Chemical Composition,Antibacterial, Antioxidant and in Vitro Antidiabetic Activities of Essential Oils from Eruca vesicaria

This work describes the study of the chemical composition and bioactivity of the essential oils (EOs) of the different organs (leaves, flowers, stems and roots) from Eruca vesicaria. According to the GC and GC/MS analysis, all the EOs were dominated by erucin (4‐methylthiobutyl isothiocyanate) with a percentage ranging from 17.9 % (leaves) to 98.5 % (roots). The isolated EOs were evaluated for their antioxidant (DPPH, ABTS and β‐carotene/linoleic acid), antibacterial and inhibitory property against α‐amylase and α‐glucosidase. Most EOs exhibited an interesting α‐glucosidase and α‐amylase inhibitory potential. The roots essential oil was found to be the most active with IC₅₀ values of 0.80±0.06 and 0.11±0.01 μg mL^?1, respectively. The essential oil of roots exhibited the highest antioxidant activity (DPPH, PI=92.76±0.01 %; ABTS, PI=78.87±0.19; and β‐carotene, PI=56.1±0.01 %). The isolated oils were also tested for their antibacterial activity against two Gram‐positive and three Gram‐negative bacteria. Moderate results have been noted by comparison with Gentamicin used as positive control.     

Polyphenol Characterization,Antioxidant and Skin Whitening Properties of Alnus cordata Stem Bark

In this study, we investigated the phenolic composition of the crude extract (MeOH 80 %) of Alnus cordata (Loisel .) Duby stem bark (ACE) and its antioxidant and skin whitening properties. RP‐LC‐DAD analysis showed a high content of hydroxycinnamic acids (47.64 %), flavanones (26.74 %) and diarylheptanoids (17.69 %). Furthermore, ACE exhibited a dose‐dependent antioxidant and free‐radical scavenging activity, expressed as half‐maximal inhibitory concentration (IC₅₀): Oxygen radical absorbance capacity (ORAC, IC₅₀ 1.78 μg mL^?1)>Trolox equivalent antioxidant capacity (TEAC, IC₅₀ 3.47 μg mL^?1)>2,2‐Diphenyl‐1‐picrylhydrazyl (DPPH, IC₅₀ 5.83 μg mL^?1)>β‐carotene bleaching (IC₅₀ 11.58 μg mL^?1)>Ferric reducing antioxidant power (FRAP, IC₅₀ 17.28 μg mL^?1). Moreover, ACE was able to inhibit in vitro tyrosinase activity (IC₅₀ 77.44 μg mL^?1), l ‐DOPA auto‐oxidation (IC₅₀ 39.58 μg mL^?1) and in an in vivo model it exhibited bleaching effects on the pigmentation of zebrafish embryos (72 h post fertilization) without affecting their development and survival. In conclusion, results show that A. cordata stem bark may be considered a potential source of agents for the treatment of skin disorders due to its bleaching properties and favorable safety profiles, associated to a good antioxidant power.     

Chemical Composition and Bioactivities of Essential Oil from Leaves of Syzygium cumini (L.) Skeels Native to Punjab,Pakistan

Herbal medicines are widely used for the treatment of different types of diseases like skin and throat infections and other diseases in developing countries. Syzygium cumini (L.) Skeels fruit, leaves and bark were used for the remedies of different diseases anciently. The aim of the present study was to evaluate the chemical profile of Syzygium cumini leaves essential oil (EO) from Punjab, Pakistan. The essential oil was isolated using hydrodistillation technique and analyzed by gas chromatography (GC) and gas chromatography‐mass spectrometry (GC/MS). Free radical scavenging capacity and antioxidant activity were assessed by using DPPH radical scavenging ability, inhibition of linoleic acid peroxidation, bleaching of β‐carotene in linoleic acid system and reducing power assays. Antimicrobial potential was assessed by disc diffusion assay and measurement of minimum inhibitory concentration (MIC) using resazurin microtiter‐plate assay. The anti‐heme biocrystallization activity of EO was also assessed. The major components (>3%) found in Syzygium cumini leaves EO were β‐farnesene (3.42 %), caryophyllenol (3.46 %), terpinen‐4‐ol (3.61 %), β‐myrcene (3.90 %), γ‐cadinene (4.09 %), fenchol (4.22 %), cis‐β‐ocimene (4.40 %) and 5‐methyl‐1,3,6‐heptatriene (4.90 %). Excellent antioxidant, antimicrobial and weak antimalarial potential was observed. It can be concluded that Syzygium cumini leaves EO has potential application for food and pharmaceutical industries.     

