High-Throughput Screening of Australian Marine Organism Extracts for Bioactive Molecules Affecting the Cellular Storage of Neutral Lipids
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{"title"=>"High-throughput screening of Australian marine organism extracts for bioactive molecules affecting the cellular storage of neutral lipids", "type"=>"journal", "authors"=>[{"first_name"=>"James", "last_name"=>"Rae", "scopus_author_id"=>"36570721300"}, {"first_name"=>"Frank", "last_name"=>"Fontaine", "scopus_author_id"=>"7005575815"}, {"first_name"=>"Angela A.", "last_name"=>"Salim", "scopus_author_id"=>"36899846600"}, {"first_name"=>"Harriet P.", "last_name"=>"Lo", "scopus_author_id"=>"7202085501"}, {"first_name"=>"Robert J.", "last_name"=>"Capon", "scopus_author_id"=>"7005012355"}, {"first_name"=>"Robert G.", "last_name"=>"Parton", "scopus_author_id"=>"7101912368"}, {"first_name"=>"Sally", "last_name"=>"Martin", "scopus_author_id"=>"7404840734"}], "year"=>2011, "source"=>"PLoS ONE", "identifiers"=>{"pui"=>"362294563", "scopus"=>"2-s2.0-79961195711", "isbn"=>"1932-6203 (Electronic)\\r1932-6203 (Linking)", "pmid"=>"21857959", "sgr"=>"79961195711", "issn"=>"19326203", "doi"=>"10.1371/journal.pone.0022868"}, "id"=>"92ea5939-8641-3b98-a257-9242294c13ac", "abstract"=>"Mammalian cells store excess fatty acids as neutral lipids in specialised organelles called lipid droplets (LDs). Using a simple cell-based assay and open-source software we established a high throughput screen for LD formation in A431 cells in order to identify small bioactive molecules affecting lipid storage. Screening an n-butanol extract library from Australian marine organisms we identified 114 extracts that produced either an increase or a decrease in LD formation in fatty acid-treated A431 cells with varying degrees of cytotoxicity. We selected for further analysis a non-cytotoxic extract derived from the genus Spongia (Heterofibria). Solvent partitioning, HPLC fractionation and spectroscopic analysis (NMR, MS) identified a family of related molecules within this extract with unique structural features, a subset of which reduced LD formation. We selected one of these molecules, heterofibrin A1, for more detailed cellular analysis. Inhibition of LD biogenesis by heterofibrin A1 was observed in both A431 cells and AML12 hepatocytes. The activity of heterofibrin A1 was dose dependent with 20 µM inhibiting LD formation and triglyceride accumulation by ∼50% in the presence of 50 µM oleic acid. Using a fluorescent fatty acid analogue we found that heterofibrin A1 significantly reduces the intracellular accumulation of fatty acids and results in the formation of distinct fatty acid metabolites in both cultured cells and in embryos of the zebrafish Danio rerio. In summary we have shown using readily accessible software and a relatively simple assay system that we can identify and isolate bioactive molecules from marine extracts, which affect the formation of LDs and the metabolism of fatty acids both in vitro and in vivo.", "link"=>"http://www.mendeley.com/research/highthroughput-screening-australian-marine-organism-extracts-bioactive-molecules-affecting-cellular", "reader_count"=>21, "reader_count_by_academic_status"=>{"Researcher"=>2, "Student > Doctoral Student"=>3, "Student > Ph. D. Student"=>4, "Student > Postgraduate"=>1, "Student > Master"=>5, "Lecturer"=>1, "Professor"=>4}, "reader_count_by_user_role"=>{"Researcher"=>2, "Student > Doctoral Student"=>3, "Student > Ph. D. Student"=>4, "Student > Postgraduate"=>1, "Student > Master"=>5, "Lecturer"=>1, "Professor"=>4}, "reader_count_by_subject_area"=>{"Engineering"=>1, "Biochemistry, Genetics and Molecular Biology"=>3, "Agricultural and Biological Sciences"=>10, "Medicine and Dentistry"=>3, "Chemistry"=>2, "Social Sciences"=>1}, "reader_count_by_subdiscipline"=>{"Engineering"=>{"Engineering"=>1}, "Medicine and Dentistry"=>{"Medicine and Dentistry"=>3}, "Chemistry"=>{"Chemistry"=>2}, "Social Sciences"=>{"Social Sciences"=>1}, "Agricultural and Biological Sciences"=>{"Agricultural and Biological Sciences"=>10}, "Biochemistry, Genetics and Molecular Biology"=>{"Biochemistry, Genetics and Molecular Biology"=>3}}, "reader_count_by_country"=>{"United States"=>1}, "group_count"=>0}

