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Lars Porskjaer Christensen - One of the best experts on this subject based on the ideXlab platform.

  • Effect of the dietary polyacetylenes Falcarinol and falcarindiol on the gut microbiota composition in a rat model of colorectal cancer
    'Springer Science and Business Media LLC', 2018
    Co-Authors: Morten Kobaek-larsen, Lars Porskjaer Christensen, Dennis Sandris Nielsen, Witold Kot, Łukasz Krych, Gunnar Baatrup
    Abstract:

    Abstract Objectives (3R)-Falcarinol (FaOH) and (3R,8S)-falcarindiol (FaDOH) have previously been shown to reduce the number of neoplastic lesions and the growth rate of polyps in the colon of azoxymethane (AOM) treated rats. Based on previous investigations, it appears that different mechanisms of actions are involved in the antineoplastic effect of FaOH and FaDOH. One mechanism of action may be related to the antibacterial effect of FaOH and FaDOH and thus their effect on the gut microbiota. This study aimed to determine the effect of FaOH and FaDOH on gut microbiota composition of AOM treated rats. Results Azoxymethane treated rats were fed either a standard rat diet or a rat diet supplemented with FaOH and FaDOH. The gut microbiota of AOM-induced rats was determined by 16S rRNA gene-amplicon sequencing. Analysis of fecal cecum samples demonstrated a significant gut microbiota change in rats receiving standard rat diet supplemented with FaOH and FaDOH compared with the control group that only received the rat diet. Comparison of the gut microbiota of rats who developed large neoplasms in the colon with rats without large neoplasms showed that the gut microbiota was significantly different in rats who developed large colon neoplasms compared to rats with no macroscopic colon neoplasms

  • dietary polyacetylenes Falcarinol and falcarindiol isolated from carrots prevents the formation of neoplastic lesions in the colon of azoxymethane induced rats
    Food & Function, 2017
    Co-Authors: Xavier Frette, Lars Porskjaer Christensen, Morten Kobaeklarsen, Rime Bahij Elhouri, Issam Alnajami, Gunnar Baatrup
    Abstract:

    Falcarinol (FaOH) and falcarindiol (FaDOH) are found in many food plants of the Apiaceae family. Carrots are a major dietary source of these polyacetylenes. Feeding azoxymethane (AOM)-induced rats with carrots and purified FaOH have previously been shown to inhibit neoplastic transformations in the colon. FaOH and FaDOH have also shown to have a synergistic effect in vitro, resulting in a significant increased cytotoxic activity. Based on these findings the antineoplastic effect of FaOH and FaDOH (purity > 99%) was investigated in the AOM-induced rat model. Twenty rats received rat diet containing 7 μg FaOH per g feed and 7 μg FaDOH per g feed and 20 rats were controls receiving only rat diet. Then carcinogenesis was induced in all 40 rats with the carcinogen AOM. All animals received the designated diet for 2 weeks before AOM induction and continued on the designated diet throughout the experiment. Rats were euthanized 18 weeks after the first AOM injection and macroscopic polyp/cancers were measured, harvested and stained for histology. The difference in sizes of aberrant crypt foci (ACF) were analysed in a Wilcoxon rank sum test, in which the median number of small ACF was 218 in controls and 145 in polyacetylene treated rats (P < 0.001). Fifteen control rats and 8 treated rats had macroscopic tumors (P = 0.027). The number of tumors larger than 3 mm were 6 and 1 in control and treated rats, respectively (P = 0.032). In conclusion dietary supplements with FaOH and FaDOH reduced the number of neoplastic lesions as well as the growth rate of the polyps suggesting a preventive effect of FaOH and FaDOH on the development of colorectal cancer.

