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Chemical profile of the secondary metabolites produced by a deep-sea sediment-derived fungus Penicillium commune SD-118

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Abstract

Bioassay-guided fractionation of the crude extract from Penicillium commune SD-118, a fungus obtained from a deep-sea sediment sample, resulted in the isolation of a known antibacterial compound, xanthocillin X (1), and 14 other known compounds comprising three steroids (2–4), two ceramides (5 and 6), six aromatic compounds (7–12), and three alkaloids (13–15). Xanthocillin X (1) was isolated for the first time from a marine fungus. In the bioassay, xanthocillin X (1) displayed remarkable antimicrobial activity against Staphylococcus aureus and Escherichia coli, and significant cytotoxicity against MCF-7, HepG2, H460, Hela, Du145, and MDA-MB-231 cell lines. Meleagrin (15) exhibited cytotoxicity against HepG2, Hela, Du145, and MDA-MB-231 cell lines. This is the first report of the cytotoxicity of xanthocillin X (1).

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References

  • Adler J H, Young M, Nes W R. 1977. Determination of the absolute configuration at C-20 and C-24 of ergosterol in ascomycetes and basidiomycetes by proton magnetic resonance spectroscopy. Lipids, 12(4): 364–366.

    Article  Google Scholar 

  • Al-Burtamani S K S, Fatope M O, Marwah R G, Onifade A K, Al-Saidi S H. 2005. Chemical composition, antibacterial and antifungal activities of the essential oil of Haplophyllum tuberculatum from Oman. J. Ethnopharmacol., 96(1–2): 107–112.

    Article  Google Scholar 

  • Amir-Heidari B, Micklefield J. 2007. NMR confirmation that tryptophan dehydrogenation occurs with Syn stereochemistry during the biosynthesis of CDA in Streptomyces coelicolor. J. Org. Chem., 72(23): 8 950–8 953.

    Article  Google Scholar 

  • Andersen R J, Wolfe M S, Faulkner D J. 1974. Autotoxic antibiotic production by a marine Chromobacterium. Marine Biology, 27(4): 281–285.

    Article  Google Scholar 

  • Bergeron R J, Cavanaugh P F Jr, Kline S J, Hughes R G Jr, Elliott G T, Porter C W. 1984. Antineoplastic and antiherpetic activity of spermidine catecholamide iron chelators. Biochem. Biophys. Res. Commun., 121(3): 848–854.

    Article  Google Scholar 

  • Cafieri F, Fattorusso E, Gavagnin M, Santacroce C. 1985. 3,5,6 -Trihydroxysterols from the Mediterranean bryozoan Myriapora truncata. J. Nat. Prod., 48(6): 944–947.

    Article  Google Scholar 

  • Dai M C, Tabacchi R, Saturnin C. 1993. Nitrogen-containing aromatic compound from the culture medium of Penicillium chrysogenum Thom. Chimia, 47(6): 226–229.

    Google Scholar 

  • de la Campa R, Seifert K, Miller J D. 2007. Toxins from strains of Penicillium chrysogenum isolated from buildings and other sources. Mycopathologia, 163(3): 161–168.

    Article  Google Scholar 

  • Du L, Li D H, Zhu T J, Cai S X, Wang F P, Xiao X, Gu Q Q. 2009. New alkaloids and diterpenes from a deep ocean sediment derived fungus Penicillium sp. Tetrahedron, 65(5): 1 033–1 039.

    Article  Google Scholar 

  • Franzén J, Fisher A. 2009. Asymmetric alkaloid synthesis: a one-pot organocatalytic reaction to quinolizidine derivatives. Angew. Chem. Int. Ed. Engl., 48(4): 787–791.

    Article  Google Scholar 

  • Gao S S, Li X M, Zhang Y, Li C S, Cui C M, Wang B G. 2011. Comazaphilones A F, azaphilone derivatives from the marine sediment-derived fungus Penicillium commune QSD-17. J. Nat. Prod., 74(2): 256–261.

    Article  Google Scholar 

  • Haefner B. 2003. Drugs from the deep: marine natural products as drug candidates. Drug Discov. Today, 8(12): 536–544.

    Article  Google Scholar 

  • Hikino H, Nabetani S, Takemoto T. 1973. Structure and biosynthesis of chrysogine, a metabolite of Penicillium Chrysogenum. Yakugaku Zasshi, 93(5): 619–623.

    Google Scholar 

  • Kettering M, Sterner O, Anke T. 2004. Antibiotics in the chemical communication of fungi. Z. Naturforsch. C, 59(11): 816–823.

    Google Scholar 

  • Kozlovsky A G, Zhelifonova V P, Antipova T V, Adanin V M, Novikova N D, Deshevaia E A, Schlegel B, Dahse H M, Gollmick F A, Grafe U. 2004. Penicillium expansum, a resident fungal strain of the orbital complex Mir, producing xanthocillin X and questiomycin A. Prikl. Biokhim. Mikrobiol., 40(3): 344–349.

