Isolation and Structure Elucidation of Pentahydroxyscirpene, a Trichothecene Fusarium Mycotoxin
Pentahydroxyscirpene, a novel trichothecene-type compound, was isolated from Fusarium-inoculated rice. The structure of pentahydroxyscirpene was elucidated by 1D and 2D NMR spectroscopy and X-ray single-crystal diffraction. The conformation in solution was determined by NOESY experiments supported b...
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| Published in | Journal of natural products (Washington, D.C.) Vol. 77; no. 1; pp. 188 - 192 |
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| Main Authors | , , , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
WASHINGTON
American Chemical Society and American Society of Pharmacognosy
24.01.2014
Amer Chemical Soc |
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| Abstract | Pentahydroxyscirpene, a novel trichothecene-type compound, was isolated from Fusarium-inoculated rice. The structure of pentahydroxyscirpene was elucidated by 1D and 2D NMR spectroscopy and X-ray single-crystal diffraction. The conformation in solution was determined by NOESY experiments supported by quantum chemical calculations. In vitro toxicity tests showed that pentahydroxyscirpene inhibits protein synthesis as do other trichothecenes. |
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| AbstractList | Pentahydroxyscirpene, a novel trichothecene-type compound, was isolated from Fusarium-inoculated rice. The structure of pentahydroxyscirpene was elucidated by 1D and 2D NMR spectroscopy and X-ray single-crystal diffraction. The conformation in solution was determined by NOESY experiments supported by quantum chemical calculations. In vitro toxicity tests showed that pentahydroxyscirpene inhibits protein synthesis as do other trichothecenes. Pentahydroxyscirpene, a novel trichothecene-type compound, was isolated from Fusarium -inoculated rice. The structure of pentahydroxyscirpene was elucidated by 1D and 2D NMR spectroscopy and X-ray single-crystal diffraction. The conformation in solution was determined by NOESY experiments supported by quantum chemical calculations. In vitro toxicity tests showed that pentahydroxyscirpene inhibits protein synthesis as do other trichothecenes. |
| Author | Fröhlich, Johannes Lemmens, Marc Fruhmann, Philipp Berthiller, Franz Lumpi, Daniel Häubl, Georg Wiesenberger, Gerlinde Mikula, Hannes Adam, Gerhard Stöger, Berthold Hametner, Christian Krska, Rudolf Varga, Elisabeth |
| AuthorAffiliation | Institute of Chemical Technologies and Analytics Institute of Applied Synthetic Chemistry Department of Applied Genetics and Cell Biology Vienna University of Technology (VUT) University of Natural Resources and Life Sciences, Vienna (BOKU) Institute for Biotechnology in Plant Production, Department for Agrobiotechnology (IFA-Tulln) Christian Doppler Laboratory for Mycotoxin Metabolism and Center for Analytical Chemistry, Department for Agrobiotechnology (IFA-Tulln) Romer Laboratories Division Holding GmbH |
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| CitedBy_id | crossref_primary_10_1016_j_phytol_2016_08_017 crossref_primary_10_3389_fmicb_2016_00406 crossref_primary_10_3390_toxins8100295 crossref_primary_10_3390_toxins8120361 crossref_primary_10_1016_j_ijfoodmicro_2014_08_011 crossref_primary_10_1021_acs_jnatprod_8b00205 crossref_primary_10_3390_toxins6010325 crossref_primary_10_1055_a_1091_8831 crossref_primary_10_1002_hlca_201500182 crossref_primary_10_1016_j_jhazmat_2015_01_051 |
| Cites_doi | 10.1016/j.ijfoodmicro.2007.07.019 10.1007/s00216-005-3330-1 10.3390/toxins3070802 10.1107/S0021889807029238 10.1128/CMR.16.3.497-516.2003 10.1016/S0377-8401(98)00278-8 10.1016/S0377-8401(97)81630-6 10.1080/009841096161447 10.3109/10408448509089851 10.1016/0304-4165(87)90005-5 10.1021/ja01143a007 10.1016/S0076-6879(83)96008-1 10.1073/pnas.71.1.30 10.1039/C39780000601 |
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Chemical Society and American Society of Pharmacognosy Copyright © 2013 American Chemical Society and American Society of Pharmacognosy 2013 American Chemical Society and American Society of Pharmacognosy |
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| Snippet | Pentahydroxyscirpene, a novel trichothecene-type compound, was isolated from Fusarium-inoculated rice. The structure of pentahydroxyscirpene was elucidated by... Pentahydroxyscirpene, a novel trichothecene-type compound, was isolated from Fusarium -inoculated rice. The structure of pentahydroxyscirpene was elucidated by... |
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| SubjectTerms | Chemistry, Medicinal Crystallography, X-Ray Fusarium Fusarium - chemistry Life Sciences & Biomedicine Molecular Conformation Molecular Structure Mycotoxins - chemistry Mycotoxins - isolation & purification Mycotoxins - pharmacology Nuclear Magnetic Resonance, Biomolecular Oryza - microbiology Oryza sativa Pharmacology & Pharmacy Plant Sciences Protein Synthesis Inhibitors - chemistry Protein Synthesis Inhibitors - isolation & purification Protein Synthesis Inhibitors - pharmacology Science & Technology Trichothecenes - chemistry Trichothecenes - isolation & purification Trichothecenes - pharmacology |
| Title | Isolation and Structure Elucidation of Pentahydroxyscirpene, a Trichothecene Fusarium Mycotoxin |
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