Zeeck, Axel

[["dc.bibliographiccitation.firstpage","323"],["dc.bibliographiccitation.issue","3"],["dc.bibliographiccitation.journal","JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1"],["dc.bibliographiccitation.lastpage","328"],["dc.contributor.author","Bode, H. B."],["dc.contributor.author","Zeeck, Axel"],["dc.date.accessioned","2018-11-07T11:10:34Z"],["dc.date.available","2018-11-07T11:10:34Z"],["dc.date.issued","2000"],["dc.description.abstract","Kendomycin [(-)-TAN 2162] 1 was re-isolated from Streptomyces violaceoruber (strain 3844-33C) in the course of our chemical screening programme. The structure with the relative configuration only was confirmed by the X-ray analysis of 1. The absolute configuration of 1 was determined by using the advanced Mosher's ester method applied to kendomycin acetonide 2. The biosynthesis of 1 was performed using stable isotope labelling experiments. From the results it is assumed that a highly oxygenated benzoic acid, derived from (3,5-dihydroxyphenyl)acetic acid, serves as the starter unit of the aliphatic polyketide chain. The cyclisation generating the 18-membered ansa-bridge by the formation of a C-C bond might follow a new type of aldol condensation. 1 and 2 exhibit antibacterial activity and strong cytotoxicity against different tumor cell lines."],["dc.identifier.doi","10.1039/a908387a"],["dc.identifier.isi","000085054900008"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/53234"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Royal Soc Chemistry"],["dc.relation.issn","0300-922X"],["dc.title","Structure and biosynthesis of kendomycin, a carbocyclic ansa-compound from Streptomyces"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","597"],["dc.bibliographiccitation.issue","6"],["dc.bibliographiccitation.journal","Phytochemistry"],["dc.bibliographiccitation.lastpage","601"],["dc.bibliographiccitation.volume","54"],["dc.contributor.author","Bode, H. B."],["dc.contributor.author","Zeeck, Axel"],["dc.date.accessioned","2018-11-07T10:42:43Z"],["dc.date.available","2018-11-07T10:42:43Z"],["dc.date.issued","2000"],["dc.description.abstract","Two new bisnaphthslene compounds, sphaerolone (1) and dihydrosphaerolone (2), together with 2-hydroxyjuglone (9), were isolated fi um the culture broth of a Sphaeropsidales sp. (strain F-24'707) after inhibition of the regular proceeding 1,8-dihydroxynayhthalene (DHN) biosynthesis with tricyclazole. The structures of 1 and 2 were established by detailed spectroscopic analysis and present novel bisnaphthalenes. The biosynthetic origin of 1 and 2 as dimerization products of 1,3,8-trihydroxynaphthalene, an intermediate of the DHN biosynthesis, is discussed. (C) 2000 Elsevier Science Ltd. Ail rights reserved."],["dc.identifier.doi","10.1016/S0031-9422(00)00145-X"],["dc.identifier.isi","000088715000008"],["dc.identifier.pmid","10963453"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/46869"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Pergamon-elsevier Science Ltd"],["dc.relation.issn","0031-9422"],["dc.title","Sphaerolone and dihydrosphaerolone, two bisnaphthyl-pigments from the fungus Sphaeropsidales sp F-24 ' 707"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","2665"],["dc.bibliographiccitation.issue","16"],["dc.bibliographiccitation.journal","JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1"],["dc.bibliographiccitation.lastpage","2670"],["dc.contributor.author","Bode, H. B."],["dc.contributor.author","Zeeck, Axel"],["dc.date.accessioned","2018-11-07T11:10:37Z"],["dc.date.available","2018-11-07T11:10:37Z"],["dc.date.issued","2000"],["dc.description.abstract","The origin of all oxygen atoms of the structurally unique polyketide antibiotic kendomycin 1 was confirmed by feeding [1-C-13,O-18(2)]acetate, [1-C-13,O-18(2)]propionate and O-18(2) to Streptomyces violaceoruber (strain 3844-33C) resulting in a more detailed insight into the biosynthesis of 1. Further information about the biosynthesis of the starter unit in which a chalcone synthase (CHS) must be involved was obtained from comparison of recent literature data with the requirements of the kendomycin biosynthesis. The incorporation of acetate into the methylmalonyl extender units