Antimicrobial Carvacrol in Solution Blow-Spun Fish-Skin Gelatin Nanofibers.

Carvacrol is a volatile monoterpenic phenol and main component of oregano essential oil that shows nonspecific antimicrobial activity against foodborne pathogenic bacteria. Fish-skin gelatin (FSG) nanofibers encapsulating carvacrol (15%, 20%, 25%, and 30%, w/w FSG) were successfully prepared via solution blow-spinning (SBS) technique using lecithin (2.475% wb) as the surfactant. FSG emulsions with lower carvacrol ratios (5% and 10%) showed higher values in particle size and surface tension as well as lower values in viscosity and modulus, which led to failure of maintaining nanofibers shape. The formed carvacrol-FSG nanofibers showed round and smooth morphologies with average fiber diameters ranging from 103.2 to 138.1 nm as the carvacrol ratio increased from 15% to 30%. Carvacrol was evenly dispersed within the interior of nanofiber matrix. All carvacrol-FSG nanofibers showed inhibitive effects against the growth of Escherichia coli, Salmonella enterica, and Listeria monocytogenes. Moreover, nanofibers with lower carvacrol ratios showed bigger inhibition zones for E. coli and L. monocytogenes (20 mm compared with 12.5 mm for lowest to highest carvacrol ratios, respectively). Nanofibers stored at 20 °C (51% RH) showed better retention (40% to 60%) for carvacrol during the first 4 weeks of storage, while nanofibers stored at 2 °C (70% RH) showed better retention (10% to 30%) at the end of storage. PRACTICAL APPLICATION: Results obtained in the study may help with antimicrobial carvacrol addition levels for gelatin fiber preparation using solution blow spinning (SBS) method. SBS gelatin fibers with added antimicrobials have potential applications for food packaging and medical wound dressing.

Cooked carrot volatiles. AEDA and odor activity comparisons. Identification of linden ether as an important aroma component.

MS with GC-RI evidence was found for the presence of linden ether in cooked carrot (Daucus carota). Evaluation of the GC effluent from cooked carrot volatiles using aroma extract dilution analysis (AEDA) found linden ether with the highest flavor dilution (FD) factor. Others with 10-fold lower FD factors were ß-ionone, eugenol, the previously unidentified ß-damascenone, (E)-2-nonenal, octanal (+ myrcene), and heptanal. All other previously identified volatiles showed lower FD factors. Odor thresholds, concentrations, and odor activity values of previously identified compounds are reviewed. This indicated that at least 20 compounds occur in cooked carrots above their odor thresholds (in water). Compounds showing the highest odor activity values included ß-damascenone, (E)-2-nonenal, (E,E)-2,4-decadienal, ß-ionone, octanal, (E)-2-decenal, eugenol, and p-vinylguaiacol.

Irregular sesquiterpenoids from Ligusticum grayi roots.

Root oil of Ligusticum grayi (Apiaceae) contains numerous irregular sesquiterpenoids. In addition to the known acyclic sesquilavandulol and a sesquilavandulyl aldehyde, two thapsanes, one epithapsane, and 14 sesquiterpenoids representing eight hitherto unknown carbon skeletons were found. These skeletons are: prethapsane, i.e. 1,1,2,3a,7,7-hexamethyloctahydro-1H-indene; isothapsane, i.e. 1,2,3a,6,7,7a-hexamethyloctahydro-1H-indene; ligustigrane, i.e. 1,1,2,7,7,7a-hexamethyloctahydro-1H-indene; isoligustigrane, i.e. 1,1,2,6,7,7a-hexamethyloctahydro-1H-indene; preisothapsane, i.e. 1,1,2,3a,6,7-hexamethyloctahydro-1H-indene; isoprethapsane, i.e. 1,1,2,4,7,7-hexamethyloctahydro-1H-indene; allothapsane, i.e. 1,1,2,3a,7,7a-hexamethyloctahydro-1H-indene; and oshalagrane, i.e. 1,1,2,4,6,6-hexamethylspiro[4.4]nonane. The bicyclic sesquiterpenoids are presumably biosynthesized by head-to-head coupling of geranyl diphosphate and dimethylallyl diphosphate, followed by a cyclization sequence leading to a hydroindane skeleton with six one-carbon substituents. Subsequent rearrangements--primarily methyl migrations--account for the remarkable variety of structures represented in L. grayi root oil.

