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Syntheses of (+)-costic acid and structurally related eudesmane sesquiterpenoids and their biological evaluations as acaricidal agents against Varroa destructor

Synthesis of (+)-costic acid, isolated from Dittrichia viscosa (L.) W. Greuter as a natural acaricidal sesquiterpenoid, was achieved in 16 steps from (R)-carvone with an overall yield of 4.8%, involving the radical cyclization of selenoester to construct a decalone framework as the key step. Other s...

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Detalles Bibliográficos
Autores principales: Nemoto, Kenji, Takikawa, Hirosato, Ogura, Yusuke
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Pesticide Science Society of Japan 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10513954/
https://www.ncbi.nlm.nih.gov/pubmed/37745169
http://dx.doi.org/10.1584/jpestics.D23-029
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author Nemoto, Kenji
Takikawa, Hirosato
Ogura, Yusuke
author_facet Nemoto, Kenji
Takikawa, Hirosato
Ogura, Yusuke
author_sort Nemoto, Kenji
collection PubMed
description Synthesis of (+)-costic acid, isolated from Dittrichia viscosa (L.) W. Greuter as a natural acaricidal sesquiterpenoid, was achieved in 16 steps from (R)-carvone with an overall yield of 4.8%, involving the radical cyclization of selenoester to construct a decalone framework as the key step. Other structurally related natural products, (+)-costal, (+)-costol, and (+)-β-selinene, were also synthesized. The acaricidal activities of these four natural products and some synthetic intermediates were also evaluated against Varroa destructor. Among them, (+)-costal especially exhibited potent acaricidal activity.
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spelling pubmed-105139542023-09-23 Syntheses of (+)-costic acid and structurally related eudesmane sesquiterpenoids and their biological evaluations as acaricidal agents against Varroa destructor Nemoto, Kenji Takikawa, Hirosato Ogura, Yusuke J Pestic Sci Brief Report Synthesis of (+)-costic acid, isolated from Dittrichia viscosa (L.) W. Greuter as a natural acaricidal sesquiterpenoid, was achieved in 16 steps from (R)-carvone with an overall yield of 4.8%, involving the radical cyclization of selenoester to construct a decalone framework as the key step. Other structurally related natural products, (+)-costal, (+)-costol, and (+)-β-selinene, were also synthesized. The acaricidal activities of these four natural products and some synthetic intermediates were also evaluated against Varroa destructor. Among them, (+)-costal especially exhibited potent acaricidal activity. Pesticide Science Society of Japan 2023-08-20 /pmc/articles/PMC10513954/ /pubmed/37745169 http://dx.doi.org/10.1584/jpestics.D23-029 Text en © 2023 Pesticide Science Society of Japan https://creativecommons.org/licenses/by-nc-nd/4.0/This is an open access article distributed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International (CC BY-NC-ND 4.0) License.
spellingShingle Brief Report
Nemoto, Kenji
Takikawa, Hirosato
Ogura, Yusuke
Syntheses of (+)-costic acid and structurally related eudesmane sesquiterpenoids and their biological evaluations as acaricidal agents against Varroa destructor
title Syntheses of (+)-costic acid and structurally related eudesmane sesquiterpenoids and their biological evaluations as acaricidal agents against Varroa destructor
title_full Syntheses of (+)-costic acid and structurally related eudesmane sesquiterpenoids and their biological evaluations as acaricidal agents against Varroa destructor
title_fullStr Syntheses of (+)-costic acid and structurally related eudesmane sesquiterpenoids and their biological evaluations as acaricidal agents against Varroa destructor
title_full_unstemmed Syntheses of (+)-costic acid and structurally related eudesmane sesquiterpenoids and their biological evaluations as acaricidal agents against Varroa destructor
title_short Syntheses of (+)-costic acid and structurally related eudesmane sesquiterpenoids and their biological evaluations as acaricidal agents against Varroa destructor
title_sort syntheses of (+)-costic acid and structurally related eudesmane sesquiterpenoids and their biological evaluations as acaricidal agents against varroa destructor
topic Brief Report
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10513954/
https://www.ncbi.nlm.nih.gov/pubmed/37745169
http://dx.doi.org/10.1584/jpestics.D23-029
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