Activation of dormant secondary metabolite production by introducing neomycin resistance into the deep-sea fungus, Aspergillus versicolor ZBY-3

Marine Drugs

Volumn 12, Issue 8, 2014, Pages 4326-4352

  Dong, Yuan ^a   Cui, Cheng Bin ^a   Li, Chang Wei ^a   Hua, Wei ^a   Wu, Chang Jing ^a   Zhu, Tian Jiao ^b   Gu, Qian Qun ^b  

^a BEIJING INSTITUTE OF PHARMACOLOGY AND TOXICOLOGY   (China)

^b OCEAN UNIVERSITY OF CHINA   (China)

Author keywords

Antitumor activity; Aspergillus versicolor ZBY 3; Deep sea fungus; Neomycin resistance; Secondary metabolite production; Ultrasound

Indexed keywords

3BETA,5ALPHA,9ALPHA TRIHYDROXY ERGOSTA 7,22 DIEN 6 ONE; ANTINEOPLASTIC AGENT; ASPERGILLUS VERSICOLOR EXTRACT; CYCLO(DEXTRO PROLINE DEXTRO PHENYLALANINE); CYCLO(DEXTRO TYROSINE DEXTRO PROLINE); CYCLO(ISOLEUCINE PROLINE); CYCLO(LEUCINE PROLINE); FUNGAL EXTRACT; NEOMYCIN; PHENETHYL 5 OXO LEVO PROLINATE; UNCLASSIFIED DRUG; AMINOGLYCOSIDE;

ANTIBIOTIC RESISTANCE; ANTINEOPLASTIC ACTIVITY; ARTICLE; ASPERGILLUS VERSICOLOR; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG EFFECT; DRUG IDENTIFICATION; DRUG ISOLATION; FUNGAL METABOLISM; FUNGAL STRAIN; FUNGUS ISOLATION; FUNGUS MUTANT; HUMAN; HUMAN CELL; METABOLIC REGULATION; MYELOID LEUKEMIA CELL LINE; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRASOUND; ASPERGILLUS; FUNGUS; GENETICS; HELA CELL LINE; HL 60 CELL LINE; K562 CELL LINE; METABOLISM; MICROBIAL SENSITIVITY TEST; MUTATION; PROCEDURES; TUMOR CELL LINE;

AMINOGLYCOSIDES; ANTINEOPLASTIC AGENTS; ASPERGILLUS; CELL LINE, TUMOR; DRUG RESISTANCE, MICROBIAL; FUNGI; HELA CELLS; HL-60 CELLS; HUMANS; K562 CELLS; METABOLIC NETWORKS AND PATHWAYS; MICROBIAL SENSITIVITY TESTS; MUTATION; NEOMYCIN;

EID: 84908077901     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md12084326     Document Type: Article

References (69)

