Chemical Composition and In Vitro Antioxidant Activity of Sida rhombifolia L. Volatile Organic Compounds.

In the current study, the phytochemical constituents of volatile organic compounds (VOCs) obtained from Sida rhombifolia L. were identified by GC-FID and GC-MS analysis. A total of 73 volatile organic compounds were identified. The major components of S. rhombifolia VOCs were identified as palmitic acid (21.56%), phytol (7.02%), 6,10,14-trimethyl-2-pentadecanone (6.30%), oleic acid (5.48%), 2-pentyl-furan (5.23%), and linoleic acid (3.21%). The VOCs are rich in fatty acids (32.50%), olefine aldehyde (9.59%), ketone (9.41%), enol (9.02%), aldehyde (8.63%), and ketene (6.41%). The antioxidant capacity of S. rhombifolia VOCs was determined by 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH), 2,2-azinobis-(3-ethylbenzothiazolin-6-sulfonic acid) diammonium salt (ABTS), and ferric reducing/antioxidant power (FRAP) methods with butylated hydroxytoluene (BHT) and Trolox as standard. The VOCs showed dose-dependent antioxidant activity with IC50 (50% inhibitory concentration) values of 5.48 ± 0.024 and 1.47 ± 0.012 mg/mL for DPPH and ABTS assays, respectively. FRAP antioxidant capacity was 83.10 ± 1.66 mM/g. The results show that the VOCs distilled from S. rhombifolia have a moderate antioxidant property that can be utilized as a natural botanical supplement or an antioxidant.

Effectiveness of the Natural Antioxidant 2,4,4'-Trihydroxychalcone on the Oxidation of Sunflower Oil during Storage.

This study aimed to investigate the effectiveness of 2,4,4'-trihydroxychalcone as a natural antioxidant on the oxidation of sunflower oil during an 88-day storage period and to compare its strength with the synthetic antioxidant butylated hydroxytoluene (BHT). Seven groups of the sunflower oil samples were prepared: pure oil (control), oil treated with different concentrations (100, 500, and 1000 ppm) of 2,4,4'-trihydroxychalcone, and oil treated with different concentrations (100, 500, and 1000 ppm) of BHT. Specific parameters, namely, the peroxide value (PV), acid value (AV), p-anisidine value (p-AnV), thiobarbituric acid reactive substance (TBARS) value and total oxidation (TOTOX) value were used to assess the extent of the deterioration of the oil by estimating the primary and secondary oxidation products. The results showed that 2,4,4'-trihydroxychalcone effectively decreased the production of the primary and secondary oxidation products of sunflower oil during storage, as indicated by reductions in the PVs, AVs, p-AnVs, TBARS values and TOTOX values of the sunflower oil. When compared to BHT, 2,4,4'-trihydroxychalcone showed either a similar or stronger effect in inhibiting the primary and secondary oxidation products. These findings suggest that, 2,4,4'-trihydroxychalcone is a suitable natural alternative to synthetic antioxidants to improve the oxidative stability of sunflower oil.

Strategies to Improve the Thermo-Oxidative Stability of Sunflower Oil by Exploiting the Antioxidant Potential of Blueberries Processing Byproducts.

This research was conducted in order to establish the effectiveness of two freeze-dried extracts obtained from blueberry processing byproducts resulting from juice manufacturing compared to butylated hydroxytoluene (BHT) in delaying the lipid oxidation of sunflower oil subjected to high-temperature convective heating at 180 °C up to 12 h under simulated frying conditions. The fruits were harvested from spontaneous flora of two regions of Romania, Arieseni (Alba County) and Paltinis (Sibiu County) and the blueberry byproducts extracts (BBE) were noted according to the origin place as ABBE and PBBE. The progress of lipid thermo-oxidation was investigated in terms of peroxide value (PV), p-anisidine value (p-AV), the response of TBA-malondialdehyde interactions assessed by thiobarbituric acid (TBA) method, the total oxidation (TOTOX) value and inhibition of oil oxidation (IO). The recorded data highlighted that BBE exhibit a high inhibitory response on lipid thermo-oxidation. The inhibitory effect was concentration-dependent, thus, the degree of lipid oxidation was in reverse related to the BBE dose. The exposure of the oil samples supplemented with 800 ppm BBE (ABBE, PBBE) to a high-temperature heating for 12 h led to a significant decrease of the assessed indices compared to additives-free sunflower oil sample as follows: PV (46%; 45%), p-AV (21%; 17%), TOTOX (27%; 24%), TBA value (25%; 11%). Regarding the impact of the origin on the potential of BBE to inhibit the lipid oxidative degradation, it was noted that ABBE derived from blueberries grown in a region with a milder climate with moderate precipitations and higher temperatures showed a stronger inhibitory effect on lipid thermo-oxidation than PBBE. A moderate level of 500 ppm BBE inhibited the lipid oxidation similar to 200 ppm BHT. The reported results reveal that BBE represent efficient natural antioxidants that could be successfully applied to improve the thermo-oxidative stability of sunflower oil used in various high-temperature food applications.