Scopus | Further Information

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Figshare

  • {"files"=>["https://ndownloader.figshare.com/files/376869", "https://ndownloader.figshare.com/files/376898", "https://ndownloader.figshare.com/files/376932"], "description"=>"<div><p>Mammalian cells store excess fatty acids as neutral lipids in specialised organelles called lipid droplets (LDs). Using a simple cell-based assay and open-source software we established a high throughput screen for LD formation in A431 cells in order to identify small bioactive molecules affecting lipid storage. Screening an <em>n</em>-butanol extract library from Australian marine organisms we identified 114 extracts that produced either an increase or a decrease in LD formation in fatty acid-treated A431 cells with varying degrees of cytotoxicity. We selected for further analysis a non-cytotoxic extract derived from the genus <em>Spongia (Heterofibria)</em>. Solvent partitioning, HPLC fractionation and spectroscopic analysis (NMR, MS) identified a family of related molecules within this extract with unique structural features, a subset of which reduced LD formation. We selected one of these molecules, heterofibrin A1, for more detailed cellular analysis. Inhibition of LD biogenesis by heterofibrin A1 was observed in both A431 cells and AML12 hepatocytes. The activity of heterofibrin A1 was dose dependent with 20 µM inhibiting LD formation and triglyceride accumulation by ∼50% in the presence of 50 µM oleic acid. Using a fluorescent fatty acid analogue we found that heterofibrin A1 significantly reduces the intracellular accumulation of fatty acids and results in the formation of distinct fatty acid metabolites in both cultured cells and in embryos of the zebrafish <em>Danio rerio</em>. In summary we have shown using readily accessible software and a relatively simple assay system that we can identify and isolate bioactive molecules from marine extracts, which affect the formation of LDs and the metabolism of fatty acids both <em>in vitro</em> and <em>in vivo</em>.</p> </div>", "links"=>[], "tags"=>["high-throughput", "australian", "extracts", "bioactive", "molecules", "affecting", "cellular", "lipids"], "article_id"=>134449, "categories"=>["Biochemistry", "Chemistry", "Genetics"], "users"=>["James Rae", "Frank Fontaine", "Angela A. Salim", "Harriet P. Lo", "Robert J. Capon", "Robert G. Parton", "Sally Martin"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0022868.s001", "https://dx.doi.org/10.1371/journal.pone.0022868.s002", "https://dx.doi.org/10.1371/journal.pone.0022868.s003"], "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/High_Throughput_Screening_of_Australian_Marine_Organism_Extracts_for_Bioactive_Molecules_Affecting_the_Cellular_Storage_of_Neutral_Lipids/134449", "title"=>"High-Throughput Screening of Australian Marine Organism Extracts for Bioactive Molecules Affecting the Cellular Storage of Neutral Lipids", "pos_in_sequence"=>0, "defined_type"=>4, "published_date"=>"2011-08-08 01:14:09"}
  • {"files"=>["https://ndownloader.figshare.com/files/748294"], "description"=>"<p>(A) A431 cells were maintained for 18 h in media containing either 10% FCS (FCS), 10% delipidated FCS (delipidation) or 10% delipidated FCS supplemented with 50 µM oleic acid (oleic acid). Cells were fixed and stained for LDs using Bodipy493/503. (B) A431 cells were maintained for 8 h in 10% delipidated FCS supplemented with 50 µM oleic acid. Following fixation cells were stained for LDs using Bodipy493/503 (green) and nuclei (blue). Native images were obtained using a BD Pathway automated confocal microscope. CellProfiler software was used to generate segmentation masks to identify individual nuclei, cytoplasmic area and LDs, and to