Comparison of eucalyptus camaldulensis Dehn. oils from Mozambique as obtained by hydrodistillation and supercritical carbon dioxide extraction

Leaf oils of E. camaldulensis Dehn. from Mozambique obtained by hydrodistillation and by supercritical carbon dioxide extraction under different conditions were compared with regard to their major components. The oil obtained by hydrodistillation showed high concentrations of 1,8-cineole (43%), alpha-pinene (5.5%), beta-pinene (3.4%), p-cymene (5.2%), terpinen-4-ol (3.1%), and globulol (4.1%). The extracts obtained by supercritical carbon dioxide extraction have lower amounts of 1,8-cineole, alpha-pinene, beta-pinene, and terpinen-4-ol, but have higher amounts of allo-aromadendrene and globulol. At the same time, distilled oil of E. radiata was extracted from an inert matrix (Celite) and the extract showed a higher content of 1,8-cineole at 80 bar and 60 degrees C than the feed, suggesting that a multiple-stage supercritical carbon dioxide extraction of the E. camaldulensis studied can produce an oil close to the market requirements set by the European pharmacopoeias.     

Chemical composition and antioxidant properties of clove leaf essential oil

The antioxidant activity of a commercial rectified clove leaf essential oil (Eugenia caryophyllus) and its main constituent eugenol was tested. This essential oil comprises in total 23 identified constituents, among them eugenol (76.8%), followed by beta-caryophyllene (17.4%), alpha-humulene (2.1%), and eugenyl acetate (1.2%) as the main components. The essential oil from clove demonstrated scavenging activity against the 2,2-diphenyl-1-picryl hydracyl (DPPH) radical at concentrations lower than the concentrations of eugenol, butylated hydroxytoluene (BHT), and butylated hydroxyanisole (BHA). This essential oil also showed a significant inhibitory effect against hydroxyl radicals and acted as an iron chelator. With respect to the lipid peroxidation, the inhibitory activity of clove oil determined using a linoleic acid emulsion system indicated a higher antioxidant activity than the standard BHT.     

Melanin synthesis inhibitors from Balanophora fungosa

Tyrosinase, trypsin, and tryptase are known to play important roles in melanin production of human skin. This paper describes the study of the inhibitory effect of Balanophora fungosa on melanin. The 50% EtOH extract obtained from B. fungosa indicated an inhibitory effect on mushroom tyrosinase activity with an IC(50) value of 15 μg/mL. Bioassay-guided fractionation of the active extract resulted in the isolation of four known compounds. Their structures were identified as 1-O-(E)-caffeoyl-3-O-galloyl-4,6-(S)-HHDP-β-d-glucopyranose (1), 1-O-(E)-caffeoyl-3,4,6-tri-O-galloyl-β-d-glucopyranose (2), caffeoyl-β-d-glucopyranose (3), and abietin (4) on the basis of spectroscopic analyses and comparison of their spectral data with those in the literature. Compounds 1 and 2 prevented pigmentation of melanin in a three-dimensional cultured human skin model. Furthermore, compounds 1 and 2 indicated inhibitory activities against trypsin and tryptase.     

In vitro activity of the essential oil of Cinnamomum zeylanicum and eugenol in peroxynitrite-induced oxidative processes

The essential oil obtained from the bark of Cinnamomum zeylanicum Blume (Lauraceae) and three of its main components, eugenol, (E)-cinnamaldehyde, and linalool (representing 82.5% of the total composition), were tested in two in vitro models of peroxynitrite-induced nitration and lipid peroxidation. The essential oil and eugenol showed very powerful activities, decreasing 3-nitrotyrosine formation with IC50 values of 18.4 microg/mL and 46.7 microM, respectively (reference compound, ascorbic acid, 71.3 microg/mL and 405.0 microM) and also inhibiting the peroxynitrite-induced lipid peroxidation showing an IC50 of 2.0 microg/mL and 13.1 microM, respectively, against 59.0 microg/mL (235.5 microM) of the reference compound Trolox. On the contrary, (E)-cinnamaldehyde and linalool were completely inactive.     

