(<i>E</i>)-2-(2-Hydroxyethylidene)-6-methyl-5-heptenal (α-Acariolal) and (<i>E</i>)-2-(2-Hydroxyethyl)-6-methyl-2,5-heptadienal (β-Acariolal), Two New Types of Isomeric Monoterpenes…

Shimizu, Nobuhiro; Tarui, Hirokazu; Mori, Naoki; Nishida, Ritsuo; Kuwahara, Yasumasa

doi:10.1271/bbb.67.308

Cited by 10 publications

(2 citation statements)

References 11 publications

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“…Larvae responded most strongly to pheromone concentrations of 50 fm/cm 2 and this effect decreased at higher concentrations. A similar phenomenon has been observed for pheromones in multiple other species where higher doses induce a less robust behavioral response, or even begin to elicit alarm or escape behaviors, compared with lower doses ( Leal et al, 1989 ; Shimizu et al, 2003 ). Finally, we assayed the larval response to an equimolar mixture ((25 fmol:25 fmol)/cm 2 ) of the two compounds.…”

Section: Resultssupporting

confidence: 70%

Evolved differences in larval social behavior mediated by novel pheromones

Mast

Moraes

Alborn

et al. 2014

eLife

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Pheromones, chemical signals that convey social information, mediate many insect social behaviors, including navigation and aggregation. Several studies have suggested that behavior during the immature larval stages of Drosophila development is influenced by pheromones, but none of these compounds or the pheromone-receptor neurons that sense them have been identified. Here we report a larval pheromone-signaling pathway. We found that larvae produce two novel long-chain fatty acids that are attractive to other larvae. We identified a single larval chemosensory neuron that detects these molecules. Two members of the pickpocket family of DEG/ENaC channel subunits (ppk23 and ppk29) are required to respond to these pheromones. This pheromone system is evolving quickly, since the larval exudates of D. simulans, the sister species of D. melanogaster, are not attractive to other larvae. Our results define a new pheromone signaling system in Drosophila that shares characteristics with pheromone systems in a wide diversity of insects.DOI: http://dx.doi.org/10.7554/eLife.04205.001

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Section: Resultssupporting

confidence: 70%

Evolved differences in larval social behavior mediated by novel pheromones

Mast

Moraes

Alborn

et al. 2014

eLife

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“…On the other hand, the isolation of the free γ-hydroxycarboxylic acid after acidification of the potassium salt and subsequent extraction is reported, too [18]. Commonly, the γ-hydroxycarboxylate is protonated in situ [19] or the crude mixture after acidification of the γ-hydroxycarboxylate is directly used for further transformations [20, 21]. An interesting aspect is the potential stabilization of the γ-hydroxycarboxylic acid by basic moieties of the molecular structure and formation of a zwitterionic species [22].…”

Section: Resultsmentioning

confidence: 99%

Synthesis of γ-hydroxy-α-(arylmethyl)carboxylic acids from lactones: pathway to a structural motif derived from lactic acid and amino acid analogs?

et al. 2019

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Objective A synthetic pathway to γ-hydroxy-α-(arylmethyl)carboxylic acids starting from α-angelica lactone and γ-butyrolactone was investigated. These γ-hydroxycarboxylic acids resemble structural motifs of lactic acid and amino acids. The possibility of cocondensation with lactic acid towards functionalized poly(lactic acid)s was analyzed. Results The functional γ-hydroxycarboxylates sodium 4-hydroxy-2-(( N -methylpyrazol-4-yl)methyl)pentanoate and sodium 4-hydroxy-2-(phenylmethyl)butanoate (2-benzyl-4-hydroxybutanoate) were synthesized in good yields as a proof of concept for the proposed reaction pathway. Additionally, sodium ( E )-2-(( N -methylpyrazol-4-yl)methylene)-4-oxopentanoate presenting an interesting structural motif was isolated. All products have been fully characterized by mass spectrometry, IR spectroscopy and 2D nuclear magnetic resonance (NMR) techniques. In contrast to the carboxylate anions, the corresponding carboxylic acids obtained after acidification were found to be unstable. The instability was analyzed by NMR experiments. With the help of diffusion ordered NMR spectroscopy, the cocondensation with lactic acid was elucidated. The reaction products were characterized as oligomers of pure lactic acid, while intramolecular condensation of the γ-hydroxycarboxylic acids prevents cocondensation with lactide. Electronic supplementary material The online version of this article (10.1186/s13104-019-4232-1) contains supplementary material, which is available to authorized users.

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A labeling study on the formation of perillene by submerged cultured oyster mushroom, Pleurotus ostreatus

Krings

Hapetta

Berger

2008

Appl Microbiol Biotechnol

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The conversion of beta-myrcene to the furanoid flavour compound perillene by Pleurotus ostreatus was investigated using trideutero beta-myrcene, trideutero alpha-(Z)-acaridiol and non-labeled 1,2- and 3,10-epoxy-beta-myrcene, alpha,alpha-acarilactol, and perillene as substrates. Myrcene diols were formed from the cleavage of myrcene epoxides, but only alpha-(Z)-acaridiol, a 1,4-butanediol derivative most likely generated through a base-catalysed epoxide opening, was a suitable precursor of perillene. Once formed, this key intermediate was rapidly oxidised and the resulting cyclic lactol was dehydrated to yield perillene. Bioconversion of the supplemented perillene to alpha,alpha-acariolide indicated that perillene was another intermediate of the pathway and prone to further oxidative degradation. The data suggest that the fungus converted the cytotoxic beta-myrcene in its environment into a metabolically useable carbon source along this route.

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(E)-2-(2-Hydroxyethylidene)-6-methyl-5-heptenal (α-Acariolal) and (E)-2-(2-Hydroxyethyl)-6-methyl-2,5-heptadienal (β-Acariolal), Two New Types of Isomeric Monoterpenes…

Cited by 10 publications

References 11 publications

Evolved differences in larval social behavior mediated by novel pheromones

Evolved differences in larval social behavior mediated by novel pheromones

Synthesis of γ-hydroxy-α-(arylmethyl)carboxylic acids from lactones: pathway to a structural motif derived from lactic acid and amino acid analogs?

A labeling study on the formation of perillene by submerged cultured oyster mushroom, Pleurotus ostreatus

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