Chemical composition and antioxidant and antimicrobial activity of essential oil of Artemisia annua L. from Bosnia

Hydrodistilled volatile oil obtained from the aerial parts of Artemisia annua L., cultivated near Sarajevo, Bosnia, was analyzed by GC-MS. More than one hundred compounds were identi?ed, representing 95.5% of the total oil. The major constituents of essential oil were oxygenated monoterpenes, artemisia ketone (30.7%) and camphor (15.8%). Isolated essential oil was tested for radical-scavenging ability using the stable DPPH radical, the ABTS radical, for reducing power ability with a test based on the reduction of ferric cations, for reducing ability of hydroxy radical in ORAC assay, and for metal chelating ability using the ferrozine assay. In all tests oil did not show a prominent antioxidant activity, but still comparable with thymol, an already known antioxidant. The screening of antimicrobial activity of oil was individually evaluated against representatives of Gram-positive, Gram-negative bacteria and fungi, using the agar diffusion method. All tested microorganisms were inhibited by essential oil. To the best of our knowledge, this is the first report of antimicrobial activity of essential oil of A. annua against Haemophilus influenzae, Enterococcus faecalis, Streptococcus pneumoniae, Micrococcus luteus and Candida krusei microbial strains. The antioxidant, antibacterial and antifungal activity of essential oil of A. annua from Bosnia is presented here for the first time and extends our knowledge in the range of valuable biological activities and possible roles in therapy associated with this medicinal herb.     

Variation in oil content and fatty acid profile of Calophyllum inophyllum L. with fruit maturity and its implications on resultant biodiesel quality

Variation in oil content and fatty acid profile (FAP) of Calophyllum inophyllum; a potential biodiesel feedstock species were studied at different maturity stages and biodiesel quality parameters were estimated based on the FAP. A steady increase in oil content was observed with maturity. Variation in palmitic (16:0) and linoleic (18:2) acids followed exactly opposite trends where palmitic acid content has decreased and linoleic acid content has increased 77 days after anthesis. Oleic acid (18:1) content has shown a steady increase. Stearic acid (18:0) content remained steady up to 68 days after anthesis and then felt slightly in 77 days after anthesis. Linoleic and eicosanoic acids were found to exist in low concentrations demonstrated very little compositional variation with fruit maturity. Estimated biodiesel parameters of all maturity stages were found to comply with industrial standards. Even though 48 days after anthesis had the most ideal FAP for biodiesel production, ∼77 days after anthesis is preferred point to harvest due to higher oil content.     

Characteristics, composition and thermal stability of Acacia senegal (L.) Willd. seed oil

The chemical composition, main physicochemical properties and thermal stability of oil extracted from Acacia senegal seeds were evaluated. The oil, moisture and the ash contents of the seeds were 9.80%, 6.92% and 3.82%, respectively. Physicochemical properties of the oil were iodine value, 106.56 g/100 g of oil; saponification value, 190.23 mg KOH/g of oil; refractive index (25 °C), 1.471; unsaponifiable matter, 0.93%; acidity, 6.41% and peroxide value, 5.43 meq. O₂/kg of oil. The main fatty acids in the oil were oleic acid (43.62%) followed by linoleic acid (30.66%) and palmitic acid (11.04%). The triacylglycerols (TAGs) with equivalent carbon number ECN 44 (34.90%) were dominant, followed by TAGs ECN 46 (28.19%), TAGs ECN 42 (16.48%) and TAGs ECN 48 (11.23%). The thermal stability analysed in a normal oxidizing atmosphere showed that the oil decomposition began at 268.6 °C and ended at 618.5 °C, with two stages of decomposition at 401.5 °C and 576.3 °C. According to these results, A. senegal seed oil has physicochemical properties, fatty acids composition and thermal characteristics that may become interesting for specific applications in several segments of food and non-food industries.     