Essential oil and volatile emissions of basil (Ocimum basilicum) leaves exposed to NaCl or Na2SO4 salinity

The volatile compounds emitted by living leaves of basil (Ocimum basilicum L. cv. Genovese) plants under saline conditions were investigated by means of headspace–solid phase microextraction (HS‐SPME) and gas chromatography coupled with mass spectrometry (GC–MS). Furthermore, the composition of the essential oil obtained by hydrodistillation of the leaves was studied. Plants were grown for 15 d without salt or with an equimolar concentration of Na⁺ in the form of Na₂SO₄ (25 mM) and NaCl (50 mM), after which the growth, the essential oil, and the volatile constituents of the leaves were determined. Fifty‐four components were identified belonging to different chemical classes. Under control conditions, the essential oil was rich in linalool (45.9%), 1,8‐cineole (16.7%), eugenol (10.3%), trans‐α‐bergamotene, and epi‐α‐cadinol (4.9%). The main volatiles detected in the headspace of leaves of untreated basil plants were linalool (29.8%), followed by 1,8‐cineole (19.2%), trans‐α‐bergamotene (10.0%), and eugenol (7.0%). Under saline conditions, leaf growth was more depressed by 25 mM Na₂SO₄ than 50 mM NaCl, and essential oil concentration increased by 22% in the NaCl, but decreased by 18% in the Na₂SO₄ treatment, respectively. Both salts caused some changes in the essential oil and composition of volatile compounds. Most prominent was a strong negative correlation between eugenol and methyleugenol proportions, which may indicate an enhancement of the O‐methyltransferase activity. In comparison to the essential oil, the composition of volatiles showed some variations in their emission profile under both salts, the most important was an increase of eugenol. It is therefore concluded that the decrease of eugenol occurring in basil essential oil caused by both salts could be due to the enhancement of the eugenol O‐methyltransferase activity, an enzyme that accepts eugenol as substrate, generating methyl eugenol, and also to the increase of the eugenol emission as shown by the SPME profile.     

Chemical characterization of aroma compounds in essential oil isolated from “Holy Basil” (Ocimum tenuiflorum L.) grown in India

Ocimum tenuiflorum L. (“Holy Basil”/“Tulsi”) is an indigenous Ayurvedic medicinal plant of India, widely distributed in tropical and warm temperate regions. Plant is well known for its enormous therapeutic activities and prevention against diseases. In the present study, thirty-two accessions of O. tenuiflorum germplasm collected from different regions of Northern India were evaluated for their essential oil content and composition. Essential oil obtained by hydrodistillation was analyzed by GC and GC/MS for aroma compounds. Essential oil content in O. tenuiflorum germplasm showed wide range of variation from 0.13 to 0.45 % on FWB. GC and GC/MS profile of O. tenuiflorum oil showed phenylpropanoids, mainly eugenol constituted the major proportion of essential oil. The range of major chemical constituents identified were eugenol (1.94–60.20 %), methyl eugenol (0.87–82.98 %), β-caryophyllene (4.13–44.60 %), β-elemene (0.76–32.41 %). Eugenol and methyl eugenol rich two chemotypes were identified in O. tenuiflorum germplasm. The accessions, IC583281, IC583285 and IC583322 were found to contain high eugenol content (>55 %), while three accessions IC583279, IC583284 and IC583278 were found to possess high methyl eugenol content (>70 %). Eugenol has been reported to be largely responsible for the therapeutic potentials of tulsi, while methyl eugenol is a high value aroma chemical used as flavouring agent. The results suggest holy basil have a potential as a new essential oil crops and can provide oil yields and composition typical for the respective species.     

Composition and Antimicrobial Activity of Anemopsis californica leaf oil

Isolation and characterization of leaf volatiles in Anemopsis californica (Nutt.) Hook. and Arn. (A. californica) was performed using steam distillation, solid-phase microextraction, and supercritical fluid extraction. Thirty-eight compounds were detected and identified by gas chromatography; elemicin was the major component of the leaf volatiles. While the composition of the leaf volatiles varied with method of extraction, alpha-pinene, sabinene, beta-phellandrene, 1,8-cineole, piperitone, methyl eugenol, (E)-caryophyllene, and elemicin were usually present in readily detectable amounts. Greenhouse-reared clones of a wild population of A. californica had an identical leaf volatile composition with the parent plants. Steam-distilled oil had antimicrobial properties against 3 (Staphylococcus aureus, Streptococcus pneumoniae, and Geotrichim candidum) of 11 microbial species tested. Some of this bioactivity could be accounted for by the alpha-pinene in the oil.     

