Co-production of caffeic acid and p-hydroxybenzoic acid from p-coumaric acid by Streptomyces caeruleus MTCC 6638

Applied Microbiology and Biotechnology

Volumn 71, Issue 5, 2006, Pages 720-727

  Sachan, Ashish ^a   Ghosh, Shashwati ^a   Sen, Sukanta Kumar ^b   Mitra, Adinpunya ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY   (India)

^b VISVA BHARATI UNIVERSITY   (India)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; CELLS; HYDROXYLATION; IONIZATION; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; NUTRITION;

CAFFEIC ACID; ELECTROSPRAY IONIZATION MASS SPECTROMETRY; P-COUMARIC ACID; P-HYDROXYBENZOIC ACID;

CARBOXYLIC ACIDS;

4 HYDROXYBENZOIC ACID; CAFFEIC ACID; CARBON; COUMARIC ACID; GLUCOSE; HYDROXYBENZOIC ACID; PARA COUMARIC ACID; PHENOL DERIVATIVE;

BACTERIUM; INCUBATION; PHENOLIC COMPOUND;

ARTICLE; BACTERIUM CULTURE; BIOTRANSFORMATION; CONCENTRATION (PARAMETERS); ELECTROSPRAY MASS SPECTROMETRY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NONHUMAN; STREPTOMYCES; STREPTOMYCES CAERULEUS;

CAFFEIC ACIDS; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; COUMARIC ACIDS; CULTURE MEDIA; MASS SPECTROMETRY; PARABENS; STREPTOMYCES;

STREPTOMYCES CAERULEUS;

EID: 33746335662     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-005-0197-1     Document Type: Article

References (38)