subsequently generate a related LD mask, using the analysis pipeline detailed in <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0022868#s2\" target=\"_blank\">Materials and Methods</a>, and <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0022868#pone.0022868.s001\" target=\"_blank\">Tables S1</a> and <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0022868#pone.0022868.s002\" target=\"_blank\">S2</a>. (C, D) The ability of the automated analysis pipeline to quantify LD formation was examined using triacsin C, a potent inhibitor of TG synthesis. A431 cells were maintained overnight in delipidated serum ± varying concentrations of triacsin C. Cells were subsequently supplemented with 50 µM oleic acid for 8 h. Images of fixed, labelled cells were analysed using the CellProfiler analysis pipeline to determine both the mean number of LDs/cell ((C) mean ± sem, n>145 cells) or the frequency distribution of cells containing a specific number of LDs (D). Ctrl indicates cells incubated in delipidated serum only. (E) A431 cells were incubated with varying concentrations of inactivated generic <i>n</i>-butanol marine extract for 18 h. Cells were fixed, the nuclei stained using DAPI and the number of cells per field quantified.</p>", "links"=>[], "tags"=>["chemistry", "genetics and genomics", "Biochemistry"], "article_id"=>418665, "categories"=>["Biochemistry", "Chemistry", "Genetics"], "users"=>["James Rae", "Frank Fontaine", "Angela A. Salim", "Harriet P. Lo", "Robert J. Capon", "Robert G. Parton", "Sally Martin"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0022868.g001"], "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Assay_design_and_validation_/418665", "title"=>"Assay design and validation.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-08-08 02:24:25"}
  • {"files"=>["https://ndownloader.figshare.com/files/748423"], "description"=>"<p>(A) LD biogenesis assay design. A431 cells were seeded for 6 h in growth medium then transferred into delipidated medium supplemented with control reagents or experimental extracts. Following incubation for 15 h cells were further supplemented with oleic acid for 8 h prior to fixation and processing. (B) Results obtained from a typical 96-well plate in the primary screen. A431 cells were incubated with <i>n</i>-butanol marine extracts at 50 µg/mL overnight prior to supplementation with 50 µM oleic acid for 8 h. Cells were subsequently fixed, stained for cell nuclei (DAPI) and LDs (Bodipy493/503). The average number of LDs/cell and the average number of nuclei/field were quantified. Each point represents the average of duplicate wells treated with a single extract. Results are shown for 42 randomly chosen extracts equivalent to one 96-well plate, and error bars represent the SD within the plate. Circled areas delineate marine extracts that change either the number of LDs per cell or nuclei per field relative to the normal range. (C) Schematic representation of the marine extracts processing protocol. Extract were initially partitioned between <i>n</i>-butanol and water. <i>n</i>-Butanol partitions identified as containing putative bioactive molecules were sequentially fractionated into hexane, dichloromethane or methanol, and individual fractions analysed for their effects on LD formation. Final resolution of the active components was achieved using HPLC-DAD-MS and NMR. (D) An <i>n</i>-butanol extract derived from a species of <i>Spongia (Heterofibria)</i> (designation CMB-03399) was fractionated as described in (C) and the effect of derived sub-fractions on LD formation analysed at different concentrations (n = 2 separate experiments, ± SD). DCM = dichloromethane, MeOH = methanol, <i>n</i>-but = <i>n</i>-butanol.</p>", "links"=>[], "tags"=>["heterofibrin"], "article_id"=>418798, "categories"=>["Biochemistry", "Chemistry", "Genetics"], "users"=>["James Rae", "Frank Fontaine", "Angela A. Salim", "Harriet P. Lo", "Robert J. Capon", "Robert G. Parton", "Sally Martin"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0022868.g002"], "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Extract_analysis_and_identification_of_heterofibrin_A1_/418798", "title"=>"Extract analysis and identification of heterofibrin A1.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-08-08 02:26:38"}