Antibacterial activities of plant essential oils and their components against Escherichia coli O157:H7 and Salmonella enterica in apple juice

We evaluated 17 plant essential oils and nine oil compounds for antibacterial activity against the foodborne pathogens Escherichia coli O157:H7 and Salmonella enterica in apple juices in a bactericidal assay in terms of % of the sample that resulted in a 50% decrease in the number of bacteria (BA(50)). The 10 compounds most active against E. coli (60 min BA(50) range in clear juice, 0.018-0.093%) were carvacrol, oregano oil, geraniol, eugenol, cinnamon leaf oil, citral, clove bud oil, lemongrass oil, cinnamon bark oil, and lemon oil. The corresponding compounds against S. enterica (BA(50) range, 0.0044-0.011%) were Melissa oil, carvacrol, oregano oil, terpeineol, geraniol, lemon oil, citral, lemongrass oil, cinnamon leaf oil, and linalool. The activity (i) was greater for S. enterica than for E. coli, (ii) increased with incubation temperature and storage time, and (iii) was not affected by the acidity of the juices. The antibacterial agents could be divided into two classes: fast-acting and slow-acting. High-performance liquid chromatography analysis showed that the bactericidal results are related to the composition of the oils. These studies provide information about new ways to protect apple juice and other foods against human pathogens.     

Composition and functional properties of the essential oil of amazonian basil, Ocimum micranthum Willd., Labiatae in comparison with commercial essential oils

Wild Amazonian basil Ocimum micranthum Willd. (O. campechianum Mill.) Labiatae essential oil was analyzed by GC and GC-MS: 31 compounds were identified. The main components were eugenol (46.55 +/- 5.11%), beta-caryophyllene (11.94 +/- 1.31%), and beta-elemene (9.06 +/- 0.99%), while a small amount of linalool (1.49 +/- 0.16%) was detected. The oil was tested for its in vitro food-related biological activities and compared with common basil Ocimum basilicum and Thymus vulgaris commercial essential oils. Radical scavenging activity was evaluated employing 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay. The oil exerted a good capacity to act as a nonspecific donor of hydrogen atoms or electrons when checked in the diphenylpicrylhydrazyl assay, quenching 76,61 +/- 0.33% of the radical, with values higher than those reported by reference oils. In the beta-carotene bleaching test, the oil provided an antioxidant efficacy comparable with that of O. basilicum and T. vulgaris essential oils. These data were confirmed by photochemiluminescence, where the oil showed a remarkable antioxidant capacity (2.39 +/- 0.1), comparable to that of Trolox and vitamin E, and higher than the other essential oils. Antibacterial activity of O. micranthum essential oil was evaluated against Gram positive and Gram negative bacterial strains. The oil showed a dose-dependent antifungal activity against pathogenic and food spoiling yeasts.     

Content, composition, and bioactivity of the essential oils of three basil genotypes as a function of harvesting

A study was conducted to evaluate the effect of cut on biomass productivity, oil content, composition, and bioactivity of Ocimum basilicum L. (cvs. German and Mesten) and Ocimum sanctum L. (syn. O. tenuiflorum L.) (cv. Local) in Mississippi. Yields of basil herbage and essential oil were high and comparable to those reported in the literature. Essential oil content of O. basilicum cv. German varied from 0.40 to 0.75%, the oil content of cv. Mesten varied from 0.50 to 0.72%, and the oil content of cv. Local (of O. sanctum) ranged from 0.17 to 0.50% in air-dried basil. Herbage and essential oil yields of cvs. German and Mesten of O. basilicum increased with the second and then again with the third cut, whereas herbage and oil yields of cv. Local of O. sanctum increased with the third cut relative to the previous cuts. Overall, essential oil yields were 115, 123, and 51 kg/ha for the cvs. German, Mesten, and Local, respectively. The major oil constituents of cvs. German and Mesten (of O. basilicum) were (-)-linalool (30-40%) and eugenol (8-30%), whereas the major oil constituents of cv. Local (of O. sanctum) were eugenol (8-43%) and methylchavicol (15-27%). Essential oils from both species grown in Mississippi showed in vitro activity against Leishmania donovani (IC50 = 37.3-49.6 microg/mL), which was comparable to the activity of commercial oil (IC50 = 40-50 microg/mL). Minor basil oil constituents (+)-delta-cadinene, 3-carene, alpha-humulene, citral, and (-)- trans-caryophyllene had antileishmanial activity, whereas other constituents were ineffective. None of the oil was cytotoxic to mammalian cells.     

