A new fatty acid ester from an edible mushroom Rhizopogon luteolus

Phytochemical investigation of the Rhizopogon luteolus Fr. led to the isolation of one new fatty acid ester, 3-hydroxy-2,4-dimethylheptacosyl acetate (1) together with two known compounds tetracosanoic acid (2) and ergosterol (3). 1D and 2D NMR, and MS techniques were used for structural elucidation. Phenolic and fatty acid compositions were identified using HPLC–DAD and GC–MSD, respectively. Fumaric acid was the major phenolic acid, whereas linoleic, stearic and oleic acids were the most abundant fatty acids. Antioxidant and anticholinesterase activities of the extracts and compounds (1–3) were tested spectrophotometrically. Among the extracts, hexane extract showed the highest activity in all tests, particularly in β-carotene-linoleic acid assay (IC₅₀: 16.65 ± 1.12 μg/mL). Furthermore, compound 3 exhibited higher antioxidant and anticholinesterase activities. The study indicates that R. luteolus can be used in food, cosmetic and pharmaceutical industries.     

LC-ESI-MS/MS and cytotoxic activity of three Pistacia species

LC-ESI-MS/MS was used for a comprehensive characterisation of ethanol extract from the leaves of three Pistacia species. After optimisation of the method and the use of the negative ionisation mode, a total of 42 different compounds were identified, of which 22 were tentatively characterised in P. chinensis Bunge, 33 in P. khinjuk stocks and 25 in P. lentiscus L. leaves. Flavonoids, phenolic acids, and their derivatives were the most abundant identified compounds. LC-ESI-MS/MS revealed identification of 15, 18 and 6 not previously detected compounds in P. chinensis Bunge, P. khinjuk Stocks and P. lentiscus L., respectively. The three extracts were also tested for their cytotoxic activities against human PC3 prostate cancer, A549 lung cancer, MCF7 breast cancer and HepG2 liver cancer. Generally, all the extracts have a moderate cytotoxic activity against lung, breast and prostate cancer, with different IC₅₀. However, only P. lentiscus L. showed moderate activity against liver cancer.     

Profiling of Essential Oils from the Leaves of Pistacia lentiscus Collected in the Algerian Region of Tizi-Ouzou: Evidence of Chemical Variations Associated with Climatic Contrasts between Littoral and Mountain Samples

Leaves of Pistacia lentiscus were collected from two Algerian sites in the mountains and the littoral of the Tizi-Ouzou region. The harvest was conducted in four consecutive seasons on the same selected set of trees. Essential oils (EOs) were extracted by hydrodistillation; then, they were analyzed by gas chromatography coupled mass spectrometry (GC-MS). Forty-seven constituents could be detected and quantified, including α-pinene (2–13%), β-caryophyllene (8–25%), β-myrcene (0.3–19%), bornyl acetate (0.8–7%), δ-cadinene (3–8%), bisabolol (1–9%), β-pinene (0.9–7%), caryophyllene oxide (4–9%), and α-cadinol (3–11%). Antioxidant (AOx) activities of the EOs were assessed by ferric reducing antioxidant power (FRAP), 2,2-diphenyl-1-picrylhydrazyl (DPPH), and 2,2′-azino-bis (3-ethylbenzothiazoline)-6-sulfonic acid (ABTS) assays. Significant differences in EO composition and AOx activities appeared dependent on the season and the site. Variations of AOx activities were significant for the FRAP and ABTS tests but not for DPPH. Characterization of the leaf fatty acyl (FA) profiles was performed by GC-MS. Variability appeared according to season and altitude. Polyunsaturated fatty acids levels were high (27–55%) at the coldest date and place. The levels of linolenic acyl in the leaves were significantly correlated with bisabolol levels in the EOs (Spearman’s correlation coefficient: 0.818). Such results will be useful for the sustainable local valorization of wild P. lentiscus. These data also open new routes for further studies on terpenoid biosynthesis using correlation networks and fluxomic approaches.     

