Helicusin E, isochromophilone X and isochromophilone XI: New chloroazaphilones produced by the fungus Bartalinia robillardoides strain LF550

Marine Drugs

Volumn 11, Issue 3, 2013, Pages 800-816

  Jansen, Nils ^a   Ohlendorf, Birgit ^a   Erhard, Arlette ^a   Bruhn, Torsten ^b   Bringmann, Gerhard ^b   Imhoff, Johannes F ^a  

^a GEOMAR HELMHOLTZ CENTRE FOR OCEAN RESEARCH KIEL   (Germany)

^b UNIVERSITY OF WÜRZBURG   (Germany)

Author keywords

Azaphilone; Bartalinia robillardoides; Marine natural product; Pentaketide; Tethya aurantium

Indexed keywords

ACETYLCHOLINESTERASE; ANTIFUNGAL AGENT; ANTIINFECTIVE AGENT; BARTANOLIDE; CHLORAMPHENICOL; CLOTRIMAZOLE; CYTOTOXIC AGENT; DEACETYLSCLEROTIORIN; HELICUSIN A; HELICUSIN E; ISOCHROMOPHILONE X; ISOCHROMOPHILONE XI; NATURAL PRODUCT; NYSTATIN; PHOSPHODIESTERASE IV; ROLIPRAM; UNCLASSIFIED DRUG;

ANTIBACTERIAL ACTIVITY; ANTIFUNGAL ACTIVITY; ARTICLE; BACILLUS SUBTILIS; BARTALINIA ROBILLARDOIDES; CANDIDA ALBICANS; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; ENZYME INHIBITION; FUNGUS; HUMAN; HUMAN CELL; IC 50; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; NUCLEOTIDE SEQUENCE; PHYTOPHTHORA INFESTANS; SEPTORIA TRITICI; STAPHYLOCOCCUS; STAPHYLOCOCCUS LENTUS; TRICHOPHYTON RUBRUM; TUMOR CELL; XANTHOMONAS CAMPESTRIS;

BARTALINIA; BARTALINIA ROBILLARDOIDES; FUNGI; TETHYA AURANTIUM;

EID: 84875761962     PISSN: None     EISSN: 16603397     Source Type: Journal    
DOI: 10.3390/md11030800     Document Type: Article

References (38)

