Biflavonoids from Caper (Capparis spinosa L.) fruits and their effects in inhibiting NF-kappa B activation

Caper (Capparis spinosa L.) fruits have been widely used as food and folk medicine in the Mediterranean basin and in central and west Asia. In this study, two biflavonoids, isoginkgetin, and ginkgetin, together with three other flavonoids, were isolated from caper fruits. Their chemical structures were elucidated by spectroscopic analyses and comparison with literature. To our knowledge, isoginkgetin, ginkgetin and sakuranetin were identified in caper for the first time. Notably, it is also the first time that biflavonoids have ever been found in the Capparidaceae. Concentrations of the two biflavonoids were measured in caper fruits collected from four major growing areas in northwest China. The anti-inflammatory effects of the flavonoids from caper fruits were evaluated by secreted placental alkaline phosphatase (SEAP) reporter assay, which was designed to measure nuclear factor-kappa B (NF-κB) activation. Isoginkgetin and ginkgetin showed inhibitory effects in initial screen at 20 μM, while the effect of ginkgetin was much greater than that of isoginkgetin. In a dose-response experiment, the IC(50) value of ginkgetin was estimated at 7.5 μM, suggesting it could be a strong NF-κB inhibitor and worthy of study in vivo.     

Fatty acid profiles, tocopherol contents, and antioxidant activities of heartnut (Juglans ailanthifolia Var. cordiformis) and Persian walnut (Juglans regia L.)

The fatty acid and tocopherol compositions of three heartnut (Juglans ailanthifolia var. cordiformis) varieties (Imshu, Campbell CW1, and Campbell CW3) were examined and compared with those of two Persian walnut (Juglans regia L.) varieties (Combe and Lake). The major fatty acids found in heartnuts and walnuts were identified by gas chromatography as linoleic (18:2n-6), alpha-linolenic (18:3n-3), oleic (18:1n-9), palmitic (16:0), and stearic acid (18:0). Polyunsaturated fatty acids were the main group of fatty acids found in both heartnut and walnut, ranging from 73.07 to 80.98%, and were significantly higher in heartnut than in Persian walnuts (P < 0.001). In addition, heartnuts had significantly higher levels of 18:2n-6 and lower levels of 18:3n-3 compared to the Persian walnuts. gamma-Tocopherol was the main tocopherol homologue present in both types of nuts, followed by delta- and alpha-tocopherol. The highest concentration of gamma-tocopherol was found in Combe Persian walnut at 267.87 mug/g, followed by Lake Persian walnut and Imshu, Campbell CW1, and CW3 heartnut at 205.45, 187.33, 161.84, and 126.46 mug/g, respectively. Tocopherols, particularly the gamma-tocopherol, were found to contribute the most to the strong total antioxidant activities of both walnut and heartnut oils using either the free radical 2,2-diphenyl-1-picrylhydrazyl assay or the photochemiluminescence method.     

Bioactive components of caper (Capparis spinosa L.) from Sicily and antioxidant effects in a red meat simulated gastric digestion

An increasing body of evidence on the association between adherence to the Mediterranean diet and healthy status is being accumulated. Floral buds of Capparis spinosa L. are commonly used in the Mediterranean cuisine as flavoring for meat and other foods. The present study evaluated bioactive components and antioxidant activity of Sicilian capers stabilized in salt. Whereas alpha-tocopherol was absent, low levels of gamma-tocopherol and vitamin C were measured. With reference to one serving size (8.6 g of capers), rutin was 13.76 mg, isothiocyanates, recently acknowledged as anticarcinogen phytochemicals, were 42.14 micromol, total phenols were 4.19 mg of gallic acid equivalents (GAE), and the total antioxidant potential measured using the [2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonic acid)] diammonium salt (ABTS) cation radical decolorization assay was 25.8 micromol of Trolox equivalents. The antioxidative activity of a caper hydrophilic extract was assessed in a number of assays. The extract at 3.5 and 7.0 microM GAE exhibited a dose-dependent peroxyl radical scavenging activity in a methyl linoleate methanol solution oxidized by azo initiator, and reduced hypervalent iron myoglobin species formed from met-Mb an H 2O 2, at 180 microM GAE. The hydrophilic extract, at 70-280 microM GAE, caused a dose-dependent inhibition of lipid autoxidation in heated red meat, incubated with simulated gastric fluid for 180 min. In the same model rutin tested at a concentration corresponding to its content in the extract was ineffective, and alpha-tocopherol at 25 microM was poorly effective. The hydrophilic extract (70 microM GAE) prevented the consumption of the co-incubated alpha-tocopherol, whereas lipid oxidation was inhibited for the experimental time, suggesting cooperative interactions between extract components and the vitamin. The findings encourage the use of caper with foods that contribute oxidizable lipids in view of the association between dietary oxidized lipids and risk of oxidative stress-based diseases.     

