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Sulfadiazine Masquerading as a Natural Product from Scilla madeirensis (Scilloideae)
[Image: see text] The structure of 2,4-(4′-aminobenzenamine)pyrimidine (1), a pyrimidine alkaloid previously isolated from the bulbs of Scilla madeirensis (Asparagaceae, synonym Autonoë madeirensis), has been revised. These conclusions were met via comparison of reported NMR and EIMS data with those...
Autores principales: | , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
American Chemical
Society and American
Society of Pharmacognosy
2020
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Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7307949/ https://www.ncbi.nlm.nih.gov/pubmed/32208615 http://dx.doi.org/10.1021/acs.jnatprod.0c00163 |
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author | Robertson, Luke P. Moodie, Lindon W. K. Holland, Darren C. Jandér, K. Charlotte Göransson, Ulf |
author_facet | Robertson, Luke P. Moodie, Lindon W. K. Holland, Darren C. Jandér, K. Charlotte Göransson, Ulf |
author_sort | Robertson, Luke P. |
collection | PubMed |
description | [Image: see text] The structure of 2,4-(4′-aminobenzenamine)pyrimidine (1), a pyrimidine alkaloid previously isolated from the bulbs of Scilla madeirensis (Asparagaceae, synonym Autonoë madeirensis), has been revised. These conclusions were met via comparison of reported NMR and EIMS data with those obtained from synthetic standards. The corrected structure is the antibiotic sulfadiazine (2), which has likely been isolated as a contaminant from the site of collection. The reported bioactivity of 1 as an α(1)-adrenoceptor antagonist should instead be ascribed to sulfadiazine. Our findings appear to show another example of an anthropogenic contaminant being identified as a natural product and emphasize the importance of considering the biosynthetic origins of isolated compounds within a phylogenetic context. |
format | Online Article Text |
id | pubmed-7307949 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2020 |
publisher | American Chemical
Society and American
Society of Pharmacognosy |
record_format | MEDLINE/PubMed |
spelling | pubmed-73079492020-06-23 Sulfadiazine Masquerading as a Natural Product from Scilla madeirensis (Scilloideae) Robertson, Luke P. Moodie, Lindon W. K. Holland, Darren C. Jandér, K. Charlotte Göransson, Ulf J Nat Prod [Image: see text] The structure of 2,4-(4′-aminobenzenamine)pyrimidine (1), a pyrimidine alkaloid previously isolated from the bulbs of Scilla madeirensis (Asparagaceae, synonym Autonoë madeirensis), has been revised. These conclusions were met via comparison of reported NMR and EIMS data with those obtained from synthetic standards. The corrected structure is the antibiotic sulfadiazine (2), which has likely been isolated as a contaminant from the site of collection. The reported bioactivity of 1 as an α(1)-adrenoceptor antagonist should instead be ascribed to sulfadiazine. Our findings appear to show another example of an anthropogenic contaminant being identified as a natural product and emphasize the importance of considering the biosynthetic origins of isolated compounds within a phylogenetic context. American Chemical Society and American Society of Pharmacognosy 2020-03-25 2020-04-24 /pmc/articles/PMC7307949/ /pubmed/32208615 http://dx.doi.org/10.1021/acs.jnatprod.0c00163 Text en Copyright © 2020 American Chemical Society and American Society of Pharmacognosy This is an open access article published under a Creative Commons Attribution (CC-BY) License (http://pubs.acs.org/page/policy/authorchoice_ccby_termsofuse.html) , which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited. |
spellingShingle | Robertson, Luke P. Moodie, Lindon W. K. Holland, Darren C. Jandér, K. Charlotte Göransson, Ulf Sulfadiazine Masquerading as a Natural Product from Scilla madeirensis (Scilloideae) |
title | Sulfadiazine Masquerading as a Natural Product from Scilla
madeirensis (Scilloideae) |
title_full | Sulfadiazine Masquerading as a Natural Product from Scilla
madeirensis (Scilloideae) |
title_fullStr | Sulfadiazine Masquerading as a Natural Product from Scilla
madeirensis (Scilloideae) |
title_full_unstemmed | Sulfadiazine Masquerading as a Natural Product from Scilla
madeirensis (Scilloideae) |
title_short | Sulfadiazine Masquerading as a Natural Product from Scilla
madeirensis (Scilloideae) |
title_sort | sulfadiazine masquerading as a natural product from scilla
madeirensis (scilloideae) |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7307949/ https://www.ncbi.nlm.nih.gov/pubmed/32208615 http://dx.doi.org/10.1021/acs.jnatprod.0c00163 |
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