Peptaibols from two unidentified fungi of the order Hypocreales with cytotoxic, antibiotic, and anthelmintic activities

Journal of Peptide Science

Volumn 18, Issue 8, 2012, Pages 500-510

  Ayers, Sloan ^a   Ehrmann, Brandie M ^a   Adcock, Audrey F ^b   Kroll, David J ^b   Carcache de Blanco, Esperanza J ^c   Shen, Qi ^d   Swanson, Steven M ^d   Falkinham, Joseph O ^e   Wani, Mansukh C ^f   Mitchell, Sheila M ^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 OHIO STATE UNIVERSITY   (United States)

^d UNIVERSITY OF ILLINOIS AT CHICAGO   (United States)

^e VIRGINIA POLYTECHNIC INSTITUTE AND STATE UNIVERSITY   (United States)

^f RTI INTERNATIONAL   (United States)

^g Mycosynthetix Inc   (United States)

Author keywords

Anthelmintic; Cytotoxicity; Higher energy collisional dissociation (HCD); Hypocreales; Peptaibols

Indexed keywords

ALAMETHICIN II; ANTHELMINTIC AGENT; ANTIBIOTIC AGENT; ANTIFUNGAL AGENT; ATROVIRIDIN B; ATROVIRIDIN D; ATROVIRIDIN E; ATROVIRIDIN F; ATROVIRIDIN G; ATROVIRIDIN H; ATROVIRIDIN I; ATROVIRIDIN J; CAMPTOTHECIN; CYTOTOXIC AGENT; HARZIANUM A; HARZIANUM B; IVERMECTIN; LONGIBRANCHIN BIII; PEPTAIBOL; POLYSPORIN B; TRICHOBRACHIN D I; TRICHOKONIN VI; TRICHOKONIN VII; UNCLASSIFIED DRUG; VANCOMYCIN; VINBLASTINE;

AMINO ACID ANALYSIS; ANTHELMINTIC ACTIVITY; ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; CANDIDA ALBICANS; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; ESCHERICHIA COLI; HUMAN; HUMAN CELL; HYPOCREALES; LUNG NON SMALL CELL CANCER; MASS SPECTROMETRY; MYCOBACTERIUM SMEGMATIS; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA; STAPHYLOCOCCUS AUREUS; ULTRA PERFORMANCE LIQUID CHROMATOGRAPHY;

ANIMALS; ANTHELMINTICS; ANTI-BACTERIAL AGENTS; CELL LINE, TUMOR; CELL SURVIVAL; HAEMONCHUS; HUMANS; HYPOCREALES; MEMBRANE POTENTIAL, MITOCHONDRIAL; METHICILLIN-RESISTANT STAPHYLOCOCCUS AUREUS; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; PEPTAIBOLS;

ASCOMYCOTA; FUNGI; HYPOCREALES;

EID: 84864014303     PISSN: 10752617     EISSN: 10991387     Source Type: Journal    
DOI: 10.1002/psc.2425     Document Type: Article

References (49)

