Abstract
Two azaphilonidal derivatives [penicilazaphilones B (1) and C (2)], have been isolated from the fermented products of marine fungus strain Penicillium sclerotiorum M-22, penicilazaphilones C was a new compound. The compound’s structures were identified by the analysis of spectroscopic data including 1D and 2D NMR techniques (1H-NMR, 13C-NMR, COSY, HMQC, and HMBC). Biological evaluation revealed that penicilazaphilones B and C showed selective cytotoxicity against melanoma cells B-16 and human gastric cancer cells SGC-7901 with IC50 values of 0.291, 0.449 and 0.065, 0.720 mM, respectively, while exhibiting no significant toxicity to normal mammary epithelial cells M10 at the same concentration. Moreover, penicilazaphilones C also exhibited strong antibacterial activity against Staphylococcus aureus, Pseudomonas aeruginosa, Klebsiella pneumonia and Escherichia coli with MIC values 0.037–0.150 mM, while penicilazaphilones B’s bacteriostatic action was weaker.
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Akihisa T, Tokuda H, Yasukawa K, Ukiya M, Kiyota A, Sakamoto N, Suzuki T, Tanabe N, Nishino H (2005) Azaphilones, furanoisophthalides, and amino acids from the extracts of Monascus pilosus-fermented rice (red-mold rice) and their chemopreventive effects. J Agric Food Chem 53:562–565
An CY, Li XM, Li CS, Xu GM, Wang BG (2014) Prenylated indolediketopiperazine peroxides and related homologues from the marine sediment-derived fungus Penicillium brefeldianum SD-273. Mar Drugs 12:746–756
Andrews JM (2001) Determination of minimum inhibitory concentrations. J Antimicrob Chemother 49:5–16
Arunpanichlert J, Rukachaisirikul V, Sukpondma Y, Phongpaichit S, Tewtrakul S, Rungjindamai N, Sakayaroj J (2010) Azaphilone and isocoumarin derivatives from the endophytic fungus Penicillium sclerotiorum PSU-A13. Chem Pharm Bull 58:1033–1036
Bladt TT, Frisvad JC, Knudsen PB, Larsen TO (2013) Anticancer and antifungal compounds from Aspergillus, Penicillium and other filamentous fungi. Molecules 18:11338–11376
Blunt JW, Copp BR, Keyzers RA, Munro MH, Prinsep MR (2012) Marine natural products. Nat Prod Rep 29:144–222
Blunt JW, Copp BR, Keyzers RA, Munro MH, Prinsep MR (2014) Marine natural products. Nat Prod Rep 31:160–258
Houbraken J, Samson RA (2011) Phylogeny of Penicillium and the segregation of Trichocomaceae into three families. Stud Mycol 70:1–51
Li LQ, Yang YG, Zeng Y, Zou C, Zhao PJ (2010) A new azaphilone, kasanosin C, from an endophytic Talaromyces sp. T1BF. Molecules 15:3993–3997
Li CS, Li XM, Gao SS, Lu YH, Wang BG (2013) Cytotoxic anthranilic acid derivatives from deep sea sediment-derived fungus Penicillium paneum SD-44. Mar Drugs 11:3068–3076
Matsuzaki K, Ikeda H, Masuma R, Haruo T, Satoshi O (1995) Isochromophilones I and II, novel inhibitors against gp-120-CD4 Binding Produced by Penicillium multicolor FO-2338. J Antibiot 48:703–707
Niu Y, Yi N, Yuan L, Wang R (2013) Study on antibacterial effect of medlar and hawithorn compound extract in vitro. Afr J Tradit Complement Altern Med 10:567–573
Quang DN, Harinantenaina L, Nishizawa T, Hashimoto T, Kohchi C, Soma GI, Asakawa Y (2006) Inhibition of nitric oxide production in RAW 264.7 cells by azaphilones from Xylariaceous fungi. Biol Pharm Bull 29:34–37
Rivera KG, Seifert KA (2011) A taxonomic and phylogenetic revision of the Penicillium sclerotiorum complex. Stud Mycol 70:139–158
Somoza AD, Lee KH, Chiang YM, Oakley BR, Wang CC (2012) Reengineering an azaphilone biosynthesis pathway in Aspergillus nidulans to create lipoxygenase inhibitors. Org Lett 14:972–975
Tavakolinia F, Baghipour T, Hossaini Z, Zareyee D, Khalilzadeh MA, Rajabi M (2012) Antiproliferative activity of novel thiopyran analogs on MCF-7 breast and HCT-15 colon cancer cells: synthesis, cytotoxicity, cell cycle analysis, and DNA-binding. Nucleic Acid Ther 22:265–270
Toki S, Tanaka T, Uosaki Y, Yoshida M, Suzuki Y, Kita K, Mihara A, Ando K, Lokkernkkern NA, Matsuda Y (1999) RP-1551s, a family of azaphilones produced by Penicillium sp., inhibit the binding of PDGFto the extracellular domain of its receptor. J Antibiot 52:235–244
Tomoda H, Matsushima C, Tabata N, Namatame I, Tanaka H, Bamberger MJ, Arai HFM, Inoue K, Omura S (1999) Stucture-specific inihibition of: cholesteryl ester transfer proteins by azaphilones. J Antibiot 52:160–170
Visagie CM, Houbraken J, Frisvad JC, Hong SB, Klaassen CH, Perrone G, Seifert KA, Varga J, Yaguchi T, Samson RA (2014) Identification and nomenclature of the genus Penicillium. Stud Mycol 78:343–371
Yamada T, Muroga Y, Tanaka R (2009) New azaphilones, seco-chaetomugilins A and D, produced by a marine-fish-derived Chaetomium globosum. Mar Drugs 7:249–257
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The authors acknowledge the financial support provided by The National Natural Science Foundation of China, Project Nos 81560484.
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Zhou, Sl., Wang, M., Zhao, Hg. et al. Penicilazaphilone C, a new antineoplastic and antibacterial azaphilone from the Marine Fungus Penicillium sclerotiorum . Arch. Pharm. Res. 39, 1621–1627 (2016). https://doi.org/10.1007/s12272-016-0828-3
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DOI: https://doi.org/10.1007/s12272-016-0828-3