  • polyacetylenes from carrots daucus carota improve glucose uptake in vitro in adipocytes and myotubes
    Food & Function, 2015
    Co-Authors: Rime Bahij Elhouri, Dorota Kotowska, Kathrine Bisgaard Christensen, Sumangala Bhattacharya, Niels Oksbjerg, Gerhard Wolber, Karsten Kristiansen, Lars Porskjaer Christensen
    Abstract:

    A dichloromethane (DCM) extract of carrot roots was found to stimulate insulin-dependent glucose uptake (GU) in adipocytes in a dose dependent manner. Bioassay-guided fractionation of the DCM extract resulted in the isolation of the polyacetylenes Falcarinol and falcarindiol. Both polyacetylenes were able to significantly stimulate basal and/or insulin-dependent GU in 3T3-L1 adipocytes and porcine myotube cell cultures in a dose-dependent manner. Falcarindiol increased peroxisome proliferator-activated receptor (PPAR)γ-mediated transactivation significantly at concentrations of 3, 10 and 30 μM, while PPARγ-mediated transactivation by Falcarinol was only observed at 10 μM. Docking studies accordingly indicated that falcarindiol binds to the ligand binding domain of PPARγ with higher affinity than Falcarinol and that both polyacetylenes exhibit characteristics of PPARγ partial agonists. Falcarinol was shown to inhibit adipocyte differentiation as evident by gene expression studies and Oil Red O staining, whereas falcarindiol did not inhibit adipocyte differentiation, which indicates that these polyacetylenes have distinct modes of action. The results of the present study suggest that Falcarinol and falcarindiol may represent scaffolds for novel partial PPARγ agonists with possible antidiabetic properties.

  • Naringenin and Falcarinol stimulate glucose uptake and TBC1D1 phosphorylation in porcine myotube cultures
    2014
    Co-Authors: Sumangala Bhattacharya, Lars Porskjaer Christensen, Karsten Kristiansen, Martin Krøyer Rasmussen, Jette F. Young, Niels Oksbjerg
    Abstract:

    Insulin resistance in muscles is a major problem associated with Type 2 diabetes. Bioactive compounds of plant origin have long been known for possessing anti-diabetic properties. We have studied the effect of the bioactive compounds naringenin (dihydroflavonol) and Falcarinol (polyacetylene) on glucose uptake (GU) in normal and insulin resistant primary porcine myotubes, in the presence and absence of insulin to identify signaling pathways mediating their effects on GU. The dependence on glucose transporter type 4 (Glut4) activity, insulin signaling and AMP- activated protein kinase (AMPK)-signaling was studied by using the Glut4 inhibitor indinavir, the phosphatidyl inositol-3 kinase (PI3K) and p38 mitogen activated protein kinase (MAPK) inhibitor wortmannin, and the AMPK inhibitor dorsomorphin (DM), respectively. Naringenin and Falcarinol stimulated GU was attenuated in the presence of indinavir and wortmannin, indicating a dependence on Glut4 activity as well as PI3K and/or p38MAPK activity. By contrast, DM diminished GU induced by naringenin only, indicating that Falcarinol-stimulated GU was independent of AMPK activity. Finally, we show that naringenin and Falcarinol enhance phosphorylation of TBC1D1 suggesting that these compounds enhance translocation of Glut4 containing vesicles and thereby GU via a TBC1D1-dependent mechanism.

  • Systemic allergic dermatitis caused by Apiaceae root vegetables
    Contact Dermatitis, 2013
    Co-Authors: Evy Paulsen, Thomas H Petersen, Klaus Ejner Andersen, Xavier Frette, Lars Porskjaer Christensen
    Abstract:

    Summary Background. Immediate hypersensitivity reactions to root vegetables of the Umbelliferae plant family (Apiaceae) is well known. Delayed-type hypersensitivity is rarely reported. Objective. To report the first case of systemic contact dermatitis caused by root vegetables and some chemical implications. Materials and methods. Prick and patch testing were performed with fresh vegetables and selected allergens, and this was followed by high-performance liquid chromatography‐mass spectrometry (MS)/MS analysis of the Falcarinol syringe. Results. The patient was contact-sensitive to celeriac, parsnip, and carrot, but tested negative to Falcarinol. Subsequent analysis showed that the syringe contained Falcarinol. Conclusion. The non-occupational sensitization resulting from both direct and systemic contact with Apiaceae root vegetables was apparently not caused by Falcarinol.