  • {"files"=>["https://ndownloader.figshare.com/files/748526"], "description"=>"<p>(A) A family of related diyne-ene fatty acids designated heterofibrin A1–A3 and B1–B3 were isolated from the hexane fraction of <i>Spongia (Heterofibria)</i> sp. A detailed structural analysis of the identification of the heterofibrin family of molecules is described in <a href=\"http://www.plosone.org/article/info:doi/10.1371/journal.pone.0022868#pone.0022868-Salim1\" target=\"_blank\">[15]</a>. (B) The activity of six heterofibrins on LD formation was analysed in A431 cells. Each heterofibrin was analysed across a range of concentrations. The highest levels of activity were associated with heterofibrins A1 and B1 (mean ± sem, n = 4 separate experiments). (C) The effect of heterofibrin A1 on cell viability was analysed by measuring LDH release. Cells were incubated for 16 h in control medium, DMSO, 50 µM oleic acid or varying concentrations of heterofibrin A1 (Hf-A1). At the end of the incubation period LDH activity in either the media or in solubilised whole cell lysates were measured according the manufacturers instructions (mean ± sem, n = 3 separate experiments).</p>", "links"=>[], "tags"=>["heterofibrins", "ld"], "article_id"=>418896, "categories"=>["Biochemistry", "Chemistry", "Genetics"], "users"=>["James Rae", "Frank Fontaine", "Angela A. Salim", "Harriet P. Lo", "Robert J. Capon", "Robert G. Parton", "Sally Martin"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0022868.g003"], "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Effect_of_heterofibrins_on_LD_formation_/418896", "title"=>"Effect of heterofibrins on LD formation.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-08-08 02:28:16"}
  • {"files"=>["https://ndownloader.figshare.com/files/748605"], "description"=>"<p>(A) AML12 hepatocytes were incubated overnight in delipidated FCS supplemented with either with 1 µM triacsin C or different concentrations of heterofibrin A1. Cells were subsequently treated with 50 µM oleic acid for 8 h. Control cells were incubated in delipidated FCS only. Cells were fixed and labelled for lipid droplets (Bodipy493/503, green) and nuclei (DAPI, blue). (B) Images of the fixed, labelled cells were analysed using the CellProfiler analysis pipeline and the number of LDs/cell quantified (mean ± sem, n = 3 separate experiments).</p>", "links"=>[], "tags"=>["a1", "inhibition", "ld", "biogenesis", "aml12"], "article_id"=>418970, "categories"=>["Biochemistry", "Chemistry", "Genetics"], "users"=>["James Rae", "Frank Fontaine", "Angela A. Salim", "Harriet P. Lo", "Robert J. Capon", "Robert G. Parton", "Sally Martin"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0022868.g004"], "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Heterofibrin_A1_inhibition_of_LD_biogenesis_in_AML12_hepatocytes_/418970", "title"=>"Heterofibrin A1 inhibition of LD biogenesis in AML12 hepatocytes.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-08-08 02:29:30"}
  • {"files"=>["https://ndownloader.figshare.com/files/748701"], "description"=>"<p>(A) A431 cells were incubated as follows: (1) delipidated FCS 16 h, 50 µM oleic acid 8 h, (2) delipidated FCS 24 h, (3) delipidated FCS containing 20 µM heterofibrin A1 16 h, 50 µM oleic acid 8 h. Neutral lipids were extracted and resolved by TLC. Results are shown for two independent sets of cells. Neutral Lipid Std = 45 µg lipid standard, Cholesterol Std = 10 µg free cholesterol. (B) The accumulation of TG was quantified using Image J. Results shown are relative to oleic acid (mean ± sem, n = 4 separate experiments). (C) A431 cells were incubated in delipidated FCS containing either 20 µM heterofibrin A1 or DMSO for 16 h. Cells were subsequently supplemented with 50 µM oleic acid containing 5 µCi [3H] oleic acid for 6 h. Neutral lipids were extracted and resolved by TLC. Results are shown for two independent sets of cells. Neutral Lipid Std = 45 µg lipid standard, Cholesterol Std = 10 µg free cholesterol.