Phenolic constituents of the aerial parts of Impatiens glandulifera Royle (Balsaminaceae) and their antioxidant activities

As a continuation of investigating Impatiens L. genus, eight flavonoids, eriodyctiol, eriodyctiol 7-O-β-?-glucoside, kaempferol 3-O-β-?-glucoside, kaempferol 3-O-β-?-galactoside, kaempferol 3-rhamnosyl-di-glucoside, kaempferol 3-O-β-?-rutinoside, quercetin 3-O-β-?-glucoside and quercetin 3-O-β-?-galactoside, two phenolic acids – p-hydroxybenzoic acid and protocatechuic acid, and 2-methoxynaphthalene-1,4-dione were isolated from the aerial parts of I. glandulifera collected in Poland. The structures of the compounds were established by analysis of their spectroscopic (¹H and ¹³C NMR) and spectrometric (MS) data, as well as by comparison of these with those reported in the literature. Quercetin 3-O-β-?-glucoside, kaempferol 3-O-β-?-galactoside and kaempferol 3-O-β-?-rutinoside were isolated for the first time from the investigated taxon. In addition, the antioxidant activities in different tests of all obtained compounds were evaluated. The results clearly showed that among analyzed constituents, quercetin 3-O-β-?-glucoside exhibited antioxidant activity comparable or better than ascorbic acid and Trolox which were used as a positive control.     

Chemical composition,antimicrobial and antioxidant activities of the essential oil of Psammogetoncanescens

This study reports the chemical composition, antimicrobial activity and antioxidant properties of Psammogeton canescens essential oil (EO) and its main compounds. The EO was obtained from the aerial parts of P. canescens by hydrodistillation and analysed by using GC/MS. The main constituent was β-bisabolene (25%), followed by α-pinene (20%), apiole (15.34%), γ-terpinene (7.34%), p-cymene (5.35%), β-pinene (5.41%), camphene (5.12%), dill apiole (5%), myrcene (4.54%), colchicine (0.56), sylvestrene (0.56%), β-caryophyllene (0.45%), caryophyllene oxide (0.43%), (Z)-β-farnesene (0.32%), cembrene (0.21%), folic acid (0.21%), germacrene D (0.14) and β-sesquiphellandrene (0.13). β-Bisabolene exhibited strong antioxidant activity (14 ± 0.8 μg/mL). The EO of P. canescens was particularly active against Candida albicans and Escherichia coli, with the lowest minimum inhibitory concentration and minimum bactericidal/fungicidal concentration values. In conclusion, these results support the use of the EO and its main compounds for their antioxidant properties and antimicrobial activity.     

Identification of Anti-Proliferative Compounds from Genista monspessulana Seeds through Covariate-Based Integration of Chemical Fingerprints and Bioactivity Datasets

Genista monspessulana (L.) L.A.S. Johnson (Fabaceae) is a Mediterranean plant introduced to South America and other regions for ornamental purposes. However, it is considered an invasive shrub due to its reproductive vigor in many areas. Unlike other Genista plants, G. monspessulana has few studies disclosing its biologically active components, particularly cytotoxic agents against cancer cells. Thus, as part of our research on anti-proliferative bioactives, a set of ethanolic seed extracts from ten accessions of G. monspessulana, collected in the Bogotá plateau, were evaluated against four cell lines: PC-3 (prostate adenocarcinoma), SiHa (cervical carcinoma), A549 (lung carcinoma), and L929 (normal mouse fibroblasts). Extracts were also analyzed through liquid chromatography coupled with mass spectrometry (LC/MS) to record chemical fingerprints and determine the composition and metabolite variability between accessions. Using multiple covariate statistics, chemical and bioactivity datasets were integrated to recognize patterns and identify bioactive compounds among studied extracts. G. monspessulana seed-derived extracts exhibited dose-dependent antiproliferative activity on PC-3 and SiHa cell lines (>500 µg/mL < IC₅₀ < 26.3 µg/mL). Seven compounds (1–7) were inferred as the compounds most likely responsible for the observed anti-proliferative activity and subsequently isolated and identified by spectroscopic techniques. A tricyclic quinolizidine (1) and a pyranoisoflavone (2) were found to be the most active compounds, exhibiting selectivity against PC-3 cell lines (IC₅₀ < 18.6 µM). These compounds were used as precursors to obtain a quinolizidine-pyranoisoflavone adduct via Betti reaction, improving the activity against PC-3 and comparable to curcumin as the positive control. Results indicated that this composition–activity associative approach is advantageous to finding those bioactive principles efficiently within active extracts. This correlative association can be employed in further studies focused on the targeted isolation of anti-proliferative compounds from Genista plants and accessions.     

