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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...

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Autores principales: Robertson, Luke P., Moodie, Lindon W. K., Holland, Darren C., Jandér, K. Charlotte, Göransson, Ulf
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society and American Society of Pharmacognosy 2020
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.
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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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