1. Toniolo C, Bruckner H. Peptaibiotics: Fungal Peptides Containing α-Dialkyl α-Amino Acids. Vrlag Helvetica Chimica Acta: Zurich, 2009; 702.
2. Toniolo C, Bruckner H. Peptaibiotics. Chem. Biodivers. 2007; 4: 1021-1022.
3. Bruckner H. Peptaibols/peptaibiotics - Editorial. J. Pept. Sci. 2003; 9: 659.
4. Daniel JF, Filho ER. Peptaibols of Trichoderma. Nat. Prod. Rep. 2007; 24: 1128-1141.
5. Leitgeb B, Szekeres A, Manczinger L, Vagvolgyi C, Kredics L. The history of alamethicin: a review of the most extensively studied peptaibol. Chem. Biodivers. 2007; 4: 1027-1051.
6. Kinghorn AD, Carache de Blanco EJ, Chai HB, Orjala J, Farnsworth NR, Soejarto DD, Oberlies NH, Wani MC, Kroll DJ, Pearce CJ, Swanson SM, Kramer RA, Rose WC, Fairchild CR, Vite GD, Emanuel S, Jarjoura D, Cope FO. Discovery of anticancer agents of diverse natural origin. Pure Appl. Chem. 2009; 81: 1051-1063.
7. Orjala J, Oberlies NH, Pearce CJ, Swanson SM, Kinghorn AD. Discovery of potential anticancer agents from aquatic cyanobacteria, filamentous fungi, and tropical plants. In Bioactive Compounds from Natural Sources. Natural Products as Lead Compounds in Drug Discovery. Tringali C (ed.). Taylor & Francis: London, UK, 2012; 37-63.
8. Ayers S, Graf TN, Adcock AF, Kroll DJ, Matthew S, Carache de Blanco EJ, Shen Q, Swanson SM, Wani MC, Pearce CJ, Oberlies NH. Resorcylic acid lactones with cytotoxic and NF-κB inhibitory activities and their structure-activity relationships. J. Nat. Prod. 2011; 74: 1126-1131.
9. Ayers S, Graf TN, Adcock AF, Kroll DJ, Shen Q, Swanson SM, Wani MC, Darveaux BA, Pearce CJ, Oberlies NH, Obionin B. An o-pyranonaphthoquinone decaketide from an unidentified fungus (MSX 63619) from the Order Pleosporales. Tetrahedron Lett. 2011; 52: 5128-5230.
10. Sy-Cordero AA, Graf TN, Adcock AF, Kroll DJ, Shen Q, Swanson SM, Wani MC, Pearce CJ, Oberlies NH. Cyclodepsipeptides, sesquiterpenoids, and other cytotoxic metabolites from the filamentous fungus Trichothecium sp. (MSX 51320). J. Nat. Prod. 2011; 74: 2137-2142.
11. Ayers S, Ehrmann BM, Adcock AF, Kroll DJ, Wani MC, Pearce CJ, Oberlies NH. Thielavin B methyl ester: a cytotoxic benzoate trimer from an unidentified fungus (MSX 55526) from the Order Sordariales. Tetrahedron Lett. 2011; 52: 5733-5735.
12. Summers MY, Kong F, Feng X, Siegel MM, Janso JE, Graziani EI, Carter GT. Septocylindrins A and B: peptaibols produced by the terrestrial fungus Septocylindrium sp. LL-Z1518. J. Nat. Prod. 2007; 70: 391-396.
13. Mitova MI, Murphy AC, Lang G, Blunt JW, Cole AL, Ellis G, Munro MH. Evolving trends in the dereplication of natural product extracts. 2. The isolation of chrysaibol, an antibiotic peptaibol from a New Zealand sample of the mycoparasitic fungus Sepedonium chrysospermum. J. Nat. Prod. 2008; 71: 1600-1603.
14. el Hajji M, Rebuffat S, Lecommandeur D, Bodo B. Isolation and sequence determination of trichorzianines A antifungal peptides from Trichoderma harzianum. Int. J. Pept. Protein Res. 1987; 29: 207-215.
15. Kjer J, Debbab A, Aly AH, Proksch P. Methods for isolation of marine-derived endophytic fungi and their bioactive secondary products. Nat. Protoc. 2010; 5: 479-490.
16. Soule HD, 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. 1973; 51: 1409-1416.
17. Carney DN, Gazdar AF, Bunn PA, Jr., Guccion JG. Demonstration of the stem cell nature of clonogenic tumor cells from lung cancer patients. Stem Cells 1982; 1: 149-164.