Variations in essential oil yield and composition during Cinnamomum cassia bark growth

To extract essential oil for industrial use, the yields and compositions of bark oil during Cinnamomum cassia growth (1-3 years old for the branch bark; 5-12 years old for the stem bark) were determined. The branch bark fraction had a higher essential oil yield than the whole branch. The essential oil yield from branch bark varied within 2.70-3.11% (w/w), while that from stem bark was 0.41-2.61% (w/w) due to differences in age and segment (top, center and lower) of the tree. There were 41 volatile compounds identified in bark oil, among which the majority presented high fluctuations in percentage of composition both in different growth stages and segments. Variations in oil yields did not present the same pattern as the percentages of trans-cinnamaldehyde. The results suggest that choosing bark according to trees’ growth stages and separating stem barks into top, center and lower sections within a tree should significantly improve the extraction efficiency.     

Water deficit effects on caraway (Carum carvi L.) growth, essential oil and fatty acid composition

The Mediterranean region suffers of drought which affects plant behaviour regarding biochemical responses. Accordingly, the effects of water deficit on growth, essential oil and fatty acid composition of caraway (Carum carvi L.) seeds were investigated. Plants were treated with different levels of water deficit: control, moderate water deficit and severe water deficit. Plant growth (height, fresh and dry matter weight) was significantly reduced by severe water deficit. This last caused also important reductions of the seed yield and yield components. Drought decreased significantly seed total fatty acid contents and particularly the petroselinic ones whose proportions decreased significantly by 12.17 and 18.47%, in comparison with the control, under moderate water deficit and severe water deficit, respectively. Besides, moderate water deficit increased the essential oil yield (expressed as g/100 g on the basis of dry matter weight). The main essential oil constituents were carvone and limonene which showed an increasing of their contents under water deficit levels. Thus, water deficit induced a significant reduction in growth parameters and fatty acid content, and an increase in the essential oil compounds. These bioactive compounds have been required in many industrial products.     

Characteristics, chemical composition and utilisation of Albizia julibrissin seed oil

The physicochemical characteristics, fatty acid and triacylglycerol compositions, DSC profile and UV/vis spectrum of oil extracted from Albizia julibrissin seeds were determined in this study. The oil content and the moisture of the seeds were 10.50% and 1.56%. The free fatty acid, the peroxide value, the p-anisidine value, the saponification value, the iodine value were 2.54%, 6.61 mequiv. O₂/kg of oil, 1.98, 190.63 (mg KOH/g) and 111.33 (g/100 g of oil), respectively. The specific extinction coefficients K₂₃₂, K₂₆₈ were 7.55 and 0.96, respectively. Linoleic acid (C_18:2, 58.58%), palmitic acid (C₁₆, 13.86%) and oleic acid (C_18:1, 10.47%) were the dominant fatty acids in the A. julibrissin seed oil. LLL (36.87%), OLL (21.62%), PLL (16.69%) and PLO + SLL (8.59%) were the abundant triacylglycerol representing > 83% of the seed oil (L: linoleic, O: oleic, P: palmitic, S: stearic). The DSC melting curves reveal that: melting point = −14.70° C and melting enthalpy = 54.34 J/g. A. julibrissin seed oil showed some absorbance in the UV-B and UV-C ranges. The results of the present analytical study show that A. julibrissin is a promising oilseed crop, which can be used for making soap, hair shampoo and UV protectors. Furthermore, the high level of unsaturated fatty acids makes it desirable in terms of nutrition.     

Enzyme inhibitory and antioxidant activity of Melia azedarach L. naturalized in Anatolia and its phenolic acid and fatty acid composition

In the present study, acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and tyrosinase inhibitory and antioxidant activities of the fruit and leaf extracts of Melia azedarach L. (Meliaceae) of Turkish origin were evaluated. Enzyme inhibitory activity of the extracts was tested in vitro using ELISA microplate reader. Antioxidant activity of the extracts was tested using 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical scavenging, ferrous ion-chelation, and ferric-reducing antioxidant power (FRAP) assays. Phenolic composition of the extracts was elucidated by high performance liquid chromatography (HPLC) and fatty acid compositions of the fatty oils of the fruits and leaves were elucidated by gas chromatography-mass spectrometry (GC-MS). The ethyl acetate extract from the leaves showed the highest inhibition against AChE (33.63 ± 1.40%) and BChE (92.89 ± 3.05%). The methanol extract from the leaves exerted the best antioxidant activity in DPPH radical scavenging and FRAP assays, while the ethyl acetate extracts of the fruits and leaves had the most notable effect in metal-chelation assay.     

