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Commiphora myrrh resin (Myrrh) has been used in traditional Arabic medicine to treat various inflammatory diseases. Two furano-sesquiterpenoids, 2-methoxyfuranodiene (CM1) and 2-acetoxyfuranodiene (CM2), were isolated from the chloroform fraction of the ethanolic extract of Arabic Commiphora myrrh resin. The cytotoxicity of the compounds was evaluated using human liver carcinoma, breast cancer cells (HepG2 and MCF-7, respectively) and normal human umbilical vein endothelial cells (HUVECs) cell lines. The development toxicity and anti-angiogenic activity of both compounds were also evaluated using zebrafish embryos. Cell survival assays demonstrated that both compounds were highly cytotoxic in HepG2 and MCF7 cells, with IC50 values of 3.6 and 4.4 µM, respectively. Both compounds induced apoptosis and caused cell cycle arrest in treated HepG2 cells, which was observed using flow cytometric analysis. The development toxicity in zebrafish embryos showed the chronic toxicity of both compounds. The toxicity was only seen when the embryos remained exposed to the compounds for more than three days. The compound CM2 showed a significant level of anti-angiogenic activity in transgenic zebrafish embryos at sublethal doses. Thus, we demonstrated the cytotoxic properties of both compounds, suggesting that the molecular mechanism of these compounds should be further assessed.

The aim of this study was to compare the biodistribution in mice of functionalized rhodamine B (Rh) labeled colchicine derivative furano-allocolchicinoid (AC, 6) either conjugated to 40 kDa chitosan (AC-Chi, 8) or encapsulated into chitosan nanoparticles (AC-NPs). AC-NPs were formed by ionotropic gelation and were 400–450 nm in diameter as estimated in mice by dynamic light scattering and confocal microscopy. AC-Chi and AC-NPs preserved the specific colchicine activity in vitro. AC preparations were once IV injected into C75BL/6 mice; muscles, spleen, kidney, liver, lungs, blood cells and serum were collected at 30 min, 2, 5, 10, and 20 h post injection. To analyze the distribution of the furano-allocolchicinoid preparations in body liquids and tissues, Rh was measured directly in sera or extracted by acidic ethanol from tissue homogenates. Preliminary Rh extraction rate was estimated in vitro in tissue homogenates and was around 25–30% from total quantity added. After in vivo injection, AC-NPs were accumulated more in liver and spleen, while less in kidney and lungs in comparison with free AC and AC-Chi. Therefore, incorporation of colchicine derivatives as well as other hydrophobic substances into nano/micro sized carriers may help redistribute the drug to different organs and, possibly, improve antitumor accumulation.

Furan and its derivatives were identified in a small number of heat-treated foods back in the 60's and 70's. In May 2004, US Food and Drug Administration published a report on the occurrence of parent furan in a number of thermally treated foods. Since furan has been classified as possibly carcinogenic to human by IARC, a great concern has been addressed to the analysis of this substance naturally-occurring in food. This paper gives a short overview on the mechanistic pathways of the parent furan formation in food by degradation of amino acids and/or reducing sugars, and oxidation of ascorbic acid and polyunsaturated acids which can be induced by thermal or irradiation treatments; further, it deals with the metabolism and toxicology of furan as well as with the comparison of the methods of furan determination.

Major and minor compounds in a traditional Mexican spirit, young mezcal from Agave angustifolia and Agave potatorum, were characterised using gas chromatography and solid phase microextraction-gas chromatography-mass spectrometry. A large variability in both mezcal samples was detected in the content of methanol, higher alcohols, acetic acid, and ethyl acetate. However, their values were below the maximum concentration permitted by the Mexican Standards. The minor compounds identified by mass spectrometry included alcohols, esters, ketones, acids, and furanes. The similarities found between mezcal from Agave angustifolia and Agave potatorum may be due to their processing methods. In addition, mezcals contain unique compounds that can be used as markers to identify the products of different origins.

Analogs of the seco-cyclopyrroloindoline (seco-CPI), the DNA alkylation pharmacophore of CC-1065 and the duocarmycins, can be prepared through a 5-exo-trig radical cyclization of a free radical and a 3-chloro-2-allylic moiety. This manuscript reports an unexpected discovery that, depending on the structure and stability of the free radical, the cyclization process leads to the production of an appreciable amount of seco- cyclopropyltetrahydroquinolines 7a-d along with the seco-cyclopropoyltetra- hydroindoline products (6a-e). For instance, free radical reaction of the bromoallylic chloride 5a produced an equal amount of 6-benzyloxy-N-t-butoxycarbonyl-3- (chloromethyl)furano[e]indoline (6a), and 7-benzyloxy-N-t-butoxycarbonyl-3-chloro- 1,2,3,4-tetrahydrofurano[f]quinoline (7a). Three other examples that produced mixtures of indoline and quinoline products are provided. In only one of the examples reported in this manuscript, the 6-benzyloxy-N-t-butoxycarbonyl-3-(chloromethyl)benzo[e]indoline, was a seco-CBI precursor 6e formed exclusively, consistent with literature precedents.