1. Bugni, T.S.; Ireland, C.M. Marine-derived fungi: A chemically and biologically diverse group of microorganisms. Nat. Prod. Rep. 2004, 21, 143-163.
2. Saleem, M.; Ali, M.S.; Hussain, S.; Jabbar, A.; Ashraf, M.; Lee, Y.S. Marine natural products of fungal origin. Nat. Prod. Rep. 2007, 24, 1142-1152.
3. Bhatnagar, I.; Kim, S.-K. Immense essence of excellence: Marine microbial bioactive compounds. Mar. Drugs 2010, 8, 2673-2701.
4. Rateb, M.E.; Ebel, R. Secondary metabolites of fungi from marine habitats. Nat. Prod. Rep. 2011, 28, 290-344.
5. Pejin, B.; Jovanović, K.K.; Mojović, M.; Savić, A.G. New and highly potent antitumor natural products from marine-derived fungi: Covering the period from 2003 to 2012. Curr. Top. Med. Chem. 2013, 13, 2745-2766.
6. Newman, D.J.; Cragg, G.M. Marine-sourced anti-cancer and cancer pain control agents in clinical and late preclinical development. Mar. Drugs 2014, 12, 255-278.
7. Blunt, J.W.; Copp, B.R.; Keyzers, R.A.; Munro, M.H.G.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2014, 31, 160-258.
8. Blunt, J.W.; Copp, B.R.; Keyzers, R.A.; Munro, M.H.G.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2013, 30, 237-323.
9. Blunt, J.W.; Copp, B.R.; Keyzers, R.A.; Munro, M.H.G.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2012, 29, 144-222.
10. Blunt, J.W.; Copp, B.R.; Munro, M.H.G.; Northcote, P.T.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2011, 28, 196-268.
11. Blunt, J.W.; Copp, B.R.; Munro, M.H.G.; Northcote, P.T.; Prinsep, M.R. Marine natural products. Nat. Prod. Rep. 2010, 27, 165-237.
12. Schneider, P.; Misiek, M.; Hoffmeister, D. In vivo and in vitro production options for fungal secondary metabolites. Mol. Pharm. 2008, 5, 234-242.
13. Hertweck, C. Hidden biosynthetic treasures brought to light. Nat. Chem. Biol. 2009, 5, 450-452.
14. Cichewicz, R.H.; Henrikson, J.C.; Wang, X.; Branscum, K.M. Strategies for accessing microbial secondary metabolites from silent biosynthetic pathways. In Manual of Industrial Microbiology and Biotechnology, 3rd ed.; Baltz, R.H., Davies, J.E., Demain, A.L., Bull, A.T., Junker, B., Katz, L., Lynd, L.R., Masurekar, P.C., Reeves, D., Zhao, H., Eds.; ASM Press: Washington, DC, USA, 2010; pp. 78-95.
15. Brakhage, A.A.; Schroeckh, V. Fungal secondary metabolites-Strategies to activate silent gene clusters. Fungal Genet. Biol. 2011, 48, 15-22.
16. Ochi, K.; Hosaka, T. New strategies for drug discovery: Activation of silent or weakly expressed microbial gene clusters. Appl. Microbiol. Biotechnol. 2013, 97, 87-98.
17. Bode, H.B.; Bethe, B.; Höfs, R.; Zeeck, A. Big effects from small changes: Possible ways to explore nature's chemical diversity. ChemBioChem 2002, 3, 619-627.
18. Marmann, A.; Aly, A.H.; Lin, W.; Wang, B.; Proksch, P. Co-cultivation-A powerful emerging tool for enhancing the chemical diversity of microorganisms. Mar. Drugs 2014, 12, 1043-1065.
19. Henrikson, J.C.; Hoover, A.R.; Joyner, P.M.; Cichewicz, R.H. A chemical epigenetics approach for engineering the in situ biosynthesis of a cryptic natural product from Aspergillus niger. Org. Biomol. Chem. 2009, 7, 435-438.
