Antioxidative properties of Thymus vulgaris leaves: comparison of different extracts and essential oil chemotypes

Thyme (Thymus vulgaris L., Lamiaceae) is a subshrub from the Lamiaceae family with plants that are rich in essential oils and antioxidative phenolic substances. Twelve accessions originating from southern France and the variety 'Deutscher Winter' were grown in an experimental field in eastern Austria. Leaf samples from these plants as well as from a commercial thyme rich in thymol were analyzed for their essential oil and the antioxidative potential in various extracts. The assays for antioxidative activity were the total phenolics according to the Folin-Ciocalteu method, DPPH decoloration, and Fe(3+) reduction (FRAP). Both extraction techniques used, in the water bath at 40 degrees C and in the ultrasonic bath at room temperature, proved to be efficient. The best results were obtained with 60% ethanol as extractant. In the comparison of the different accessions the less active and the most active of these extracts differed by factors of 2.1 and 2.6 in the total phenolics and FRAP assay, respectively, and by factors 1.5-2.0 in the DPPH assay. Rosmarinic acid accounted for 22-55% of the antioxidant activity in the ethanolic extracts. Essential oils with high proportions of the phenolic components thymol and/or carvacrol showed the highest antioxidant activity. Ethanolic extracts from the residues after distillation were considerably lower in antioxidant activity than the respective extracts from the dried leaves. Extracts with CH2Cl2 in the ultrasonic bath contained volatiles in proportions close to the essential oil but displayed very low antioxidant activity.     

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.     

Antioxidative properties of phenolic antioxidants isolated from corn steep liquor

With the immersion of corn into dilute sulfur oxide during starch-manufacturing processes, corn steep liquor (CSL) remains as leftover material. CSL is often used for fermentation, but its components are not fully understood. To determine the properties of CSL, 12 p-coumaric acid-related compounds were isolated from an ethyl acetate extract of CSL with the guidance of antioxidative activity on the rabbit erythrocyte membrane ghost system. The activity of these compounds was compared against oxidative damages, and it was elucidated that the activity of p-coumaric acid derivatives was mainly affected by their functional groups at the 3-position and less by the conjugated side chain. Moreover, p-coumaric acid derivatives exhibited inhibitory activity stronger than that of tocopherols and ascorbic acid on peroxynitrite-mediated lipoprotein nitration. These findings that p-coumaric acid derivatives, which might play a beneficial role against oxidative damage, exist in CSL suggest this byproduct might be a useful resource of phenolic antioxidants.     

薰衣草精油改善壳聚糖基食品包装膜的应用品质

为改善现有壳聚糖基食品包装膜的机械性能和防水性能,该文使用浇铸-蒸发-碱浸法制备了添加薰衣草精油的壳聚糖基复合膜。采用红外光谱、X射线衍射对膜进行了表征,并分析了薰衣草精油添加量对膜的厚度、机械性质、可挥发物质量分数、接触角、水溶性、溶胀性等性质的影响。结果表明:薰衣草精油成分占据了壳聚糖骨架中的部分官能团的位置,降低了壳聚糖分子中共价键的振动强度,同时膜中可以与水形成亲水键的自由H基团减少,膜的含水量降低。薰衣草精油的添加,增大了膜中壳聚糖乙酸盐的含量。膜的厚度和薰衣草精油添加量并不成线性关系,所得膜的厚度范围为(20.60±0.34)~(23.35±0.65)μm。随着薰衣草精油添加量的增加,膜的拉伸强度和断裂伸长率的变化趋势基本相同。当薰衣草精油添加量为8%时,拉伸强度和断裂伸长率都达到最大值,分别为(123.44±0.33)MPa和3.74%±0.02%。与壳聚糖膜相比,薰衣草精油/壳聚糖复合膜的的可挥发物质量分数较低,薰衣草精油添加量为2%时,可挥发物质量分数最低,为8.98%±0.05%。薰衣草精油的添加,增大了膜的溶解性,但膜在水中的溶解度均不大于(1.21±0.04)mg/100 g,属于难溶物质范畴。膜的接触角和溶胀指数都随薰衣草精油添加量的增加而减小,即当薰衣草精油添加量为10%时,膜的接触角和溶胀指数都达到最大值,分别为80.73°±0.32°和0.62±0.01。薰衣草精油的加入改善了由浇铸-蒸发-碱浸法制备的CS基复合膜的机械性质和物理性质。研究结果为薰衣草精油/壳聚糖复合膜的生产和应用提供了技术依据。     