Garth Loren Warnock - One of the best experts on this subject based on the ideXlab platform.

  • devil s club Falcarinol type polyacetylenes inhibit pancreatic cancer cell proliferation
    Nutrition and Cancer, 2019
    Co-Authors: Susan S C Cheung, Djamel Khelifi, Richard W Smith, David Hasman, Garth Loren Warnock
    Abstract:

    AbstractNatural Falcarinol-type (FC-type) polyacetylenes are known to show anticancer activities. We studied the bioactivity of synthetic FC, 1,2-dihydroFalcarinol (FCH) and 3-acetoxyFalcarinol (FCA) and compared them with the natural bioactive polyacetylene [9,17-octadecadiene-12,14-diyne-1,11,16-triol,1-acetate] (DCA) isolated from Devil’s club (DC) Oplopanax horridus. Antiproliferation activity of these polyacetylenes, along with DC inner stem bark 70% ethanol and water extracts, was tested on human pancreatic ductal adenocarcinoma cell lines PANC-1 and BxPC-3. Chemically synthesized FC and FCA showed consistent IC50 (50% inhibition concentration) and higher potency than DCA. FC and DCA’s mechanism of action investigated by antibody array on apoptosis-associated genes, and cellular features confirmed by microscopy demonstrated that both compounds modulated genes related to pro-apoptosis, antiapoptosis, apoptosis, cell cycle, stress related, and death receptors. FC-type polyacetylenes with a terminal do...

  • devil s club Falcarinol type polyacetylenes inhibit pancreatic cancer cell proliferation
    Nutrition and Cancer, 2019
    Co-Authors: Susan S C Cheung, Djamel Khelifi, Richard W Smith, David Hasman, Joseph Tai, Garth Loren Warnock
    Abstract:

    Natural Falcarinol-type (FC-type) polyacetylenes are known to show anticancer activities. We studied the bioactivity of synthetic FC, 1,2-dihydroFalcarinol (FCH) and 3-acetoxyFalcarinol (FCA) and compared them with the natural bioactive polyacetylene [9,17-octadecadiene-12,14-diyne-1,11,16-triol,1-acetate] (DCA) isolated from Devil's club (DC) Oplopanax horridus. Antiproliferation activity of these polyacetylenes, along with DC inner stem bark 70% ethanol and water extracts, was tested on human pancreatic ductal adenocarcinoma cell lines PANC-1 and BxPC-3. Chemically synthesized FC and FCA showed consistent IC50 (50% inhibition concentration) and higher potency than DCA. FC and DCA's mechanism of action investigated by antibody array on apoptosis-associated genes, and cellular features confirmed by microscopy demonstrated that both compounds modulated genes related to pro-apoptosis, antiapoptosis, apoptosis, cell cycle, stress related, and death receptors. FC-type polyacetylenes with a terminal double bond (FC, FCA, and DCA) are potent inhibitors of pancreatic cancer cell proliferation compared to FCH with a terminal single bond. Liquid chromatography mass spectrometry confirmed the presence of FC and FCH in the inner stem bark of DC. For potential applications of FC-type polyacetylenes as anticancer agents, preparing them by chemical synthesis may provide an advantage over the labor intensive extraction process from raw plant material.

Jess D Reed - One of the best experts on this subject based on the ideXlab platform.