Antioxidant Activities of Aqueous Extract from Agrimonia pilosa Ledeb and Its Fractions

Agrimonia pilosa Ledeb is used as the tonic for asthenia and fatigue in China. Considering that the energizing effect might be correlated with antioxidant properties, we investigated the antioxidant activities of aqueous extract (AE) from Agrimonia pilosa Ledeb by assessing radical‐scavenging and anti‐lipid‐peroxidation abilities. We found that AE shows a moderate antioxidant activity to scavenge DPPH^., O , and ^.OH and inhibit β‐carotene bleaching with IC₅₀ values of 13.0, 33.2, 351, and 11.9 μg/ml, respectively, while its AcOEt‐soluble fraction (ESF) and BuOH soluble fraction (BSF) exhibit remarkable efficiencies. The ESF's IC₅₀ values of scavenging DPPH^., O , and ^.OH, and inhibiting β‐carotene bleaching are 5.6, 5.8, 171, and 7.6 μg/ml, respectively, and those of BSF are 7.5, 8.4, 82.0, and 6.2 μg/ml, respectively. In addition, we found that there is a significant correlation between total phenol content and the antioxidant activity determined by O and ^.OH scavenging, and β‐carotene‐bleaching assays. Furthermore, HPLC analysis revealed the presence of quercetin, hyperoside, quercitrin, taxifoliol, luteolin‐7‐O‐β‐D ‐glucopyranoside, and rutin in Agrimonia pilosa Ledeb . Thus, we suggest that the extracts from Agrimonia pilosa Ledeb , could be considered as natural antioxidant sources and dietary nutritional supplements to prevent oxidation‐related diseases.     

Chemical Composition,Antioxidant Properties, α‐Glucosidase Inhibitory,and Antimicrobial Activity of Essential Oils from Acacia mollissima and Acacia cyclops Cultivated in Tunisia

The genus Acacia is quite large and can be found in the warm subarid and arid parts, but little is known about its chemistry, especially the volatile parts. The volatile oils from fresh flowers of A. mollissima and A. cyclops (growing in Tunisia) obtained by hydrodistillation were analyzed by GC then GC/MS. Eighteen (94.7% of the total oil composition) and 23 (97.4%) compounds were identified in these oils, respectively. (E,E)‐α‐Farnesene (51.5%) and (E)‐cinnamyl alcohol (10.7%) constituted the major compounds of the flower oil of A. mollissima, while nonadecane (29.6%) and caryophyllene oxide (15.9%) were the main constituents of the essential oil of A. cyclops. Antioxidant activity of the isolated oils was studied by varied assays, i.e., 2,2‐diphenyl‐1‐picrylhydrazyl (DPPH) and 2,2‐azinobis 3‐ethylbenzothiazoline‐6‐sulfonic acid (ABTS); the isolated oils showed lowest IC₅₀ (4 – 39 μg/ml) indicating their high antioxidant activity. The α‐glucosidase inhibitor activity was also evaluated and Acacia oils were found to be able to strongly inhibit this enzyme with IC₅₀ values (81 – 89 μg/ml) very close to that of acarbose which was used as positive control. Furthermore, they were tested against five Gram‐positive and Gram‐negative bacteria and one Candida species. Essential oil of A. mollissima was found to be more active than that of A. cyclops, especially against Pseudomonas aeruginosa (MIC = 0.31 mg/ml and MBC = 0.62 mg/ml).     

