Milka Maksimovic - Academia.edu (original) (raw)
Papers by Milka Maksimovic
Journal of Enzyme Inhibition and Medicinal Chemistry, 2016
The effect of Ca(2+) ions on the cytotoxic ability of boron heterocyclic compound dipotassium-tri... more The effect of Ca(2+) ions on the cytotoxic ability of boron heterocyclic compound dipotassium-trioxohydroxytetrafluorotriborate (K2[B3O3F4OH]), on in vitro tumor cells (mammary adenocarcinoma 4T1, melanoma B16F10 and squamous cell carcinoma SCCVII) and non-tumoral fibroblast cells (mouse dermal L929 and hamster lung V79) was examined. At small concentrations of Ca(2+) ions (0.42 mM), K2[B3O3F4OH] (3.85 mM) has a very strong cytotoxic effect on all cancer cells tested (89.1, 85.6 and 84.6%) and significantly less effect on normal cells (19.5 and 24.2%), respectively. Applying larger concentrations of Ca(2+) ions (9.42-72.42 mM), at the same concentration of K2[B3O3F4OH], no significant cytotoxic effect was detected on cancer cells and normal cells investigated. The selective ability of K2[B3O3F4OH], in the medium with a low concentration of Ca(2+) ions has a strong cytotoxic effect on cancer cells and very weak effect in normal cells, opens up the possibility of its application in antitumor therapy.
Analytical Chemistry Letters, Mar 7, 2013
ABSTRACT
Food Chemistry, Nov 1, 2009
A series of selected 4-methylcoumarins (4-methyl-2H-1-benzopyran-2-ones) were synthesised and tes... more A series of selected 4-methylcoumarins (4-methyl-2H-1-benzopyran-2-ones) were synthesised and tested for radical-scavenging ability using the stable 1,1-diphenyl-2-picrylhydrazyl radical, and for reducing power ability with a test based on the reduction of ferric to ferrous cation. All studied compounds showed activity comparable to Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid), an already known antioxidant, which is used as standard in most of the testing methods. Observations from the study were made with regard to structural features that regulated the behaviour of the compounds. The antioxidant activity of some 4-methylcoumarin representatives is presented here for the first time and extends our knowledge of the range of valuable biological activities and possible roles in therapy and for food preservation associated with this group of compounds.
Http Dx Doi Org 10 1080 0972060x 2009 10643720, Mar 12, 2013
Satureja is a genus of the well-known medicinal plants of Lamiaceae family that comprises numerou... more Satureja is a genus of the well-known medicinal plants of Lamiaceae family that comprises numerous species growing wild in the Mediterranean area. The essential oils of Satureja visianii Šilic and Satureja montana L., growing together at the same habitat under similar environmental conditions, were subjected to detailed gas chromatography-mass spectrometry analysis in order to compare their chemical composition. S. visianii Šilic is a stenoendemic species with narrow geographical distribution limited to only one locality, Pelješac Peninsula in Croatia. More than one hundred twenty compounds were identified in both plant oils representing 90.4 % -99.5 % of the total oil. The most abundant components in S. visianii essential oil were viridiflorol (17.9 %), borneol (12.6 %) and camphor (6.5 %), while S. montana oil was rich in phenolic compounds carvacrol (59.1 %) and thymol (20.1 %).
Pharmaceutical Biology, May 23, 2015
Stachys menthifolia Vis. (Lamiaceae) is an endemic species from the Balkan Peninsula spread throu... more Stachys menthifolia Vis. (Lamiaceae) is an endemic species from the Balkan Peninsula spread throughout Albania, Greece, Montenegro, and Croatia. This article presents the first investigation of the essential oil composition of this species from Croatia. Aerial parts of the plant were collected from three different natural habitats in the region of Biokovo Mountain. The studied populations showed similarity in qualitative, but not in quantitative, composition of their essential oils. Hydrodistilled volatile oil obtained from the plant material of S. menthifolia was subjected to gas chromatographic analysis coupled to mass spectrometry. More than 100 compounds were identified in the three samples, representing 86.8-90.8% of the total oil. The terpene profile of S. menthifolia is characterized by a high content of oxygenated sesquiterpenes (48.4-58.9%) and diterpene hydrocarbons (3.5-25.2%), with 8-α-acetoxyelemol (6.9-21.3%), abietatriene (3.5-21.1%), and 4'-methoxyacetophenone (4.5-17.0%) as the main constituents.
