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Geranylacetone and nerylacetone are natural sesquiterpenoids, which play various roles in plant-insect interactions, including the deterrent and repellent effects on herbivores. The structural modifications of natural compounds often change their biological activities. The aim of the study was to evaluate the effect of geranylacetone, nerylacetone and their epoxy-derivatives on the probing and settling behavior of (Sulz.) (Hemiptera: Aphididae). The no-choice test using the Electrical Penetration Graph (EPG) technique showed that the probes before the first phloem phase were usually shorter than 3 min, which means that they were terminated within the epidermis and/or outer layers of mesophyll. This resulted in a tendency to delay the initiation of the phloem phase in aphids, which reflects a weak preingestive deterrent activity of the studied compounds at the level of non-vascular tissues. Most showed bouts of sustained phloem sap ingestion. However, the 24-h free-choice test demonstrated that aphids did not settle on the leaves treated with geranylacetone, nerylacetone, and their epoxy-derivatives. The refusal to settle after the consumption of phloem sap on treated plants indicated that the studied compounds had postingestive deterrent activity. The epoxidation of geranylacetone and nerylacetone did not evoke significant changes in their activity profiles.
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http://dx.doi.org/10.3390/molecules27248871 | DOI Listing |
Molecules
December 2022
Department of Botany and Ecology, University of Zielona Góra, Szafrana 1, 65-516 Zielona Góra, Poland.
Geranylacetone and nerylacetone are natural sesquiterpenoids, which play various roles in plant-insect interactions, including the deterrent and repellent effects on herbivores. The structural modifications of natural compounds often change their biological activities. The aim of the study was to evaluate the effect of geranylacetone, nerylacetone and their epoxy-derivatives on the probing and settling behavior of (Sulz.
View Article and Find Full Text PDFBeilstein J Org Chem
July 2014
Institute of Biochemistry, Heinrich-Heine University Düsseldorf, Universitätsstr. 1, 40225 Düsseldorf.
Allylic alcohols are valuable precursors in the synthesis of pharmaceutical intermediates, agrochemicals and natural products. Regioselective oxidation of parental alkenes is a challenging task for chemical catalysts and requires several steps including protection and deprotection. Many cytochrome P450 enzymes are known to catalyse selective allylic hydroxylation under mild conditions.
View Article and Find Full Text PDFChembiochem
March 2009
Institute of Technical Biochemistry, University of Stuttgart, Allmandring 31, 70569 Stuttgart, Germany.
A minimal CYP102A1 mutant library of only 24 variants plus wild type was constructed by combining five hydrophobic amino acids (alanine, valine, phenylalanine, leucine and isoleucine) in two positions. Both positions are located close to the centre of the haem group. The first, position 87, has been shown to mediate substrate specificity and regioselectivity in CYP102A1.
View Article and Find Full Text PDFOrg Lett
October 2005
Department of Chemistry, University of Iowa, Iowa City, 52242, USA.
[structure: see text] The four olefin stereoisomers of farnesol have been synthesized from readily available nerylacetone or commercial geranylacetone. A new variation on the use of beta-oxido ylides favored the (2Z)-stereoisomers, whereas the (2E)-isomers were obtained through a classical Horner-Wadsworth-Emmons condensation with triethyl phosphonoacetate and reduction of the resulting ester.
View Article and Find Full Text PDFBiosci Biotechnol Biochem
April 1995
Department of Applied Biological Chemistry, Faculty of Agriculture, Niigata University, Japan.
The inhibitors of 2,3-oxidosqualene:lanosterol cyclase were investigated by comparative studies between pig's liver and Baker's yeast. The fundamental skeleton of the inhibitors was 8-azadecalin. To the nitrogen atom, an isoprenoid-like chain [nerylacetone (Z-form), geranylacetone (E-form) or its hydrogenated form] was attached by the reaction of reductive amination with NaCNBH3.
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