A new xanthone named sydoxanthone C (1) and a new alkaloid named acremolin B (2), together with 10 known compounds (3–12) were isolated from a deep-sea-derived fungus Aspergillus sp. SCSIO Ind09F01. The structures of compounds (1–12) were determined by the extensive 1D, 2D-NMR, High resolution mass spectra (HRESIMS) data. Compounds 7, 8, 11 and 12 showed significant selective cytotoxicities against HeLa, DU145 and U937 cell lines. In addition, compounds 7, 8 and 11 also exhibited COX-2 inhibitory activities with the prominent IC50 values of 2.4, 7.1 and 10.6 μM, respectively.
Access optionsAccess options
Subscribe to Journal
Get full journal access for 1 year
only $27.17 per issue
All prices are NET prices.
VAT will be added later in the checkout.
Rent or Buy article
Get time limited or full article access on ReadCube.
All prices are NET prices.
Blunt, J.W., Copp, B. R., Keyzers, R. A., Munro, M. H. & Prinsep, M. R. Marine natural products. Nat. Prod. Rep. 31, 160–258 (2014).
Proksch, P., Putz, A., Ortlepp, S., Kjer, J. & Bayer, M. Bioactive natural products from marine sponges and fungal endophytes. Phytochem. Rev. 9, 475–489 (2010).
Rateb, M. E. & Ebel, R. Secondary metabolites of fungi from marine habitats. Nat. Prod. Rep. 28, 290–344 (2011).
Swathi, J., Narendra, K., Sowjanya, K. & Satya, A. K. Marine fungal metabolites as a rich source of bioactive compounds. Afr. J. Biochem. Res 7, 184–196 (2013).
Lin, X. et al. A new cytotoxic sesquiterpene quinone produced by Penicillium sp. F00120 isolated from a deep sea sediment sample. Mar. Drugs 10, 106–115 (2012).
Song, X. Q. et al. Xanthone derivatives from Aspergillus sydowii, an endophytic fungus from the liverwort Scapania ciliate S. Lac and their immunosuppressive activities. Phytochem. Lett 6, 318–321 (2013).
Yao, Q. et al. Cytotoxic polyketides from the deep-sea-derived fungus Engyodontium album DFFSCS021. Mar. Drugs 12, 5902–5915 (2014).
Hamasaki, T., Sato, Y. & Hatsuda, Y. Structure of sydowinin A, sydowinin B, and sydowinol, metabolites from Aspergillus sydowi.. Agri. Biol. Chem. 39, 2341–2345 (1975).
Januar, L. A. & Molinski, T. F. Acremolin from Acremonium strictum is N, 2, 3-Etheno-2′-isopropyl-1-methylguanine, not a 1 H-Azirine. Synthesis and Structural Revision. Org. Lett. 15, 2370–2373 (2013).
Yurchenko, A. N. et al. A new meroterpenoid from the marine fungus Aspergillus versicolor (Vuill.) Tirab. Russ. Chem. Bull. 59, 852–856 (2010).
Bunyapaiboonsri, T., Yoiprommarat, S., Intereya, K. & Kocharin, K. New diphenyl ethers from the insect pathogenic fungus Cordyceps sp. BCC 1861. Chem. Pharm. Bull. 55, 304–307 (2007).
Chen, M. et al. Bioactive indole alkaloids and phenyl Ether derivatives from a marine-derived Aspergillus sp. fungus. J. Nat. Prod. 76, 547–553 (2013).
Gong, D. L. et al. Diphenyl etheric metabolites from Streptomyces sp. neau50. J. Antibiot. 64, 465–467 (2011).
Takenaka, Y., Hamada, N. & Tanahashi, T. Monomeric and dimeric dibenzofurans from cultured mycobionts of Lecanora iseana. Phytochemistry 66, 665–668 (2005).
Kim, H. S. et al. A novel dihydroxan-thenone, AGI-B4 with inhibition of VEGF-induced endothelial cell growth. J. Antibiot. 55, 669–672 (2002).
Bergeron, J. J. M., Brenner, M. B., Thomas, D.Y. & Williams, D. B. Calnexin: a membrane bound chaperone of the endoplasmic reticulum. Trends Biochem. Sci. 19, 124–128 (1994).
Praveen Rao, P. N. & Edward, E. K. Evolution of nonsteroidal anti-inflammatory drugs (NSAIDs): Cyclooxygenase (COX) inhibition and beyond. J. Pharm. Pharmaceut. Sci 11, 81–110 (2008).
Blobaum, A. L. et al. The 2′-Trifluoromethyl analogue of indomethacin is a potent and selective COX-2 inhibitor. ACS Med. Chem. Lett. 4, 486–490 (2013).
This work was supported by grants from the National Key Basic Research Program of China (973)’s Project (2011CB915503); the National High Technology Research and Development Program (863 Program, 2012AA092104), Strategic Priority Research Program of the Chinese Academy of Sciences (Grant No. XDA11030403), the National Natural Science Foundation of China (31270402, 21172230, 41476135, 41376162, 41406187, 41406187); and Guangdong Marine Economic Development and Innovation of Regional Demonstration Project (GD2012-D01-001), Guangzhou Scientific Research Project (2014J4100212).
The authors declare no conflict of interest.
Supplementary Information accompanies the paper on The Journal of Antibiotics website
About this article
A problem in the structure assignment of acremolin C, which is most probably identical with acremolin B
Natural Product Research (2019)
The Natural Products Journal (2019)
Marine Drugs (2018)
Marine Drugs (2018)