Effect of pomegranate peel extract on the oxidative stability of pomegranate seed oil.

Pomegranate seed oil is valuable source of bioactive compounds with health-beneficial effects, but it is sensitive to oxidation due to high content of PUFA. In order to improve stability of pomegranate seed oil, the influence of natural antioxidant (0.1% pomegranate peel extract) and a combination of synthetic antioxidant (0.01% butylhydroxytoluene) and pomegranate peel extract (0.05%) was investigated. The oxidation process was followed by monitoring fatty acid composition and measuring the quality and stability parameters of oil (acid value, peroxide value, anisidine value and thiobarbituric acid reactive substances value) during storage for 12 days at 65 °C. Furthermore, total phenolic content and DPPH radical scavenging activity was measured. Pomegranate peel extract as well as a combination of pomegranate peel extract and BHT can have a significant positive impact (P < 0.05) on improvement of the quality and stability parameters of pomegranate seed oil. Furthermore, such activity was better than BHT used alone.

Antioxidant Activity of Pastinaca sativa L. ssp. sylvestris [Mill.] Rouy and Camus Essential Oil.

In the last decade, there has been growing interest in the food industry in replacing synthetic chemicals with natural products with bioactive properties. This study's aims were to determine the chemical composition and the antioxidant properties of the essential oil of Pastianica sylvestris. The essential oil was isolated with a yield of 0.41% (w/v) by steam distillation from the dried seeds and subsequently analysed by GC-MS. Octyl acetate (78.49%) and octyl hexanoate (6.68%) were the main components. The essential oil exhibited an excellent activity for the inhibition of primary and secondary oxidation products for cold-pressed sunflower oil comparable with butylated hydroxyanisole (BHA) and butylated hydroxytoluene (BHT), which were evaluated using peroxide and thiobarbituric acid values. The antioxidant activity of the essential oil was additionally validated using DPPH radical scavenging (0.0016 ± 0.0885 mg/mL), and ß-carotene-linoleic acid bleaching assays. Also, the amounts of total phenol components (0.0053 ± 0.0023 mg GAE/g) were determined.

Effect of tomato (Solanum lycopersicum L.) lycopene-rich extract on the kinetics of rancidity and shelf-life of linseed (Linum usitatissimum L.) oil.

The effect of tomato lycopene-rich extract (TLE) addition on shelf-life of linseed oil was evaluated. Linseed oil was extracted by cold pressing and TLE by supercritical CO2. Linseed oils with and without TLE addition were characterized for moisture, color, refractive index, fatty acid composition and antioxidants. Adding TLE to 80 mg lycopene/kg oil improved linseed oil stability, showing the same induction time at 110 °C (by Rancimat) of control linseed oil with 200 mg/kg butylhydroxytoluene. The increase of free fatty acid, peroxide value, p-anisidine value, K232 and K268 at 40, 50, and 60 °C until 90 days followed first-order kinetics. Rancidity rate augmented with temperature. TLE addition slowed oil degradation without changing the mechanism since the Arrhenius lines were parallel. Mean Ea were respectively 38.2, 24.7, 38.0, 38.2, 41.5 kJ/mol. TLE addition increased linseed oil shelf-life by 31% (Rancimat) and by 42% (stability kinetics during storage).

A new and feasible analytical method using reversed-phase dispersive liquid-liquid microextraction (RP-DLLME) for further determination of Nickel in hydrogenated vegetable fat.