20. Cichewicz, R.H. Epigenome manipulation as a pathway to new natural product scaffolds and their congeners. Nat. Prod. Rep. 2010, 27, 11-22.
21. Takahashi, J.A.; Teles, A.P.C.; Bracarense, A.A.P.; Gomes, D.C. Classical and epigenetic approaches to metabolite diversification in filamentous fungi. Phytochem. Rev. 2013, doi:10.1007/s11101-013-9305-5.
22. Ochi, K.; Okamoto, S.; Tozawa, Y.; Inaoka, T.; Hosaka, T.; Xu, J.; Kurosawa, K. Ribosome engineering and secondary metabolite production. Adv. Appl. Microbiol. 2004, 56, 155-184.
23. Ochi, K. From microbial differentiation to ribosome engineering. Biosci. Biothenol. Biochem. 2007, 71, 1373-1386.
24. Hosaka, T.; Ohnishi-Kameyama, M.; Muramatsu, H.; Murakami, K.; Tsurumi, Y.; Kodani, S.; Yoshida, M.; Fujie, A.; Ochi, K. Antibacterial discovery in actinomycetes strains with mutations in RNA polymerase or ribosomal protein S12. Nat. Biotechnol. 2009, 27, 462-464.
25. Bergmann, S.; Schümann, J.; Scherlach, K.; Lange, C.; Brakhage, A.A.; Hertweck, C. Genomics-driven discovery of PKS-NRPS hybrid metabolites from Aspergillus nidulans. Nat. Chem. Biol. 2007, 3, 213-217.
26. Scherlach, K.; Nützmann, H.-W.; Schroeckh, V.; Dahse, H.-M.; Brakhage, A.A.; Hertweck, C. Cytotoxic pheofungins from an engineered fungus impaired in posttranslational protein modification. Angew. Chem. Int. Ed. 2011, 50, 9843-9847.
27. Chai, Y.-J.; Cui, C.-B.; Li, C.-W.; Wu, C.-J.; Tian, C.-K.; Hua, W. Activation of the dormant secondary metabolite production by introducing gentamicin-resistance in a marine-derived Penicillium purpurogenum G59. Mar. Drugs 2012, 10, 559-582.
28. Fang, S.-M.; Wu, C.-J.; Li, C.-W.; Cui, C.-B. A practical strategy to discover new antitumor compounds by activating silent metabolite production in fungi by diethyl sulphate mutagenesis. Mar. Drugs 2014, 12, 1788-1814.
29. Xia, M.-W.; Cui, C.-B.; Li, C.-W.; Wu, C.-J. Three new and eleven known unusual C25 steroids: Activated production of silent metabolites in a marine-derived fungus by chemical mutagenesis strategy using diethyl sulphate. Mar. Drugs 2014, 12, 1545-1568.
30. Wu, C.-J.; Li, C.-W.; Cui, C.-B. 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. Mar. Drugs 2014, 12, 1815-1838.
31. Dias, T.; Sairam, S.; Kumarasiri, S. Ultrasound diagnosis of fetal renal abnormalities. Best Pract. Res. Clin. Obstet. Gynaecol. 2014, 28, 403-415.
32. Cournane, S.; Fagan, A.J.; Browne, J.E. An audit of a hospital-based Doppler ultrasound quality control protocol using a commercial string Doppler phantom. Phys. Medica 2014, 30, 380-384.
33. Wolfram, F.; Reichenbach, J.R.; Lesser, T.G. An ex vivo human lung model for ultrasound-guided high-intensity focused ultrasound therapy using lung flooding. Ultrasound Med. Biol. 2014, 40, 496-503.
34. Adhikari, S.; Blaivas, M. History, progress, and future of emergency ultrasound. Ultrasound Clin. 2014, 9, 119-121.
35. Krasulya, O.; Shestakov, S.; Bogush, V.; Potoroko, I.; Cherepanov, P.; Krasulya, B. Applications of sonochemistry in russian food processing industry. Ultrason. Sonochem. 2014, doi:10.1016/j.ultsonch.2014.03.015.
