Dereplication of macrocyclic trichothecenes from extracts of filamentous fungi through UV and NMR profiles

Journal of Antibiotics

Volumn 63, Issue 9, 2010, Pages 539-544

  Sy Cordero, Arlene A ^a   Graf, Tyler N ^a   Wani, Mansukh C ^b   Kroll, David J ^c   Pearce, Cedric J ^d   Oberlies, Nicholas H ^a  

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

^b RTI INTERNATIONAL   (United States)

^c NORTH CAROLINA CENTRAL UNIVERSITY   (United States)

^d Mycosynthetix Inc   (United States)

Author keywords

dereplication; filamentous fungi; macrocyclic trichothecenes

Indexed keywords

ALKADIENE; ANTINEOPLASTIC AGENT; EPOXIDE; MACROCYCLIC COMPOUND; RORIDIN E; TRICHOTHECENE DERIVATIVE; UNCLASSIFIED DRUG; VERRUCARIN A;

ANTINEOPLASTIC ACTIVITY; ARTICLE; DRUG CONJUGATION; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; DRUG SYNTHESIS; FUNGUS; NONHUMAN; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; ULTRAVIOLET SPECTROSCOPY; CHEMICAL STRUCTURE; CHEMISTRY; HUMAN; ISOLATION AND PURIFICATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TUMOR CELL LINE; ULTRAVIOLET SPECTROPHOTOMETRY;

FUNGI;

ANTINEOPLASTIC AGENTS; CELL LINE, TUMOR; FUNGI; HUMANS; MACROCYCLIC COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; SPECTROPHOTOMETRY, ULTRAVIOLET; TRICHOTHECENES;

EID: 77957293285     PISSN: 00218820     EISSN: None     Source Type: Journal    
DOI: 10.1038/ja.2010.77     Document Type: Article

References (25)

1. Cole, R. J., Jarvis, B. B. & Schweikert, M. A. Handbook of Secondary Fungal Metabolites xi, 672 pps (Academic Press, Amsterdam, Boston, 2003).
2. Zhang, H. J. et al. Antimalarial agents from plants. III. Trichothecenes from Ficus fistulosa and Rhaphidophora decursiva. Planta Med. 68, 1088-1091 (2002).
3. Isaka, M., Punya, J., Lertwerawat, Y., Tanticharoen, M. & Thebtaranonth, Y. Antimalarial activity of macrocyclic trichothecenes isolated from the fungus Myrothecium verrucaria. J. Nat. Prod. 62, 329-331 (1999).
4. Jarvis, B. B. & Mazzola, E. P. Macrocyclic and other novel trichothecenes-their structure, synthesis, and biological significance. Acc. Chem. Res. 15, 388-395 (1982).
5. Matsumoto, M., Minato, H., Uotani, N., Matsumoto, K. & Kondo, E. New antibiotics from Cylindrocarpon sp. J. Antibiot. 30, 681-682 (1977).
6. Liu, J. Y. et al. Antifungal and new metabolites of Myrothecium sp. Z16, a fungus associated with white croaker Argyrosomus argentatus. J. Appl. Microbiol. 100, 195-202 (2006).
7. Garcia, C. C., Rosso, M. L., Bertoni, M. D., Maier, M. S. & Damonte, E. B. Evaluation of the antiviral activity against Junin virus of macrocyclic trichothecenes produced by the hypocrealean epibiont of Baccharis coridifolia. Planta Med. 68, 209-212 (2002).
8. Bloem, R. J., Smitka, T. A., Bunge, R. H., French, J. C. & Mazzola, E. P. Roridin-L-2, a new trichothecene. Tetrahedron Lett. 24, 249-252 (1983).
9. Smitka, T. A., Bunge, R. H., Bloem, R. J. & French, J. C. Two new trichothecenes, PD 113, 325 and PD 113, 326. J. Antibiot. 37, 823-828 (1984).
10. Wagenaar, M. M. & Clardy, J. Two new roridins isolated from Myrothecium sp. J. Antibiot. 54, 517-520 (2001).
11. Yu, N. J., Guo, S. X. & Lu, H. Y. Cytotoxic macrocyclic trichothecenes from the mycelia of Calcarisporium arbuscula Preuss. J. Asian Nat. Prod. Res. 4, 179-183 (2002).
12. Grove, J. F. Macrocyclic trichothecenes. Nat. Prod. Rep. 10, 429-448 (1993).
13. Hinkley, S. F. & Jarvis, B. B. Chromatographic method for Stachybotrys toxins. Methods Mol. Biol. 157, 173-194 (2001).
14. Jarvis, B. B., Midiwo, J. O. & Mazzola, E. P. Antileukemic compounds derived by chemical modification of macrocyclic trichothecenes. 2. Derivatives of roridin-A and roridin-H and verrucarin-A and verrucarin-J. J. Med. Chem. 27, 239-244 (1984).
15. Jarvis, B. B., Stahly, G. P., Pavanasasivam, G. & Mazzola, E. P. Anti-leukemic compounds derived from the chemical modification of macrocyclic trichothecenes. 1. Derivatives of verrucarin-A. J. Med. Chem. 23, 1054-1058 (1980).
16. Kinghorn, A. D. et al. Discovery of anticancer agents of diverse natural origin. Pure Appl. Chem. 81, 1051-1063 (2009).
17. Orjala, J., Oberlies, N. H., Pearce, C. J., Swanson, S. M. & Kinghorn, A. D. Discovery of potential anticancer agents from aquatic cyanobacteria, filamentous fungi, and tropical plants. in Bioactive Compounds from Natural Sources 2nd edn, (ed Tringali, C.) (London, Taylor & Francis: submitted).
18. Nielsen, K. F. & Smedsgaard, J. Fungal metabolite screening: database of 474 mycotoxins and fungal metabolites for dereplication by standardised liquid chromatography-UV-mass spectrometry methodology. J. Chromatogr. A 1002, 111-136 (2003).
19. Lang, G. et al. Evolving trends in the dereplication of natural product extracts: new methodology for rapid, small-scale investigation of natural product extracts. J. Nat. Prod. 71, 1595-1599 (2008).
20. Grove, J. F. Non-macrocyclic trichothecenes. Nat. Prod. Rep. 5, 187-209 (1988).
21. Namikoshi, M. et al. A new macrocyclic trichothecene, 12, 13-deoxyroridin E, produced by the marine-derived fungus Myrothecium roridum collected in Palau. J. Nat. Prod. 64, 396-398 (2001).
22. Saikawa, Y. et al. Toxic principles of a poisonous mushroom Podostroma cornu-damae. Tetrahedron 57, 8277-8281 (2001).
23. Gutzwiller, J. & Tamm, C. Uber die struktur von verrucarin B. Verrucarine und roridine, 6. Helv. Chim. Acta. 48, 177-182 (1965).
24. Alali, F. Q. et al. New colchicinoids from a native Jordanian meadow saffron, Colchicum brachyphyllum: isolation of the first naturally occurring dextrorotary colchicinoid. J. Nat. Prod. 68, 173-178 (2005).
25. Li, C. et al. Bioactive constituents of the stem bark of Mitrephora glabra. J. Nat. Prod. 72, 1949-1953 (2009).