  • purple carrot daucus carota l polyacetylenes decrease lipopolysaccharide induced expression of inflammatory proteins in macrophage and endothelial cells
    Journal of Agricultural and Food Chemistry, 2008
    Co-Authors: Brandon T Metzger, David M. Barnes, Jess D Reed
    Abstract:

    Carrots (Daucus carota L.) contain phytochemicals including carotenoids, phenolics, polyacetylenes, isocoumarins, and sesquiterpenes. Purple carrots also contain anthocyanins. The anti-inflammatory activity of extracts and phytochemicals from purple carrots was investigated by determining attenuation of the response to lipopolysaccharide (LPS). A bioactive chromatographic fraction (Sephadex LH-20) reduced LPS inflammatory response. There was a dose-dependent reduction in nitric oxide production and mRNA of pro-inflammatory cytokines (IL-6, IL-1β, TNF-α) and iNOS in macrophage cells. Protein secretions of IL-6 and TNF-α were reduced 77 and 66% in porcine aortic endothelial cells treated with 6.6 and 13.3 µg/mL of the LH-20 fraction, respectively. Preparative liquid chromatography resulted in a bioactive subfraction enriched in the polyacetylene compounds falcarindiol, falcarindiol 3-acetate, and Falcarinol. The polyacetylenes were isolated and reduced nitric oxide production in macrophage cells by as much ...

  • Purple carrot (Daucus carota L.) polyacetylenes decrease lipopolysaccharide-induced expression of inflammatory proteins in macrophage and endothelial cells.
    Journal of agricultural and food chemistry, 2008
    Co-Authors: Brandon T Metzger, David M. Barnes, Jess D Reed
    Abstract:

    Carrots ( Daucus carota L.) contain phytochemicals including carotenoids, phenolics, polyacetylenes, isocoumarins, and sesquiterpenes. Purple carrots also contain anthocyanins. The anti-inflammatory activity of extracts and phytochemicals from purple carrots was investigated by determining attenuation of the response to lipopolysaccharide (LPS). A bioactive chromatographic fraction (Sephadex LH-20) reduced LPS inflammatory response. There was a dose-dependent reduction in nitric oxide production and mRNA of pro-inflammatory cytokines (IL-6, IL-1beta, TNF-alpha) and iNOS in macrophage cells. Protein secretions of IL-6 and TNF-alpha were reduced 77 and 66% in porcine aortic endothelial cells treated with 6.6 and 13.3 microg/mL of the LH-20 fraction, respectively. Preparative liquid chromatography resulted in a bioactive subfraction enriched in the polyacetylene compounds falcarindiol, falcarindiol 3-acetate, and Falcarinol. The polyacetylenes were isolated and reduced nitric oxide production in macrophage cells by as much as 65% without cytotoxicity. These results suggest that polyacetylenes, not anthocyanins, in purple carrots are responsible for anti-inflammatory bioactivity.

Susan S C Cheung - One of the best experts on this subject based on the ideXlab platform.

  • devil s club Falcarinol type polyacetylenes inhibit pancreatic cancer cell proliferation
    Nutrition and Cancer, 2019
    Co-Authors: Susan S C Cheung, Djamel Khelifi, Richard W Smith, David Hasman, Garth Loren Warnock
    Abstract:

    AbstractNatural Falcarinol-type (FC-type) polyacetylenes are known to show anticancer activities. We studied the bioactivity of synthetic FC, 1,2-dihydroFalcarinol (FCH) and 3-acetoxyFalcarinol (FCA) and compared them with the natural bioactive polyacetylene [9,17-octadecadiene-12,14-diyne-1,11,16-triol,1-acetate] (DCA) isolated from Devil’s club (DC) Oplopanax horridus. Antiproliferation activity of these polyacetylenes, along with DC inner stem bark 70% ethanol and water extracts, was tested on human pancreatic ductal adenocarcinoma cell lines PANC-1 and BxPC-3. Chemically synthesized FC and FCA showed consistent IC50 (50% inhibition concentration) and higher potency than DCA. FC and DCA’s mechanism of action investigated by antibody array on apoptosis-associated genes, and cellular features confirmed by microscopy demonstrated that both compounds modulated genes related to pro-apoptosis, antiapoptosis, apoptosis, cell cycle, stress related, and death receptors. FC-type polyacetylenes with a terminal do...