Biological Activities of Triterpenoids and Phenolic Compounds from Myrica cerifera Bark

Seven triterpenoids, 1  –  7 , two diarylheptanoids, 8 and 9 , four phenolic compounds, 10  –  13 , and three other compounds, 14  –  16 , were isolated from the hexane and MeOH extracts of the bark of Myrica cerifera L. (Myricaceae). Among these compounds, betulin ( 1 ), ursolic acid ( 3 ), and myricanol ( 8 ) exhibited cytotoxic activities against HL60 (leukemia), A549 (lung), and SK‐BR‐3 (breast) human cancer cell lines (IC₅₀ 3.1 – 24.2 μm ). Compound 8 induced apoptotic cell death in HL60 cells (IC₅₀ 5.3 μm ) upon evaluation of the apoptosis‐inducing activity by flow cytometric analysis and by Hoechst 33342 staining method. Western blot analysis on HL60 cells revealed that 8 activated caspases‐3, ‐8, and ‐9 suggesting that 8 induced apoptosis via both mitochondrial and death receptor pathways in HL60. Upon evaluation of the melanogenesis‐inhibitory activity in B16 melanoma cells induced with α‐melanocyte‐stimulating hormone (α‐MSH), erythrodiol ( 7 ), 4‐hydroxy‐2‐methoxyphenyl β‐d ‐glucopyranoside ( 13 ), and butyl quinate ( 15 ) exhibited inhibitory effects (65.4 – 86.0% melanin content) with no, or almost no, toxicity to the cells (85.9 – 107.4% cell viability) at 100 μm concentration. In addition, 8 , myricanone ( 9 ), myricitrin ( 10 ), protocatechuic acid ( 11 ), and gallic acid ( 12 ) revealed potent DPPH radical‐scavenging activities (IC₅₀ 6.9 – 20.5 μm ).     

Chemical Compositions,Antioxidant and Antimicrobial Activities of Essential Oils of Psidium guajava L. Leaves from Different Geographic Regions in China

Hydrodistilled essential oils (EO) of Psidium guajava L. leaves from different regions in China were analyzed by GC and GC/MS. The samples from Guangdong Province displayed high EO yields (0.61 – 0.75%, v/w). A total of 50 components, representing over 98.00% of the EOs, were identified and semi‐quantitatived. The major constituents of EOs included β‐caryophyllene (17.17 – 31.38%), γ‐gurjunene (9.17 – 15.22%), τ‐cadinol (1.35 – 10.02%) and calamenene (2.13 – 7.80%). The terpenoids in all sample oils were dominated by sesquiterpenes hydrocarbons (70.18 – 84.35%), followed by oxygenated sesquiterpenes (9.89 – 22.19%). The similarities and differences among EOs from different samples were evaluated by hierarchical cluster analysis and principal component analysis methods. The IC₅₀ values of EOs from different regions were between 18.52 – 33.72 mg/ml (DPPH) and 13.12 – 25.15 mg/ml (ABTS⁺). The FRAP value of EO from Guangdong Province was 7.34 – 9.13 mmol Vc/g DM, while the FRAP value of EO from Taiwan Province was 2.29 – 2.36 mmol Vc/g DM. The antimicrobial tests revealed that EO had a higher antimicrobial activity against all Gram‐positive bacteria and two fungi. Moreover, EO from P. guajava leaves of Guangdong Province showed the highest antimicrobial activity. These properties can be considered in the design of industrial products and for further application in the food, pharmaceutical and cosmetic industries.     