GC-MS analysis of penta- and tetra-cyclic triterpenes from resins of Pistacia species. Part II. Pistacia terebinthus var. Chia

Pistacia species contain oleoresins with bioactive triterpenes. In this study triterpenes, including minor components, were identified and quantified in both neutral and acidic fractions of Pistacia terebinthus var. Chia resin, grown exclusively in Chios island (Greece), collected traditionally, as well as using stimulating agents (liquid collection). It was proved that these two resin samples were composed of several different minor triterpenes, while major constituents were similar but in different proportions. Compounds that differentiated two resin samples of P. lentiscus and P. terebinthus var. Chia, both traditionally collected, were detected, in order to identify the nature of resins present in archaeological materials. In the traditionally collected resin, 37 triterpenes were identified, 12 in the acidic and 25 in the neutral fraction. In the liquid collection resin 10 compounds were identified in the acidic and 23 in the neutral fraction, while 16 compounds were not contained in the traditionally collected resin. The main triterpenes in both resin samples collected traditionally and using stimulating agents were: isomasticadienonic acid (23.6 and 26.3% w[sol ]w of the triterpenic fraction, respectively), 28-norolean-17-en-3-one (16.3 and 17.5% w[sol ]w of the triterpenic fraction, respectively) and masticadienonic acid (5.8 and 6.0% w[sol ]w of the triterpenic fraction). In this study the qualitative and quantitative composition of triterpenes was compared in the Pistacia lentiscus and P. terebinthus var. Chia resin samples collected with the traditional and new liquid techniques, and also triterpenes in resins of P. terebinthus obtained by the traditional technique and using stimulating agents. The aim of the study was also to examine whether the collection technique influenced the triterpenes contained in P. terebinthus var. Chia resin samples.     

In vitro antimicrobial activity of Pistacia lentiscus L. edible oil and phenolic extract

Pistacia lentiscus L. is known in some Tunisian forest area by its fixed oil used in traditional medicine as an antiseptic product. This investigation is the first to study the antimicrobial activity of P.lentiscus edible oil and its phenolic extract. Oil was extracted from fruits harvested from six provenances located in Tunisia. The antimicrobial activity was tested using disc diffusion assay and the broth dilution method. Kbouch and Sidi Zid oils were most efficient (p < 0.003) against, respectively, Staphylococcus aureus and Aspergillus niger with an inhibition zone of 9.33 mm. The phenolic extract had the largest spectrum of sensitive microorganisms. The minimum inhibitory concentration and minimum bactericidal concentration results showed that all strains were inhibited by both oil and extract.     

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.     

Pistacia atlantica leaf extract mediated synthesis of silver nanoparticles and their antioxidant,cytotoxicity, and antibacterial effects under in vitro condition

Recently, researchers have investigated the therapeutical properties of metal nanoparticles especially silver nanoparticles in vitro and in vivo conditions. The aim of the experiment was green synthesis and chemical characterization of silver nanoparticles from aqueous extract of Pistacia atlantica leaf (Ag NPs) and evaluation of their cytotoxicity, antioxidant, and antibacterial effects under in vitro condition. Ag NPs were spherical with a size range of 40-60 nm and characterized using various analysis techniques including UV–Vis absorption spectroscopy to determine the presence of Ag NP in the solution. We studied functional groups of Pistacia atlantica extract in the reduction and capping process of Ag NP by FT-IR, crystallinity and FCC planes by XRD pattern, elemental analysis of the sample by EDS, and surface morphology, shapes, and size of Ag NPs by SEM, AFM, and TEM. Destroy initiation and termination temperatures of the Ag NPs were determined by TGA. DPPH free radical scavenging test was done to evaluate the antioxidant potentials, which indicated similar antioxidant potentials for Ag NPs and butylated hydroxytoluene. The synthesized Ag NPs had great cell viability dose-dependently and indicated this method was nontoxic. Agar diffusion tests were done to determine the antibacterial characteristic. Ag NPs revealed similar antibacterial property to the standard antibiotic. Also, Ag NPs prevented the growth of all bacteria at 1-7 μg/ml concentrations and removed them at 3-15 μg/ml concentrations. Finally, synthesized Ag NPs revealed non-cytotoxicity, antioxidant and antibacterial activities in a dose-depended manner.     