  • devil s club Falcarinol type polyacetylenes inhibit pancreatic cancer cell proliferation
    Nutrition and Cancer, 2019
    Co-Authors: Susan S C Cheung, Djamel Khelifi, Richard W Smith, David Hasman, Joseph Tai, Garth Loren Warnock
    Abstract:

    Natural Falcarinol-type (FC-type) polyacetylenes are known to show anticancer activities. We studied the bioactivity of synthetic FC, 1,2-dihydroFalcarinol (FCH) and 3-acetoxyFalcarinol (FCA) and compared them with the natural bioactive polyacetylene [9,17-octadecadiene-12,14-diyne-1,11,16-triol,1-acetate] (DCA) isolated from Devil's club (DC) Oplopanax horridus. Antiproliferation activity of these polyacetylenes, along with DC inner stem bark 70% ethanol and water extracts, was tested on human pancreatic ductal adenocarcinoma cell lines PANC-1 and BxPC-3. Chemically synthesized FC and FCA showed consistent IC50 (50% inhibition concentration) and higher potency than DCA. FC and DCA's mechanism of action investigated by antibody array on apoptosis-associated genes, and cellular features confirmed by microscopy demonstrated that both compounds modulated genes related to pro-apoptosis, antiapoptosis, apoptosis, cell cycle, stress related, and death receptors. FC-type polyacetylenes with a terminal double bond (FC, FCA, and DCA) are potent inhibitors of pancreatic cancer cell proliferation compared to FCH with a terminal single bond. Liquid chromatography mass spectrometry confirmed the presence of FC and FCH in the inner stem bark of DC. For potential applications of FC-type polyacetylenes as anticancer agents, preparing them by chemical synthesis may provide an advantage over the labor intensive extraction process from raw plant material.

Thomas Hofmann - One of the best experts on this subject based on the ideXlab platform.

  • bioactive c polyacetylenes in carrots daucus carota l current knowledge and future perspectives
    Journal of Agricultural and Food Chemistry, 2015
    Co-Authors: Corinna Dawid, Thomas Nothnagel, Frank Dunemann, Wilfried Schwab, Thomas Hofmann
    Abstract:

    C17-polyacetylenes (PAs) are a prominent group of oxylipins and are primarily produced by plants of the families Apiaceae, Araliaceae, and Asteraceae, respectively. Recent studies on the biological activity of polyacetylenes have indicated their potential to improve human health due to anticancer, antifungal, antibacterial, anti-inflammatory, and serotogenic effects. These findings suggest targeting vegetables with elevated levels of bisacetylenic oxylipins, such as Falcarinol, by breeding studies. Due to the abundant availability, high diversity of cultivars, worldwide experience, and high agricultural yields, in particular, carrot (Daucus carota L.) genotypes are a very promising target vegetable. This paper provides a review on Falcarinol-type C17-polyacetylenes in carrots and a perspective on their potential as a future contributor to improving human health and well-being.

  • bioactive c17 polyacetylenes in carrots daucus carota l current knowledge and future perspectives
    Journal of Agricultural and Food Chemistry, 2015
    Co-Authors: Corinna Dawid, Thomas Nothnagel, Frank Dunemann, Wilfried Schwab, Thomas Hofmann
    Abstract:

    C17-polyacetylenes (PAs) are a prominent group of oxylipins and are primarily produced by plants of the families Apiaceae, Araliaceae, and Asteraceae, respectively. Recent studies on the biological activity of polyacetylenes have indicated their potential to improve human health due to anticancer, antifungal, antibacterial, anti-inflammatory, and serotogenic effects. These findings suggest targeting vegetables with elevated levels of bisacetylenic oxylipins, such as Falcarinol, by breeding studies. Due to the abundant availability, high diversity of cultivars, worldwide experience, and high agricultural yields, in particular, carrot (Daucus carota L.) genotypes are a very promising target vegetable. This paper provides a review on Falcarinol-type C17-polyacetylenes in carrots and a perspective on their potential as a future contributor to improving human health and well-being.