The chemical composition of odors produced by nine strains of streptomycetes (Streptomyces aureofaciens, S. avermitilis, S. cinnamonensis, S. coelicolor, S. griseus, S. lividans, S. rimosus, S. spectabilis, S. virginiae) cultivated in a fermentor under similar cultivation conditions was determined. GC-MS analysis identified more than twenty noteworthy volatile chemical individuals. The main components of the odor spectrum were geosmin and unique homologues of oxolones (dihydrofuranones); minor compounds included pyrazine derivatives, acetoin and its homologues, aromatic esters, and furan derivatives.

Volatile organic compounds (VOC) from crude and heat treated amaranth samples were collected by solid-phase microextraction (SPME) method and identified by gas chromatography with mass spectrometry. The list of identified VOC exceeds one hundred substances of different classes. Total VOC concentrations ranged from 2.2 to 68.9 microg/g of dried sample. Hexanal and acetic acid were the most abundant VOC. The highest values of VOC emissions were found in popped amaranth grains in comparison with all crude grains and amaranth biomasses.

Several insecticidal compounds have been identified by bioassay-driven fractionation of avocado, Persea americana Mill, idioblast cell oil. A flash chromatography fraction of the oil showed substantial toxicity to early instars of the generalist insect herbivore, Spodoptera exigua (Hubner) (100% mortality after seven days). Following further fractionation, five biologically active compounds, 2-(pentadecyl)furan, 2-(heptadecyl)furan, 2-(1E-pentadecenyl)furan, 2-(8Z,11Z-heptadecadienyl)furan, and the triglyceride triolein, were identified. Several minor components were also tentatively identified, including 2-(1Z-pentadecenyl)furan, 2-(1E-heptadecenyl)furan, and 2-(1E,8Z,11Z-heptadecatrienyl)furan. Several 2-alkylfurans of this type have been reported previously from avocado (Persea spp.) and have received the common name of avocadofurans. The major compounds were tested individually for toxic and growth inhibitory effects. Individually, the compounds had low to moderate toxicity. Of these, 2-(pentadecyl)furan had the greatest effects, with an LC50 value of 1031 micrograms/g. At concentrations of 600 micrograms/g or higher in diets, larval growth was inhibited by 70% compared to controls. The analogous 2-(heptadecyl)furan had an LC50 value of 1206 micrograms/g, and also significantly reduced larval growth ( 75% versus controls) at concentrations of 600 micrograms/g. The unsaturated analogs 2-(1E-pentadecenyl)furan and 2-(8Z,11Z-heptadecadienyl)furan were less toxic. Triolein was only weakly toxic, with an LC50 value of 10,364 micrograms/g diet. Larval growth was inhibited only at concentrations of 7000 micrograms/g or higher. The potential of avocadofurans in insect control is discussed

The efficacy of dicationic diarylfurans was evaluated against Cryptosporidium parvum by a suckling murine model. Candidate drugs were solubilized or suspended in deionized water and administered orally at a constant dose rate on days 0-5 (treatment day 0) to suckling ICR Swiss mice experimentally inoculated with oocysts of C. parvum. Efficacy was based on numbers of oocysts recovered from the intestinal tracts of mice subjected to necropsy examination on day 6. Numerous candidate furans significantly reduced the numbers of oocysts recovered from treated mice compared with control mice. Compounds 1, 2, 4, and 9 demonstrated superior efficacies (10% of controls or better) against C. parvum. Compounds 3, 5, 6, 7, 8, 11, 17, 18, and 19 also significantly reduced the numbers of oocysts recovered from treated mice but demonstrated efficacies ranging from 17 to 65% of controls. Compound 4 was particularly efficacious against C. parvum at a dosage as low as 8.5 mg/kg of body weight. Compound 4 is identified as a lead compound for additional studies in other animal models.

Lime peel, parsnip, lemon peel, dried parsley flakes, cold-pressed lime oil, and distilled lime oil samples were analyzed for the presence and concentration of the linear furanocoumarins (LFs) psoralen, 5-methoxypsoralen (5-MOP), and 8-methoxypsoralen (8-MOP) by thin layer chromatography and gas chromatography-mass spectrometry. Cold-pressed lime oil had the highest LF content (psoralen, 67 +/- 29 micrograms/ml, 5-MOP, 1.634 +/- 62 micrograms/ml, and 8-MOP, 44 +/- 2 micrograms/ml). The antimicrobial effectiveness of LFs against Listeria monocytogenes, Escherichia coli O157:H7, and Micrococcus luteus was tested in a model food system consisting of a slurry of 25% commercial \"garden vegetables\" baby food in 0.1% peptone water. Inhibition required UV activation after the addition of the LFs to the model system. Lime peel extract, cold-pressed lime oil, and a 5-MOP standard inhibited the growth of L. monocytogenes, but not E. coli O157:H7. M. luteus was inhibited only by the cold-pressed lime oil. The minimum LF concentration that caused inhibition of the growth of L. monocytogenes was 32 micrograms/g and the minimum bactericidal concentration was 43 micrograms/g. Cold-pressed lime oil inhibited L. monocytogenes even at the lowest concentration added to the model system (10 micrograms/g), while the corresponding LF standard did not. This suggested the presence of other antimicrobial agents in the oil