Polyphenolic profile and antioxidant effects of various parts of Artemisia annua L.

An annual Korean weed, Artemisia annua L., has been used as a folk medicine for the treatment of a number of diseases. Remarkably, among the 32 polyphenols characterized in various parts of plant tissue, including flowers, leafs, stems and roots, 10 compounds were detected for the first time using liquid chromatography–tandem mass spectrometry (LC/MS/MS). The quantification method was validated using structurally related external standards with determination coefficients (R²) ≥0.9995. The limits of detection and quantitation were 0.068–3.932 and 0.226–13.108 mg/L, respectively. The recoveries estimated at 50 and 100 mg/L ranged between 60.6–92.2 and 61.3–111%, respectively, with relative standard deviations <12%. The roots contained the largest concentration of identified components, while the flowers contained the least. The antioxidant capacity evaluated in terms of 1,1‐diphenyl‐2‐picrylhydrazyl and 2,2′‐azinobis(3‐ethylbenzothiazoline‐6‐sulfonic acid) radical cation‐scavenging activities and reducing power was highest in the roots and lowest in the flowers. The findings are well correlated and suggest that the antioxidant capacities principally depend upon the polyphenol concentrations in each part of the plant. Copyright © 2015 John Wiley & Sons, Ltd.     

Determination of dihydroartemisinic acid in Artemisia annua L. by gas chromatography with flame ionization detection

Dihydroartemisinic acid (DHAA) is the direct precursor to artemisinin, an effective anti‐malaria compound from Artemisia annua L. (A. annua ), and it can be transformed to artemisinin without the catalysis of enzyme. A rapid and sensitive analysis of DHAA in A. annua is needed to screen excellent plant resources aimed to improve artemisinin production. In order to develop a rapid and sensitive determination method for DHAA in plant, the extraction and analysis conditions were extensively investigated in the present work. As a result, extraction of powdered A. annua leaves at 55°C for 50 min with chloroform resulted in the highest yield of DHAA, with a recovery of >98%. The precision of this gas chromatographic procedure ranged from 1.22 to 2.94% for intra‐day and from 1.69 to 4.31% for inter‐day, respectively. The accuracy was 99.55–103.02% for intra‐day and 98.86–99.98% for inter‐day, respectively. The measured LOQ and LOD values of the proposed method reached 5.00 and 2.00 μg/mL, respectively. Validation indicated the method was robust, quick, sensitive and adequate for DHAA analysis.     

Development and validation of a simple thin layer chromatographic method for the analysis of artemisinin in Artemisia annua L. plant extracts

Owing to the development of parasite resistance to standard antimalarial treatments like chloroquine and sulfadoxine-pyrimethamine, the demand for Artemisia annua, a key ingredient for new and highly effective antimalarial drugs, is huge. Therefore selective and precise methods to determine the content of artemisinin in dry plant material and in raw impure extracts are needed. In this work a method is described for the clear separation and extraction of artemisinin from other plant components in the Artemisia annua L. plant by thin-layer chromatography (TLC). To obtain optimal extraction and recovery efficiency, several parameters were evaluated, including choice of extraction solvent, TLC plate type and sensitivity between UV and visible light. Method validation was performed on both the dry plant material and non-purified plant extracts. Toluene presented the highest extraction efficiency compared with petroleum ether, hexane and methanol. Reversed-phase plates showed more concentrated spots than normal-phase plates, while the sensitivity of the analysis in UV was comparable to that in visible light but less precise. The impure plant extracts were analyzed by both TLC and HPLC-UV at 215 nm and both methods met the requirements for linearity, selectivity, precision and accuracy. Hence, the proposed TLC method can easily be used for both qualitative and quantitative control of the raw plant extract in areas where advanced methods are scarce.     

