and Jay, M., Les Flavonoides dlnula viscosa L.. Plant. Med. Phytother., 25(4), 170-176 (1991)
  4. Boulos, L., 'Flora of Egypt. Checklist', AI Hadara Publishing, Cairo, Egypt, p. 154 (1995)
  5. Carini, M., Aldini, G., Furlanetto, S., Stefani, R. and Facino, R. M., LC coupled to ion-trap MS for the rapid screening and detection of polyphenol antioxidants from Helichrysum stoechas. J. Pharm. Biomed. Anal., 24(3), 517-526 (2001) https://doi.org/10.1016/S0731-7085(00)00431-3
  6. Coen, M., Engel, R. and Nahrstedt, A., Chavicol$\beta-D$ -glucoside, a phenylpropanoid heteroside,benzyl-$\beta-D$-glucoside and glycosidically bound volatiles from subspecies of Cedronella canariensis. Phytochemistry, 40(1), 149-155 (1995) https://doi.org/10.1016/0031-9422(95)00241-X
  7. Cubukcu, B. and Yuksel, V., Constituents of Anatolian medicinal plants; flavonoids of Helichrysum armenium. J. Nat. Prod., 45(2), 137-139 (1982) https://doi.org/10.1021/np50020a005
  8. Czinner, E., Kery, A., Hagymasi, K., Blazovics, A., Lugasi, A., Szoke, E. and Lemberkovics, E., Biologically active compounds of Helichrysum arenarium (L.) Moench. Eur. J. Drug Metab. Pharmacokinet., 24(4), 309-313 (1999) https://doi.org/10.1007/BF03190038
  9. Czinner, E., Hagymasi, K., Blazovics, A., Kery, A., Szoke, E. and Lemberkovics, E., In vitro antioxidant properties of Helichrysum arenarium (L.) Moench. J. Ethnopharmacol., 73(3), 437-443 (2000). 'Through http://www.bmn.com' https://doi.org/10.1016/S0378-8741(00)00304-4
  10. Czinner, E., Hagymasi, K., Blazovics, A., Kery, A., Szoke, E. and Lemberkovics, E., The in vitro effect of Helichrysi flos on microsomal lipid peroxidation. J. Ethnopharmacol., 77(1), 3135 (2001). 'Through http://www.bmn.com'
  11. De la Puerta, R., Saenz, M. T. and Garcia, M. D., Cytoststic activity against HEp-2 cells and antibacterial activity of essential oil from Helichrysum picardii. Phytother. Res., 7(5), 378-380 (1993). 'Through C.A. 120, 200266z (1994).' https://doi.org/10.1002/ptr.2650070511
  12. Dingeon, B., Automatic assay of blood sugar by Trinder's method. Ann. Biol. Clin. (Paris), 33(1),3-13 (1975)
  13. Grande, M., Piera, F., Cuenca, A., Torres, P., and Bellido, I. S., Flavonoids from Inula viscosa. Planta Med., 414-419 (1985)
  14. Harborne, J. B., Mabry, T. J. and Mabry, H., 'The flavonoids', Vol. 2, Academic press, New York and San Francisco, p. 923-947 (1975)
  15. Itokawa, H., Oshida, Y., Ikuta, A., Inatomi, H. and Adachi, T., Phenolic plant growth inhibitors from the flowers of Cucurbita pepo. Phytochemistry, 21 (8),1935-1937 (1982) https://doi.org/10.1016/0031-9422(82)83018-5
  16. Jain, S. R. and Kar, A., The antibacterial activity of some essential oils and their combinations. Planta Med., 20 (2), 118-123 (1971) https://doi.org/10.1055/s-0028-1099675
  17. Kaouadji, M., Acylated and non-acylated kaempferol monoglycosides from Platanus acerifolia buds. Phytochemistry, 29(7), 2295-2297 (1990) https://doi.org/10.1016/0031-9422(90)83055-6
  18. Kobata, K., Sutoh, K., Todo, T., Yazawa, S., Iwai, K. and Watanabe, T., Nordihydrocapsiate, a new capsinoid from the fruits of a nonpungent pepper, Capsicum annuum. J. Nat. Prod.,62,335-336 (1999) https://doi.org/10.1021/np9803373