reported previously was investigated by additional feeding [2-C-13]malonic acid and [1,4-C-13(2)]succinic acid to the strain. As a result, the coexistence of two independent pathways to methylmalonyl-CoA was demonstrated. Furthermore, feeding of N-acetylcysteamine and other thiols resulted in the formation of the new kendomycin derivatives 2 and 3 in good yields."],["dc.identifier.doi","10.1039/b003362f"],["dc.identifier.isi","000088767000017"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/53246"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Royal Soc Chemistry"],["dc.relation.issn","1470-4358"],["dc.title","Biosynthesis of kendomycin: origin of the oxygen atoms and further investigations"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","153"],["dc.bibliographiccitation.issue","2"],["dc.bibliographiccitation.journal","The Journal of Antibiotics"],["dc.bibliographiccitation.lastpage","157"],["dc.bibliographiccitation.volume","53"],["dc.contributor.author","Bode, H. B."],["dc.contributor.author","Wegner, B."],["dc.contributor.author","Zeeck, Axel"],["dc.date.accessioned","2018-11-07T10:33:38Z"],["dc.date.available","2018-11-07T10:33:38Z"],["dc.date.issued","2000"],["dc.description.abstract","The biosynthesis of cladospirone bisepoxide (1) was investigated by feeding C-13-labeled acetate to growing cultures of the fungus Sphaeropsidales sp. (strain F-24'707). C-13 NMR spectral analysis demonstrated the polyketide origin of both naphthalene units. The origin of two epoxide oxygens was confirmed as from air by cultivation of the strain in an O-18(2)-enriched atmosphere. The [O-18]incorporation pattern into palmarumycin C-12 (11), the putative precursor of 1 led to the hypothesis that the carbonyl oxygen of 1 is derived from water by exchange of an oxygen atom. inhibition of the biosynthesis of 1 with tricyclazole, an inhibitor of the 1,8-dihydroxynaphthalene (DHN) melanin biosynthesis, confirmed the connection of both biosynthetic pathways."],["dc.identifier.isi","000085563200008"],["dc.identifier.pmid","10805575"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/44657"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Japan Antibiot Res Assn"],["dc.relation.issn","0021-8820"],["dc.title","Biosynthesis of cladospirone bisepoxide, a member of the spirobisnaphthalene family"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","1451"],["dc.bibliographiccitation.issue","8"],["dc.bibliographiccitation.journal","European Journal of Organic Chemistry"],["dc.bibliographiccitation.lastpage","1456"],["dc.contributor.author","Bode, H. B."],["dc.contributor.author","Walker, M."],["dc.contributor.author","Zeeck, Axel"],["dc.date.accessioned","2018-11-07T11:01:27Z"],["dc.date.available","2018-11-07T11:01:27Z"],["dc.date.issued","2000"],["dc.description.abstract","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-C-13]acetate and O-18(2) 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."],["dc.identifier.isi","000086857400009"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/51148"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Wiley-v C H Verlag Gmbh"],["dc.relation.issn","1434-193X"],["dc.title","Secondary metabolites by chemical screening, 41 - Structure and biosynthesis of mutolide, a novel macrolide from a UV mutant of the fungus F-24 ' 707"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","619"],["dc.bibliographiccitation.issue","7"],["dc.bibliographiccitation.journal","ChemBioChem"],["dc.bibliographiccitation.lastpage","627"],["dc.bibliographiccitation.volume","3"],["dc.contributor.author","Bode, H. B."],["dc.contributor.author","Bethe, B."],["dc.contributor.author","Hofs, R."],["dc.contributor.author","Zeeck, Axel"],["dc.date.accessioned","2018-11-07T10:19:05Z"],["dc.date.available","2018-11-07T10:19:05Z"],["dc.date.issued","2002"],["dc.description.abstract","Fungi or bacteria that produce secondary metabolites often have the potential to bring up various compounds from a single strain. The molecular basis for this well-known observation was observation was confirmed in the last few years by several sequencing projects of different microorganisms. Besides well-known examples about induction of a selected biosynthesis (for example, by high- or low-phosphate cultivation media), no overview about the potential in this field for finding natural products was given. We have investigated the systematic alteration of easily accessible cultivation parameters (for example, media composition, aeration, culture vessel, addition of enzyme inhibitors) in order to increase the number of secondary metabolites available from one microbial source. We termed this way of revealing nature's chemical diversity the 'OSMAC (One Strain - Many Compounds) approach' and by using it we were able to isolate up to 20 different metabolites in yields up to 2.6 g L-1 from a single organism. These compounds cover nearly all major natural product families, and in some cases the high production titer opens new possibilities for semisynthetic methods to enhance even more the chemical diversity of selected compounds. The OSMAC approach offers a good alternative to industrial high-throughput screening that focuses on the active principle in a distance bioassay. In consequence, the detection of additional compounds that might be of interest as lead structures in further bioassays is impossible and clearly demonstrates the deficiency of the industrial procedure. Furthermore, our approach seems to be a useful tool to detect those metabolites that are postulated to be the final products of an amazing number of typical secondary metabolite genes clusters identified in microorganisms. If one assumes a (more or less) defined reservoir of genetic possibilities for several biosynthetic pathways in one strain that is used for a highly flexible production of secondary metabolites depending on the environment, the OSMAC approach might give more insight into the role of secondary metabolism in the microbial community or during the evolution of life itself."],["dc.identifier.doi","10.1002/1439-7633(20020703)3:7<619::AID-CBIC619>3.0.CO;2-9"],["dc.identifier.isi","000176625200003"],["dc.identifier.pmid","12324995"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/41593"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Wiley-v C H Verlag Gmbh"],["dc.relation.issn","1439-4227"],["dc.title","Big effects from small changes: Possible ways to explore nature's chemical diversity"],["dc.type","review"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","311"],["dc.bibliographiccitation.issue","4"],["dc.bibliographiccitation.journal","Phytochemistry"],["dc.bibliographiccitation.lastpage","316"],["dc.bibliographiccitation.volume","55"],["dc.contributor.author","Bode, H. B."],["dc.contributor.author","Zeeck, Axel"],["dc.date.accessioned","2018-11-07T09:54:39Z"],["dc.date.available","2018-11-07T09:54:39Z"],["dc.date.issued","2000"],["dc.description.abstract","The metabolite pattern of UV mutants of the spirobisnaphthalene producing fungus F-24'707 by TLC and HPLC analysis has been investigated. Mutants with differences in colony morphology or colour compared to the parent strain were isolated. Cultivation in shaking flasks and P flasks showed differences in the metabolite pattern of some of the strains. Furthermore, enzyme inhibitors were used to block the spirobisnaphthalene biosynthesis of the parent strain at different steps. Feeding of precursors and intermediates of cladospirone bisepoxide (15) led to a two-fold increase of the production of 15. From these data and preceding biosynthetic studies we deduced a general pathway for the biosynthesis of all spirobisnaphthalenes of the fungus F-24'707. This enables us to present the hypothesis that all bisnaphthalenes described so far are produced using a common pathway with only a few intermediates as central branching points. (C) 2000 Elsevier Science Ltd. All rights reserved."],["dc.identifier.doi","10.1016/S0031-9422(00)00307-1"],["dc.identifier.isi","000165660500004"],["dc.identifier.pmid","11117878"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/36580"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Pergamon-elsevier Science Ltd"],["dc.relation.issn","0031-9422"],["dc.title","UV mutagenesis and enzyme inhibitors as tools to elucidate the late biosynthesis of the spirobisnaphthalenes"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","3680"],["dc.bibliographiccitation.issue","9"],["dc.bibliographiccitation.journal","Applied