Simultaneous isolation of artemisinin and its precursors from Artemisia annua L. by preparative RP-HPLC

It is still a major challenge to simultaneously isolate artemisinin and its precursors, especially dihydroartemisinic acid and artemisinic acid, from herbal Artemisia annua. A rapid, economical and automatical chromatographic separation process to isolate and purify artemisinin, dihydroartemisinic acid and artemisinic acid at the same time on a preparative scale was developed. The procedure included solvent extraction of ground Artemisia annua leaves by refluxing and purification of crude extract by preparative reverse-phase high-performance liquid chromatography (RP-HPLC). Fractions containing artemisinin and its precursors were collected and identified by gas chromatography and mass spectrometry. High purity of artemisinin, dihydroartemisinic acid and artemisinic acid was obtained by preparative HPLC with a C(18) column and 60% acetonitrile in water as the mobile phase. The techniques described here are useful tools for the preparative-scale isolation of artemisinin and its precursors in a fast, cost-effective and environmental friendly manner.     

Structural Characterization and In-Vitro Antioxidant and Immunomodulatory Activities of Polysaccharide Fractions Isolated from Artemisia annua L.

Arimisia annua L. is an important anticancer herb used in traditional Chinese medicine. The molecular basis underpinning the anticancer activity is complex and not fully understood, but the herbal polysaccharides, broadly recognised as having immunomodulatory, antioxidant and anticancer activities, are potential key active agents. To examine the functions of polysaccharides from A. annua, their immunomodulatory and antioxidant potentials were evaluated, as well as their structural characterization. The water-soluble polysaccharides (AAPs) were fractionated using size-exclusion chromatography to obtain three dominant fractions, AAP-1, AAP-2 and AAP-3, having molecular masses centered around 1684, 455 and 5.8kDa, respectively. The antioxidant potentials of the isolated polysaccharides were evaluated by measuring radical scavenging activities against DPPH^● (2,2-diphenyl-1-picrylhydrazyl radical), ABTS^●+ (2,2′-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid radical ion), and the OH^● (hydroxyl radical). AAP-1 displayed high antioxidant activities against these radicals, which were 68%, 73% and 78%, respectively. AAP-2 displayed lower scavenging activities than the other two fractions. Immunostimulatory activities of AAPs were measured using mouse macrophages. The three polysaccharide fractions displayed significant antioxidant activities and stimulated the production of tumor necrosis factor-α (TNF-α) and interleukin-6 (IL-6). AAP-1 showed significant immunostimulatory activity (16-fold increase in the production of IL-6 compared to the control and 13-fold increase in the production of TNF-α) with low toxicity (>60% cell viability at 125 μg/mL concentration). Preliminary structural characterization of the AAPs was carried out using gas chromatography (GC) and FTIR techniques. The results indicate that AAP-1 and AAP-2 are pyranose-containing polysaccharides with β-linkages, and AAP-3 is a β-fructofuranoside. The results suggest that these polysaccharides are potential candidates for immunotherapy and cancer treatment.     

孜然精油的提取及其清除DPPH自由基能力研究

在光、热以及氧气存在下,物质化学键断裂,生成高反应活性的自由基或者过氧化物,导致食品变质,商品变性,质量下降。为了保证食品质量与安全,保证产品不变质,添加抗氧化剂是常用的方法。随着人们环保意识的提高,越来越倾向于用天然抗氧化剂取代合成抗氧化剂。当使用天然抗氧化剂,     

Affordable and rapid HPTLC method for the simultaneous analysis of artemisinin and its metabolite artemisinic acid in Artemisia annua L.

Artemisinin (AN) and artemisinic acid (AA), valuable phyto‐pharmaceutical molecules, are well known anti‐malarials, but their activities against diseases like cancer, schistosomiasis, HIV, hepatitis‐B and leishmaniasis are also being reported. For the simultaneous estimation of AN and AA in the callus and leaf extracts of A. annua L. plants, we embarked upon a simple, rapid, selective, reliable and fairly economical high performance thin layer chromatography (HPTLC) method. Experimental conditions such as band size, chamber saturation time, migration of solvent front and slit width were critically studied and the optimum conditions were selected. The separations were achieved using toluene–ethyl acetate, 9:1 (v/v) as mobile phase on pre‐coated silica gel plates, G 60F₂₅₄. Good resolution was achieved with R_f values of 0.35 ± 0.02 and 0.26 ± 0.02 at 536 nm for AN and 626 nm for AA, respectively, in absorption–reflectance mode. The method displayed a linear relationship with r² value 0.992 and 0.994 for AN and AA, respectively, in the concentration range of 300–1500 ng for AN and 200–1000 ng for AA. The method was validated for specificity by obtaining in‐situ UV overlay spectra and sensitivity by estimating limit of detection (30 ng for AN and 15 ng for AA) and limit of quantitation (80 ng for AN and 45 ng for AA) values. The accuracy was checked by the recovery studies conducted at three different levels with the known concentrations and the average percentage recovery was 101.99% for AN and 103.84% for AA. The precision was analyzed by interday and intraday precision and was 1.09 and 1.00% RSD for AN and 1.22 and 6.05% RSD for AA. The analysis of statistical data substantiates that this HPTLC method can be used for the simultaneous estimation of AN and AA in biological samples. Copyright © 2015 John Wiley & Sons, Ltd.     

