Cytotoxic epipolythiodioxopiperazine alkaloids from filamentous fungi of the Bionectriaceae

Journal of Antibiotics

Volumn 65, Issue 11, 2012, Pages 559-564

  Figueroa, Mario ^a   Graf, Tyler N ^a   Ayers, Sloan ^a   Adcock, Audrey F ^b   Kroll, David J ^b   Yang, Jilai ^c   Swanson, Steven M ^c   Munoz Acuna, Ulyana ^d   Carcache De Blanco, Esperanza J ^d   Agrawal, Rajesh ^e   Wani, Mansukh C ^a,f   Darveaux, Blaise A ^g   Pearce, Cedric J ^g   Oberlies, Nicholas H ^a  

^a UNIVERSITY OF NORTH CAROLINA AT GREENSBORO   (United States)

^b NORTH CAROLINA CENTRAL UNIVERSITY   (United States)

^c UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^d OHIO STATE UNIVERSITY   (United States)

^e UNIVERSITY OF COLORADO   (United States)

^f RTI INTERNATIONAL   (United States)

^g Mycosynthetix Inc   (United States)

Author keywords

cytotoxicity; EGFR; epipolythiodioxopiperazine alkaloids; fungus; NF B

Indexed keywords

11' DEOXYVERTICILLIN A; ALKALOID DERIVATIVE; ANTIBIOTIC AGENT; ANTINEOPLASTIC AGENT; EPIDERMAL GROWTH FACTOR RECEPTOR KINASE INHIBITOR; EPIPOLYTHIODIOXOPIPERAZINE ALKALOID; FUNGAL EXTRACT; GLIOCLADICILLIN A; GLIOCLADICILLIN C; ORGANIC COMPOUND; SCH 52900; SCH 52901; UNCLASSIFIED DRUG; VERTICILLIN A; VERTICILLIN H;

ARTICLE; BIONECTRIACEAE; CANCER CELL; CELL FRACTIONATION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYTOTOXICITY; DRUG ACTIVITY; FUNGAL STRAIN; FUNGUS; FUNGUS ISOLATION; HUMAN; HUMAN CELL; IC 50; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; NUCLEOTIDE SEQUENCE; PRIORITY JOURNAL;

ANTIBIOTICS, ANTINEOPLASTIC; ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; DISULFIDES; DRUG SCREENING ASSAYS, ANTITUMOR; HUMANS; HYPOCREALES; INDOLE ALKALOIDS; INDOLES; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; NF-KAPPA B; PIPERAZINES; RECEPTOR, EPIDERMAL GROWTH FACTOR; TERPHENYL COMPOUNDS;

BIONECTRIACEAE; FUNGI;

EID: 84870362028     PISSN: 00218820     EISSN: 18811469     Source Type: Journal    
DOI: 10.1038/ja.2012.69     Document Type: Article

References (40)