Chemistry & Biodiversity
Essential-oil profile of Salvia brachyodon Vandas, an endemic Dinaric species transferred from Ad... more Essential-oil profile of Salvia brachyodon Vandas, an endemic Dinaric species transferred from Adriatic Coast to the continental climatic conditions, was determined. Hydrodistilled oils obtained from the plant material collected in three-year field trial were subjected to the detailed GC/MS analysis. Hundred and fifty volatile compounds were identified in four samples. Comparison of the chemical composition of the isolated essential oils showed that population collected one year after transfer preserved sesquiterpene character of its oil (74.3%), while all subsequent samples gave the oils of monoterpene type with 1,8-cineole as the principal constituent (22.2 -42.3%). The high degree of variation in the qualitative and quantitative composition of the volatile constituents revealed the strong influence of environmental conditions on the nature of plant chemical composition that has an important role in a plant adaptation.
Ćavar, S., Maksimović, M., Šolić, M. E.: Comparison of Essential Oil Composition of Stachys menth... more Ćavar, S., Maksimović, M., Šolić, M. E.: Comparison of Essential Oil Composition of Stachys menthifolia Vis. from Two Natural Habitats in Croatia. Biologica Nyssana, 1 (1-2), December 2010: 99-103.
Natural product communications
Essential oil of Thymus aureopunctatus (Beck) K. Malý, obtained by hydrodistillation and headspac... more Essential oil of Thymus aureopunctatus (Beck) K. Malý, obtained by hydrodistillation and headspace technique, was subjected to capillary GC-MS analysis, and its volatile composition was compared with essential oil profile of Thymus serpyllum L. and a botanically undetermined thyme species, Thymus spp., all growing wild in the same habitat in Bosnia and Herzegovina. This paper presents the first report on phytochemical analysis of the rare T. aureopunctatus species, and also the first report on headspace analysis of plants belonging to the genus Thymus. One hundred and two volatile constituents were identified. The investigated Thymus species of Bosnian origin clearly belong to the thymol-chemotype with relatively abundant level of this main constituent varying from 30.5% for T. serpyllum, and 34.5% for T. aureopunctatus, to 44.2% for Thymus spp., while their corresponding headspace samples contain very high percentage of p-cymene, thymol biosynthesis precursor, in the range from 29....
Natural product communications
Hydrodistilled essential oil and the corresponding headspace volatiles of Bosnian wild growing Th... more Hydrodistilled essential oil and the corresponding headspace volatiles of Bosnian wild growing Thymus praecox ssp. polytrichus (A. Kern. Ex Borbàs) Jalas and Thymus praecox ssp. skorpilii (Velen.) Jalas were subjected to capillary GC-MS analysis. This work presents a detailed essential oil analysis of these two rare Thymus subspecies from Bosnia, as well as the very first report on their headspace composition. Eighty-seven volatile constituents were identified in four samples. Two alcohols were the major constituents in the essential oil of T. praecox ssp. polytrichus, a monoterpene, linalool (13.9%), and a sesquiterpene, (E)-nerolidol (10.4%), while linalyl acetate (36.7%) and linalool (22.7%) were the most abundant volatiles in the corresponding headspace sample. Oxygenated monoterpenes (57.5%) predominate in the essential oil of T. praecox ssp. skorpilii with linalyl acetate (28.7%) and linalool (14.4%) as the main representatives. Headspace sample of this subspecies also showed ...