Glabrene and isoliquiritigenin as tyrosinase inhibitors from licorice roots

Tyrosinase is known to be a key enzyme in melanin biosynthesis, involved in determining the color of mammalian skin and hair. Various dermatological disorders, such as melasama, age spots, and sites of actinic damage, arise from the accumulation of an excessive level of epidermal pigmentation. The inadequacy of current therapies to treat these conditions as well as high cytotoxicity and mutagenicity, poor skin penetration, and low stability of formulations led us to seek new whitening agents to meet the medical requirements for depigmenting agents. The inhibitory effect of licorice extract on tyrosinase activity was higher than that expected from the level of glabridin in the extract. This led us to test for other components that may contribute to this strong inhibitory activity. Results indicated that glabrene and isoliquiritigenin (2',4',4-trihydroxychalcone) in the licorice extract can inhibit both mono- and diphenolase tyrosinase activities. The IC(50) values for glabrene and isoliquiritigenin were 3.5 and 8.1 microM, respectively, when tyrosine was used as substrate. The effects of glabrene and isoliquiritigenin on tyrosinase activity were dose-dependent and correlated to their ability to inhibit melanin formation in melanocytes. This is the first study indicating that glabrene and isoliquiritigenin exert varying degrees of inhibition on tyrosinase-dependent melanin biosynthesis, suggesting that isoflavenes and chalcones may serve as candidates for skin-lightening agents.     

Chemical composition of the volatile extract and antioxidant activities of the volatile and nonvolatile extracts of Egyptian corn silk (Zea mays L.)

A total of 36 compounds, which comprised 99.4% of the extract, were identified by gas chromatography and mass spectrometry (GC-MS) in the volatile dichloromethane extract obtained from Egyptian corn silk. The main constituents of the volatile extract were cis-alpha-terpineol (24.22%), 6,11-oxidoacor-4-ene (18.06%), citronellol (16.18%), trans-pinocamphone (5.86%), eugenol (4.37%), neo-iso-3-thujanol (2.59%), and cis-sabinene hydrate (2.28%). Dried Egyptian corn silk was also directly extracted with petroleum ether, ethanol, and water. All extracts from solvent extraction and the volatile extract described above exhibited clear antioxidant activities at levels of 50-400 microg/mL in the 2,2-diphenyl-1-picrylhydrazyl (DPPH)/linoleic acid assay. The ethanol extract inhibited DPPH activity by 84% at a level of 400 microg/mL. All samples tested via the beta-carotene bleaching assay also exhibited satisfactory antioxidant activity with clear dose responses. This study indicates that corn silk could be used to produce novel natural antioxidants as well as a flavoring agent in various food products.     

Phytosterol and tocopherol components in extracts of corn distiller's dried grain

As the ethanol industry continues to grow, it will become very important to develop value-added markets for its coproducts in order for the industry to remain profitable. Corn distiller's dried grain (DDG) is a major coproduct of ethanol fermentation from corn processed by dry-milling and is primarily sold as livestock feed. The objective of this research was to determine if valuable phytochemicals found in corn oil and corn fiber oil, such as phytosterols and their saturated equivalents, phytostanols, ferulate phytosterol esters (FPE), tocopherols, and tocotrienols, are retained in DDG. Hexane and supercritical carbon dioxide (CO2) extracts of DDG were similar in their concentrations of total phytosterols (15.8-17.3 mg/g of extract), FPE (3.75-3.99 mg/g of extract), and tocols (1.7-1.8 mg/g of extract). Ethanol extracts were slightly lower in concentration of phytosterols (8.9-11.4 mg/g of extract), FPE (1.62-1.98 mg/g of extract), and tocols (0.73-0.76 mg/g of extract).     

