Formation of trans-verbenol and verbenone from α-pinene catalysed by immobilised Picea abies cells

Bioscience, Biotechnology and Biochemistry

Volumn 69, Issue 2, 2005, Pages 321-325

  Vaněk, Tomáš ^a   Halík, Jan ^a   Vaňková, Radmila ^b   Valterová, Irena ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY   (Czech Republic)

^b INSTITUTE OF EXPERIMENTAL BOTANY   (Czech Republic)

Author keywords

Alginate; Allylic oxidation; Biotransformation; Monoterpene; Plant cell

Indexed keywords

CELLS; MOLECULAR ORIENTATION; STEREOCHEMISTRY; SUBSTRATES;

ENANTIOMERS; FREE CELLS; VERBENONES;

CATALYSIS;

ALPHA-PINENE; PINENE; TERPENE; VERBENOL; VERBENONE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; CYTOLOGY; IMMOBILIZED CELL; METABOLISM; SPRUCE; STEREOISOMERISM; TIME;

CELLS, IMMOBILIZED; MOLECULAR STRUCTURE; MONOTERPENES; PICEA; STEREOISOMERISM; TERPENES; TIME FACTORS;

ABIES; PICEA ABIES;

EID: 15744375394     PISSN: 09168451     EISSN: None     Source Type: Journal    
DOI: 10.1271/bbb.69.321     Document Type: Article

References (21)

1. Cheetham, P. S. J., The use of biotransformations for the production of flavors and fragrances. Trends Biotechnol., 11, 478-488 (1993).
2. Hagedorn, S., and Kaphammer, B., Microbial biocatalysis in the generation of favor and fragrance chemicals. Annu. Rev. Microbiol., 48, 773-800 (1994).
3. Lindmark-Henriksson, M., Isaksson, D., Sjödin, K., Högberg, H.-E., Vaněk, T., and Valterová, I., Transformation of α-pinene using a Picea abies suspension culture. J. Nat. Prod., 66, 337-343 (2003).
4. Trelles, J. A., Bentancor, L., Schoijet, A., Porro, S., Lewkowicz, E. S., Sinisterra, J. V., and Iribarren, A. M., Immobilized Escherichia coli BL21 as a catalyst for the synthesis of adenine and hypoxanthine nucleosides. Chemistry & Biodiversity, 1, 280-288 (2004).
5. Bhattacharyya, P. K., Prema, B. R., Kulkarni, B. D., and Pradhan, S. K., Microbiological transformation of terpenes: Hydroxylation of α-pinene. Nature, 187, 689-690 (1960).
6. Rama Devi, J., and Bhattacharyya, P. K., Molecular rearrangements in the microbiological transformations of terpenes and the chemical logic of microbial processes. J. Indian Chem. Soc., 55, 1131-1137 (1978).
7. Draczyńska, B., Cagara, Cz., Siewiński, A., Rymkiewicz, A., Zabza, A., and Leufvèn, A., Biotransformation of pinenes; XVII. Transformation of α- and β-pinenes by means of Armillariella mellea (honey fungus), a parasite of woodlands. J. Basic Microbiol., 25, 487-492 (1985).
8. Wright, S. J., Caunt, P., Carter D., and Baker, P. B., Microbial oxidation of α-pinene by Serratia marcescens. Appl. Microbiol. Biotechnol., 23, 224-227 (1986).
9. Busmann, D., and Berger, R. G., Bioconversion of terpenoid hydrocarbons by basidiomycetes. In "Trends in Flavour Research", eds. Maarse, H., and van der Heij, D. G., Elsevier Science Publishers B. V., Amsterdam, pp. 503-507 (1994).
10. Hagedorn, S., and Kaphammer, B., Microbial biocatalysis in the generation of flavor and fragrance chemicals. Annu. Rev. Microbiol., 48, 773-800 (1994).
11. Agrawal, R., Deepika, N.-U.-A., and Joseph, R., Strain improvement of Aspergillus sp. and Penicillium sp. by induced mutation for biotransformation of α-pinene to verbenol. Biotechnol. Bioeng., 63, 249-252 (1999).
12. th International Congress of Essential Oils, Fragrances and Flavors, 16-20 November, Washington, DC, U.S.A., eds. Lawrence, R. M., Mookherjee, B. D., and Willis, B. J., Elsevier Science Publishers B. V., Amsterdam, pp. 731-741 (1986).
13. Hirata, T., Ikeda, Y., Izumi, S., Shimoda, K., Hamada, H., and Kawamura, T., Introduction of oxygenated functional groups into 3-carene and 2-pinene by cultured cells. Phytochemistry, 37, 401-403 (1994).
14. Leufvén, A., Bergström, G., and Falsen, E., Oxygenated monoterpenes produced by yeasts, isolated from Ips typographus (Coleoptera: Scolytidae) and grown in phloem medium. J. Chem. Ecol., 14, 353-361 (1988).
15. Vité, J. P., Bakke, A., and Renwick, J. A. A., Pheromones in Ips (Coleoptera: Scolytidae): Occurrence and production. Can. Entomol., 104, 1967-1975 (1972).
16. Ascolichristensen, A., Salom, S. M., and Payne, T. L., Olfactory receptor cell responses of Ips grandicollis (EICHHOFF) (Coleoptera, Scolytidae) to intraspecific and interspecific behavioral chemicals. J. Chem. Ecol., 19, 699-712 (1993).
17. Grosman, D. M., Salom, S. M., Ravlin, F. W., and Young, R. W., Geographic and gender differences in semiochemicals in emerging adult southern pine beetle (Coleoptera: Scolytidae). Ann. Entomol. Soc. Am., 90, 438-446 (1997).
18. Schlyter, F., Birgersson, G., and Leufven, A., Inhibition of attraction to aggregation pheromone by verbenone and ipsenol - density regulation mechanisms in bark beetle Ips typographus. J. Chem. Ecol., 15, 2263-2277 (1989).
19. Jakus, R., Schlyter, F., Zhang, Q. H., Blazenec, M., Vavercak, R., Grodzki, W., Brutovsky, D., Lajzova, E., Turcani, M., Bengtsson, M., Blum, Z., and Gregoire, J. C., Overview of development of an anti-attractant based technology for spruce protection against Ips typographus: From past failures to future success. Anz. Schadlingsk.-J. Pest Sci., 76, 89-99 (2003).
20. Bovara, R., Carrea, G., Ferrara, L., and Riva, S., Resolution of (±)-trans-sobrerol by lipase PS-catalyzed transesterification and effects of organic solvents on enantioselectivity. Tetrahedron: Asymmetry, 2, 931-938 (1991).
21. Lindmark-Hendriksson, M., Isaksson, D., Vaněk, T., Valterová, I., Högberg, H.-E., and Sjödin, K., Transformation of terpenes using a Picea abies suspension culture. J. Biotechnol., 107, 173-184 (2004).