Male-Produced Sex Pheromone of Tibraca limbativentris Revisited: Absolute Configurations of Zingiberenol Stereoisomers and their Influence on Chemotaxis Behavior of Conspecific Females

Blassioli‐Moraes, Maria Carolina; Khrimian, Ashot; Michereff, Mirian Fernandes Furtado; Magalhães, Diego Martins; Hickel, Eduardo Rodrigues; Freitas, Thais Fernanda Stella de; Barrigossi, J.A.F.; Laumann, R. A.; Silva, A T; Guggilapu, Sravanthi Devi; Silva, C C; Sant’Ana, Josué; Borges, Miguel

doi:10.1007/s10886-019-01125-w

Cited by 9 publications

(17 citation statements)

References 24 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Sex pheromones comprise sex attractant pheromones, which induce upwind oriented movements to the conspecific individual, and courtship pheromones, which elicit a variety of close-range responses in the insect partner [ 12 , 13 ]. Since the first pheromone discovery, the rapid progress of methodologies developed to identify new pheromones, mainly GC, GC-MS, NMR, electrophysiological techniques [electroantennography (EAG), gas chromatography coupled to electroantennography (GC-EAD), single sensillum recordings (SSR), and coupled GC-SSR], have allowed the identification of thousands of compounds as insect sex pheromones [ 14 ] ( Table 2 contains new sex pheromones and sex pheromone components recently identified from insect pests in the period 2010–2020 and the corresponding references [ 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 , 28 , 29 , 30 , 31 , 32 ]). In addition, an interdisciplinary approach involving advances in analytical chemistry, neurophysiology, genetics, and molecular biology have improved our understanding of insect chemical communication and behavior to the level of discrete neural circuits [ 8 ].…”

Section: Introductionmentioning

confidence: 99%

Latest Developments in Insect Sex Pheromone Research and Its Application in Agricultural Pest Management

Rizvi

George

Reddy

et al. 2021

Insects

View full text Add to dashboard Cite

Since the first identification of the silkworm moth sex pheromone in 1959, significant research has been reported on identifying and unravelling the sex pheromone mechanisms of hundreds of insect species. In the past two decades, the number of research studies on new insect pheromones, pheromone biosynthesis, mode of action, peripheral olfactory and neural mechanisms, and their practical applications in Integrated Pest Management has increased dramatically. An interdisciplinary approach that uses the advances and new techniques in analytical chemistry, chemical ecology, neurophysiology, genetics, and evolutionary and molecular biology has helped us to better understand the pheromone perception mechanisms and its practical application in agricultural pest management. In this review, we present the most recent developments in pheromone research and its application in the past two decades.

show abstract

Section: Introductionmentioning

confidence: 99%

Latest Developments in Insect Sex Pheromone Research and Its Application in Agricultural Pest Management

Rizvi

George

Reddy

et al. 2021

Insects

View full text Add to dashboard Cite

show abstract

“…Two main pheromone components of T. limbativentris, RSR - and SSR -zingiberenols, were identified earlier …”

Section: Resultsmentioning

confidence: 98%

“…Having all stereoisomers of sesquipiperitol in hand, we developed a chiral-phase gas-chromatography method to expedite assignment of absolute configurations of sesquipiperitols in rice stalk stink bugs, T. limbativentris, pheromone collection and possibly other natural sources. Figure A shows a gas-chromatogram of a mixture of all sesquipiperitol stereoisomers on a Lipodex G column where only a pair of enantiomers 4 and 9 were not separated.…”

Section: Resultsmentioning

confidence: 99%

“… It was shown that an enzyme unrelated to plant and microbial terpene synthases catalyzes conversion of ( E , E )-farnesyl diphosphate to (1 S ,6 S ,7 R )-2,10-bisaboladien-1-ol ( SSR -sesquipiperitol) . More recently, we identified sesquipiperitol as a minor component of the rice stink bug, Tibraca limbativentris, male-produced sex pheromone . Because the main pheromone component in T.…”