1. Abd El-Mawla AMA, Beerhues L (2002) Benzoic acid biosynthesis in cell cultures of Hypericum androsaemum. Planta 214:727-733
2. Barghini P, Montebove F, Ruzzi M, Schiesser A (1998) Optimal conditions for bioconversion of ferulic acid into vanillic acid by Pseudomonas fluorescens BF13 cells. Appl Microbiol Biotechnol 49:309-314
3. Bode HB, Müller R (2003) Possibility of bacterial recruitment of plant genes associated with the biosynthesis of secondary metabolites. Plant Physiol 132:1153-1161
4. Bradford MM (1976) A rapid and sensitive method for the quantitation of microgram quantities of protein utilizing the principle of protein-dye binding. Anal Biochem 72:248-254
5. Brunati M, Marinelli F, Bertolini C, Gandolfi R, Daffonchio D, Molinari F (2004) Biotransformation of cinnamic and ferulic acid with actinomycetes. Enzyme Microb Technol 34:3-9
6. Dey G, Sachan A, Ghosh S, Mitra A (2003) Detection of major phenolic acids from dried mesocarpic husk of mature coconut by thin layer chromatography. Ind Crops Prod 18:171-176
7. Dixon RA, Paiva NL (1995) Stress-induced phenylpropanoid metabolism. Plant Cell 7:1085-1097
8. Douglas CJ (1996) Phenylpropanoid metabolism and lignin biosynthesis: from weeds to trees. Trends Plant Sci 1:171-178
9. Estrada Alvarado I, Lomascolo A, Navarro D, Delattre M, Asther M, Lesage-Meessen L (2001) Evidence of a new biotransformation pathway of p-coumaric acid into p-hydroxybenzaldehyde in Pycnoporus cinnabarinus. Appl Microbiol Biotechnol 57:725-730
10. Estrada Alvarado I, Navarro D, Record E, Asther M, Asther M, Lesage-Meessen L (2003) Fungal biotransformation of p-coumaric acid into caffeic acid by Pycnoporus cinnabarinus: an alternative for producing a strong natural antioxidant. World J Microbiol Biotechnol 19:157-160
11. Ghosh S, Sachan A, Mitra A (2005) Degradation of ferulic acid by a white-rot fungus Schizophyllum commune. World J Microbiol Biotechnol 21:385-388
12. Hartley RD, Harris PJ (1981) Phenolic constituents of the cell walls of dicotyledons. Biochem Syst Ecol 9:189-203
13. Hartmann T, Kutchan TM, Strack D (2005) Evolution of metabolic diversity. Phytochemistry 66:1198-1199
14. Henderson MEK (1961) The metabolism of aromatic compounds related to lignin by some hyphomycetes and yeast-like fungi of soil. J Gen Microbiol 26:155-165
15. Hertweck C, Moore BS (2000) A plant-like biosynthesis of benzoyl CoA in the marine bacterium 'Streptomyces maritimus'. Tetrahedron 56:9115-9120
16. Hertweck C, Jarvis AP, Xiang L, Moore BS, Oldham NJ (2001) A mechanism of benzoic acid biosynthesis in plants and bacteria that mirrors fatty acid β-oxidation. Chembiochem 10:784-786
17. Löscher R, Heide L (1994) Biosynthesis of p-hydroxybenzoate from p-coumaric acid and p-coumaryl-coenzyme a in cell-free extracts of Lithospermum erythrorhizon cell cultures. Plant Physiol 106:271-279
18. MacAdam JW, Grabber JH (2002) Relationship of growth cessation with the formation of diferulic acid cross-links and p-coumaroylated lignins in tall fescue leaf blades. Planta 215: 783-793
19. McQualter RB, Chong BF, Meyer K, Van Dyk DE, O'Shea MG, Walton NJ, Viitanen PV, Brumbley SM (2005) Initial evaluation of sugarcane as a production platform for p-hydroxybenzoic acid. Plant Biotechnol J 3:29-41
20. Michaluart P, Masferrer JL, Carothers AM, Subbaramaiah K, Zweifel BS, Koboldt C, Mestre JR, Grunberger D, Sacks PG, Tanabe T, Dannenberg AJ (1999) Inhibitory effect of caffeic acid phenethyl ester on the activity and expression of cyclooxygenase-2 in human oral epithelial cell and in rat model of inflammation. Cancer Res 59:2347-2352
21. Mitra A, Kitamura YJ, Gasson MJ, Narbad A, Parr A, Payne J, Rhodes MJC, Sewter C, Walton NJ (1999) 4-Hydroxycinnamoyl-CoA-hydratase/lyase (HCHL) - an enzyme of phenylpropanoid chain cleavage from Pseudomonas. Arch Biochem Biophys 365:10-16
22. Muheim A, Lerch K (1999) Towards a high-yield bioconversion of ferulic acid to vanillin. Appl Microbiol Biotechnol 51:456-461
23. Nambudiri AMD, Subba Rao PV, Bhat JV (1969) Metabolism of p-coumaric acid by Streptomyces - formation of caffeic acid as intermediate. Curr Sci 38:402
24. Nambudiri AMD, Bhat JV, Subba Rao PV (1972) Conversion of p-coumaric acid into caffeic acid by Streptomyces nigrifaciens: purification and properties of the hydroxylating enzyme. Biochem J 130:425-433
25. Nardini M, D'Aquino M, Tomassi G, Gentili V, Felice MD, Scaccini C (1995) Inhibition of human low-density lipoprotein oxidation by caffeic acid and other hydroxycinnamic acid derivatives. Free Radic Biol Med 19:541-552
26. Nielsen KM, Bones AM, Smalla K, van Elsas JD (1998) Horizontal gene transfer from transgenic plants to terrestrial bacteria - a rare event. FEMS Microbiol Rev 22:79-103
27. Podstolski A, Havkin-Frenkel D, Malinowski J, Blount JW, Kourteva G, Dixon RA (2002) Unusual 4-hydroxybenzalde-hyde synthase activity from tissue cultures of the vanilla orchid Vanilla planifolia. Phytochemistry 61:611-620
28. Rosazza JPN, Huang Z, Dostal L, Volm T, Rousseau B (1995) Biocatalytic transformations of ferulic acid: an abundant aromatic natural product. J Ind Microbiol 15:457-471
29. Sachan A, Ghosh S, Mitra A (2004) An efficient isocratic separation of hydroxycinnamic acids and their corresponding benzoates from microbial and plant sources by HPLC. Biotechnol Appl Biochem 40:197-200
30. Sachan A, Ghosh S, Mitra A (2005) Biotransformation of p-coumaric acid by Paecilomyces variotii. Lett Appl Microbiol (in press)
31. Sato M (1966) Metabolism of phenolic substances by the chloroplasts II. conversion by the isolated chloroplasts of p-coumaric acid to caffeic acid. Phytochemistry 5:385-389
32. Schnitzler J, Madlung J, Rose A, Seitz HU (1992) Biosynthesis of p-hydroxybenzoic acid in elicitor-treated carrot cell cultures. Planta 188:594-600
33. Shirling EB, Gottlieb D (1966) Methods of characterization of Streptomyces. Int J Syst Bacteriol 61:313-340
34. Sutherland JB, Crawford DJ, Pometto AL III (1983) Metabolism of cinnamic, p-coumaric and ferulic acids by Streptomyces setonii. Can J Microbiol 29:1253-1257
35. Tomas-Barberan FA, Clifford MN (2000) Dietary hydroxybenzoic acid derivatives - nature, occurrence and dietary burden. J Sci Food Agric 80:1024-1032
36. Walton NJ, Mayer MJ, Narbad A (2003) Vanillin. Phytochemistry 63:505-515
37. Wu R-Y, Chen M-H (1995) Identification of Streptomyces strain KS3-5. Bot Bull Acad Sin 36:201-205
38. Xiang LK, Moore BS (2002) Inactivation, complementation and heterologous expression of encP, a novel bacterial phenyalanine ammonia-lyase gene. J Biol Chem 277:32505-32509