A new and simple method for Ni determination in hydrogenated vegetable fat (HVF) has been developed using a RP-DLLME sample preparation procedure for further determination by flame atomic absorption spectrometry (FAAS) and graphite furnace atomic absorption spectrophotometry (GFAAS). The RP-DLLME procedure includes simultaneous microextraction and preconcentration of Ni in HVF, using 5.0 g of HVF preheated (75 °C) and diluted in 5.0 mL of xylene, with the addition of a dispersant/extractant mixture (n-propanol/dilute HNO3). The sample was manually stirred and centrifuged and the aqueous phase was collected for further Ni determination by FAAS and GFAAS. RP-DLLME was carried out using only 700 µL of n-propanol and 300 µL of 2.0 mol L-1 HNO3. The recovery varied from 93.3% to 101.5% for HVF. The LODs and LOQs were 40 and 90 ng g-1 for FAAS, and 0.41 and 1.36 ng g-1 for GFAAS. The proposed analytical method is viable and this is the first application of RP-DLLME to solid fat samples, with Ni determination as an example of application. This method consumes small amounts of reagents, with lower toxicity as compared to microwave decomposition. Furthermore, the key features of the RP-DLLME method include simplicity of operation, high sample mass, reduced reagent consumption, and use of diluted HNO3 as an extractant.

A quanti-qualitative study of a phenolic extract as a natural antioxidant in the frying processes.

The aim of this work was to evaluate the effects of a phenolic extract from olive mill waste water on the stabilization of refined olive oil and on French fry quality during the frying process. Frozen, pre-fried potatoes were fried at 180 °C for 8 min in refined olive oil enriched by different concentrations of a phenolic extract, while oil enriched by a common synthetic antioxidant (butylated hydroxytoluene) was used for comparison. The whole frying process took six hours. The phenolic extract has revealed as a very promising oil stabilizing agent during frying, playing an important role (dose-dependent) in preserving the antioxidants both in oil and in food, in reducing the formation of unwanted compounds (acrolein and hexanal), and in contrasting the acrylamide production. These results clearly show that the phenolic extract can be used as a source of natural antioxidants to replace (or avoid) synthetic additives in foods or beverages.

Contribution of organic acids to α-terpinene antioxidant activity.

DPPH scavenging activity and antioxidant activity in canola oil of α-terpinene, BHT (butylated hydroxytoluene) and acetic, malic and citric acids and their mixtures were determined to examine the synergistic effect on the antioxidant activity. The results demonstrated that α-terpinene and organic acids had low or any activity against DPPH and BHT showed an IC50 of 0.035 mM. When mixed with organic acids, α-terpinene increased its activity showing a synergistic effect. The mix of α-terpinene (1.58 mM) and citric acid (2.91 mM) showed the higher synergistic effect in DPPH (121.82). BHT scavenging activity was inhibited by organic acids. Although the DPPH scavenging activity was enhanced for α-terpinene and inhibited for BHT by organic acids, the antioxidant activity in canola oil was not. It indicated that the scavenging DPPH activity and antioxidant activity in canola oil of a compound or a mixture of compounds are not always positively correlated with each other.

Synthesis and Computational Studies Demonstrate the Utility of an Intramolecular Styryl Diels-Alder Reaction and Di-t-butylhydroxytoluene Assisted [1,3]-Shift to Construct Anticancer dl-Deoxypodophyllotoxin.

Deoxypodophyllotoxin is a secondary metabolite lignan possessing potent anticancer activity with potential as a precursor for known anticancer drugs, but its use is limited by scarcity from natural sources. We here report the total synthesis of racemic deoxypodophyllotoxin in seven steps using an intramolecular styryl Diels-Alder reaction strategy uniquely suited to assemble the deoxypodophyllotoxin core. Density functional theory was used to analyze concerted, polar, and singlet-open-shell diradical reaction pathways, which identified a low-energy concerted [4 + 2] Diels-Alder pathway followed by a faster di-t-butylhydroxytoluene assisted [1,3]-formal hydrogen shift.

Oxidative stability of refined olive and sunflower oils supplemented with lycopene-rich oleoresin from tomato peels industrial by-product, during accelerated shelf-life storage.

Tomato peels by-product from a Tunisian industry was used for the extraction of lycopene-rich oleoresin using hexane solvent maceration. Tomato peels oleoresin, TPO, exhibited competitive free radicals scavenging activity with synthetic antioxidants. The efficacy of TPO in stabilizing refined olive (ROO) and sunflower (RSO) oils was investigated for five months, under accelerated shelf-life, compared to the synthetic antioxidant, butylated hydroxytoluene (BHT). TPO was added to ROO and RSO at four different concentrations, namely 250, 500, 1000 and 2000 µg/g and BHT standard at 200 µg/g. Lipid oxidation was tracked by measuring the peroxide value, acidity, conjugated dienes and trienes. Results suggested the highest efficiency of 250 µg/g and 2000 µg/g of TPO, referring to 5 µg/g and 40 µg/g of lycopene, for the oxidative stabilization of ROO and RSO, respectively. The protective effect of TPO against the primary oxidation of these refined oils was significantly correlated to their lycopene contents.