Polyphenolic contents and antioxidant activities of aerial parts of Salvia multicaulis from the Iran flora

Abstract

Folk medicine sometimes involves the use of salvia species for therapeutic purposes. Polyphenols with the highest amounts included rosmarinic acid (7.358mg/g), catechin (1.5?mg/g), vanillin (1.00?mg/g), chlorogenic acid (0.53?mg/g), quercetin (0.16?mg/g), and p-coumaric acid (0.015). Furthermore, the results showed that S. multicaulis has a high content of total phenol (4.39?mg/g) and DPPH activity (8.44?mg/g). Salvia multicaulis could be potentially used as a medicinal plant because of its antioxidant activity and polyphenol content.     

Chemical composition,antioxidant and antibacterial properties of Pteranthus dichotomus from Algerian Sahara

The phytochemical study of ethyl acetate and n-butanol extracts of Pteranthus dichotomus Forssk. led to the isolation and identification of 11 compounds, including three glycolipids 1–3, one lignan 4, three flavonoids 5–7 and four phytosterols 8–11. Structures of the isolated compounds have been elucidated by analysis of 1D and 2D NMR data, and mass spectrometry EI-MS and ESI-MS and by comparison with literature data. Furthermore, the ethyl acetate and n-butanol extracts were examined for their antioxidant and antibacterial activities. The results showed that both extracts (PDAC and PDBU) had a moderate antioxidant activity (IC50 = 375.514 μg/mL and 691.333 μg/mL) respectively.     

Chemical constituents of the aerial parts of Scutellaria lateriflora and their alpha-glucosidase inhibitory activities

MeOH extracts of 37 herbs were tested in screening experiments for rat intestinal alpha-glucosidase. The MeOH extract of the aerial parts of Scutellaria lateriflora L. (Lamiaceae) significantly inhibited sucrase and maltase activities, using sucrose and maltase as the substrates. Enzyme inhibition guided-fractionation of the MeOH extract of S. lateriflora resulted in the isolation of a new diterpene glucoside, deacetylajugarin-IV 18-O-beta-D-glucopyranoside (1), along with 20 known phenolics (2-21). The structures of 1-21 were elucidated on the basis of MS and NMR data analyses. Baicalein (4) and baicalin (10), a glycoside of 4, showed moderate sucrase inhibitory activities at IC50 values of 14.9 and 36.3 microM, respectively, whereas luteolin (3), acteoside (16), leucosceptoside A (18), and isoacteoside (20) showed weak inhibitory activities at IC50 values of 811, 522, 727, and 443 microM, respectively. This is the first report on mammalian alpha-glucosidase inhibitory activities of S. lateriflora extract and identification of the constituents responsible for the activities. Apigenin (2), luteolin (3), 6-methoxyluteolin 4'-methyl ether (6), isoscutellarin 8-O-beta-D-glucuronide (7), luteolin 7-O-beta-D-glucuronide (9), wogonin 7-O-beta-D-glucuronide methyl ester (12), eriodictyol (13), naringenin (14), naringenin 7-O-beta-D-glucuronide (15), jionoside D (17), leucosceptoside A (18), and (+)-syringaresinol 4'-O-beta-D-glucopyranoside (21) were isolated from this plant for the first time. The inhibitory properties of S. lateriflora extract against alpha-glucosidase provide a prospect for its antidiabetic usage.     

