Unusual biotransformation products of the sesquiterpene lactone budlein A by Aspergillus species

Phytochemistry

Volumn 96, Issue , 2013, Pages 92-100

  Arakawa, Nilton Syogo ^a,b   Gobbo Neto, Leonardo ^a   Ambrosio, Sérgio Ricardo ^c   Antonucci, Gilmara Ausech ^a   Sampaio, Suely Vilela ^a   Pupo, Mônica Tallarico ^a   Said, Suraia ^a   Schmidt, Thomas J ^d   Da Costa, Fernando Batista ^a,d  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b STATE UNIVERSITY OF LONDRINA   (Brazil)

^c UNIVERSIDADE DE FRANCA   (Brazil)

^d UNIVERSITY OF MÜNSTER   (Germany)

Author keywords

Aspergillus; Budlein A; Cytotoxic activity; Microbial transformation; Sesquiterpene lactones; Viguiera robusta

Indexed keywords

ASPERGILLUS; ASPERGILLUS NIGER; ASPERGILLUS TERREUS; ASTERACEAE; FUNGI; HELIANTHUS; VIGUIERA; VIGUIERA ROBUSTA;

ANTIINFLAMMATORY AGENT; BUDLEIN A; LACTONE; SESQUITERPENE;

ARTICLE; ASPERGILLUS; ASTERACEAE; BIOTRANSFORMATION; CHEMICAL STRUCTURE; CHEMISTRY; CYTOTOXICITY; EARLY DIAGNOSIS; GROWTH, DEVELOPMENT AND AGING; HL 60 CELL LINE; HUMAN; METABOLISM; MICROBIAL TRANSFORMATION; MICROBIOLOGY; NUCLEAR MAGNETIC RESONANCE; SESQUITERPENE LACTONES; STEREOISOMERISM; VIGUIERA ROBUSTA;

ASPERGILLUS; BUDLEIN A; CYTOTOXIC ACTIVITY; MICROBIAL TRANSFORMATION; SESQUITERPENE LACTONES; VIGUIERA ROBUSTA;

ANTI-INFLAMMATORY AGENTS; ASPERGILLUS; ASTERACEAE; BIOTRANSFORMATION; EARLY DETECTION OF CANCER; HL-60 CELLS; HUMANS; LACTONES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE, BIOMOLECULAR; SESQUITERPENES; SOIL MICROBIOLOGY; STEREOISOMERISM;

EID: 84888375046     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2013.09.022     Document Type: Article

References (43)

