Chemical composition, in vitro cytotoxic and antioxidant activities of the essential oil and major constituents of Cymbopogon jawarancusa (Kashmir)

The chemical composition of the hydrodistillate of aerial parts of Cymbopogon jawarancusa, a natural grass considered as major forage for animal nutrition, used in food because of the presence of sufficient concentration of minerals like calcium and potassium was analysed by capillary GC–FID, GC–MS and ¹³C NMR. Seventeen constituents representing 97.8% of the total oil with piperitone (58.6%) and elemol (18.6%) as major constituents were identified. In vitro cytotoxicity of the oil and its constituents on human cancer cell lines THP-1 (leukemia), A-549 (lung), HEP-2 (liver) and IGR-OV-1 (ovary) was evaluated by Sulphorhodamine-B assay. The oil was found to be more potent than its components against cancer cell lines tested with IC₅₀ of 6.5 μg/ml (THP-1), 6.3 μg/ml (A-549), 7.2 μg/ml (HEP-2) and 34.4 μg/ml (IGR-OV-1). Antioxidant activity of oil and its constituents was evaluated by DPPH assay. In conclusion, the results demonstrate potent cytotoxic and antioxidant effects of oil, and its components like piperitone, α-pinene, β-caryophyllene and β-elemene.     

Chemical composition,cytotoxic and antioxidant activity of the leaf essential oil of Photinia serrulata

The leaf essential oil of Photinia serrulata was obtained by hydrodistillation and analyzed by GC and GC-MS. Seventy-one components were identified in the essential oil and the main components of the oil were 10-epi-γ-eudesmol (12.72%), pinene (6.85%), sabinene (5.93%), α-humulene (5.87%) and α-thujene (5.47%). The in vitro cytotoxicity of the oil on human cancer cell lines Hela, A-549 and Bel-7402 was examined. The oil was found to be very active against all the three human tumor cell lines tested with low IC₅₀ of 0.0427 μl/ml (Hela), 0.0219 μl/ml (A-549) and 0.0301 μl/ml (Bel-7402). The oil was also found to possess antioxidant activity as demonstrated by the 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical method.     

Antioxidant activity and chemical constituents of essential oil and extracts of Rhizoma Homalomenae

Antioxidant activity and composition of essential oil and extracts of Rhizoma Homalomenae were determined. The extracts, especially the ethyl acetate extract (QJ4 fraction) of the aqueous residue after oil distillation, had considerable antioxidant potency which was significantly associated with their total phenolic and flavonoid contents, but the essential oil showed only weak or moderate activity. GC–MS analysis of the essential oil (yield: 0.82%, v/w) resulted in the identification of 77 compounds, accounting for 96.5% of the content of the oil. The major components, epi-α-cadinol (14.8%), α-cadinol (14.8%), α-terpineol (13.8%), linalool (11.1%), terpinen-4-ol (4.92%), and δ-cadinene (4.91%) constituted 64.3% of it. LC–MS/MS and HPLC analyses showed seven phenolic compounds (protocatechuic acid, vanillic acid, syringic acid, caffeic acid, p-coumaric acid, ferulic acid and apigenin) with a great amount in the ethyl acetate extract (QJ4 fraction). The strong antioxidant properties of the plant extracts may be attributed to the presence of these phenolics.     

Citrus paradisi and Citrus sinensis flavonoids: Their influence in the defence mechanism against Penicillium digitatum

Citrus peel is rich in flavanone glycosides and polymethoxyflavones. In view of their importance for industrial application as well as for their pharmacological properties, their content was analyzed in the mature fruits of several Citrus paradisi (grapefruit) and Citrus sinensis (orange) varieties, with a view to select the most interesting for isolation. The results shows that the Star Ruby grapefruit and the Sanguinelli orange stand out for their high contents of naringin and hesperidin, respectively. The presence of the polymethoxyflavones nobiletin, heptamethoxyflavone and tangeretin, could be ascertained in all the grapefruit varieties analysed. Higher polymethoxyflavone levels were recorded in orange, with Valencia Late showing the greatest nobiletin, sinensetin and tangeretin contents and Navelate the highest heptamethoxyflavone levels. An in vitro study revealed that these compounds acted as antifungal agents against Penicillium digitatum, the polymethoxyflavones being more active than the flavanones in this respect. The possible participation of these phenolic compounds in the defence mechanism of Citrus against P. digitatum is discussed.     