Mass spectrometry has been applied for the structural study of some new asymmetrically 2,3-disubs... more Mass spectrometry has been applied for the structural study of some new asymmetrically 2,3-disubstituted 4-quinolinecarboxylic acids, synthesized by a rational modification of the general procedure of Doebner cyclocondensation of quinoline from anilines, various aldehydes and pyruvic acid derivatives. The new glucosides of quinoline type have been prepared starting from glucoside helicin, 2-(β-D-glucopyranosiloxy) benzaldehyde, as a donor of carbonyl function that condenses with aniline as a primary aromatic amine and three different 2-oxocarboxylic acids: 2-oxobutanoic acid, 2-oxopentanedicarboxylic acid and 2-oxo-3-phenylpropanoic acid. Unexpected by-products having the structure of dihydropyrrolones were isolated and their structures were confirmed by means of mass spectrometry. The principal mass spectra fragmentation patterns of corresponding aglucon components, obtained by the cleveage of the glycosidic linkage of synthesized heterocyclic glucosides, are discussed.
Journal of Essential Oil Bearing Plants, 2009
ABSTRACT Satureja is a genus of the well-known medicinal plants of Lamiaceae family that comprise... more ABSTRACT Satureja is a genus of the well-known medicinal plants of Lamiaceae family that comprises numerous species growing wild in the Mediterranean area. The essential oils of Satureja visianii Silic and Satureja montana L., growing together at the same habitat under similar environmental conditions, were subjected to detailed gas chromatography-mass spectrometry analysis in order to compare their chemical composition. S. visianii Silic is a stenoendemic species with narrow geographical distribution limited to only one locality, Peljesac Peninsula in Croatia. More than one hundred twenty compounds were identified in both plant oils representing 90.4 % - 99.5 % of the total oil. The most abundant components in S. visianii essential oil were viridiflorol (17.9 %), borneol (12.6 %) and camphor (6.5 %), while S. montana oil was rich in phenolic compounds carvacrol (59.1 %) and thymol (20.1 %).
Analytical Chemistry Letters, 2011
ABSTRACT
Natural Product Research, 2015
Helichrysum italicum (Roth) G. Don is a flowering plant of the family Asteraceae. It is rich in o... more Helichrysum italicum (Roth) G. Don is a flowering plant of the family Asteraceae. It is rich in oil that is used for different medicinal purposes and in fragrance industry. Volatile profile of four populations of H. italicum, collected from natural habitat in Dalmatia (Croatia), was analysed by capillary GC-MS. Sample from BraČ Island had α-trans-bergamotene (10.2%) and β-acoradiene (10.1%) as the majors, whereas sample collected on Biokovo Mt. was rich in neryl acetate (8.1%). β-Acoradiene was also the main constituent of sample collected near Tijarica, whereas rosifoliol (8.5%) was the most abundant constituent in sample collected near Makarska. Presented results show the influence of environmental conditions on chemical differentiation of the volatiles of H. italicum from Croatia.
Natural Product Research, 2014
The objective of this study was to determine total phenolic and flavonoid contents, antioxidant a... more The objective of this study was to determine total phenolic and flavonoid contents, antioxidant and antimicrobial activities of methanolic extracts from the leaves and barks of three Alnus species. The phenolic and flavonoid contents of extracts were determined spectrophotometrically using Folin-Ciocalteau and aluminium chloride methods, respectively. In addition, antioxidant activity of the extracts was determined using 1,1-diphenyl-2-picrylhydrazyl radical scavenging method. The antimicrobial activity was performed by disc diffusion assay against six reference bacterial strains including Gram-negative and Gram-positive bacteria and two fungal strains. Extract of Alnus viridis bark contained the highest amounts of total phenolics (780 mg CAT/g), while extract of A. viridis leaves had the highest amount of flavonoids (30.01 mg RUT/g). All extracts showed antioxidant activity higher than thymol, which was used as a positive probe. The largest diameters of inhibition zone (25 mm) were recorded with Bacillus subtilis 168 M and Staphylococcus aureus ATCC 6538.
