Composition and antioxidant activity of the essential oil of Artemisia annua L

Abstract

Artemisia annua L. is an annual Eurasian desert-steppe plant. The composition of essential oils found in Artemisia annua from Russian (Buryatian) flora was analyzed in this work using gas chromatography mass-spectrometry method. Artemisia ketone, β-selinene, caryophyllene, caryophyllene oxide, germacrene D were the main components of the analyzed essential oils. The comparison of own and literature data showed that the essential oils of A. annua conditionally could be divided into “Asian” and “European” groups. Our samples, referring to “Asian” profile, exhibited higher antiradical activity in comparison with data from previously published studies.     

Two New Phenolic Compounds from Artemisia iwayomogi

Two new phenolic compounds, (Z)‐5′‐hydroxyjasmone 5′‐O‐{6″‐O‐[(E)‐caffeoyl]‐β‐D ‐glucopyranoside} ( 1 ) and quercetin‐7‐O‐β‐D ‐glucuronide methyl ester ( 2 ), along with ten known phenolic compounds, 3 – 12 , were isolated from the aerial parts of Artemisia iwayomogi. Their structures were elucidated by spectroscopic methods, including 1D‐ and 2D‐NMR, and HR‐ESI‐TOF‐MS techniques. The inhibitory effects of compounds 1 – 12 on the LPS‐stimulated production of IL‐12 p40, IL‐6, and TNF‐α in bone marrow‐derived dendritic cells were evaluated.     

Quantitative fingerprint and antioxidative properties of Artemisia argyi leaves combined with chemometrics

Quantitative fingerprint and differences of Artemisia argyi from different varieties, picking time, aging year, and origins were analyzed combing with chemometrics. The antioxidant activity was determined and antioxidant markers of Artemisia argyi were screened. Variety WA3 was significantly different from that of the other varieties. Fingerprint peak response and antioxidant activity of A. argyi picked in December were lower than samples collected in May and August. Fresh A. argyi leaves were significantly superior to withered leaves and stems. Artemisia argyi aging 1–5 years presented a classification trend. Antioxidant activity of A. argyi produced in Nanyang was generally superior to others origins. Peak 9, isochlorogenic acid A, and 6-methoxyluteolin contributed greatly for classification of A. argyi from different variety, picking time, aging year, and origin. Isochlorogenic acid A, isochlorogenic acid C, 6-methoxyluteolin, and chlorogenic acid were selected as antioxidant marker of A. argyi. The method based on quantitative fingerprint, antioxidant activity evaluation, and chemometrics was reliable to analyze the differences of A. argyi samples from different sources.     

Total phenolic content,ferric reducing and DPPH scavenging activity of Arum dioscoridis

Arum dioscoridis, locally called ‘Gavur pancari’, is a wild plant the leaves of which have been used as vegetable and for preparing special soup which has a sour taste. This study was set up to determine in vitro antioxidant activities and total phenolic and flavonoid contents of different extracts of A. dioscoridis. Free radical scavenging activity was evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and ferric reducing activity with different concentrations of ethanol, methanol, acetone and water extracts of the plant leaves. Total phenolic and flavonoid contents were widely variable depending on solvents. Ethanol and methanol extractions of the plant material showed better performances with respect to both phenolic and flavonoid contents, respectively. The highest phenolic and flavonoid contents of ethanol and methanol extracts were 100.890 mg/g GAE and 72.643 mg/g QE, respectively. The lower DPPH scavenging and ferric reducing activities were determined in comparison with previous reports and standard synthetic chemicals.     

Comparative study on Artemisia halodendron Turcz. and its two related plants by GC-MS analysis and protective effect against carbon tetrachloride-induced hepatotoxicity in mice

A rapid method had been used for comparative study on Artemisia halodendron Turcz. and its two related plants by gas phase-mass spectrometry (GC-MS). The comparison of the volatile oils obtained in three plants by GC-MS were similar in 20 compositions. However, n-Hexadecanoic acid (10.40%), Biphenyl (7.867%) and 9,12-Octadecadienoic acid (7.25%) were the predominant in the volatile oils of A. halodendron Turcz., whereas these constituents did not exist in the other two plants. And the study investigated the effect of three plants against CCl₄-induced hepatotoxicity in mice. 70% ethanol extracts of A. halodendron Turcz. showed weaker protective effect than the other two plants. It suggested that they provide a basis for the identification of the A. halodendron Turcz. from the other two plants and the ethanol extract from three plants exerted a protecting effect against hepatotoxicity.     

