Structure elucidation and synthesis of hydroxylated isatins from streptomycetes

Khaled A. Shaaban, Mohamed Shaaban, Vimal Nair, Imelda Schuhmann, Hnin Yu Win, Lei Lei, Birger Dittrich, Elisabeth Helmke, Anja Schüffler, Hartmut Laatsch

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Chemical investigation of terrestrial and marine streptomycete isolates led to the identification of two new natural pigments, namely, 6-hydroxyisatin (3) and 6-hydroxy-5-methoxyisatin (4). Additionally, the strains delivered numerous known compounds, among them Nβ-acetyltryptamine, N-acetyltyramine, phenylacetamide, N-(2-phenethyl)acetamide, 1-acetyl-β-carboline, tyrosol, 2'-deoxyadenosine, 2'-deoxythymidine, anthranilic acid, 2'-deoxyuridine, indolyl-3-acetic acid, indolyl-3-carboxylic acid, and p-hydroxybenzoic acid. The isatin structures were deduced by NMR and mass studies and further confirmed by synthesis and by X-ray diffraction of the isomeric 5-hydroxy-6-methoxyisatin (5).

Original languageEnglish
Pages (from-to)1191-1198
Number of pages8
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume71
Issue number12
DOIs
StatePublished - Dec 2016

Bibliographical note

Copyright:
Copyright 2021 Elsevier B.V., All rights reserved.

Keywords

  • Isatins
  • Natural pigments
  • Streptomycetes
  • Synthesis
  • X-ray diffraction

ASJC Scopus subject areas

  • Chemistry (all)

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