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

IF 1.5 4区 农林科学 Q2 ENTOMOLOGY
Kenji Nemoto, Hirosato Takikawa, Yusuke Ogura
{"title":"Syntheses of (+)-costic acid and structurally related eudesmane sesquiterpenoids and their biological evaluations as acaricidal agents against <i>Varroa destructor</i>.","authors":"Kenji Nemoto,&nbsp;Hirosato Takikawa,&nbsp;Yusuke Ogura","doi":"10.1584/jpestics.D23-029","DOIUrl":null,"url":null,"abstract":"<p><p>Synthesis of (+)-costic acid, isolated from <i>Dittrichia viscosa</i> (L.) W. Greuter as a natural acaricidal sesquiterpenoid, was achieved in 16 steps from (<i>R</i>)-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 <i>Varroa destructor</i>. Among them, (+)-costal especially exhibited potent acaricidal activity.</p>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":null,"pages":null},"PeriodicalIF":1.5000,"publicationDate":"2023-08-20","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://ftp.ncbi.nlm.nih.gov/pub/pmc/oa_pdf/a9/a4/jps-48-3-D23-029.PMC10513954.pdf","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Pesticide Science","FirstCategoryId":"97","ListUrlMain":"https://doi.org/10.1584/jpestics.D23-029","RegionNum":4,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"ENTOMOLOGY","Score":null,"Total":0}
引用次数: 0

Abstract

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.

Abstract Image

Abstract Image

Abstract Image

(+)-costic acid和结构相关的真结烷倍半萜类化合物的合成及其作为灭螨剂的生物学评价。
以(R)-香芹酮为原料,经16步反应合成了从粘氏Ditrichia viscosa(L.)W.Greuter中分离的天然杀螨倍半萜类化合物(+)-costic acid,总收率4.8%,关键步骤是硒醚的自由基环化以构建十氢萘骨架。还合成了其他结构相关的天然产物,(+)-costal、(+)-costol和(+)β-selinene。还对这四种天然产物和一些合成中间体的杀螨活性进行了评价。其中(+)-costal表现出较强的杀螨活性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
Journal of Pesticide Science
Journal of Pesticide Science 农林科学-昆虫学
CiteScore
4.30
自引率
4.20%
发文量
28
审稿时长
18-36 weeks
期刊介绍: The Journal of Pesticide Science publishes the results of original research regarding the chemistry and biochemistry of pesticides including bio-based materials. It also covers their metabolism, toxicology, environmental fate and formulation.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信