Abstract
Investigation of secondary metabolites from the sea fan-derived fungus Curvularia sp. PSU-F22 resulted in isolation of three new metabolites, curvulapyrone (1), curvulalide (2) and curvulalic acid (3) together with six known compounds, modiolides A (4) and B (5), pyrenolide A (6), stagonolide E (7), mycoepoxydiene (8), and deacetylmycoepoxydiene (9). Their antimicrobial activity against Staphylococcus aureus ATCC 25923, methicillin-resistant S. aureus and Microsporum gypseum SH-MU-4 were examined.
Similar content being viewed by others
References
Clinical and Laboratory Standards Institute (CLSI). Reference method for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved standard M7-A4. Clinical and Laboratory Standards Institute, Wayne, Pa, (2002a).
Clinical and Laboratory Standards Institute (CLSI). Reference method for broth dilution antifungal susceptibility testing of yeasts. Approved standard, 2nd ed, M27-A4. Clinical and Laboratory Standards Institute, Wayne, Pa, (2002b).
Clinical and Laboratory Standards Institute (CLSI). Reference method for broth dilution antifungal susceptibility testing of filamentous fungi. Approved standard. CLSI document M38-A. Clinical and Laboratory Standards Institute, Wayne, Pa, (2002c).
Drummond, A. J. and Waigh, R. D., The development of microbiological methods for phytochemical screening. Recent Research Developments in Phytochemistry, 4, pp. 143–152, (2000).
Evidente, A., Cimmino, A., Berestetskiy, A., Mitina, G., Andolfi, A., and Motta, A., Stagonolides B-F, nonenolides produced by Stagonospora cirsii, a potential mycoherbicide of Cirsium arvense. J. Nat. Prod., 71, 31–34 (2008).
Greve, H., Schupp, P. J., Eguereva, E., Kehraus, S., Kelter, G., Maier, A., Fiebig, H. -H., and König, G. M., Apralactone A and a new stereochemical class of curvularins from the marine fungus Curvularia sp. Eur. J. Org. Chem., 2008, 5085–5092 (2008).
Greve, H., Schupp, P. J., Eguereva, E., Kehraus, S., and König, G. M., Ten-membered lactones from the marine-derived fungus Curvularia sp. J. Nat. Prod., 71, 1651–1653 (2008).
Jadulco, R., Brauers, G., Edrada, R. A., Ebel, R., Wray, V., Sudarsono, S., and Proksch, P., New metabolites from sponge-derived fungi Curvularia lunata and Cladosporium herbarum. J. Nat. Prod., 65, 730–733 (2002).
Jones, G. B., Huber, R. S., and Chapman, B. J., Catalytic enantioselective synthesis of macrolides via asymmetric alkylation. Tetrahedron: Asymmetry, 8, 1797–1809 (1997).
Kim, J. -C., Choi, G. J., Kim, H. T., Kim, H. -J., and Cho, K. Y., Pathogenicity and pyrenocine production of Curvularia inaequalis isolated from zoysia grass. Plant Disease, 84, 684–688 (2000).
Lee, J. C., Yang, X., Schwartz, M., Strobel, G., and Clardy, J., The relationship between an endangered North American tree and an endophytic fungus. Chem. Biol., 2, 721–727 (1995).
Nukina, M., Sassa, T., and Ikeda, M., A new fungal morphogenic substance, pyrenolide A from Pyrenophora teres. Tetrahedron Lett., 21, 301–302 (1980).
Sommart, U., Rukachaisirikul, V., Sukpondma, Y., Phongpaichit, S., Towatana, N. H., Graidist, P., Hajiwangoh, Z., and Sakayaroj, J., A cyclohexenone derivative from Diaporthaceous fungus PSU-H2. Arch. Pharm. Res., 32, 1227–1231 (2009).
Teles, H. L., Silva, G. H., Castro-Gamboa, I., Bolzani, V. S., Pereira, J. O., Costa-Neto, C. M., Haddad, R., Eberlin, M. N., Young, M. C. M., and Araújo, Â. R., Benzopyrans from Curvularia sp., an endophytic fungus associated with Ocotea corymbosa (Lauraceae). Phytochemistry, 66, 2363–2367 (2005).
Trisuwan, K., Rukachaisirikul, V., Sukpondma, Y., Preedanon, S., Phongpaichit, S., Rungjindamai, N., and Sakayaroj, J., Epoxydons and a pyrone from the marine-derived fungus Nigrospora sp. PSU-F5. J. Nat. Prod., 71, 1323–1326 (2008).
Tsuda, M., Mugishima, T., Komatsu, K., Sone, T., Tanaka, M., Mikami, Y., and Kobayashi, J., Modiolides A and B, two new 10-membered macrolides from a marine-derived fungus. J. Nat. Prod., 66, 412–415 (2003).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Trisuwan, K., Rukachaisirikul, V., Phongpaichit, S. et al. Modiolide and pyrone derivatives from the sea fan-derived fungus Curvularia sp. PSU-F22. Arch. Pharm. Res. 34, 709–714 (2011). https://doi.org/10.1007/s12272-011-0502-8
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-011-0502-8