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Pregled bibliografske jedinice broj: 346962

A comparative study on the antioxidant and biological activities of carvacrol, thymol and eugenol derivatives


Mastelić, Josip; Jerković, Igor; Blažević, Ivica; Poljak-Blaži, Marija; Borović, Suzana; Ivančić-Baće, Ivana; Smrečki, Vilko; Žarković, Neven; Brčić-Kostić, Krunoslav; Vikić-Topić, Dražen; Mueller, Norbert
A comparative study on the antioxidant and biological activities of carvacrol, thymol and eugenol derivatives // Journal of agricultural and food chemistry, 56 (2008), 11; 3989-3996 doi:10.1021/jf073272v (međunarodna recenzija, članak, znanstveni)


Naslov
A comparative study on the antioxidant and biological activities of carvacrol, thymol and eugenol derivatives

Autori
Mastelić, Josip ; Jerković, Igor ; Blažević, Ivica ; Poljak-Blaži, Marija ; Borović, Suzana ; Ivančić-Baće, Ivana ; Smrečki, Vilko ; Žarković, Neven ; Brčić-Kostić, Krunoslav ; Vikić-Topić, Dražen ; Mueller, Norbert

Izvornik
Journal of agricultural and food chemistry (0021-8561) 56 (2008), 11; 3989-3996

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
Carvacrol; eugenol; thymol; hydroxymethyl derivatives; diarylmethane derivative; antioxidant activity; antiproliferative activity; antimicrobial activity; antiyeast activity

Sažetak
Four derivatives of thymol, carvacrol, and eugenol were synthesized: 4-(hydroxymethyl)-5-isopropyl- 2-methylphenol, 4, 4′ -methylenebis(5-isopropyl-2-methyl)phenol, 4-allyl-6-(hydroxymethyl)-2-methox- yphenol, and 4-(hydroxymethyl)-2-isopropyl-5-methylphenol. The obtained derivatives showed remarkably better antioxidative properties according to 1, 1-diphenyl-2-picrylhydrazyl assay (50% inhibitory concentrations ) 4– 156 µ ; g/mL) and Rancimat assay (protection factors ) 1.55– 5.84) when compared with parent compounds and values similar to or better than those of butylated hydroxy- toluene and vitamin C. At concentrations of 10 mM carvacrol derivatives had no toxic effect on viability of Escherichia coli K-12 (determined by minimum inhibitory concentrations). Other phenol derivatives showed reduced cytotoxic effect on E. coli K-12 at concentrations of 2– 5 mM on the basis of 50% lethal dose measurements. In comparison with the parent compounds, phenol derivatives showed reduced cytotoxic effect for Saccharomyces cerevisiae cells (determined by yeast colony reduction). On the other hand, the majority of synthesized compounds had dose-dependent antiproliferative effects on human uterine carcinoma cells (HeLa), which makes them potentially interesting for the adjuvant experimental cancer treatments. The 4, 4′ -methylenebis(5-isopropyl-2-methyl)phenol derivative of carvacrol showed lower inhibiting capacity also for the HeLa cells, which makes this particular derivative attractive as an effi cient antioxidant with negligible cytotoxic effects.

Izvorni jezik
Engleski

Znanstvena područja
Kemija, Biologija, Temeljne medicinske znanosti



POVEZANOST RADA


Projekt / tema
011-0982929-1329 - Eterična ulja i arome-biološki aktivni spojevi i njihove modifikacije (Ani Radonić, )
098-0982464-2519 - Lipidi, slobodni radikali i njihovi glasnici u integrativnoj onkologiji (Neven Žarković, )
098-0982913-2867 - Uloga rekombinacije u popravku DNA i evoluciji genoma (Krunoslav Brčić-Kostić, )
098-0982929-2917 - Spektroskopija NMR i modeliranje bioaktivnih molekula (Dejan Plavšić, )
108-0000000-0028 - Oksidacijski stres i tumori središnjeg živčanog sustava (Kamelija Žarković, )
108-0532264-0048 - Hepatocelularni tumori (Marijana Ćorić, )
119-1191196-1201 - Organizacija, funkcija i mehanizmi evolucije biljnog genoma (Višnja Besendorfer, )

Ustanove
Kemijsko-tehnološki fakultet, Split,
Institut "Ruđer Bošković", Zagreb,
Medicinski fakultet, Zagreb,
Prirodoslovno-matematički fakultet, Zagreb

Časopis indeksira:


  • Current Contents Connect (CCC)
  • Web of Science Core Collection (WoSCC)
    • Science Citation Index Expanded (SCI-EXP)
    • SCI-EXP, SSCI i/ili A&HCI
  • Scopus


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