and Environmental Microbiology"],["dc.bibliographiccitation.lastpage","3685"],["dc.bibliographiccitation.volume","66"],["dc.contributor.author","Bode, H. B."],["dc.contributor.author","Zeeck, Axel"],["dc.contributor.author","Pluckhahn, K."],["dc.contributor.author","Jendrossek, D."],["dc.date.accessioned","2018-11-07T10:24:57Z"],["dc.date.available","2018-11-07T10:24:57Z"],["dc.date.issued","2000"],["dc.description.abstract","Streptomyces coelicolor 1A and Pseudomonas citronellolis were able to degrade synthetic high-molecular-weight poly(cis-1,4-isoprene) and vulcanized natural rubber. Growth on the polymers was poor but significantly greater than that of the nondegrading strain Streptomyces lividans 1326 (control). Measurement of the molecular weight distribution of the polymer before and after degradation showed a time dependent increase in low-molecular-weight polymer molecules for S. coelicolor 1A and P. citronellolis, whereas the molecular weight distribution for the control (S. lividans 1326) remained almost constant. Three degradation products were isolated from the culture fluid of S. coelicolor 1A grown on vulcanized rubber and were identified as (6Z)-2,6-dimethyl -10-oxo-undec-6-enoic acid, (5Z)-6-methyl-undec-5-ene-2,9-dione, and (5Z,9Z)-6,10 dimethyl-pentadec 5,9-diene-2,13-dione. An oxidative pathway from poly(cis-1,4-isoprene) to methyl-branched diketones is proposed. It includes (i) oxidation of an aldehyde intermediate to a carboxylic acid, (ii) one cycle of beta-oxidation, (iii) oxidation of the conjugated double bond resulting in a beta-keto acid, and (iv) decarboxylation."],["dc.identifier.doi","10.1128/AEM.66.9.3680-3685.2000"],["dc.identifier.isi","000089109200004"],["dc.identifier.pmid","10966376"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/42756"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Amer Soc Microbiology"],["dc.relation.issn","0099-2240"],["dc.title","Physiological and chemical investigations into microbial degradation of synthetic poly(cis-1,4-isoprene)"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]

[["dc.bibliographiccitation.firstpage","3185"],["dc.bibliographiccitation.issue","18"],["dc.bibliographiccitation.journal","European Journal of Organic Chemistry"],["dc.bibliographiccitation.lastpage","3193"],["dc.contributor.author","Bode, H. B."],["dc.contributor.author","Walker, M."],["dc.contributor.author","Zeeck, Axel"],["dc.date.accessioned","2018-11-07T10:30:21Z"],["dc.date.available","2018-11-07T10:30:21Z"],["dc.date.issued","2000"],["dc.description.abstract","Variation of the culture conditions - static surface cultures in particular - of the fungus Sphaeropsidales sp. (strain F-24'707), which produces cladospirone bisepoxide (1), led to the isolation of eight new spirobisnaphthalenes - the cladospirones B to I (8-15) -together with seven known representatives of this class of secondary metabolites. Cladospirones C (9) and D (11) show antibiotic activity against bacteria and algae. The structures of cladospirone B (8) and E (12) were confirmed by X-ray structure analysis. Cladospirones C (9) and G to I (10, 14-15) represent new members of the spirobis-naphthalene family, thanks to their hydroxylation patterns. Moreover, they underline the extraordinary status of this interesting class of compounds as the most diverse secondary metabolites, allowing for their small number of carbon atoms, described to date. Almost all possible permutations of stereochemistry and oxygen substitution pattern on the C-10 skeleton are produced by different fungi."],["dc.identifier.isi","000089488600010"],["dc.identifier.uri","https://resolver.sub.uni-goettingen.de/purl?gro-2/43850"],["dc.notes.status","zu prüfen"],["dc.notes.submitter","Najko"],["dc.publisher","Wiley-v C H Verlag Gmbh"],["dc.relation.issn","1434-193X"],["dc.title","Secondary metabolites by chemical screening, 42 - Cladospirones B to I from Sphaeropsidales sp F-24 ' 707 by variation of culture conditions"],["dc.type","journal_article"],["dc.type.internalPublication","yes"],["dc.type.peerReviewed","yes"],["dc.type.status","published"],["dspace.entity.type","Publication"]]