Chemical composition of the essential oil and antioxidant activity of methanolic extracts from fruits and flowers of Hypericum lydium Boiss.

This study was conducted to evaluate the essential oil composition and antioxidant activity of methanolic extracts from fruits and flowers of Hypericum lydium Boiss., a wild growing species of the Turkish flora. The antioxidant activities were determined through several biochemical assays. Both extracts showed an inhibitory effect against the formation of TBARS in a phosphatidylcholine liposome model system, moderate scavenging effect on DPPH and superoxide radicals, prominent reducing power and inhibitory effect on deoxyribose degradation in both the nonsite and site-specific assay, but a greater hydroxyl radical scavenging activity was observed in the non-site specific assay, suggesting that the extracts were better at scavenging hydroxyl radicals than at chelating iron. Correlation analysis indicated that there was a linear relationship between antioxidant potency, free-radical scavenging activity, reducing power and the content of flavonoids of fruits and flowers extracts. The essential oils obtained by hydrodistillation were analyzed by GC and GC-MS. In total forty-three compounds were identified. The most abundant components were monoterpenes hydrocarbons represented principally by α-pinene. The tested oil showed no antioxidant activity.     

Chemical variation in essential oil of Cryptomeria fortunei from various areas of China

Essential oils were extracted by hydrodistillation from the leaves of Cryptomeria fortunei from the principal habitats in China. The essential oil yields of samples from various locations ranged from 0.61 to 1.66% (w/w). GC-MS analysis revealed eighty-seven compounds, constituting 85.89-94.75% of the total essential oils. The main constituents were kaurene (0-44.69%), phyllocladene (0.07-32.98%), kaur-16-ene (0-32.28%), elemol (5.28-18.92%), α-cadinol (0-11.39%), α-eudesmol (0-11.21%), α-pinene (2.32-9.15%). The samples were separated into 3 chemotypes by hierarchical cluster analysis, according to the composition of the corresponding essential oils. Chemical composition of essential oils was significantly related to nine geographic distributions among populations. Our results revealed chemical polymorphism in the essential oils of the C. fortunei leaf in China. The chemical variability could be attributed to genetic and environmental factors. The chemical diversity of the oils offers opportunity to choose C. fortunei leaves and essential oils with preferential compound for green plant protection, pharmaceutical, perfume and food industries.     

Essential oil composition of Hypericum perfoliatum L. and Hypericum tomentosum L. growing wild in Tunisia

The essential oils obtained by hydrodistillation from the aerial parts of Tunisian native Hypericum perfoliatum L. (sect. Drosocarpium Spach.) and Hypericum tomentosum (sect. Adenosepalum Spach.) were analyzed by GC and GC–MS. Thirty-two compounds were identified in the essential oils of H. perfoliatum with α-pinene (13.1%), allo-aromadendrene (11.4%), germacrene-D (10.6%), n-octane (7.3%), α-selinene (6.5%) and β-selinene (5.5%) as main constituents. Sixty-seven components were identified in the oil of H. tomentosum with menthone (17.0%), n-octane (9.9%), β-caryophyllene (5.3%), α-pinene (5.2%), lauric acid (4.1%) and β-pinene (3.7%) as the most abundant components. Both oils were characterized by the presence of many components which could have numerous applications in food, pharmaceutical and perfume industries.     