1. E.A. Abourashed, A.M. Clark, and C.D. Hufford Microbial models of mammalian metabolism of xenobiotics: an updated review Curr. Med. Chem. 6 1999 359 374 (Pubitemid 29230819)
2. E. Adelin, M.T. Martin, M.F. Bricot, S. Cortial, P. Retailleau, and J. Ouazzani Biotransformation of natural compounds: unexpected thio conjugation of Sch-642305 with 3-mercaptolactate catalyzed by Aspergillus niger ATCC 16404 cells Phytochemistry 84 2012 135 140
3. N.S. Arakawa, K. Schorr, S.R. Ambrosio, I. Merfort, and F.B. Da Costa Further sesquiterpene lactones of Viguiera robusta and their potential anti-inflammatory activity: inhibition of human neutrophil elastase release Z. Naturforsch. 63 2008 533 538
4. Chemical Computing Group, Molecular Operating Environment (MOE), rel. 2011.10 (2011), Chemical Computing Group Inc., 1010 Sherbooke St. West, Suite #910, Montreal, QC, Canada, H3A 2R7.
5. M.I. Choudhary, R. Ranjit, Atta-ur-Rahman, K.P. Devkota, S.G. Musharraf, and T.M. Shrestha Hydroxylation of the sesterterpene leucosceptrine by the fungus Rhizopus stolonifer Phytochemistry 67 2006 439 443 (Pubitemid 43213045)
6. J.C. Coll, and B.F. Bowden The application of vacuum liquid chromatography to the separation of terpene mixtures J. Nat. Prod. 49 1986 934 936
7. F.B. Da Costa, K. Schorr, N.S. Arakawa, E.E. Schilling, and O. Spring Infraspecific variation in the chemistry of glandular trichomes of two Brazilian Viguiera species (Heliantheae, Asteraceae) J. Braz. Chem. Soc. 3 2001 403 407
8. F.B. Da Costa, L. Terfloth, and J. Gasteiger Sesquiterpene lactone-based classification of three Asteraceae tribes: a study based on self-organizing neural networks applied to chemosystematics Phytochemistry 66 2005 345 353 (Pubitemid 40169994)
9. M.J.S. Dewar, E.G. Zoebisch, E.F. Healy, and J.J.P. Stewart Development and use of quantum mechanical molecular models. 76. AM1: a new general purpose quantum mechanical molecular model J. Amer. Chem. Soc. 107 1985 3902 3909
10. A.M. Galal, A.S. Ibrahim, J.S. Mossa, and F.S. El-Feraly Microbial transformation of parthenolide Phytochemistry 51 1999 761 765 (Pubitemid 29289196)
11. A.J. García-Piñeres, V. Castro, G. Mora, T.J. Schmidt, E. Strunck, H.L. Pahl, and I. Merfort Cysteine 38 in p65/NF-kappaB plays a crucial role in DNA binding inhibition by sesquiterpene lactones J. Biol. Chem. 276 2001 39713 39720
12. C.A.G. Haasnoot, F.A.A.M. De Leeuw, and C. Altona The relationship between proton-proton NMR coupling constants ans substituent electronegativities - I: an empirical generalization of the Karplus equation Tetrahedron 36 1980 2783 2792
13. S.P. Hehner, T.G. Hofmann, W. Droge, and M.L. Schmitz The antiinflammatory sesquiterpene lactone parthenolide inhibits NF-kappa B by targeting the I kappa B kinase complex J. Immunol. 163 1999 5617 5623
14. W. Herz, and V.L. Goedken Structure of goyazensolide and its congeners J. Org. Chem. 47 1982 2798 2800
15. G.N.K. Kumari, S. Masilamani, M.R. Ganesh, and S. Aravind Microbial transformation of zaluzanin-D Phytochemistry 62 2003 1101 1104 (Pubitemid 36323481)
16. S.M. Kupchan, M.A. Eakin, and A.M. Thomas Tumor inhibitors. 69. Structure-cytotoxicity relationship among the sesquiterpene lactones J. Med. Chem. 12 1971 1147 1152
17. V. Lamare, and R. Furstoss Bioconversion of sesquiterpenes Tetrahedron 46 1990 4109 4132 (Pubitemid 20246201)
18. K.H. Lee, E.S. Huang, C. Piantadosi, J.S. Pagano, and T.A. Geissman Cytotoxicity of sesquiterpene lactones Cancer Res. 31 1971 1649 1654
19. P.W. Le Quesne, M.D. Menachery, M.P. Pastore, C.J. Kelley, T.F. Brennan, K.D. Onan, and R.F. Raffauf Antitumor plants. 12. Further sesquiterpenoid constituents of Lychnophora affinis Gardn. (Compositae). X-ray structure analysis of lychnophorolide A J. Org. Chem. 47 1982 1519 1521 (Pubitemid 12070313)
20. G. Lyss, T.J. Schmidt, I. Merfort, and H.L. Pahl Helenalin, an anti-inflammatory sesquiterpene lactone from Arnica, selectively inhibits transcription factor NF-kappaB Biol. Chem. 378 1997 951 961 (Pubitemid 27438016)
21. I. Merfort Perspectives on sesquiterpene lactones in inflammation and cancer Curr. Drug Targets 12 2011 1560 1573
22. T. Mosmann Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxic assays J. Immunol. Methods 65 1983 55 63 (Pubitemid 14203433)
23. R. Nicolete, N.S. Arakawa, C. Rius, A. Nomizo, P.J. Jose, F.B. Da Costa, M. Sanz, and L.H. Faccioli Budlein A from Viguiera robusta inhibits leukocyte-endothelial cell interactions, adhesion molecule expression and inflammatory mediators release Phytomedicine 16 2009 904 915