Study on the antiinflammatory activity of essential oil from leaves of Cinnamomum osmophloeum

The leaf essential oil from indigenous cinnamon (Cinnamomum osmophloeum Kaneh.) was investigated by gas chromatography-mass spectrometry, and 21 compounds were identified. The major constituents of leaf essential oil were the monoterpenes 1,8-cineole (17.0%) and santolina triene (14.2%) and the sesquiterpenes spathulenol (15.7%) and caryophyllene oxide (11.2%). In the antiinflammatory activity assay, we demonstrated that the essential oil has a higher capacity to inhibit proIL-1beta protein expression induced by LPS-treated J774A.1 murine macrophage. At dosages of 60 microg/mL, essential oil clearly inhibited proIL-1beta protein expression. Furthermore, a dose of 60 microg/mL of essential oil was effectively inhibitory for IL-1beta and IL-6 production but not for TNF-alpha, suggesting that essential oil was bioactive in antiinflammation in vitro. This study is the first to report antiinflammatory activity of extracts obtained from the leaf essential oil of C. osmophloeum.     

Vermicompost from biodegraded distillation waste improves soil properties and essential oil yield of Pogostemon cablin (patchouli) Benth

Pre-treatment of patchouli lignocellullosic distillation waste with a consortium of microbes viz. Trichoderma harzianum – ATCC PTA-3701, Pseudomonas monteilii – HQ995498, Bacillus megaterium – ATCC 14581 and Azotobacter chroococcum – MTCC 446 significantly enhanced the bio-degradation of cellulose, hemicelluloses and lignin by 58.44%, 29.44% and 65.23%, respectively and improved the yield of vermicompost by 15%. Application of bioinoculant-enriched vermicompost (BEVC) in patchouli reduced the percent disease index (PDI) of Rhizoctonia root-rot by 36.36% and improved the essential oil yields by 59.74%, 37.70% and 37.96 as compared to plots receiving untreated (not enriched) vermicompost (VC), bioinoculant-enriched compost (BEC) and chemical fertilizers (CF), respectively. Furthermore, BEVC application resulted in a marked improvement in physical (bulk density and water holding capacity) and chemical properties (pH, percent organic carbon, available N, P and K) of the soil. In conclusion, BEVC from distillation waste can be safely utilized as a bio-organic input unambiguously particularly in situations where the use of chemical fertilizers and pesticides is restricted like organic agriculture.     

Antioxidative properties of tripeptide libraries prepared by the combinatorial chemistry

Two series of combinatorial tripeptide libraries were constructed, based on an antioxidative peptide isolated from a soybean protein hydrolysate. One was a library of 108 peptides containing either His or Tyr residues. Another was a library of 114 peptides related to Pro-His-His, which had been identified as an active core of the antioxidative peptide. The antioxidative properties of these libraries were examined by several methods, such as the antioxidative activity against the peroxidation of linoleic acid, the reducing activity, the radical scavenging activity, and the peroxynitrite scavenging activity. Two Tyr-containg tripeptides showed higher activities than those of two His-containing tripeptides in the peroxidation of linoleic acid. Tyr-His-Tyr showed a strong synergistic effects with phenolic antioxidants. However, the tripeptide had only marginal reducing activity and a moderate peroxynitrite scavenging activity. Cysteine-containing tripeptides showed the strong peroxynitrite scavenging activity. Change of either the N-terminus or C-terminus of Pro-His-His to other amino acid residues did not significantly alter their antioxidative activity. Tripeptides containing Trp or Tyr residues at the C-terminus had strong radical scavenging activities, but very weak peroxynitrite scavenging activity. The present results allow us to understand why protein digests have such a variety of antioxidative properties.     

Antioxidative and antimutagenic activities of 4-vinyl-2,6-dimethoxyphenol (canolol) isolated from canola oil

A potent antioxidative compound in crude canola oil, canolol, was recently identified, and reported herein are studies of its scavenging capacity against the endogenous mutagen peroxynitrite (ONOO(-)). ONOO(-) is generated by the reaction between superoxide anion radical and nitric oxide, both of which are produced by inflammatory leukocytes. Among various antioxidative substances of natural or synthetic origin, canolol was one of the most potent antimutagenic compounds when Salmonella typhimurium TA102 was used in the modified Ames test. Its potency was higher than that of flavonoids (e.g., rutin) and alpha-tocopherol and was equivalent to that of ebselen. Canolol suppressed ONOO(-)-induced bactericidal action. It also reduced intracellular oxidative stress and apoptosis in human cancer SW480 cells when used at a concentration below 20 microM under H(2)O(2)-induced oxidative stress. In addition, canolol suppressed plasmid DNA (pUC19) strand breakage induced by ONOO(-), as revealed by agarose gel electrophoresis.     