Antioxidant activity of different parts of Pistacia khinjuk Stocks fruit and its correlation to phenolic composition

The fruits of Pistacia khinjuk Stocks were collected from Ilam province, Iran. The aim of this study was to analyse antioxidant capacity and phenolic composition of different parts of P. khinjuk fruit. The antioxidant capacity of extracts was measured using different assays: ferric reducing ability of plasma, 2,2-diphenyl-1-picrylhydrazyl and nitric oxide radical scavenging. The phenolic composition of P. khinjuk fruit is reported for the first time. Amongst different parts of the fruit analysed in this study, hull extract contained the highest total phenolic and flavonoid contents. We observed a high correlation between different antioxidant activity and total phenolic and flavonoid contents. Therefore, antioxidant capacity can be related to total phenolic and flavonoid contents. A correlation analysis revealed that ascorbic acid, gallic acid, rutin, caffeic acid, ferulic acid and sinapic acid were the phenolic compounds mainly responsible for antioxidant power of the fruit extracts.     

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.     

Chemical composition and evaluation of antinociceptive activity of the essential oil of Stevia serrata Cav. from Guatemala

The composition and the antinociceptive activity of the essential oil of Stevia serrata Cav. from a population located in the west highlands of Guatemala were evaluated. A yield of 0.2% (w/w) of essential oil was obtained by hydrodistillation of the dried aerial parts of the plant. The essential oil analysed by GC-FID and GC-MS showed a high content of sesquiterpenoids, with chamazulene (60.1%) as the major component and 91.5% of the essential oil composition was identified. To evaluate antinociceptive activity in mice, the essential oil of S. serrata Cav. was administered as gavage, using three different doses. In the formalin test, the animals were pre-treated with oral doses of the essential oil before the administration of formalin. Oral administration of S. serrata Cav. essential oil produced a marked antinociceptive activity. Therefore, the plant could be domesticated as a source of essential oil rich in chamazulene for developing medicinal products.     

Evaluation of antibacterial and antioxidant activities of Artemisia campestris (Astraceae) and Ziziphus lotus (Rhamnacea)

The present work quantitatively evaluates the antimicrobial and antioxidant potentials of two Libyan folk medicinal plants [Artemisia campestris (Astraceae) and Ziziphus lotus (Rhamnacea)] that commonly grow in the south of Libya. The crude methanolic leaves extracts of both plants are appreciably active against Gram-positive species, associated with week anti-Gram-negative activity. These two plant extracts also showed reasonably high contents of polyphenolics and alkaloids, with minimal inhibitory concentrations between 12.5–25 and 250–1000 μg/ml for Gram-positive and Gram-negative species, respectively. Results collectively suggest that A. campestris and Z. lotus are not only reliable natural sources of antimicrobials but also potential sources of phenolic antioxidants and hence could be nominated for future intensive studies.     

Antimicrobial and antioxidant phytochemicals in leaf extracts of Bergenia ligulata: a Himalayan herb of medicinal value

Phenolic and flavonoid contents in leaf extracts of Bergenialigulata have been analysed for their contribution in antimicrobial and antioxidant activities. The extracts were prepared in three solvents (separately) following maceration and soxhelt methods. The antimicrobial activity was tested using disc diffusion assay against a range of microorganisms along with the determination of minimum inhibitory concentration (MIC), while the antioxidant activity was tested following DPPH assay. Leaf extracts exhibited antimicrobial activity against all the three groups of microorganisms; results coincided with respective MIC. In general, the methanol extracts prepared through maceration favoured the determination of antimicrobial and antioxidant activities. Maximum values for phenolic and flavonoid contents were obtained in macerated methanol and ethyl acetate extracts, respectively. The statistical correlations exhibited the extent of the contribution of phenolic and flavonoid contents in antimicrobial and antioxidant activities and also indicated the involvement of other plant metabolites.     

Thymus algeriensis and Artemisia herba-alba Essential Oils: Chemical Analysis,Antioxidant Potential and In Vivo Anti-Inflammatory,Analgesic Activities,and Acute Toxicity