1. Rateb, M.E.; Ebel, R. Secondary metabolites of fungi from marine habitats. Nat. Prod. Rep. 2011, 28, 290-344.
2. Gangadevi, V.; Muthumary, J. Taxol, an anticancer drug produced by an endophytic fungus Bartalinia robillardoides Tassi, isolated from a medicinal plant, Aegle marmelos Correa ex Roxb. World J. Microb. Biot. 2008, 24, 717-724.
3. Chruma, J.J.; Moon, S.-J.; Sanford, W.E., Jr. Azaphilone -bromoacetates (AzBs): Fluorescent linchpin reagents for the inter- and intramolecular cross-linkage of primary amines to thiols. Lett. Org. Chem. 2009, 6, 367-371.
4. Wei, W.G.; Yao, Z.J. Synthesis studies toward chloroazaphilone and vinylogous gamma-pyridones: Two common natural product core structures. J. Org. Chem. 2005, 70, 4585-4590.
5. Osmanova, N.; Schultze, W.; Ayoub, N. Azaphilones: A class of fungal metabolites with diverse biological activities. Phytochem. Rev. 2010, 9, 315-342.
6. Wiese, J.; Ohlendorf, B.; Blümel, M.; Schmaljohann, R.; Imhoff, J.F. Phylogenetic identification of fungi isolated from the marine sponge Tethya aurantium and identification of their secondary metabolites. Mar. Drugs 2011, 9, 561-585.
7. Yoshida, E.; Fujimoto, H.; Baba, M.; Yamazaki, M. Four new chlorinated azaphilones, helicusins A-D, closely related to 7-epi-sclerotiorin, from an ascomycetous fungus, Talaromyces helicus. Chem. Pharm. Bull. (Tokyo) 1995, 43, 1307-1310.
8. Sun, X.L.; Takayanagi, H.; Matsuzaki, K.; Tanaka, H.; Furuhata, K.; Omura, S. Synthesis and inhibitory activities of isochromophilone analogues against gp120-CD4 binding. J. Antibiot. (Tokyo) 1996, 49, 689-692.
9. Michael, A.P.; Grace, E.J.; Kotiw, M.; Barrow, R.A. Isochromophilone IX, a novel GABA-containing metabolite isolated from a cultured fungus, Penicillium sp. Aust. J. Chem. 2003, 56, 13-15.
10. Nam, J.Y.; Kim, H.K.; Kwon, J.Y.; Han, M.Y.; Son, K.H.; Lee, U.C.; Choi, J.D.; Kwon, B.M. 8-O-Methylsclerotiorinamine, antagonist of the Grb2-SH2 domain, isolated from Penicillium multicolor. J. Nat. Prod. 2000, 63, 1303-1305.
11. Yang, D.J.; Tomoda, H.; Tabata, N.; Masuma, R.; Omura, S. New isochromophilones VII and VIII produced by Penicillium sp. FO-4164. J. Antibiot. (Tokyo) 1996, 49, 223-229.
12. Wu, S.H.; Chen, Y.W.; Shao, S.C.; Wang, L.D.; Li, Z.Y.; Yang, L.Y.; Li, S.L.; Huang, R. Ten-membered lactones from Phomopsis sp., an endophytic fungus of Azadirachta indica. J. Nat. Prod. 2008, 71, 731-734.
13. Pilli, R.A.; Victor, M.M.; de Meijere, A. First total synthesis of aspinolide B, a new pentaketide produced by Aspergillus ochraceus. J. Org. Chem. 2000, 65, 5910-5916.
14. Steyn, P.S.; Vleggaar, R. The structure of dihydrodeoxy-8-epi-austdiol and the absolute configuration of the azaphilones. J. Chem. Soc. Perkin 1 1976, 204-206; doi:10.1039/P19760000204.
15. Whalley, W.B.; Ferguson, G.; Marsh, W.C.; Restivo, R.J. The chemistry of fungi. Part LXVIII. The absolute configuration of (+)-sclerotiorin and of the azaphilones. J. Chem. Soc. Perkin 1 Trans. 1976, 1366-1369; doi:10.1039/ P19760001366.
16. Germain, A.R.; Bruggemeyer, D.M.; Zhu, J.; Genet, C.; O'Brien, P.; Porco, J.A. Synthesis of the azaphilones (+)-sclerotiorin and (+)-8-O- methylsclerotiorinamine utilizing (+)-sparteine surrogates in copper-mediated oxidative dearomatization. J. Org. Chem. 2011, 76, 2577-2584.
17. Berova, N.; Di Bari, L.; Pescitelli, G. Application of electronic circular dichroism in configurational and conformational analysis of organic compounds. Chem. Soc. Rev. 2007, 36, 914-931.
18. Bringmann, G.; Götz, D.; Bruhn, T. The Online Stereochemical Analysis of Chiral Compounds by HPLC-ECD Coupling in Combination with Quantum-Chemical Calculations. In Comprehensive Chiroptical Spectroscopy; Berova, N., Woody, R.W., Polavarapu, P., Nakanishi, K., Eds.; John Wiley & Sons: Hoboken, NJ, USA, 2012; Volume 2, pp. 355-420.
19. Grebner, C.; Becker, J.; Stepanenko, S.; Engels, B. Efficiency of tabu-search-based conformational search algorithms. J. Comput. Chem. 2011, 32, 2245-2253.