Chemical composition, mineral content and antioxidant activity of Verbena officinalis L.

Aqueous and hydroalcoholic extracts from Verbena officinalis L. were obtained and characterised. The analysis by HPLC-DAD and LC-MS allowed the detection and identification of three iridoids, fifteen flavonoids and four phenolic acid derivatives. Four flavonoids, scutellarein 7-diglucuronide (9), scutellarein 7-glucuronide (13), pedalitin 6-galactoside (15) and scutellarein 7-glucoside (19) are reported for the first time from this plant. In addition, three new flavonoids have been isolated: scutellarein 7-O-(2-O-feruloyl)-diglucuronide (5), pedalitin 6-O-diglucuronide (6) and pedalitin 6-O-(2-O-feruloyl)-diglucuronide (13). To our knowledge, these flavonoids have not been reported as natural products. Both extracts showed significant antioxidant activity using three in vitro model systems and the results have been correlated with total phenolic and total flavonoid contents. The results have allowed establishing an important relation structure-activity and significant correlations have also been found between the mineral content and the flavonoids present in both extracts.     

Chemical composition and biological activities of Algerian Thymus oils

The compositions of essential oils isolated from nine samples of three Thymus species (Thymus algeriensis, Thymus pallescens and Thymus dréatensis) were analysed by GC and GC–MS, and a total of 114 components were identified. T. pallescens collected from various regions showed a great similarity in their compositions and were characterised by carvacrol (44.4–57.7%), p-cymene (10.3–17.3%) and γ-terpinene (10.8–14.2%) as the major components for four samples; only one sample was thymol-rich (49.3%) with a small amount of carvacrol (9.0%). On the other hand, T. algeriensis showed a chemical polymorphism, even for samples from the same location, and two new chemotypes for this species were proposed. Oxygen-containing monoterpenes were the predominant class (76.3%) in T. dreatensis oil, with linalool (30.4%), thymol (20.2%) and geraniol (19.6%) as the principal constituents. The oils were screened for their possible antioxidant activities by four complementary assays, namely DPPH free radical scavenging, hydroxyl radical scavenging, inhibition of lipid peroxidation and reducing power. The two new chemotypes of T. algeriensis exhibited strong hydroxyl radical scavenging (IC₅₀ = 2.2–3.3 μg/ml), but were not or only slightly active against the other radicals and exhibited a weak reducing power. Despite their chemical similarity, T. pallescens oils sometimes produced significant differences in their antioxidant activities. The essential oils were also screened for their antimicrobial activity against five bacteria (three Gram-positive and two Gram-negative) and one yeast (Candida albicans). The tested essential oils showed antimicrobial activity against the microorganisms used, in particular against two important pathogens, C. albicans and Helicobacter pylori.     

The methoxyflavones in Citrus reticulata Blanco cv. ponkan and their antiproliferative activity against cancer cells

The major polymethoxyflavones in the fruit (ponkan) peels of Citrus reticulata Blanco cv. ponkan were identified as isosinensetin, sinensetin, nobiletin and tetramethyl-o-scutellarein by a combined separation using high-speed countercurrent chromatography and preparative high performance liquid chromatography, and structure elucidation by electrospray ionisation mass spectrometry (ESI-MS) and ¹H and ¹³C nuclear magnetic resonance (NMR). The antiproliferative activity of the four compounds against four cancer cell lines (A549, HL-60, MCF-7 and HO8910) showed that isosinensetin had a lower IC₅₀ value for MCF-7 and HO8910 cancer cell lines. Determination of polymethoxyflavones in ponkan peels from different cultivation regions displayed relatively steady contents of the four compounds and a higher content of isosinensetin, which suggested that ponkan peels are excellent sources of functional polymethoxyflavones that may help prevent female cancers, such as ovarian cancer and breast cancer.     

