Peptid-Irrgarten: Die Struktur des neuartigen Lantibiotikums Labyrinthopeptin A2 (siehe Bild) enthält eine zuvor unbekannte carbacyclische, posttranslational modifizierte Aminosäure, die Labionin genannt wurde. Im Anschluss an die Strukturaufklärung gelang die Identifizierung des Biosynthesegenclusters der Labyrinthopeptine. Labyrinthopeptin A2 zeigt eine ausgeprägte In-vivo-Wirksamkeit (Verminderung taktiler Allodynie) in der Maus in einem Nervenverletzungsmodell. Detailed facts of importance to specialist readers are published as ”Supporting Information”. Such documents are peer-reviewed, but not copy-edited or typeset. They are made available as submitted by the authors. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

A-maze-ing peptides: The structure of the novel lantibiotic labyrinthopeptin A2 (see picture) contains labionin—an unprecedented carbacyclic, posttranslationally modified amino acid. The identification of the biosynthetic gene cluster of labyrinthopeptins was also successful. Labyrinthopeptin A2 revealed a pronounced in vivo efficacy (attenuation of tactile allodynia) in a mouse model of neuropathic pain.

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Bendigoles A similar to C are the first secondary metabolites to be isolated from a member of the actinomycete genus Gordonia. They were detected in a culture filtrate extract of Gordonia australis Acta 2299 by HPLC-diode array analysis and characterized as new steroids by mass spectrometry and NMR experiments. Bendigole C show binding affinity to the human progesterone and A-C to androgen receptor but are inactive at mineralocorticoid and estrogen receptors. In in vitro transactivation studies bendigoles A and C showed moderate and weak androgenic activities.

Wirkstoffe aus dem Meer: Drei neue Netropsin-artige Antibiotika (1–3) mit einer bisher unbekannten Furangrundstruktur wurden aus marinen Actinomyceten isoliert und ihre Struktur mithilfe von Massenspektrometrie und 2D-NMR-Spektroskopie aufgeklärt. Sie haben Antitumoraktivität und induzieren im Unterschied zu Netropsin eine Hochregulation von p53 und des Cyclinkinase-Inhibitors p21.

Drugs from the sea: Three new netropsin-type antibiotics (1–3) with a hitherto unknown furan core structure have been isolated from marine actinomycete strains and their structures elucidated by means of mass spectrometry and 2D NMR spectroscopy. The compounds show antitumor activity and, in contrast to netropsin, they induce upregulation of p53 and the cyclin kinase inhibitor p21. Supporting information for this article is available on the WWW under http://www.wiley-vch.de/contents/jc_2002/2008/z705295_s.pdf or from the author. Please note: The publisher is not responsible for the content or functionality of any supporting information supplied by the authors. Any queries (other than missing content) should be directed to the corresponding author for the article.

A family of three novel aminofuran antibiotics named as proximicins was isolated from the marine Verrucosispora strain MG-37. Proximicin A was detected in parallel in the marine abyssomicin producer “Verrucosispora maris” AB-18-032. The characteristic structural element of proximicins is 4-amino-furan-2-carboxylic acid, a hitherto unknown γ-amino acid. Proximicins show a weak antibacterial activity but a strong cytostatic effect to various human tumor cell lines.

Bendigoles A~C are the first secondary metabolites to be isolated from a member of the actinomycete genus Gordonia . They were detected in a culture filtrate extract of Gordonia australis Acta 2299 by HPLC-diode array analysis and characterized as new steroids by mass spectrometry and NMR experiments. Bendigole C show binding affinity to the human progesterone and A~C to androgen receptor but are inactive at mineralocorticoid and estrogen receptors. In in vitro transactivation studies bendigoles A and C showed moderate and weak androgenic activities.

The freshwater cyanobacterium Planktothrix rubescens produces the cyclooctapeptide cyclo(Pro-Gly-Leu-Val-Met-Phe-Gly-Val). The chemical structure is new. This homodetic cyclic octapeptide was named planktocyclin ( 1). It consists solely of proteinogenic l-amino acids and is a strong inhibitor of mammalian trypsin and alpha-chymotrypsin and a moderately active inhibitor of human recombinant caspase-8. Mass spectrometric and 2D-NMR spectroscopic data allowed the determination of its structure. Synthetic planktocyclin was identical to the natural product.

