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Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate
The title compound (systematic name: 3,7-dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one dimethyl sulfoxide monosolvate), C(15)H(12)O(5)·C(2)H(6)OS, was isolated from an unidentified endophytic fungus (belonging to class Ascomycetes) of Taxus sp. In the crystal, both the alternariol 9-O-meth...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
International Union of Crystallography
2013
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685032/ https://www.ncbi.nlm.nih.gov/pubmed/23795051 http://dx.doi.org/10.1107/S1600536813012294 |
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author | Dasari, Sreekanth Miller, Kristin I. Kalaitzis, John A. Bhadbhade, Mohan Neilan, Brett A. |
author_facet | Dasari, Sreekanth Miller, Kristin I. Kalaitzis, John A. Bhadbhade, Mohan Neilan, Brett A. |
author_sort | Dasari, Sreekanth |
collection | PubMed |
description | The title compound (systematic name: 3,7-dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one dimethyl sulfoxide monosolvate), C(15)H(12)O(5)·C(2)H(6)OS, was isolated from an unidentified endophytic fungus (belonging to class Ascomycetes) of Taxus sp. In the crystal, both the alternariol 9-O-methyl ether (AME) and the dimethyl sulfoxide (DMSO) molecules exhibit crystallographic mirror symmetry. One of the hydroxy groups makes bifurcated hydrogen bonds, viz. an intramolecular bond with the carbonyl group and an intermolecular bond with the carbonyl group in an inversion-related AME molecule. In the crystal, the AME molecules are organized into stacks parallel with the b axis by π–π interactions between centrosymmetrically related molecules [the distance between the centroid of the central ring and the centroid of the methoxy-substituted benzene ring in the next molecule of the stack is 3.6184 (5) Å]. Pairs of DMSO molecules, linked via centrosymmetric C—H⋯O contacts, are inserted into the voids created by the AME molecules, making O—H⋯O and C—H⋯O contacts with the hosts. |
format | Online Article Text |
id | pubmed-3685032 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2013 |
publisher | International Union of Crystallography |
record_format | MEDLINE/PubMed |
spelling | pubmed-36850322013-06-21 Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate Dasari, Sreekanth Miller, Kristin I. Kalaitzis, John A. Bhadbhade, Mohan Neilan, Brett A. Acta Crystallogr Sect E Struct Rep Online Organic Papers The title compound (systematic name: 3,7-dihydroxy-9-methoxy-1-methyl-6H-benzo[c]chromen-6-one dimethyl sulfoxide monosolvate), C(15)H(12)O(5)·C(2)H(6)OS, was isolated from an unidentified endophytic fungus (belonging to class Ascomycetes) of Taxus sp. In the crystal, both the alternariol 9-O-methyl ether (AME) and the dimethyl sulfoxide (DMSO) molecules exhibit crystallographic mirror symmetry. One of the hydroxy groups makes bifurcated hydrogen bonds, viz. an intramolecular bond with the carbonyl group and an intermolecular bond with the carbonyl group in an inversion-related AME molecule. In the crystal, the AME molecules are organized into stacks parallel with the b axis by π–π interactions between centrosymmetrically related molecules [the distance between the centroid of the central ring and the centroid of the methoxy-substituted benzene ring in the next molecule of the stack is 3.6184 (5) Å]. Pairs of DMSO molecules, linked via centrosymmetric C—H⋯O contacts, are inserted into the voids created by the AME molecules, making O—H⋯O and C—H⋯O contacts with the hosts. International Union of Crystallography 2013-05-11 /pmc/articles/PMC3685032/ /pubmed/23795051 http://dx.doi.org/10.1107/S1600536813012294 Text en © Dasari et al. 2013 http://creativecommons.org/licenses/by/2.0/uk/ This is an open-access article distributed under the terms of the Creative Commons Attribution Licence, which permits unrestricted use, distribution, and reproduction in any medium, provided the original authors and source are cited. |
spellingShingle | Organic Papers Dasari, Sreekanth Miller, Kristin I. Kalaitzis, John A. Bhadbhade, Mohan Neilan, Brett A. Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate |
title | Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate |
title_full | Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate |
title_fullStr | Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate |
title_full_unstemmed | Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate |
title_short | Alternariol 9-O-methyl ether dimethyl sulfoxide monosolvate |
title_sort | alternariol 9-o-methyl ether dimethyl sulfoxide monosolvate |
topic | Organic Papers |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3685032/ https://www.ncbi.nlm.nih.gov/pubmed/23795051 http://dx.doi.org/10.1107/S1600536813012294 |
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