</p>", "links"=>[], "tags"=>["triglyceride", "a431"], "article_id"=>419071, "categories"=>["Biochemistry", "Chemistry", "Genetics"], "users"=>["James Rae", "Frank Fontaine", "Angela A. Salim", "Harriet P. Lo", "Robert J. Capon", "Robert G. Parton", "Sally Martin"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0022868.g005"], "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Quantification_of_triglyceride_in_A431_cells_/419071", "title"=>"Quantification of triglyceride in A431 cells.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-08-08 02:31:11"}
  • {"files"=>["https://ndownloader.figshare.com/files/748870"], "description"=>"<p>(A) Structure of Bodipy®558/568 C<sub>12</sub> (Invitrogen). (B) A431 cells were incubated in delipidated FCS (control) or 20 µM heterofibrin A1 overnight. Cells were subsequently incubated with 50 µM Bodipy558/568 C<sub>12</sub> for 30 min, fixed and cell nuclei labelled using DAPI. The accumulation of fatty acid within the cytoplasm of the cell was determined by Bodipy558/568 C<sub>12</sub> fluorescence. Cytoplasmic and nuclear imaging masks were generated using CellProfiler and used to determine the average cytoplasmic intensity of Bodipy558/568 C<sub>12</sub> fluorescence per cell. (C) The fluorescence intensity of cytoplasmic Bodipy558/568 C<sub>12</sub> was quantified at various times over a 60 min period (mean ± sem, n = 4 expts). (D) A431 cells were incubated overnight in delipidated FCS, heterofibrin A1 (Hf-A1, 20–50 µM) or triacsin C (TrC, 0.5–1 µM), then supplemented with 50 µM Bodipy558/568 C<sub>12</sub> for 2 h. Neutral lipids were extracted and resolved by TLC. Bodipy558/568 C<sub>12</sub> was detected using its intrinsic fluorescence and total lipids detected using primuline. Lanes are as follows: (1) Cells incubated in 50 µM Bodipy558/568 C<sub>12</sub> only for 2 h, (2) Control cells incubated in delipidated FCS only, (3) Bodipy558/568 C<sub>12</sub>, 24 µg, (4) cholesterol standard, 10 µg. Arrows indicate free cholesterol (FC) and free Bodipy558/568 C<sub>12</sub>. Arrowheads indicate Bodipy558/568 C<sub>12</sub> metabolites detected in the heterofibrin A1 treated cells only. Lower panels highlight regions of the TLC plate incorporating novel metabolites.</p>", "links"=>[], "tags"=>["fatty", "uptake", "metabolism", "a431"], "article_id"=>419238, "categories"=>["Biochemistry", "Chemistry", "Genetics"], "users"=>["James Rae", "Frank Fontaine", "Angela A. Salim", "Harriet P. Lo", "Robert J. Capon", "Robert G. Parton", "Sally Martin"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0022868.g006"], "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Fluorescent_fatty_acid_uptake_and_metabolism_in_A431_cells_/419238", "title"=>"Fluorescent fatty acid uptake and metabolism in A431 cells.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-08-08 02:33:58"}
  • {"files"=>["https://ndownloader.figshare.com/files/748988"], "description"=>"<p>A431 cells were incubated overnight in delipidated FCS supplemented with either heterofibrin A1 or known inhibitors of neutral lipid metabolic pathways, then supplemented with 50 µM Bodipy558/568 C<sub>12</sub> for 2 h (lanes 2–9). Neutral lipids were extracted and resolved by TLC. Bodipy558/568 C<sub>12</sub> was detected using its intrinsic fluorescence and total lipids detected using primuline. Lanes are as follows: (1) cholesterol standard, 10 µg, (2) 50 µM heterofibrin A1, (3) 20 µM heterofibrin A1, (4) 1 µM triacsin C, (5) 50 µM Orlistat, (6) 100 µM E600, (7) 600 µM 2-bromo octanoate, (8) Bodipy558/568 C<sub>12</sub> 2 h, (9) Control cells, (10) Bodipy558/568 C<sub>12</sub> control. Arrows (right) indicate free cholesterol (FC) and Bodipy558/568 C<sub>12</sub>. Arrowheads (left) indicate Bodipy558/568 C<sub>12</sub> metabolites detected in the heterofibrin A1 treated cells only. Lower panels highlight regions of the TLC plate incorporating novel metabolites following prolonged exposure.