Anti-inflammatory effects of caper (Capparis spinosa L.) fruit aqueous extract and the isolation of main phytochemicals

Caper (Capparis spinosa L.) fruits have been used as food as well as folk medicine in the treatment of inflammatory disorders, such as rheumatism. The present study was carried out to study the anti-inflammatory activities of C. spinosa L. fruit (CSF) aqueous extract and to isolate main phytochemicals from its bioactive fractions. The CSF aqueous extract were separated into three fractions (CSF1-CSF3) by macroporous adsorption resins. The fractions CSF2 and CSF3 effectively inhibited the carrageenan-induced paw edema in mice. Systematic fractionation and isolation from CSF2+3 led to the identification of 13 compounds (1-13). Their chemical structures were elucidated by spectroscopic analyses including nuclear magnetic resonance (NMR) and mass spectrometry (MS) and literature comparisons. Major compounds found in the bioactive fraction CSF2+3 are flavonoids, indoles, and phenolic acids. To our knowledge, 8 of these 13 compounds (1-4, 6-7, 10, and 13) were identified from caper fruits for the first time. The anti-inflammatory effects of these purified compounds are currently under investigation.     

Evaluation of extracts and isolated fraction from Capparis spinosa L. buds as an antioxidant source

The antioxidant activity of extracts from Capparis spinosa L. buds was evaluated using different in vitro tests: ascorbate/Fe(2+)-mediated lipid peroxidation of microsomes from rat liver; bleaching of 1,1-diphenyl-2-picryl-hydrazyl radical; and autoxidation of Fe(2+) ion in the presence of bathophenanthroline disulfonate. The methanolic extract showed strong activities in all of these in vitro tests. The amount of total phenols was determined in the methanolic extract. In addition, the level of rutin was calculated as 0.39% (w/w) by HPLC analysis. Our findings indicate the following: (a) the antioxidant efficiency of the methanolic extract may be attributed to its phenolic content; and (b) the antioxidant activity of the methanolic extract was maintained after removal of glucosinolates, confirming that these compounds do not interfere with the antioxidant properties of the extract. The results obtained from this study exalt the nutritional value of the flowering buds (capers) which are widely used as a source of flavor.     

Fatty acid composition and antioxidant properties of cold-pressed marionberry, boysenberry, red raspberry, and blueberry seed oils

Cold-pressed marionberry, boysenberry, red raspberry, and blueberry seed oils were evaluated for their fatty acid composition, carotenoid content, tocopherol profile, total phenolic content (TPC), oxidative stability index (OSI), peroxide value, and antioxidant properties. All tested seed oils contained significant levels of alpha-linolenic acid ranging from 19.6 to 32.4 g per 100 g of oil, along with a low ratio of n-6/n-3 fatty acids (1.64-3.99). The total carotenoid content ranged from 12.5 to 30.0 micromoles per kg oil. Zeaxanthin was the major carotenoid compound in all tested berry seed oils, along with beta-carotene, lutein, and cryptoxanthin. Total tocopherol was 260.6-2276.9 mumoles per kg oil, including alpha-, gamma-, and delta-tocopherols. OSI values were 20.07, 20.30, and 44.76 h for the marionberry, red raspberry, and boysenberry seed oils, respectively. The highest TPC of 2.0 mg gallic acid equivalents per gram of oil was observed in the red raspberry seed oil, while the strongest oxygen radical absorbance capacity was in boysenberry seed oil extract (77.9 micromol trolox equivalents per g oil). All tested berry seed oils directly reacted with and quenched DPPH radicals in a dose- and time-dependent manner. These data suggest that the cold-pressed berry seed oils may serve as potential dietary sources of tocopherols, carotenoids, and natural antioxidants.     