UHPLC/HR‐ESI‐MS/MS Profiling of Phenolics from Tunisian Lycium arabicum Boiss. Antioxidant and Anti‐lipase Activities’ Evaluation

This study was performed in the aim to evaluate nine different extracts from Tunisian Lycium arabicum for their total phenolic and total flavonoid contents, phytochemical analyses as well as their antioxidant and anti‐lipase activities. The in vitro antioxidant property was investigated using three complementary methods (DPPH, ferric reducing antioxidant power (FRAP), and β‐carotene‐linoleic acid bleaching assays) while anti‐lipase activity was evaluated using 4‐methylumbelliferyl oleate method. From all of the tested extracts the most potent found to be the polar MeOH extracts especially those of stems and leaves. In order to investigate the chemical composition of these extracts and possible correlation of their constituents with the observed activities, an UHPLC/HR‐ESI‐MS/MS analysis was performed. Several compounds belonging to different chemical classes were tentatively identified such as rutin and kampferol rutinoside, the major constituents of the leaves, and N‐caffeoyltyramine, lyciumide A, N‐dihydrocaffeoyltyramine as well as fatty acids: trihydroxyoctadecadienoic acid and hydroxyoctadecadienoic acid isomers were detected abundantly in the stems. These results showed that the MeOH extracts of stems and leaves of L. arabicum can be considered as a potential source of biological active compounds.     

Chemical Composition and In Vitro Evaluation of Antimicrobial,Antioxidant and Antigerminative Properties of the Seed Oil from the Tunisian Endemic Ferula tunetana Pomel ex Batt.

Essential oil of the seeds from the endemic Tunisian plant Ferula tunetana Pomel ex Batt . was analyzed for its chemical composition and screened for its antimicrobial, antioxidant and antigerminative properties. The chemical composition of the isolated oil is reported for the first time. According to the GC/FID, GC/MS and ¹³C‐NMR analysis results; 18 compounds were identified accounting for 84.6% of the total oil. The chemical composition of this essential oil was characterized by the presence of a high proportion of monoterpene hydrocarbons (77.3%) followed by oxygenated sesquiterpenes (4.1%) and sesquiterpene hydrocarbons (3.2%). α‐Pinene (39.8%), β‐pinene (11.5%) and (Z)‐β‐ocimene (7.5%) were the predominant compounds. Moreover, the isolated oil was tested for its antimicrobial activity using the disc‐diffusion and the microdilution assays against six Gram‐positive and five Gram‐negative bacteria as well as towards two Candida species. The isolated oil was tested also for its antioxidant activity against DPPH, ABTS, and hydrogen peroxide (H₂O₂), and for its antigerminative potential. It was found that it exhibited interesting antimicrobial activity against Salmonella typhimurium LT2 DT104 (inhibition zone (IZ) 16.2 ± 1.0 mm) and Bacillus cereus ATCC 14579 (IZ 15.8 ± 1.0 mm). However, it exerted a moderate antioxidant activity against H₂O₂ (IC₅₀ 78.2 ± 2.98 μg/ml) and towards (IC₅₀ 89.2 ± 3.82 μg/ml). The antigerminative effect of this oil was also evaluated in this work. Results showed a toxic effect.     

Effects of β‐carotene on antioxidant status in rats with chronic alcohol consumption

This study examined the effects of β‐carotene on antioxidant status in rats with chronic alcohol consumption. At the beginning of experiment (week 0), according to both the plasma aspartate aminotransferase (AST) and alanine aminotransferase (ALT) activities, rats (n = 24) were divided into 3 groups and fed with a standard diet (group C), a diet containing ethanol (group E), or a diet containing ethanol and β‐carotene (group E+B). After 10 weeks, plasma AST and ALT, fat accumulation in the liver, antioxidant enzyme activities in erythrocytes and the liver, malondialdehyde (MDA), and α‐tocopherol and retinol in plasma and hepatic samples were analyzed. The chronic alcohol diet significantly increased AST and ALT levels in plasma, and these changes were prevented by supplementing the diet with β‐carotene. Glutathione (GSH) in erythrocytes and in the liver was significantly elevated in rats fed with a diet containing β‐carotene. The results indicate that β‐carotene supplementation can prevent ethanol‐induced liver damage and increase GSH concentrations in erythrocytes and the liver. Copyright © 2009 John Wiley & Sons, Ltd.     

