Seven new and two known lipopeptides as well as five known polyketides: the activated production of silent metabolites in a marine-derived fungus by chemical mutagenesis strategy using diethyl sulphate.
作者： Chang-Jing Wu , Chang-Wei Li , Cheng-Bin Cui
DOI: 10.3390/MD12041815
关键词: Penicillium purpurogenum 、 Diethyl sulfate 、 MTT assay 、 Mutant 、 Mutagenesis (molecular biology technique) 、 Stereochemistry 、 Biochemistry 、 Polyketide 、 Biology 、 Sterigmatocystin 、 Penicillium
摘要: AD-2-1 is an antitumor fungal mutant obtained by diethyl sulfate mutagenesis of a marine-derived Penicillium purpurogenum G59. The G59 strain originally did not produce any metabolites with activities in MTT assays using K562 cells. Tracing newly produced under guidance assay and TLC analysis direct comparison control extract, seven new (1–7) two known (8–9) lipopeptides were isolated together five polyketides 10–14 from the extract AD-2-1. Structures compounds including their absolute configurations determined spectroscopic chemical evidences named as penicimutalides A–G (1–7). Seven identified fellutamide B (8), C (9), 1′-O-methylaverantin (10), averantin (11), averufin (12), nidurufin (13), sterigmatocystin (14). In assay, 1–14 inhibited several human cancer cell lines to varying extents. All bioassays HPLC-photodiode array detector (PDAD)-UV HPLC-electron spray ionization (ESI)-MS analyses demonstrated that production was caused activated silent original strain. Present results provided additional examples for effectiveness strategy sulphate discover activating isolates.
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Robert H. Cichewicz, Jon C. Henrikson, Xiaoru Wang, Katie M. Branscum, Strategies for Accessing Microbial Secondary Metabolites from Silent Biosynthetic Pathways American Society of Microbiology. pp. 78- 95 ,(2010) , 10.1128/9781555816827.CH7
Kozo Ochi, Takeshi Hosaka, New strategies for drug discovery: activation of silent or weakly expressed microbial gene clusters Applied Microbiology and Biotechnology. ,vol. 97, pp. 87- 98 ,(2013) , 10.1007/S00253-012-4551-9
Shi-Ming Fang, Chang-Jing Wu, Chang-Wei Li, Cheng-Bin Cui, A Practical Strategy to Discover New Antitumor Compounds by Activating Silent Metabolite Production in Fungi by Diethyl Sulphate Mutagenesis Marine Drugs. ,vol. 12, pp. 1788- 1814 ,(2014) , 10.3390/MD12041788
Hideyuki Shigemori, Shinobu Wakuri, Kazunaga Yazawa, Takemichi Nakamura, Takuma Sasaki, Jun'ichi Kobayashi, Fellutamides A and B, cytotoxic peptides from a marine fish-possessing fungus Penicillium fellutanum Tetrahedron. ,vol. 47, pp. 8529- 8534 ,(1991) , 10.1016/S0040-4020(01)82396-6
Annalisa Guaragna, Mauro De Nisco, Silvana Pedatella, Giovanni Palumbo, Studies towards lipid A: A synthetic strategy for the enantioselective preparation of 3-hydroxy fatty acids Tetrahedron-asymmetry. ,vol. 17, pp. 2839- 2841 ,(2006) , 10.1016/J.TETASY.2006.10.023
John S. Schneekloth, John L. Sanders, John Hines, Craig M. Crews, Neurotrophic peptide aldehydes: solid phase synthesis of fellutamide B and a simplified analog. Bioorganic & Medicinal Chemistry Letters. ,vol. 16, pp. 3855- 3858 ,(2006) , 10.1016/J.BMCL.2006.04.029
Gang Lin, Dongyang Li, Tamutenda Chidawanyika, Carl Nathan, Huilin Li, Fellutamide B is a potent inhibitor of the Mycobacterium tuberculosis proteasome Archives of Biochemistry and Biophysics. ,vol. 501, pp. 214- 220 ,(2010) , 10.1016/J.ABB.2010.06.009
Helge Björn Bode, Barbara Bethe, Regina Höfs, Axel Zeeck, Big Effects from Small Changes: Possible Ways to Explore Nature's Chemical Diversity ChemBioChem. ,vol. 3, pp. 619- 627 ,(2002) , 10.1002/1439-7633(20020703)3:7<619::AID-CBIC619>3.0.CO;2-9
Raymond A. Murphy, Michael P. Cava, Stereochemistry of nidurufin: synthesis of 6,8-dideoxynidurufin and 6,8-dideoxyepinidurufin Journal of the American Chemical Society. ,vol. 106, pp. 7630- 7632 ,(1984) , 10.1021/JA00336A058
Changlun Shao, Changyun Wang, Meiyan Wei, Shangde Li, Zhigang She, Yucheng Gu, Yongcheng Lin, Structural and spectral assignments of six anthraquinone derivatives from the mangrove fungus (ZSUH‐36) Magnetic Resonance in Chemistry. ,vol. 46, pp. 886- 889 ,(2008) , 10.1002/MRC.2266