  • Bioactive C17-Polyacetylenes in Carrots (Daucus carota L.): Current Knowledge and Future Perspectives
    2015
    Co-Authors: Corinna Dawid, Thomas Nothnagel, Frank Dunemann, Wilfried Schwab, Thomas Hofmann
    Abstract:

    C17-polyacetylenes (PAs) are a prominent group of oxylipins and are primarily produced by plants of the families Apiaceae, Araliaceae, and Asteraceae, respectively. Recent studies on the biological activity of polyacetylenes have indicated their potential to improve human health due to anticancer, antifungal, antibacterial, anti-inflammatory, and serotogenic effects. These findings suggest targeting vegetables with elevated levels of bisacetylenic oxylipins, such as Falcarinol, by breeding studies. Due to the abundant availability, high diversity of cultivars, worldwide experience, and high agricultural yields, in particular, carrot (Daucus carota L.) genotypes are a very promising target vegetable. This paper provides a review on Falcarinol-type C17-polyacetylenes in carrots and a perspective on their potential as a future contributor to improving human health and well-being

  • structure determination of bisacetylenic oxylipins in carrots daucus carota l and enantioselective synthesis of falcarindiol
    Journal of Agricultural and Food Chemistry, 2009
    Co-Authors: Ludger Schmiech, Carole Alayrac, Bernhard Witulski, Thomas Hofmann
    Abstract:

    Although bisacetylenic oxylipins have been demonstrated to exhibit diverse biological activities, the chemical structures of many representatives of this class of phytochemicals still remain elusive. As carrots play an important role in our daily diet and are known as a source of bisacetylenes, an extract made from Daucus carota L. was screened for bisacetylenic oxylipins, and, after isolation, their structures were determined by means of LC−MS and 1D/2D NMR spectroscopy. Besides the previously reported Falcarinol, falcarindiol, and falcarindiol 3-acetate, nine additional bisacetylenes were identified, among which six derivatives are reported for the first time in literature and three compounds were previously not identified in carrots. To determine the absolute stereochemistry of falcarindiol in carrots, the (3R,8R)-, (3R,8S)-, (3S,8R)-, and (3S,8S)-stereoisomers of falcarindiol were synthesized according to a novel 10-step total synthesis involving a Cadiot−Chodkiewicz cross-coupling reaction of (S)- an...

  • structural and sensory characterization of compounds contributing to the bitter off taste of carrots daucus carota l and carrot puree
    Journal of Agricultural and Food Chemistry, 2003
    Co-Authors: Andreas Czepa, Thomas Hofmann
    Abstract:

    Sequential application of solvent extraction, gel permeation chromatography, and HPLC in combination with taste dilution analyses revealed that not a sole compound but a multiplicity of bitter tastants contribute to the bitter off-taste of cold-stored carrots and commercial carrot puree, respectively. Among these bitter compounds, 3-methyl-6-methoxy-8-hydroxy-3,4-dihydroisocoumarin (6-methoxymellein), 5-hydroxy-7-methoxy-2-methylchromone (eugenin), 2,4,5-trimethoxybenzaldehyde (gazarin), (Z)-heptadeca-1,9-diene-4,6-diin-3,8-diol (falcarindiol), (Z)-heptadeca-1,9-diene-4,6-diin-3-ol (Falcarinol), and (Z)-3-acetoxy-heptadeca-1,9-diene-4,6-diin-8-ol (falcarindiol 3-acetate) could be identified on the basis of MS as well as 1D- and 2D-NMR experiments. Due to the low concentrations of <0.1 mg/kg and the high taste thresholds found for eugenin and gazarin, these compounds could be unequivocally excluded as important contributors to the bitter taste of carrots. Calculation of bitter activity values as the ratio ...