Effect of drought on the biochemical composition and antioxidant activities of cumin (Cuminum cyminum L.) seeds

This study is designed to examine the yield components, fatty acid, and essential oil compositions and phenolic contents fruit essential oil composition, the total phenolic amounts as well as the antioxidant activities of cumin (Cuminum cyminum L.) seeds under drought. This plant is one of the most common aromatics in the Mediterranean kitchen. Plants were treated with different levels of water deficit: control (C), moderate water deficit (MWD) and severe water deficit (SWD). Our results indicated that MWD improved the number of umbels per plant as well as the number of umbellets per umbel and the seed yield, in comparison to the control, but it decreased under SWD. Fatty acid composition analysis indicated that petroselinic acid was the major fatty acid (55.9%) followed by palmitic (23.82%) and linoleic (12.40%) acids. Water deficit enhanced the palmitic acid percentage and affected the double bound index of the fatty acid pool and thus the oil quality. The essential oil yield was 1.64% based on the dry weight and increased by 1.40 folds under MWD. Nevertheless it decreased by 37.19% under SWD in comparison to the non treated seeds. Drought results on the modification of the essential oil chemotype from γ-terpinene/phenyl-1,2 ethanediol in the control seeds to γ-terpinene/cuminaldehyde in stressed ones. Besides, total phenolic contents were higher in the treated seeds (MWD and SWD). Results suggest that water deficit treatment may regulate the production of bioactive compounds in cumin seeds, influencing their nutritional and industrial values. Besides, antioxidant activities of the extracts were determined by four different test systems, namely DPPH, β-carotene/linoleic acid chelating and reducing power assays and showed that treated seeds (MWD and SWD) exhibited the highest activity.     

Discriminant analysis of selected yield components and fatty acid composition of chosen Triticum monococcum, Triticum dicoccum and Triticum spelta accessions

This study analyses the variability of key yield components, the content of protein and crude fat in grain and the fatty acid composition of 50 spring accessions of Triticum monococcum, Triticum dicoccum and Triticum spelta of various origins. The average protein content of the grain of T. monococcum was 20.8%, of T. dicoccum 19.7%, and of spelt 17.0%. The crude fat content of T. monococcum grain (2.7%) was significantly higher compared with T. spelta (2.4%) and T. dicoccum (2.3%). In crude fat, fatty acids C18:2, C18:1 and C16 predominated. T. spelta was characterised by the highest concentrations of C18:2 and C16 (55.89% and 18.77% respectively), while T. monococcum had the highest content of C18:1 (26.35%). The structure of analysed fatty acids proved to be highly desirable in this species. A discriminant analysis performed separately for five variables: protein and fat content and three biometrical characters and separately for fatty acid composition enabled three Triticum species to be distinguished. These species also differed significantly with respect to the C18:1/C16 ratio which was equal to 1.78, 1.06, 1.47 and 0.99 in T. monococcum, T. dicoccum, T. spelta and Triticum aestivum respectively.     

Changes in phytochemical, antimicrobial and free radical scavenging activities of the Peruvian pepper tree (Schinus molle L.) as influenced by fruit maturation

The effect of stage of maturity on total lipids, fatty acids, yields and essential oil composition and their antimicrobial and free radical scavenging activities of the Schinus molle fruits was investigated. The content of total lipids varied from 2.87 to 5.35% (w/w, dw) and were rich in unsaturated fatty acids particularly linoleic acid. As maturation progress, the essential oil yield dropped from 5.18% to 1.15%. Monoterpene hydrocarbons with α-phellandrene (35.15-40.38%), limonene + β-phellandrene (21.47-36.62%), β-myrcene (7.61-24.96%) and α-pinene (1.92-2.58%) were found to be the main components. At the same time, the essential oils were evaluated for their antimicrobial and free radical scavenging activities. They were found to be active against Bacillus subtilis, Bacillus cereus, Salmonella typhymurium and Escherichia coli but they do not inhibit the growth of Candida albicans. Conversely, they showed very weak activity against the DPPH radical. In both assay, the oil derived from the intermediate stage was reported as more efficient.     

Comparative analysis of essential oil components of two Cryptomeria species from China

The essential oils obtained by hydrodistillation from leaves of Chinese native Cryptomeria japonica and Cryptomeria fortunei were analyzed by GC and GC-MS. Fifty-seven compounds were identified in the essential oils of C. japonica with α-elemol (20.12%), kaur-16-ene (14.84%), β-phellandrene (5.97%), β-elemene (5.87%), α-eudesmol (5.62%) and β-eudesmol (5.03%) as main constituents. Forty components were identified in the oil of C. fortunei with kaurene (34.04%), α-elemol (13.34%), γ-eudesmol (10.80%), β-eudesmol (10.16%), α-pinene (2.75%) and γ-cadinene (1.92%) as the most abundant components. This study demonstrated the occurrence of α-elemol chemotype in C. japonica and kaurene chemotype in C. fortunei from China. The essential oil compositions of two Cryptomeria samples were shown that they can be used for green plant protection, pharmaceutical, perfume and food industries.     

