Fungal strains as catalysts for the biotransformation of halolactones by hydrolytic dehalogenation with the dimethylcyclohexane system

Molecules

Volumn 17, Issue 8, 2012, Pages 9741-9753

  Grabarczyk, Małgorzata ^a  

^a WROC AW UNIVERSITY OF ENVIRONMENTAL AND LIFE SCIENCES   (Poland)

Author keywords

Biotransformation; Fusarium species; Hydrolytic dehalogenation; Lactones

Indexed keywords

CYCLOHEXANE DERIVATIVE; LACTONE;

ARTICLE; BIOCATALYSIS; BIOTRANSFORMATION; CHEMISTRY; FUNGUS; HALOGENATION; HYDROLYSIS; METABOLISM;

BIOCATALYSIS; BIOTRANSFORMATION; CYCLOHEXANES; FUNGI; HALOGENATION; HYDROLYSIS; LACTONES;

EID: 84865527539     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules17089741     Document Type: Article

References (63)

1. Vairappan, C.S.; Suzuki, M.; Ishii, T.; Okino, T.; Abe, T.; Masuda, M. Antibacterial activity of halogenated sesquiterpenes from Malaysian Laurencia spp. Phytochemistry 2008, 69, 2490-2494.
2. Ji, N.Y.; Li, X.M.; Wang, B.G. Sesquiterpenes and Other Metabolites from the Marine Red Alga Laurencia composita (Rhodomelaceae). Helv. Chim. Acta 2010, 93, 2281-2286.
3. Kladi, M.; Vagias, C.; Papazafiri, P.; Furnari G.; Serio, D.; Roussis, V. New sesquiterpenes from the red alga Laurencia microcladia. Tetrahedron 2007, 63, 7606-7611.
4. Su, H.; Shi, D.Y.; Li, J.; Guo, S.J.; Li, L.L.; Yuan, Z.H.; Zhu, X.B. Sesquiterpenes from Laurencia similes. Molecules 2009, 14, 1889-1897.
5. Rudi, A.; Benayahu, Y.; Kashman, Y. Negombins A-I, new chlorinated polyfunctional diterpenoids from the marine sponge Negombata species. Org. Lett. 2007, 9, 2337-2340.
6. Sung, P.J.; Chiang, M.Y.; Tsai, W.T.; Su, J.H.; Su, Y.M.; Wu, Y.C. Chlorinated briarane-type diterpenoids from the gorgonian coral Ellisella robusta (Ellisellidae). Tetrahedron 2007, 63, 12860-12865.
7. Diaz-Marrero, A.R.; Brito, I.; de la Rosa, J.M.; D'Croz, L.; Fabelo, O.; Ruiz-Perez, C.; Darias, J.; Cueto, M. Novel lactone chamigrene-derived metabolites from Laurencia majuscule. Eur. J. Org. Chem. 2009, 1407-1411.
8. Reed, K.A.; Manam, R.R.; Mitchell, S.S.; Xu, J.; Teisan, S.; Chao, T.H.; Deyanat-Yazdi, G.; Neuteboom, S.T.C.; Lam, K.S.; Potts, B.C.M. Salinosporamides D-J from the marine actinomycete Salinispora tropica, bromosalinosporamide, and thioester Derivatives are potent inhibitors of the 20S proteasome. J. Nat. Prod. 2007, 70, 269-276.
9. Levenfors, J.J.; Hedman, R.; Thaning, C.; Gerhardson, B.; Welch, C.J. Broad-spectrum antifungal metabolites produced by the soil bacterium Serratia plymuthica A 153. Soil Biol. Biochem. 2004, 36, 677-685.
10. Thaning, C.; Welch, C.J.; Borowicz, J.J.; Hedman, R.; Gerhardson, B. Suppression of Sclerotinia sclerotiorum apothecial formation by the soil bacterium Serratia plymuthica: Identification of a chlorinated macrolide as one of the causal agents. Soil Biol. Biochem. 2001, 33, 1817-1826.
11. Gutirrez-Cepeda, A.; Fernndez, J.J.; Gil, L.V.; Lopez-Rodriguez, M.; Norte. M.; Souto, M.L. Nonterpenoid C15 Acetogenins from Laurencia marilzae. J. Nat. Prod. 2011, 74, 441-448.
12. Nam, S.J.; Gaudncio, S.P.; Kauffman, C.A.; Jensen, P.R.; Kondratyuk, T.P.; Marler, L.E.; Pezzuto, J.M.; Fenical, W. Fijiolides A and B, inhibitors of TNF-α-induced NFκB activation, from a marine-derived sediment bacterium of the genus Nocardiopsis. J. Nat. Prod. 2010, 73, 1080-1086.