The emu oil emulsified in egg lecithin and butylated hydroxytoluene enhanced the proliferation, stemness gene expression, and in vitro wound healing of adipose-derived stem cells.

In recent decades, mesenchymal stem cells originated from adipose tissue (adipose-derived stem cells, ASCs) have gained increased attention for production of cell-based therapeutics. Emu oil as a natural compound showed antioxidant effects in previous studies. The goal of this study was to investigate the effect of crude emu oil on the proliferation, cell cycle progression, stemness genes expression, and in vitro wound healing potential of ASCs. An emulsion of emu oil was prepared using egg lecithin and butylated hydroxytoluene to improve bioavailability and solubility of emu oil in the expansion medium. The ASCs were treated using a series of emu oil concentrations in emulsion form, diluted in expansion medium (0.03-3 mg/ml). The emu oil-free emulsion was used as control treatment. The results revealed that emu oil (1.25 mg/ml) in emulsion form significantly (p < 0.001) increased ASCs proliferation and colony formation. Additionally, emu oil caused upregulation of stemness marker genes (Sox2, Oct4, Nanog, and Nestin) (p < 0.05). The cell cycle analysis after emu oil treatments showed an increase in the population of ASCs in S-phase of the cell cycle. Besides, an accelerated in vitro scratch wound healing was observed in emu oil-treated ASCs. Emu oil enhanced proliferation, colony formation, stemness genes expression, and in vitro wound healing of ASCs. These findings suggest that emu oil treatment could maintain the stemness of ex vivo cultivated ASCs and enhance their regenerative potential.

Synthesis and Application of a New Amphiphilic Antioxidant.

A new amphiphilic antioxidant (tannyl stearate) derived from reaction of tannic acid with stearic acid was synthesized in order to improve tannic acid solubility in lipid materials. This reaction gives many products having different degree of esterification (tannyl mono, di, tri, tetra, penta, hexa, hepta……stearate) which were separated using silica gel column chromatography and tentative identification was carried out using thin layer chromatography (TLC). The intrinsic viscosities (η) were used to differentiate between the different molecular weight of the produced esters1). Tannyl penta stearate is assumed to be the most suitable amphiphilic antioxidant derivative, where those derivatives with less degree of esterification would be less soluble in fat, and those of higher degree of esterification would exhaust more hydroxyl group that cause decreases of antioxidant activity. The structure of tannyl penta stearate was approved depending on its chemical analysis and spectral data (IR, H1 NMR,). The emulsification power of tannyl penta stearate was then determined according to method described by El-Sukkary et al.2), in order to prove its amphiphilic property. Then tannyl penta stearate was tested for its antioxidant and radical scavenging activities in three different manners, those are, lipid oxidation in sunflower oil using Rancimat, (DPPH) free radical scavenging and total antioxidant activity. {Pure tannic acid (T), butylhydroxyanisol (BHA) and butylhydroxytoluene (BHT) were used as reference antioxidant radical saving compounds}. Then tannyl penta stearate was added to sunflower oil, frying process was carried out and all physicochemical parameters of the oil were considered, and compared to other reference antioxidant in order to study the effect of this new antioxidant toward oil stability. Acute oral toxicity of the tannyl penta stearate was carried out using albino mice of 21-25 g body weight to determine its safety according to the method described by Goodman et al.3). Also liver and kidney functions of those mice were checked. Thus it could be concluded that the addition of tannyl penta stearate to frying oils offers a good protection against oxidation. The effectiveness of tannyl penta stearate as lipid antioxidant has been attributed mainly to its stability at high temperature. And according to acute lethal toxicity test tannyl penta stearate was found to be a safe compound that can be used as food additive.

The effect of antioxidants on quantitative changes of lysine and methionine in linoleic acid emulsions at different pH conditions.