Natural Product Research, 2011
This study was undertaken in order to evaluate possible antioxidative and antiproliferative activ... more This study was undertaken in order to evaluate possible antioxidative and antiproliferative activities of three Helleborus taxa. The dry leaves and roots of three Helleborus taxa were extracted with ethanol and water. A phytochemical evaluation of the selected extracts was performed using spectrophotometric methods and a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity assay was used for measuring the antioxidative activity of
Rapid Communications in Mass Spectrometry, 1990
ABSTRACT
Journal of Enzyme Inhibition and Medicinal Chemistry, 2016
The effect of Ca(2+) ions on the cytotoxic ability of boron heterocyclic compound dipotassium-tri... more The effect of Ca(2+) ions on the cytotoxic ability of boron heterocyclic compound dipotassium-trioxohydroxytetrafluorotriborate (K2[B3O3F4OH]), on in vitro tumor cells (mammary adenocarcinoma 4T1, melanoma B16F10 and squamous cell carcinoma SCCVII) and non-tumoral fibroblast cells (mouse dermal L929 and hamster lung V79) was examined. At small concentrations of Ca(2+) ions (0.42 mM), K2[B3O3F4OH] (3.85 mM) has a very strong cytotoxic effect on all cancer cells tested (89.1, 85.6 and 84.6%) and significantly less effect on normal cells (19.5 and 24.2%), respectively. Applying larger concentrations of Ca(2+) ions (9.42-72.42 mM), at the same concentration of K2[B3O3F4OH], no significant cytotoxic effect was detected on cancer cells and normal cells investigated. The selective ability of K2[B3O3F4OH], in the medium with a low concentration of Ca(2+) ions has a strong cytotoxic effect on cancer cells and very weak effect in normal cells, opens up the possibility of its application in antitumor therapy.
Analytical Chemistry Letters, Mar 7, 2013
ABSTRACT
Food Chemistry, Nov 1, 2009
A series of selected 4-methylcoumarins (4-methyl-2H-1-benzopyran-2-ones) were synthesised and tes... more A series of selected 4-methylcoumarins (4-methyl-2H-1-benzopyran-2-ones) were synthesised and tested for radical-scavenging ability using the stable 1,1-diphenyl-2-picrylhydrazyl radical, and for reducing power ability with a test based on the reduction of ferric to ferrous cation. All studied compounds showed activity comparable to Trolox (6-hydroxy-2,5,7,8-tetramethylchroman-2-carboxylic acid), an already known antioxidant, which is used as standard in most of the testing methods. Observations from the study were made with regard to structural features that regulated the behaviour of the compounds. The antioxidant activity of some 4-methylcoumarin representatives is presented here for the first time and extends our knowledge of the range of valuable biological activities and possible roles in therapy and for food preservation associated with this group of compounds.
Http Dx Doi Org 10 1080 0972060x 2009 10643720, Mar 12, 2013
Satureja is a genus of the well-known medicinal plants of Lamiaceae family that comprises numerou... more Satureja is a genus of the well-known medicinal plants of Lamiaceae family that comprises numerous species growing wild in the Mediterranean area. The essential oils of Satureja visianii Šilic and Satureja montana L., growing together at the same habitat under similar environmental conditions, were subjected to detailed gas chromatography-mass spectrometry analysis in order to compare their chemical composition. S. visianii Šilic is a stenoendemic species with narrow geographical distribution limited to only one locality, Pelješac Peninsula in Croatia. More than one hundred twenty compounds were identified in both plant oils representing 90.4 % -99.5 % of the total oil. The most abundant components in S. visianii essential oil were viridiflorol (17.9 %), borneol (12.6 %) and camphor (6.5 %), while S. montana oil was rich in phenolic compounds carvacrol (59.1 %) and thymol (20.1 %).
Pharmaceutical Biology, May 23, 2015
Stachys menthifolia Vis. (Lamiaceae) is an endemic species from the Balkan Peninsula spread throu... more Stachys menthifolia Vis. (Lamiaceae) is an endemic species from the Balkan Peninsula spread throughout Albania, Greece, Montenegro, and Croatia. This article presents the first investigation of the essential oil composition of this species from Croatia. Aerial parts of the plant were collected from three different natural habitats in the region of Biokovo Mountain. The studied populations showed similarity in qualitative, but not in quantitative, composition of their essential oils. Hydrodistilled volatile oil obtained from the plant material of S. menthifolia was subjected to gas chromatographic analysis coupled to mass spectrometry. More than 100 compounds were identified in the three samples, representing 86.8-90.8% of the total oil. The terpene profile of S. menthifolia is characterized by a high content of oxygenated sesquiterpenes (48.4-58.9%) and diterpene hydrocarbons (3.5-25.2%), with 8-α-acetoxyelemol (6.9-21.3%), abietatriene (3.5-21.1%), and 4'-methoxyacetophenone (4.5-17.0%) as the main constituents.
