Abstract
Amentoflavone is a plant biflavonoid that was isolated from an ethyl acetate extract of the whole plant ofSelaginella tamariscina (Beauv.) spring. 1D and 2D NMR spectroscopy including DEPT, HMQC, and HMBC were used to determine its structure. Amentoflavone exhibited potent antifungal activity against several pathogenic fungal strains but had a very low hemolytic effect on human erythrocytes. In particular, amentoflavone induced the accumulation of intracellular trehalose onC. albicans as a stress response to the drug, and disrupted the dimorphic transition that forms pseudo-hyphae during pathogenesis. In conclusion, amentoflavone has great potential to be a lead compound for the development of antifungal agents.
Article PDF
Similar content being viewed by others
Avoid common mistakes on your manuscript.
References
Attfield, P. V., Trehalose accumulates inSaccharomyces cerevisiae during exposure to agents that induce heat shock response.FEBS Lett., 225, 259–263 (1987).
Baureithel, K. H., Buter, K. B., Engesser, A., Burkard, W., and Schaffner, W., Inhibition of benzodiazepine binding in vitro by amentoflavone, a constituent of various species ofHypericum.Pharm. Acta Helvetica, 72, 153–157 (1997).
Benaroudj, N., Lee, D. H., and Goldberg, A. L., Trehalose accumulation during cellular stress protects cells and cellular proteins from damage by oxygen radicals.J. Biol. Chem., 276, 24261–24267 (1987).
Calerone, R. A. and Fonzi, W. A., Virulence factors ofCandida albicans.Trends Microbiol., 9, 327–335 (2001).
Carlo, G. D., Masclo, N., Izzo, A. A., and Capasso, F., Flavonoids: Old and new aspects of a class of natural therapeutic drugs.Life Sci., 65, 337–353 (1999).
Elbein, A. D., Pan, Y. T., Oastuszak, I., and Carroll, D., New insights on trehalose: a multifunctional molecule.Glycobiology, 13, 17–27 (2003).
Gambhir, S. S., Geol, R. K., and Das Gupta, G., Anti-inflammatory & anti-ulcerogeinc activity of amentoflavone.Indian J. Med. Res., 85, 689–693 (1987).
Gil, B., Sanz, M. J., Terencio, M. C., Gunasegaran, R., Paya, M., and Alcaraz, M. J., Morelloflavone, a novel biflavonoid inhibitor of human secretory phospholipase A2 with antiinflammatory activity.Biochem. Pharmacol., 53, 733–740 (1997).
Kim, H. K., Son, K. H., Chang, H. W., Kang, S. S., and Kim, H. P., Amentoflavone, a plant biflavone: a new potential antiinflammatory agent.Arch. Pharm. Res., 21, 406–410 (1998).
Kim, H. P., Mani, I., Iversen, L., and Ziboh, V. A., Effects of naturally-occurring flavonoids and biflavonoids on epidermal cyclooxygenase and lipoxygenase form guinea-pigs.Prostaglandins Leukot. Essent. Fatty Acids., 58, 17–24 (1998).
Krauze-Baranowska, M., Cisowski, W., Wiwart, M., and Madziar, B., Antifungal biflavones fromCupressocyparis leylandii.Planta Med., 65, 572–573 (1999).
Krauze-Baranowska, M. and Wiwart, M., Antifungal activity of biflavones fromTaxus baccata andGinkgo biloba.Z Naturforsch [C]., 58, 65–69 (2003).
Lee, D. G., Hahm, K.-S., and Shin, S. Y., Structure and fungicidal activity of a synthetic antimicrobial peptide, P8, and its truncated peptides.Biotech. Lett., 26, 337–341 (2004).
Lee, D. G., Park, Y., Keon, P. I., Jeong, H. G., Woo, E.-R., and Hanm, K.-S., Influence on the plasma membrane ofCandida albicans by HP(2-9)-magainin 2(1-2) hybrid peptide.Biochem. Biophys. Res. Commun. 297, 885–889 (2002).