Chemical composition and antimicrobial and antioxidant activities of the essential oil and methanol extract of Hippomarathrum microcarpum (Bieb.) from Turkey

Hippomarathrum microcarpum grows wild in eastern Anatolia, Turkey, and is a plant utilized as food by people. In this study, the in vitro antimicrobial and antioxidant activities of the essential oil and methanol extract from H. microcarpum and its essential oil composition were investigated. The essential oil, which has bornyl acetate, caryophyllene oxide, and beta-caryophyllene as its main components, exhibited activity against eight bacteria, nine fungi, and a yeast, Candida albicans, with minimum inhibitory concentration values ranging from 62.50 to 125 muL/mL; the methanol extract showed weak activity. The antioxidant activity of these extracts was assessed by the beta-carotene bleaching test and the 1,1'-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging test. The inhibition of linoleic acid oxidation was very weak for both extracts tested. The inhibition percentages were found to be 22.9 and 33.5% for methanol and essential oil, respectively, at the concentration of 2 g/L. The oil scavenged DPPH at higher concentrations (IC50 = 10.69 +/- 0.05 mg/mL), but the methanol extract exhibited no activity. The total phenolic content of the methanol extract was found to be 4.7 +/- 0.1%.     

Improved malonaldehyde assay using headspace solid-phase microextraction and its application to the measurement of the antioxidant activity of phytochemicals

A modified malonaldehyde (MA) assay for antioxidant activity, which involves derivatization and headspace solid-phase microextraction (HS-SPME) was developed and validated. The recovery of MA as 1-methylpyrazole (product of MA and N-methylhydrazine) from a headspace of an aqueous solution containing MA, buffer, surfactant, and cod liver oil using HS-SPME with a PDMS/DVB fiber was 91.3 +/- 3.38%. MA was analyzed by a gas chromatograph with a nitrogen-phosphorus detector, and its detection limit was 0.0103 nmol/mL. The antioxidant activities of natural compounds were determined as the percentage inhibition of MA formed from cod liver oil oxidized by Fenton's reagents in the above aqueous solution. Sesamol inhibited MA formation most (86.1%), followed by eugenol (84.4%), capsaicin (80.7%), ethylvanillin (45.3%), and vanillin (31.6%) at a level of 50 microg/mL. This method did not require any organic solvents and is a simple, fast, and a highly sensitive method for MA determination.     

Antioxidant properties of aroma compounds isolated from soybeans and mung beans

Aroma compounds contained in the extracts of soybean and mung bean that possess antioxidant activity were identified by gas chromatography (GC) and gas chromatography/mass spectrometry (GC/MS). The major aroma constituents of soybeans were 1-octen-3-ol (13.699 ppm), maltol (1.662 ppm), phenylethyl alcohol (1.474 ppm), hexanol (1.430 ppm), and gamma-butyrolactone (1.370 ppm). The major aroma constituents of mung beans were hexanol (3.234 ppm), benzyl alcohol (2.060 ppm), gamma-butyrolactone (1.857 ppm), 2-methyl-2-propenal (1. 633 ppm), and pentanol (1.363 ppm). The major aroma chemicals of soybeans and mung beans were examined for antioxidative activities in two different assays. Eugenol, maltol, benzyl alcohol, and 1-octen-3-ol showed potent antioxidative activities in two different assays. Eugenol, maltol, benzyl alcohol, and 1-octen-3-ol inhibited the oxidation of hexanal by 100%, 93%, 84%, and 32%, respectively, for a period of 40 days at the 500 microg/mL level. Eugenol, maltol, benzyl alcohol, and 1-octen-3-ol inhibited malonaldehyde (MA) formation from cod liver oil by 91%, 78%, 78%, and 78%, respectively, at the 160 microg/mL level. The antioxidative activity of eugenol was comparable to that of the natural antioxidant alpha-tocopherol (vitamin E).     

Effect of methyl jasmonate on secondary metabolites of sweet basil (Ocimum basilicum L.)

