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  • 1990-1994  (2)
  • Antibacterial agents  (1)
  • Gabosine  (1)
  • 1
    ISSN: 0170-2041
    Schlagwort(e): Gabosine ; Metabolites, secondary ; Streptomyces ; Carba-sugar ; Chemical screening ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Chemical screening of different Streptomycetes strains resulted in the detection, isolation, and structure elucidation of a number of novel carba-sugars. The constitution of these secondary metabolites, named gabosines A to K (1 to 11), was deduced from spectroscopic data as well as chemical transformation reactions. The gabosines exhibit a basic C7 skeleton and can be characterized as hydroxylated branched cyclohexanone derivatives, which show structural similarities to carbohydrates deriving from secondary metabolism. The configuration fo the gabosines (absolute stereochemistry for 1, 4, 5, and 6; relative configuration for the remaining metabolites) was determined by derivatization with chiral acids (Helmchen's method), NMR spectral analysis, as well as by a comparison of optical rotation values with those of the already known gabosines B (2) and C (3). The new term “ketocarbasugars” is used to characterize a typical ketone containing subgroup of carba-sugars originating from microbial sources. The well available natural gabosines can be used as suitable chiral building blocks.
    Zusätzliches Material: 4 Tab.
    Materialart: Digitale Medien
    Bibliothek Standort Signatur Band/Heft/Jahr Verfügbarkeit
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  • 2
    ISSN: 0170-2041
    Schlagwort(e): Waraterpol ; Metabolites, secondary ; Penicillium ; Chemical screening ; Antibacterial agents ; Antifungal agents ; HIV ; Chemistry ; Organic Chemistry
    Quelle: Wiley InterScience Backfile Collection 1832-2000
    Thema: Chemie und Pharmazie
    Notizen: Substituted phenols can easily be recognized by using the chemical screening method, whereby they are found to be widely spread secondary metabolites of microorganisms. In the culture filtrate of Penicillium sp. (strain FH-A 6260) new phenols named waraterpols were detected by a striking purple coloration by using anisaldehyde/sulfuric acid. These secondary metabolites (1 to 3 and 6 to 8) exhibit a C15-carbon skeleton and can be characterized as hydroxylated branched-chain sesquiterpenoids with a benzoide moiety. The minor compounds were O-acetyl (2 and 3) and dehydrated derivatives (6 to 8) of the parent compound waraterpol (1), which was shown to be 6-[2-hydroxy-4-(hydroxymethyl)phenyl]-2-methylheptane-1,6-diol. Derivatization of 1 resulted in the quinone and hydroquinone compounds 10 and 5 as well as in the cyclic derivatives 11 and 12. The waraterpols exhibit distinct antibacterial and antifungal activities whereas an inhibition of HIV-1 in a MT-4 cell assay was found for 11.
    Zusätzliches Material: 1 Ill.
    Materialart: Digitale Medien
    Bibliothek Standort Signatur Band/Heft/Jahr Verfügbarkeit
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