13. Yin, S.; Boyle, G.M.; Carroll, A.R.; Kotiw, M.; Dearnaley, J.; Quinn, R.J.; Davis, R.A. Caelestines A-D, Brominated quinolinecarboxylic acids from the Australian ascidian Aplidium caelestis. J. Nat. Prod. 2010, 73, 1586-1589.
14. Lhullier, C.; Falkenberg; M.; Ioannou, E.; Quesada, A.; Papazafiri, P.; Horta, P.A.; Schenkel, E.P.; Vagias, C.; Roussis, V. Cytotoxic halogenated metabolites from the Brazilian red alga Laurencia catarinensis. J. Nat. Prod. 2010, 73, 27-32.
15. Han, B.; McPhail, K.L.; Gross, H.; Goeger, D.E.; Mooberry, S.L.; Gerwick, W.H. Isolation and structure of five lyngbyabellin derivatives from a Papua New Guinea collection of the marine cyanobacterium Lyngbya majuscula. Tetrahedron 2005, 61, 11723-11729.
16. Zhang, L.; An, R.; Wang, J.; Sun, N.; Zhang, S.; Hu, J.; Kuai, J. Exploring novel bioactive compounds from marine microbes. Curr. Opin. Microbiol. 2005, 8, 276-281.
17. Zidorn, C.; Ellmerer, E.P.; Konwalinka, G.; Schwaiger, N.; Stuppner, H. 13-Chloro-3-O-β-Dglucopyranosylsolstitialin from Leontodon palisae: The first genuine chlorinated sesquiterpene lactone glucoside. Tetrahedron Lett. 2004, 45, 3433-3436.
18. Fehr, D.; Barlow, R.; McAtee, J.; Hemscheidt, T.K. Highly brominated antimicrobial metabolites from a marine Pseudoalteromonas sp. J. Nat. Prod. 2010, 73, 1963-1966.
19. Yang, X.; Davis, R.A.; Buchanan, M.S.; Duffy, S.; Avery, V.M.; Camp, D.; Quinn, R.J. Antimalarial bromotyrosine derivatives from the Australian marine sponge Hyattella sp. J. Nat. Prod. 2010, 73, 985-987.
20. Särkkä, J.; Paasivirta, J.; Häsänen, E.; Koistinen, J.; Manninen, P.; Mäntykoski, K.; Rantio, T.; Welling, L. Organic chlorine compounds in lake sediments. VI. Two bottom sites of Lake Ladoga near pulp mills. Chemosphere 1993, 26, 2147-2160.
21. Koistinen, J.; Herve, S.; Ruokojärvi, P.; Koponen, J.; Vartiainen, T. Persistent organic pollutants in two Finnish watercourses: Levels, congener profiles and source estimation by mussel incubation. Chemosphere 2010, 80, 625-633.
22. Papazi, A.; Kotzabasis, K. Bioenergetic strategy of microalgae for the biodegradation of phenolic compounds - Exogenously supplied energy and carbon sources adjust the level of biodegradation. J. Biotechnol. 2007, 129, 706-716.
23. Papazi, A.; Kotzabasis, K. Inductive and resonance effects of substituents adjust the microalgal biodegradation of toxical phenolic compounds. J. Biotechnol. 2008, 135, 366-373.
24. Zanaroli, G.; Pérez-Jiménez, J.R.; Young, L.Y.; Marchetti, L.; Fava, F. Microbial Reductive Dechlorination of Weathered and Exogenous Co-planar Polychlorinated Biphenyls (PCBs) in an Anaerobic Sediment of Venice Lagoon. Biodegradation 2006, 17, 19-27.
25. Hongsawat, P.; Vangnai, A.S. Biodegradation pathways of chloroanilines by Acinetobacter baylyi strain. J. Hazard Mater. 2011, 186, 1300-1307.
26. Bao, H.; Gao, J.; Liu, Y.; Su, Y. A study of biodegradation/γ- irradiation on the degradation of pchloronitrobenzene. Radiat. Phys. Chem. 2009, 78, 1137-1139.
27. Katapodis, P.; Moukouli, M.; Christakopoulos, P. Biodegradation of indole at high concentration by persolvent fermentation with the thermophilic fungus Sporotrichum. Int. Biodeterior. Biodegradat. 2007, 60, 267-272.
28. Li, J.; Cai, W.; Zhu, L. The characteristics and enzyme activities of 4-chlorophenol biodegradation by Fusarium sp. Bioresour. Technol. 2011, 102, 2985-2989.