Phenolic profile,antioxidant capacity and anti-inflammatory activity of Anethum graveolens L. essential oil

This study reports the chemical composition, antioxidant and anti-inflammatory properties of Anethum graveolens essential oil and its main compounds. The essential oil was obtained from the aerial parts of the plant by hydrodistillation and analysed by using GC/MS. α-Phellandrene (19.12%), limonene (26.34%), dill ether (15.23%), sabinene (11.34%), α-pinene (2%), n-tetracosane (1.54%), neophytadiene (1.43%), n-docosane (1.04), n-tricosane (1%), n-nonadecane (1%), n-eicosane (0.78%), n-heneicosane (0.67%), β-myrcene (0.23%) and α-tujene (0.21%) were found to be the major constituents of the oil. A. graveolens oil exhibit a higher activity in each antioxidant system with a special attention for β-carotene bleaching test (IC₅₀: 15.3 μg/mL) and reducing power (EC₅₀: 11.24 μg/mL). The TLC-bioautography screening and fractionation resulted in the separation of the main antioxidant compounds, which were identified as limonene (45%) and sabinene (32%). The essential oil and its main compounds exhibited a potent NO-scavenging effect and inhibited the expression of inducible NO synthase.     

新疆一枝蒿挥发油化学成份的研究

新疆一枝蒿挥发油有明显的抗过敏作用。通过 GC/MS/DS 分析,表明有三十九种化学成份,并确证了其中十八种的结构及含量。     

Chemical Composition,Enantiomeric Distribution,Antimicrobial and Antioxidant Activities of Origanum majorana L. Essential Oil from Nepal

This study was conducted to examine the chemical constituents of Origanum majorana L. essential oils (EOs) that originate in Nepal, as well as their biological activities, antioxidant properties, and enantiomeric compositions. The EOs were extracted by the hydro-distillation method using a Clevenger-type apparatus and their chemical compositions were determined through gas chromatography and mass spectrometry (GC-MS). Chiral GC-MS was used to evaluate the enantiomeric compositions of EOs. The minimum inhibitory concentrations (MICs) of the essential oils were determined by the micro-broth dilution method, and the antioxidant activity was evaluated by the 2,2-diphenyl-1-picrylhydrazyl scavenging assay and ferric-reducing antioxidant power (FRAP). GC-MS analysis showed the presence of 50 and 41 compounds in the EO samples, (S₁) and (S₂), respectively, representing the Kathmandu and Bhaktapur districts. The oxygenated monoterpenoids, along with terpinen-4-ol, were predominant constituents in both EO samples. However, the EOs from two locations showed some variations in their major components. The chiral terpenoids for two EO samples of marjoram have also been reported in this study in an elaborative way for the first time in accordance with the literature review. A hierarchical cluster analysis based on the compositions of EOs with 50 compositions reported in the literature revealed at least 5 different chemotypes of marjoram oil. The antioxidant activity for the sample (S₂) was found to be relatively moderate, with an IC₅₀ value of 225.61 ± 0.05 μg/mL and an EC₅₀ value of 372.72 ± 0.84 µg/mL, as compared to the standard used. Furthermore, with an MIC value of 78.1 µg/mL, the EO from sample (S₂) demonstrated effective antifungal activity against Aspergillus niger and Candida albicans. Moreover, both samples displayed considerable antimicrobial activity. The results suggest that EOs of Origanum majorana possess some noteworthy antimicrobial properties as well as antioxidant activity, and hence can be used as a natural preservative ingredient in the food and pharmaceutical industries.     

