Literature DB >> 23463266

Conformational analysis of alternariol on the quantum level.

Olga Scharkoi1, Konstantin Fackeldey, Igor Merkulow, Karsten Andrae, Marcus Weber, Irene Nehls, David Siegel.   

Abstract

With the help of theoretical calculations we explain the phenomenon of nonplanarity of crystalline alternariol. We find out that the different orientations of the hydroxyl groups of alternariol influence its planarity and aromaticity and lead to different twists of the structure. The presence of the intramolecular hydrogen bond stabilizes the planar geometry while the loss of the bond results in a twist of over 14°. This effect is thought to be involved while cutting DNA strands by alternariol.

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Year:  2013        PMID： 23463266     DOI： 10.1007/s00894-013-1803-2

Source DB:  PubMed          Journal:  J Mol Model        ISSN： 0948-5023            Impact factor:   1.810


  9 in total

1.  Spherical aromaticity of fullerenes.

Authors:  M Bühl; A Hirsch
Journal:  Chem Rev       Date:  2001-05       Impact factor: 60.622

2.  Studies in the biochemistry of microorganisms. 90. Alternariol and alternariol monomethyl ether, metabolic products of Alternaria tenuis.

Authors:  H RAISTRICK; C E STICKINGS; R THOMAS
Journal:  Biochem J       Date:  1953-10       Impact factor: 3.857

3.  Domino reactions of 1,3-bis-silyl enol ethers with benzopyrylium triflates: efficient synthesis of fluorescent 6H-benzo[c]chromen-6-ones, dibenzo[c,d]chromen-6-ones, and 2,3-dihydro-1H-4,6-dioxachrysen-5-ones.

Authors:  Bettina Appel; Nehad N R Saleh; Peter Langer
Journal:  Chemistry       Date:  2006-01-23       Impact factor: 5.236

4.  Estrogenic and clastogenic potential of the mycotoxin alternariol in cultured mammalian cells.

Authors:  L Lehmann; J Wagner; M Metzler
Journal:  Food Chem Toxicol       Date:  2005-09-27       Impact factor: 6.023

5.  Analysis of agricultural commodities and foods for Alternaria mycotoxins.

Authors:  P M Scott
Journal:  J AOAC Int       Date:  2001 Nov-Dec       Impact factor: 1.913

6.  Alternariol.

Authors:  David Siegel; Sergey Troyanov; Johannes Noack; Franziska Emmerling; Irene Nehls
Journal:  Acta Crystallogr Sect E Struct Rep Online       Date:  2010-05-15

7.  Alternaria toxins: DNA strand-breaking activity in mammalian cellsin vitro.

Authors:  E Pfeiffer; S Eschbach; M Metzler
Journal:  Mycotoxin Res       Date:  2007-09       Impact factor: 3.833

8.  The mycotoxins alternariol and alternariol methyl ether negatively affect progesterone synthesis in porcine granulosa cells in vitro.

Authors:  U Tiemann; W Tomek; F Schneider; M Müller; R Pöhland; J Vanselow
Journal:  Toxicol Lett       Date:  2009-01-20       Impact factor: 4.372

9.  Alternariol acts as a topoisomerase poison, preferentially affecting the IIalpha isoform.

Authors:  Markus Fehr; Gudrun Pahlke; Jessica Fritz; Morten O Christensen; Fritz Boege; Martina Altemöller; Joachim Podlech; Doris Marko
Journal:  Mol Nutr Food Res       Date:  2009-04       Impact factor: 5.914
  9 in total
  1 in total

1.  Crystal Structure Determination and Hirshfeld Analysis of a New Alternariol Packing Polymorph.

Authors:  Kelly L Rue; Guodong Niu; Jun Li; Raphael G Raptis
Journal:  Crystals (Basel)       Date:  2022-04-21       Impact factor: 2.670
  1 in total

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