The study of bioactive molecules of natural origin is a focus of current research. Thymus algeriensis and Artemisia herba-alba are two medicinal plants widely used by the Moroccan population in the traditional treatment of several pathologies linked to inflammation. This study aimed to evaluate the single and combined antioxidant, anti-inflammatory and analgesic effects of the essential oils extracted from these two medicinal plants, and also their potential toxicity. Essential oils were extracted using hydro-distillation in a Clevenger-type apparatus. The antioxidant activity was evaluated by two methods: the scavenging of the free radical DPPH, and the reduction in iron. Anti-inflammatory activity was evaluated by evaluating the edema development induced by carrageenan injecting, while the analgesic power was evaluated according to the number of abdominal contortions induced by the intraperitoneal injection of acetic acid (0.7%). The acute oral toxicity was performed to assess the potential toxicity of the studied EOs, followed by an analysis of the blood biochemical parameters. The results of the two antioxidant tests indicated that our extract mixture exhibits good iron reduction capacity and very interesting DPPH free radical scavenging power, with an IC₅₀ of around 4.38 ± 0.98 μg/mL higher than that of the benchmark antioxidant, BHT. The anti-inflammatory test demonstrated that the mixture administered orally at a dose of 150 mg/kg has a better activity, exceeding that of 1% Diclofenac, with a percentage of maximum inhibition of the edema of 89.99 ± 4.08. The number of cramps in the mice treated with the mixture at a dose of 150 mg/kg is significantly lower (29.80 ± 1.92) than those of the group treated with Tramadol (42.00 ± 2.70), respectively. The toxicity results show no signs of toxicity with an LD₅₀ greater than 150 mg/Kg. These interesting results show that the two plants’ EOs had an important anti-inflammatory, analgesic, and antioxidant activity, and also a powerful synergistic effect, which encourages further in-depth investigations on their pharmacological proprieties.     

Flavone glucosides from Artemisia juncea

A new flavone glucoside, 4′,5-dihydroxy-3′,5′,6-trimethoxyflavone-7-O-β-D-glucoside was obtained from aerial parts of Artemisia juncea, together with the known flavone eupatilin (5,7-dihydroxy-3′,4′,6-trimethoxyflavone). The compounds were comprehensively analytically characterized by IR, UV, NMR and HR-MS, and their chemical structures ascertained. The EtOAc fraction of A. juncea showed the strongest DPPH radical scavenging ability as well as reducing power (in CUPRAC and FRAP assays) and phosphomolybdenum activity. This fraction also exhibited the strongest inhibitory effects on tyrosinase. Additionally, the best antidiabetic effects were observed for eupatilin and the CHCl₃ fraction.     

Two new phenolic compounds from Artemisia sphaerocephala

Two new phenolic compounds were isolated from whole plant of Artemisia sphaerocephala. The structures were elucidated on the basis of spectroscopic methods as 4-(1-hydroxylethyl)-phenol-1-O-b-D-glucopyranoside and 4-O-acetophenone-b-D-gluco- pyranosyl-(1-3)-b-D-glucopyranoside.     

Evaluation of the antioxidant and antibacterial properties of ethanol extracts from berries,leaves and stems of Hedera pastuchovii Woron. ex Grossh

This study was designed to examine the total phenolic and flavonoid contents, radical scavenging and antibacterial activity of the ethanolic extracts from leaves, berries and stems of Hedera pastuchovii Woron. ex Grossh. The berry extract, which contained the highest phenolic and flavonoid compounds, showed an appreciable DPPH^√ scavenging ability in comparison with leaf and stem extracts. The various extracts exhibited moderate to good activity against both Gram-negative and Gram-positive bacteria, and the effectiveness of leaf extract was higher for all tested bacteria.     

Two new flavonoids from Artemisia argyi with their anticoagulation activities

A new flavone glycoside, eupatilin 7-O-β-d-glucopyranoside (1) and a new flavone, 5,6,2′,4′-tetrahydroxy-7,5′-dimethoxyflavone (2), were isolated from Artemisia argyi. Their structures were unambiguously elucidated by extensive spectroscopic analysis. Both flavonoids were evaluated for in vitro anticoagulation activities. Compound 1 significantly extended thrombin time. Compound 2 had obvious effect in increasing prothrombin time.     

Artemisia santolinifolia-Mediated Chemosensitization via Activation of Distinct Cell Death Modes and Suppression of STAT3/Survivin-Signaling Pathways in NSCLC