Antioxidative and anti-inflammatory properties of Citrus sulcata extracts

Citrus sulcata was subjected to ultrasound, high-pressure, and Soxhlet extractions. The antioxidant and anti-inflammatory activities of the extracts were evaluated qualitatively and quantitatively. The antioxidant content of the peel extract was twice that of the fruit extract. The quantitative analysis showed that the narirutin and hesperidin contents in the peel extracts were 8.8 and 7.5 mg/100 g, respectively. These extracts had a total phenolic content of 112.22 ± 2.89 gallic acid equivalent (GAE) mg/100 g, a total flavonoid content of 54.09 ± 1.01 rutin equivalent (RE) mg/100 g, DPPH radical scavenging activity of 46%, and antioxidant activity of 213.25 ± 2.82 μM of Trolox equivalents (TEAC). C. sulcata extracts could prevent hydrogen peroxide (H₂O₂)-induced oxidative stress, reduce expression of the inflammatory markers nuclear Factor kappa B (NFκB) and phosphorylated IκBα (p-IκBα) in A549 human lung carcinoma cells, and inhibit Lipopolysaccharide (LPS)-induced THP-1 monocyte differentiation to an extent of 85%.     

Juniperus sibirica Burgsdorf. as a novel source of antioxidant and anti-inflammatory agents

In order to examine antioxidant properties of methanol extracts of cones and needles of the unexplored Juniperus sibirica Burgsdorf. (Cupressaceae) species, various assays which measure free radical scavenging ability were carried out: DPPH, hydroxyl, superoxide anion and nitric oxide radical scavenger capacity test and reducing power (FRAP) assay. In all of the tests the extracts showed a potent antioxidant effect compared with BHT, a well-known synthetic antioxidant. In addition, the anti-inflammatory activity considering inhibitory potency toward COX-1 and 12-LOX was observed. Both extracts showed markedly anti-inflammatory activity, with needles having somewhat higher potency concerning both assays, reaching IC₅₀ at 1.29 mg/mL towards COX-1 and IC₅₀ at 1.34 mg/mL towards 12-LOX. Besides, in the extracts examined the total phenolic and flavonoid amounts were also determined, together with presence and content of the selected flavonoids: luteolin-7-O-glucoside, apigenin-7-O-glucoside, luteolin, apigenin, rutin and quercetin, which were studied using LC–MS/MS technique. LC–MS/MS analysis showed a noticeable content of natural products according to which the examined J. sibirica Burgsdorf. species could well be regarded as a promising new source of bioactive natural compounds, which can be used both as a food supplement and a remedy.     

Potential bioactive phenolics of Macedonian Sideritis species used for medicinal “Mountain Tea”

Twenty four phenolic compounds have been characterised in medicinal Sideritis species (aerial parts) from Macedonia by liquid chromatography–UV diode array coupled to ion-trap mass spectrometry with electrospray ionisation interface (negative mode).     

Antifungal activity and chemical composition of Citrus reticulata Blanco essential oil against phytopathogens from North East India

The essential oil (EO) isolated by hydro-distillation from the peel of fully matured ripen fruits of Citrus reticulata Blanco were analyzed by GC and GC-MS. Thirty seven different components were identified constituting approximately ≥99% of the oil. The major components were limonene (46.7%), geranial (19.0%), neral (14.5%), geranyl acetate (3.9%), geraniol (3.5%), β-caryophyllene (2.6%), nerol (2.3%), neryl acetate (1.1%) etc. The antifungal activity of the oil was tested by poisoned food (PF) technique and the volatile activity (VA) assay against five plant pathogenic fungi viz Alternaria alternata (Aa), Rhizoctonia solani (Rs), Curvularia lunata (Cl), Fusarium oxysporum (Fo) and Helminthosporium oryzae (Ho). The oil showed better activity in VA assay. The Minimum inhibitory concentration (MIC) for Aa, Rs and Cl was 0.2 ml/100 ml whereas >0.2 ml/100 ml for Fo and Ho in PF technique. Fungal sporulation was also completely inhibited at 2 ml/100 ml of the oil except for Cl and Ho, which was only 0.5% (±0.5) and 0.25% (±0.25) respectively as compared to control.     

