Detection of a Toxic Methylated Derivative of Phomopsin A Produced by the Legume-Infesting Fungus Diaporthe toxica

Phomopsin A (PHO-A), produced by the fungus Diaporthe toxica, is a mycotoxin known to be responsible for fatal liver disease of lupin-fed sheep. The full spectrum of the toxic secondary metabolites produced by D. toxica is still unknown. PHO-A and the naturally occurring derivatives B–E have been su...

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Published inJournal of natural products (Washington, D.C.) Vol. 80; no. 6; pp. 1930 - 1934
Main Authors Schloß, Svenja, Hackl, Thomas, Herz, Corinna, Lamy, Evelyn, Koch, Matthias, Rohn, Sascha, Maul, Ronald
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society and American Society of Pharmacognosy 23.06.2017
Amer Chemical Soc
Subjects
Animals
Ascomycota - chemistry
Chemistry, Medicinal
cytotoxicity
Diaporthe
Fabaceae - microbiology
fungi
Hep G2 Cells - drug effects
human cell lines
Humans
Life Sciences & Biomedicine
liver diseases
Lupinus
Molecular Structure
mycotoxins
Mycotoxins - analysis
Mycotoxins - chemistry
nuclear magnetic resonance spectroscopy
Nuclear Magnetic Resonance, Biomolecular
Pharmacology & Pharmacy
Plant Sciences
Science & Technology
secondary metabolites
seeds
Seeds - chemistry
Sheep
HEXAPEPTIDE MYCOTOXIN
LUPIN
LEPTOSTROMIFORMIS
STRUCTURE ELUCIDATION
LC-MS/MS METHOD
FOOD
Online AccessGet full text
ISSN0163-3864
1520-6025
1520-6025
DOI10.1021/acs.jnatprod.6b00662

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Abstract Phomopsin A (PHO-A), produced by the fungus Diaporthe toxica, is a mycotoxin known to be responsible for fatal liver disease of lupin-fed sheep. The full spectrum of the toxic secondary metabolites produced by D. toxica is still unknown. PHO-A and the naturally occurring derivatives B–E have been subject to several studies to reveal their structures as well as chemical and toxicological properties. In this work, a methylated derivative (1) of PHO-A isolated from lupin seeds inoculated with D. toxica is described. It was characterized by high-resolution mass and NMR data and shown to be the N-methylated derivative of PHO-A. 1 is cytotoxic against HepG2 cells.
AbstractList Phomopsin A (PHO-A), produced by the fungus Diaporthe toxica, is a mycotoxin known to be responsible for fatal liver disease of lupin-fed sheep. The full spectrum of the toxic secondary metabolites produced by D. toxica is still unknown. PHO-A and the naturally occurring derivatives B-E have been subject to several studies to reveal their structures as well as chemical and toxicological properties. In this work, a methylated derivative (1) of PHO-A isolated from lupin seeds inoculated with D. toxica is described. It was characterized by high-resolution mass and NMR data and shown to be the N-methylated derivative of PHO-A. 1 is cytotoxic against HepG2 cells.Phomopsin A (PHO-A), produced by the fungus Diaporthe toxica, is a mycotoxin known to be responsible for fatal liver disease of lupin-fed sheep. The full spectrum of the toxic secondary metabolites produced by D. toxica is still unknown. PHO-A and the naturally occurring derivatives B-E have been subject to several studies to reveal their structures as well as chemical and toxicological properties. In this work, a methylated derivative (1) of PHO-A isolated from lupin seeds inoculated with D. toxica is described. It was characterized by high-resolution mass and NMR data and shown to be the N-methylated derivative of PHO-A. 1 is cytotoxic against HepG2 cells.
Phomopsin A (PHO-A), produced by the fungus Diaporthe toxica, is a mycotoxin known to be responsible for fatal liver disease of lupin-fed sheep. The full spectrum of the toxic secondary metabolites produced by D. toxica is still unknown. PHO-A and the naturally occurring derivatives B-E have been subject to several studies to reveal their structures as well as chemical and toxicological properties. In this work, a methylated derivative (1) of PHO-A isolated from lupin seeds inoculated with D. toxica is described. It was characterized by high-resolution mass and NMR data and shown to be the N-methylated derivative of PHO-A. 1 is cytotoxic against HepG2 cells.
Phomopsin A (PHO-A), produced by the fungus Diaporthe toxica, is a mycotoxin known to be responsible for fatal liver disease of lupin-fed sheep. The full spectrum of the toxic secondary metabolites produced by D. toxica is still unknown. PHO-A and the naturally occurring derivatives B–E have been subject to several studies to reveal their structures as well as chemical and toxicological properties. In this work, a methylated derivative (1) of PHO-A isolated from lupin seeds inoculated with D. toxica is described. It was characterized by high-resolution mass and NMR data and shown to be the N-methylated derivative of PHO-A. 1 is cytotoxic against HepG2 cells.
Author Schloß, Svenja
Herz, Corinna
Rohn, Sascha
Hackl, Thomas
Lamy, Evelyn
Maul, Ronald
Koch, Matthias
AuthorAffiliation NMR Facility, Department of Chemistry
Institute for Prevention and Cancer Epidemiology, Molecular Preventive Medicine
University of Freiburg−Medical Center
Hamburg School of Food Science, Institute of Food Chemistry
Department 1, Analytical Chemistry; Reference Materials
University of Hamburg
Bundesanstalt für Materialforschung und -prüfung (BAM)
AuthorAffiliation_xml – name: Institute for Prevention and Cancer Epidemiology, Molecular Preventive Medicine
– name: Hamburg School of Food Science, Institute of Food Chemistry
– name: University of Hamburg
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Keywords HEXAPEPTIDE MYCOTOXIN
LUPIN
LEPTOSTROMIFORMIS
STRUCTURE ELUCIDATION
LC-MS/MS METHOD
FOOD
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Snippet Phomopsin A (PHO-A), produced by the fungus Diaporthe toxica, is a mycotoxin known to be responsible for fatal liver disease of lupin-fed sheep. The full...
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StartPage 1930
SubjectTerms Animals
Ascomycota - chemistry
Chemistry, Medicinal
cytotoxicity
Diaporthe
Fabaceae - microbiology
fungi
Hep G2 Cells - drug effects
human cell lines
Humans
Life Sciences & Biomedicine
liver diseases
Lupinus
Molecular Structure
mycotoxins
Mycotoxins - analysis
Mycotoxins - chemistry
nuclear magnetic resonance spectroscopy
Nuclear Magnetic Resonance, Biomolecular
Pharmacology & Pharmacy
Plant Sciences
Science & Technology
secondary metabolites
seeds
Seeds - chemistry
Sheep
Title Detection of a Toxic Methylated Derivative of Phomopsin A Produced by the Legume-Infesting Fungus Diaporthe toxica
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Volume 80
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