24. M. Niehues, V.P. Barros, F.S. Emery, M. Dias-Baruffi, M.D. Assis, and N.P. Lopes Biomimetic in vitro oxidation of lapachol: a model to predict and analyse the in vivo phase I metabolism of bioactive compounds Eur. J. Med. Chem. 54 2012 804 812
25. I.A. Parshikov, B. Miriyala, K.M. Muraleedharn, M.A. Avery, and J.S. Williamson Microbial transformation of artemisinin to 5-hydroxyartemisinin by Eurotium amstelodami and Aspergillus niger J. Ind. Microbiol. Biotechnol. 33 2006 349 352
26. B.A. Rocha, M.T. Pupo, G.A. Antonucci, S.V. Sampaio, R.M.A. Paiva, S. Said, L. Gobbo-Neto, and F.B. Da Costa Microbial transformation of the sesquiterpene lactone tagitinin C by the fungus Aspergillus terreus J. Ind. Microbiol. Biotechnol. 39 2012 1719 1724
27. P. Roche, N. Rosas, J. Taboada, M. González Diddí, and J. Tellez Algunos derivados de las budleinas A y B y actividad citotoxica em dos lineas celulares de la substancia A Rev. Latinoamer. Quím. 10 1979 145 149
28. A. Romo de Vivar, C. Guerrero, E. Díaz, E.A. Bratoeff, and L. Jiménez The germacranolides of Viguiera buddleiaeformis structures of budlein-A and -B Phytochemistry 15 1976 525 527
29. T.J. Schmidt Helenanolide-type sesquiterpene lactones-III. Rates and stereochemistry in the reaction of helenalin and related helenanolides with sulfhydryl containing biomolecules Bioorg. Med. Chem. 5 1997 645 653 (Pubitemid 27199388)
30. T.J. Schmidt Toxic activities of sesquiterpene lactones - structural and biochemical aspects Curr. Org. Chem. 3 1999 577 605
31. T.J. Schmidt Structure-activity relationships of sesquiterpene lactones Atta-ur-Rahman Studies in Natural Products Chemistry vol. 33 2006 Elsevier Amsterdam 309 392
32. T.J. Schmidt, and J. Heilmann Quantitative structure-cytotoxicity relationships of sesquiterpene lactones derived from partial charge (Q)-based fractional accessible surface area descriptors (Q-frASAs) Quant. Struct.-Act. Relat. 21 2002 276 287 (Pubitemid 34951598)
33. K. Schorr, A.J. García-Piñeres, B. Siedle, I. Merfort, and F.B. Da Costa Guaianolides from Viguiera gardneri inhibit the transcription factor NF-κB Phytochemistry 60 2002 733 740 (Pubitemid 34857125)
34. F.C. Seaman Sesquiterpene lactones as taxonomic characters in the Asteraceae Bot. Rev. 48 1982 123 551
35. B. Siedle, A.J. García-Piñeres, R. Murillo, Schulte-Mönting, V. Castro, P. Rüngeler, C.A. Klaas, F.B. Da Costa, W. Kisiel, and I. Merfort Quantitative structure-activity relationship of sesquiterpene lactones as inhibitors of the transcription factor NF-κB J. Med. Chem. 47 2004 6042 6054 (Pubitemid 39507346)
36. W.C. Still, M. Kahn, and A. Mitra A rapid chromatographic technique for preparative separations with moderate resolution J. Org. Chem. 43 1978 2923 2925
37. N. Tabata, H. Tomoda, and S. Omura Eurabulenols, inhibitors of cholesteryl ester transfer protein produced by Penicillium sp. FO-5637. II. Structure elucidation of eurabulenols A and B J. Antibiot. 51 1998 624 628 (Pubitemid 28398751)
38. P.G. Taylor, O.A.D. Loo, J.A. Bonilla, and R. Murillo Anticancer activities of two sesquiterpene lactones, millerenolide and thieleanin isolated from Viguiera sylvatica and Decachaeta thieleana Fitoterapia 79 2008 428 432
39. D.A.R. Valério, T.M. Cunha, N.S. Arakawa, H.P. Lemos, F.B. Da Costa, C.A. Parada, S.H. Ferreira, F.Q. Cunha, and W.A. Verri Jr. Anti-inflammatory and analgesic effects of the sesquiterpene lactone budlein A in mice: inhibition of cytokine production-dependent mechanism Eur. J. Pharmacol. 562 2007 155 163 (Pubitemid 46466751)
40. C. Vézina Biotransformations J. Bu'lock, J. Kristiansen, Basic Biotechnology 1987 Academic Press London 461 483
41. M.L. Villarreal, L. Alvarez, D. Alonso, V. Navarro, P. García, and G. Delgado Cytotoxic and antimicrobial screening of selected terpenoids from Asteraceae species J. Ethnopharmacol. 42 1994 25 29 (Pubitemid 24102223)
42. J. Zhang, H. Guo, Y. Tian, P. Liu, N. Li, J. Zhou, and D. Guo Biotransformation of 20(S)-protopanaxatriol by Mucor spinosus and the cytotoxic structure activity relationships of the transformed products Phytochemistry 68 2007 2523 2530 (Pubitemid 47451448)
43. X. Zhang, M. Ye, Y.-h. Dong, Y. Dong, H.-b. Hu, S.-j. Tao, J. Yin, and D.-a. Guo Biotransformation of bufadienolides by cell suspension cultures of Saussurea involucrata Phytochemistry 72 2011 1779 1785