Influence of harvest date and crop yield on the fatty acid composition of virgin olive oils from cv. Picual

In this study was analyzed the effect of crop year and harvesting time on the fatty acid composition of cv. Picual virgin olive oil. The study was carried out during the fruit ripening period for three crop seasons. The mean fatty acid composition of Picual oils was determined. The oils contained palmitic acid (11.9%), oleic acid (79.3%), and linoleic acid (2.95%). The content of palmitic acid and saturated fatty acids decreased during fruit ripening while oleic and linoleic acids increased. The amount of stearic and linolenic acids decreased. The amount of saturated acids, palmitic and stearic, and the polyunsaturated acids linoleic and linolenic was dependent on the time of harvest, whereas the amount of oleic acid varied with the crop year. The differences observed between crop years for both palmitic and linoleic acid may be explained by the differences in the temperature during oil biosynthesis and by the amount of summer rainfall for oleic acid content. A significant relationship was observed between the MUFA/PUFA ratio and the oxidative stability measured by the Rancimat method.     

Dose and duration effect of alpha-tocopheryl acetate supplementation on chicken meat fatty acid composition, tocopherol content, and oxidative status

The effects of dietary alpha-tocopheryl acetate (alpha-TA) doses (75, 150, and 225 mg/kg) and the duration of this supplementation (0, 10, 21, 32, and 43 days prior to slaughter) on fatty acid composition, alpha-tocopherol content, and oxidative status were studied either in raw or in cooked dark chicken meat with its skin. With regard to fatty acid composition, raw meat was affected by both dietary factors. Various polyunsaturated fatty acids decreased as a result of higher alpha-TA doses, whereas these fatty acids increased with longer supplementation periods. Cooked meat showed similar trends for the duration of alpha-TA supplementation. On the other hand, alpha-tocopherol content in raw and cooked meat increased as a result of the dose and duration of alpha-TA supplementation. Formation of lipid hydroperoxides and thiobarbituric acid values of these meats were also influenced by these two dietary factors, and the dietary combination of 150 mg/kg of alpha-TA during the last 32 days was optimal in terms of supplementation costs and meat oxidative stability.     

Characteristics and composition of watermelon, pumpkin, and paprika seed oils and flours

The nutritional quality and functional properties of paprika seed flour and seed kernel flours of pumpkin and watermelon were studied, as were the characteristics and structure of their seed oils. Paprika seed and seed kernels of pumpkin and watermelon were rich in oil and protein. All flour samples contained considerable amounts of P, K, Mg, Mn, and Ca. Paprika seed flour was superior to watermelon and pumpkin seed kernel flours in content of lysine and total essential amino acids. Oil samples had high amounts of unsaturated fatty acids with linoleic and oleic acids as the major acids. All oil samples fractionated into seven classes including triglycerides as a major lipid class. Data obtained for the oils' characteristics compare well with those of other edible oils. Antinutritional compounds such as stachyose, raffinose, verbascose, trypsin inhibitor, phytic acid, and tannins were detected in all flours. Pumpkin seed kernel flour had higher values of chemical score, essential amino acid index, and in vitro protein digestibility than the other flours examined. The first limiting amino acid was lysine for both watermelon and pumpkin seed kernel flours, but it was leucine in paprika seed flour. Protein solubility index, water and fat absorption capacities, emulsification properties, and foam stability were excellent in watermelon and pumpkin seed kernel flours and fairly good in paprika seed flour. Flour samples could be potentially added to food systems such as bakery products and ground meat formulations not only as a nutrient supplement but also as a functional agent in these formulations.     

Acylglycerol and fatty acid components of pulp,seed, and whole olive fruit oils. Their use to characterize fruit variety by chemometrics

The contents of triacylglycerols and diacylglycerols in three kinds of olive fruit oils (pulp, seed, and whole fruit) were determined. The fatty acid composition and the quality ratios 1,2-diacylglycerols/1,3-diacylglycerols and 1,2-diacylglycerols/total diacylglycerols were also assessed. Seven major Italian olive varieties were considered. Results of univariate statistical analyses indicated that the above analytical parameters (glyceridic ratios excepted) were effective in discriminating between pulp and seed oils. The seed oil fraction did not determine any change in the glyceridic indices and the acylglycerol or fatty acid composition concerning the whole fruit oil (mixture of pulp and seed oil fractions), the weight (%) of seed ( approximately 2%) being by far lower than the weight (%) of pulp ( approximately 85%) (fruit weight basis). Based on the data of triacylglycerol or fatty acid composition, and using appropriate parametric or nonparametric multivariate statistics, the genetic origins (olive variety) of the three fruit oil kinds were characterized.     

