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.
Becher
Paul G
PG
Limnological Station, Institute of Plant Biology, University of Zürich, Seestrasse 187, 8802 Kilchberg, Switzerland. paul.becher@unine.ch
Keller
Simone
S
Jung
Günther
G
Süssmuth
Roderich D
RD
Jüttner
Friedrich
F
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