Composition of essential oil, concrete, absolute and SPME analysis of Tagetes patula capitula

The chemical compositions of essential oil, concrete, absolute from the capitula of Tagetes patula (family Asteraceae) were analysed by GC-FID and GC/MS. The major compounds identified were (Z)-β-ocimene, (E)-β-ocimene, terpinolene, (Z)-ocimenone, (E)-ocimenone and δ-elemene. In addition, the volatiles of live and plucked capitula (flowers) were analysed by SPME technique using PDMS/DVB/CAR fiber. The SPME-GC-FID analyses of live capitula showed that the volatiles were rich in monoterpenoids in comparison to the plucked capitula. On the other hand, the plucked capitula recorded with significant increase in sesquiterpenoids in comparison to the living capitula.     

Antifungal and antiaflatoxigenic efficacy of Caesulia axillaris Roxb. essential oil against fungi deteriorating some herbal raw materials, and its antioxidant activity

The study deals with evaluation of antifungal and antiaflatoxigenic Caesulia axillaris Roxb. essential oil (EO) against herbal raw materials deteriorating fungi and its free radical scavenging activity. During mycoflora analysis these herbal raw materials were found to be severely contaminated by different fungi and aflatoxins. A total of nine different fungal species were isolated from three herbal raw materials. Aspergillus flavus LHPtc was recorded as the highest aflatoxin B1 producing strain. EOs of some plants were tested for their fungitoxicity against the toxigenic strain A. flavus LHPtc, and C. axillaris EO was found as potent fungitoxicant. C. axillaris EO was chemically characterized through GC-MS analysis which depicted the presence of 18 compounds, dl-limonene and Euasarone being the major components. The EO exhibited broad spectrum of fungitoxicity against fungi causing postharvest deterioration of herbal raw materials. At 1.0 μl ml⁻¹ the oil showed complete inhibition of fungal growth and aflatoxin B₁ production was inhibited at 0.8 μl ml⁻¹. Free radical scavenging activity of the oil was also recorded by 2,2-diphenyl-1-picrylhydrazyl assay, and its IC₅₀ value was found 18 μl ml⁻¹. The safety limit of the EO was determined in terms of LD₅₀ on mice, which was 9166.6 μl kg⁻¹, suggesting its non mammalian toxicity. The EO of C. axillaris may be recommended as a plant based preservative in enhancement of shelf life of herbal raw materials by preventing their lipid peroxidation as well as biodeterioration due to fungal and aflatoxin contamination.     

Improvement of essential oil yield of oil-bearing (Rosa damascena Mill.) due to surfactant and maceration

The essential oil content of the oil-bearing rose (Rosa damascene Mill.) is relatively low, around 0.3-0.4 mL kg⁻¹ in fresh flowers. There is a need to increase essential oil yield of oil-bearing rose. The objective was to examine the effect of Tween 20 (polyoxyethylene sorbitan monolaurate) applied with, or without, maceration of flowers on oil content and composition of oil-bearing rose harvested at beginning of flowering, full bloom, and end of flowering. Addition of Tween 20 at 1000 mL L⁻¹ and 2500 mL L⁻¹ increased essential oil yield by 26% (to 0.44 mL kg⁻¹) and 54% (to 0.54 mL kg⁻¹) respectively relative to the untreated control that gave 0.35 mL kg⁻¹ yield. Maceration, in combination with the addition of Tween 20 at 1000 mL L⁻¹ and Tween 20 at 2500 mL L⁻¹, increased oil yield by 69% (to 0.59 mL kg⁻¹) and 94% (to 0.68 mL kg⁻¹) respectively. Among the three phenological phases of harvest, harvesting at the beginning of flowering gave the highest yield followed by the full bloom and then by the end of flowering phases. Since the interaction effect was not significant, the differences obtained among the treatments were regardless of the phase, and vice versa. Treatments did not significantly alter composition of the essential oil. Postharvest pre-extraction application of Tween 20 in combination with maceration could be used in the rose industry for increasing the essential oil yield.     