1. Chen, Y. et al. Ecology-based screen identifies new metabolites from a Cordycepscolonizing fungus as cancer cell proliferation inhibitors and apoptosis inducers. Cell Prolif. 42, 838-847 (2009).
2. Isham, C. R. et al. Chaetocin: a promising new antimyeloma agent with in vitro and in vivo activity mediated via imposition of oxidative stress. Blood 109, 2579-2588 (2007). (Pubitemid 46425905)
3. Zhang, Y. X. et al. 11,110-Dideoxy-verticillin: a natural compound possessing growth factor receptor tyrosine kinase-inhibitory effect with anti-tumor activity. Anticancer Drugs 16, 515-524 (2005).
4. Takahashi, C. et al. Leptosins I and J, cytotoxic substances produced by a Leptosphaeria sp. Physico-chemical properties and structures. J. Antibiot. 47, 1242-1249 (1994). (Pubitemid 24373399)
5. Takahashi, C. et al. Leptosins, antitumor metabolites of a fungus isolated from a marine alga. J. Chem. Soc., Perkin Trans. 1, 1859-1864 (1994).
6. Takahashi, C. et al. Potent cytotoxic metabolites from a Leptosphaeria species. Structure determination and conformational analysis. Tetrahedron 51, 3483-3498 (1995).
7. Chen, Y. et al. Antiangiogenic activity of 11,110-dideoxyverticillin, a natural product isolated from the fungus Shiraia bambusicola. Biochem. Biophys. Res. Commun. 329, 1334-1342 (2005). (Pubitemid 40568716)
8. Saito, T. et al. Chetracin A and chaetocins B and C, three new epipolythiodioxopiperazines from Chaetomium spp. Chem. Pharm. Bull. 36, 1942-1956 (1998).
9. Son, B. W., Jensen, P. R., Kauffman, C. A. & Fenical, W. New cytotoxic epidithiodioxopiperazines related to verticillin A from a marine isolate of the fungus Penicillium. Nat. Prod. Lett. 13, 213-222 (1999). (Pubitemid 29332878)
10. Feng, Y., Blunt, J. W., Cole, A. L. & Munro, M. H. Novel cytotoxic thiodiketopiperazine derivatives from a Tilachlidium sp. J. Nat. Prod. 67, 2090-2092 (2004). (Pubitemid 40092563)
11. Zheng, C. J., Park, S. H., Koshino, H., Kim, Y. H. & Kim, W. G. Verticillin G, a new antibacterial compound from Bionectra byssicola. J. Antibiot. 60, 61-64 (2007).
12. Zheng, C. J., Kim, C. J., Bae, K. S., Kim, Y. H. & Kim, W. G. Bionectins A-C, epidithiodioxopiperazines with anti-MRSA activity, from Bionectra byssicola F120. J. Nat. Prod. 69, 1816-1819 (2006). (Pubitemid 46144985)
13. Bertinetti, B. V., Rodriguez, M. A., Godeas, A. M. & Cabrera, G. M. 1H,10H- [3,30]biindolyl from the terrestrial fungus Gliocladium catenulatum. J. Antibiot. 63, 681-683 (2010).
14. Argoudelis, A. D. Melinacidins 2, 3 and 4, new '3,6- epidithiadiketopiperazine' antibiotics. J. Antibiot. 25, 171-178 (1972).
15. Joshi, B. K., Gloer, J. B. & Wicklow, D. T. New verticillin and glisoprenin analogues from Gliocladium catenulatum, a mycoparasite of Aspergillus flavus Sclerotia. J. Nat. Prod. 62, 730-733 (1999). (Pubitemid 29259091)
16. Minato, H., Matsumoto, M. & Katayama, T. Verticillin A, a new antibiotic from Verticillium sp. J. Chem. Soc. D 44-45 (1971).
17. Watts, K. R. et al. Assessing the trypanocidal potential of natural and semi-synthetic diketopiperazines from two deep water marine-derived fungi. Bioorg. Med. Chem. 18, 2566-2574 (2010).
18. Dong, J. Y., He, H. P., Shen, Y. M. & Zhang, K. Q. Nematicidal epipolysulfanyldioxopiperazines from Gliocladium roseum. J. Nat. Prod. 68, 1510-1513 (2005).
19. Ovenden, S. P. et al. A diketopiperazine dimer from a marine-derived isolate of Aspergillus niger. J. Nat. Prod. 67, 2093-2095 (2004). (Pubitemid 40092564)
20. Erkel, G., Gehrt, A., Anke, T. & Sterner, O. Induction of differentiation in acute promyelocytic leukemia cells (HL-60) by the verticillin derivative Sch 52900. Z. Naturforsch. C: J. Biosci. 57, 759-767 (2002). (Pubitemid 35008541)