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.     

Syntheses and biological evaluation of phosphoryl-containing polyunsaturated fatty acid derivatives as hypolipidemic agents

A series of novel compounds phosphoryl-containing polyunsaturated fatty acid derivatives n-(diisopropoxy-phosphonamide)-alkyl ester (2a–2o) have been synthesized and evaluated for lowering hypolipidemia activities. Amongst all the synthesized compounds, compound 2d, 2h, and 2m showed significant lowering of triglyceride (TG) by 47.37%, 45.88%, and 45.69%, respectively, in triton induced hyperlipidemic in mice. Furthermore, compound 2d showed potent antihyperlipidemic activity and was found to decrease the plasma total cholesterol levels (TC) by 53.3%, TG by 29.3%, in high-fat diet induced hyperlipidemic in mice.     

Untargeted fatty acid profiles based on the selected ion monitoring mode

Fatty acids are potential biomarkers of some diseases and also key markers and quality parameters of different dietary fats and related products. Thus, untargeted fatty acid profiles are important in the study of dietary fat quality and fat-related diseases, as well as in other fields such as bioenergy. In addition, accurate identification of unknown components is a technological breakthrough for the selected ion monitoring (SIM) mode for untargeted profiles. In this study, we developed untargeted fatty acid profiles based on SIM. We also investigated mass spectral characteristics and equivalent chain lengths (ECL) to eliminate the influence of non-FAMEs for identifying fatty acids in samples. As an application example, fatty acid profiles were used to classify three edible vegetable oils. The results indicated that SIM-based untargeted fatty acid profiles could yield accurate qualitative and quantitative results for more fatty acids and benefit related studies of metabolite profiles.     

Serum fatty acid profiles and potential biomarkers of ankylosing spondylitis determined by gas chromatography–mass spectrometry and multivariate statistical analysis

Ankylosing spondylitis (AS) is a common chronic inflammatory rheumatic disease. Early and accurate detection is essential for effective disease treatment. Recently, research has focused on genomics and proteomics. However, the associated metabolic variations, especially fatty acid profiles, have been poorly discussed. In this study, the gas chromatography–mass spectrometry (GC‐MS) approach and multivariate statistical analysis were used to investigate the metabolic profiles of serum free fatty acids (FFAs) and esterified fatty acids (EFAs) in AS patients. The results showed that significant differences in most of the FFA (C12:0, C16:0, C16:1, C18:3, C20:4, C20:5, C22:5 and C22:6) and EFA (C12:0, C16:1, C18:0, C18:1, C18:2, C18:3, C20:4 and C22:6) concentrations were found between the AS patients and healthy controls (p < 0.05). Principal component analysis and partial least squares discriminant analysis were performed to classify the AS patients and controls. Additionally, FFAs C20:4, C12:0, C18:3 and EFAs C22:6, C12:0 were confirmed as potential biomarkers to identify AS patients and healthy controls. The present study highlights that differences in the serum FFA and EFA profiles of AS patients reflect the metabolic disorder. Moreover, FFA and EFA biomarkers appear to have clinical applications for the screening and diagnosis of AS. Copyright © 2014 John Wiley & Sons, Ltd.     