黑莓籽油的超临界萃取及脂肪酸成分分析

为了获得高品质保健油脂,采用超临界CO2萃取黑莓籽油,以气相色谱-质谱（GC-MS）对黑莓籽油脂肪酸成分进行分析。样品最佳粉碎粒度60目,超临界CO2萃取适宜工艺条件为：萃取压力20 MPa,分离罐压力10 MPa,萃取罐温度45℃,萃取时间30 min,萃取得率为(17.73±0.19)%。GC-MS检测结果显示黑莓籽油中含有丰富的不饱和脂肪酸,尤其是亚油酸、油酸、亚麻酸,质量分数分别为58.04%、11.76%、8.38%,占总脂肪酸的78.18%。研究结果为黑莓籽的综合开发加工利用提供了参考。     

Phenolic composition and antioxidant activity of aqueous infusions from Capparis spinosa L. and Crithmum maritimum L. before and after submission to a two-step in vitro digestion model

This study investigated the phenolic composition and antioxidant activities of aqueous infusions from wild-grown caper (Capparis spinosa L.) and sea fennel (Crithmum maritimum L.) from the Dalmatia region (Croatia) before and after their submission to an in vitro digestion process. HPLC/UV-vis-DAD/ESI-MS analysis of the caper infusion identified rutin, kaempferol 3-O-rutinoside, and isorhamnetin 3-O-rutinoside as dominant flavonoids in the matrix together with a series of cinnamoylquinic acid derivatives, whereas in the sea fennel aqueous infusion chlorogenic acid (5-caffeoylquinic acid), its isomers, and higher derivatives were identified as almost the sole class of phenolics. Both infusions exhibited good and dose-dependent antioxidant activity before in vitro digestion by the DPPH method, the β-carotene bleaching method, and copper-induced oxidation of human LDL. The amount of total phenolics (Folin-Ciocalteu assay) strongly decreased in digested samples (from 3.0 and 2.2% in caper and sea fennel infusions, respectively, to <1.0%), as did their antioxidant activity as measured by the three aforesaid methods. The results showed that the majority of phenolic compounds detected in both infusions are not stable under applied simulated gastrointestinal conditions and that the stability of these secondary metabolites strongly depends on the nature of the corresponding matrix.     

Determination of sterol and fatty acid compositions, oxidative stability, and nutritional value of six walnut (Juglans regia L.) cultivars grown in Portugal

Six cultivars (Franquette, Marbot, Mayette, Mellanaise, Lara, and Parisienne) of walnuts (Juglans regia L.) were collected during the 2001 crop, from Bragan?a, Portugal. Chemical composition, including moisture, total oil content, crude protein, ash, carbohydrates, and nutritional value, was evaluated. Fat was the predominant component, ranging from 62.3 to 66.5%. Total oil was extracted and analyzed for fatty acids, sterols, oxidative stability, and peroxide value. Fatty acids and sterols were determined by gas-liquid chromatography coupled to a flame ionization detector. Eighteen fatty acids were quantified. Polyunsaturated fatty acids and, in particular, linoleic acid were predominant. Beta-Sitosterol, delta(5)-avenasterol, and campesterol were the major sterols found. Differences were observed among the studied cultivars, especially in peroxide values and in the sterol profile.     

Chemical composition and larvicidal activity of the essential oils from Eupatorium betonicaeforme (D.C.) Baker (Asteraceae)

The volatile composition of the essential oils from leaves and roots of Eupatorium betonicaeforme (D.C.) Baker was analyzed by GC-MS. A total of 12 compounds were identified. beta-Caryophyllene (12.4-41.7%), alpha-humulene (11.7-14.6%), gamma-muurolene (10.4-19.0%), bicyclogermacrene (15.0-17.5%), 2,2-dimethyl-6-vinylchroman-4-one (10.3-25.5%), and 2-senecioyl-4-vinylphenol (8.5-41.0%) were the most prominent constituents. The former two compounds were isolated and characterized by spectroscopic data. The essential oils and the isolated compounds were tested against Aedes aegypti larvae survival. The results obtained show that the essential oil from roots and 2,2-dimethyl-6-vinylchroman-4-one (10.3-25.5%) could be considered as natural larvicidal agents.     