18. Rosenblum ML, Gerosa MA, Wilson CB, Barger GR, Pertuiset BF, de Tribolet N, Dougherty DV. Stem cell studies of human malignant brain tumors. Part 1: development of the stem cell assay and its potential. J. Neurosurg. 1983; 58: 170-176.
19. Alali FQ, El-Elimat T, Li C, Qandil A, Alkofahi A, Tawaha K, Burgess JP, Nakanishi Y, Kroll DJ, Navarro HA, Falkinham JO, III, Wani MC, Oberlies NH. New colchicinoids from a native Jordanian meadow saffron, Colchicum brachyphyllum: isolation of the first naturally occurring dextrorotary colchicinoid. J. Nat. Prod. 2005; 68: 173-178.
20. Li C, Lee D, Graf TN, Phifer SS, Nakanishi Y, Riswan S, Setyowati FM, Saribi AM, Soejarto DD, Farnsworth NR, Falkinham JO, III, Kroll DJ, Kinghorn AD, Wani MC, Oberlies NH. Bioactive constituents of the stem bark of Mitrephora glabra. J. Nat. Prod. 2009; 72: 1949-1953.
21. Rae JM, Creighton CJ, Meck JM, Haddad BR, Johnson MD. 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. 2007; 104: 13-19.
22. Nichols WW, Murphy DG, Cristofalo VJ, Toji LH, Greene AE, Dwight SA. Characterization of a new human diploid cell strain, IMR-90. Science 1977; 196: 60-63.
23. Williams AA, Sugandhi EW, Macri RV, Falkinham JO, 3rd, Gandour RD. Antimicrobial activity of long-chain, water-soluble, dendritic tricarboxylato amphiphiles. J. Antimicrob. Chemother. 2007; 59: 451-458.
24. Maisuria BB, Actis ML, Hardrict SN, Falkinham JO, 3rd, Cole MF, Cihlar RL, Peters SM, Macri RV, Sugandhi EW, Williams AA, Poppe MA, Esker AR, Gandour RD. Comparing micellar, hemolytic, and antibacterial properties of di- and tricarboxyl dendritic amphiphiles. Bioorg. Med. Chem. 2011; 19: 2918-2926.
25. Lopez-Aroche U, Salinas-Sanchez DO, de Gives PM, Lopez-Arellano ME, Liebano-Hernandez E, Valladares-Cisneros G, Arias-Ataide DM, Hernandez-Velazquez V. In vitro nematicidal effects of medicinal plants from the Sierra de Huautla, Biosphere Reserve, Morelos, Mexico against Haemonchus contortus infective larvae. J. Helminthol. 2008; 82: 25-31.
26. Corley DG, Millerwideman M, Durley RC. Isolation and structure of harziazum A: a new trichothecene from Trichoderma harzianum. J. Nat. Prod. 1994; 57: 422-425.
27. Jin HZ, Lee JH, Zhang WD, Lee HB, Hong YS, Kim YH, Lee JJ. Harzianums A and B produced by a fungal strain, Hypocrea sp F000527, and their cytotoxicity against tumor cell lines. J. Asian Nat. Prod. Res. 2007; 9: 203-207.
28. Meyer CE, Reusser F. A polypeptide antibacterial agent isolated from Trichoderma viride. Experientia 1967; 23: 85-86.
29. Oh SU, Lee SJ, Kim JH, Yoo ID. Structural elucidation of new antibiotic peptides, atroviridins A, B and C from Trichoderma atroviride. Tetrahedron Lett. 2000; 41: 61-64.
30. New AP, Eckers C, Haskins NJ, Neville WA, Elson S, HuesoRodriguez JA, RiveraSagredo A. Structures of polysporins A-D, four new peptaibols isolated from Trichoderma polysporum. Tetrahedron Lett. 1996; 37: 3039-3042.
31. Pandey RC, Cook JC, Rinehart KL. Peptaibophol antibiotics.3. High-resolution and field desorption mass-spectrometry studies and revised structures of alamethicin-I and alamethicin-II. J. Am. Chem. Soc. 1977; 99: 8469-8483.
32. Huang Q, Tezuka Y, Kikuchi T, Nishi A, Tubaki K, Tanaka K. Studies on metabolites of mycoparasitic fungi .2. Metabolites of Trichoderma koningii. Chem. Pharm. Bull. 1995; 43: 223-229.
33. Leclerc G, Rebuffat S, Bodo B. Directed biosynthesis of peptaibol antibiotics in two Trichoderma strains II. Structure elucidation. J. Antibiot. 1998; 51: 178-183.
