Action of six pyrethrins purified from the botanical insecticide pyrethrum on cockroach sodium channels expressed in Xenopus oocytes

Pyrethrin I, pyrethrin II, cinerin I, cinerin II, jasmolin I and jasmolin II are six closely related insecticidal active esters, known as pyrethrins, found in the pyrethrum extract from the dry flowers of Tanacetum cinerariifolium. The chemical structures of the six compounds differ only in the term...

Full description

Saved in:
Bibliographic Details
Published inPesticide biochemistry and physiology Vol. 151; pp. 82 - 89
Main Authors Chen, Mengli, Du, Yuzhe, Zhu, Guonian, Takamatsu, Genki, Ihara, Makoto, Matsuda, Kazuhiko, Zhorov, Boris S., Dong, Ke
Format Journal Article
LanguageEnglish
Published United States Elsevier Inc 01.10.2018
Subjects
Online AccessGet full text

Cover

Loading…
More Information
Summary:Pyrethrin I, pyrethrin II, cinerin I, cinerin II, jasmolin I and jasmolin II are six closely related insecticidal active esters, known as pyrethrins, found in the pyrethrum extract from the dry flowers of Tanacetum cinerariifolium. The chemical structures of the six compounds differ only in the terminal moieties at the acid and alcohol ends, but the compounds' in vivo toxicities are substantially different. Pyrethrins are lead compounds for pyrethroids, a large family of synthetic insecticides that alter nerve functions by prolonging the opening of voltage-gated sodium channels. However, data on the mechanism of action of natural pyrethrins are very limited. In this study, we examined the actions of all six pyrethrins on cockroach sodium channels expressed in Xenopus oocytes. Although the six compounds showed comparable potencies in inhibiting the inactivation of sodium channels, they had greatly variable potencies in inhibiting channel deactivation. Furthermore, unlike pyrethroids, the action of pyrethrins neither depend on nor were enhanced by repeated channel activation. We created a NavMs-based model of the cockroach sodium channel, in which pyrethrin II was docked at the pyrethroid receptor site 1 (PyR1), and proposed a rationale for the observed structure-activity relationship of the six pyrethrins. Our study sheds light on the molecular mechanism of pyrethrum action on sodium channels and reveled differences in the modes of action of the six bioactive constitutes of pyrethrum. [Display omitted] •All six constituents of pyrethrum inhibited inactivation and deactivation of a cockroach sodium channel•All six compounds caused similar degrees of inhibition of channel inactivation•Pyrethrin II was the most potent in inhibiting channel deactivation.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0048-3575
1095-9939
DOI:10.1016/j.pestbp.2018.05.002