Planta Med 2011; 77 - PB29
DOI: 10.1055/s-0031-1282283

Biotransformation of cis-jasmone by fungal strains

AM Gliszczynska 1, M Górecka 1
  • 1Department of Chemistry, Wroclaw University of Environmental and Life Sciences, Wroclaw, Poland

Cis-jasmone, well known as a component of plant volatiles, is produced also by damaged plant vegetative tissues [1]. This natural ketone is considered to be the final product in the jasmonic acid biosynthetic pathway from linolenic acid [2]. This pale yellow, viscous liquid compound posses strong jasmine fragrance and interesting biological activities. It is an activator of chemical defence in plants, causing the release of volatile semiochemicals e.g. bean plants, Vicia faba, treated with cis-jasmone showed a significant increase in the production of (E)-ocimene [3]. Cis-jasmone is also responsible for plant-insect interactions. The population of grain aphid Sitobion avenae (Fabricius) is reduced by cis-jasmone which plays a role of repellent [4, 5] while members of two families of insect parasitoids (Braconidae and Sarcophagidae) in hop (Humulus lupulus L.) cultivation are attracted by cis-jasmone [6].

In our study we focused on the biotransformations of cis-jasmone by fungal cultures: Penicillium, Absidia, Syncephalastrum, Botrytis, Aspergillus, Cunninghamella, Chaetomium, Didymosphaeria. Screening procedure led to the selection of fifteen microorganisms that have ability to biotransformation of cis-jasmone. Microbial transformations were used as a tool to obtain new biologically active oxyderivatives. Major product of biotransformations was 4-hydroxyjasmone which was formed in regio- and stereoselective process of hydroxylation.

Fig.1

Acknowledgement: This Project was financed by European Union from the European Regional Development Found Grant No. POIG.01.03.01–00–158/09–03.

References: 1. Loughrin JH, Manukian A, Heath RR, Tumlinson JH (1995)J Chem Ecol 21:

1217–1227.

2. Koch T, Bandemer K, Boland W (1997) Helv Chim Acta 80: 838–850.

3. Birkett MA et al. (2000) Proceedings of the National Academy of Sciences USA 97:

9329–9334.

4. Bruce TJA, Martin LJ, Pickett JA, Pye BJ, Smart LE, Wadhams LJ (2003)

Pest Manag Sci 59: 1031–1036.

5. Bruce TJ, Pickett JA, Smart LE (2003) Pesticide Outlook 14: 96–98.

6. James G (2005)J Chem Ecol 31: 481–495.