</p>", "links"=>[], "tags"=>["inhibitors", "lipolysis", "lipid", "synthesis", "fluorescent", "fatty", "heterofibrin"], "article_id"=>419349, "categories"=>["Biochemistry", "Chemistry", "Genetics"], "users"=>["James Rae", "Frank Fontaine", "Angela A. Salim", "Harriet P. Lo", "Robert J. Capon", "Robert G. Parton", "Sally Martin"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0022868.g007"], "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Effect_of_inhibitors_of_lipolysis_and_neutral_lipid_synthesis_on_fluorescent_fatty_acid_metabolism_comparison_to_heterofibrin_A1_/419349", "title"=>"Effect of inhibitors of lipolysis and neutral lipid synthesis on fluorescent fatty acid metabolism: comparison to heterofibrin A1.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-08-08 02:35:49"}
  • {"files"=>["https://ndownloader.figshare.com/files/749080"], "description"=>"<p>Zebrafish embryos (day 4–6 post-fertilisation) were incubated in the presence or absence of 10 µM heterofibrin A1 or 0.5 µM triacsin C for 2 h prior to the addition of Bodipy558/568 C<sub>12</sub> for 6 h. Control embryos were incubated with vehicle (DMSO) only. Embryos were subsequently processed for fluorescence microscopy or TLC. (A) Embryos were fixed and fluorescent fatty acid imaged using a stereo dissecting microscope. (B) Embryos were homogenised, neutral lipids extracted and resolved using TLC. Total lipids were visualised using primuline and metabolised Bodipy558/568 C<sub>12</sub> was detected by intrinsic fluorescence. The treatments were as follows: Lane 1, 0.5 µM triacsin C + Bodipy 558/568 C<sub>12</sub>; lane 2, 5 µM heterofibrin A1 + Bodipy 558/568 C<sub>12</sub>; lane 3, 10 µM heterofibrin A1 + Bodipy 558/568 C<sub>12</sub>; lane 4, Bodipy 558/568 C<sub>12</sub>; lane 5, DMSO + Bodipy 558/568 C<sub>12</sub>; lane 6 no treatment. Control lanes contained 65 µg heterofibrin A1, 10 µg cholesterol, 45 µg lipid standards and 24 µg Bodipy558/568 C<sub>12</sub>. Arrows delineate triglycerides (TG), free cholesterol (FC) and Bodipy558/568 C<sub>12</sub>. Arrowheads indicate Bodipy558/568 C<sub>12</sub> metabolites accumulated in embryos in the presence of heterofibrin A1. Lower panels highlight regions of the TLC plate incorporating novel metabolites.</p>", "links"=>[], "tags"=>["fluorescent", "fatty", "zebrafish"], "article_id"=>419455, "categories"=>["Biochemistry", "Chemistry", "Genetics"], "users"=>["James Rae", "Frank Fontaine", "Angela A. Salim", "Harriet P. Lo", "Robert J. Capon", "Robert G. Parton", "Sally Martin"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0022868.g008"], "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Metabolism_of_fluorescent_fatty_acid_in_zebrafish_embryos_/419455", "title"=>"Metabolism of fluorescent fatty acid in zebrafish embryos.", "pos_in_sequence"=>0, "defined_type"=>1, "published_date"=>"2011-08-08 02:37:35"}
  • {"files"=>["https://ndownloader.figshare.com/files/749165"], "description"=>"<p>nd = no detectable cytotoxicity at 50 µg/mL.</p>", "links"=>[], "tags"=>["sub-fractions", "derived", "subset", "inhibitory"], "article_id"=>419536, "categories"=>["Biochemistry", "Chemistry", "Genetics"], "users"=>["James Rae", "Frank Fontaine", "Angela A. Salim", "Harriet P. Lo", "Robert J. Capon", "Robert G. Parton", "Sally Martin"], "doi"=>["https://dx.doi.org/10.1371/journal.pone.0022868.t001"], "stats"=>{"downloads"=>0, "page_views"=>0, "likes"=>0}, "figshare_url"=>"https://figshare.com/articles/_Screening_of_sub_fractions_derived_from_a_subset_of_inhibitory_n_butanol_extracts_/419536", "title"=>"Screening of sub-fractions derived from a subset of inhibitory <i>n</i>-butanol extracts.", "pos_in_sequence"=>0, "defined_type"=>3, "published_date"=>"2011-08-08 02:38:56"}

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