Determination of non-toxic and potentially toxic elements concentration and antioxidant capacity in selected natural and essential oils with high market values

Natural oils (NOs) and essential oils (EOs) are widely used in the food and beverage, medical, aromatherapy and cosmetic industries, but little is known about their elemental composition or antioxidant ability. Microwave-assisted acid digestion and inductively coupled plasma-optical emission spectroscopy were used to determine the non-toxic elements (Al, Ca, Cu, Fe, K, Mg, Na, Se and Zn) and potentially toxic elements (As, Cr, Cd, Mn, Ni and Pb) concentrations in 13 selected NOs and EOs. The per cent recoveries of laboratory-fortified blanks analysed for quality control were 94–110%. The elemental concentrations varied widely in NO and EO samples, as demonstrated by the large standard deviation obtained for some elements. The average levels of non-toxic elements (Al (14.5 ± 3.7 μg/g); Ca (278 ± 138 μg/g); Cu (7 ± 14 μg/g); Fe (16 ± 5 μg/g); K (36 ± 31 μg/g); Mg (56 ± 27 μg/g); Na (266 ± 277 μg/g); Se (0.7 ± 0.3 μg/g) and Zn (6.1 ± 2.6 μg/g)) were determined in NOs and EOs. Comparatively, low levels of potentially toxic elements (As (0.1 ± 0.2 μg/g); Cd (0.1 ± 0.0 μg/g); Cr (0.2 ± 0.1 μg/g); Mn (0.8 ± 0.1 μg/g); Ni (4.5 ± 2.2 μg/g); and Pb (0.3 ± 0.2 μg/g)) were obtained in the oils. Principal component analysis (PCA) revealed that the first two principal components explained 100% of the variability in the elemental concentrations. Na, Ca, Mg and K were the main contributors to PCA. Non-toxic element pairs were strongly correlated (R² > 0.9440) indicating a common source in these oils, but toxic element pairs were poorly correlated. Although toxic element concentrations were low, routine monitoring in oils is recommended. The antioxidant ability of NOs and EOs to potentially reduce free radicals, which are often involved in several degenerative diseases, such as ageing, stroke, diabetes and cancers was determined by DPPH (2,2-di(4-tert-octylphenyl)-1-picrylhydrazyl) free radical scavenging assay and ultraviolet-visible spectroscopy. Jasmine, castor and tea tree lemon oils were the best antioxidants. The oils in this study have the potential to replace artificial antioxidants used in foods, cosmetics and other products.     

Chemical Composition and Antioxidant and Antibacterial Potencies of the Artemisia ordosica Aerial Parts Essential Oil during the Vegetative Period

As one of the vital shrubs growing in crusted areas in China, Artemisia ordosica (belonging to the Asteraceae family) is abundant in essential oil, and its aerial part’s essential oil has been reported to have some biological activities during the flowering and fruit set stage, and has been used in folk medicine. However, little is known about the biological activities of its aerial part’s essential oil during the vegetative period. Thus, the purpose of this work was to determine the chemical composition and evaluate the antioxidant and antibacterial potencies of the essential oil extracted from A. ordosica aerial parts during the vegetative stage. Gas chromatography coupled with mass spectrometry (GC-MS) revealed that spathulenol (9.93%) and α-curcumene (9.24%), both sesquiterpenes, were the most abundant of the 74 chemical constituents detected in the essential oil of A. ordosica. The antioxidant activity of the essential oil was found to be relatively moderate against 2,2-diphenylhydrazyl (DPPH), 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS), and hydroxyl radical (OH^●) radicals. The essential oil exhibited strong antibacterial activity against Staphylococcus aureus, Salmonella abony and Escherichia coli, with minimum inhibitory concentrations (MICs) of 2.5, 5, and 10 μL/mL, respectively. The results indicate that the essential oil of A. ordosica possesses notable antibacterial properties as well as antioxidant capability and can thus be employed as a natural ingredient which can be used as a substitute for antibiotics in the animal feed industry. However, in vivo toxicological studies are still required to determine the safety level and beneficial outcomes of the A. ordosica essential oil for future utilization.     