    Google Scholar 

  • Larsen T O, Smedsgaard J, Lund F, Frisvad J C, Gareis M. 2000. Chemical characterisation of cheese associated fungi. Mycotoxin Research, 16(1): 109–112.

    Article  Google Scholar 

  • Miyaji K, Ishiwata N, Nakamura T, Nishino T, Kamiya H, Yamamoto M. 2005. Thrombopoietin receptor activaor and process for producing the same. United States Patent (US 2005/0282730 A1).

  • Noda N, Kubota S, Miyata Y, Miyahara K. 2000. Optically active N-acetyldopamine dimer of the crude drug “Zentai”, the cast-off shell of the cicada, Cryptotympana sp. Chem. Pharm. Bull., 48(11): 1 749–1 752.

    Article  Google Scholar 

  • Rahaim Jr, Ronald J, Maleczka Jr, Robert E. 2006. Palladiumcatalyzed silane/siloxane reductions in the one-pot conversion of nitro compounds to their amines, hydroxylamines, amides, sulfonamides, and carbamates. Synthesis, 2006(19): 3 316–3 340.

    Google Scholar 

  • Rothe W. 1950. Antibiotic complex produced by Penicillium notatum Westling. Pharmazie, 5: 190.

    Google Scholar 

  • Shen C C, Syu W J, Li S Y, Lin C H, Lee G H, Sun C M. 2002. Antimicrobial activities of naphthazarins from Arnebia euchroma. J. Nat. Prod., 65(12): 1 857–1 862.

    Google Scholar 

  • Smith W B. 1977. The carbon-13 spectra of steroids on the way to ecdysone. Org. Magn. Reson., 9(11): 644–648.

    Article  Google Scholar 

  • TimTec Compound Libraries. 2010. Harmony Business Park Building, Newark, USA.

  • Vesonder R F. 1979. Xanthocillin, a metabolite of Eupenicillium egyptiacum NRRL 1022. J. Nat. Prod., 42(2): 232–233.

    Article  Google Scholar 

  • Wagener R E, Davis N D, Diener U L. 1980. Penitrem A and roquefortine production by Penicillium commune. Appl. Environ. Microbiol., 39(4): 882–887.

    Google Scholar 

  • Wang S, Li X M, Teuscher F, Li D L, Diesel A, Ebel R, Proksch P, Wang B G. 2006. Chaetopyranin, a benzaldehyde derivative, and other related metabolites from Chaetomium globosum, an endophytic fungus derived from the marine red alga Polysiphonia urceolata. J. Nat. Prod., 69(11): 1 622–1 625.

    Article  Google Scholar 

  • Yamaguchi T, Miyake Y, Miyamura A, Ishiwata N, Tatsuta K. 2006. Structure-activity relationships of xanthocillin derivatives as thrombopoietin receptor agonist. J. Antibiot., 59(11): 729–734.

    Article  Google Scholar 

  • Yue J M, Chen S N, Lin Z W, Sun H D. 2001. Sterols from the fungus Lactarium volemus. Phytochemistry, 56(8): 801–806.

    Article  Google Scholar 

  • Zhang Y, Wang S, Li X M, Cui C C, Feng C, Wang B G. 2007. New sphingolipids with a previously unreported 9-methyl-C20-sphingosine moiety from a marine algous endophytic fungus Aspergillus niger EN-13. Lipids, 42(8): 759–764.

    Article  Google Scholar 

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Authors and Affiliations

  1. Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, Qingdao, 266071, China

    Zhuo Shang  (尚卓), Xiaoming Li  (李晓明), Chunshun Li  (李春顺), Shushan Gao  (高书山) & Bingui Wang  (王斌贵)

  2. Graduate University of Chinese Academy of Sciences, Beijing, 100049, China

    Zhuo Shang  (尚卓) & Shushan Gao  (高书山)

  3. Department of Biochemistry and Molecular Biology, Second Military Medical University, Shanghai, 200433, China

    Li Meng  (孟莉) & Caiguo Huang  (黄才国)

Authors
  1. Zhuo Shang  (尚卓)
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  2. Xiaoming Li  (李晓明)
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  3. Li Meng  (孟莉)
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  4. Chunshun Li  (李春顺)
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  5. Shushan Gao  (高书山)
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  6. Caiguo Huang  (黄才国)
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  7. Bingui Wang  (王斌贵)
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Corresponding authors

Correspondence to Caiguo Huang  (黄才国) or Bingui Wang  (王斌贵).

Additional information

Supported by the Ministry of Science and Technology (No. 2010CB833802), the Knowledge Innovation Program of Chinese Academy of Sciences (No. KSCX2-EW-G-12B), and the National Natural Science Foundation of China (No. 30910103914)

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Shang, Z., Li, X., Meng, L. et al. Chemical profile of the secondary metabolites produced by a deep-sea sediment-derived fungus Penicillium commune SD-118. Chin. J. Ocean. Limnol. 30, 305–314 (2012). https://doi.org/10.1007/s00343-012-1075-1

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  • DOI: https://doi.org/10.1007/s00343-012-1075-1

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