TY - JOUR
T1 - Novel antifeedant and insecticidal compounds from avocado idioblast cell oil
AU - Rodriguez-Saona, Cesar
AU - Millar, Jocelyn G.
AU - Maynard, David F.
AU - Trumble, John T.
N1 - Funding Information:
Acknowledgments—The authors thank Kristina White, Gregory Kund, and William Carson for laboratory assistance; Carlos Coviella, Stuart Reitz, J. Daniel Hare, and P. Kirk Visscher for critical reviews of the manuscript; and Kathryn Platt and William Thomson for helpful advice. We thank Richard Kondrat and Ron New (UC Riverside Analytical Facility) for high-resolution and CI mass spectra. We also thank Joshua C. Hoerger, Jefferson M. Caparas, and Theresa A. Aguilar (CSUSB) for assistance with the avocadofuran syntheses. This research was supported in part by the California Celery Research Advisory Board and the California Tomato Commission.
PY - 1998
Y1 - 1998
N2 - Several insecticidal compounds have been identified by bioassaydriven fractionation of avocado, Persea americana Mill, idioblast cell oil. A flash chromatography fraction of the oil showed substantial toxicity to early instars of the generalist insect herbivore, Spodoptera exigua (Hubner) (100% mortality after seven days). Following further fractionation, five biologically active compounds, 2-(pentadecyl)furan, 2-(heptadecyl)furan, 2-(1E-pentadecenyl)furan, 2-(8Z, 11Z-heptadecadienyl)furan, and the triglyceride triolein, were identified. Several minor components were also tentatively identified, including 2-(1Z-pentadecenyl)furan, 2-(1E-heptadecenyl)furan, and 2-(1E,8Z, 11Z-heptadecatrienyl)furan. Several 2-alkylfurans of this type have been reported previously from avocado (Persea spp.) and have received the common name of avocadofurans. The major compounds were tested individually for toxic and growth inhibitory effects. Individually, the compounds had low to moderate toxicity. Of these, 2-(pentadecyl)furan had the greatest effects, with an LC50 value of 1031 μg/g. At concentrations of 600 μg/g or higher in diets, larval growth was inhibited by >70% compared to controls. The analogous 2-(heptadecyl)furan had an LC50 value of 1206 μg/g, and also significantly reduced larval growth (>75% versus controls) at concentrations of > 600 μg/g. The unsaturated analogs 2-(1E-pentadecenyl)furan and 2-(8Z, 11Z-heptadecadienyl)furan were less toxic. Triolein was only weakly toxic, with an LC50 value of 10,364 μg/g diet. Larval growth was inhibited only at concentrations of 7000 μg/g or higher. The potential of avocadofurans in insect control is discussed.
AB - Several insecticidal compounds have been identified by bioassaydriven fractionation of avocado, Persea americana Mill, idioblast cell oil. A flash chromatography fraction of the oil showed substantial toxicity to early instars of the generalist insect herbivore, Spodoptera exigua (Hubner) (100% mortality after seven days). Following further fractionation, five biologically active compounds, 2-(pentadecyl)furan, 2-(heptadecyl)furan, 2-(1E-pentadecenyl)furan, 2-(8Z, 11Z-heptadecadienyl)furan, and the triglyceride triolein, were identified. Several minor components were also tentatively identified, including 2-(1Z-pentadecenyl)furan, 2-(1E-heptadecenyl)furan, and 2-(1E,8Z, 11Z-heptadecatrienyl)furan. Several 2-alkylfurans of this type have been reported previously from avocado (Persea spp.) and have received the common name of avocadofurans. The major compounds were tested individually for toxic and growth inhibitory effects. Individually, the compounds had low to moderate toxicity. Of these, 2-(pentadecyl)furan had the greatest effects, with an LC50 value of 1031 μg/g. At concentrations of 600 μg/g or higher in diets, larval growth was inhibited by >70% compared to controls. The analogous 2-(heptadecyl)furan had an LC50 value of 1206 μg/g, and also significantly reduced larval growth (>75% versus controls) at concentrations of > 600 μg/g. The unsaturated analogs 2-(1E-pentadecenyl)furan and 2-(8Z, 11Z-heptadecadienyl)furan were less toxic. Triolein was only weakly toxic, with an LC50 value of 10,364 μg/g diet. Larval growth was inhibited only at concentrations of 7000 μg/g or higher. The potential of avocadofurans in insect control is discussed.
KW - 2-(heptadecyl)furan
KW - 2-(pentadecyl)furan
KW - Avocado
KW - Avocadofuran
KW - Idioblast cells
KW - Perseaamericana
KW - Spodopteraexigua
KW - Triolein
UR - http://www.scopus.com/inward/record.url?scp=0031748098&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=0031748098&partnerID=8YFLogxK
U2 - 10.1023/A:1022325601724
DO - 10.1023/A:1022325601724
M3 - Article
AN - SCOPUS:0031748098
SN - 0098-0331
VL - 24
SP - 867
EP - 889
JO - Journal of Chemical Ecology
JF - Journal of Chemical Ecology
IS - 5
ER -