Gamma-linolenic acid and tocopherol contents in the seed oil of 47 accessions from several Ribes species

Gamma-linolenic acid is an essential fatty acid for humans with delta-6-desaturase deficiency; it is a precursor of prostaglandins, prostacyclins, and tromboxanes; and it has antiinflammatory and antitumoral effects. Tocopherols are natural antioxidants with biological activity, heart/vascular, and cancer protective properties. The oil, gamma-linolenic acid, and tocopherol contents, as well as tocopherol composition, were investigated in the seed oil of a collection of 47 accessions belonging to various species of the genus Ribes. Differences for oil content among species were not significant. The highest total tocopherol content was found in R. nigrum (mean, 1716 mg kg(-1) oil), followed by R. rubrum (mean, 1442 mg kg(-1) oil). R. grossularia showed the lowest values for this trait (mean, 786 mg kg(-1) oil). The three species also differed strongly for tocopherol composition. R. rubrumwas distinguished by a higher concentration of delta-tocopherol (mean, 20.2%); R. grossularia displayed the highest percentage of gamma-tocopherol (mean, 70.0%), and R. nigrum showed the highest concentration for alpha-tocopherol (mean, 34.8%), the most biologically active among the four tocopherols. Regarding gamma-linolenic acid, the highest content was found in R. nigrum, which exhibited up to 15.8% of this essential fatty acid in the oil. R. grossularia and R. rubrum showed mean gamma-linolenic acid contents of 8% and 6.2%, respectively. The present study indicated that seeds of Ribes species, especially R. nigrum, could be used as sources of gamma-linolenic acid and natural vitamin E.     

Analysis of volatile compounds and triglycerides of seed oils extracted from different poppy varieties (Papaver somniferum L.)

Poppy seed oil (Oleum Papaveris Seminis) is used for culinary and pharmaceutical purposes, as well as for making soaps, paints, and varnishes. Astonishingly, hardly anything was yet known about the volatile compounds of this promising comestible. Likewise, there are no current published data about the triglyceride (TAG) composition of poppy seed oils available. In this investigation solid-phase microextraction (SPME) with DVB/Carboxen/PDMS Stable-Flex fiber was applied to the study of volatile compounds of several seed oil samples from Papaver somniferum L. (Papaveraceae). 1-Pentanol (3.3-4.9%), 1-hexanal (10.9-30.9%), 1-hexanol (5.3-33.7%), 2-pentylfuran (7.2-10.0%), and caproic acid (2.9-11.5%) could be identified as the main volatile compounds in all examined poppy seed oil samples. Furthermore, the TAG composition of these oils was analyzed by MALDI-ReTOF- and ESI-IT-MS/MS. The predominant TAG components were found to be composed of linoleic, oleic, and palmitic acid, comprising approximately 70% of the oils. TAG patterns of the different poppy varieties were found to be very homogeneous, showing also no significant differences in terms of the applied pressing method of the plant seeds.     

Use of near-infrared spectroscopy for screening the individual and total glucosinolate contents in Indian mustard seed (Brassica juncea L. Czern. & Coss.)

The potential of near-infrared spectroscopy (NIRS) for screening the sinigrin, gluconapin, 4-hydroxyglucobrassicin, and total glucosinolate contents of Indian mustard (Brassica juncea L. Czern. & Coss.) seed was assessed. Intact seed samples of this species were analyzed by NIRS and their reference values regressed against different spectral transformations by modified partial least-squares (MPLS) regression. The coefficients of determination (r (2)) for sinigrin, gluconapin, 4-hydroxyglucobrassicin, and total glucosinolate contents were, respectively, 0.86, 0.95, 0.33, and 0.82. The standard deviation to standard error of prediction (SEP) ratio, and SEP to standard error of laboratory ratio were for these constituents as follows: sinigrin, 2.59 and 2.70; gluconapin, 4.16 and 2.08; 4-hydroxyglucobrassicin, 1.18 and 1.40; and total glucosinolates, 2.18 and 1.60. By comparison of commercial sinigrin spectrum with the first MPLS loadings of the sinigrin equation, it can be concluded that the molecule of sinigrin has a specific signal in the seed spectrum of Brassica.     

