Neuraminidase Inhibitory Polyketides from the Marine-derived Fungus Phoma herbarum

Abstract

Two new polyketides, arthropsadiol C (1) and massarilactone H (2), together with six known derivatives (3–8) were isolated from the culture broth of the marine-derived fungus Phoma herbarum. Their structures were elucidated on the basis of spectroscopic methods, including 2D NMR techniques. Compounds 2, 4, 5, and 8 showed moderate neuraminidase inhibitory activity with IC₅₀ values ranging from 4.15 to 9.16 µM.

Key words

Phoma herbarum - Valsaceae - polyketide - marine fungus - neuraminidase inhibitor

References

• 1 Rateb M E, Ebel R. Secondary metabolites of fungi from marine habitats.  Nat Prod Rep. 2011;  28 290-344
• 2 Osterhage C, Schwibbe M, Konig G M, Wright A D. Differences between marine and terrestrial Phoma species as determined by HPLC-DAD and HPLC-MS.  Phytochem Anal. 2000;  11 288-294
• 3 Alvi K A, Nair B, Pu H, Ursino R, Gallo C, Mocek U. Phomacins: three novel antitumor cytochalasan constituents produced by a Phoma sp.  J Org Chem. 1997;  62 2148-2151
• 4 Ondeyka J G, Zink D L, Young K, Painter R, Kodali S, Galgoci A, Collado J, Tormo J R, Basilio A, Vicente F, Wang J, Singh S B. Discovery of bacterial fatty acid synthase inhibitors from a Phoma species as antimicrobial agents using a new antisense-based strategy.  J Nat Prod. 2006;  69 377-380
• 5 Singh S B, Ball R G, Zink D L, Monaghan R L, Polishook J D, Sanchez M, Pelaez F, Silverman K C, Lingham R B. Fusidienol A: A Novel Ras Farnesyl-Protein Transferase Inhibitor from Phoma sp.  J Org Chem. 1997;  62 7485-7488
• 6 Osterhage C, Konig G M, Jones P G, Wright A D. 5-hydroxyramulosin, a new natural product produced by Phoma tropica, a marine-derived fungus isolated from the alga Fucus spiralis.  Planta Med. 2002;  68 1052-1054
• 7 Herath K, Harris G, Jayasuriya H, Zink D, Smith S, Vicente F, Bills G, Collado J, Gonzalez A, Jiang B, Kahn J N, Galuska S, Giacobbe R, Abruzzo G, Hickey E, Liberator P, Xu D M, Roemer T, Singh S B. Isolation, structure and biological activity of phomafungin, a cyclic lipodepsipeptide from a widespread tropical Phoma sp.  Bioorg Med Chem. 2009;  17 1361-1369
• 8 Sugano M, Sato A, Iijima Y, Oshima T, Furuya K, Kuwano H, Hata T, Hanzawa H. Phomactin A – a novel PAF antagonist from a marine fungus Phoma sp.  J Am Chem Soc. 1991;  113 5463-5464
• 9 Liu C H, Liu J Y, Huang L L, Zou W X, Tan R X. Absolute configuration of keisslone, a new antimicrobial metabolite from Keissleriella sp. YS4108, a marine filamentous fungus.  Planta Med. 2003;  69 481-483
• 10 Ge H M, Yan W, Guo Z K, Luo Q O, Feng R, Zang L Y, Shen Y, Jiao R H, Xu Q A, Tan R X. Precursor-directed fungal generation of novel halogenated chaetoglobosins with more preferable immunosuppressive action.  Chem Commun. 2011;  47 2321-2323
• 11 Liu J Y, Huang L L, Ye Y H, Zou W X, Guo Z J, Tan R X. Antifungal and new metabolites of Myrothecium sp. Z16, a fungus associated with white croaker Argyrosomus argentatus.  J Appl Microbiol. 2006;  100 195-202
• 12 Oh H, Swenson D C, Gloer J B, Shearer C A. Massarilactones A and B: novel secondary metabolites from the freshwater aquatic fungus Massarina tunicata.  Tetrahedron Lett. 2001;  42 975-977
• 13 Krohn K, Ullah Z, Hussain H, Florke U, Schulz B, Draeger S, Pescitelli G, Salvadori P, Antus S, Kurtan T. Massarilactones E–G, new metabolites from the endophytic fungus Coniothyrium sp., associated with the plant Artimisia maritima.  Chirality. 2007;  19 464-470
• 14 Oh H, Swenson D C, Gloer J B, Shearer C A. New bioactive rosigenin analogues and aromatic polyketide metabolites from the freshwater aquatic fungus Massarina tunicata.  J Nat Prod. 2003;  66 73-79
• 15 Lin Y C, Wu X Y, Deng Z J, Wang J, Zhou S N, Vrijmoed L L P, Jones E B G. The metabolites of the mangrove fungus Verruculina enalia No. 2606 from a salt lake in the Bahamas.  Phytochemistry. 2002;  59 469-471
• 16 Ayer W A, Craw P A. Biosynthesis and biogenetic interrelationships of metabolites of the fungus Arthropsis truncata.  Can J Chem. 1992;  70 1348-1355
• 17 Sandmeier P, Tamm C. Studies on the biosynthesis of spirostaphylotrichin A.  Helv Chim Acta. 1989;  72 774-783