Insecticidal activity of 12-epi-hapalindole J isonitrile.
12-epi-Hapalindole J isonitrile (1) and three previously described hapalindoles, 12-epi-hapalindole C isonitrile (2), hapalindole L (3) and 12-epi-hapalindole E isonitrile (4) were isolated and identified as insecticidal alkaloids of the biofilm-forming freshwater cyanobacterium Fischerella ATCC 43239 (Stigonematales). The structures of the purified compounds were elucidated by ESI-FTICR-MS, GC-EI-MS and various 2D NMR experiments. At 26 microM hapalindole 1 killed 100% of the larvae of the dipteran Chironomus riparius within 48h. Insecticidal activities were also found at similar concentration for the hapalindoles 2-4. The bioactivity of hapalindoles demonstrates that cyanobacterial biofilms can be considered as promising sources of insecticidal metabolites which might be useful for the biocontrol of dipterans.
Limnological Station, Institute of Plant Biology, University of Zürich, Seestrasse 187, 8802 Kilchberg, Switzerland. paul.becher@unine.ch
Paul G
PG
Becher
Simone
S
Keller
Günther
G
Jung
Roderich D
RD
Süssmuth
Friedrich
F
Jüttner
D000818:Animals; D002683:Chironomidae / Q000187:drug effects* / Q000254:growth & development; D007211:Indoles / Q000737:chemistry / Q000494:pharmacology*; D007306:Insecticides; D007814:Larva / Q000187:drug effects*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D017550:Spectroscopy, Fourier Transform Infrared
C525204:12-hapalindole J isonitrile; D007211:Indoles; D007306:Insecticides