The effect of methyl jasmonate (MeJA) in terms of its induction of inherent bioactive chemicals in sweet basil (Ocimum basilicum L.) was evaluated after MeJA was sprayed on healthy basil plants. The total phenolic content of the sweet basil significantly increased after 0.1 and 0.5 mM MeJA treatments compared with the control not subjected to MeJA. Two phenolic compounds, rosmarinic acid (RA) and caffeic acid (CA), were identified as strong antioxidant constituents of the sweet basil. Their amounts also significantly increased after the MeJA treatment. In addition, eugenol and linalool increased 56 and 43%, respectively, by the 0.5 mM MeJA treatment. Due to the accumulation of RA, CA, and eugenol, which possess strong 2,2-diphenyl-1-picrylhydrazyl (DPPH*) free radical scavenging activities, the antioxidant activity of the sweet basil extract was 2.3-fold greater than that of the control after the 0.5 mM MeJA treatment. In the DPPH* assay, the EC50 values of RA, CA, and eugenol were determined as 23, 46, and 59 microM, respectively, which indicated they were 6-, 3-, and 2.4-fold more efficient than BHT (140 microM). Besides, an unidentified HPLC peak in the methanolic extract of the sweet basil was 4.3-fold higher than that of the control after the 0.5 mM MeJA treatment.     

Identification and quantification of impact odorants of aged red wines from Rioja. GC-olfactometry, quantitative GC-MS, and odor evaluation of HPLC fractions.

An XAD-4 extract from a 5-year-old wine from Rioja (Spain) was analyzed by aroma extract dilution analysis. Most of the odorants were quantified by GC-MS. A second extract was fractionated in an HPLC system with a C-18 semipreparative column. Fifty fractions were recovered, their alcoholic degree and pH were further adjusted to those of the wine, and those fractions that showed strong odor characteristics were further re-extracted and analyzed by GC-O and GC-MS. Reconstitution experiments were carried out to confirm the role of the odorants detected in the fractions. Fifty-eight odorants were found in the Rioja wine, 52 of which could be identified. Methyl benzoate was found to be a wine aroma constituent for the first time. The most important odorants are 4-ethylguaiacol, (E)-whiskey lactone, 4-ethylphenol, beta-damascenone, fusel alcohols, isovaleric and hexanoic acids, eugenol, fatty acid ethyl esters, and ethyl esters of isoacids, Furaneol, phenylacetic acid, and (E)-2-hexenal. Comparison among the three techniques shows good agreement and demonstrates that they are complementary.     

In vitro antimicrobial and antioxidant activities of the essential oils and various extracts of Thymus eigii M. Zohary et P.H. Davis

This study was designed to examine the in vitro antimicrobial and antioxidant activities of the essential oil and various extracts obtained from aerial parts of Thymus eigii. The essential oil was particularly found to possess stronger antimicrobial activity, whereas other nonpolar extracts and subfractions showed moderate activity and polar extracts remained almost inactive. GC-MS analysis of the oil resulted in the identification of 39 compounds, representing 93.7% of the oil; thymol (30.6%), carvacrol (26.1%), and p-cymene (13.0%) were the main components. The samples were also subjected to a screening for their possible antioxidant activity by using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and beta-carotene-linoleic acid assays. In the former case, the polar subfraction of the methanol extract was found to be superior to all extracts tested, only 16.8 microg/mL of which provided 50% inhibition, whereas all extracts, particularly the polar ones, seem to inhibit the oxidation of linoleic acid in the latter case. These data were further supported by total phenolics analysis, indicating that the antioxidative potential of the extracts was closely related to their phenolic constituents.     

Suppression effect of Cinnamomum cassia bark-derived component on nitric oxide synthase

The inhibitory effects of Cinnamomum cassia bark-derived material on nitric oxide (NO) production in RAW 264.7 cells was determined through the evaluation of NO production and expression of inducible nitric oxide and compared to the effects of three commercially available compounds, cinnamyl alcohol, cinnamic acid, and eugenol. The biologically active constituents of C. cassia extract were characterized as trans-cinnamaldehyde by spectral analysis. The inhibitory effects varied with both chemical and concentration used. Potent inhibitory effects of cinnamaldehyde against NO production were 81.5 and 71.7% at 1.0 and 0.5 microg/microL, respectively, and a 41.2% inhibitory effect was revealed at 0.1 microg/microL. However, little or no activity was observed for cinnamic acid and eugenol. Suppression effects of cinnamaldehyde on inducible nitric oxide synthase expression were revealed by Western blot analysis. As a naturally occurring therapeutic agent, trans-cinnamaldehyde could be useful for developing new types of NO inhibitors.