Divergent Diastereoselective Synthesis of Iridomyrmecin, Isoiridomyrmecin, Teucrimulactone, and Dolicholactone from Citronellol

Fischman, Clara J.; Adler, Snow; Hofferberth, John E.

doi:10.1021/jo400884g

Cited by 18 publications

(11 citation statements)

References 31 publications

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“…In total 6 chemical standards were produced, including: (4 R ,4a R ,7 R ,7a S )-(−)-iridomyrmecin (87% pure), a 1:1 mix of (4 S ,4a R ,7 R ,7a S )-(+)-isoiridomyrmecin and (4 R ,4a R ,7 R ,7a S )-(−)-iridomyrmecin, ( R )-actinidine (95% pure), ( R )-actinidine (20% EtOAc) and (1 S ,4a R ,7 R ,7a S )-nepetalactol (Supplementary Figure 2). Syntheses were conducted as described previously for stereoisomers of iridomyrmecin (Stökl et al 2012; Fischman et al 2013) as well as for actinidine and nepetalactol (Beckett et al 2010) using ( R )-citronellal as starting material. Dilutions of each of the synthetic odors were prepared in hexane for both electrophysiological and behavioral trials, and synthetic chemicals were stored with nitrogen in sealed containers and kept in the dark at -80 °C when not in use.…”

Section: Methodsmentioning

confidence: 99%

Plant-Based Natural Product Chemistry for Integrated Pest Management of Drosophila suzukii

et al. 2019

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Since the first reports of damage by Drosophila suzukii , the spotted-wing Drosophila (SWD), over a decade ago in Europe, widespread efforts have been made to understand both the ecology and the evolution of this insect pest, especially due to its phylogenetic proximity to one of the original model organisms, D. melanogaster . In addition, researchers have sought to find economically viable solutions for the monitoring and management of this agricultural pest, which has now swept across much of Europe, North America and Asia. In a new direction of study, we present an investigation of plant-based chemistry, where we search for natural compounds that are structurally similar to known olfactory cues from parasitoid wasps that in turn are well-described ovipositional avoidance cues for many Drosophila species. Here we test 11 plant species across two plant genera, Nepeta and Actinidia , and while we find iridoid compounds in both, only those odorants from Actinidia are noted to be detected by the insect antenna, and in addition, found to be behaviorally active. Moreover, the Actinidia extracts resulted in oviposition avoidance when they were added to fruit samples in the laboratory. Thus we propose the possible efficacy of these plants or their extracted chemistry as a novel means for establishing a cost-effective integrated pest management strategy towards the control of this pest fly. Electronic supplementary material The online version of this article (10.1007/s10886-019-01085-1) contains supplementary material, which is available to authorized users.

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Section: Methodsmentioning

confidence: 99%

Plant-Based Natural Product Chemistry for Integrated Pest Management of Drosophila suzukii

et al. 2019

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“…Stereoisomers of Iridomyrmecin were synthesized as described in [ 12 ] and [ 57 ]. Actinidine and Nepetalactol were synthesized as described by [ 58 ].…”

Section: Methodsmentioning

confidence: 99%

Drosophila Avoids Parasitoids by Sensing Their Semiochemicals via a Dedicated Olfactory Circuit

et al. 2015

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Detecting danger is one of the foremost tasks for a neural system. Larval parasitoids constitute clear danger to Drosophila, as up to 80% of fly larvae become parasitized in nature. We show that Drosophila melanogaster larvae and adults avoid sites smelling of the main parasitoid enemies, Leptopilina wasps. This avoidance is mediated via a highly specific olfactory sensory neuron (OSN) type. While the larval OSN expresses the olfactory receptor Or49a and is tuned to the Leptopilina odor iridomyrmecin, the adult expresses both Or49a and Or85f and in addition detects the wasp odors actinidine and nepetalactol. The information is transferred via projection neurons to a specific part of the lateral horn known to be involved in mediating avoidance. Drosophila has thus developed a dedicated circuit to detect a life-threatening enemy based on the smell of its semiochemicals. Such an enemy-detecting olfactory circuit has earlier only been characterized in mice and nematodes.

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“…Iridoids in L. victoriae were identified by comparing mass spectra and retention indices on both the non-polar and the cyclodextrin column to those of the L. heterotoma iridoids. Additionally, (+)-iridomyrmecin and (−)-iridomyrmecin as well as (+)-isoiridomyrmecin and (−)-isoiridomyrmecin were used as synthetic references (Fischman et al, 2013). Compounds that contributed less than 0.5 % to the total amount of iridoids were not considered.…”

Section: Iridoidsmentioning

confidence: 99%

Varying importance of cuticular hydrocarbons and iridoids in the species-specific mate recognition pheromones of three closely related Leptopilina species

et al. 2015

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Divergent Diastereoselective Synthesis of Iridomyrmecin, Isoiridomyrmecin, Teucrimulactone, and Dolicholactone from Citronellol

Cited by 18 publications

References 31 publications

Plant-Based Natural Product Chemistry for Integrated Pest Management of Drosophila suzukii

Plant-Based Natural Product Chemistry for Integrated Pest Management of Drosophila suzukii

Drosophila Avoids Parasitoids by Sensing Their Semiochemicals via a Dedicated Olfactory Circuit

Varying importance of cuticular hydrocarbons and iridoids in the species-specific mate recognition pheromones of three closely related Leptopilina species

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