Bioconversion of (+)-valencene in submerged cultures of the ascomycete Chaetomium globosum

Applied Microbiology and Biotechnology

Volumn 67, Issue 4, 2005, Pages 477-483

  Kaspera, Rüdiger ^a   Krings, Ulrich ^a   Nanzad, Tsevegsuren ^b   Berger, Ralf G ^a  

^a LEIBNIZ UNIVERSITY HANNOVER   (Germany)

^b NATIONAL UNIVERSITY OF MONGOLIA   (Mongolia)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; DETOXIFICATION; ENZYME INHIBITION; METABOLITES; OXIDATION; OXYGEN; PLANT CELL CULTURE;

ACTIVE TRANSPORT; NOOTKATOL; SESQUITERPENE; SUBMERGED CULTURES;

BIOCONVERSION;

ALPHA NOOTKATOL; CHEMICAL COMPOUND; NOOTKATONE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE; VALENCENE; VALENCENE 11,12 EPOXIDE;

FUNGUS;

ARTICLE; ASCOMYCETES; BIOTRANSFORMATION; CATALYSIS; CELL TRANSPORT; CELLULAR DISTRIBUTION; CHAETOMIUM GLOBOSUM; CONTROLLED STUDY; ENZYME ACTIVITY; FUNGAL CELL; FUNGUS CULTURE; NONHUMAN; OXIDATION; STEREOCHEMISTRY; SUBMERGED CELL CULTURE;

BIOTECHNOLOGY; CHAETOMIUM; CULTURE MEDIA; EPOXY COMPOUNDS; MAGNETIC RESONANCE SPECTROSCOPY; OXIDATION-REDUCTION; SESQUITERPENES;

CHAETOMIUM GLOBOSUM; FUNGI;

EID: 21344460013     PISSN: 01757598     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00253-004-1794-0     Document Type: Article

References (25)

1. Arantes S, Fraooq A, Hanson JR (1999) The preparation and microbial hydroxylation of the sesquiterpenoid nootkatone. J Chem Res Synop 248:801-812
2. Demyttenaere JCR (2001) Biotransformation of terpenoids by microorganisms. In: Atta-ur-Rhaman HEJ (ed) Studies in natural products chemistry, vol 25 (Bioactive natural products, part F), pp 125-178
3. Hashimoto T, Asakawa Y, Noma Y, Murakaki C, Tanaka M, Kanisawa T, Emura M (2003a) Nootkatone manufacture with Chlorella from valencene or hydroxyvalencene. Japanese Patent 2003070492
4. Hashimoto T, Asakawa Y, Noma Y, Murakaki C, Furusawa M, Kanisawa T, Emura M, Mitsuhashi K (2003b) Manufacture of nootkatone with Mucor sp. Japanese Patent 2003250591
5. Hill RA (1993) Terpenoids. In: Thomson RH (ed) Natural products. Blackie-Chapman & Hall, London, pp 106-139
6. Huang R, Christenson P, Labuda IM (2001) Production of natural flavours by laccase catalysis. European Patent 1083233
7. Isken S, de Boni JAM (1996) Active efflux of toluene in a solvent-resistant bacterium. J Bacteriol 178:6056-6058
8. Kaspera R (2004) Oxyfunktionalisierung von Terpenkohlenwasserstoffen zu aromaaktiven Terpenoiden durch selektive Biokatalyse. PhD thesis, University of Hannover, Germany
9. Kraker J-W de, Schurink M, Franssen MCR, König WA, de Groot A, Bouwmeester H (2003) Hydroxylation of sesquiterpenes by enzymes from chicory (Cichorium intybus L.) roots. Tetrahedron 59:409-418
10. Lewis DFV (1996) Cytochrome P450: structure, function and mechanism. Taylor & Francis, London
11. March J (1992) Advanced organic chemistry: reactions, mechanisms, and structure, 4th edn. Wiley, New York
12. Meylan WM, Howard PH (1995) Atom/fragment contribution method for estimating octanol-water partition coefficients. J Pharm Sci 84:83-92
13. Mitsuyoshi O (1994) New microorganism and preparation of nootkatone. Japanese Patent 6303967
14. Noma Y, Hashimoto T, Murakami C, Furusawa M, Asakawa Y (2001) Microbial transformation of valencene, nootkatol and nootkatone. In: Kuldo J, Wawrzenczyk C (eds) 32nd International symposium on essential oils, Agricultural University of Wroclaw, p 32
15. Onken J, Berger RG (1999) Effects of R-(+)-limonene on submerged cultures of the terpene transforming basidiomycete Pleurotus sapidus. J Biotechnol 69:163-168
16. Reil G, Berger RG (1996) Genesis of aroma compounds in phototrophic cell culture of grapefruit, C. paradisi cv. White Marsh. In: Mottram DS, Taylor AJ (eds) Proceedings of the 8th Weurman flavour symposium. Royal Society of Chemistry, Cambridge, pp 97-104
17. Schrader J, Berger RG (2001) Biotechnological production of terpenoid flavor and fragrance compounds. In: Rehm HJ (ed) Biotechnology, 2nd edn. Wiley-VCH, Weinheim, pp 374-422
18. Shoji N, Umeyama A, Asakawa Y, Takemoto T, Nomoto K, Ohizumi Y (1984) Structural determination of nootkatol, a new sesquiterpene isolated from Alpinia oxyphylla Miquel possessing calcium-antagonistic activity. J Pharm Sci 73:843-844
19. Sime JT (1998) The natural choice. Chem Br 34:26-28
20. Teunissen MJ, De Bont JAM (1995) Will terpenes be of any significance in future biotechnology? Colloq Inst Natl Rech Agron (Bioflavour 95) 75:329-337
21. Werf MJ van der, de Bont JAM, Leak DJ (1997) Opportunities in microbial biotransformation of monoterpenes. In: Scheper T (ed) Biotechnology of aroma compounds. Advances in biochemical engineering and biotechnology, vol 55. Springer, Berlin Heidelberg New York, pp 147-177
22. Werf MJ van der, Swarts HJ, de Bont JAM (1999) Rhodococcus erythropolis DCL14 contains a novel degradation pathway for limonene. Appl Environ Microbiol 65:2092-2102
23. Willershausen H, Graf H (1996) Mikrobieller Abbau von Lignin. CLB Chem Labor Biotechnol 47:24-28
24. Wüst M, Croteau RB (2002) Hydroxylation of specifically deuterated limonene enantiomers by cytochrome P450 limonene-6-hydroxylase reveals the mechanism of multiple product formation. Biochemistry 41:1820-1827
25. Ziegler FE, Reid GR, Studt WL, Wender PA (1977) Stereochemistry of dialkylcuprate additions to cyclopropyl acrylic esters. An application to the synthesis of (±)-eremophilone. J Org Chem 42:1991-2001