Sesquiterpenes of the geosmin-producing cyanobacterium Calothrix PCC 7507 and their toxicity to invertebrates

Zeitschrift fur Naturforschung - Section C Journal of Biosciences

Volumn 64, Issue 1-2, 2009, Pages 49-55

  Höckelmann, Claudia ^a   Becher, Paul G ^a,b   Von Reuß, Stephan H ^c   Jüttner, Friedrich ^a  

^a UNIVERSITY OF ZURICH   (Switzerland)

^b SWEDISH UNIVERSITY OF AGRICULTURAL SCIENCES   (Sweden)

^c UNIVERSITY OF HAMBURG   (Germany)

Author keywords

Cyanobacterium; Insecticide; Isodihydroagarofuran; Sesquiterpenes

Indexed keywords

CALOTHRIX; CALOTHRIX SP. PCC 7507; CHIRONOMIDAE; CHIRONOMUS RIPARIUS; CRUSTACEA; CYANOBACTERIA; INSECTA; INVERTEBRATA; NEMATODA; PLECTUS CIRRATUS; THAMNOCEPHALUS PLATYURUS;

EID: 62549139248     PISSN: 09395075     EISSN: None     Source Type: Journal    
DOI: 10.1515/znc-2009-1-209     Document Type: Article

References (30)

