TY - JOUR
T1 - Antifeedant and phytotoxic activity of the sesquiterpene p-benzoquinone perezone and some of its derivatives
AU - Burgueño-Tapia, Eleuterio
AU - Castillo, Lucia
AU - González-Coloma, Azucena
AU - Joseph-Nathan, Pedro
N1 - Funding Information:
Acknowledgments This work was supported by grants CTQ2006-15597-C02-01/PPQ, CSIC-CNRST, SIP-IPN, CONACYT and CYTED, and L. Castillo by AECI. We gratefully acknowledge S. Carlin for language revision.
PY - 2008/6
Y1 - 2008/6
N2 - The sesquiterpene p-benzoquinone perezone (1), isolated from Perezia adnata var. alamani (Asteraceae), and its non-natural derivatives isoperezone (2), dihydroperezone (3), dihydroisoperezone (4), and anilidoperezone (5) were tested as antifeedants against the herbivorous insects Spodoptera littoralis, Leptinotarsa decemlineata, and Myzus persicae. Compounds 1-5 exhibited strong antifeedant activity against L. decemlineata and M. persicae, and elicited a low response by S. littoralis. Antifeedant activity on L. decemlineata and M. persicae increased when the hydroxyl group at C-3 in perezone (1) was changed to C-6 to give isoperezone (2). The same effect was found with hydrogenation of the double bond of the alkyl chain of (1) to yield dihydroperezone (3). In contrast, hydrogenation of this double bond in isoperezone (2) to give dihydroisoperezone (4) led to a reduction in antifeedant activity. Determination of the phytotoxic activity of 1-5 revealed that 3 had a significant inhibition effect on Lactuca sativa radicle length growth.
AB - The sesquiterpene p-benzoquinone perezone (1), isolated from Perezia adnata var. alamani (Asteraceae), and its non-natural derivatives isoperezone (2), dihydroperezone (3), dihydroisoperezone (4), and anilidoperezone (5) were tested as antifeedants against the herbivorous insects Spodoptera littoralis, Leptinotarsa decemlineata, and Myzus persicae. Compounds 1-5 exhibited strong antifeedant activity against L. decemlineata and M. persicae, and elicited a low response by S. littoralis. Antifeedant activity on L. decemlineata and M. persicae increased when the hydroxyl group at C-3 in perezone (1) was changed to C-6 to give isoperezone (2). The same effect was found with hydrogenation of the double bond of the alkyl chain of (1) to yield dihydroperezone (3). In contrast, hydrogenation of this double bond in isoperezone (2) to give dihydroisoperezone (4) led to a reduction in antifeedant activity. Determination of the phytotoxic activity of 1-5 revealed that 3 had a significant inhibition effect on Lactuca sativa radicle length growth.
KW - Antifeedant
KW - Isoperezone
KW - Perezone
KW - Phytotoxicity
UR - http://www.scopus.com/inward/record.url?scp=45849137822&partnerID=8YFLogxK
U2 - 10.1007/s10886-008-9495-2
DO - 10.1007/s10886-008-9495-2
M3 - Artículo
SN - 0098-0331
VL - 34
SP - 766
EP - 771
JO - Journal of Chemical Ecology
JF - Journal of Chemical Ecology
IS - 6
ER -