34. Leclerc G, Rebuffat S, Goulard C, Bodo B. Directed biosynthesis of peptaibol antibiotics in two Trichoderma strains I. Fermentation and isolation. J. Antibiot. 1998; 51: 170-177.
35. Duclohier H. Peptaibiotics and peptaibols: an alternative to classical antibiotics? Chem. Biodivers. 2007; 4: 1023-1026.
36. Thirumalachar MJ. Antiamoebin, a new antiprotozoal-anthelmintic antibiotic. I. Production and biological studies. Hindustan Antibiot. Bull. 1968; 10: 287-289.
37. Schiell M, Hofmann J, Kurz M, Schmidt FR, Vertesy L, Vogel M, Wink J, Seibert G. Cephaibols, new peptaibol antibiotics with anthelmintic properties from Acremonium tubakii DSM 12774. J. Antibiot. 2001; 54: 220-233.
38. Olsen JV, Macek B, Lange O, Makarov A, Horning S, Mann M. Higher-energy C-trap dissociation for peptide modification analysis. Nat. Methods 2007; 4: 709-712.
39. Kim S, Rodgers RP, Marshall AG. Truly "exact" mass: elemental composition can be determined uniquely from molecular mass measurement at similar to 0.1 mDa accuracy for molecules up to similar to 500 Da. Int. J. Mass Spectrom. 2006; 251: 260-265.
40. Huang Q, Tezuka Y, Hatanaka Y, Kikuchi T, Nishi A, Tubaki K. Studies on metabolites of mycoparasitic fungi .5. Ion-spray ionization mass spectrometric analysis of Trichokonin-II, a peptaibol mixture obtained from the culture broth of Trichoderma koningii. Chem. Pharm. Bull. 1996; 44: 590-593.
41. Mohamed-Benkada M, Montagu M, Biard JF, Mondeguer F, Verite P, Dalgalarrondo M, Bissett J, Pouchus YF. New short peptaibols from a marine Trichoderma strain. Rapid Commun. Mass Spectrom. 2006; 20: 1176-1180.
42. Ruiz N, Wielgosz-Collin G, Poirier L, Grovel O, Petit KE, Mohamed-Benkada M, du Pont TR, Bissett J, Verite P, Barnathan G, Pouchus YF. New Trichobrachins, 11-residue peptaibols from a marine strain of Trichoderma longibrachiatum. Peptides 2007; 28: 1351-1358.
43. Becker D, Kiess M, Bruckner H. Structures of peptaibol antibiotics hypomurocin A and B from the ascomycetous fungus Hypocrea muroiana Hino et Katsumoto. Liebigs Annalen-Recueil. 1997; 767-772.
44. Degenkolb T, Dieckmann R, Nielsen KF, Grafenhan T, Theis C, Zafari D, Chaverri P, Ismaiel A, Bruckner H, von Dohren H, Thrane U, Petrini O, Samuels GJ. The Trichoderma brevicompactum clade: a separate lineage with new species, new peptaibiotics, and mycotoxins. Mycol Prog. 2008; 7: 177-219.
45. Degenkolb T, Grafenhan T, Nirenberg HI, Gams W, Bruckner H. Trichoderma brevicompactum complex: rich source of novel and recurrent plant-protective polypeptide antibiotics (peptaibiotics). J. Agric. Food Chem. 2006; 54: 7047-7061.
46. Iida A, Sanekata M, Fujita T, Tanaka H, Enoki A, Fuse G, Kanai M, Rudewicz PJ, Tachikawa E. Fungal metabolites. XVI. Structures of new peptaibols, trichokindins I-VII, from the fungus Trichoderma harzianum. Chem. Pharm. Bull. 1994; 42: 1070-1075.
47. Goulard C, Hlimi S, Rebuffat S, Bodo B. Trichorzins HA and MA, antibiotic peptides from Trichoderma harzianum. I. Fermentation, isolation and biological properties. J. Antibiot. 1995; 48: 1248-1253.
48. Shi M, Wang HN, Xie ST, Luo Y, Sun CY, Chen XL, Zhang YZ. Antimicrobial peptaibols, novel suppressors of tumor cells, targeted calcium-mediated apoptosis and autophagy in human hepatocellular carcinoma cells. Mol. Cancer 2010; 9: 26.
49. Chikanishi T, Hasumi K, Harada T, Kawasaki N, Endo A. Clonostachin, a novel peptaibol that inhibits platelet aggregation. J. Antibiot. 1997; 50: 105-110.