BACKGROUND: Plants are an important source of phenolic compounds. The antioxidant capacities of green tea, thyme and rosemary extracts that contain these compounds have been reported earlier. However, there is a lack of accessible information about their activity against lipid oxidation in emulsions and inhibit the interaction of lipid oxidation products with amino acids. Therefore, the influence of green tea, thyme and rosemary extracts and BHT (butylated hydroxytoluene) on quantitative changes in lysine and methionine in linoleic acid emulsions at a pH of isoelectric point and a pH lower than the isoelectric point of amino acids was investigated. METHODS: Total phenolic contents in plant extracts were determined spectrophotometrically by using Folin-Ciocalteu's reagent, and individual phenols by using HPLC. The level of oxidation of emulsion was determined using the measurement of peroxides and TBARS (thiobarbituric acid reactive substances). Methionine and lysine in the system were reacted with sodium nitroprusside and trinitrobenzenesulphonic acid respectively, and the absorbance of the complexes was measured. RESULTS: Extract of green tea had the highest total polyphenol content. The system containing antioxidants and amino acid protected linoleic acid more efficiently than by the addition of antioxidants only. Lysine and methionine losses in samples without the addition of antioxidants were lower in their isoelectric points than below these points. Antioxidants decrease the loss of amino acids. The protective properties of antioxidants towards methionine were higher in a pH of isoelectric point whereas towards lysine in pH below this point. CONCLUSIONS: Green tea, thyme and rosemary extracts exhibit antioxidant activity in linoleic acid emulsions. Moreover, they can be utilized to inhibit quantitative changes in amino acids in lipid emulsions. However, the antioxidant efficiency of these extracts seems to depend on pH conditions. Further investigations should be carried out to clarify this issue.

Method validation and measurement uncertainty for the simultaneous determination of synthetic phenolic antioxidants in edible oils commonly consumed in Korea.

This study investigated a method for the validation and determination of measurement uncertainty for the simultaneous determination of synthetic phenolic antioxidants (SPAs) such as propyl gallate (PG), octyl gallate (OG), dodecyl gallate (DG), 2,4,5-trihydroxy butyrophenone (THBP), tert-butylhydroquinone (TBHQ), butylated hydroxyanisole (BHA), and butylated hydroxytoluene (BHT) in edible oils commonly consumed in Korea. The validated method was able to extract SPA residues under the optimized HPLC-UV and LC-MS/MS conditions. Furthermore, the measurement of uncertainty was evaluated based on the precision study. For HPLC-UV analysis, the recoveries of SPAs ranged from 91.4% to 115.9% with relative standard deviations between 0.3% and 11.4%. In addition, the expanded uncertainties of the SPAs ranged from 0.15 to 5.91. These results indicate that the validated method is appropriate for the extraction and determination of SPAs and can be used to verify the safety of edible oil products containing SPAs residues.

[Antiradical properties of essential oils and extracts from clove bud and pimento].

The antiradical properties of essential oils and extracts from the clove bud (Eugenia caryophyllata Thumb.) and berries of tree (Pimenta dioica (L.) Meriff) were studied and compared with the properties of synthetic antioxidant ionol (2,6-ditret-butyl-4-hydroxytoluene, BHT) in model reactions with the stable free 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical. The essential oils of clove bud and pimento had qualitatively close composition of the main components but differed by their quantitative content. In the studied samples, eugenol was the main compound with high antiradical activity. The reaction rates of essential oils and extracts with the DPPH radical were practically the same for essential oils and twice the reaction rate of BHT. The values of antiradical efficiency (AE) were also close for essential oils and were twice that for extracts and ionol. A synergetic action of components in the essential oil and extract of pimento on antiradical efficiency values was found.

Synthesis, characterization, and evaluation of 10-undecenoic acid-based epithio derivatives as multifunctional additives.

Novel epithio compounds from alkyl epoxy undecanoates (n-alkyl, C1, C4, and C6; isoalkyl, C3, C4, and C8) were synthesized using an ammonium thiocyanate in ionic liquid 1-methylimidazolium tetrafluoroborate/H2O (2:1) solvent system in 85-90% yields by gas chromatographic (GC) analysis. The synthesized products were characterized by (1)H and (13)C nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy (FTIR), gas chromatography, and GC mass spectral (GC-MS) analyses and evaluated for their antioxidant, extreme pressure (EP), and antiwear (AW) properties in three different base oils, namely, epoxy jatropha fatty acid n-butyl esters (EJB), di-2-ethylhexyl sebacate (DOS), and mineral oil (S-105). Among the synthesized products, n-butyl epithio undecanoate exhibited superior antioxidant property (229.2 °C) compared to butylated hydroxytoluene (BHT, 193.8 °C) in base oil DOS and comparable performance in EJB and S-105 base oils. All of the epithio derivatives exhibited significantly enhanced weld point for the base oils EJB and DOS at 2 wt % level and displayed moderate enhancement in S-105 base oil. Methyl epithio undecanoate at 0.6% concentration exhibited considerable improvement in the wear scar of DOS base oil. The synthesized epithio derivatives have potential as multifunctional additives in lubricant formulations.

