Identification of syn- and anti-Anethole-2,3-epoxides in the Metabolism of trans-Anethole by the Newly Isolated Bacterium Pseudomonas putida JYR-1

Journal of Agricultural and Food Chemistry

Volumn 53, Issue 15, 2005, Pages 5954-5958

  Ryu, Jiyoung ^a   Seo, Jiyoung ^a   Lee, Youngshim ^b   Lim, Yoongho ^b   Ahn, Joong Hoon ^b   Hur, Hor Gil ^a  

^a Gwangju Institute of Science and Technology (GIST)   (South Korea)

^b Konkuk University   (South Korea)

Author keywords

Biotransformation; Flavor; Phenylpropanoid; Pseudomonas; trans Anethole

Indexed keywords

ANETHOLE; ANISOLE DERIVATIVE; BACTERIAL DNA; EPOXIDE; RNA 16S;

ARTICLE; CHEMISTRY; CLASSIFICATION; GENETICS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; KINETICS; METABOLISM; MICROBIOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PSEUDOMONAS PUTIDA;

ANISOLES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; DNA, BACTERIAL; EPOXY COMPOUNDS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; PSEUDOMONAS PUTIDA; RNA, RIBOSOMAL, 16S; SOIL MICROBIOLOGY;

PSEUDOMONAS; PSEUDOMONAS PUTIDA;

EID: 23744448646     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf040445x     Document Type: Article

References (28)

1. Heldt, H.-W. Plant Biochenmistry and Molecular Biology; Oxford University Press: New York, 1999.
2. Nugroho, L. H.; Verberne, M. C.; Verpoorte, R. Activities of enzymes involved in the phenylpropanoid pathway in constitutively salicylic acid-producing tobacco plants. Plant Physiol. Biochem. 2002, 40, 755-760.
3. Krings, U.; Berger, R. G. Biotechnological production of flavours and fragrances. Appl. Microbiol. Biotechnol. 1998, 49, 1-8.
4. Priefert, H.; Rabenhorst, J.; Steinbuchel, A. Biotechnological production of vanillin. Appl. Microbiol. Biotechnol. 2001, 56, 296-314.
5. Shimoni, E.; Ravid, U.; Shoham, Y. Isolation of a Bacillus sp. capable of transforming isoeugenol to vanillin. J. Biotechnol. 2000, 78, 1-9.
6. Shimoni, E.; Baasov, T.; Ravid, U.; Shoham, Y. The trans-anethole degradation pathway in an Arthrobacter sp. J. Biol. Chem. 2002, 277, 11866-11872.
7. Shimoni, E.; Baasov, T.; Ravid, U.; Shoham, Y. Biotransformations of propenylbenzenes by an Arthrobacter sp. and its t-anethole blocked mutants. J. Biotechnol. 2003, 105, 61-70.
8. Tripathi, U.; Rao, R. S.; Ravishankar, G. A. Biotransformation of phenylpropanoid compounds to vanilla flavor metabolites in cultures of Haematococcus pluvialis. Process Biochem. 2002, 38, 419-426.
9. Tadasa, K. Degradation of eugenol by a microorganism. Agric. Biol. Chem. 1977, 41, 925-929.
10. Tadasa, K.; Kayahara, H. Initial steps of eugenol degradation pathway of a microorganism. Agric. Biol. Chem. 1983, 47, 2639-2640.
11. Newberne, P.; Smith, R. L.; Doull, J.; Goodman, J. I.; Munro, I. C.; Portoghese, P. S.; Wagner, B. M.; Weil, C. S.; Woods, L. A.; Adams, T. B.; Lucas, C. D.; Ford, R. A. The FEMA GRAS assessment of trans-anethole used as a flavouring substance. Food Chem. Toxicol. 1999, 37, 789-811.
12. Passreiter, C. M.; Wilson, J.; Andersen, R.; Isman, M. B. Metabolism of thymol and trans-anethole in larvae of Spodoptera litura and Trichoplusia ni (Lepidoptera: Noctuidae). J. Agric. Food Chem. 2004, 52, 2549-2551.
13. Stanier, R. Y.; Palleroni, N. J.; Duodoroff, M. The aerobic pseudomonads: a taxonomic study. J. Gen. Microbiol. 1966, 43, 159-271.
14. Pitcher, D. G.; Saunder, N. A.; Owen, R. J. Rapid extraction of bacterial genomic DNA with guanidium thiocyanate. Lett. Appl. Microbiol. 1989, 8, 151-156.
15. Chun, J.; Goodfellow, M. A phylogenetic analysis of the genus Nocardia with 16S rRNA gene sequences. Int. J. Syst. Bacteriol. 1995, 45, 240-245.
16. Saitou, N.; Nei, M. The neighbor-joining method: a new method for reconstructing phylogenetic trees. Mol. Biol. Evol. 1987, 4, 406-425.
17. Yang, H.; Kang, K. R.; Lim, Y. Spectral assignments and reference data. Magn. Reson. Chem. 2003, 41, 223-226.
18. Pretsch, E.; Buehlmann, P.; Affolter, C. Structure Determination of Organic Compounds: Tables of Spectral Data, 3rd ed.; Springer: Tokyo, Japan, 2000; 421 pp.
19. Miller, V. P.; DePillis, G. D.; Ferrer, J. C.; Mauk, A. G.; Ortiz de Montellano, P. R. Monooxygenase activity of cytochrome C peroxidase. J. Biol. Chem. 1992, 267, 8936-8942.
20. Keener, W. K.; Arp, D. J. Transformations of aromatic compounds by Nitrosomonas europaea. Appl. Environ. Microbiol. 1994, 60, 1914-1920.
21. Colby, J.; Stirling, D. I.; Dalton, H. The soluble methane monooxygenase of Methylococcus capsulatus (Bath): its ability to oxygenate n-alkanes, n-alkenes, ethers, and alicyclic, aromatic and heterocyclic compounds. Biochem. J. 1977, 165, 395-402.
22. Burrows, K. J.; Cornish, A.; Scott, D.; Higgins, I. J. Substrate specificites of the soluble and particulate methane monooxygenases of Methylosinus trichosporium OB3b. J. Gen. Microbiol. 1984, 130, 3327-3333.
23. Marconi, A. M.; Beltrametti, F.; Bestetti, G.; Solinas, F.; Ruzzi, M.; Galli, E.; Zennaro, E. Cloning and characterization of styrene catabolism genes from Pseudomonas fluorescens ST. Appl. Environ. Microbiol. 1996, 62, 121-127.
24. Colonna, S.; Gaggero, N.; Casella, L.; Carrea, G.; Pasta, P. Enantioselective epoxidation of styrene derivatives by chloroperoxidase catalysis. Tetrahedron Asymmetry 1993, 4, 1325-1330.
25. terp (CYP108). J. Biol. Chem. 1994, 269, 28815-28821.
26. Watabe, T.; Ozawa, N.; Yoshikawa, K. Stereochemistry in the oxidative metabolism of styrene by hepatic microsomes. Biochem. Pharmacol. 1981, 30, 1695-1698.
27. Zolezzi, S.; Spodine, E.; Decinti, A. Epoxidation of styrene with iodosylbenzene in the presence of copper(II) Schiff-base complexes. Polyhedron 2003, 22, 1653-1658.
28. Patil, N. S.; Uphade, B. S.; Jana, P.; Bharagava, S. K.; Choudhary, V. R. Epoxidation of styrene by anhydrous tert-butyl hydroperoxide over reusable gold supported on MgO and other alkaline earth oxides. J. Catal. 2004, 223, 236-239.