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Sulfadiazine Masquerading as a Natural Product from Scilla madeirensis (Scilloideae)
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Genetics, Plant Ecology and Evolution. Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Pharmaceutical Biosciences.ORCID iD: 0000-0001-5987-2426
Uppsala University, Disciplinary Domain of Medicine and Pharmacy, Faculty of Pharmacy, Department of Medicinal Chemistry, Drug Design and Discovery.ORCID iD: 0000-0002-9500-4535
Griffith Univ, Environm Futures Res Inst, Gold Coast 4222, Australia;..ORCID iD: 0000-0002-2498-6084
Uppsala University, Disciplinary Domain of Science and Technology, Biology, Department of Ecology and Genetics, Plant Ecology and Evolution.ORCID iD: 0000-0002-0449-7814
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2020 (English)In: Journal of Natural Products, ISSN 0163-3864, E-ISSN 1520-6025, Vol. 83, no 4, p. 1305-1308Article in journal (Refereed) Published
Abstract [en]

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.

Place, publisher, year, edition, pages
AMER CHEMICAL SOC , 2020. Vol. 83, no 4, p. 1305-1308
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Organic Chemistry
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URN: urn:nbn:se:uu:diva-418557DOI: 10.1021/acs.jnatprod.0c00163ISI: 000529168400054PubMedID: 32208615OAI: oai:DiVA.org:uu-418557DiVA, id: diva2:1464331
Available from: 2020-09-04 Created: 2020-09-04 Last updated: 2020-10-02Bibliographically approved

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Robertson, Luke P.Moodie, Lindon W. K.Jandér, K. CharlotteGöransson, Ulf

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Robertson, Luke P.Moodie, Lindon W. K.Holland, Darren C.Jandér, K. CharlotteGöransson, Ulf
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Plant Ecology and EvolutionDepartment of Pharmaceutical BiosciencesDrug Design and DiscoveryFarmakognosi
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