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Systemic deterrence of aphid probing and feeding by novel β-damascone analogues.

Gabryś B, Dancewicz K, Gliszczyńska A, Kordan B, Wawrzeńczyk C - J Pest Sci (2004) (2014)

Bottom Line: The most effective structural modification that evoked the strongest negative response from M. persicae was the transformation of β-damascone into δ-bromo-γ-lactone.The behavioural effect of this transformation was demonstrated in frequent interruption of probing in peripheral tissues, which caused repeated failures in finding sieve elements, and reduction in the ingestion time during the phloem phase in favour of watery salivation.The inhibition of aphid probing at both the pre-phloem and phloem levels reveals the passage of the compounds studied through the plant surface and their distribution within plant tissues in a systemic way, which may reduce the risk of the transmission of non-persistent and persistent viruses.

View Article: PubMed Central - PubMed

Affiliation: Department of Botany and Ecology, University of Zielona Góra, Szafrana 1, 65-516 Zielona Góra, Poland.

ABSTRACT

β-Damascone appeared a weak attractant close to not active to Myzus persicae, but modifications of its structure caused the avoidance of treated leaves by aphids during settling and reluctance to probe in simple choice- and no-choice experiments in previous studies. Here, the electrical penetration graph (EPG) technique, which allows monitoring of aphid probing within plant tissues, was applied to explore the biological background and localisation in plant tissues of the deterrent activities of β-damascone and its analogues. Activity of β-damascone and β-damascone-derived compounds depended on their substituents, which was manifested in the variation in the potency of the behavioural effect and differences in aphid probing phases that were affected. β-Damascone appeared a behaviourally inactive compound. The moderately active β-damascone ester affected aphid activities only during the phloem phase. The highly active deterrents-dihydro-β-damascol, β-damascone acetate, δ-bromo-γ-lactone, and unsaturated γ-lactone-affected pre-phloem and phloem aphid probing activities. The most effective structural modification that evoked the strongest negative response from M. persicae was the transformation of β-damascone into δ-bromo-γ-lactone. The behavioural effect of this transformation was demonstrated in frequent interruption of probing in peripheral tissues, which caused repeated failures in finding sieve elements, and reduction in the ingestion time during the phloem phase in favour of watery salivation. The inhibition of aphid probing at both the pre-phloem and phloem levels reveals the passage of the compounds studied through the plant surface and their distribution within plant tissues in a systemic way, which may reduce the risk of the transmission of non-persistent and persistent viruses.

No MeSH data available.


Related in: MedlinePlus

Chemical structures of β-damascone (1) and its studied analogues (2–11)
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Related In: Results  -  Collection


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Fig1: Chemical structures of β-damascone (1) and its studied analogues (2–11)

Mentions: Compounds studied for the probing and feeding behaviour of M. persicae are illustrated in Fig. 1. β-Damascone (1) was purchased from Sigma-Aldrich. All ten chemical derivatives (2–11) of β-damascone (1) were obtained by chemical synthesis as described by Gliszczyńska et al. (2014). The first step of synthesis was the reduction of β-damascone (1) with LiAlH4 to ketone-dihydro-β-damascone (2), which was subsequently transformed into corresponding allylic alcohol-dihydro-β-damascol (3). The Claisen-Johnson rearrangement (orthoacetate modification) of alcohol (3) was the key step of the described synthesis. The product of this rearrangement, γ, δ-unsaturated ethyl ester—ethyl 2-(2-butylidene-1,3,3-trimethylcyclohexyl)-acetate (4), was next hydrolyzed (KOH, EtOH) to 2-(2-butylidene-1,3,3-trimethylcyclohexyl) acetic acid (5). Product (5) was transformed into δ-halo-γ-lactones: 7a-(1-bromobutyl)-3a,7,7-trimethylhexahydrobenzofuran-2-one (6), 7a-(1-chlorobutyl)-3a,7,7-trimethylhexahydrobenzofuran-2-one (8) and γ-halo-δ-lactones: 7a-bromo-3a,7,7-trimethyl-8-propyloctahydroisochromen-3-one (7) and 7a-chloro-3a,7,7-trimethyl-8-propyloctahydroizochromen-2-one (9) in the bromo- and chlorolactonisation process under basic conditions (NBS/NCS, THF). The lactones 7a-((E)-but-1-enyl)-3a,7,7-trimethylhexahydrobenzofuran-2-one (10) and 3a,7,7-trimethyl-8-propylhexahydro,cyclopropa[1,2]benzofuran-2(3H)-one (11) were the products of the dehydrohalogenation reaction of the respective δ-halo-γ-lactones (6), (8) and γ-halo-δ-lactone (7), and (9) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).Fig. 1


Systemic deterrence of aphid probing and feeding by novel β-damascone analogues.