Chemical and aroma profiles of yuzu (Citrus junos) peel oils of different cultivars

The essential oils of six different yuzu cultivars, Kumon (KUM), Nagano (NAG), Yasu (YAS), Jimoto (JIM), Komatsu Sadao (KOS) and Komatsu Koichi (KOK), were extracted by cold-pressing method. A total of 69 compounds of the six samples were identified. Application of GC-olfactometry and aroma extraction dilution analysis technique in three-fold stepwise dilution of the neat oil for all samples indicated eight odourants with the highest flavour dilution (FD) values. Those were limonene, α-pinene, α- and β-phellandrene, myrcene, γ-terpinene, (E)-β-farnesene and linalool. ‘KOS’ was differentiated from the other oil samples by showing the highest number of components having yuzu-like odour notes and also from the PCA analysis of the FD-factor values. This is the first time the aroma characteristics of yuzu essential oils of specified cultivars were investigated.     

Apoptosis-mediated proliferation inhibition of human colon cancer cells by volatile principles of Citrus aurantifolia

Fruits of Citrus aurantifolia were subjected to hydro-distillation using Clevenger type apparatus to obtain volatile oil. Chemical composition of volatile oil was analysed by GC–MS. Twenty-two compounds representing more than 89.5% of the volatile oil were identified. d-limonene (30.13%) and d-dihydrocarvone (30.47%) were found to be the major compounds in the lime volatile oil. This oil showed 78% inhibition of human colon cancer cells (SW-480) with 100 μg/ml concentration at 48 h. Lime volatile oil showed DNA fragmentation and induction of caspase-3 up to 1.8 and 2- folds after 24 h and 48 h, respectively, which may be due to the involvement of apoptosis. Analysis of apoptosis-related protein expression further confirmed apoptosis induction by lime volatile oil. The above results suggested that lime volatile oil has potential benefits in colon cancer prevention. This is the first report, showing the possible mechanism of antiproliferative effect of lime volatile oil for the prevention of colon cancer in cell culture models.     

Comparison of phenolic composition and antioxidant properties of two native Chilean and one domestic strawberry genotypes

The phenolic composition of extracts from the forms chiloensis and patagonica of Fragaria chiloensis were compared with that of the commercial strawberry Fragaria × ananassa cv. Chandler by high performance liquid chromatography with diode-array detector (HPLC–DAD) and high performance liquid chromatography with electrospray ionization mass spectroscopy detector (HPLC–ESI–MS). The phenolic constituents in the three species were mainly proanthocyanidins, hydrolysable tannins, anthocyanins and flavonol glycosides. In both native strawberry species the main flavonol glycoside was quercetin 3-O-glucuronide and the minor anthocyanins identified were cyanidin-malonyl-glucoside and pelargonidin-malonyl-glucoside. The highest anthocyanin content was found in the commercial red strawberry while ellagic acid was the main phenolic in the native white strawberry. From the methanolic fruit extract of the native Chilean strawberry Fragaria chiloensis ssp. chiloensis f. chiloensis four known antioxidants were isolated by selective fractionation using the bleaching of the free radical scavenger 1,1-diphenyl-2-picrylhydrazyl (DPPH) as the guiding assay. The antioxidant properties (measured as the bleaching of the DPPH radical) were determined for methanol extracts of the three fruits, for fractions of F. chiloensis ssp. chiloensis f. chiloensis, and for the isolated compounds cyanidin-3-glucoside, pelargonidin-3-glucoside, quercetin-3-glucuronide and ellagic acid. This study allows a clear chemical differentiation between the commercial strawberry and the Chilean white strawberry.     

Chemical and biological characteristics of Cuminum cyminum and Rosmarinus officinalis essential oils

Essential oils extracted by hydrodistillation from Cuminum cyminum and Rosmarinus officinalis were characterized by means of GC and GC–MS. C. cyminum and R. officinalis contained α-pinene (29.1%, 14.9%), 1,8-cineole (17.9%, 7.43%) and linalool (10.4%, 14.9%), respectively, as the major compounds. C. cyminum oil exhibited stronger antimicrobial activity than did R. officinalis oil against E. coli, S. aureus and L. monocytogenes. Complete death time on exposure to Cuminum cyminum L. and Rosmarinus officinalis L. oils were 20 and 25 min 180 and 240 min and 90 and 120 min for E. coli, S. aureus and L. monocytogenes, respectively. Radical-scavenging and antioxidant properties were tested by means of 1,1-diphenyl-2-picrylhydrazyl (DPPH) assay and the β-carotene bleaching test. These properties were compared to those of Thymus x-porlock essential oil, used as a reference ingredient. The radical scavenging performance of the rosemary oil was better than that of C. cyminum. Results from the antioxidant test were better than those provided by the radical-scavenging activity. C. cyminum and R. officinalis essential oils may be considered as potent agents in food preservation.     