  19. Liu, Q., Markham, K. R., Pare, P. W., Dixon, R. A. and Mabry, T. J., Flavonoids from elicitor-treated cell suspension cultures of Cephalocereus senilis. Phytochemistry, 32(4), 925-928 (1993) https://doi.org/10.1016/0031-9422(93)85230-O
  20. Liu, Q., Liu, M., Mabry, T. J. and Dixon, R. A., Flavonol glycosides from Cephalocereus senilis. Phytochemistry, 36(1), 229-231 (1994) https://doi.org/10.1016/S0031-9422(00)97043-2
  21. Lott, J. A., Evaluation of Trinder's glucose oxidase method for measuring glucose in serum and urine. Clin. Chem., 21(12), 1754-1760 (1975)
  22. Mabry, T. J., Markham, K. R. and Thomas, M. B., 'The systematic identification of flavonoids', Springer-Verlag, Berlin, Heidelberg, New York (1970)
  23. Manitto, P., Monti, D. and Colombo, E., Two new $\beta$-diketones from Helichrysum italicum. Phytochemistry, 11(6), 2112-2114 (1972) https://doi.org/10.1016/S0031-9422(00)90186-9
  24. Markham, K. R., Temai, B., Stanley, R., Geiger, H. and Mabry, T. J., Carbon-13 NMR studies of flavonoids-Ⅲ: Naturally occurring flavonoid glycosides and their acylated derivatives. Tetrahedron, 34, 1389-1397 (1978) https://doi.org/10.1016/0040-4020(78)88336-7
  25. Markham, K. R., Vilain, C. and Molloy, B. P. J., Uniformity and distinctness of Phyllocladus as evidenced by flavonoid accumulation. Phytochemistry, 24(11), 2607-2609 (1985) https://doi.org/10.1016/S0031-9422(00)80678-0
  26. Optiz, L., Ohlendorf, D. and Haensel, R., 5,7-dihydroxy-3,8-dimethoxyflavone from Helichrysum italicum. Phytochemistry, 10(8), 1948 (1971) https://doi.org/10.1016/S0031-9422(00)86473-0
  27. Pouchet, C. J. and Behnke, J., 'The Aldrich Library $of^{13}C$ and $^1H$ FT NMR spectra', 1st ed., Aldrich Chemical Company Inc. (1993)
  28. Ross, S. A., Myricetin-3'-methyl ether-7-glucoside from Limonium sinuatum. J. Nat. Prod., 47(5), 862-864 (1984) https://doi.org/10.1021/np50035a019
  29. Singh, K. N. and Pandey, V. B., Isorhamnetin 7-g1ucoside from Cnicus wallichi. Phytochemistry, 25(11), 2683 (1986) https://doi.org/10.1016/S0031-9422(00)84544-6
  30. Skakun, N. P. and Stepanova, N. Yu., Comparative evaluation of the hepatoprotective, antioxidant and choleretic activity of flavonoid drugs. Vrach. Delo, (12), 52-54 (1988). 'Through C.A. 110, 128601d (1989).'
  31. Tackholm, V., 'Students flora of Egypt', 2nd ed., Cooperative Printing Company, Beirut, p. 559 (1974)
  32. Terasawa, N., Yamazaki, N. and Fnkui, Y.,Antioxidative activity of water extracts of herbs. Nippon Shokuhin Kagaku Kogaku Kaishi, 48(2),99-104 (2001). 'Through C.A. 134, 221731b (2001)'. https://doi.org/10.3136/nskkk.48.99
  33. Thomas, M. B. and Mabry, T. J., Flavonoid constituents of Hymenoxys scaposa DC. (Compositae). Phytochemistry, 7, 787-790 (1968) https://doi.org/10.1016/S0031-9422(00)84833-5
  34. Van Puyvelde, L., De Kimpe, N., Costa, J., Munyjabo, V., Nyirankuliza, S., Hakizamungu, E. and Schamp, N., Isolation of flavonoids and a chalcone from Helichrysum odoratissimum and synthesis of helichrysetin. J. Nat. Prod., 52(3), 629-633 (1989) https://doi.org/10.1021/np50063a025
  35. Wagner, H., Chari, V. M. and Sonnenbichler, J.,$^{13}C$ -NMR-Spektren naturlich vorkommender Flavonoide. Tetrahedron Lett., (21),1799-1802 (1976)
  36. Watt, J. M. and Breyer-Brandwijk, M. G., 'The medicinal and poisonous plants of southern and eastern Africa', 2nd ed., E. and S. Livingstone, Edinburgh and London, p. 237-240 (1962)