Fumigant and repellent activities of essential oil extracted from Artemisia dubia and its main compounds against two stored product pests

The major chemical constituents of the essential oil extracted from Artemisia dubia wall. ex Bess. (Family: Asteraceae) were found as terpinolene (19.02%), limonene (17.40%), 2,5-etheno[4.2.2]propella-3,7,9-triene (11.29%), isoelemicin (11.05%) and p-cymene-8-ol (5.93%). Terpinolene and limonene were separated as main components from the essential oil. The essential oil showed fumigant toxicity against Tribolium castaneum and Liposcelis bostrychophila with LC₅₀ values of 49.54 and 0.74 mg/L, respectively. The essential oil and isolated compounds of A. dubia showed repellency activities against both insects. Terpinolene and limonene showed the fumigant toxicity against T. castaneum. Terpinolene showed obvious fumigant toxicity against L. bostrychophila. The results indicated that the essential oil of A. dubia had potential to be developed into natural insecticides for controlling stored product pests.     

Volatiles composition and antioxidant activity Inula oculus-christi L. from Serbia

Abstract

The chemical composition of the essential oil and the volatiles obtained by static headspace (HS) of Inula oculus-christi L. is presented. The GC-MS analysis of the hydrodistilled oil resulted in the identification of 90 components, representing 92.7% of the oil. The most abundant compounds were: caryophyllene oxide (9.8%), trans-longipinocarveol (9.2%), eucalyptol (7.3%) and intermedeol (6.2%). The major constituent of I. oculus-christi L. HS volatiles was eucalyptol (87.4%). The antioxidant activity was evaluated by four different methods: 2,2-diphenyl-1-picryl-hydrazylhydrate free radical assay (DPPH), 2,2-azino-bis-3-ethylbenzothiazoline-6-sulfonic acid (ABTS) method, total reducing power (TRP), ferric reducing antioxidant power (FRAP), and cupric reducing antioxidant capacity (CUPRAC). Total phenolic content in (TPC) examined oil was 177.95?µg GAE/mg oil. Radical scavenging potential of the oil was promising RSC-DPPH was 57.4% and RSC-ABTS was 82.7%.

     

Identification and Biological Activity of Volatile Organic Compounds Emitted by Plants and Insects. IV. Composition of Vapor Isolated from Certain Species of Artemisia Plants

The components of fragrance from four wormwood species of theArtemisiaL. genus were analyzed by GC-MS. The major and minor components of volatile essential oils typical of the studied plant species were determined.     

Chemical composition and antimicrobial activity of the essential oils of Artemisia absinthium,Artemisia scoparia,and Artemisia sieberi grown in Saudi Arabia

Essential oils (EOs) are one of the most significant products of plant metabolites, the current research work was performed to determine and compare the chemical compositions of the EOs extracted from three different species of Artemisia (absinthium, sieberi, and scoparia) growing in Saudi Arabia and to test their antimicrobial potential against different bacterial and fungal strains. The EOs were isolated by hydro-distillation and analyzed by combining a gas chromatography–flame ionization detector (GC–FID) with the gas chromatography–mass spectroscopy (GC–MS) technique. Chemical analysis revealed that the three species had four compounds in common, i.e., limonene, camphor, terpinen-4-ol, and ethyl 2-methylbutyrate, while the main components identified in the EOs of A. absinthium and A. sieberi were cis-davanone (34.7% and 36.1%, respectively) and camphor (16.2% and 24.1%, respectively). In contrast, the keto compounds dominated in the oil of A. scoparia with 2-nonanone (55%) and 2-undecanone (24.5%) representing more than 80% of the total oil content. In addition, the antimicrobial activity of the isolated oils was evaluated by the broth microdilution method, revealing that all the EOs isolated from the examined Artemisia species displayed growth inhibiting actions in a concentration-dependent manner on selected tested microorganism species. The findings of the study also suggested that the tested EOs could be used to develop effective natural antimicrobial remedies with potential application in the fields of cosmetic industry, food manufacturing and medicine.     