20. Bringmann, G.; Bruhn, T.; Maksimenka, K.; Hemberger, Y. The assignment of absolute stereostructures through quantum chemical circular dichroism calculations. Eur. J. Org. Chem. 2009, 17, 2717-2727.
21. Arunpanichlert, J.; Rukachaisirikul, V.; Sukpondma, Y.; Phongpaichit, S.; Tewtrakul, S.; Rungjindamai, N.; Sakayaroj, J. Azaphilone and isocoumarin derivatives from the endophytic fungus Penicillium sclerotiorum PSU-A13. Chem. Pharm. Bull. (Tokyo) 2010, 58, 1033-1036.
22. Schulz, D.; Beese, P.; Ohlendorf, B.; Erhard, A.; Zinecker, H.; Dorador, C.; Imhoff, J.F. Abenquines A-D: Aminoquinone derivatives produced by Streptomyces sp. strain DB634. J. Antibiot. (Tokyo) 2011, 64, 763-768.
23. Kim, B.-Y.; Willbold, S.; Kulik, A.; Helaly, S.E.; Zinecker, H.; Wiese, J.; Imhoff, J.F.; Goodfellow, M.; Süssmuth, R.D.; Fiedler, H.-P. Elaiomycins B and C, novel alkylhydrazides produced by Streptomyces sp. BK 190. J. Antibiot. (Tokyo) 2011, 64, 595-597.
24. Jorgensen, W.L.; Maxwell, D.S.; TiradoRives, J. Development and testing of the OPLS all-atom force field on conformational energetics and properties of organic liquids. J. Am. Chem. Soc. 1996, 118, 11225-11236.
25. Stewart, J.J.P. MOPAC2012, version 12.157L; Stewart Computational Chemistry: Colorada Springs, CO, USA, 2012.
26. Schäfer, A.; Huber, C.; Ahlrichs, R. Fully optimized contracted gaussian-basis sets of triple zeta valence quality for atoms Li to Kr. J. Chem. Phys. 1994, 100, 5829-5835.
27. Grimme, S. Semiempirical GGA-type density functional constructed with a long-range dispersion correction. J. Comput. Chem. 2006, 27, 1787-1799.
28. Frisch, M.J.; Trucks, G.W.; Schlegel, H.B.; Scuseria, G.E.; Robb, M.A.; Cheeseman, J.R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G.A.; et al. Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford, CT, USA, 2010.
29. Grimme, S. Improved second-order Møller-Plesset perturbation theory by separate scaling of parallel- and antiparallel-spin pair correlation energies. J. Chem. Phys. 2003, 118, 9095-9102.
30. Weigend, F.; Ahlrichs, R. Balanced basis sets of split valence, triple zeta valence and quadruple zeta valence quality for H to Rn: Design and assessment of accuracy. Phys. Chem. Chem. Phys. 2005, 7, 3297-3305.
31. Sinnecker, S.; Rajendran, A.; Klamt, A.; Diedenhofen, M.; Neese, F. Calculation of solvent shifts on electronic g-tensors with the conductor-like screening model (COSMO) and its self-consistent generalization to real solvents (Direct COSMO-RS). J. Phys. Chem. A 2006, 110, 2235-2245.
32. Karton, A.; Tarnopolsky, A.; Lamere, J.F.; Schatz, G.C.; Martin, J.M.L. Highly accurate first-principles benchmark data sets for the parametrization and validation of density functional and other approximate methods. Derivation of a robust, generally applicable, double-hybrid functional for thermochemistry and thermochemical kinetics. J. Phys. Chem. A 2008, 112, 12868-12886.
33. Kossmann, S.; Neese, F. Efficient structure optimization with second-order many-body perturbation theory: The RIJCOSX-MP2 method. J. Chem. Theory Comput. 2010, 6, 2325-2338.
34. Petrenko, T.; Kossmann, S.; Neese, F. Efficient time-dependent density functional theory approximations for hybrid density functionals: Analytical gradients and parallelization. J. Chem. Phys. 2011, 134, 054116.
35. Neese, F.; Becker, U.; Ganyushin, D.; Hansen, A.; Liakos, D.; Kollmar, C.; Koßmann, S.; Petrenko, T.; Reimann, C.; Riplinger, C.; et al. ORCA - An Ab Initio, Density Functional and Semiempirical Program Package, version 2.9.1; Max Planck Institute for Bioinorganic Chemistry: Mühlheim, Germany, 2012.
36. Bruhn, T.; Schaumlöffel, A.; Hemberger, Y.; Bringmann, G. SpecDis, version 1.53; University Würzburg: Würzburg, Germany, 2012.
37. Dong, J.Y.; Zhou, Y.P.; Li, R.; Zhou, W.; Li, L.; Zhu, Y.H.; Huang, R.; Zhang, K.Q. New nematicidal azaphilones from the aquatic fungus Pseudohalonectria adversaria YMF1.01019. FEMS Microbiol. Lett. 2006, 264, 65-69.
38. Bell, P.J.L.; Karuso, P. Epicocconone, a novel fluorescent compound from the fungus Epicoccum nigrum. J. Am. Chem. Soc. 2003, 125, 9304-9305.