Dimethylfuran-Lactone Pheromone from Males of Galerucella calmariensis and Galerucella pusilla

Bartelt, Robert J.; Cossé, Allard A.; Zilkowski, Bruce W.; Weisleder, David; Grode, Stephen H.; Wiedenmann, Robert N.; Post, Susan L.

doi:10.1007/s10886-005-9026-3

Cited by 28 publications

(32 citation statements)

References 32 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, natural products bearing the tetraalkyl-substituted furan ring are relatively unstable, which is a possible reason why the tetraalkyl-substituted furan ring has rarely been found in nature. Recently, a macrolactone bearing a tetraalkyl-substituted furan ring was identified as the aggregation pheromone of leaf beetle (37) and, to the best our knowledge, this is the only example of a tetraalkyl furan ring in a natural product except for F-acids. Moreover, the activity of the green-lipped mussel is known to disappear in aqueous solution.…”

Section: Resultsmentioning

confidence: 96%

Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

Wakimoto

Kondo

Nii

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

104

View full text Add to dashboard Cite

A lipid extract of Perna canaliculus (New Zealand green-lipped mussel) has reportedly displayed anti-inflammatory effects in animal models and in human controlled studies. However, the anti-inflammatory lipid components have not been investigated in detail due to the instability of the lipid extract, which has made the identification of the distinct active components a formidable task. Considering the instability of the active component, we carefully fractionated a lipid extract of Perna canaliculus (Lyprinol) and detected furan fatty acids (F-acids). These naturally but rarely detected fatty acids show potent radical-scavenging ability and are essential constituents of plants and algae. Based on these data, it has been proposed that F-acids could be potential antioxidants, which may contribute to the protective properties of fish and fish oil diets against chronic inflammatory diseases. However, to date, in vivo data to support the hypothesis have not been obtained, presumably due to the limited availability of F-acids. To confirm the in vivo anti-inflammatory effect of F-acids in comparison with that of eicosapentaenoic acid (EPA), we developed a semisynthetic preparation and examined its anti-inflammatory activity in a rat model of adjuvant-induced arthritis. Indeed, the F-acid ethyl ester exhibited more potent anti-inflammatory activity than that of the EPA ethyl ester. We report on the in vivo activity of F-acids, confirming that the lipid extract of the green-lipped mussel includes an unstable fatty acid that is more effective than EPA.

show abstract

Section: Resultsmentioning

confidence: 96%

Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

Wakimoto

Kondo

Nii

et al. 2011

Proc. Natl. Acad. Sci. U.S.A.

104

View full text Add to dashboard Cite

show abstract

“…In most cases, however, the synthetic pheromone compounds alone are only weakly attractive (Cossé et al, 2002;Dickens et al, 2002;Rao et al, 2003;Soroka et al, 2005;Tóth et al, 2005;Bartelt et al, 2006;. Peng and Weiss (1992) first provided evidence for a male-produced aggregation pheromone in P. cruciferae, and subsequently six male-specific sesquiterpenes were identified, four of which have been synthesized (Bartelt et al, 2001Muto et al, 2004).…”

Section: Introductionmentioning

confidence: 99%

Male Phyllotreta striolata (F.) Produce an Aggregation Pheromone: Identification of Male-specific compounds and Interaction with Host Plant Volatiles

et al. 2010

View full text Add to dashboard Cite

The chrysomelid beetle Phyllotreta striolata is an important pest of Brassicaceae in Southeast Asia and North America. Here, we identified the aggregation pheromone of a population of P. striolata from Taiwan, and host plant volatiles that interact with the pheromone. Volatiles emitted by feeding male P. striolata attracted males and females in the field. Headspace volatile analyses revealed that six sesquiterpenes were emitted specifically by feeding males. Only one of these, however, elicited an electrophysiological response from antennae of both sexes. A number of host plant volatiles, e.g., 1-hexanol, (Z)-3-hexen-1-ol, and the glucosinolate hydrolysis products allyl isothiocyanate (AITC), 3-butenyl isothiocyanate, and 4-pentenyl isothiocyanate also elicited clear responses from the antenna. The active male-specific compound was identified as (+)-(6R,7S)-himachala-9,11-diene by chiral stationary phase gas-chromatography with coupled mass spectrometry, and by comparison with reference samples from Abies nordmanniana, which is known to produce the corresponding enantiomer. The pheromone compound was synthesized starting from (-)-α-himachalene isolated from Cedrus atlantica. Under field conditions, the activity of the synthetic pheromone required concomitant presence of the host plant volatile allyl isothiocyanate. However, both synthetic (+)-(6R,7S)-himachala-9,11-diene alone and in combination with AITC were attractive in a two-choice laboratory assay devoid of other natural olfactory stimuli. We hypothesize that P. striolata adults respond to the pheromone only if specific host volatiles are present. In the same laboratory set up, more beetles were attracted by feeding males than by the synthetic stimuli. Thus, further research will be necessary to reveal the components of a more complex blend of host or male-produced semiochemicals that might enhance trap attractiveness in the field.