Gabryś B, Dancewicz K, Gliszczyńska A, Kordan B, Wawrzeńczyk C - J Pest Sci (2004) (2014)

Chemical structures of β-damascone (1) and its studied analogues (2–11)
© Copyright Policy - OpenAccess
Related In: Results  -  Collection

Show All Figures
getmorefigures.php?uid=PMC4539356&req=5

Fig1: Chemical structures of β-damascone (1) and its studied analogues (2–11)
Mentions: Compounds studied for the probing and feeding behaviour of M. persicae are illustrated in Fig. 1. β-Damascone (1) was purchased from Sigma-Aldrich. All ten chemical derivatives (2–11) of β-damascone (1) were obtained by chemical synthesis as described by Gliszczyńska et al. (2014). The first step of synthesis was the reduction of β-damascone (1) with LiAlH4 to ketone-dihydro-β-damascone (2), which was subsequently transformed into corresponding allylic alcohol-dihydro-β-damascol (3). The Claisen-Johnson rearrangement (orthoacetate modification) of alcohol (3) was the key step of the described synthesis. The product of this rearrangement, γ, δ-unsaturated ethyl ester—ethyl 2-(2-butylidene-1,3,3-trimethylcyclohexyl)-acetate (4), was next hydrolyzed (KOH, EtOH) to 2-(2-butylidene-1,3,3-trimethylcyclohexyl) acetic acid (5). Product (5) was transformed into δ-halo-γ-lactones: 7a-(1-bromobutyl)-3a,7,7-trimethylhexahydrobenzofuran-2-one (6), 7a-(1-chlorobutyl)-3a,7,7-trimethylhexahydrobenzofuran-2-one (8) and γ-halo-δ-lactones: 7a-bromo-3a,7,7-trimethyl-8-propyloctahydroisochromen-3-one (7) and 7a-chloro-3a,7,7-trimethyl-8-propyloctahydroizochromen-2-one (9) in the bromo- and chlorolactonisation process under basic conditions (NBS/NCS, THF). The lactones 7a-((E)-but-1-enyl)-3a,7,7-trimethylhexahydrobenzofuran-2-one (10) and 3a,7,7-trimethyl-8-propylhexahydro,cyclopropa[1,2]benzofuran-2(3H)-one (11) were the products of the dehydrohalogenation reaction of the respective δ-halo-γ-lactones (6), (8) and γ-halo-δ-lactone (7), and (9) with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU).Fig. 1

Bottom Line: The most effective structural modification that evoked the strongest negative response from M. persicae was the transformation of β-damascone into δ-bromo-γ-lactone.The behavioural effect of this transformation was demonstrated in frequent interruption of probing in peripheral tissues, which caused repeated failures in finding sieve elements, and reduction in the ingestion time during the phloem phase in favour of watery salivation.The inhibition of aphid probing at both the pre-phloem and phloem levels reveals the passage of the compounds studied through the plant surface and their distribution within plant tissues in a systemic way, which may reduce the risk of the transmission of non-persistent and persistent viruses.

View Article: PubMed Central - PubMed

Affiliation: Department of Botany and Ecology, University of Zielona Góra, Szafrana 1, 65-516 Zielona Góra, Poland.

ABSTRACT

β-Damascone appeared a weak attractant close to not active to Myzus persicae, but modifications of its structure caused the avoidance of treated leaves by aphids during settling and reluctance to probe in simple choice- and no-choice experiments in previous studies. Here, the electrical penetration graph (EPG) technique, which allows monitoring of aphid probing within plant tissues, was applied to explore the biological background and localisation in plant tissues of the deterrent activities of β-damascone and its analogues. Activity of β-damascone and β-damascone-derived compounds depended on their substituents, which was manifested in the variation in the potency of the behavioural effect and differences in aphid probing phases that were affected. β-Damascone appeared a behaviourally inactive compound. The moderately active β-damascone ester affected aphid activities only during the phloem phase. The highly active deterrents-dihydro-β-damascol, β-damascone acetate, δ-bromo-γ-lactone, and unsaturated γ-lactone-affected pre-phloem and phloem aphid probing activities. The most effective structural modification that evoked the strongest negative response from M. persicae was the transformation of β-damascone into δ-bromo-γ-lactone. The behavioural effect of this transformation was demonstrated in frequent interruption of probing in peripheral tissues, which caused repeated failures in finding sieve elements, and reduction in the ingestion time during the phloem phase in favour of watery salivation. The inhibition of aphid probing at both the pre-phloem and phloem levels reveals the passage of the compounds studied through the plant surface and their distribution within plant tissues in a systemic way, which may reduce the risk of the transmission of non-persistent and persistent viruses.

No MeSH data available.


Related in: MedlinePlus