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12-epi-Hapalindole J isonitrile (1) and three previously described hapalindoles, 12-epi-hapalindole C isonitrile (2), hapalindole L (3) and 12-epi-hapalindole E isonitrile (4) were isolated and identified as insecticidal alkaloids of the biofilm-forming freshwater cyanobacterium Fischerella ATCC 43239 (Stigonematales). The structures of the purified compounds were elucidated by ESI–FTICR–MS, GC–EI–MS and various 2D NMR experiments. At 26 μM hapalindole 1 killed 100% of the larvae of the dipteran Chironomus riparius within 48 h. Insecticidal activities were also found at similar concentration for the hapalindoles 2–4. The bioactivity of hapalindoles demonstrates that cyanobacterial biofilms can be considered as promising sources of insecticidal metabolites which might be useful for the biocontrol of dipterans.

Abyssomicin C is a complex polyketide-type antibiotic and the first natural inhibitor of the p-aminobenzoate biosynthesis produced by the marine Verrucosispora strain AB-18-032. We have now isolated three novel naturally produced abyssomicins, among them the even more active atrop-abyssomicin C. The chemical structures were elucidated by mass spectrometry and NMR spectroscopy.

Subtle restraint: Abyssomicin C and atrop-abyssomicin C are polyketide-type antibiotics produced by the marine actinomycete of the genus Verrucosispora. Investigations of the functional pathway show that a subunit of 4-amino-4-deoxychorismate synthase from Bacillus subtilis is irreversibly inhibited through covalent binding to the side chain of Cys 263, undergoing a rearrangement to a structure of the abyssomicin D type (see scheme).

Subtile Hemmung: Abyssomicin C und atrop-Abyssomicin C sind Antibiotika vom Polyketid-Typ, die beide von marinen Actinomyceten der Gattung Verrucosispora produziert werden. Studien zum Wirkmechanismus belegen, dass eine Untereinheit der 4-Amino-4-desoxychorismat-Synthase aus Bacillus subtilis durch kovalente Bindung von atrop-Abyssomicin C an die Seitenkette Cys 263 irreversibel inhibiert wird, wobei eine Umlagerung zu einer Struktur ähnlich der von Abyssomicin D stattfindet (siehe Schema).

Mycorrhiza helper bacterium Streptomyces strain AcH 505 stimulates ectomycorrhiza, formation between spruce and fly agaric by supporting fungal growth whereas growth of pathogenic fungi is suppressed. A fungal growth promoting substance was isolated and the chemical structure elucidated by mass spectrometry and NMR spectroscopy. The absolute configuration of the novel fungal growth promoting compound auxofuran (1) was deduced from NMR data with the help of Mosher esters.

A new depsipeptide, cyanopeptolin 963 A (1), was isolated from an axenic strain of the toxic freshwater cyanobacterium Microcystis PCC 7806. The structure of this compound was elucidated by chemical and spectroscopic analyses, including high-resolution ESI-FTICR-MS, 2-D NMR, and GC-MS of the hydrolysate. The major structural difference compared to previously characterized cyanopeptolins of this strain is the replacement of the basic amino acid in position 3 by L-tyrosine. Compound 1 displayed inhibitory activity against chymotrypsin with an IC50 value of 0.9 microM.

Model mutants. The biosynthesis of glycopeptide antibiotics must be understood before it can be reprogrammed to generate altered antibiotics. Based on a detailed HPLC-ESI-MS analysis of linear and cyclic peptide intermediates of balhimycin biosynthesis mutants, a new model for glycopeptide assembly is suggested (see figure). We propose that the three central oxidative cyclizations by P450-dependant monooxygenases occur during peptide assembly before cleavage from the nonribosomal peptide synthetase complex.

Politik und Demokratie interessant, spannend und herausfordernd präsentieren, Bürger zur Meinungsbildung und -äußerung motivieren. Das sind die Ziele von DEMOS (Delphi Mediation Online System), einer Internet-basierten Diskussions- und Informationsplattform, die im Rahmen eines von der EU geförderten Projekts entwickelt wurde. Ein möglichst breites Spektrum an Benutzergruppen soll mit einer übersichtlichen, leicht bedienbaren und grafisch attraktiven Benutzungsoberfläche den Einstieg in die ?-Demokratie finden und sich in politische Fragestellungen und Entscheidungen einbringen.

Online-Dienste, die zur Unterstützung eines selbstorganisierten und selbstbestimmten Lebens von Menschen, die auf die Unterstützung anderer bei der Bewältigung ihres alltäglichen Lebens angewiesen sind, werden als Tele-Assistenzsysteme bezeichnet. Das Design eines solchen Systems und welche Auswirkungen die kontex-tuellen Bedingungen für den Einsatz des Systems auf das Design hatten, wird im Folgenden beschrieben.