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Sulfadiazine Masquerading as a Natural Product from Scilla madeirensis (Scilloideae)

Authors
  • Robertson, Luke P.
  • Moodie, Lindon W. K.
  • Holland, Darren C.
  • Jandér, K. Charlotte
  • Göransson, Ulf
Publication Date
Jan 01, 2020
Identifiers
DOI: 10.1021/acs.jnatprod.0c00163
OAI: oai:DiVA.org:uu-418557
Source
DiVA - Academic Archive On-line
Keywords
Language
English
License
Green
External links

Abstract

The structure of 2,4-(4'-aminobenzenamine)pyrimidine (1), a pyrimidine alkaloid previously isolated from the bulbs of Scilla madeirensis (Asparagaceae, synonym Autonoe 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 alpha(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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