Antiplatelet activities of newly synthesized derivatives of piperlongumine.

Piperlongumine, a pyridone alkaloid isolated from Piper longum L., exhibited a potential inhibitory effect on washed rabbit platelet aggregation induced by collagen, arachidonic acid (AA) and platelet activating factor (PAF), without any inhibitory effect on that induced by thrombin. Piperlongumine was used as a lead compound for the synthesis of new antiplatelet agents. Seven synthetic compounds were newly synthesized from 3,4,5-trimethoxycinnamic acid (TMCA). They were 1-piperidin-1-yl-3-(3,4,5-trimethoxy-phenyl)prop-2-en-1-one (1'), 1-morpholin-4-yl-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (2'), 1-(3,5-dimethylpiperidin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (3'), 1-(2-methylpiperidin-1-yl)-3-(3,4,5-tri-methoxyphenyl)prop-2-en-1-one (4'), 1-(3-hydroxypiperidin-1-yl)-3-(3,4,5-trimethoxyphenyl)- prop-2-en-1-one (5'), 1-[3-(3,4,5-tri-methoxyphenyl) acryloyl]-piperidin-2-one (6') and ethyl 1-[3-(3,4,5-trimethoxyphenyl)-acryloyl]piperidine-4-carboxylate (7'). Among those seven synthetic derivatives, 1-(3,5-dimethylpiperidin-1-yl)-3-(3,4,5-trimethoxyphenyl)prop-2-en-1-one (3') had the most inhibitory effect on platelet aggregation induced by collagen, AA and PAF.

Antimalarial activity of anthothecol derived from Khaya anthotheca (Meliaceae).

Antimalarial activity of anthothecol, a limonoid of Khaya anthotheca (Meliaceae) against Plasmodium falciparum was tested using a [(3)H]-hypoxanthine and 48h culture assay in vitro. Anthotechol showed potent antimalarial activity against malaria parasites with IC(50) values of 1.4 and 0.17microM using two different assays. Also, gedunin had antimalarial activity with IC(50) values of 3.1 and 0.14microM. However, the citrus limonoids, limonin and obacunone did not show any antimalarial activity. The antimalarial activities were compared with the three currently used antimalarial medicines quinine, chloroquinine and artemisinin.

Inhibitory effects of Tabebuia impetiginosa inner bark extract on platelet aggregation and vascular smooth muscle cell proliferation through suppressions of arachidonic acid liberation and ERK1/2 MAPK activation.

The antiplatelet and antiproliferative activities of extract of Tabebuia impetiginosa inner bark (taheebo) were investigated using washed rabbit platelets and cultured rat aortic vascular smooth muscle cells (VSMCs) in vitro. n-Hexane, chloroform and ethyl acetate fractions showed marked and selective inhibition of platelet aggregation induced by collagen and arachidonic acid (AA) in a dose-dependent manner. These fractions, especially the chloroform fraction, also significantly suppressed AA liberation induced by collagen in [(3)H]AA-labeled rabbit platelets. The fractions, especially the chloroform fraction, potently inhibited cell proliferation and DNA synthesis induced by platelet derived growth factor (PDGF)-BB, and inhibited the levels of phosphorylated extracellular signal regulated kinase (ERK1/2) mitogen activated protein kinase (MAPK) stimulated by PDGF-BB, in the same concentration range that inhibits VSMC proliferation and DNA synthesis.

Antibacterial activity of Tabebuia impetiginosa Martius ex DC (Taheebo) against Helicobacter pylori.

