Abstract
Nigrosporanenes A (1) and B (2), two new cylohexene derivatives, and tyrosol (3) were isolated from the sea fan-derived fungus Nigrospora sp. PSU-F11, whereas five known compounds: 4-hydroxybenzoic acid (4), aplysiopsene D (5), 3-isochromanone (6), (−)-drimenin (7) and diketopiperazine derivative (8), were obtained from the fungus Nigrospora sp. PSU-F12. Their structures were established by spectroscopic evidence. We also tested their cytotoxic (on African green monkey kidney fibroblast and breast cancer cells), antioxidant (in the DPPH assay), and antibacterial (against the standard Staphylococcus aureus ATCC 25923 and methicillinresistant S. aureus) activities.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
Akita, H., Nozawa, M., Mitsuda, A., and Ohsawa, H., A convenient synthesis of (+)-albicanol based on enzymatic function: total syntheses of (+)-albicanyl acetate, (−)-albicanyl 3,4-dihydroxycinnamate, (−)-drimenol, (−)-drimenin and (−)-ambrox. Tetrahedron: Asymmetry, 11, 1375–1388 (2000).
Allouche, N., Apel, C., Martin, M.-T., Dumontet, V., Guéritte, F., and Litaudon, M., Cytotoxic sesquiterpenoids from Winteraceae of Caledonian rainforest. Phytochemistry, 70, 546–553 (2009).
Almena, J., Foubelo, F., and Yus, M., 1,2-Di(lithiomethyl) benzene from phthalan: sequential introduction of two different electrophiles. Tetrahedron, 51, 3351–3364 (1995).
Ayer, W. A. and Craw, P. A., Biosynthesis and biogenetic interrelationships of metabolites of the fungus Arthropsis truncata. Can. J. Chem., 70, 1348–1355 (1992).
Ayer, W. A., Craw, P. A., and Neary, J., Metabolites of the fungus Arthropsis truncata. Can. J. Chem., 70, 1338–1347 (1992).
Barnett, H. L. and Hunter B. B., Illustrated genera of imperfect fungi. Prentice-Hall Inc., The American Phytopathological Society, USA, (1998).
Chu, M., Mierzwa, R., Truumees, I., Gentile, F., Patel, M., Gullo, V., Chan, T.-M., and Puar, M. S., Two novel diketopiperazines isolated from the fungus Tolypocladium sp. Tetrahedron Lett., 34, 7537–7540 (1993).
Ciavatta, M. L., Manzo, E., Nuzzo, G., Villani, G., Cimino, G., Cervera, J. L., Malaquias, M. A. E., and Gavagnin, M., Aplysiopsenes: an additional example of marine polyketides with a mixed acetate/propionate pathway. Tetrahedron Lett., 50, 527–529 (2009).
Fukushima, T., Tanaka, M., Gohbara, M., and Fujimori, T., Phytotoxicity of three lactones from Nigrospora sacchari. Phytochemistry, 48, 625–630 (1998).
Hashimoto, M., Tsushima, T., Murakami, T., Nomiya, M., Takada, N., and Tanaka, K., Spiroleptosphol isolated from Leptosphaeria doliolum. Bioorg. Med. Chem. Lett., 18, 4228–4231 (2008).
Jolad, S. D., Hoffmann, J. J., Schram, K. H., Cole, J. R., Tempesta, M. S., and Bates, R. B., Structures of zeylenol and zeylena, constituents of Uvaria zeylanica (Annonaceae). J. Org. Chem., 46, 4267–4272 (1981).
Lorian, V., Antibiotics in Laboratory Medicine. William and Wilkins, Baltimore, pp. 28–32, (1996).
Michaelis, M., Langer, K., Vogel, J.-U., Kreuter, J., Rabenau, H., Doerr, H.-W., and Cinatl, J., In vitro antiviral activity of aphidicolin and its derivates: synergistic effects of aphidicolin with other antiviral drugs. Arzneimittelforschung, 52, 393–399 (2002).
Murakami, T., Tsushima, T., Takada, N., Tanaka, K., Nihei, K., Miura, T., and Hashimoto, M., Four analogues of spiroleptosphol isolated from Leptosphaeria doliolum. Bioorg. Med. Chem., 17, 492–495 (2009).
Pyo, M. K., Koo, Y. K., and Yun-Choi, H. S., Anti-platelet effect of the phenolic constituents isolated from the leaves of Magnolia obovata. Nat. Prod. Sci., 8, 147–151 (2002).
Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82, 1107–1112 (1990).
Starratt, A. N. and Loschiavo, S. R., Production of aphidicolin by Nigrospora sphaerica. Can. J. Microbiol., 20, 416–417 (1974).
Tanaka, M., Fukushima, T., Tsujino, Y., and Fujimori, T., Nigrosporins A and B, new phytotoxic and antibacterial metabolites produced by a fungus Nigrospora oryzae. Biosci. Biotechnol. Biochem., 61, 1848–1852 (1997).
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).
Trisuwan, K., Rukachaisirikul, V., Sukpondma, Y., Preedanon, S., Phongpaichit, S., and Sakayaroj, J., Pyrone derivatives from the marine-derived fungus Nigrospora sp. PSU-F18. Phytochemistry, 70, 554–557 (2009).
Yen, G.-C. and Hsieh, G.-L., Antioxidant effects of dopamine and related compounds. Biosci. Biotechnol. Biochem., 61, 1646–1649 (1997).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Rukachaisirikul, V., Khamthong, N., Sukpondma, Y. et al. Cyclohexene, diketopiperazine, lactone and phenol derivatives from the sea fan-derived fungi Nigrospora sp. PSU-F11 and PSU-F12. Arch. Pharm. Res. 33, 375–380 (2010). https://doi.org/10.1007/s12272-010-0305-3
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s12272-010-0305-3