Extraction technology,component analysis,and in vitro antioxidant and antibacterial activities of total flavonoids and fatty acids from Tribulus terrestris L. fruits

The current study focused on the extraction technology, components analysis, in vitro antioxidant and antibacterial activities of total flavonoids and fatty acids from Tribulus terrestris L. fruits. The extraction process of total flavonoids and fatty acids was optimized by the response surface method, and the compositions were identified from the two extracts by HPLC–DAD–ESI–MS^? and GC–MS, respectively. In addition, the antioxidant and antibacterial activities were evaluated by assay of ABTS, DPPH radical scavenging activity, ferric reducing antioxidant power and minimal inhibitory concentration. The yields of total flavonoids and fatty acids were 0.46 and 9.76% under the optimized conditions. Moreover, nine and eight compositions were identified from the two extracts based on the related references, respectively. In addition, total flavonoids and fatty acids extracts both exhibited certain antioxidant and antibacterial activities. The present findings suggest that total flavonoids extracted from T. terrestris L. fruits comprised a more interesting candidate than fatty acids for the research and development of natural and healthy antioxidants and antibacterial agents for the pharmaceutical and food industries.     

Synthesis of new annulated pyridazine derivatives and studying their antioxidant and antimicrobial activities

Benzil was reacted with cyanoacetohydrazide under microwave irradiation to give 3-oxo-5,6-diphenyl-2,3-dihydropyridazine-4-carbonitrile 1 which used as starting material for the synthesis of new heterocyclic compounds. Chlorination of pyridazinone 1 with POCl₃ afforded the chloro-pyridazine derivative 3, which then condensed with 2-aminothiazole or hydrazine hydrate to produce 3,4-diphenyl-5H-thiazolo[3′,2′:1,2]pyrimido[4,5-c]pyridazin-5-one 5 or 3-hydrazinyl-5,6-diphenylpyridazine-4-carbonitrile 6, respectively. New Schiff bases were obtained by condensation reactions of compound 6 with different aldehydes. On the other hand, compound 6 reacted with different carbon electrophiles naming acetyl acetone, diethyl malonate, and phenyl isothiocyanate producing new pyarazolo-pyridazine derivatives 11, 12, and 14, respectively. Chemical structures of all newly synthesized compounds were confirmed on the basis of spectral data and had been screened for antimicrobial and antioxidant activity.     

Chemical constituents,in vitro antioxidant and antimicrobial properties of ethyl acetate extract obtained from Cytisus triflorus l’Her

Abstract

The present study investigates the phenolic composition, antioxidant and antimicrobial activities of an ethyl acetate extract from C. triflorus L’Her. The phytochemical study on the aerial parts of C. triflorus belonging to the Fabaceae family led to the isolation and structural elucidation of 5-Hydroxy-7-O-glucosylflavone (P1), 5-Hydroxy-7-O-galactosylflavone (P2), 5,7-Dihydroxy-flavone (P3), 5,7,3’-Trihydroxy,4’-methoxy-flavone (P4). These compounds were identified by 1D and 2D NMR combined analysis as well as by UV.

Ethyl acetate extract of C. triflorus showed a significant and dose-dependent antioxidant activity in vitro, related to the presence of phenolics (180.33?±?12.22?µg GAE/mg) and flavonoids (16.78?± 1.54?µg QE/mg). The antimicrobial activity was evaluated in vitro against Staphylococcus aureus CECT 240 and Escherichia coli CECT 4099, by agar-diffusion method. The most active antibacterial activity was expressed by ethyl acetate extract of C. triflorus against Gram-positive bacteria S. aureus. The gathered results suggest that C. triflorus polyphenols and flavonoids are closely associated to its antioxidant and antimicrobial properties.     