Analysis of essential oils from Voacanga africana seeds at different hydrodistillation extraction stages: chemical composition,antioxidant activity and antimicrobial activity

In this study, essential oils from Voacanga africana seeds at different extraction stages were investigated. In the chemical composition analysis, 27 compounds representing 86.69–95.03% of the total essential oils were identified and quantified. The main constituents in essential oils were terpenoids, alcohols and fatty acids accounting for 15.03–24.36%, 21.57–34.43% and 33.06–57.37%, respectively. Moreover, the analysis also revealed that essential oils from different extraction stages possessed different chemical compositions. In the antioxidant evaluation, all analysed oils showed similar antioxidant behaviours, and the concentrations of essential oils providing 50% inhibition of DPPH-scavenging activity (IC₅₀) were about 25 mg/mL. In the antimicrobial experiments, essential oils from different extraction stages exhibited different antimicrobial activities. The antimicrobial activity of oils was affected by extraction stages. By controlling extraction stages, it is promising to obtain essential oils with desired antimicrobial activities.     

Rapid identification and global characterization of multiple constituents from the essential oil of Cortex Dictamni based on GC–MS

The root of Dictamnus dasycarpus Turcz ., also known as Cortex Dictamni, is a Chinese herbal medicine that has been commonly used in the treatment of inflammation, microbial infection, cancer, and other diseases in China for thousands of years. Recently, the essential oil of Cortex Dictamni has been widely studied, and a large number of volatile constituents have been discovered. However, the research of the essential oil of Cortex Dictamni in vivo remains unknown, especially the constituents absorbed into blood after oral administration. Hence, a sensitive and rapid method using gas chromatography with mass spectrometry combined with MassHunter software and the National Institute of Standards and Technology 2014 database was used to investigate the absorbed components in rat serum after oral administration of the essential oil of Cortex Dictamni. With the established method, a total of 36 compounds were screened and identified in the essential oil of Cortex Dictamni based on the mass spectrometry data and compound database. Among them, eight compounds, elemol, thymol methyl ether, β‐eudesmol, β‐cyclocostunolid, guaiazulene, trans‐4‐hydroxystilbene, ethyl oleate, and monoelaidin, were tentatively characterized in rat serum. This work demonstrated that the established method proved to be a powerful technique for rapid, simple, reliable, and automated identification of bioactive components of herbal medicine.     

Composition of essential oil from <Emphasis Type="Italic">Artemisia glauca</Emphasis> from western Siberia

The composition of essential oil from Artemisia glauca (Asteraceae) growing in southern Siberia was studied. More than 60 oil components consisting of 99.0–99.7% of the total volatile components were identified by GC—MS by comparison of full mass spectra and retention times. The main components of the essential oil were acetylene derivatives of capillene (11–60%) and benzyldiacetylene (1–31%). Other acetylene derivatives such as capillin, (E)-hex-4-en-2-ynylbenzene, 1-(4-methoxyphenyl)-2,4-pentadiyne, and capillarin were also identified in the oil. __________ Translated from Khimiya Prirodnykh Soedinenii, No. 5, pp. 446–449, September–October, 2007.     

Quality Assessment of Artemisia rupestris L. Using Quantitative Analysis of Multi-Components by Single Marker and Fingerprint Analysis

The chromatographic fingerprint of 14 batches of Artemisia rupestris L. samples were established in this study. The constituents of ten components in Artemisia rupestris L. were determined using quantitative analysis of multi-components by single marker (QAMS) and the external standard method (ESM). Due to their stability and accessibility, chlorogenic acid and linarin were used as references to calculate the relative correction factors (RCFs) of apigenin-C-6,8-pentoside-hexoside, apigenin-C-6,8-di-pentoside, luteolin, 3,4-dicaffeoylquinic acid, 3,5-dicaffeoylquinic acid, 4,5-dicaffeoylquinic acid, chrysosplenetin B, and sbsinthin, based on high-performance liquid chromatography (HPLC). The value calculated by QAMS was consistent with that of the ESM, and the reproducibility of RCFs was found to be reliable. In conclusion, simultaneous determination of the ten components by the QAMS method and chromatographic fingerprint analysis were feasible and accurate in evaluating the quality of Artemisia rupestris L. and can be used as reference in traditional Chinese medicine quality control.