New fatty acid,aromatic ester and monoterpenic benzyl glucoside from the fruits of Withania coagulans Dunal

The fruits of Withania coagulans Dunal (family: Solanaceae) are sweet, sedative, emetic, alterative and diuretic; used to treat asthma, biliousness, strangury, wounds, dyspepsia, flatulent colic, liver complaints and intestinal infections in the indigenous system of medicine. Phytochemical investigation of the methanolic extract of W. coagulans fruits led to the isolation of a new fatty acid, an aromatic ester and a monoterpenic benzyl glucoside characterised as n-octatriacont-17-enoic acid (3), geranilan-10-olyl dihydrocinnamoate (4) and geranilan-8-oic acid-10-olyl salicyloxy-2-O-β-d-glucofuranosyl-(6″→1?)-O-β-d-glucofuranosyl-6?-n-octadec-9?′,11?′-dienoate (5) along with two known fatty acids, n-dotriacont-21-enoic acid (1) and n-tetratriacontanoic acid (2). The structures of isolated phytoconstituents were established on the basis of 1D and 2D NMR, FT-IR, UV, and MS data and chemical means.     

Synthesis,antioxidant, and anticholinesterase activities of novel N-arylsulfonyl hydrazones bearing sulfonate ester scaffold

In this research, two new series of N-arylsulfonyl hydrazone compounds ( 14 – 25 ) possessing a sulfonate moiety were synthesized and characterized by elemental analysis and various spectroscopic techniques including fourier transform infrared (FT-IR), ¹H-, and ¹³C nuclear magnetic resonance (NMR). These compounds synthesized as target molecules ( 14 – 25 ) were tested for their in vitro acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibition activities and antioxidant potential. The antioxidant capacities of the tested molecules were determined by four different assays. The IC₅₀ values of the screened molecules were determined in the range of 60.14 ± 0.25–84.81 ± 1.09 μM against AChE and in the range of 70.11 ± 0.67–93.60 ± 0.47 μM against BChE. In the AChE assay, 4-hydroxybenzaldehyde-based compound 25 (60.14 ± 0.25 μM) showed the highest activity in comparison to rivastigmine (501 ± 3.08 μM). This compound (71.42 ± 0.19 μM) is also one of the compounds with the highest activity against BChE. In the BChE assay, 2-hydroxybenzaldehyde-based compound 19 (70.11 ± 0.67 μM) indicated the highest activity in comparison to rivastigmine (19.95 ± 0.20 μM). In antioxidant activity studies, the tested molecules showed lower activities than the standard compounds (butylated hydroxytoluene and α-tocopherol). Consequently, some novel compounds can be used as potential inhibitor candidates in future studies.     

The influence of serum fatty acid binding proteins on arachidonic acid uptake by macrophages

The role of serum fatty acid binding proteins (FABPs) in arachidonic acid (AA) uptake by murine peritoneal macrophages has been studied. The kinetics of [³H]arachidonic acid uptake by the cells was investigated over a wide range of AA concentration (10⁻¹⁰–10⁻⁵ M). It was shown that these putative fatty acid transporters dramatically change the uptake processes. In the presence of FABPs, the time-course curves of AA uptake exhibited two distinct periods: one with a rapid AA uptake during the first hour with an equilibrium in 1–2.5 h and another with an equilibrium reached in 20 h, whereas in the absence of FABPs the uptake curves were smooth without kinks and with the equilibrium reached in 10 h. In addition, it was shown that the amount of incorporated AA was linearly dependent on the concentration of AA over the range of 10⁻¹⁰–10⁻⁶ M in the presence of serum FABPs and 10⁻¹⁰–10⁻⁷ M in their absence. We assume that the changes in the character of AA uptake by macrophages in the presence of FABP soccur due to the interaction of FABPs with the cell plasma membrane.     

脂肪酸在超临界甲醇中的酯化反应研究

超临界甲醇中的酯化和酯交换反应是利用植物油、动物油或废油脂制备生物柴油的新工艺.它的最大特点是不需要添加催化剂,超临界甲醇既是反应媒介,又是反应物.     

