Juvenile hormone III skipped bisepoxide, not its stereoisomers, as a juvenile hormone of the bean bug Riptortus pedestris.
In: General and comparative endocrinology, Jg. 289 (2020-04-01), S. 113394
academicJournal
Zugriff:
Juvenile hormone (JH) plays a pivotal role in many aspects of insect physiology. Although its presence was first reported in a blood-sucking bug belonging to the suborder Heteroptera (true bugs), JH species in the group has long been controversial. Although some recent studies proposed a putative JH molecular species in several Heteropteran species, it is not conclusive because physicochemical analyses were insufficient in most cases. Here, we studied this issue with an ultraperformance liquid chromatography-tandem mass spectrometer (UPLC-MS/MS) equipped with C18 and chiral columns in the bean bug Riptortus pedestris (Heteroptera, Alydidae), in which the JH species has long been controversial. Although a recent study describes JHSB 3 as the major JH of this species, that finding was not conclusive because its chirality has not been clarified. In the present study, we detected methyl (2R,3S,10R)-2,3;10,11-bisepoxyfarnesoate, commonly named juvenile hormone III skipped bisepoxide (JHSB 3 ), in the culture media of the corpora cardiaca-corpus allatum (CC-CA) complex and in the hemolymph of this species by a chiral ultraperformance liquid chromatography- tandem mass spectrometer (UPLC-MS/MS). Other JHSB 3 stereoisomers were not detected. Topical application of JHSB 3 effectively averted diapause. These results indicate that JHSB 3 is the major JH of R. pedestris. The present study further revealed that JHSB 3 and its (2R,3S,10S) isomer are more potent than (2S,3R,10R) and (2S,3R,10S) isomers, which suggests that there is a significance to the configuration of the 2,3-epoxide moiety in JH action. We further found a supplemental significance to the configuration of the 10-position.
(Copyright © 2020 Elsevier Inc. All rights reserved.)
Titel: |
Juvenile hormone III skipped bisepoxide, not its stereoisomers, as a juvenile hormone of the bean bug Riptortus pedestris.
|
---|---|
Autor/in / Beteiligte Person: | Ando, Y ; Matsumoto, K ; Misaki, K ; Mano, G ; Shiga, S ; Numata, H ; Kotaki, T ; Shinada, T ; Goto, SG |
Zeitschrift: | General and comparative endocrinology, Jg. 289 (2020-04-01), S. 113394 |
Veröffentlichung: | New York, NY : Academic Press ; <i>Original Publication</i>: New York., 2020 |
Medientyp: | academicJournal |
ISSN: | 1095-6840 (electronic) |
DOI: | 10.1016/j.ygcen.2020.113394 |
Schlagwort: |
|
Sonstiges: |
|