Cargando…

β-Thujone and Its Derivatives Modify the Probing Behavior of the Peach Potato Aphid

Thujone is a natural biologically active monoterpene ketone component of essential oils of numerous plants. The aim of the study was to evaluate the effect of β-thujone and β-thujone derivatives bisulfite adduct, lactone, oxime, and lactam application on behavior of Myzus persicae (Sulz.) (Hemiptera...

Descripción completa

Detalles Bibliográficos
Autores principales: Wróblewska-Kurdyk, Anna, Gniłka, Radosław, Dancewicz, Katarzyna, Grudniewska, Aleksandra, Wawrzeńczyk, Czesław, Gabryś, Beata
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6572410/
https://www.ncbi.nlm.nih.gov/pubmed/31091712
http://dx.doi.org/10.3390/molecules24101847
_version_ 1783427634159419392
author Wróblewska-Kurdyk, Anna
Gniłka, Radosław
Dancewicz, Katarzyna
Grudniewska, Aleksandra
Wawrzeńczyk, Czesław
Gabryś, Beata
author_facet Wróblewska-Kurdyk, Anna
Gniłka, Radosław
Dancewicz, Katarzyna
Grudniewska, Aleksandra
Wawrzeńczyk, Czesław
Gabryś, Beata
author_sort Wróblewska-Kurdyk, Anna
collection PubMed
description Thujone is a natural biologically active monoterpene ketone component of essential oils of numerous plants. The aim of the study was to evaluate the effect of β-thujone and β-thujone derivatives bisulfite adduct, lactone, oxime, and lactam application on behavior of Myzus persicae (Sulz.) (Hemiptera: Aphididae) during probing and settling. The choice and no-choice tests (aphid settling and Electrical Penetration Graph (EPG), respectively) revealed that stereochemistry of thujone was important for biological activity (β-thujone caused changes in aphid behavior while α-thujone did not) and that cyclopentane ring modifications and functional groups addition gave derivatives that possessed stronger and more durable deterrent effects. The most effective modification was the incorporation of a lactam moiety into the β-thujone molecule. Application of β-thujone lactam limited aphid settling for at least 24 h, caused restlessness in aphids and a delay or failure in reaching phloem phase by M. persicae. β-Thujone lactam can be considered a deterrent of medium potency with activity expressed at preingestive phase of aphid probing. Other compounds did not restrain aphid stylet penetration in non-phloem tissues but slightly limited sap ingestion (lactone, oxime), and restrained aphid settling for a period of less than 24 h (β-Thujone, bisulphite adduct, lactone).
format Online
Article
Text
id pubmed-6572410
institution National Center for Biotechnology Information
language English
publishDate 2019
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-65724102019-06-18 β-Thujone and Its Derivatives Modify the Probing Behavior of the Peach Potato Aphid Wróblewska-Kurdyk, Anna Gniłka, Radosław Dancewicz, Katarzyna Grudniewska, Aleksandra Wawrzeńczyk, Czesław Gabryś, Beata Molecules Article Thujone is a natural biologically active monoterpene ketone component of essential oils of numerous plants. The aim of the study was to evaluate the effect of β-thujone and β-thujone derivatives bisulfite adduct, lactone, oxime, and lactam application on behavior of Myzus persicae (Sulz.) (Hemiptera: Aphididae) during probing and settling. The choice and no-choice tests (aphid settling and Electrical Penetration Graph (EPG), respectively) revealed that stereochemistry of thujone was important for biological activity (β-thujone caused changes in aphid behavior while α-thujone did not) and that cyclopentane ring modifications and functional groups addition gave derivatives that possessed stronger and more durable deterrent effects. The most effective modification was the incorporation of a lactam moiety into the β-thujone molecule. Application of β-thujone lactam limited aphid settling for at least 24 h, caused restlessness in aphids and a delay or failure in reaching phloem phase by M. persicae. β-Thujone lactam can be considered a deterrent of medium potency with activity expressed at preingestive phase of aphid probing. Other compounds did not restrain aphid stylet penetration in non-phloem tissues but slightly limited sap ingestion (lactone, oxime), and restrained aphid settling for a period of less than 24 h (β-Thujone, bisulphite adduct, lactone). MDPI 2019-05-14 /pmc/articles/PMC6572410/ /pubmed/31091712 http://dx.doi.org/10.3390/molecules24101847 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Wróblewska-Kurdyk, Anna
Gniłka, Radosław
Dancewicz, Katarzyna
Grudniewska, Aleksandra
Wawrzeńczyk, Czesław
Gabryś, Beata
β-Thujone and Its Derivatives Modify the Probing Behavior of the Peach Potato Aphid
title β-Thujone and Its Derivatives Modify the Probing Behavior of the Peach Potato Aphid
title_full β-Thujone and Its Derivatives Modify the Probing Behavior of the Peach Potato Aphid
title_fullStr β-Thujone and Its Derivatives Modify the Probing Behavior of the Peach Potato Aphid
title_full_unstemmed β-Thujone and Its Derivatives Modify the Probing Behavior of the Peach Potato Aphid
title_short β-Thujone and Its Derivatives Modify the Probing Behavior of the Peach Potato Aphid
title_sort β-thujone and its derivatives modify the probing behavior of the peach potato aphid
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6572410/
https://www.ncbi.nlm.nih.gov/pubmed/31091712
http://dx.doi.org/10.3390/molecules24101847
work_keys_str_mv AT wroblewskakurdykanna bthujoneanditsderivativesmodifytheprobingbehaviorofthepeachpotatoaphid
AT gniłkaradosław bthujoneanditsderivativesmodifytheprobingbehaviorofthepeachpotatoaphid
AT dancewiczkatarzyna bthujoneanditsderivativesmodifytheprobingbehaviorofthepeachpotatoaphid
AT grudniewskaaleksandra bthujoneanditsderivativesmodifytheprobingbehaviorofthepeachpotatoaphid
AT wawrzenczykczesław bthujoneanditsderivativesmodifytheprobingbehaviorofthepeachpotatoaphid
AT gabrysbeata bthujoneanditsderivativesmodifytheprobingbehaviorofthepeachpotatoaphid