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  • 1
    Electronic Resource
    Electronic Resource
    Metabolic products of microorganisms, 271. Momofulvenone A and B, new benzo[b]fluorene quinones from Streptomyces (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1169-1172 
    Details
    ISSN: 0947-3440
    Keywords: Momofulvenone ; Metabolites, secondary ; Benzo[b]fluorene quinone ; Biosynthesis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: From the cultures of Streptomyces diastatochromogenes (strain Tü 2895) two novel benzo[b]fluorene quinones, named momofulvenone A (1) and B (2), were isolated. Difficulties in their spectroscopic characterization due to salt effects were overcome by fermentation in the presence of ammonium acetate. The structures were established by a detailed spectroscopic analysis. The polyketide origin of 1 and 2 was verified by feeding [1,2-13C2]acetate to the growing cultures of Tü 2895. The momofulvenones represent the nitrogen-free parent compound of the kinamycin family of antibiotics.
    Additional Material: 1 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199507158
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  • 2
    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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  • 3
    Electronic Resource
    Electronic Resource
    Metabolic products of microorganisms, 256. Pyrrolams, new pyrrolizidinones produced by Streptomyces olivaceus (1990)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1990 (1990), S. 525-530 
    Details
    ISSN: 0170-2041
    Keywords: Pyrrolams ; Metabolites, secondary ; Streptomyces olivaceus ; Pyrrolizidinones ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Pyrrolams A to D (1-4), biosynthetically new pyrrolizidinones produced by Streptomyces olivaceus, have been discovered by chemical screening. Their structures have been determined by spectroscopic methods and by a comparison of (R)-dihydropyrrolam A (5) with a synthetic sample obtained from (S)-proline. The pyrrolams differ from the necine bases found in plant-originating pyrrolizidine alkaloids by their less complicated structures.
    Additional Material: 2 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1990199001100
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  • 4
    Electronic Resource
    Electronic Resource
    Secondary metabolites by chemical screening, 18. Narbosines, new carbohydrate metabolites from Streptomyces (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 575-580 
    Details
    ISSN: 0170-2041
    Keywords: Narbosines ; Metabolites, secondary ; Streptomyces ; Rhodinosides ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In the culture broth of two new Strepomyces strains several novel 2,3,6-trideoxy-L-threo-hexose (rhodinose) metabolites, narbosines A to E (2-6, 8, 9), were detected besides α-N-acetylanhydro-L-ornithine (11) by using the chemical screening method. Their structures were deduced from spectroscopical data as well as from chemical transformations. Narbosine A (2/3) was shown to be a 1:1 anomeric mixture of α-L-rhodinopyranosyl-(1→4) -α/β-L-rhodinopyranose, the others are partially oxidatively and reductively transformed derivatives of 2/3. A destinct antiviral activity was observed for the described metabolites.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1991199101104
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  • 5
    Electronic Resource
    Electronic Resource
    Sekundärstoffe aus dem chemischen Screening, 16. Inthomycine, neue Oxazol-triene aus Streptomyces sp. (1991)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1991 (1991), S. 367-373 
    Details
    ISSN: 0170-2041
    Keywords: Inthomycins ; Metabolites, secondary ; Streptomyces sp. ; Oxazole-triene ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Secondary Metabolites by Chemical Screening, 161). - Inthomycins, New Oxazole-Trienes from Streptomyces sp.The oxazole-triene metabolites inthomycin A to C (2, 4, 6) have been discovered by chemical screening in the culture broth of Streptomyces sp. (strain Gö 2). Its separation was successful only when the compounds had previously been transformed into the 3-O-(S)-2-phenylbutanoates 3, 5 and 7. The structures were deduced from their spectroscopic data, especially those taken from 2D-NMR spectra. The natural products reveal differences in the (E/Z) configuration of its triene chains. By feeding [1-13C]acetate to growing cultures of strain Gö 2, it was determined that C-1 to C-10 of the inthomycins biosynthetically originated via the polyketide pathway. Inthomycin A (2) has already been known as a substructure element of oxazolomycin (1) and probably is identical with the recently described phthoxazolin.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199119910164
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  • 6
    Electronic Resource
    Electronic Resource
    Metabolic Products of Microorganisms, 266. Serpentene, a Novel Polyene Carboxylic Acid from Streptomyces (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 433-435 
    Details
    ISSN: 0170-2041
    Keywords: Serpentene ; Metabolites, secondary ; Streptomyces ; Screening, chemical ; Polyenes ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: From the culture filtrate of Streptomyces sp. a novel, bright yellow polyene carboxylic acid, named serpentene (1), was isolated by chemical screening methods. The structure elucidation of 1 is described. Remarkably, the C20 skeleton contains an ortho-substituted benzene ring bearing a dienoic acid and a nonatetraenyl residue. Concerning its structure and biosynthetic origin 1 is a unique secondary metabolite.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199319930170
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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, 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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  • 9
    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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