Conventional chemotherapy remains an integral part of lung cancer therapy, regardless of its toxicity and drug resistance. Consequently, the discovery of an alternative to conventional chemotherapy is critical. Artemisia santolinifolia ethanol extract (AS) was assessed for its chemosensitizer ability when combined with the conventional anticancer drug, docetaxel (DTX), against non-small cell lung cancer (NSCLC). SRB assay was used to determine cell viability for A549 and H23 cell lines. The potential for this combination was examined by the combination index (CI). Further cell death, analyses with Annexin V/7AAD double staining, and corresponding protein expressions were analyzed. Surprisingly, AS synergistically enhanced the cytotoxic effect of DTX by inducing apoptosis in H23 cells through the caspase-dependent pathway, whereas selectively increased necrotic cell population in A549 cells, following the decline in GPX4 level and reactive oxygen species (ROS) activation with the highest rate in the combination treatment group. Furthermore, our results highlight the chemosensitization ability of AS when combined with DTX. It was closely associated with synergistic inhibition of oncogenesis signaling molecule STAT3 in both cell lines and concurrently downregulating prosurvival protein Survivin. Conclusively, AS could enhance DTX-induced cancer cells apoptosis by abrogating substantial prosurvival proteins’ expressions and triggering two distinct cell death pathways. Our data also highlight that AS might serve as an adjunctive therapeutic option along with a conventional chemotherapeutic agent in the management of NSCLC patients.     

Unusual Guaiane Sesquiterpenoids from Artemisia rupestris

Two new guaiane sesquiterpenoids, (1β,5β)‐1‐hydroxyguaia‐4(15),11(13)‐dieno‐12,5‐lactone ( 1 ) and 1,5‐epoxy‐4‐hydroxyguai‐11(13)‐en‐12‐oic acid ( 2 ), together with five known compounds, rupestonic acid ( 3 ), strobilactone A ( 4 ), antiquorin ( 5 ), isosclerone ( 6 ), and 5‐hydroxy‐2′,3′,4′,7,8‐pentamethoxyflavone ( 7 ), were isolated from a 95% EtOH extract of Artemisia rupestris. Compounds 1 and 2 are rare examples of guaiane sesquiterpenoids, incorporating a 12,5‐lactone group or featuring a 1,5‐epoxy ring, respectively. The structures of 1 and 2 were identified by various spectroscopic methods. Compounds 1, 4 , and 5 exhibited moderate cytotoxic activities against the human lung cancer 95‐D cell line with IC₅₀ values of 11.3, 19.8, and 34.5 μM , respectively.     

OXYGENATED FATTY ACIDS FROM NEUTRAL LIPIDS OF Artemisia leucodes SEEDS

Three epoxy-, fifteen monohydroxy-, and three dihydroxyacids from lipids ofArtemisia leucodesSch. Seeds were identified using chemical, chromatographic, and spectral analyses.     

Antioxidant capacities and total phenolic contents increase with gamma irradiation in two types of Malaysian honey

Two types of monofloral Malaysian honey (Gelam and Nenas) were analyzed to determine their antioxidant activities and total phenolic and flavonoid contents, with and without gamma irradiation. Our results showed that both types of honey can scavenge free radicals and exhibit high antioxidant-reducing power; however, Gelam honey exhibited higher antioxidant activity (p < 0.05) than Nenas honey, which is in good correlation (r = 0.9899) with its phenolic contents. Interestingly, we also noted that both irradiated honeys have higher antioxidant activities and total phenolic and flavonoid contents compared to nonirradiated honeys by Folin-Ciocalteu and UV-spectrophotometry methods, respectively. However, HPLC analysis for phenolic compounds showed insignificant increase between irradiated and nonirradiated honeys. The phenolic compounds such as: caffeic acid, chlorogenic acid, ellagic acid, p- coumaric acid, quercetin and hesperetin as indicated by HPLC method were found to be higher in Gelam honey versus Nenas honey. In conclusion, irradiation of honey causes enhanced antioxidant activities and flavonoid compounds.     

Extraction,Isolation and Characterization of Bioactive Compounds from Artemisia and Their Biological Significance: A Review

Diverse medicinal plants such as those from the genus Artemisia have been employed globally for centuries by individuals belonging to different cultures. Universally, Artemisia species have been used to remedy various maladies that range from simple fevers to malaria. A survey conducted by the World Health Organization (WHO) demonstrated that 80% of the global population is highly reliant on herbal medicine for their primary healthcare. WHO recommends artemisinin-based combination therapies (ACT) for the treatment of global diseases such as malaria. Artemisinin is a bioactive compound derived from Artemisia annua leaves. It is a sesquiterpene endoperoxide with potent antimalarial properties. This review strives to instill natural products to chemists and others in diverse fields with a heterogeneous set of knowledge compiled from multifaceted researchers and organizations in literature. In particular, the various Artemisia species and effective extraction, isolation, and characterization methodologies are discussed in detail. An in-depth investigation into the literature reveals that divergent species of Artemisia exhibit a vast array of biological activities such as antimalarial, antitumor, and anti-inflammatory activities. There is substantial potential for bioactive compounds from Artemisia to provide significant relief from differing human ailments, but more meticulous research in this field is needed.