Synthesis of epoxy jatropha oil and its evaluation for lubricant properties.

Vegetable oils are being investigated as potential source of environmentally favorable lubricants over synthetic products. Jatropha curcas L. oil (JO) identified as a potential raw material for biodiesel was explored for its use as a feedstock for biolubricants. Epoxidized jatropha oil (EJO) was prepared by peroxyformic acid generated in situ by reacting formic acid and hydrogen peroxide in the presence of sulfuric acid as catalyst. Almost complete conversion of unsaturated bonds in the oil into oxirane was achieved with oxirane value 5.0 and iodine value of oil reduced from 92 to 2 mg I2/g. EJO exhibited superior oxidative stability compared to JO. This study employed three antioxidants such as butylated hydroxy toluene (BHT), zinc dimethyl dithiocarbamate (ZDDC), and diphenyl amine (DPA) and found that DPA antioxidant performed better than ZDDC and BHT over EJO compared to JO. The lubricating properties of EJO and epoxy soybean oil (ESBO) are comparable. Hence, EJO can be projected as a potential lubricant basestock for high temperature applications.

[Determination of the antioxidant properties of activators of mitochondrial ATP-dependent potassium channels with the Amplex Red fluorescent indicator].

The effect of adaptogens-antihypoxants that participate in the activation of mitochondrial ATP-dependent potassium channels (mitoK(ATP)) at the oxidation of the Amplex Red (AR) fluorescent indicator in a peroxidase system was tested. It was shown that Extralife, Hypoxen, taurine, and synthetic antioxidant ionol can be arranged in the following row, according to the fluorescence inhibition activity: Extralife > Hypoxen > > ionol > taurine; their effect was shown to be concentration-dependent. The calculated K(i) value of fluorescence indicators demonstrate fast and slow phases of inhibition of the AR oxidation by Extralife and Hypoxen. The fast phase occurs in the presence of microdoses (0.05-3 microg/mL) of adaptogens and is related to the competition for H2O2, which is in agreement with our previous data on the mitoK(ATP) activation by doses of adaptogens related to the H2O2 consumption. The slow phase is characteristic of high adaptogen and ionol concentrations and is related to the competition for phenoxyl radicals of resorufin formed during AR oxidation. The obtained results allow one to suggest the application of a highly sensitive model peroxidase system with AR for the preliminary testing of compounds activating mitoK(ATP) channels.

Chemistry and biological activities of Tanacetum chiliophyllum var. oligocephalum extracts.

Tanacetum chiliophyllum (Fisch. & Mey.) var. oligocephalum (D.C.) Sosn. collected in Turkey was subjected to phytochemical and biological evaluations in this study. Pure compounds were obtained from ethyl acetate extracts of the stems of the plant material. Structures of isolated compounds were determined using spectral methods. Seven known flavones, i.e., 5-hydroxy-3',4',6,7-tetramethoxyflavone, eupatilin (6-hydroxyluteolin-6,3',4'-trimethylether), cirsimaritin (scuttellarin-6,7-dimethylether), cirsilineol, 5-hydroxy-3',4',7-trimethoxy flavone, desmethoxy-centaureidin, and jaceosidin and one known triterpene, taraxasterol acetate, were identified from the ethyl acetate extracts. The first seven compounds, as well as the ethyl acetate and methanol extracts, were also investigated for their insecticidal, antimicrobial, and 1,1-diphenyl-2-picrylhydrazil radical (DPPH)-scavenging activities. The insecticidal contact toxicity of the extracts were evaluated on Sitophilus granarius. The ethyl acetate (81.8%) and methanol (88.4%) extracts of T. chiliophyllum var. oligocephalum showed high toxicity against this pest. Most promising antimicrobial activity was observed for ethyl acetate extracts of the stems against Bacillus cereus. This extract showed the same inhibition concentration (125 microL/mg) with the positive control chloramphenicol. The ethyl acetate (91.9%) and methanol (93%) extracts of the stems showed significant DPPH-scavenging activity compared with the positive controls alpha-tocopherol (94.5%) and butylated hydroxytoluene (92.9%) at 10 mg/mL concentration. Among the isolated compounds, the highest DPPH-scavenging activity was observed for jaceosidin at 1 mg/mL concentration (81.5%).