mentioning

confidence: 99%

“…Because the main pheromone component in T. limbativentris was a structurally related zingiberenol (Figure ), , it is conceivable that here sesquipiperitol has a dual role: a pheromone and an intermediate in the biosynthesis of another pheromone component. Only two diastereomers of sesquipiperitol have been stereochemically characterized thus far .…”

mentioning

confidence: 99%

See 2 more Smart Citations

Absolute Configurations of Stink Bug- and Plant-Produced Sesquipiperitols via Synthesis of All Stereoisomers

et al. 2020

View full text Add to dashboard Cite

Sesquipiperitol is a sesquiterpene alcohol, some stereoisomers of which were found in several plant species. The biological role of these compounds in plants and their absolute configurations have not been reported. Recently, we found that 1S,6S,7R stereoisomer of sesquipiperitol was a key precursor in the biosynthesis of the harlequin bug, Murgantia histrionica, pheromone, which consists of two stereoisomeric zingiberenol oxides. In addition, the Tibraca limbativentris stink bug was shown to produce two sesquipiperitol stereoisomers as minor components in their male-produced sex pheromone, the main constituents of which were zingiberenols. To determine absolute configurations of plant-and stink-bugproduced sesquipiperitols, we undertook syntheses of all stereoisomers of this sesquiterpene alcohol. The syntheses were based on 1,10-bisaboladien-3-ols (aka zingiberenols) with known configurations at C-6 and C-7, the oxidation of which provided sesquipiperitone precursors with retention of configurations of these stereogenic centers. The foremost challenge of the synthetic endeavor was the assignment of absolute configurations of secondary carbinol centers, which was resolved by NMR analyses of corresponding Mosher's esters. Thus, the availability of all eight diastereomers allowed us to assign sesquipiperitols from Fitzroya cupressoides and Argyranthemum adauctum spp. jacobaeifolium plants 1S,6S,7R (16) and 1R,6R,7S (14) configurations, respectively. A chiral-phase gaschromatographic method was developed to determine 1S,6S,7R and 1R,6S,7R (15) configurations of T. limbativentris sesquipiperitol pheromone components.

show abstract

Deciphering the Absolute Configuration of Murgantiol Isomers in the Pheromone Blend of the Rice Stink Bug, Mormidea v‐luteum (Hemiptera, Pentatomidae)

Souza,

Melo,

Moliterno

et al. 2024

Chemistry & Biodiversity

View full text Add to dashboard Cite

The males‐produced pheromone blend of the Mormidea v‐luteum (Hemiptera, Pentatomidae) consists in two isomers of zingiberenol (1) and three of murgantiol (2). While the absolute configuration of the zingiberenol isomers has been described, the configurations of the murgantiol isomers remained unexplored. So, our objective was to identify the absolute configuration of the murgantiol isomers (2a‐c) in the pheromone blend. To achieve this, we initially performed dehydration of the natural extract followed by enantiomeric resolution and, as a result, the three isomers was identified as (4R,1'S)‐murgantiol. By leveraging the fixed cis and trans relationships among all pheromone components, we established the configuration at C‐1 for isomers 2a and 2b is S, while that of 2c is R. Finally, employing microchemical Sharples asymmetric dihydroxylation and epoxide ring closure, we determined the absolute configuration of the epoxide ring. Consequently, the natural isomers 2a, 2b, and 2c were identified as (1S,4R,1'S,4'R)‐, (1S,4R,1'S,4'S)‐, and (1R,4R,1'S,4'S)‐murgantiol, respectively.

show abstract

Male-Produced Sex Pheromone of Tibraca limbativentris Revisited: Absolute Configurations of Zingiberenol Stereoisomers and their Influence on Chemotaxis Behavior of Conspecific Females

Cited by 9 publications

References 24 publications

Latest Developments in Insect Sex Pheromone Research and Its Application in Agricultural Pest Management

Latest Developments in Insect Sex Pheromone Research and Its Application in Agricultural Pest Management

Absolute Configurations of Stink Bug- and Plant-Produced Sesquipiperitols via Synthesis of All Stereoisomers

Deciphering the Absolute Configuration of Murgantiol Isomers in the Pheromone Blend of the Rice Stink Bug, Mormidea v‐luteum (Hemiptera, Pentatomidae)

Contact Info

Product

Resources

About