Volatile‐Oils Composition,and Bioactivity of the Essential Oils of Plectranthus barbatus,P. neochilus,and P. ornatus Grown in Portugal

Volatile‐oils chemical composition and bioactivity of the essentail oils from Plectranthus barbatus, P. neochilus, and P. ornatus (Lamiaceae) were assessed. Aerial parts from these three related Plectranthus species were collected from cultivated plants grown in Portugal, during vegetative and flowering phases. Volatiles, isolated by distillation? extraction, were analyzed by GC and GC/MS. Monoterpene hydrocarbons (12–74%) and sesquiterpene hydrocarbons (4–45%) constituted the main fractions in all volatiles. α‐Pinene ( 3 ; 12–67%), oct‐1‐en‐3‐ol ( 6 ; traces–28%), β‐pinene ( 7 ; 0.1–22%), and β‐caryophyllene ( 50 ; 7–12%) dominated P. barbatus volatiles. P. neochilus major volatile components were α‐terpenyl acetate ( 41 ; traces–48%), α‐thujone ( 2 ; 2–28%), β‐caryophyllene ( 50 ; 2–28%), β‐pinene ( 7 ; 1–25%), and α‐pinene ( 3 ; 1–19%). Oct‐1‐en‐3‐ol ( 6 ; 13–31%), β‐pinene ( 7 ; 11–24%), α‐pinene ( 3 ; 11–19%), and β‐caryophyllene ( 50 ; traces–11%) were the main constituents from P. ornatus volatiles. These chemical compositions were rather different from those previously found for specimens harvested in Africa and Brazil. Moreover, the volatiles from the flowers are herewith reported for the first time. Essential oils, isolated by hydrodistillation from leaves and stems, showed a yellowish color and unpleasant odor, with yields ranging from 0.08% to 0.84% (v/dry weight). Antioxidant and antimicrobial activities of the essential oils were evaluated by DPPH^. and TBARS assays, and agar disc‐diffusion method, respectively. Results showed low or moderate antioxidant capacity and significant antimicrobial activity against Gram‐positive bacteria.     

Chemical Composition and Biological Activities of the Essential Oil of Athanasia brownii Hochr. (Asteraceae) Endemic to Madagascar

The essential oil obtained from hydrodistillation of flowering aerial parts of Athanasia brownii (Asteraceae) was studied for its chemical composition by GC/FID and GC/MS, and for biological activity, namely, antioxidant, antimicrobial, and chemopreventive potential, by DPPH (=2,2‐diphenyl‐1‐picrylhydrazyl), ABTS (=2,2′‐azinobis[3‐ethylbenzothioline‐6‐sulfonic acid), and FRAP (=ferric reducing antioxidant power), disk diffusion test, and MTT (=3‐(4,5‐dimethylthiazol‐2‐yl)‐2,5‐diphenyltetrazolium bromide) assay, respectively. The oil was characterized by a high content of oxygenated sesquiterpenes (71.2%), with selin‐11‐en‐4α‐ol (24.6%), caryophyllene oxide (8.7%), humulene epoxide II (5.1%), and (E)‐nerolidol (4.9%) as the predominant compounds. The oil showed a moderate activity against streptococci as well as radical‐scavenging potential, while the inhibitory effects against human cancer cells examined such as A375 (malignant melanoma) and HCT 116 (colon carcinoma) were significant, with IC₅₀ values of 19.85 and 29.53 μg/ml, respectively.     