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.     

Biological activity and chemical composition of the essential oil from Jamaican Hyptis verticillata Jacq

The chemical composition of the essential oil obtained by hydrodistillation from the aerial parts of Hyptis verticillata Jacq. was elucidated by a combination of GC and GC-MS analyses. The oil was dominated by the sesquiterpenoids cadina-4,10(15)-dien-3-one (15.1%) (1) and aromadendr-1(10)-en-9-one (squamulosone) (30.7%) (2). The oil exhibited chemosterilant activities against the cattle tick, Boophilus microplus Canest., and toxic action against adult Cylas formicarius elegantulus Summer, the most destructive pest of sweet potato (Ipomoea species).     

Antioxidative compounds from the outer scales of onion

Antioxidative compounds were isolated from the methanol extract of dry outer scales of onion (Allium cepa L.). Nine phenolic compounds (1-9) were finally obtained by reversed-phase high-performance liquid chromatography, and their structures were elucidated by NMR and mass spectrometry analyses. They were the six known compounds, protocatechuic acid (1), 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (2), quercetin 4'-O-beta-D-glucopyranoside (3), quercetin (5), 4'-O-beta-d-glucopyranoside of quercetin dimer (7), and quercetin dimer (8), and three novel compounds, condensation products of quercetin with protocatechuic acid (4), adduct of quercetin with quercetin 4'-O-beta-D-glucopyranoside (6), and quercetin trimer (9). These phenolic compounds were tested for their antioxidant properties using autoxidation of methyl linoleate in bulk phase or free radical initiated peroxidation of soybean phosphatidylcholine in liposomes. The flavonoid compounds having o-dihydroxy substituent in the B-ring were shown to be effective antioxidants against nonenzymic lipid peroxidation.     

Coriander essential oil composition from two genotypes grown in different environmental conditions

The objective was to study the essential oil composition of coriander fruits in plants growing in environments differing in soil conditions and weediness level. Factorial field experiments were conducted in two locations from the Rolling Pampas, Argentina, and two coriander landraces (European and Argentinean) were tested under two levels of nitrogen fertilization and weediness. Data were evaluated with uni- and multivariate techniques. The variation in the oil composition was related to the relative proportion of the constituents and not to the presence/absence of a particular component. Weather conditions in 1997 favored linalool and camphor in both landraces. Location, fertilization, and weediness also affected the chemical profile. The European landrace showed a more stable concentration of the major components than the Argentinean landrace. These results, which show the relationships between some environmental conditions and the essential oil composition, are useful in the development of innovative strategies aimed to improve oil composition and to manage crop pests.     

Composition of the essential oil of Mentha microphylla from the Gennargentu Mountains (Sardinia,Italy)

The essential oil obtained by hydrodistillation of the fresh aerial parts of Mentha microphylla C. Kock (Lamiaceae) collected on the Gennargentu Mountains (Sardinia, Italy) has been investigated by gas chromatography (GC) and GC/mass spectrometry (MS). The main constituents that resulted were pulegone (34.1%), piperitenone oxide (32.9%), and piperitenone (11.3%). The presence of small amounts of compounds such as ethyl hexanoate, 1-octen-3-ol, nonanal, and ethyl 2-methylbutanoate could justify the particular odorous profile of the plant, resembling the aroma of milk and other dairy products such as mozzarella.     

Composition and antifungal activity on soil-borne pathogens of the essential oil of Salvia sclarea from Greece

The hydrodistilled essential oils of the aerial parts of wild-growing Salvia sclarea originated from two localities in Greece were analyzed by GC-MS. Sixty-six compounds, representing 93.26-98.19% of the oils, were identified. Linalyl acetate (19.75-31.05%), linalool (18.46-30.43%), geranyl acetate (4.45-12.1%), and alpha-terpineol (5.08-7.56%) were the main components. The antifungal activity of the oil of one locality and of the main components, linalyl acetate and linalool, was evaluated in vitro against three soil-borne pathogens.     

