Structure Determination of a Natural Juvenile Hormone Isolated from a Heteropteran Insect

Abstract

Juvenile hormone (JH), which occurs in several forms in different insects, is one of the most important insect hormones. The structure of JH in Heteroptera has not been elucidated until recently, although insects in this suborder have long been used as experimental animals for JH research. Here we review the structure determination of a novel JH in a stink bug,Plautia stali, which was named juvenile hormone III skipped bisepoxide [JHSB3: methyl (2R,3S,10R)-2,3;10,11-bisepoxyfarnesoate], based on the arrangement of two epoxides at C2,3 and C10,11 with a skipped double bond at C6,7.

The Juvenile Hormone Receptor and Molecular Mechanisms of Juvenile Hormone Action

“…However, only JH II and JH III were found to initiate patency through a pathway involving PKC and Na þ /K þ ATPase similar to reports in Locusta and Rhodnius, while JH I utilizes a distinct pathway involving protein kinase A and cAMP (Pszczolkowski et al, 2005(Pszczolkowski et al, , 2008. On the other hand, recent studies in the stink bug Plautia stali (Kotaki et al, 2009(Kotaki et al, , 2012 suggest that JHSB 3 , not JH I, may be the principal JH produced in hemipteran species including Rhodnius. A similar issue arises concerning studies of Rhodnius, where out of three related forms-JH I, JH II and JH III-only JH I was able to induce patency in an in vitro assay (Ilenchuk and Davey, 1987).…”

“…The most common JH among insects is JH III (methyl 10,11-epoxyfarnesoate), while Lepidoptera possess JH 0, JH I and JH II as well as JH III (Baker, 1990;Furuta et al, 2013;Schooley et al, 1984). In Hemiptera, the compound JH skipped bisepoxy ( JHSB 3 ) appears to be the predominant JH (Kotaki et al, 2009(Kotaki et al, , 2012. 4.1).…”

Precise Regulation of Juvenile Hormone III R-Stereoisomer Synthesis by Apis mellifera through Specifically Binding Methyl-(2E,6E)-farnesoate and Strictly Controlling Its Titer

“…13 Among the seven major forms identified based on the side chain length and epoxidation position (JH 0, JH I, JH II, JH III, 4-methyl-JH I, JHB 3 , and JHSB 3 ), juvenile hormone III (JH III) is the most widely distributed insect homologue. 14 In nature, two absolute JH III optical enantiomers configurations exist: the R (R-JH III) and S (S-JH III) stereoisomers. 15−18 However, according to Yi et al, only R-JH III without S-JH III has been reported in 26 insects.…”

Juvenile Hormone III R Stereoisomer Is Specifically Synthesized by Honeybees (Apis mellifera ligustica) and Shows a Higher Biological Activity in Regulating Their Social Behavior

“…JH is synthesized in and secreted from the corpora allata . Seven different JHs in insects have been confirmed, and JH plays a crucial role in the metamorphosis, caste differentiation, and migration of insects . They also regulate vitellogenesis, reproduction, and ovary development .…”