Chemistry & Biodiversity
Essential-oil profile of Salvia brachyodon Vandas, an endemic Dinaric species transferred from Ad... more Essential-oil profile of Salvia brachyodon Vandas, an endemic Dinaric species transferred from Adriatic Coast to the continental climatic conditions, was determined. Hydrodistilled oils obtained from the plant material collected in three-year field trial were subjected to the detailed GC/MS analysis. Hundred and fifty volatile compounds were identified in four samples. Comparison of the chemical composition of the isolated essential oils showed that population collected one year after transfer preserved sesquiterpene character of its oil (74.3%), while all subsequent samples gave the oils of monoterpene type with 1,8-cineole as the principal constituent (22.2 -42.3%). The high degree of variation in the qualitative and quantitative composition of the volatile constituents revealed the strong influence of environmental conditions on the nature of plant chemical composition that has an important role in a plant adaptation.
Ćavar, S., Maksimović, M., Šolić, M. E.: Comparison of Essential Oil Composition of Stachys menth... more Ćavar, S., Maksimović, M., Šolić, M. E.: Comparison of Essential Oil Composition of Stachys menthifolia Vis. from Two Natural Habitats in Croatia. Biologica Nyssana, 1 (1-2), December 2010: 99-103.
Natural product communications
Essential oil of Thymus aureopunctatus (Beck) K. Malý, obtained by hydrodistillation and headspac... more Essential oil of Thymus aureopunctatus (Beck) K. Malý, obtained by hydrodistillation and headspace technique, was subjected to capillary GC-MS analysis, and its volatile composition was compared with essential oil profile of Thymus serpyllum L. and a botanically undetermined thyme species, Thymus spp., all growing wild in the same habitat in Bosnia and Herzegovina. This paper presents the first report on phytochemical analysis of the rare T. aureopunctatus species, and also the first report on headspace analysis of plants belonging to the genus Thymus. One hundred and two volatile constituents were identified. The investigated Thymus species of Bosnian origin clearly belong to the thymol-chemotype with relatively abundant level of this main constituent varying from 30.5% for T. serpyllum, and 34.5% for T. aureopunctatus, to 44.2% for Thymus spp., while their corresponding headspace samples contain very high percentage of p-cymene, thymol biosynthesis precursor, in the range from 29....
Natural product communications
Hydrodistilled essential oil and the corresponding headspace volatiles of Bosnian wild growing Th... more Hydrodistilled essential oil and the corresponding headspace volatiles of Bosnian wild growing Thymus praecox ssp. polytrichus (A. Kern. Ex Borbàs) Jalas and Thymus praecox ssp. skorpilii (Velen.) Jalas were subjected to capillary GC-MS analysis. This work presents a detailed essential oil analysis of these two rare Thymus subspecies from Bosnia, as well as the very first report on their headspace composition. Eighty-seven volatile constituents were identified in four samples. Two alcohols were the major constituents in the essential oil of T. praecox ssp. polytrichus, a monoterpene, linalool (13.9%), and a sesquiterpene, (E)-nerolidol (10.4%), while linalyl acetate (36.7%) and linalool (22.7%) were the most abundant volatiles in the corresponding headspace sample. Oxygenated monoterpenes (57.5%) predominate in the essential oil of T. praecox ssp. skorpilii with linalyl acetate (28.7%) and linalool (14.4%) as the main representatives. Headspace sample of this subspecies also showed ...