29. Muzikar, M.; Kresinova, Z.; Svobodova, K.; Filipova, A.; Cvancarova, M.; Cajthamlova, K.; Cajthaml, T. Biodegradation of chlorobenzoic acids by ligninolytic fungi. J. Hazard. Mater. 2011, 196, 386-394.
30. Wang, C.; Xi, J.Y.; Hu, H.Y.; We, X.H. Biodegradation of Gaseous Chlorobenzene by White-rot Fungus Phanerochaete chrysosporium. Biomed. Enviro. Sci. 2008, 21, 474-478.
31. Hardman, D.J. Biotransformation of Halogenated Compounds. Crit. Rev. Biotechnol. 1991, 11, 1-40.
32. Janssen, D.B. Evolving haloalkane dehalogenases. Curr. Opin. Chem. Biol. 2004, 8, 150-159.
33. Janssen, D.B.; Oppentocht, J.E.; Poelarends, G.J. Microbial dehalogenation. Curr. Opin. Biotechnol. 2001, 12, 254-258.
34. Grotowska, A.K.; Wawrzeńczyk, C. Lactones 13. Biotransformation of iodolactones. J. Mol. Catal. B: Enzym. 2002, 19-20, 203-208.
35. Grabarczyk, M.; Białońska, A. Biotransformations of chloro-, bromo- and iodolactone with trimethylcyclohexane system using fungal strains. Biocatal. Biotransform. 2010, 28, 408-414.
36. Gładkowski, W.; Mazur, M.; Białońska, A.; Wawrzeńczyk, C. Lactones 35. Metabolism of iodolactones with cyclohexane ring in Absidia cylindrospora culture. Enzyme Microb. Technol. 2011, 48, 326-333.
37. Borges, K.B.; Borges, W.S.; Durán-Patrón, R.; Pupo, M.T.; Bonato, P.S.; Collado, I.C. Stereoselective biotransformations using fungi as biocatalysts. Tetrahedron: Asymmetry 2009, 20, 385-397.
38. Rodrigues-Filho, E.; Magnani, R.F.; Xie, W.; Mirocha, C.J.; Pathre, S.V; Hydroxylation of the Labdane Diterpene Cupressic Acid by Fusarium graminearum. J. Braz. Chem. Soc. 2002, 13, 266-269.
39. Ghoumari, H.; Benajiba, M.H.; Garcia-Granados, A.; Fernandez, A.; Martinez, A.; Rivas, F.; Arias, J.M. Biotransformations of ent-18-acetoxy-6- ketomanoyl oxides epimers at C-13 with filamentous fungi. Phytochemistry 2006, 67, 2294-2302.
40. Garcia-Granados, A.; Fernandez, A.; Gutierrez, M.C.; Martinez, A.; Quiros, R.; Rivas, F.; Arias, J.M. Biotransformation of ent-13-epi-manoyl oxides difunctionalized at C-3 and C-12 by filamentous fungi. Phytochemistry 2004, 65, 107-115.
41. Tapia, A.A.; Vallejo, M.D.; Gouiric, S.C.; Feresin, G.E.; Rossomando, P.C.; Bustos, D.A. Hydroxylation of dehydroabietic acid by Fusarium species. Phytochemistry 1997, 46, 131-133.
42. Świzdor, A.; Kołek, T. Transformations of 4- and 17α-substituted testosterone analogues by Fusarium culmorum. Steroids 2005, 70, 817-824.
43. Kumari, G.N.K.; Masilamani, S.; Ganesh, M.R.; Aravind, S. Microbial transformation of zaluzanin-D. Phytochemistry 2003, 62, 1101-1104.
44. Nobilec, E.; Aniol, M.; Wawrzeńczyk, C. Lactones 1. Hydroxylation of dihydro-β- campholenolactone by Fusarium culmorum. Tetrahedron 1994, 50, 10339-10344.
45. Gładkowski, W.; Grabarczyk, M.; Konopka, M.; Wawrzeńczyk, C. Lactones 20: Biohydroxylation of saturated bicyclic γ-lactones with the substituted cyclohexane system. J. Mol. Catal. B Enzym. 2004, 29, 13-17.
46. Kaplan, O.; Nikolaou, K.; Pisvejcova, A.; Martinkova, L. Hydrolysis of nitriles and amides by filamentous fungi. Enzyme Microb. Technol. 2006, 38, 260-264.
47. Bartmańska, A.; Huszcza, E.; Tronina, T. Transformation of isoxanthohumol by fungi. J. Mol. Catal. B: Enzym. 2009, 61, 221-224.