36. Chemat, F.; Zill-e-Huma; Khan, M.K. Applications of ultrasound in food technology: Processing, preservation. Ultrason. Sonochem. 2011, 18, 813-835.
37. Awad, T.S.; Moharram, H.A.; Shaltout, O.E.; Asker, D.; Youssef, M.M. Applications of ultrasound in analysis, processing and quality control of food: A review. Food Res. Int. 2012, 48, 410-427.
38. Chisti, Y. Sonobioreactors: Using ultrasound for enhanced microbial productivity. Trends Biotechnol. 2003, 21, 89-93.
39. Yao, L.-Y.; Zhu, Y.-X.; Jiao, R.-H.; Lu, Y.-H.; Tan, R.-X. Enhanced production of fumigaclavine C by ultrasound stimulation in a two-stage culture of Aspergillus fumigatus CY018. Biores. Technol. 2014, 159, 112-117.
40. Bonrath, W. Industrial applications of sonochemistry in the syntheses of vitamin-building blocks. Ultrason. Sonochem. 2003, 10, 55-59.
41. Zhao, Y.; Feng, R.; Shi, Y.; Hu M. Sonochemistry in China between 1997 and 2002. Ultrason. Sonochem. 2005, 12, 173-181.
42. King, R.L.; Brown, J.R.; Pauly, K.B. Localization of ultrasound-induced in vivo neurostimulation in the mouse model. Ultrasound Med. Biol. 2014, 40, 1512-1522.
43. Huang, P.; You, X.; Pan, M.; Li, S.; Zhang, Y.; Zhao, Y.; Wang, M.; Hong, Y.; Pu, Z.; Chen, L.; et al. A novel therapeutic strategy using ultrasound mediated microbubbles destruction to treat colon cancer in a mouse model. Cancer Lett. 2013, 335, 183-190.
44. Sorace, A.G.; Korb, M.; Warram, J.M.; Umphrey, H.; Zinn, K.R. Ultrasound-stimulated drugdelivery fortreatmentof residual disease after incomplete resection of head and neck cancer. Ultrasound Med. Biol. 2014, 40, 755-764.
45. Joersbo, M.; Brunstedt, J. Sonication: A new method for gene transfer to plants. Physiol. Plant. 1992, 85, 230-234.
46. Liang, H.-D.; Lu, Q.L.; Xue, S.-A.; Halliwell, M.; Kodama, T.; Cosgrove, D.O.; Stauss, H.J.; Partridge, T.A.; Blomley, M.J.K. Optimisation of ultrasound-mediated gene transfer (sonoporation) in skeletal muscle cells. Ultrasound Med. Biol. 2004, 30, 1523-1529.
47. Kodama, T.; Tomita, Y.; Koshiyama, K.-I.; Blomley, M.J.K. Transfection effect of microbubbles on cells in superposed ultrasound waves and behavior of cavitation bubble. Ultrasound Med. Biol. 2006, 32, 905-914.
48. Ninomiya, K.; Yamada, R.; Meisaku, H.; Shimizu, N. Effect of ultrasound irradiation on bacterial internalization and bacteria-mediated gene transfer to cancer cells. Ultrason. Sonochem. 2014, 21, 1187-1193.
49. Sun, R.R.; Noble, M.L.; Sun, S.S.; Song, S.; Miao, C.H. Development of therapeutic microbubbles for enhancing ultrasound-mediated gene delivery. J. Control. Release 2014, 182, 111-120.
50. Fdhila, F.; Vázquez, V.; Sánchez, J.; Riguera R. DD-Diketopiperazines: Antibiotics active against Vibrio anguillarum isolated from marine bacteria associated with cultures of Pecten maximus. J. Nat. Prod. 2003, 66, 1299-1301.
51. Wang, G.; Dai, S.; Chen, M.; Wu, H.; Xie, L.; Luo, X.; Li, X. Two diketopiperazine cyclo(Pro-Phe) isomers from marine bacteria Bacillus subtilis sp. 13-2. Chem. Nat. Compd. 2010, 46, 583-585.
52. Thajudeen, H.; Park, K.; Moon, S.-S.; Hong, I.S. An efficient green synthesis of proline-based cyclic dipeptides under water-mediated catalyst-free conditions. Tetrahedron Lett. 2010, 51, 1303-1305.