Preparation of interesterified plastic fats from fats and oils free of trans fatty acid

Interesterified plastic fats were produced with trans-free substrates of fully hydrogenated soybean oil, extra virgin olive oil, and palm stearin in a weight ratio of 10:20:70, 10:40:50, and 10:50:40, respectively, by lipase catalysis. The major fatty acids of the products were palmitic (32.2-47.4%), stearic (12.0-12.4%), and oleic acid (33.6-49.5%). After storage at 5 degrees C (refrigerator temperature) or 24 degrees C (room temperature) for 16 h, the physical properties were evaluated for solid fat content, texture, melting, and crystallization behavior, viscoelastic properties, crystal polymorphism, and crystal microstructure. The interesterified fats contained desirable crystal polymorphs (beta' form) as determined by X-ray diffraction spectroscopy. They exhibited a wide plastic range of solid fat content of 52-58% at 10 degrees C and 15% at 40 degrees C. The physical properties were influenced by the ratio of palm stearin and olive oil. Harder and more brittle texture, crystallization and melting at higher temperature, higher solid fat contents, and more elastic (G') or viscous (G') characteristics were observed in the produced fats containing a higher content of palm stearin and lower content of olive oil. The produced fats stored at 5 degrees C consisted mostly of beta' form crystal together with a small content of beta form, while those at 24 degrees C had only beta' form. The produced fat with a higher amount of palm stearin appeared to have more beta' form crystal and small size crystal clusters. Thus, the physical properties of the produced plastic fats may be desirable for use in a bakery product.     

Chemical composition of caneberry (Rubus spp.) seeds and oils and their antioxidant potential

Caneberries (Rubus spp. L.) are grown primarily throughout the Pacific Northwestern United States and Canada. Processing of caneberry fruit typically removes the seed, and the development of a value-added use of seeds could expand the market for caneberries and the profit margins for growers. An initial step toward the use of the seeds is a characterization of seed and oil. Our investigation has described compositional characteristics for seeds of five commonly grown caneberry species: red raspberry, black raspberry, boysenberry, Marion blackberry, and evergreen blackberry. Seeds from all five species had 6-7% protein and 11-18% oil. The oils contained 53-63% linoleic acid, 15-31% linolenic acid, and 3-8% saturated fatty acids. The two smaller seeded raspberry species had higher percentages of oil, the lowest amounts of saturated fatty acid, and the highest amounts of linolenic acid. Antioxidant capacities were detected both for whole seeds and for cold-pressed oils but did not correlate to total phenolics or tocopherols. Ellagitannins and free ellagic acid were the main phenolics detected in all five caneberry species and were approximately 3-fold more abundant in the blackberries and the boysenberry than in the raspberries.     

Chemical composition and antimicrobial activity of the essential oils from the gum of Turkish pistachio (Pistacia vera L.)

The essential oil from the gum of Pistachio (Pistacia vera L. (Anacardiaceae)) grown in Turkey was obtained by the hydro-distillation method, and its chemical composition was analyzed by GC and GC-MS. Moreover, the antimicrobial activities of the oil against the growth of 13 bacteria and 3 pathogenic yeasts were evaluated using the agar-disk diffusion and minimum inhibitory concentration (MIC) methods. The results showed that the essential oil contained about 89.67% monoterpenes, 8.1% oxygenated monoterpenes and 1.2% diterpenes. alpha-Pinene (75.6%), beta-pinene (9.5%), trans-verbenol (3.0%), camphene (1.4%), trans-pinocarveol (about 1.20%), and limonene (1.0%) were the major components. The antimicrobial results showed that the oil inhibited nine bacteria and all the yeasts studied, and the activities were considerably dependent upon concentration and its bioactive compounds such as carvacrol, camphene, and limonene. Moreover, the essential oil of the gum was found to be more effective yeastcide than Nystatin, synthetic yeastcide. Furthermore, the antibacterial activities of the oil were lower than those of standard antibiotics, ampicillin sodium, and streptomycine sulfate under the conditions studied.