Bioconversion of (+)- and (-)-alpha-pinene to (+)- and (-)-verbenone by plant cell cultures of Psychotria brachyceras and Rauvolfia sellowii

Electronic Journal of Biotechnology

Volumn 10, Issue 4, 2007, Pages 500-507

  Limberger, Renata Pereira ^a   Aleixo, Adriana Mendes ^b   Fett Neto, Arthur Germano ^c   Henriques, Amélia T ^a  

^a FEDERAL UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b METHODIST UNIVERSITY OF PIRACICABA   (Brazil)

^c Centro de Biotecnologia   (Brazil)

Author keywords

Alpha pinene; Biotransformation; Verbenol; Verbenone

Indexed keywords

AMINES; BIOCONVERSION; BIOTECHNOLOGY; ENANTIOMERS; GAS CHROMATOGRAPHY; PLANT CELL CULTURE;

ALPHA-PINENE; BIOTRANSFORMATION; VERBENOL; VERBENONE;

ORGANIC COMPOUNDS;

PINENE; VERBENONE;

APOCYNACEAE; ARTICLE; AUTOOXIDATION; BIOCATALYST; BIOTRANSFORMATION; CELL CULTURE; CONTROLLED STUDY; ENANTIOMER; GAS CHROMATOGRAPHY; INCUBATION TIME; MASS SPECTROMETRY; NONHUMAN; PLANT CELL; PSYCHOTRIA; PSYCHOTRIA BRACHYCERAS; RAUVOLFIA SELLOWII;

PSYCHOTRIA; RAUVOLFIA SELLOWII;

EID: 37849043958     PISSN: None     EISSN: 07173458     Source Type: Journal    
DOI: 10.2225/vol10-issue4-fulltext-8     Document Type: Article

References (20)