48. Marostica, M.R., Jr.; Pastore, G.M. Production of R-(+)- α-terpineol by the biotransformation of limonene from orange essential oil, using cassava waste water as medium. Food Chem. 2007, 101, 345-350.
49. Bicas, J.L.; de Quadros, C.P.; Neri-Numa, I.A.; Pastore, G.M. Integrated process for co-production of alkaline lipase and R-(+)-α-terpineol by Fusarium oxysporum. Food Chem. 2010, 120, 452-456.
50. Grogan, G.J.; Holland, H.L. The biocatalytic reactions of Beauveria spp. J. Mol. Catal. B: Enzym. 2000, 9, 1-32.
51. Buchanan, G.O.; Williams, L.A.D.; Reese, P.B. Biotransformation of cadinane sesquiterpenes by Beauveria bassiana ATCC 7159. Phytochemistry 2000, 54, 39-45.
52. Buchanan, G.O.; Reese, P.B. Biotransformation of diterpenes and diterpene derivatives by Beauveria bassiana ATCC 7159. Phytochemistry 2001, 56, 141-151.
53. Qiao, L.; Xie, D.; Liu, Q.; Zou, J.; Shen, Z.; Dai, J. Microbial transformation of lovastatin by Beauveria bassiana. Acta Pharm. Sinica B 2012, 2, 300-305.
54. Aleu, J.; Collado, I.C. Biotransformations by Botrytis species. J. Mol. Catal. B: Enzym. 2001, 13, 77-93.
55. Daoubi, M.; Duran-Patron, R.; Hernandez-Galan, R.; Benharref, A.; James, R.; Hanson J.R.; Collado, I.C. The role of botrydienediol in the biodegradation of the sesquiterpenoid phytotoxin botrydial by Botrytis cinerea. Tetrahedron 2006, 62, 8256-8261.
56. Bustillo, A.J.; Aleu, J.; Hernández-Galán, R.; Collado, I.C. Biotransformation of the fungistatic compound (R)-(+)-1-(4'-chlorophenyl) propan-1-ol by Botrytis cinerea. J. Mol. Catal. B: Enzym. 2003, 21, 267-271.
57. Paruch, E.; Ciunik, Z.; Nawrot, J.; Wawrzeńczyk, C. Lactones 9. Synthesis of terpenoid lactones-active insect antifeedants. J. Agric. Food Chem. 2000, 48, 4973-4977.
58. Paruch, E.; Nawrot, J.; Wawrzeńczyk, C. Lactones 11. Feeding-deterrent activity of some bi- and tricyclic terpenoid lactones. Pest Manag. Sci. 2001, 57, 776-780.
59. Gabryś, B.; Szczepanik, M.; Dancewicz, K.; Szumny, A.; Wawrzeńczyk, C. Environmentally Safe Insect Control: Feeding Deterrent Activity of Alkyl-Substituted γ- and δ-Lactones to Peach Potato Aphid (Myzus persicae [Sulz.]) and Colorado Potato Beetle (Leptinotarsa decemlineata Say). Polish J. Environ. Stud. 2006, 15, 549-556.
60. Wawrzeńczyk, C.; Grabarczyk, M.; Szumny, A.; Gabryś, B.; Dancewicz, K.; Nawrot, J.; Pradzyńska, A.; Halarewicz-Pacan, A. Lactones19. Synthesis and antifeedant activity of lactones with methyl-, dimethyl- and trimethylcyclohexane system. In Chemistry for Agriculture; Górecki, H., Dobrzański, Z., Kafarski, P., Eds.; Czech-Pol Trade: Wrocław, Poland, 2003; pp. 117-129.
61. Szczepanik, M.; Grabarczyk, M.; Szumny, A.; Wawrzeńczyk, C. Feeding detergent activity of lactones with di- and trimethylcyclohexane system against lesser mealworm, Alphitobius diaperinus Panzer and Colorado potato beetle (Leptinotarsa decemlineata Say). J. Plant Prot. Res. 2003, 43, 87-96.
62. Dancewicz, K.; Gabryś, B.; Halarewicz-Pacan, A.; Grabarczyk, M.; Wawrzeńczyk, C. Effect of terpenoid lactones with di- and trimethylcyclohexane systems on the behaviour of green peach aphid Myzus persicae. Pesticydy (Pesticides) 2005, 4, 17-23.
63. Grabarczyk, M.; Szumny, A.; Gładkowski, W.; Białoń ska, A.; Ciunik, Z.; Wawrzeńczyk, C. Lactones 18. Synthesis of bicyclic lactones with methyl-, di- and trimethyl substituted cyclohexane system. Pol. J. Chem. 2005, 79, 1763-1771.