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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
    Metabolic products of microorganisms. Part 262Part 261: [1].. The absolute configuration of sphydrofuran, a widespread metabolite from streptomycetes (1991)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 74 (1991), S. 1281-1286 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Sphydrofuran (1) was isolated from the culture filtrate of Streptomyces sp. (strain Gö 28 and Tü 3616) by chemical screening methods. Metabolite 1 is an anomeric and ring-chain tautomeric mixture and could easily be transformed into the stable furan derivative 2 under acidic conditions. The constitution and relative configuration of 1 was established by X-ray crystallography of its 8-O-methyl derivative 3a. The absolute configuration at C(4) of 1 and thus of the whole molecule (3R,4S,5S) could be determined starting from 2 using the Helmchen method.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19910740617
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  • 3
    Electronic Resource
    Electronic Resource
    Stoffwechselprodukte von Mikroorganismen. 253. Mitteilung252, Mitteilung. Hormaomycin, ein neues Peptid-lacton mit morphogener Aktivität auf Streptomyceten (1989)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 72 (1989), S. 426-437 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Hormaomycin, a Novel Peptide Lactone with Morphogenetic Activity on StreptomycesA culture identified as Streptomyces griseoflavus (strain W-384) has been found to produce a novel peptide-lactone antibiotic designated hormaomycin (6). The empirical molecular formula of the compound is established to be C55H69ClN10O14. The constituent amino acids of the antibiotic are suggested to be allothreonine (1; 1), isoleucine (2; 1), 3-methyl-phenylalanine (3; 2), and, for the first time identified from a natural source, 4-[(Z)-prop-1-enyl]-proline (4; 1) and 3-(2-nitrocyclopropyl)-alanine (5; 2). The amino acids were delivered by acidic hydrolysis and assigned by high-resolution- GC/MS analysis (after transformation to derivatives) in combination with extended 2D-NMR experiments of the antibiotic itself. From the latter, it became plausible that the N-terminus of the peptide chain is acylated by a Cl-containing derivative of 1H-pyrrol-2-carboxylic acid. Hormaomycin is active against some Gram-positive bacteria. In addition, the antibiotic exhibits potent aerial mycelium-inducing activity and effects the production of antibiotics.
    Notes: No abstract.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19890720303
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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
    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
    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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  • 7
    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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  • 8
    Electronic Resource
    Electronic Resource
    The chemistry of unusual macrolides, 2. Spectroscopic and biosynthetic investigations of the V-type ATPase inhibitor concanamycin A (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 305-312 
    Details
    ISSN: 0170-2041
    Keywords: Concanamycin A ; Macrolides ; Biosynthesis ; Polyketide ; Conformational studies ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The 1H- and 13C-NMR spectra of the conformationally flexible macrolide concanamycin A (1) have been assigned by the use of 2D NMR techniques at low temperatures and have enabled biosynthetic studies on this most potent inhibitor of vacuolar ATPases. By feeding of different [13C]-labeled precursors to Streptomyces sp. (strain Gö 22/15) the polyketide origin of the concanamycin skeleton was proved. It arises from a tetradecaketide, which is based on four acetate and seven propionate units besides one butyrate and two unusual C2 building blocks from the triose pool. In combination with former findings it is possible to predict the biogenetic assembly of several strongly related unusual macrolides, for which the group name “plecomacrolides” should be used in future. The results are discussed in the light of modern hypothesis as stated for polyketide pathways.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940313
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  • 9
    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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  • 10
    Electronic Resource
    Electronic Resource
    Bestimmung der Verknüpfung dimerer Isochromanchinone durch Diazomethan-Abbau (1983)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1983 (1983), S. 510-518 
    Details
    ISSN: 0170-2041
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Description / Table of Contents: Determination of the Connection of Dimeric Isochromanequinone by Diazomethane DegradationThe diazomethane degradation is a chemical method to determine the connection of the halves of the molecule in the actinorhodines and naphthocyclinones and to decide between the regioisomers of dimeric isochromanequinones. The prefered direction of the addition of diazomethane to the deacetylnaphthocyclinones results from the structure of the indazolequinones 7b, 10A, 13A, and 16A as well as the seco-naphthocyclinones 17a-c formed by thermal fragmentation of the diazomethane adducts. _ The different portion of the indazolequinones 16A and 16B resulting from γ-naphthocyclinone (14a) and γ-iso-naphthocyclinone (22a), respectively, refers to a mistake of dimerization made in biosynthesis
    Notes: Mit dem Diazomethan-Abbau steht eine chemische Methode zur Verfügung, um die Verknüpfung der Molekülhälften bei den Actinorhodinen und Naphthocyclinonen zu bestimmen und zwischen Regioisomeren der dimeren Isochromanchinone zu entscheiden. Die bevorzugte Additionsrichtung des Diazomethans an die Desacetylnaphthocyclinone folgt aus der Struktur der Indazolchinone 7b, 10A, 13A und 16A sowie der seco-Naphthocyclinone 17a-c, die bei der thermischen Fragmentierung der Diazomethan-Addukte entstehen. _ Der unterschiedliche Anteil der Indazolchinone 16A und 16B aus γ-Naphthocyclinon (14a) bzw. γ-iso-Naphthocyclinon (22a) deutet auf einen Dimerisierungsfehler bei der Biosynthese von 22a hin.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.198319830315
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