21. Gardiner, D. M., Waring, P. & Howlett, B. J. The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis. Microbiology 151, 1021-1032 (2005). (Pubitemid 40568000)
22. Hauser, D., Weber, H. P. & Sigg, H. P. Isolierung und strukturaufkla?rung von chaetocin. Helv. Chem. Acta. 53, 1061-1073 (1970).
23. Katagiri, K., Sato, K., Hayakawa, S., Matsushima, T. & Minato, H. Verticillin A, a new antibiotic from Verticillium sp. J. Antibiot. 23, 420-422 (1970).
24. Minato, H., Matsumoto, M. & Katayama, T. Studies on the metabolites of Verticillium sp. Structures of verticillins A, B, and C. J. Chem. Soc., Perkin Trans. 1 17, 1819-1825 (1973).
25. Kim, J., Ashenhurst, J. A. & Movassaghi, M. Total synthesis of 11,110- dideoxyverticillin A. Science 324, 238-241 (2009).
26. Miller, S. J. Chemistry. Total chemical synthesis peers into the biosynthetic black box. Science 324, 186-187 (2009).
27. Kim, J. & Movassaghi, M. General approach to epipolythiodiketopiperazine alkaloids: total synthesis of chaetocins A and C and 12,120-dideoxychetracin A. J. Am. Chem. Soc. 132, 14376-14378 (2010).
28. Chu, M. et al. Inhibition of c-fos proto-oncogene induction by Sch 52900 and Sch 52901, novel diketopiperazine produced by Gliocladium sp. J. Antibiot. 48, 1440-1445 (1995). (Pubitemid 26016904)
29. Liu, F. et al. Verticillin a overcomes apoptosis resistance in human colon carcinoma through DNA methylation-dependent upregulation of BNIP3. Cancer Res. 71, 6807-6816 (2011).
30. Orjala, J., Oberlies, N. H., Pearce, C. J., Swanson, S. M. & Kinghorn, A. D. Discovery of potential anticancer agents from aquatic cyanobactiria filamentous fungi and tropical plants. in Bioactive Compounds from Natural Sources. Natural Products as Lead Compounds in Drug Discovery 2nd edn (ed. Tringali, C.) 37-63 (Taylor & Francis, London, UK, 2012).
31. Kinghorn, A. D. et al. Discovery of anticancer agents of diverse natural origin. Pure Appl. Chem. 81, 1051-1063 (2009).
32. Che, Y. et al. Institute of Microbiology, Chinese Academy of Sciences, Peop. Rep. China). Method for preparing gliocladicillin C and application thereof. CN patent no. 2009-10077302-101805699 (17 February 2009).
33. Pahl, H. L. et al. The immunosuppressive fungal metabolite gliotoxin specifically inhibits transcription factor NF-kappaB. J. Exp. Med. 183, 1829-1840 (1996). (Pubitemid 26134323)
34. Soule, H. D., Vazguez, J., Long, A., Albert, S. & Brennan, M. A human cell line from a pleural effusion derived from a breast carcinoma. J. Natl. Cancer Inst. 51, 1409-1416 (1973).
35. Carney, D. N., Gazdar, A. F., Bunn, Jr P. A. & Guccion, J. G. Demonstration of the stem cell nature of clonogenic tumor cells from lung cancer patients. Stem Cells 1, 149-164 (1982). (Pubitemid 12072473)
36. Rosenblum, M. L. et al. Stem cell studies of human malignant brain tumors. Part 1: Development of the stem cell assay and its potential. J. Neurosurg. 58, 170-176 (1983). (Pubitemid 13190248)
37. Fogh, J. & Trempe, G. in Human Tumor Cells In Vitro 115-159 (Plenum Press, New York, USA, 1975).
38. Rae, J. M., Creighton, C. J., Meck, J. M., Haddad, B. R. & Johnson, M. D. MDA-MB- 435 cells are derived from M14 melanoma cells - a loss for breast cancer, but a boon for melanoma research. Breast Cancer Res. Treat. 104, 13-19 (2007). (Pubitemid 46976633)
39. Ayers, S. et al. Resorcylic acid lactones with cytotoxic and NF-kappaB inhibitory activities and their structure-activity relationships. J. Nat. Prod. 74, 1126-1131 (2011).
40. Deep, G., Singh, R. P., Agarwal, C., Kroll, D. J. & Agarwal, R. Silymarin and silibinin cause G1 and G2-M cell cycle arrest via distinct circuitries in human prostate cancer PC3 cells: a comparison of flavanone silibinin with flavanolignan mixture silymarin. Oncogene 25, 1053-1069 (2005). (Pubitemid 43277013)