1. ADAMS, Robert P. Identification of essential oil components by gas chromatography/quadrupole mass spectrometry. Carol Stream, Allured Publishing Corp., 2001, 456 p. ISBN 0-931710-85-5.
2. AGRAWAL, Renu and JOSEPH, Richard. Bioconversion of alpha-pinene to verbenone by resting cells of Aspergillus niger. Applied Microbiology and Biotechnology, March 2000, vol. 53, no. 3, p. 335-337.
3. DIAZ-NUÑEZ, Vicente; SANCHEZ-MARTINEZ, Guillermo and GILLETTE, Nancy E. Response of Dendroctonus mexicanus (Hopkins) to two optical isomers of verbenone. Agrociencia, May 2006, vol. 40, no. 3, p. 349-354.
4. DIVYASHREE, M.S.; GEORGE, J. and AGRAWAL, R. Biotransformation of terpenic substrates by resting cells of Aspergillus niger and Pseudomonas putida isolates. Journal of Food Science and Technology, January 2006, vol. 43, no. 1, p. 73-76.
5. FAROOQ, Afgan; TAHARA, Satoshi; CHOUDHARY, M. Iqbal; ATTA-UR-RAHMAN; AHMED, Zafar; BASER, K. Hüsnü Can and DEMIRCI, Fatih. Biotransformation of (-)-alpha-pinene by Botrytis cinerea. Zeitschrift für Naturforschung C, January 2002, vol. 57c, no. 3-4, p. 303-306.
6. GREGIANINI, Tatiana S.; SILVEIRA, Vivian C. da; PORTO, Diogo D.; KERBER, Vitor A.; HENRIQUES, Amélia T. and FETT-NETO, Arthur G. The alkaloid brachycerine is induced by ultraviolet radiation and is a singlet oxygen quencher. Photochemistry and Photobiology, November 2003, vol. 78, no. 5, p. 470-474.
7. HIRATA, Toshifumi; IKEDA, Yoshihiro; IZUMI, Shunsuke; SHIMODA, Kei; HAMADA, Hiroki and KAWAMURA, Toshinari. Introduction of oxigenated functional groups into 3-carene and 2-pinene by cultured cells. Phytochemistry, September 1994, vol. 37, no. 2, p. 401-403.
8. HUBER, D.P.W. and BORDEN, J.H. Protection of lodgepole pines from mass attack by mountain pine beetle, Dendroctonus ponderosae, with nonhost angiosperm volatiles and verbenone. Entomologia Experimentalis et Applicata, May 2001, vol. 99, no. 2, p. 131-141.
9. LAJUNEN, Marja K.; MAUNULA, Tatja and KOSKINEN, Ari M.P. Co(II) catalyzed oxidation of alpha-pinene by molecular oxygen. Part 2. Tetrahedron, October 2000, vol. 56, no. 41, p. 8167-8171.
10. LINDGREN, B. Staffan and MILLER, Daniel R. Effect of verbenone on five species of Bark Beetles (Coleoptera: Scolytidae) in Lodgepole Pine Forests. Environmental Entomology, October 2002, vol. 31, no. 5, p. 759-765.
11. LINDMARK-HENRIKSSON, Marica; ISAKSSON, Dan; SJÖDIN, Kristina; HÖGBERG, Hans-Erik; VANEK, Tomáš and VALTEROVÁ, Irena. Transformation of α-pinene using Picea abies suspension culture. Journal of Natural Products, February 2003, vol. 66, no. 3, p. 337-343.
12. MOGLIONI, Albertina G.; BROUSSE, Beatriz N.; ALVAREZ-LARENA, Angel; MOLTRASIO, Graciela Y. and ORTUÑO, Rosa M. Stereoselective synthesis of cyclobutyl GABA analogues and related compounds from (-)-(S)-verbenone. Tetrahedron: Asymmetry, April 2002, vol. 13, no. 5, p. 451-454.
13. PEREZ, Herminia I.; LUNA, Héctor; MANJARREZ, Norberto; SOLIS, Aida and NUÑEZ, Ma. Amelia. Preparation of (1S)-verbenone, aromatic and alicyclic carboxylic acids by oxidation of aldehydes, primary and secondary alcohols with Nocardia corallina. Biotechnology Letters, October 1999, vol. 21, no. 10, p. 855-858.
14. RAVID, Uzi; PUTIEVSKY, Eli; KATZIR, Irena; LEWINSOHN, Efraim and DUDAI, Nativ. Identification of (1R)(+)-verbenone in essential oils of Rosmarinus officinalis L. Flavour and Fragrance Journal, March 1997, vol. 12, no. 2, p. 109-112.
15. RECH, Sandra B.; BATISTA, Cezar V.F.; SCHRIPSEMA, Jan; VERPOORTE, Robert and HENRIQUES, Amelia T. Cell cultures of Rauvolfia sellowii: growth and alkaloid production. Plant Cell, Tissue and Organ Culture, July 1998, vol. 54, no. 1, p. 61-63.
16. ROUGE, Pablo D.; MOGLIONI, Albertina G.; MOLTRASIO, Graciela Y. and ORTUÑO, Rosa M. Stereoselective synthesis of chiral precursors to cyclobutane carbocyclic nucleosides and oligopeptides. Tetrahedron: Asymmetry, January 2003, vol. 14, no. 2, p. 193-195.
17. SCHENK, R.U. and HILDEBRANDT, A.C. Medium and Techniques for Induction and Growth of Monocotyledonous and Dicotyledonous Plant Cell Cultures. Canadian Journal Botanica, 1972, vol. 50, p. 199-204.
18. VAN DYK, M.S.; VAN RENSBURG, E. and MOLELEKI, N. Hydroxylation of (+)limonene, (-)-alpha-pinene and (-)-b-pinene by a Hormonema sp. Biotechnology Letters, April 1998, vol. 20, no. 4, p. 431-436.
19. VANEK, Tomáš; HALÍK, Jan; VANKOVÁ, Radmila and VALTEROVÁ, Irena. Formation of trans-verbenol and verbenone from alpha-pinene catalysed by immobilized Picea abies cells. Bioscience, Biotechnology, and Biochemistry, February 2005, vol. 69, no. 2, p. 321-325.
20. WRIGHT, Susan J.; CAUNT, Philip; CARTER, David and BAKER, Peter B. Microbial oxidation of alpha-pinene by Serratia marcescens. Applied Microbiology and Biotechnology, January 1986, vol. 23, no. 3-4, p. 224-227.