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  • 1
    Electronic Resource
    Electronic Resource
    Structure and Biosynthesis of Mutolide, a Novel Macrolide from a UV Mutant of the Fungus F-24′707 (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1451-1456 
    Details
    ISSN: 1434-193X
    Keywords: Mutolide ; Metabolites, secondary ; Macrolide ; Chemical screening ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---The 14-membered macrolide, mutolide (1), was discovered by chemical screening of the culture broth of the fungus F-24′707y, obtained after UV mutagenesis of the wild type strain, which normally produces the spirobisnaphthalene cladospirone bisepoxide (2). The structure of 1 was established by detailed spectroscopic analysis, X-ray analysis and derivatisation. The biogenetic origin of the carbon skeleton and the hydroxy groups was verified by feeding sodium [1-13C]acetate and 18O2 to growing cultures of the fungus. Macrolide 1 is generated from acetate/malonate only. The unexpected change of the normal metabolite pattern of this strain is discussed, and proves the value of the OSMAC method.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    Gabosines L, N and O: New Carba-Sugars from Streptomyces with DNA-Binding Properties (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 149-153 
    Details
    ISSN: 1434-193X
    Keywords: Gabosine ; Secondary metabolite ; Carbohydrates ; Chemical screening ; Biomolecular-chemical screening ; DNA binding ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---In addition to the known gabosines A (4), B (5) and C (6), three new gabosines L (1), N (2) and O (3) were detected by chemical screening as secondary metabolites of Streptomyces (strains GT 041230, GT 051024 and S 1096). The constitutions of 1, 2 and 3 were established by spectroscopic techniques and derivatization reactions. The absolute stereochemistry of 1 and 2 was determined by Helmchen's method and has been verified in the case of gabosine N (2) by X-ray analysis. The DNA-binding properties of the gabosines were investigated and analyzed by binding studies using a recently developed thin-layer chromatography technique (bimolecular-chemical screening).
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Secondary Metabolites by Chemical Screening, 36Part 35. Ref.[1].. Ulupyrinone and Ulufuranol: New Heteroaromatic Metabolites from Streptomyces spina (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 937-939 
    Details
    ISSN: 0947-3440
    Keywords: Ulupyrinone ; Ulufuranol ; Metabolism ; Chemical screening ; Streptomyces ; Structure elucidation ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Chemical Screening with extracts of Actinomycetes strains resulted in the detection, isolation, and structural elucidation of two new heteroaromatic secondary metabolites, named ulupyrinone (1) and ulufuranol (2), from Streptomyces spina (strain FH-S 2144). The absolute configuration of ulufuranol (2) was determined by analysis of the CD spectra of its dibenzoate, 3, using the dibenzoate chirality rule.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970523
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  • 4
    Electronic Resource
    Electronic Resource
    Secondary metabolites by chemical screening, 10. Glycerinopyrin, a novel metabolite from Streptomyces violaceus (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 77-80 
    Details
    ISSN: 0170-2041
    Keywords: Streptomyces violaceus ; Chemical screening ; 2-Pyrrolecarboxylic acid derivatives ; Glycerol ester, NMR assignments ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Glycerinopyrin (1) was detected by chemical screening as a new metabolite from Streptomyces violaceus. Its structure was elucidated by chemical and spectroscopical methods as (2S)- 2,3-dihydroxypropyl 1-hydroxy-4-methyl-2-pyrrolecarboxylate.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199119910114
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  • 5
    Electronic Resource
    Electronic Resource
    Secondary Metabolites by Chemical Screening, 22. Gabosines, New Carba-sugars From Streptomyces (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 241-250 
    Details
    ISSN: 0170-2041
    Keywords: Gabosine ; Metabolites, secondary ; Streptomyces ; Carba-sugar ; Chemical screening ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 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.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930143
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  • 6
    Electronic Resource
    Electronic Resource
    Secondary Metabolites by Chemical Screening, 28. Aspinonene, a New Multifunctional Fungal Metabolite (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 831-835 
    Details
    ISSN: 0170-2041
    Keywords: Aspinonene ; Fungal metabolites ; Aspergillus ; Chemical screening ; Epoxides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A new C9 epoxide named aspinonene (1) was found by chemical screening in the culture broth of Aspergillus ochraceus (strain FH-A 6692). Its structure was deduced from spectroscopic data as well as from an X-ray analysis of the dibromobenzoate of 1. The configuration of C-2 was further verified by esterification of the ketone 4 with chiral acids (Helmchen's method). The reactivity of the functional groups was studied by acylation, silylation, ketalization, and oxidation. Due to the diversity of its functional groups and the neighbouring centres of chirality 1 is discussed as a secondary metabolite suited as a building block for synthesis.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940812
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  • 7
    Electronic Resource
    Electronic Resource
    Secondary Metabolites by Chemical Screening, 24. Oasomycins, New Macrolactones of the Desertomycin Family (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 573-579 
    Details
    ISSN: 0170-2041
    Keywords: Oasomycin ; Metabolites, secondary ; Macrolactone ; Desertomycin ; Chemical screening ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: New macrolactones, named oasomycin A to D (1 to 4), were discovered by a chemical screening in the culture broth of Streptoverticillium baldacii subsp. netropse (strain FH-S 1625). The structures were established by detailed spectroscopic analysis. The fundamental 42-membered lactone moiety of oasomycin A and B (1 and 2) is analogous to that of desertomycin A (5), while the oasomycins C and D (3 and 4) are the first representatives of macrolactones bearing a 44-membered skeleton. These metabolites can be distinguished by side chain modifications at C-41 or C-43 as well as the presence of an α-linked D-mannose moiety attached to 22-OH. Due to the structural similarities the oasomycins are integrated into the desertomycin family. In vitro testing by using the HEP-G2 cell assay showed oasomycin A (1) to be an inhibitor of de novo cholesterol biosynthesis.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930193
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  • 8
    Electronic Resource
    Electronic Resource
    Secondary Metabolites by Chemical Screening, 23. Waraterpols, New Penicillium Metabolites and Their Derivatives (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 565-571 
    Details
    ISSN: 0170-2041
    Keywords: Waraterpol ; Metabolites, secondary ; Penicillium ; Chemical screening ; Antibacterial agents ; Antifungal agents ; HIV ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 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.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930192
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