Chemical Composition and Biological Studies of the Essential Oil from Aerial Parts of Beta vulgaris subsp. maritima (L.) Arcang. Growing in Tunisia

The chemical composition, antioxidant, cytotoxic, anticholinesterase and anti‐tyrosinase activities of the hydrodistilled essential oil of the aerial parts of Beta vulgaris subsp. maritime (L.) Arcang . from Tunisia have been evaluated. The chemical composition of the oil (yield 0.037% [w/w]), determined by GC‐FID and GC/MS is reported for the first time. Twenty five components, accounting for 98.1% of the total oil have been identified. The oil was characterized by a high proportion of oxygenated sesquiterpenes (39.2%), followed by sesquiterpene hydrocarbons (30.3%) and one apocarotenoids (26.3%). The main compounds were γ‐irone (26.3%), α‐cadinol (12.1%), T‐cadinol (10.6%), bicyclogermacrene (10.4%) and δ‐cadinene (6.0%). The isolated oil was tested for its antioxidant activity using the DPPH^·, ABTS^+·, catalase, and paraoxonase assays and also for its cytotoxic, anticholinesterase, and anti‐tyrosinase activities. The essential oil exhibited high antioxidant activity (IC₅₀ = 0.055 ± 0.006 mg/ml) and important result oncatalase (524.447 ± 2.58 Units/mg protein). Furthermore, it exerted a significant cytotoxic effect against A549 cell line, with IC₅₀ = 42.44 ± 1.40 μg/ml. The results indicate that the essential oil of B. vulgaris subsp. maritima (L.) Arcang . aerial parts may be used in future as an alternative to synthetic antioxidant agents, with potential application in the food and pharmaceutical industries.     

Oleanane‐type Saponins from Glochidion hirsutum and Their Cytotoxic Activities

Five new oleanane‐type saponins, hirsutosides A – E, were isolated from the leaves of Glochidion hirsutum (Roxb .) Voigt . Their structures were elucidated as 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐β‐d ‐glucopyranoside ( 1 ), 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐β‐d ‐glucopyranosyl‐(1 → 3)‐β‐d ‐glucopyranoside ( 2 ), 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐6‐acetyl‐[β‐d ‐glucopyranosyl‐(1 → 3)]‐β‐d ‐glucopyranoside ( 3 ), 21β‐benzoyloxy‐3β,16β,23,28‐tetrahydroxyolean‐12‐ene 3‐O‐β‐d ‐glucopyranosyl‐(1 → 3)‐〈‐l ‐arabinopyranoside ( 4 ), and 21β‐benzoyloxy‐3β,16β,23‐trihydroxyolean‐12‐ene‐28‐al 3‐O‐β‐d ‐glucopyranosyl‐(1 → 3)‐α‐l ‐arabinopyranoside ( 5 ). All isolated compounds were evaluated for cytotoxic activities on four human cancer cell lines, HepG‐2, A‐549, MCF‐7, and SW‐626 using the SRB assay. Compounds 1 , 2 , 4 , and 5 showed significant cytotoxic activities against all human cancer cell lines with IC₅₀ values ranging from 3.4 to 10.2 μm . Compound 3 containing acetyl group at glc C(6″) exhibited weak cytotoxic activity with IC₅₀ values ranging from 47.0 to 54.4 μm .     

Essential oil composition of Senecio graciliflorus DC: Comparative analysis of different parts and evaluation of antioxidant and cytotoxic activities

