Abstract
Two oxygen-containing monoterpene substrates, menthol or geraniol (25 mg l−1), were added to Anethum graveolens hairy root cultures to evaluate the influence of the biotransformation capacity on growth and production of volatile compounds. Growth was assessed by the dissimilation method and by fresh and dry weight measurement. The volatiles were analyzed by GC and GC–MS. The total constitutive volatile component was composed, in more than 50%, by falcarinol (17–52%), apiole (11–24%), palmitic acid (7–16%), linoleic acid (4–9%), myristicin (4-8%) and n-octanal (2-5%). Substrate addition had no negative influence on growth. The relative amount of menthol quickly decreased 48 h after addition, and the biotransformation product menthyl acetate was concomitantly formed. Likewise, the added geraniol quickly decreased over 48 h alongside with the production of the biotransformation products. The added geraniol was biotransformed in 10 new products, the alcohols linalool, α-terpineol and citronellol, the aldehydes neral and geranial, the esters citronellyl, neryl and geranyl acetates and linalool and nerol oxides.
Similar content being viewed by others
References
Costa MM, Figueiredo AC, Barroso JG, Pedro LG, Deans SG, Scheffer JJC (2008) Nitrogen stress induction on Levisticum officinale hairy roots grown in darkness and under photoperiod conditions: effect on growth and volatile components. Biotechnol Lett 30:1265–1270
Croteau R (1980) The biosynthesis of terpene compounds. In: Croteau R (ed) Fragrance and flavor substances. D&PS Verlag, Germany, pp 13–36
Everitt ZM, Lockwood GB (1995) Anethum graveolens L. (Dill). In vitro culture and metabolism of volatile constituents. In: Bajaj YPS (ed) Biotechnology in agriculture and forestry, vol 33, medicinal and aromatic plants III. Springer-Verlag, Berlin, pp 21–34
Figueiredo AC, Almendra MJ, Barroso JG, Scheffer JC (1996) Biotransformation of monoterpenes and sesquiterpenes by cell suspension cultures of Achillea millefolium L. ssp. millefolium. Biotechnol Lett 18:863–868
Iijima Y, Gang DR, Fridman E, Lewinsohn E, Pichersky E (2004) Characterization of geraniol synthase from the peltate glands of sweet basil. Plant Physiol 134:370–379
King A, Dickinson JR (2000) Biotransformation of monoterpene alcohols by Saccharomyces cerevisiae, Torulaspora delbrueckii and Kluyveromyces lactis. Yeast 16:499–506
Lange BM, Wildung MR, Stauber EJ, Sanchez C, Pouchnik D, Croteau R (2000) Probing essential oil biosynthesis and secretion by functional evaluation of expressed sequence tags from mint glandular trichomes. Proc Natl Acad Sci USA 97:2934–2939
Li W, Koike K, Asada Y, Yoshikawa T, Nikaido T (2003) Biotransformation of low molecular-weight alcohols by Coleus forskohlii hairy root cultures. Carbohyd Res 338:729–731
Likens ST, Nickerson GB (1964) Detection of certain Hop oil constituents in brewing products. Am Soc Brew Chem Proc 5:13–19
Luan F, Mosandl A, Münch A, Wüst M (2005) Metabolism of geraniol in grape berry mesocarp of Vitis vinifera L. cv. Scheurebe: demonstration of stereoselective reduction, E/Z-isomerization, oxidation and glycosylation. Phytochemistry 66:295–303
Martinkus C, Croteau R (1981) Metabolism of monoterpenes. Plant Physiol 68:99–106
Nunes IS, Faria JMS, Figueiredo AC, Pedro LG, Trindade H, Barroso JG (2009) Menthol and geraniol biotransformation and glycosylation capacity of Levisticum officinale hairy roots. Planta Medica (in press)
Santos PAG, Figueiredo AC, Lourenço PML, Barroso JG, Pedro LG, Oliveira MM, Schripsema J, Deans SG, Scheffer JJC (2002) Hairy root cultures of Anethum graveolens (dill): establishment, growth, time-course study of their essential oil and its comparison with parent plant oils. Biotechnol Lett 24:1031–1036
Schenk UR, Hildebrandt AC (1972) Medium and techniques for induction and growth of monocotyledonous and dicotyledonous plant cell cultures. Can J Bot 50:199–204
Seigler DS (1998) Plant secondary metabolism. Kluwer Academic Publishers, Massachussets, EUA
Srivastava S, Srivastava AK (2007) Hairy root culture for mass-production of high-value secondary metabolites. Crit Rev Biotechnol 27:29–43
Zheng G, Lu W, Aisa HA, Cai J (1999) Absolute configuration of falcarinol, a potent antitumor agent commonly occurring in plants. Tetrahedron Lett 40:2181–2182
Author information
Authors and Affiliations
Corresponding author
Electronic supplementary material
Below is the link to the electronic supplementary material.
Rights and permissions
About this article
Cite this article
Faria, J.M.S., Nunes, I.S., Figueiredo, A.C. et al. Biotransformation of menthol and geraniol by hairy root cultures of Anethum graveolens: effect on growth and volatile components. Biotechnol Lett 31, 897–903 (2009). https://doi.org/10.1007/s10529-009-9934-3
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10529-009-9934-3