53. Pedras, M.S.C.; Yu, Y.; Liu, J.; Tandron-Moya, Y.A. Metabolites produced by the phytopathogenic fungus Rhizoctonia solani: Isolation, chemical structure determination, syntheses and bioactivity. Z. Naturforsch. 2005, 60c, 717-722.
54. Selvakumar, S.; Sivasankarana, D.; Singh, V.K. Enantioselective Henry reaction catalyzed by C2-symmetric chiral diamine-copper(II) complex. Org. Biomol. Chem. 2009, 7, 3156-3162.
55. Bhushan, R.; Brückner, H. Marfey's reagent for chiral amino acid analysis: A review. Amino Acids 2004, 27, 231-247.
56. Chen, X.-W.; Li, C.-W.; Hua, W.; Wu, C.-J.; Cui, C.-B.; Zhu, T.-J.; Gu, Q.-Q. Metabolites of Aspergillus sp. 16-02-1 isolated from a deep sea sediment and preliminary test of their antitumor and antifungal activities. Chin. J. Mar. Drugs 2013, 32, 1-10.
57. Xiong, H.Y.; Fei, D.Q.; Zhou, J.S.; Yang, C.J.; Ma, G.L. Steroids and other constituents from the mushroom Armillaria lueo-virens. Chem. Nat. Compd. 2009, 45, 759-761.
58. Hardegger, E.; Ott, H. Kodguration des cocains und derivate der ecgoninsaure. Helv. Chim. Acta 1995, 38, 312-320.
59. Furukawa, A.; Yoshimoto, T.; Tsuru, O.; Ajisawa, Y.; Kinoshita, Y. Pyroglutamic acid derivative. Jpn. Kokai Tokkyo Koho JP 03056462 A, 12 March 1991.
60. Eberhardt, H. 5-Oxo-2-pyrrolidinecarboxylic acid phenylalkanol esters. Ger. Offen. DE 2456634 A1, 12 August 1976.
61. Hoffmann, M.; Molenda, M. Composition for hair comprising PCA and PCA ester. Eur. Pat. Appl. EP 2090291 A1, 19 August 2009.
62. Lee, H.B.; Kim, Y.; Kim, J.C.; Choi, G.J.; Park, S.-H.; Kim, C.-J.; Jung, H.S. Activity of some aminoglycoside antibiotics against true fungi, Phytophthora and Pythium species. J. Appl. Microbiol. 2005, 99, 836-843.
63. Cronan, J.M.; Davidson, T.R.; Singleton, F.L.; Colwell, R.R.; Cardellina, J.H., II. Plant growth promoters isolated from a marine bacterium associated with Palythoa sp. Nat. Prod. Lett. 1998, 11, 271-278.
64. Shigemori, H.; Tenma, M.; Shimazaki, K.; Kobayashi, J. Three new metabolites from the marine yeast Aureobasidium pullulans. J. Nat. Prod. 1998, 61, 696-698.
65. Huang, R.-M.; Ma, W.; Dong, J.-D.; Zhou, X.-F.; Xu, T.; Lee, K.J.; Yang, X.; Xu, S.-H.; Liu, Y. A new 1,4-diazepine from South China Sea marine sponge Callyspongia species. Molecules 2010, 15, 871-877.
66. Park, K.S.; Park, J.W.; Lee, S.Y.; Moon, S.S.; Hong, I.S. Agricultural Agent Containing 2,5-Diketopiperazine Derivative as Active Ingredient. U.S. Patent Application Publication US 20130190177 A1, 25 July 2013.
67. Liu, Y.-X.; Ma, S.-G.; Wang, X.-J.; Zhao, N.; Qu, J.; Yu, S.-S.; Dai, J.-G.; Wang, Y.-H.; Si, Y.-K. Diketopiperazine alkaloids produced by the endophytic fungus Aspergillus fumigatus from the stem of Erythrophloeum fordii Oliv. Helv. Chim. Acta 2012, 95, 1401-1408.
68. Valisolalao, J.; Luu, B.; Ourisson, G. Steroides cytotoxiques de Polyporus versicolor. Tetrahedron 1983, 39, 2779-2785.
69. Kawagishi, H.; Katsumi, R.; Sazawa, T.; Mizuno, T.; Hagiwara, T.; Nakamura, T. Cytotoxic steroids from the mushroom Agaricus blazei. Phytochemistry 1988, 27, 2777-2779.