1. Adio A. M., Paul C., König W. A., and Muhle H. (2003), Volatile constituents in the liverwort Tritomaria polita. Phytochemistry 64, 637-644.
2. Ainge G. D., Gerard P. J., Hinkley S. F. R., Lorimer S. D., and Weavers R. T. (2001), Hodgsonox, a new class of sesquiterpene from the liverwort Lepidolaena hodgsoniae. Isolation directed by insecticidal activity. J. Org. Chem. 66, 2818-2821.
3. Beagley B., Pritchard R. G., Ramage R., and Southwell I. A. (1982), (+)-2-{(3R,6S,10R)-6,10-Dimethylbicyclo[4.4.0] dec-1-en-3-yl}-2-propanol, rosifoliol. Acta Crystallogr. B 38, 1391-1393.
4. Becher P. G., Keller S., Jung G., Süssmuth R. D., and Jüttner F. (2007), Insecticidal activity of 12-epi-hapalindole J isonitrile. Phytochemistry 68, 2493-2497.
5. Bruchet A. (1999), Solved and unsolved cases of taste and odor episodes in the files of inspector Cluzeau. Wat. Sci. Technol. 40, 15-21.
6. Cavalli J. F., Tomi F., Bernardini A. F., and Casanova J. (2004), Dihydroagarofurans: the fourth isomer isolated from Cedrelopsis grevei bark oil. Magn. Reson. Chem. 42, 709-711
7. Dickschat J. S., Wenzel S. C., Bode H. B., Müller R., and Schulz S. (2004), Biosynthesis of volatiles by the myxobacterium Myxococcus xanthus. Chembiochem 5, 778-787.
8. Ganßer D., Pollak F., and Berger R. G. (1995), A sesquiterpene alcohol from Streptomyces citreus CBS 109.60. J. Nat. Prod. 58, 1790-1793.
9. Gerber N. N. (1968), Geosmin, from microorganisms, is trans-1,10-dimethyl-trans-9-decalol. Tetrahedron, 2971-2974.
10. Gonzalez A. G., Jimenez I. A., Ravelo A. G., Coll J., Gonzalez J. A., and Lloria J. (1997), Antifeedant activity of sesquiterpenes from Celastraceae. Biochem. Syst. Ecol. 25, 513-519.
11. Höckelmann C. and Jüttner F. (2004), Volatile organic compound (VOC) analysis and sources of limonene, cyclohexanone and straight chain aldehydes in axenic cultures of Calothrix and Plectonema. Wat. Sci. Technol. 49, 47-54.
12. Höckelmann C., Moens T., and Jüttner F. (2004), Odour compounds from cyanobacterial biofilms acting as attractants and repellents for free-living nematodes. Limnol. Oceanogr. 49, 1809-1819.
13. Jiang J. and Cane D. E. (2008), Geosmin biosynthesis. Mechanism of the fragmentation-rearrangement in the conversion of germacradienol to geosmin. J. Am. Chem. Soc. 130, 428-429.
14. Jiang J., He X., and Cane D. E. (2007), Biosynthesis of the earthy odorant geosmin by a bifunctional Streptomyces coelicolor enzyme. Nature Chem. Biol. 3, 711-715.
15. Jüttner F. (1988), Quantitative trace analysis of volatile organic compounds. Methods Enzymol. 167, 609-616.
16. Jüttner F. and Watson S. B. (2007), Biochemical and ecological control of geosmin and 2-methylisoborneol in source waters. Appl. Environ. Microbiol. 73, 4395-4406.
17. Kiran S. R., Devi P. S., and Reddy K. L. (2007), Bioactivity of essential oils and sesquiterpenes of Chloroxylon swietenia DC against Helicoverpa armigera. Curr. Sci. 93, 544-548.
18. Ludwig F., Medger A., Börnick H., Opitz M., Lang K., Göttfert M., and Röske I. (2007), Identification and expression analyses of putative sesquiterpene synthase genes in Phormidium sp. and prevalence of geoA-like genes in a drinking water reservoir. Appl. Environ. Microbiol. 73, 6988-6993.
19. Nawrath T., Dickschat J. S., Müller R., Jiang J., Cane D. E., and Schulz S. (2008), Identification of (8S,9S,10S)-8,10- dimethyl-1-octalin, a key intermediate in the biosynthesis of geosmin in bacteria. J. Am. Chem. Soc. 130, 430-431.
20. Panella N. A., Dolan M. C., Karchesy J. J., Xiong Y., Peralta-Cruz J., Khasawneh M., Montenieri J. A., and Maupin G. O. (2005), Use of novel compounds for pest control: Insecticidal and acaricidal activity of essential oil components from heartwood of Alaska yellow cedar. J. Med. Entomol. 42, 352-358.
21. Persson P. E. (1980), Sensory properties and analysis of two muddy odour compounds, geosmin and 2-methylisoborneol, in water and fish. Wat. Res. 14, 1113-1118.
22. Pollak F. C. and Berger R. G. (1996), Geosmin and related volatiles in bioreactor-cultured Streptomyces citreus CBS 109.60. Appl. Environ. Microbiol. 62, 1295-1299.
23. Rosen A. A., Safferman R. S., Mashni C. I., and Romano A. H. (1968), Identity of odorous substance produced by Streptomyces griseoluteus. Appl. Microbiol. 16, 178-179.
24. Southwell I. A. (1978), The constituents of Rubus rosifolius. The structure of rosifoliol, a biogenetically significant sesquiterpenoid. Aust. J. Chem. 31, 2527-2538.
25. Spörle F., Becker H., Allen N. S., and Gupta M. P. (1991), Occurrence of (-)-geosmin and other terpenoids in an axenic culture of the liverwort Symphyogyna brongniartii. Z. Naturforsch. 46c, 183-188.
26. Thomas A. F. and Ozainne M. (1976), The stereochemistry of the dihydroagarofurans. Tetrahedron Lett., 1717-1718.
27. Todorova A. and Jüttner F. (1996), Ecotoxicological analysis of nostocyclamide, a modified cyclic hexapeptide from Nostoc. Phycologia 35 (Suppl. 6), 183-188.
28. Tsuchiya Y. and Matsumoto A. (1988), Identification of volatile metabolites produced by blue-green algae. Wat. Sci. Technol. 20, 149-155.
29. Tsuchiya Y., Matsumoto A., and Okamoto T. (1981), Identification of volatile metabolites produced by blue-green algae, Oscillatoria splendida, O. amoena, O. geminata, and Aphanizomenon sp. Yakugaku Zasshi 101, 852-856.
30. Weber C. I. (1993), Dilution waters. In: Methods for Measuring the Acute Toxicity of Effluents and Receiving Waters to Freshwater and Marine Organisms. Environmental Monitoring Systems Laboratory, Office of Research and Development, ed. U.S. Environmental Protection Agency, Cincinnatti, Ohio, pp. 28-30.