Variation of glucosinolates in 62 varieties of Chinese cabbage (Brassica rapa L. ssp. pekinensis) and their antioxidant activity

Glucosinolate (GSL) and antioxidant activity in 62 varieties of Chinese cabbage (Brassica rapa L. ssp. pekinensis) were determined by HPLC and DPPH, HRSA, and FRAP assays. Five aliphatic GSLs: progoitrin, sinigrin, glucoalyssin, gluconapin, and glucobrassicanapin; four indolyl GSLs: 4-hydroxyglucobrassicin, glucobrassicin, 4-methoxyglucobrassicin, and neoglucobrassicin; one aromatic GSL: gluconasturtiin were identified. Glucobrassicanapin and gluconapin documented the most abundant (average 4.52 and 3.72 μmol/g DW, respectively). The contents of total GSLs varied extensively among 62 varieties (range from 2.83 to 48.53 μmol/g DW). Comprehensive differences in total and individual GSL contents have also been observed among different varieties. Indolyl and aromatic GSL together accounted 26% of the total GSLs; but there are few differences among varieties. FC7 and FI17 could be good candidates for future breeding programs since they had a high quantity of glucobrassicin (2.10 and 1.66 μmol/g DW, respectively). Most of the Chinese cabbage varieties showed significant antioxidant activities when compare with positive control. However, three antioxidant assays were not significantly correlated with total GSLs. The presence of significant quantities of glucobrassicin in some varieties should be studied more extensively, since GSL is the precursor of indole-3-carbinol, a potent anticancer isothiocyanate.     

Chemical composition and antioxidant and antimicrobial activity of two Satureja essential oils

Hydro-distilled volatile oils from the aerial parts of Satureja montana L., and Satureja subspicata Bartl. ex Vis., growing wild in Bosnia and Herzegovina, were analyzed by GC/MS. More than one hundred compounds were identified in both plant oils, representing 92.4–98.1% of the total oil. The major constituents of essential oils obtained from the plant material of S. montana, collected from two different localities, were thymol (31.7%), and geraniol (22.3%), respectively. The most abundant compounds in essential oils of S. subspicata, collected at two different stages of development, were thymol (28.6%), and spathulenol (37.6%), respectively. The screening of antimicrobial activity of essential oil samples was individually evaluated against Staphylococcus aureus, Staphylococcus epidermidis, Escherichia coli, Pseudomonas aeruginosa and Bacillus subtilis using a paper disc diffusion method. All tested microorganisms were inhibited by essential oil samples. Antioxidant activity was tested using the DPPH radical-scavenging method. All samples showed activity comparable to thymol, which was used as a positive probe.     

Antioxidant activity and phenolic composition of sumac (Rhus coriaria L.) extracts

Antioxidant activity and phenolic compounds of sumac extracts were investigated. Sumac was extracted in methanol and subjected to solvent–solvent partitioning to yield two fractions as ethyl acetate and aqueous. Methanol extract was further fractioned over Sephadex LH-20 column. Antioxidant activity of extracts and fractions were screened using ferric thiocyanate and DPPH radical scavenging methods. Phenolic composition of active fraction(s) was determined by HPLC–MS systems. Those fractions which exhibited strong antioxidant activity were rich in anthocyanins and hydrolysable tannins. While gallic acid was the main phenolic acid in the extracts, anthocyanin fraction contained cyanidin, peonidin, pelargonidin, petunidin, and delphinidin glucosides and coumarates. Pentagalloyl glucose was abundant in the hydrolysable tannin fraction. Effective scavenging concentration (EC₅₀) on DPPH radical was 0.70 μg/mL both in ethyl acetate and tannin fractions, and 5.33 μg/mL in anthocyanin rich fraction. Same extracts and fractions showed moderate lipid peroxidation inhibition effect compared with the synthetic antioxidants. The findings demonstrate that sumac can be used as a natural antioxidant.