Chemical constituents,anticancer, antimicrobial and antioxidant activities of essential oil from Anaphalis lacteal grown in Qinghai-Tibet Plateau

The chemical constituent of the essential oil from Anaphalis lacteal was determined; 31 compounds, representing 93.91% of the total oil, were identified by gas chromatography–mass spectrometry analysis. Three Gram-positive bacteria species, three Gram-negative bacteria species and four fungi were used to determine antimicrobial activity; the results revealed that the essential oil had a remarkable antimicrobial effect against bacteria and a susceptive effect against fungus. The oil also possessed more efficient free-radical scavenging activities than butylated hydroxytoluene (BHT) with 50% inhibitory concentration (IC₅₀) value 31 μg/mL (40 μg/mL for BHT). MTT assay illustrated that the oil expressed certain effect in inhibiting the growth of HeLa and Hep-6 cancer cells.     

Chemical composition,antioxidant, antimicrobial and anticancer activities of the essential oil from the rhizomes of Zingiber striolatum Diels

Abstract

The chemical composition and biological activities of the essential oil (EO) from the rhizomes of Zingiber striolatum Diels were reported for the first time. Forty-five compounds were identified, and represented 95.7% of the total composition of the EO. The predominant components of the EO were β-phellandrene (24.0%), sabinene (17.3%), β-pinene (11.4%), geranyl linalool (8.6%), terpinen-4-ol (8.3%), α-pinene (5.6%) and crypton (4.5%). The EO revealed a weak DPPH and ABTS radical-scavenging activity. The EO exhibited significant antimicrobial activity with the inhibition zones (12.86–24.62?mm) and MIC (0.78–3.12?mg/mL) against Enterococcus faecalis, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Candida albicans. The EO showed significant cytotoxicity against human leukemic (K562), lung cancer (A549) and prostatic carcinoma (PC-3) cell lines with the IC₅₀ values of 29.67, 48.87 and 86.05?μg/mL, respectively. Thus, the EO could be regarded as a bioactive natural product with potential for utilization in the cosmetic and pharmaceutical industry.     

Comparative study of the chemical profiling,antioxidant and antimicrobial activities of essential oils of different parts of Thymus willdenowii Boiss & Reut

The analysis of Thymus willdenowii Boiss &; Reut essential oils (TW EOs) shows 33 components accounting for (96.3–97.7%) of all identified. The main constituents of TW EOs were thymol (35.5–47.3%), p-cymene (13.9–23.8%), γ-terpinene (8.9–20.3%). The antioxidant assays revealed that all TW EOs tested showed strong activities, the antimicrobial effect of TW EOs has been tested against isolated clinical strains of Proteus mirabilis (ATCC 35659), Escherichia coli (ATCC 25922), Candida albicans (ATCC 10231), Bacillus cereus (ATCC 10876), and Aspergillus brasilliensis (ATCC 16404). The antimicrobial test indicates that TW EOs show an inhibition effect against all the tested bacteria with a MIC of 6.9 to 27.6 μg/mL^?1. These results proving that the essential oils extracted from Thymus willdenowii Boiss &; Reut may be a new potential source of natural antimicrobial applied in pharmaceutical and food industries.     

Chemical composition,antioxidant, antibacterial and cytotoxic activities of essential oil of Leontopodium leontopodioides (Willd.) Beauverd

The essential oil (EO) from the aerial parts of Leontopodium leontopodioides (Willd.) Beauverd was obtained by hydrodistillation and analysed by GC–FID and GC–MS. Sixty-five compounds were identified which represent 96.2% of the total composition of the EO. The major components of the EO were palmitic acid (11.6%), n-pentadecanal (5.7%), linalool (3.8%), β-ionone (3.3%), hexahydrofarnesyl acetone (3.2%), bisabolone (3.2%) and β-caryophyllene (3.2%). The EO exhibited an excellent antibacterial activity against Staphylococcus aureus and Bacillus subtilis according to the MIC values tested by micro-dilution method. It also exhibited a significant cytotoxicity against HepG2 and MCF-7 cell lines with the IC₅₀ values of 67.44 and 70.49 μg/mL according to the MTT assay. However, the antioxidant activity test revealed that the EO exhibited a weak DPPH radical-scavenging activity. In conclusion, the EO of L. leontopodioides could be regarded as a bioactive natural product and deserves further study for its potential therapeutic effects.     