Trapping of fatty acid allyl radicals generated in lipoxygenase reactions in biological fluids by nitroxyl radical

Nitroxyl radicals can trap fatty acid allyl radicals on ferric‐lipoxygenases at lower oxygen content, which are an intermediate in the lipoxygenase reaction. In the present study, we examined whether nitroxyl radical‐trapping of fatty acid allyl radicals on the enzyme proceeds in biological fluids with abundant antioxidants. The fatty acid allyl radical–nitroxyl radical adducts were quantified by HPLC with electrochemical detection (HPLC‐ECD); the adducts in eluate degraded into nitroxyl radical by passing through heating coil at 100°C, and then nitroxyl radical was detected by electrochemical detector. Soybean 15‐lipoxygenase and nitroxyl radical (3‐carbamoyl‐2,2,5,5‐tetramethyl‐3‐pyrroline‐N‐oxyl, CmΔP) were mixed with rat serum prepared from fresh venous blood, and the solution was stood at 37°C for 1 h. One volume of the solution was mixed with 5 vols of cold acetonitrile. After centrifugation, the supernatant was subjected to HPLC‐ECD. Arachidonate allyl radical–CmΔP adducts as well as linoleate allyl radical–CmΔP adducts were detected in the solution, and the content of these adducts remarkably increased in the presence of phospholipase A₂. It is proved for the first time that nitroxyl radical traps fatty acid allyl radicals generated in the lipoxygenase reaction in biological fluid without competition from endogenous antioxidants. Copyright © 2010 John Wiley & Sons, Ltd.     

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.     

Review of the biological properties and toxicity of usnic acid

Since its first isolation in 1844, usnic acid [2,6-diacetyl-7,9-dihydroxy-8,9b-dimethyl-1,3(2H,9bH)-dibenzo-furandione] has become the most extensively studied lichen metabolite and one of the few that are commercially available. Lichens belonging to usnic acid-containing genera have been used as crude drugs throughout the world. There are indications of usnic acid being a potentially interesting candidate for such activities as anti-inflammatory, analgesic, healing, antioxidant, antimicrobial, antiprotozoal, antiviral, larvicidal and UV protection. However, some studies reported the liver toxicity and contact allergy. Thus, further studies are needed to establish the efficacy and safety of usnic acid     

基于血浆中脂肪酸代谢谱及非线性判别分析方法的糖尿病中医证候分型

糖尿病是严重威胁人类健康的代谢综合征之一,中医因在治疗糖尿病方面有着自身的优势和特色而广泛受到重视。该文以血浆中脂肪酸代谢谱及血脂代谢指标为研究对象,结合化学计量学方法,对5种糖尿病中医证候(气虚、阴虚、气阴两虚、热盛和血瘀)进行关联分析。通过正交信号校正的偏最小二乘(OSC-PLS)方法将5种证候与健康组较明显地区分开。同时,采用非线性判别分析(ULDA)对健康组、中医虚证(气虚、阴虚、气阴两虚)、中医实证(热盛、血瘀)进行分析,3组样本体现明显的聚类效果,正判率达到95.7%。其中对分类贡献较大的标志物为二十碳二烯酸(C20:2)、二十碳五烯酸(C20:5)、甘油三酯(TG)和高密度脂蛋白(HDL),这一结果为辅助糖尿病中医临床诊断提供了重要的信息。     

Fatty acid composition and tocopherol profiles of safflower (Carthamus tinctorius L.) seed oils

The oil contents of safflower seeds ranged from 23.08% to 36.51%. The major fatty acid of safflower oil is linoleic acid, which accounted for 55.1–77.0% in oils, with a mean value of 70.66%. Three types of tocopherols were found in safflower oil in various amount α-tocopherol, β-tocopherol and γ-tocopherol, ranged from 46.05 to 70.93 mg/100 g, 0.85 to 2.16 mg/100 g and trace amount to 0.45 mg/100 g oils, respectively. This research shows that both fatty acid and tocopherol contents differ significantly among the safflowers.