Linalool from Lippia alba: study of the reproducibility of the essential oil profile and the enantiomeric purity

A new chemotype of the aromatic Verbenaceae species Lippia alba Mill. N. E. Br. from southeastern Brazil has recently been shown to have a high content of linalool in the leaf essential oil. Vegetative propagation of this chemotype was conducted at six different locations in Brazil, and the variation of the content and the optical purity of linalool in the oils were verified. Yields (0.6-0.9%, hydrodistillation), chemical composition, linalool content, and optical purity of the oils from all the plants were compared, using GC-FID, GC-MS, chiral chromatography, and retention index calculation. No plant exceeded the matrix in linalool content (46.5 to 90.7%), and the chemical profile of the oils was the same for all the samples. Purification of linalool to a content close to 100% was effected by vacuum distillation of the crude oil. Chiral analysis showed exclusively the presence of S-linalool in all the crude oils and in the distilled samples.     

短程分子蒸馏技术精制巨尾桉叶精油工艺优化

为了优化巨尾桉叶精油精制工艺,采用短程分子蒸馏,对初级桉叶精油中1,8-桉叶素和α-蒎烯进行精制,研究不同温度和压力条件下2种物质分离特性。以巨尾桉叶为试验材料,依次采用超临界CO2萃取和分子蒸馏对其进行桉叶油树脂提取和纯化得到初级桉叶精油,采用二因素五水平的响应面优化试验,将馏出物得率、馏出物中1,8-桉叶油素质量分数及α-蒎烯质量分数、馏余物中1,8-桉叶油素质量分数及α-蒎烯质量分数作为试验指标,对分子蒸馏精制桉叶精油工艺进行优化研究。最优纯化工艺条件:以馏出物为目标产物,蒸馏温度38℃,蒸馏压力41 Pa,馏出物中1,8-桉叶油素和α-蒎烯的质量分数分别约为60.80%和31.58%,馏出物的得率为82.06%。分子蒸馏能够对桉叶精油进行有效的纯化精制,桉叶初级精油经过二级分子蒸馏精制后,1,8-桉叶油素和α-蒎烯的质量分数分别提高了77.62%和56.72%。蒸馏温度和蒸馏压力对1,8-桉叶油素质量分数的影响均较α-蒎烯明显,同时,对于1,8-桉叶油素,蒸馏压力的变化对其质量分数的影响较蒸馏温度明显,相反的,对于α-蒎烯,蒸馏温度对其质量分数影响更为显著(P0.05),该研究结果可为分离提纯2种物质提供技术参考。     

Composition and antibacterial activity of Pseudocytisus integrifolius (Salisb.) essential oil from Algeria

The essential oil composition of an endemic Algerian Cruciferae, Pseudocytisus integrifolius (Salisb.) Rehder, was analyzed by gas chromatography (GC) and GC-mass spectrometry (MS). Eighty-three components representing more than 96.5% of the oil were identified. The major components were dimethyl disulfide (33.4%), dimethyl trisulfide (24.2%), and an unsaturated nitrile (31.7%). Fractionation on a silica gel column led to the identification of trace-level compounds, in particular, polar compounds such as nitriles and aldehydes, and to the isolation of dimethyl disulfide, dimethyl trisulfide, and an unsaturated nitrile. Structural analysis using high-resolution mass spectrometry (HRMS) and 1H,13C NMR techniques enabled the identification of pent-4-enenitrile. Variation in essential oil composition and yields was studied according to harvesting time, drying, and parts of the plant. The essential oil of aerial parts was tested for its antibacterial activity using a paper disk method. The oil was effective on the inactivation of Escherichia coli and Pseudomonas aeruginosa and ineffective on the inactivation of Staphylococcus aureus.     

Model study of the enzymatic modification of natural extracts: peroxidase-based removal of eugenol from rose essential oil

A protocol based on the use of horseradish peroxidase (HRP) is proposed for the removal of allergenic eugenol from rose essential oil without loss of the organoleptic quality and with a good conservation of the chemical composition. For the first time, an enzyme-based strategy is proposed for essential oils treatment and opens new opportunities in the detoxification of natural extracts used in perfumery and cosmetics. Our results on eugenol in rose essential oil constitute a first step toward the development of efficient and mild processes for the removal of more toxic compounds of natural extracts.