Chemical composition and antioxidant activity of aerial parts of Ferula longipes Coss. ex Bonnier and Maury

This is the first study on the phytochemistry and antioxidant activity of Ferula longipes Coss. ex Bonnier and Maury (Apiaceae). A new flavonoid quercetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-[2-O-caffeoyl]-glucopyranoside (1), along with 10 known compounds kaempferol-3-O-α-L-rhamnopyranoside (2), quercetin-3-O-α-L-rhamnopyranoside (3), kaempferol-3-O-ß-D-glucopyranoside-7-O-α-L-rhamnopyranoside (4), isorhamnetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-glucopyranoside (5), quercetin-3-O-α-L-rhamnopyranoside-7-O-ß-D-glucopyranoside (6), isorhamnetin-3,7-di-O-β-D-glucopyranoside (7), apigenin (8), apigenin-7-O-ß-D-glucopyranoside (9), 3,5-dicaffeoylquinic acid (10), deltoin (11) were isolated from the aerial parts of Ferula longipes Coss. Structures elucidation was performed by comprehensive 1D and 2D NMR analyses, mass spectrometry and by comparison with literature data. The compounds 1, 3, 4, 6, 7 and 10 were evaluated for their antioxidant activity, compound 1 exhibited the best antiradical activity potential and showed IC₅₀ and A_0.5 values 5.70, 7.25, 5.00, and 2.63 μg/mL towards DPPH free radical-scavenging, ABTS, CUPRAC, and reducing power assays, respectively compared with BHA, BHT and ascorbic acid which were used as positive controls.     

Insecticidal,cytotoxic and anti-phytopathogenic fungal activities of chemical constituents from the aerial parts of Ferula sinkiangensis

Abstract

A new rare monoterpene coumarin (1) and its two known analogues (2–3), together with two sesquiterpenes (6–7) and ferulic acid (8) were isolated from the aerial parts of Ferula sinkiangensis. The structure of new compound was established on the basis of 1D and 2D NMR data and HRESIMS data interpretation. Insecticidal, cytotoxic and anti-phytopathogenic fungal activities of isolated compounds were evaluated against third-instar larvae of Spodoptera exigua and its cell line, and three plant pathogenic fungi respectively. Compounds 1–3 and 6–7 were found to be more effective contact toxicity to S. exigua with the corrected mortality values of 38.89%-58.89% at 10?μg/larva doses for 24?h. Further studies showed that compounds 3 and 6 exhibited cell growth inhibitory activity against S. exigua cell line with the EC₅₀ values of 22.78 and 14.64?µM for 72?h. In addition, compound 6 exhibited potent antifungal activity with MICs?=?16–32?µg/mL.     

A new indole alkaloid,antioxidant and antibacterial activities of crude extracts from Saccocalyx satureioides

Abstract

The new acylated indole alkaloid glucoside indole-3-carboxylic acid-(6'-O-caffeoyl)-β-D-glucoside 1 has been isolated from the ethyl acetate (EtOAC) extract of Saccocalyx satureioides Coss. & Dur. (Lamiaceae) together with eight known secondary metabolites 2-9. Two indoles 2 and 3, five methylated flavone aglycones 4-8 and one monoterpene glucoside 9 were reported for the first time in the genus Saccocalyx. The structural elucidation of these compounds was accomplished by spectroscopic methods including 1?D (¹H and ¹³C) and 2?D (COSY, HSQC and HMBC) NMR techniques, and mass spectrometry, and by comparison with literature data. Light petroleum, EtOAc, chloroform and n-butanol (n-BuOH) extracts of S. Satureioides were screened for their antioxidant activity using DPPH radical scavenging and β-carotene bleaching methods. The antibacterial activity of these extracts indicates that n-BuOH and EtOAc extracts possess the strongest activity.     

