Identification of a sex pheromone component of the Japanese mealybug, Planococcus kraunhiae (Kuwana)

Sugie, Hajime; Teshiba, Mayumi; Narai, Yutaka; Tsutsumi, Takafumi; Sawamura, Nobuo; Tabata, Jun; Hiradate, Syuntaro

doi:10.1303/aez.2008.369

Cited by 39 publications

(12 citation statements)

References 20 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Sex pheromones of Pseudococcus cryptus (Arai et al 2003) and P. citri (BierlLeonhardt et al 1981) are monoterpenes with a cyclobutane moiety. The sex pheromone of P. ficus (Hinkens et al 2001), P. minor (Ho et al 2007), and P. kraunhiae (Kuwana) (Sugie et al 2008) are acyclic monoterpenes with the same basic carbon skeleton formed from an unusual linkage of two isoprene units. All of the species mentioned above appear to use single components as attractants.…”

Section: Discussionmentioning

confidence: 99%

“…Sex pheromones of the related species Planococcus citri (Risso) and Planococcus ficus Signoret have been identified, and now are widely used in pest management (Moreno et al 1984;Millar et al 2002;Walton et al 2006). Sex pheromones of several other mealybug species have been identified recently, including Pseudococcus maritimus (Ehrhorn) (Figadere et al 2007), Planococcus minor (Maskell) (Ho et al 2007), and Planococcus kraunhiae (Kuwana) (Sugie et al 2008). For a pest as important as P. madeirensis, identification of the sex pheromone for use in pheromone-baited monitoring traps would be helpful for detection and management.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Identification and Synthesis of the Sex Pheromone of the Madeira Mealybug, Phenacoccus Madeirensis Green

Ho¹,

Su²,

Chi-Hung³

et al. 2009

J Chem Ecol

View full text Add to dashboard Cite

Two components were identified from aeration extracts of the virgin female Madeira mealybug, Phenacoccus madeirensis as trans-(1R,3R)-chrysanthemyl (R)-2-methylbutanoate and (R)-lavandulyl (R)-2-methylbutanoate (with a ratio of 3:1) by a combination of gas chromatography retention time matches, mass spectrometry, and microchemical tests. The structures and chirality of the compounds were confirmed by comparing with synthetic compounds. The synthetic trans-(1R,3R)-chrysanthemyl (R)-2-methylbutanoate was highly attractive to males in laboratory bioassays; the synthetic (R)-lavandulyl (R)-2-methylbutanoate was weakly attractive. No synergistic effect was observed when the mixture of the two compounds was tested.

show abstract

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Identification and Synthesis of the Sex Pheromone of the Madeira Mealybug, Phenacoccus Madeirensis Green

Ho¹,

Su²,

Chi-Hung³

et al. 2009

J Chem Ecol

View full text Add to dashboard Cite

show abstract

“…A. pisum and P. kraunhiae were supplied by the National Institute of Advanced Industrial Science and Technology (AIST) 12) and the Fukuoka Agriculture and Forestry Research Center, 13) respectively.…”

Section: Insectsmentioning

confidence: 99%

Characterization of two adenine nucleotide translocase paralogues in the stink bug, <i>Plautia stali</i>

et al. 2016

View full text Add to dashboard Cite

Adenine nucleotide translocase (ANT) is a nuclear-coded mitochondrial protein that exchanges ATP for ADP across the mitochondrial inner membrane. Most organisms possess several ANT paralogues, and functional differences among these paralogues remain largely unknown. In the present study, we identified ANT paralogue genes in hemipteran species: the stink bug, bean bug, pea aphid, and Japanese mealybug. The ANT paralogues of the stink bug, Plautia stali, are encoded by two genes, PsANTI1 and PsANTI2. PsANTI1 was constantly expressed at all developmental stages and in all tissues analyzed. In contrast, the expression levels of PsANTI2 were undetectable in first instar nymphs and adult antennae. Gene silencing of each paralogue in P. stali revealed that PsANTI1 plays an important role in homeostasis, whereas the depletion of PsANTI2 failed to result in lethality. Thus, we concluded that PsANTI1 is a good target gene for developing novel pesticides.

show abstract

“…Moreover, five of the alcohols are lavandulol, and three others have the same skeleton as lavandulol (Fig. 5;De Alfonso et al 2012;Hinkens et al 2001;Ho et al 2007Ho et al , 2009Sugie et al 2008;Zhang et al 2004). Thus, lavandulol appears to be a key motif in mealybug pheromones.…”

Section: Discussionmentioning

confidence: 99%

“…As we noted previously, lavandulol has an unusual non-head-to-tail connection of isoprene units. (Ho et al 2007) Planococcus kraunhiae (Sugie et al 2008) Planococcus ficus (Hinkens et al 2001) Maconellicoccus hirsutus (Zhang et al 2004) Thus, mealybugs may have a common biosynthetic mechanism to connect isoprene units in a different manner from general monoterpene biosynthesis in other organisms. We started the synthesis of compound (4) from a symmetric dicarboxylic ester, diethyl isopropylmalonate, which was reduced to a 1,3-diol (1) and mono-acetylated to monohydroxyacetate (2) using dimethyltin(IV) dichloride as a catalyst (Muramatsu et al 2012).…”

Section: Discussionmentioning

confidence: 99%

A New Lavandulol-related Monoterpene in the Sex Pheromone of the Grey Pineapple Mealybug, Dysmicoccus neobrevipes

Tabata

Ichiki

2015

J Chem Ecol

Self Cite

View full text Add to dashboard Cite

The grey pineapple mealybug, Dysmicoccus neobrevipes, is a serious pest that attacks a variety of crops in tropical regions. Recently, it was recorded on an island in southwestern Japan, suggesting that its distribution is expanding. As a measure against this expansion, a monitoring tool is urgently needed. In this study we determined the structure of the sex pheromone of D. neobrevipes in order to develop an efficient lure for monitoring traps. Volatiles collected from virgin adult females were fractionated by high performance liquid chromatography (HPLC) and gas chromatography, and fractions were tested for attractiveness to males in a laboratory bioassay. A single compound was isolated which was as attractive to males as the crude collections, and this was proposed to be the main, if not the only, component of the female-produced sex pheromone. The structure of this was determined to be (E)-2-isopropyl-5-methylhexa-3,5-dienyl acetate by gas chromatography/mass spectrometry and nuclear magnetic resonance analyses. This compound was synthesized through four steps, and the synthetic chemical was as attractive as the natural product in a greenhouse bioassay. The enantiomers of the synthetic acetate were obtained by enantioselective HPLC fractionation of the corresponding alcohols, and the natural pheromone was shown to be the (+)-isomer. The carbon skeleton of this novel compound is related to lavandulol, a monoterpene with an unusual non-head-to-tail connection of isoprene units that is often found in mealybug pheromones.

show abstract

Identification of a sex pheromone component of the Japanese mealybug, Planococcus kraunhiae (Kuwana)

Cited by 39 publications

References 20 publications

Identification and Synthesis of the Sex Pheromone of the Madeira Mealybug, Phenacoccus Madeirensis Green

Identification and Synthesis of the Sex Pheromone of the Madeira Mealybug, Phenacoccus Madeirensis Green

Characterization of two adenine nucleotide translocase paralogues in the stink bug, <i>Plautia stali</i>

A New Lavandulol-related Monoterpene in the Sex Pheromone of the Grey Pineapple Mealybug, Dysmicoccus neobrevipes

Contact Info

Product

Resources

About