show abstract

“…However, the dispersal ability of G. pusilla was not investigated. Bartelt et al (2006) reported that male G. calmariensis and G. pusilla produce the same aggregation pheromone and is attractive to both species and both sexes. Atkinson and Shorrocks (1981) developed a model to help explain the coexistence of Drosophila spp.…”

Section: Adult and Larval Feedingmentioning

confidence: 99%

“…However, in Oregon G. pusilla was reported to be more abundant than G. calmariensis (Schooler, 1998). Also, at two sites near Chicago, Illinois based on pheromone trapping one site is dominated by G. calmariensis (76%) and the other site by G. pusilla (88%) (Bartelt et al, 2006). McAvoy et al (1997) reported both species present 3 years after release in Virginia.…”

Section: Adult and Larval Feedingmentioning

confidence: 99%

“…Competition, either inter or intraspecific, may have only a minor effect on coexistence. With both species producing and attracted to the same aggregation compound (Bartelt et al, 2006) it appears that there has been little evolutionary pressure for reproductive isolation. It is possible that these two Galerucella species coexist and have little impact on each other when food is abundant due to their similar developmental rates.…”

Section: Adult and Larval Feedingmentioning

confidence: 99%

See 1 more Smart Citation

Fecundity and feeding of Galerucella calmariensis and G. pusilla on Lythrum salicaria

McAvoy

Kok

2006

BioControl

View full text Add to dashboard Cite

Fecundity and feeding of two introduced sibling biological control species, Galerucella calmariensis and G. pusilla (Coleoptera: Chrysomelidae) on purple loosestrife, Lythrum salicaria L. (Lythraceae) were compared at constant temperatures of 12.5, 15, 20, 25, and 27.5°C. Larval feeding was also carried out at 30°C, but at this temperature, larvae developed only to the L2 stage and none pupated. Thus, data for this temperature were not used in the analysis. There were significant species Â temperature interactions in fecundity. Of the two species, Galerucella pusilla laid more eggs. Although egg production of both species was lowest at 12.5°C and increased to 20°C, at higher temperatures, the two species reacted differently. From 25 to 27.5°C, egg production decreased for G. pusilla, but G. calmariensis fecundity peaked at 27.5°C. Significant temperature Â species Â life-stage interactions were also observed in feeding. For each species, the amount of feeding varied with temperature and stage of development. Galerucella pusilla adults consumed more foliage at 15, 20, and 27.5°C. However, at 12.5°C G. calmariensis adults fed more than G. pusilla. G. pusilla larvae consumed an average of 25% less foliage than G. calmariensis. The lower larval consumption of G. pusilla suggests that when food is limited, G. pusilla larvae may have a higher survival rate because of its ability to complete larval development with less food and produce more progeny due to its greater fecundity. When food is not limited neither species would have a competitive advantage and both species could coexist temporally and spatially. However, since G. calmariensis larvae consumed more leaf material, the larval stage of this species would have a greater impact on purple loosestrife than G. pusilla.

show abstract

Dimethylfuran-Lactone Pheromone from Males of Galerucella calmariensis and Galerucella pusilla

Cited by 28 publications

References 32 publications

Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

Furan fatty acid as an anti-inflammatory component from the green-lipped mussel Perna canaliculus

Male Phyllotreta striolata (F.) Produce an Aggregation Pheromone: Identification of Male-specific compounds and Interaction with Host Plant Volatiles

Fecundity and feeding of Galerucella calmariensis and G. pusilla on Lythrum salicaria

Contact Info

Product

Resources

About