The essential oil of different parts of Senecio graciliflorus DC was obtained by hydrodistillation and analysed by GC-FID and GC–MS for the first time. A total of 17, 20, 19 and 17 constituents were identified comprising 99.90, 95.50, 98.93 and 95.96% of the essential oil of flower, leaf, stem and root parts of Senecio graciliflorus respectively. Monoterpene hydrocarbons predominated in the essential oil with 85.28% in flower, 57.53% in leaf, 67.74% in stem and 64.98% in root oil. α-pinene, cis-ocimene, 1,2,3-trimethylcyclohexane and β-pinene were the major constituents of the essential oil. The flower essential oil exhibited a strong antioxidant potential displaying IC₅₀ values of 21.6 ± 0.6 and 26.0 ± 1.0 μg/ml in DPPH and hydroxyl radical assays respectively. On the other hand the essential oil of flower and root displayed highest cytotoxicity against lung (A-549) cancer cell lines (IC₅₀ = 19.1 ± 0.9 and 21.3 ± 1.1 μg/ml respectively. This study which represents the first report of the essential oil composition and bioevaluation of Senecio graciliflorus, can serve as a new source of cytotoxic and antioxidant activity.     

Two New Anti‐Proliferative C18‐Norditerpenes from the Roots of Podocarpus macrophyllus

Activity‐guided fractionation strategy was used to investigate chemical constituents from the roots of Podocarpus macrophyllus. Successfully, two new norditerpenes, 2β‐hydroxymakilactone A ( 1 ) and 3β‐hydroxymakilactone A ( 2 ), along with ten known analogues ( 3  –  12 ) were isolated. The structures of 1 and 2 were elucidated by spectroscopic analysis including 1D‐, 2D‐NMR, and HR‐ESI‐MS data. The previously reported structure of 2,3‐dihydro‐2α‐hydroxypodolide was revised as 2,3‐dihydro‐2β‐hydroxypodolide ( 3 ) by spectroscopic analysis, and was further confirmed by X‐ray crystallographic analysis. Cytotoxic activities of all isolated compounds against five human solid tumour cell lines (AGS, HeLa, MDA‐MB‐231, HepG‐2, and PANC‐1) were evaluated. All of them exhibited anti‐proliferative activities (IC₅₀ = 0.3 – 27 μm ), except for 10 . Compounds 1 , 4 , 5 , 6 , and 8 exhibited potent inhibitory activities with IC₅₀ < 1 μm against HeLa and AGS cells.     

Chemical Composition and in vitro Biological Activities of Essential Oils from Conchocarpus fontanesianus (A. St.‐Hil.) Kallunki & Pirani (Rutaceae)

This study aimed at assessing the chemical composition of the essential oils from leaves and fruits of Conchocarpus fontanesianus, an endemic Brazilian species of Rutaceae. The plant material was harvested from two regions of the Atlantic rainforest in the State of São Paulo. The volatile compounds in the essential oils were extracted by hydrodistillation (HD), and analyzed by GC/FID and GC/MS, allowing the quantification and identification of 54 components in total, which comprise about 97% of the total oil composition. From the leaves collected in Caraguatatuba and Juréia‐Itatins, the major volatile compounds identified were as follows: spathulenol (22.32% and 16.67%) and α‐cadinol (9.7% and 14.76%). However, β‐myrcene (34.56%), (+)‐epi‐bicyclosesquiphellandrene (8.71%), and bicyclogermacrene (5.80%) were dominant in the fruits collected only in Juréia‐Itatins. The in vitro biological activities were tested to evaluate the cytotoxic, antifungal, and antioxidant potential of essential oils from leaves and fruits.     

Essential Oil Variability in Natural Populations of Artemisia campestris (L.) and Artemisia herba‐alba (Asso) and Incidence on Antiacetylcholinesterase and Antioxidant Activities

