Identification of Alternaria alternata Mycotoxins by LC-SPE-NMR and Their Cytotoxic Effects to Soybean (Glycine max) Cell Suspension Culture

被引:24
作者
de Souza, Gezimar D. [1 ,2 ,3 ]
Mithoefer, Axel [2 ]
Daolio, Cristina [4 ,5 ]
Schneider, Bernd [4 ]
Rodrigues-Filho, Edson [1 ]
机构
[1] Univ Fed Sao Carlos UFSCar, Lab Bioquim Micromol Microorganism, Dept Quim, Sao Carlos, SP, Brazil
[2] Max Planck Inst Chem Ecol, Dept Bioorgan Chem, D-07745 Jena, Germany
[3] Accert Chem & Biotechnol Inc, Sao Carlos, SP, Brazil
[4] Max Planck Inst Chem Ecol, Biosynth NMR Res Grp, D-07745 Jena, Germany
[5] Bruker Biospin GmbH, NMR Applicat Grp, D-76287 Rheinstetten, Germany
基金
巴西圣保罗研究基金会;
关键词
LC-NMR; LC-SPE-NMR; mass spectrometry; alternariol; Alternaria; soybean; Glycine max; cell cultures; cytotoxicity; NUCLEAR-MAGNETIC-RESONANCE; MASS-SPECTROMETRY; MONOMETHYL ETHER; BROWN SPOT; MAMMALIAN-CELLS; MUTAGENICITY; PRODUCTS; CITRUS; SPECTROSCOPY; HPLC;
D O I
10.3390/molecules18032528
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
This present work describes the application of liquid chromatograpy-solid phase extraction-nuclear magnetic resonance spectroscopy to analyse Alternaria alternata crude extracts. Altenusin (1), alternariol (2), 3'-hydroxyalternariol monomethyl ether (3), and alternariol monomethyl ether (4), were separated and identified. High-resolution mass spectrometry confirmed the proposed structures. The cytotoxic effects of these compounds towards plants were determined using soybean (Glycine max) cell cultures as a model. EC50 values which range from 0.11 (+/- 0.02) to 4.69 (+/- 0.47) mu M showed the high cytotoxicity of these compounds.
引用
收藏
页码:2528 / 2538
页数:11
相关论文
共 33 条
[1]   Determination of multi-mycotoxin occurrence in cereals, nuts and their products in Cameroon by liquid chromatography tandem mass spectrometry (LC-MS/MS) [J].
Abia, Wilfred A. ;
Warth, Benedikt ;
Sulyok, Michael ;
Krska, Rudolf ;
Tchana, Angele N. ;
Njobeh, Patrick B. ;
Dutton, Mike F. ;
Moundipa, Paul F. .
FOOD CONTROL, 2013, 31 (02) :438-453
[2]   Greenhouse evaluation of products that induce host resistance for control of scab, melanose, and Alternaria brown spot of citrus [J].
Agostini, JP ;
Bushong, PM ;
Timmer, LW .
PLANT DISEASE, 2003, 87 (01) :69-74
[3]  
Akimitsu KA, 2003, MOL PLANT PATHOL, V4, P435, DOI [10.1046/j.1364-3703.2003.00189.x, 10.1046/j.1364-3703.2003.00189.X]
[4]   Cytotoxic metabolites from the fungal endophyte Alternaria sp and their subsequent detection in its host plant Polygonum senegalense [J].
Aly, Amal H. ;
Edrada-Ebel, RuAngelie ;
Indriani, Ine Dewi ;
Wray, Victor ;
Mueller, Werner E. G. ;
Totzke, Frank ;
Zirrgiebel, Ute ;
Schaechtele, Christoph ;
Kubbutat, Michael H. G. ;
Lin, W. H. ;
Proksch, Peter ;
Ebel, Rainer .
JOURNAL OF NATURAL PRODUCTS, 2008, 71 (06) :972-980
[5]   ISOLATION, IDENTIFICATION, AND MUTAGENICITY OF ALTERNARIOL MONOMETHYL ETHER [J].
AN, YH ;
ZHAO, TZ ;
MIAO, J ;
LIU, GT ;
ZHENG, YZ ;
XU, YM ;
VANETTEN, RL .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1989, 37 (05) :1341-1343
[6]   Chemical and morphological segregation of Alternaria arborescens, A-infectoria and A-tenuissima species-groups [J].
Andersen, B ;
Kroger, E ;
Roberts, RG .
MYCOLOGICAL RESEARCH, 2002, 106 :170-182
[7]   Stable Isotope Dilution Assays of Alternariol and Alternariol Monomethyl Ether in Beverages [J].
Asam, Stefan ;
Konitzer, Katharina ;
Schieberle, Peter ;
Rychlik, Michael .
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2009, 57 (12) :5152-5160
[8]   5'-EPIALTENUENE AND NEOALTENUENE, DIBENZO-ALPHA-PYRONES FROM ALTERNARIA-ALTERNATA CULTURED ON RICE [J].
BRADBURN, N ;
COKER, RD ;
BLUNDEN, G ;
TURNER, CH ;
CRABB, TA .
PHYTOCHEMISTRY, 1994, 35 (03) :665-669
[9]   Mutagenicity of the mycotoxin alternariol in cultured mammalian cells [J].
Brugger, Eva-Maria ;
Wagner, Joerg ;
Schumacher, David M. ;
Koch, Karen ;
Podlech, Joachim ;
Metzler, Manfred ;
Lehmann, Leane .
TOXICOLOGY LETTERS, 2006, 164 (03) :221-230
[10]   Hyphenated chromatographic techniques for structural characterization and determination of masked mycotoxins [J].
Cirlini, M. ;
Dall'Asta, C. ;
Galaverna, G. .
JOURNAL OF CHROMATOGRAPHY A, 2012, 1255 :145-152