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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)


CROSBI ID: 346962 Za ispravke kontaktirajte CROSBI podršku putem web obrasca

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


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

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

Poveznice na cjeloviti tekst rada:

doi pubs.acs.org

Citiraj ovu publikaciju:

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)
Mastelić, J., Jerković, I., Blažević, I., Poljak-Blaži, M., Borović, S., Ivančić-Baće, I., Smrečki, V., Žarković, N., Brčić-Kostić, K., Vikić-Topić, D. & Mueller, N. (2008) A comparative study on the antioxidant and biological activities of carvacrol, thymol and eugenol derivatives. Journal of agricultural and food chemistry, 56 (11), 3989-3996 doi:10.1021/jf073272v.
@article{article, author = {Masteli\'{c}, Josip and Jerkovi\'{c}, Igor and Bla\v{z}evi\'{c}, Ivica and Poljak-Bla\v{z}i, Marija and Borovi\'{c}, Suzana and Ivan\v{c}i\'{c}-Ba\'{c}e, Ivana and Smre\v{c}ki, Vilko and \v{Z}arkovi\'{c}, Neven and Br\v{c}i\'{c}-Kosti\'{c}, Krunoslav and Viki\'{c}-Topi\'{c}, Dra\v{z}en and Mueller, Norbert}, year = {2008}, pages = {3989-3996}, DOI = {10.1021/jf073272v}, keywords = {Carvacrol, eugenol, thymol, hydroxymethyl derivatives, diarylmethane derivative, antioxidant activity, antiproliferative activity, antimicrobial activity, antiyeast activity}, journal = {Journal of agricultural and food chemistry}, doi = {10.1021/jf073272v}, volume = {56}, number = {11}, issn = {0021-8561}, title = {A comparative study on the antioxidant and biological activities of carvacrol, thymol and eugenol derivatives}, keyword = {Carvacrol, eugenol, thymol, hydroxymethyl derivatives, diarylmethane derivative, antioxidant activity, antiproliferative activity, antimicrobial activity, antiyeast activity} }
@article{article, author = {Masteli\'{c}, Josip and Jerkovi\'{c}, Igor and Bla\v{z}evi\'{c}, Ivica and Poljak-Bla\v{z}i, Marija and Borovi\'{c}, Suzana and Ivan\v{c}i\'{c}-Ba\'{c}e, Ivana and Smre\v{c}ki, Vilko and \v{Z}arkovi\'{c}, Neven and Br\v{c}i\'{c}-Kosti\'{c}, Krunoslav and Viki\'{c}-Topi\'{c}, Dra\v{z}en and Mueller, Norbert}, year = {2008}, pages = {3989-3996}, DOI = {10.1021/jf073272v}, keywords = {Carvacrol, eugenol, thymol, hydroxymethyl derivatives, diarylmethane derivative, antioxidant activity, antiproliferative activity, antimicrobial activity, antiyeast activity}, journal = {Journal of agricultural and food chemistry}, doi = {10.1021/jf073272v}, volume = {56}, number = {11}, issn = {0021-8561}, title = {A comparative study on the antioxidant and biological activities of carvacrol, thymol and eugenol derivatives}, keyword = {Carvacrol, eugenol, thymol, hydroxymethyl derivatives, diarylmethane derivative, antioxidant activity, antiproliferative activity, antimicrobial activity, antiyeast activity} }

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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