The growth-inhibiting activity of Tabebuia impetiginosa Martius ex DC dried inner bark-derived constituents against Helicobacter pylori ATCC 43504 was examined using paper disc diffusion and minimum inhibitory concentration (MIC) bioassays. The activity of the isolated compounds was compared to that of the commercially available anti-Helicobacter pylori agents, amoxicillin, metronidazole, and tetracycline. The biologically active components of Tabebuia impetiginosa dried inner bark (taheebo) were characterized by spectroscopic analysis as 2-(hydroxymethyl)anthraquinone, anthraquinone-2-carboxylic acid, and 2-hydroxy-3-(3-methyl-2-butenyl)-1,4-naphthoquinone (lapachol). With the paper disc diffusion assay 2-(hydroxymethyl)anthraquinone exhibited strong activity against Helicobacter pylori ATCC 43504 at 0.01 mg/disc. Anthraquinone-2-carboxylic acid, lapachol and metronidazole were less effective, exhibiting moderate anti-Helicobacter pylori activity at 0.1 mg/disc. Amoxicillin and tetracycline were the most potent compounds tested, displaying very strong activity at 0.005 mg/disc. 2-(Hydroxymethyl)anthraquinone exhibited moderate activity at this dose. Tetracycline still had strong activity at 0.001 mg/disc while amoxicillin had little activity at this dose. In the MIC bioassay, 2-(hydroxymethyl)anthraquinone (2 microg/mL), anthraquinone-2-carboxylic acid (8 microg/mL), and lapachol (4 microg/mL) were more active than metronidazole (32 microg/mL) but less effective than amoxicillin (0.063 microg/mL) and tetracycline (0.5 microg/mL). The anti-Helicobacter pylori activity of seven 1,4-naphthoquinone derivatives (structurally related to lapachol), 1,4-naphthoquinone, 5,8-dihydroxy-1,4-naphthoquinone (naphthazarin), 2-methyl-1,4-naphthoquinone (menadione), 2-hydroxy-1,4-naphthoquinone (lawsone), 5-hydroxy-2-methyl-1,4-naphthoquinone (plumbagin), 5-hydroxy-1,4-naphthoquinone (juglone), and 2,3-dichloro-1,4-naphthoquinone (dichlone) was also evaluated using the paper disc assay. Menadione and plumbagin were the most potent compounds tested with the later still exhibiting very strong activity at 0.001 mg/disc. Menadione, juglone and tetracycline had strong activity at this low dose while the latter two compounds and amoxicillin had very strong activity at 0.005 mg/disc. Lawsone was unusual in that it had very strong activity at 0.1 and 0.05 mg/disc but weak activity at doses of 0.01 mg/disc and lower. Naphthazalin, lapachol and dichlone had similar activities while metronidazole had the lowest activity of all compounds tested. These results may be an indication of at least one of the pharmacological actions of taheebo. The Tabebuia impetiginosa dried inner bark-derived materials, particularly 2-(hydroxymethyl)anthraquinone, merit further study as potential Helicobacter pylori eradicating agents or lead compounds.

Identification of benzalkonium chloride in commercial grapefruit seed extracts.

Commercial grapefruit seed extracts (GSE) were extracted with chloroform. The solvent was evaporated, and the resulting solid was subsequently analyzed by high-performance liquid chromatography (HPLC), electrospray ionization mass spectrometry (ESI/MS), tandem mass spectrometry (ESI/MS/MS), and elemental analysis (by proton-induced X-ray emission analysis). Three major constituents were observed by HPLC and were identified as benzyldimethyldodecylammonium chloride, benzyldimethyltetradecylammonium chloride, and benzyldimethylhexadecylammonium chloride. This mixture of homologues is commonly known as benzalkonium chloride, a widely used synthetic antimicrobial ingredient used in cleaning and disinfection agents.

Inhibitory effect on proliferation of vascular smooth muscle cells and protective effect on CCl(4)-induced hepatic damage of HEAI extract.

The effects of methanol extract from Hericium erinaceus cultivated with Artemisia iwayomogi (HEAI) on proliferation of vascular smooth muscle cells and CCl(4)-induced hepatic damage were evaluated. HEAI was shown to have a potent inhibitory effect on the proliferation of vascular smooth muscle cells (VSMCs). Interestingly, a methanol extract of Hericium erinaceus showed no inhibitory effect on the proliferation of VSMCs, while a methanol extract of Artemisia iwayomogi possessed strong inhibitory effects on the proliferation of VSMCs. Therefore, the inhibitory effects of HEAI may be caused by the changes of chemical components in the culture broth after the addition of Artemisia iwayomogi in the HEAI growth media. HEAI also had a strong protective effect on CCl(4)-induced hepatic damage in rats. The activity was evaluated using biochemical parameters such as glutamic oxalacetic transaminase (GOT), glutamic pyruvic transaminase (GPT) and alkaline phosphatase (ALP). HEAI treatment caused a significant reduction in the activity of GOT but not of GPT and ALP in comparison with CCl(4) treatment alone. Histopathological studies showed that liver samples treated with HEAI were significantly different when compared to non-treated animals after CCl(4) exposure.