Mass spectrometry has been applied for the structural study of some new asymmetrically 2,3-disubs... more Mass spectrometry has been applied for the structural study of some new asymmetrically 2,3-disubstituted 4-quinolinecarboxylic acids, synthesized by a rational modification of the general procedure of Doebner cyclocondensation of quinoline from anilines, various aldehydes and pyruvic acid derivatives. The new glucosides of quinoline type have been prepared starting from glucoside helicin, 2-(β-D-glucopyranosiloxy) benzaldehyde, as a donor of carbonyl function that condenses with aniline as a primary aromatic amine and three different 2-oxocarboxylic acids: 2-oxobutanoic acid, 2-oxopentanedicarboxylic acid and 2-oxo-3-phenylpropanoic acid. Unexpected by-products having the structure of dihydropyrrolones were isolated and their structures were confirmed by means of mass spectrometry. The principal mass spectra fragmentation patterns of corresponding aglucon components, obtained by the cleveage of the glycosidic linkage of synthesized heterocyclic glucosides, are discussed.
Journal of Essential Oil Bearing Plants, 2009
ABSTRACT Satureja is a genus of the well-known medicinal plants of Lamiaceae family that comprise... more ABSTRACT Satureja is a genus of the well-known medicinal plants of Lamiaceae family that comprises numerous species growing wild in the Mediterranean area. The essential oils of Satureja visianii Silic and Satureja montana L., growing together at the same habitat under similar environmental conditions, were subjected to detailed gas chromatography-mass spectrometry analysis in order to compare their chemical composition. S. visianii Silic is a stenoendemic species with narrow geographical distribution limited to only one locality, Peljesac Peninsula in Croatia. More than one hundred twenty compounds were identified in both plant oils representing 90.4 % - 99.5 % of the total oil. The most abundant components in S. visianii essential oil were viridiflorol (17.9 %), borneol (12.6 %) and camphor (6.5 %), while S. montana oil was rich in phenolic compounds carvacrol (59.1 %) and thymol (20.1 %).
Analytical Chemistry Letters, 2011
ABSTRACT
Natural Product Research, 2015
Helichrysum italicum (Roth) G. Don is a flowering plant of the family Asteraceae. It is rich in o... more Helichrysum italicum (Roth) G. Don is a flowering plant of the family Asteraceae. It is rich in oil that is used for different medicinal purposes and in fragrance industry. Volatile profile of four populations of H. italicum, collected from natural habitat in Dalmatia (Croatia), was analysed by capillary GC-MS. Sample from BraČ Island had α-trans-bergamotene (10.2%) and β-acoradiene (10.1%) as the majors, whereas sample collected on Biokovo Mt. was rich in neryl acetate (8.1%). β-Acoradiene was also the main constituent of sample collected near Tijarica, whereas rosifoliol (8.5%) was the most abundant constituent in sample collected near Makarska. Presented results show the influence of environmental conditions on chemical differentiation of the volatiles of H. italicum from Croatia.
Natural Product Research, 2014
The objective of this study was to determine total phenolic and flavonoid contents, antioxidant a... more The objective of this study was to determine total phenolic and flavonoid contents, antioxidant and antimicrobial activities of methanolic extracts from the leaves and barks of three Alnus species. The phenolic and flavonoid contents of extracts were determined spectrophotometrically using Folin-Ciocalteau and aluminium chloride methods, respectively. In addition, antioxidant activity of the extracts was determined using 1,1-diphenyl-2-picrylhydrazyl radical scavenging method. The antimicrobial activity was performed by disc diffusion assay against six reference bacterial strains including Gram-negative and Gram-positive bacteria and two fungal strains. Extract of Alnus viridis bark contained the highest amounts of total phenolics (780 mg CAT/g), while extract of A. viridis leaves had the highest amount of flavonoids (30.01 mg RUT/g). All extracts showed antioxidant activity higher than thymol, which was used as a positive probe. The largest diameters of inhibition zone (25 mm) were recorded with Bacillus subtilis 168 M and Staphylococcus aureus ATCC 6538.
Natural Product Research, 2011
This study was undertaken in order to evaluate possible antioxidative and antiproliferative activ... more This study was undertaken in order to evaluate possible antioxidative and antiproliferative activities of three Helleborus taxa. The dry leaves and roots of three Helleborus taxa were extracted with ethanol and water. A phytochemical evaluation of the selected extracts was performed using spectrophotometric methods and a 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activity assay was used for measuring the antioxidative activity of
Rapid Communications in Mass Spectrometry, 1990
ABSTRACT