Chemical composition and in vitro anticancer,antimicrobial and antioxidant activities of essential oil and methanol extract from Rumex nervosus

Chemical composition, antioxidant, anticancer, and antimacrobial activities of essential oil obtained from leaves of Rumex nervosus has been evaluated here for the first time. GC/MS analysis reveals the presence of Palmitoleic Acid (28.35%) and Palmitic acid, (25. 37%) as their methyl ester as major components. The essential oil showed significant DPPH radical scavenging activity (94.907 ± 0.1089% and 94.003 ± 0.0749%) at concentration (100 and 80) μg/mL respectively. The oil showed promising activity against staph aureus, while showed weak activity against (Hela and 3T3) cell lines. The crude extract / fractions of R. nervosus (leaves) showed significant antioxidant activity at dose (100 and 80) μg/mL. Futhermore the crude showed significant activity against (MCF-7 and MDA-MB-231) cell lines with IC₅₀ (20.5138 ± 0.933 and 25.1728 ± 0.9176) μg/mL respectively, and chloroform fraction showed good activity against (MCF-7 and MDA-MB-231) cell lines with IC₅₀ (31.154 ± 0.965 and 42.269 ± 2.1045) μg/mL.     

Chemical constituents of essential oil of endemic Rhanterium suaveolens Desf. growing in Algerian Sahara with antibiofilm,antioxidant and anticholinesterase activities

Twenty compounds were detected in the essential oil of Rhanterium suaveolens representing 98.01% of the total oil content. Perillaldehyde (45.79%), caryophyllene oxide (24.82%) and β-cadinol (5.61%) were identified as the main constituents. In β-carotene–linoleic acid assay, both the oil and the methanol extract exhibited good lipid peroxidation inhibition activity, with IC₅₀ values of 17.97 ± 5.40 and 11.55 ± 3.39 μg/mL, respectively. In DPPH and CUPRAC assays, however, the methanol extract exhibited a good antioxidant activity. The highest antibiofilm activity has been found 50.30% against Staphylococcus epidermidis (MU 30) at 20 μg/mL for essential oil and 58.34% against Micrococcus luteus (NRRL B-4375) at 25 mg/mL concentration for methanol extract. The in vitro anticholinesterase activity of methanol extract showed a moderate acetylcholinesterase inhibitory (IC₅₀ = 168.76 ± 0.62 μg/mL) and good butyrylcholinesterase inhibitory (IC₅₀ = 54.79 ± 1.89 μg/mL) activities. The essential oil was inactive against both enzymes.     

A new flavonol glycoside and other flavonoids from the aerial parts of Taverniera aegyptiaca

Isolation of flavonoids from the aerial parts of Taverniera aegyptiaca Bioss. (Fabaceae) led to identification of one new flavonol glycoside, isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→2)-α-l-arabinopyranoside (1), along with eleven compounds, which previously have not been isolated from this plant quercetin-3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (2), isorhamnetin-3-O-α-l-arabinopyranoside (3), quercetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (4), isorhamnetin-3-O-α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside (7), isorhamnetin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (8), isorhamnetin 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-glucopyranoside] (9), kaempferol 3-O-α-l-rhamnopyranosyl-(1→2)-[α-l-rhamnopyranosyl-(1→6)-β-d-galactopyranoside] (10), isorhamnetin (11), 4,4′-dihydroxy-2′-methoxychalcone (12), formononetin (13) and calycosin (15)] and some compounds already known from this plant [quercetin-3-O-robinobioside (5), isorhamnetin-3-O-robinobioside (6), afrormosin (14) and odoratin (16)].     

Chemical constituents and allelopathic activity of Machaerium eriocarpum Benth.

Abstract

The analysis by HPLC-PDA of the hydroalcoholic extract of the leaves of M. eriocarpum together with the injection of the fractions containing the already identified metabolites allowed the detection of at least 5 flavonoids, of which two are derived from apigenin and three from luteolin. After isolating larger amounts of isovitexin (I), assays were performed to evaluate the allelopathic activity together with the crude extract. The results show that the initial inhibition indexes were very similar to those observed in the treatments with F17 (Fraction enriched in isovitexin) and F18 (isovitexin), mainly in the concentrations of 500 and 1000?mg L^?1. The index of the number of lateral roots, an increase of the inhibitory effect is observed with the increase of the concentration of M. eriocarpum extract.