The intraspecific variability of Artemisia herba‐alba and A. campestris essential oils and the evaluation of their antioxidant and antiacetylcholinesterase activities were determined. Artemisia herba‐alba essential oil was found rich in camphor (19.61%), α‐thujone (19.40%), β‐thujone (9.44%), chrysanthenone (9.26%), and trans‐sabinyl acetate (8.43%). The major compounds of A. campestris essential oil were germacrene D (16.38%), β‐pinene (16.33%), and limonene (9.17%). Significant variation in the essential oil composition was observed among populations of each species. The divergence between populations was attributed to the variation of some climatic factors such as altitude, annual rainfall, winter cold stress, summer precipitation, summer drought stress, evapotranspiration, and humidity. Artemisia herba‐alba and A. campestris essential oils exhibited promising antioxidant and antiacetylcholinesterase activities. The level of activity varied significantly according to the species and the essential oil. The highest scavenging activity (IC₅₀ = 0.14 mg/ml) and the uppermost capacity to prevent β‐carotene bleaching (IC₅₀ = 0.10 mg/ml) characterized A. campestris from population 6. A. campestris population 3 possessed the uppermost ability to reduce ferric ions (450.7 μmol Fe²⁺/g EO). The population 2 of A. campestris showed the strongest antiacetylcholinesterase activity (IC₅₀ = 0.02 mg/ml). The variation of these activities between the essential oils was explained by their composition differences.     

Variability of Pinus halepensis Mill. Essential Oils and Their Antioxidant Activities Depending on the Stage of Growth During Vegetative Cycle

The impact of growth stages during vegetative cycle (B₀ – B₅) on chemical composition and antioxidant activities of Pinus halepensis Mill . needles essential oils was investigated for the first time. GC and GC/MS analyses pointed to a quantitative variability of components; terpene hydrocarbons derivatives, represented by α‐pinene (8.5 – 12.9%), myrcene (17.5 – 21.6%), p‐cymene (7.9 – 11.9%) and (Z)‐β‐caryophyllene (17.3 – 21.2%) as major components, decreased from 88.9% at B₀ growth stage to 66.9% at B₅ growth stage, whereas oxygenated derivatives, represented by caryophyllene oxide (5.4 – 12.6%) and terpinen‐4‐ol (0.4 – 3.3%) as major components, increased from 7% at B₀ growth stage to 28.4% at B₅ growth stage. Furthermore, our findings showed that essential oil of P. halepensis needles collected at B₅ growth stage possess higher antioxidant activities by four different testing systems than those collected at B₀ – B₄ growth stages. This highlighted variability led to conclude that we should select essential oils to be investigated carefully depending on growth stage, in order to have the highest effectiveness of essential oil in terms of biological activities for human health purposes.     

Comprehensive Characterisation of n‐Alkylresorcinols and Other Lipid Constituents of Mercurialis tomentosa L. from Alicante,Spain

Mercurialis tomentosa L. has been used in Spanish ethnomedicine. In the present study the first phytochemical characterisation of a lipid fraction from M. tomentosa was performed. The CHCl₃ extraction of aerial parts from M. tomentosa and GC/MS investigations revealed the occurrence of cuticular lipid and wax constituents, like long chain n‐alcohols and n‐aldehydes (C₂₂ – C₃₀), besides several aromatic constituents, i.e., phenylpropanoids and n‐alkylresorcinols. The latter were further purified by CC and analysed by LC/MSⁿ. In contrast to other Mercurialis species, i.e., M. annua, M. perennis, which exclusively contain 5‐n‐alkylresorcinols ( 1a  –  j , C_n), mainly 5‐n‐alkyl‐2‐methylresorcinols ( 2a  –  j , C_n*) with side chain lengths of C₁₅ – C₂₅ were found in M. tomentosa, in addition to 1a  –  j . Thus, the latter compounds may be utilised for analytical characterisation and authentication of M. tomentosa based on fingerprinting methods. For structure elucidation a novel facile total synthesis of one representative 5‐n‐alkyl‐2‐methylresorcinol homologue ( 2d , C₁₉*) was developed, starting with a Grignard reaction from a substituted benzoic acid chloride ( 19 ). The compound obtained by synthesis was identical to the natural product 2d in terms of its chromatographic and spectroscopic features. Futhermore, 2d exhibited satisfactory DPPH free radical scavenging activity (IC₅₀ = 37.8 μm ) when compared to trolox (IC₅₀ = 21.0 μm ), corroborating the antioxidant features of these amphipathic molecules.