Variability in essential oil content and composition of Origanum hirtum L., Origanum onites L., Coridothymus capitatus (L.) and Satureja thymbra L. populations from the Greek island Ikaria

Plants belonging to four “oregano” plant species (Origanum hirtum L., Origanum onites L., Coridothymus capitatus L., and Satureja thymbra L.) were collected during flowering from 33 sites located in the eastern part of the Greek island of Ikaria in the Eastern Aegean during April, May and July 2008. C. capitatus and O. hirtum were mostly observed in higher altitudes, whereas O. onites and S. thymbra in lower ones. The spatial distribution of all species was depicted on a GIS map. All four species exhibited essential oil concentrations higher than those reported in earlier literature, namely O. onites 3-4.3%, S. thymbra 4-6.5%, C. capitatus 3.7-5.6% and O. hirtum 5.5-10.0% (v/w). Carvacrol was the main constituent of the essential oils of all species, followed by γ-terpinene, p-cymene and caryophyllene, while thymol was not detected. All constituents varied remarkably among the four species, with carvacrol exhibiting the lowest variation. Carvacrol content varied between 72.3 and 89.2% in O. onites; 46.5 and 58.0% in S. thymbra; 82.9 and 90.9% in C. capitatus; and 84.4 and 93.8% in O. hirtum. By applying hierarchical cluster analysis on the basis of the essential oil constituents two main groups, divided into four subgroups of the taxa were evident. The first group consisted of O. onites and S. thymbra, while the second one of C. capitatus and O. hirtum. The results are discussed in terms of topography and climatic variation.     

Mathematical modeling for extraction of essential oil from Baccharis spp. by steam distillation

Baccharis (Compositae-Asteraceae) is a large genus of plants distributed from the USA to Argentina, of which 90% are located in South America. In recent decades, species of the genus have been studied, due to their importance as sources of novel active components with possible applications in the pharmaceutical and chemical industries. This work studied three species of Baccharis: Baccharis uncinella DC, Baccharis anomala DC and Baccharis dentata (Vell) G.M. Barroso collected in São Francisco de Paula in southern Brazil. The aim of this work is the evaluation of the aromatic potential of the essential oil obtained by steam distillation method and the simulation of the extraction data by means of a mathematical model. A mathematical model based on mass transfer fundamentals is developed and applied to correlate the experimental data. This model is based on the existence of the broken and intact cells, in which the oil located in the broken cells is rapidly extracted and the oil from intact cells diffuses slowly to the surface of the vegetal material. The analysis of the essential oil was carried through by GC-MS and the major compounds identified to both processes were α-pinene, β-pinene, and spathulenol (B. uncinella), spathulenol, β-caryophyllene, and β-selinene (B. anomala), and germacrene-D, caryophyllene oxide, and spathulenol (B. dentata).     

European pennyroyal (Mentha pulegium) from Portugal: Chemical composition of essential oil and antioxidant and antimicrobial properties of extracts and essential oil

There is a growing interest of industry to replace synthetic chemicals by natural products with bioactive properties from plant origin. The aim of this study was to determine the chemical composition of European pennyroyal (Mentha pulegium) essential oil and to characterize the in vitro antioxidant and antimicrobial activities of its water (hot and cold) and ethanolic extracts and of the essential oil. The essential oil revealed menthone, pulegone and neo-menthol as the main constituents, comprising 35.9, 23.2 and 9.2% of the essential oil, respectively. The hot water extract exhibited the highest antioxidant activity and phenol content. In contrast, the extracts were not very effective to inhibit the growth of the seven foodborne spoilage and pathogenic bacteria tested, but the essential oil showed antibacterial activity against all bacterial strains. In conclusion, extracts and essential oil of M. pulegium from Mediterranean origin have huge potential as an alternative to chemical additives for the food industry.