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  • Articles: DFG German National Licenses  (6)
  • Myxobacteria  (6)
  • 1
    Electronic Resource
    Electronic Resource
    Apicularen A and B, Cytotoxic 10-Membered Lactones with a Novel Mechanism of Action from Chondromyces Species (Myxobacteria): Isolation, Structure Elucidation, and Biosynthesis (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 913-919 
    Details
    ISSN: 1434-193X
    Keywords: Myxobacteria ; Antibiotics ; Cytotoxic ; Structure elucidation ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---A novel highly cytotoxic metabolite, apicularen A (1), was isolated in a screening of the myxobacterial genus Chondromyces. The structure of 1 is characterized by a salicylic acid residue as part of a 10-membered lactone, which bears an acylenamine side chain. Compound 1 is an inhibitor of the proliferation of human cancer cell lines and induces apoptosis. Apicularen A (1) is present in nearly every strain of C. apiculatus, C. pediculatus, C. lanuginosus and C. robustus. Habitually 1 is accompanied by different amounts of a more polar variant, apicularen B (2), which was identified as 11-O-(2-N-acetamido-2-deoxy-β-D-glucopyranosyl)apicularen. According to feeding experiments with 13C-labeled acetates, glycine, and methionine, apicularen A (1) is an acetate-derived polyketide containing a glycine residue as precursor of the enamine. Uncommonly, the C3 starter unit is not assembled from propionate but from acetate and methionine.
    Additional Material: 6 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 2
    Electronic Resource
    Electronic Resource
    The Crocacins, Novel Antifungal and Cytotoxic Antibiotics from Chondromyces crocatus and Chondromyces pediculatus (Myxobacteria): Isolation and Structure Elucidation (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 1085-1089 
    Details
    ISSN: 1434-193X
    Keywords: Chondromycesspec. ; Myxobacteria ; Antibiotics ; Fungicides ; Structure elucidation ; Relative configuration ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: -Four novel antifungal and highly cytotoxic metabolites, the crocacins A-D (1-4), were isolated in our screening of the myxobacterial genus Chondromyces from strains of C. crocatus and C. pediculatus. Crocacin A, B, and D (1, 2, and 4) are unusual dipeptides of glycine and a 6-aminohexenoic or -hexadienoic acid, which is N-protected by a complex polyketide-derived acyl residue. The latter is a multiply substituted phenylundecatrienoic acid, which is found as its primary amide crocacin C (3). Based on 1H coupling constants, NOEs and MM+ calculations the relative configuration of the asymmetric centers and their preferred conformation are proposed for the crocacins.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 3
    Electronic Resource
    Electronic Resource
    Antibiotics from Gliding Bacteria, LXIII. Ratjadone: A New Antifungal Metabolite from Sorangium cellulosum (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 685-688 
    Details
    ISSN: 0947-3440
    Keywords: Antibiotics ; Sorangium cellulosum ; Myxobacteria ; Antifungal agent ; Biosynthesis ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The antifungal metabolite ratjadone (1) was isolated from the myxobacterium Sorangium cellulosum, strain So ce360. Production was achieved by fermentation in the presence of the adsorber resin XAD-16, extraction and separation by RP chromatography. The structure of 1 was determined by spectroscopic methods. It is characterized by a 4-hydroxytetrahydropyran and a 5,6-dihydropyran-2-one ring which are connected by an unsaturated C11 carbon chain. The polyketide origin of 1 was proven by feeding experiments with 13C-labeled precursors and NMR spectroscopic examinations.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199519950497
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    Paper (German National Licenses)
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  • 4
    Electronic Resource
    Electronic Resource
    Melithiazols A-N: New Antifungal β-Methoxyacrylates from Myxobacteria (1999)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1999 (1999), S. 2601-2608 
    Details
    ISSN: 1434-193X
    Keywords: β-Methoxyacrylates ; Melithiazols ; Myxobacteria ; Natural products ; Fungicides ; Structure-activity relationships ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: From cultures of Melittangium lichenicola, Archangium gephyra and Myxococcus stipitatus, thirteen new β-methoxyacrylate (MOA) fungicides related to myxothiazols (1) have been isolated. Melithiazols A (2a), D (2b), K (2c), and L (2d) are characterized by a thiazoline-thiazole system, whereas melithiazols B (3a), E (3b), F (3c), G (3d), H (3e), I (3f), M (3g), and N (3h) are bis(thiazoles). Melithiazol C (4), as the first representative of this class of compounds, contains only one thiazole ring. The structures were established on the basis of spectroscopic data, and confirmed in the case of melithiazol E (3b), including its relative configuration, by an X-ray structure analysis. The absolute configuration of melithiazols A (2a) and B (3a) was determined by degradation and CD spectroscopy. Antifungal and cytotoxic activities, inhibition of NADH oxidation, and lipophilicities of melithiazols 2-4, myxothiazols 1, and strobilurin-type compounds are compared.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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    Paper (German National Licenses)
  • 5
    Electronic Resource
    Electronic Resource
    Antibiotics from Gliding Bacteria, LIV. Isolation and Structure Elucidation of Soraphen A1α, a Novel Antifungal Macrolide from Sorangium cellulosumDedicated to Prof. Dr. Wolfgang Steglich on the occasion of his 60th birthday. (1993)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1993 (1993), S. 1017-1021 
    Details
    ISSN: 0170-2041
    Keywords: Macrolides ; Antibiotics ; Fungicides ; Sorangium cellulosum ; Myxobacteria ; Soraphen ; Calculations, MMX force field ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: From the myxobacterium Sorangium cellulosum, strain So ce26, a novel group of highly active antifungal metabolites was isolated. Large-scale production of the basic compound soraphen A1α (1) was achieved by fermentation in the presence of the adsorber resin XAD-16, extraction and crystallization. The 18-membered macrolide structure of 1 was determined by spectroscopic methods. X-ray crystal structure analysis revealed the absolute configuration of the ten asymmetric centers. According to proton coupling constants and difference NOE measurements the solution conformation in CDCl3 and [D6]DMSO is very similar to that in the crystal structure.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1993199301161
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    Paper (German National Licenses)
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  • 6
    Electronic Resource
    Electronic Resource
    Antibiotics from gliding bacteria, LVII. Tartrolons: New boron-containing macrodiolides from Sorangium cellulosum (1994)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1994 (1994), S. 283-289 
    Details
    ISSN: 0170-2041
    Keywords: Boron-containing antibiotics ; Macrodiolides ; Sorangium cellulosum ; Myxobacteria ; Antibiotics ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The antibacterial metabolites tartrolon A1, A2, A3 (1a-1c) and B (2) were isolated from the myxobacterium Sorangium cellulosum, strain So ce678. Large-scale production was achieved by fermentation in the presence of the adsorber resin XAD-16, extraction, and separation by RP chromatography followed by crystallization. The 42-membered macrodiolide structure of 1a-1c and 2 was determined by spectroscopic methods. Compound 2 was identified as a boric acid ester of 1c, whereas 1a and 1b are stereoisomers of 1c. All components could be chemically converted into each other. A correlation between the production of 2 and the borate concentration in the medium was found, depending on nutrients and container material used.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199419940310
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    Paper (German National Licenses)
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