Differential effects of tomato (Lycopersicon esculentum mill) matrix on the volatility of important aroma compounds.

Significant tomato matrix effects on the volatility of certain fresh tomato odorants were found. The concentrations of odorants such as (E,E)-2,4-decadienal, beta-damascenone, and beta-ionone, in crushed fresh tomato fruit obtained by solid-phase microextraction (SPME), resulting from a tomato matrix calibration curve were 5.5-, 2-, and 12-fold higher, respectively, than those calculated by calibration based on buffer solutions. Static headspace analyses indicated that, in most cases, the tomato matrix significantly retains the odorants relative to the buffer solution. Thus, the concentration of odorants in the headspace of tomato is lower than expected compared to a simple matrix such as buffer. CaCl(2), although needed in crushed fruit tissue to block enzymatic activity, was found to interact specifically with 2-isobutylthiazole, reducing its content in the headspace by at least 6-fold. If a matrix effect is found, analysis of the odorant molecule contents in the headspace rather than in the food is recommended in order to better evaluate their access to the olfactory receptors.

Antioxidant constituents of almond [Prunus dulcis (Mill.) D.A. Webb] hulls.

Almond hulls (Nonpareil variety) were extracted with methanol and analyzed by reversed phase HPLC with diode array detection. The extract contained 5-O-caffeoylquinic acid (chlorogenic acid), 4-O-caffeoylquinic acid (cryptochlorogenic acid), and 3-O-caffeoylquinic acid (neochlorogenic acid) in the ratio 79.5:14.8:5.7. The chlorogenic acid concentration of almond hulls was 42.52 +/- 4.50 mg/100 g of fresh weight (n = 4; moisture content = 11.39%). Extracts were tested for their ability to inhibit the oxidation of methyl linoleate at 40 degrees C. At an equivalent concentration (10 microg/1 g of methyl linoleate) almond hull extracts had higher antioxidant activity than alpha-tocopherol. At higher concentrations (50 microg/1 g of methyl linoleate) almond hull extracts showed increased antioxidant activity that was similar to chlorogenic acid and morin [2-(2,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-one] standards (at the same concentrations). These data indicate that almond hulls are a potential source of these dietary antioxidants. The sterols (3beta,22E)-stigmasta-5,22-dien-3-ol (stigmasterol) and (3beta)-stigmast-5-en-3-ol (beta-sitosterol) (18.9 mg and 16.0 mg/100 g of almond hull, respectively) were identified by GC-MS of the silylated almond hull extract.

Antioxidant activity and characterization of volatile constituents of Taheebo (Tabebuia impetiginosa Martius ex DC).

Volatiles were isolated from the dried inner bark of Tabebuia impetiginosa using steam distillation under reduced pressure followed by continuous liquid-liquid extraction. The extract was analyzed by gas chromatography and gas chromatography-mass spectrometry. The major volatile constituents of T. impetiginosa were 4-methoxybenzaldehyde (52.84 microg/g), 4-methoxyphenol (38.91 microg/g), 5-allyl-1,2,3-trimethoxybenzene (elemicin; 34.15 microg/g), 1-methoxy-4-(1E)-1-propenylbenzene (trans-anethole; 33.75 microg/g), and 4-methoxybenzyl alcohol (30.29 microg/g). The antioxidant activity of the volatiles was evaluated using two different assays. The extract exhibited a potent inhibitory effect on the formation of conjugated diene hydroperoxides (from methyl linoleate) at a concentration of 1000 microg/mL. The extract also inhibited the oxidation of hexanal for 40 days at a level of 5 microg/mL. The antioxidative activity of T. impetiginosa volatiles was comparable with that of the well-known antioxidants, alpha-tocopherol, and butylated hydroxytoluene.