Sulfadiazine Masquerading as a Natural Product from Scilla madeirensis (Scilloideae)
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Moodie, Lindon WK
Holland, Darren C
Jander, K Charlotte
Goransson, Ulf
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Abstract
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 α1-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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Journal of Natural Products
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83
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4
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© 2020 American Chemical Society and American Society of Pharmacognosy. This is an open access article published under a Creative Commons Attribution (CC-BY) License, which permits unrestricted use, distribution and reproduction in any medium, provided the author and source are cited.
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Chemical sciences
Biological sciences
Biomedical and clinical sciences
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Life Sciences & Biomedicine
Plant Sciences
Chemistry, Medicinal
Pharmacology & Pharmacy
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Robertson, LP; Moodie, LWK; Holland, DC; Jander, KC; Goransson, U, Sulfadiazine Masquerading as a Natural Product from Scilla madeirensis (Scilloideae), Journal of Natural Products, 2020, 83 (4), pp. 1305-1308