Synthesis of Carlina Oxide Analogues and Evaluation of Their Insecticidal Efficacy and Cytotoxicity

Kód výsledku v IS VaVaI

<a href="https://www.isvavai.cz/riv?ss=detail&h=RIV%2F00027006%3A_____%2F23%3A10176204" target="_blank" >RIV/00027006:_____/23:10176204 - isvavai.cz</a>

Nalezeny alternativní kódy

RIV/60460709:41210/23:95567

Výsledek na webu

<a href="https://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.3c00137" target="_blank" >https://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.3c00137</a>

DOI - Digital Object Identifier

<a href="http://dx.doi.org/10.1021/acs.jnatprod.3c00137" target="_blank" >10.1021/acs.jnatprod.3c00137</a>

Jazyk výsledku

angličtina

Název v původním jazyce

Synthesis of Carlina Oxide Analogues and Evaluation of Their Insecticidal Efficacy and Cytotoxicity

Popis výsledku v původním jazyce

Compoundsisolated from botanical sources represent innovativeand promising alternatives to conventional insecticides. Carlina oxideis a compound isolated from Carlina acaulis L. (Asteraceae)essential oil (EO) with great potential as bioinsecticide, being effectiveon various arthropod vectors and agricultural pests, with moderatetoxicity on non-target species. Since the production from the wildsource is limited, there is the need of exploring new synthetic routesfor obtaining this compound and analogues with improved bioactivityand lower toxicity. Herein, the chemical synthesis of carlina oxideanalogues was developed. Their insecticidal activity was assessedon the vectors Musca domestica L. and Culexquinquefasciatus Say, and their cytotoxicity was evaluatedon a human keratinocyte cell line (HaCaT). The compounds&apos; activitywas compared with that of the natural counterparts EO and carlinaoxide. In housefly tests, the analogues were comparably effectiveto purified carlina oxide. In Cx. quinquefasciatus assays, the meta-chloro analogue provided a significantlyhigher efficacy (LC50 of 0.71 mu g mL(-1)) than the EO and carlina oxide (LC50 1.21 and 1.31 mu gmL(-1), respectively) and a better safety profilethan carlina oxide on keratinocytes. Overall, this study can openthe way to an agrochemical production of carlina oxide analogues employableas nature-inspired insecticides.

Název v anglickém jazyce

Synthesis of Carlina Oxide Analogues and Evaluation of Their Insecticidal Efficacy and Cytotoxicity

Popis výsledku anglicky

Compoundsisolated from botanical sources represent innovativeand promising alternatives to conventional insecticides. Carlina oxideis a compound isolated from Carlina acaulis L. (Asteraceae)essential oil (EO) with great potential as bioinsecticide, being effectiveon various arthropod vectors and agricultural pests, with moderatetoxicity on non-target species. Since the production from the wildsource is limited, there is the need of exploring new synthetic routesfor obtaining this compound and analogues with improved bioactivityand lower toxicity. Herein, the chemical synthesis of carlina oxideanalogues was developed. Their insecticidal activity was assessedon the vectors Musca domestica L. and Culexquinquefasciatus Say, and their cytotoxicity was evaluatedon a human keratinocyte cell line (HaCaT). The compounds&apos; activitywas compared with that of the natural counterparts EO and carlinaoxide. In housefly tests, the analogues were comparably effectiveto purified carlina oxide. In Cx. quinquefasciatus assays, the meta-chloro analogue provided a significantlyhigher efficacy (LC50 of 0.71 mu g mL(-1)) than the EO and carlina oxide (LC50 1.21 and 1.31 mu gmL(-1), respectively) and a better safety profilethan carlina oxide on keratinocytes. Overall, this study can openthe way to an agrochemical production of carlina oxide analogues employableas nature-inspired insecticides.

Druh

J_imp - Článek v periodiku v databázi Web of Science

CEP obor

—

OECD FORD obor

40106 - Agronomy, plant breeding and plant protection; (Agricultural biotechnology to be 4.4)

Projekt

—

Návaznosti

I - Institucionalni podpora na dlouhodoby koncepcni rozvoj vyzkumne organizace

Rok uplatnění

2023

Kód důvěrnosti údajů

S - Úplné a pravdivé údaje o projektu nepodléhají ochraně podle zvláštních právních předpisů

Název periodika

JOURNAL OF NATURAL PRODUCTS

ISSN

0163-3864

e-ISSN

—

Svazek periodika

86

Číslo periodika v rámci svazku

5

Stát vydavatele periodika

US - Spojené státy americké

Počet stran výsledku

10

Strana od-do

1307-1316

Kód UT WoS článku

001010970800001

EID výsledku v databázi Scopus

2-s2.0-85160457587