Lee, H. S., Oh, W. K., Kim, B. Y., Ahn, S. C., Kang, D. O., Shin, D. I., Kim, J., Mheen, T. I., and Ahn, J. S., Inhibition of phospholipase C gamma 1 activity by amentoflavone isolated fromSelaginella tamariscina.Planta Med., 62, 293–296 (1996).
Lin, L., Kuo, U., and Chou, C., Cytotoxic Biflavonoids fromSelaginella delicatula.J. Nat. Prod., 63, 627–630 (2000).
Lin, Y. M., Flavin, M. T., Schure, R., Chen, F. C., Sidwell, R., Barnard, D. L., Huffman, J. H., and Kern, E. R., Antiviral activities of biflavonoids.Planta med., 65, 120–125 (1999).
Lobstein-Guth, A., Briancon-Scheid, F., Victoire, C., Haag-Berrurier, M., and Anton, R., Isolation of amentoflavone fromGinkgo biloba.Planta Med., 54, 555–556 (1998).
Ma, S. C., But, P. P., Ooi, V. E., He, Y. H., Lee, S. H., Lee, S. F., and Lin, R. C., Antiviral amentoflavone fromSelaginella sinensis.Biol. Pharm. Bull., 24, 311–312 (2001).
Markham, K. R., Sheppard, C., and Geiger, H.,13C NMR studies of some naturally occurring amentoflavone and hinokiflavone biflavonoids.Phytochemistry, 26, 3335–3337 (1987).
Matsuoka, S. and Murata, M., Cholesterol markedly reduces ion permeability induced by membrane-bound amphotericin B.Biochim. Biophys. Acta., 1564, 429–434 (2002).
Mclain, N., Ascanio, R., Baker, C., Strohaver, R. A., and Dolan, J. W., Undeclenic acid inhibits morphogenesis ofCandida albicans.Antimicrob. Agents Chemother., 44, 2873–2875 (2000).
Paik, S. K., Yun, H. S., Sohn, H., and Jin, I., Effect of trehalose accumulation on the intrinsic and acquired thermotolerance on a natural isolateSaccharomyces cerevisiae KNU5377.J. Microbiol. Biotechnol., 13, 85–89 (2003).
Schulze, U., Larsen, M. E., and Villadsen, J., Determination of intracellular trehalose and glycogen inSaccharomyces cerevisiae.Anal. Biochem., 228, 143–149 (1995).
Sengupta, S., Jana, M. L., Sengupta, D., and Naskar, A. K., A note on the estimation of microbial glycosidase activities by dinitrosalicylic acid reagent.Appl. Microbiol. Biotech., 53, 732–735 (2000).
Shin, S. Y., Kang, S., Lee, D. G., Eom S. H., Song, W. K., and Kim, J. I., CRAMP analogues having potent antibiotic activity against bacterial, fungal, and tumor cells without hemolytic activity.Biochem. Biophys. Res. Commun., 275, 904–909 (2000).
Silva, G. L., Chai, H., Gupta, M. P., Farnsworth, N. R., Cordell, G. A., Pezzuto, J. M., Beecher, C. W., and Kinghorn, A. D., Cytotoxic biflavonoids fromSelaginella willdenowii.Phytochemistry, 40, 129–134 (1995).
Woo, E.-R., Lee, J. Y., Cho, I. J., Kim, S. G., and Kang, K. W., Amentoflavone inhibits the induction of nitric oxide synthase by inhibiting NF-kappaB activation in macrophages.Pharmacol. Res., 51, 539–546 (2005).
Author information
Authors and Affiliations
Corresponding authors
Rights and permissions
About this article
Cite this article
Jung, H.J., Sung, W.S., Yeo, SH. et al. Antifungal effect of amentoflavone derived fromSelaginella tamariscina . Arch Pharm Res 29, 746–751 (2006). https://doi.org/10.1007/BF02974074
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02974074