Search

The early stages of antibiotic development include the identification of novel hit compounds. Since actinomycetes and myxobacteria are still the most important natural sources of active metabolites, we provide an overview on these producers and discuss three of the most promising approaches toward finding novel anti-infectives from microorganisms. These are defined as the use of biodiversity to find novel producers, the variation of culture conditions and induction of silent genes, and the exploitation of the genomic potential of producers via "genome mining". Challenges that exist beyond compound discovery are outlined in the last section.

A novel myxobacterium, strain MSr11462T, was isolated in 2015 from a soil sample collected form Kish Island beach, Persian Gulf, Iran. It displayed general myxobacterial features like Gram-negative staining, rod-shaped vegetative cells, gliding on solid surfaces, microbial lytic activity, fruiting-body-like aggregates and myxospore-like structures. The strain was mesophilic, aerobic and showed a chemoheterotrophic mode of nutrition. It was resistant to many antibiotics like gentamycin, polymyxin, fusidic acid and trimethoprim, and the key fatty acids of whole-cell hydrolysates were iso-C15 : 0, C16 : 0, iso-C17 : 0, C18 : 1, iso-C17 : 1 2-OH, C18 : 1 2-OH, iso-C15 : 0 OAG (O-alkylglycerol) and C16 : 1 OAG. The 16S rRNA gene sequence showed highest similarity (98.6 %) to Racemicystis crocea strain MSr9521T (GenBank accession no. KT591707). The phylogenetic analysis based on 16S rRNA gene sequences and matrix-assisted laser-desorption/ionization time-of-flight (MALDI-TOF) spectroscopy data supports a novel species of the family Polyangiaceae and the genus Racemicystis . DNA–DNA hybridization showed only about 50 % similarity between the novel strain and the phylogenetically closest species, Racemicystis. crocea MSr9521T. On the basis of a comprehensive taxonomic study, we propose a novel species, Racemicystis persica sp. nov., for strain MSr11462T (=DSM 103165T=NCCB 100606T).

The strain no. VY46 was isolated from agricultural soil of Slovak republic and tested for potential antimicrobial activity against various human pathogens. On the basis of results, strain VY46 significantly inhibited growth of yeast Candida albicans and therefore was used for further characterization. In order to explore the potential bioactivities, extract of the fermented broth culture was prepared with organic solvent extraction method. The ethylacetate extract was subjected to HPLC fractionation against Candida albicans and followed by LC/MS analysis for potential production of anticandidal substances. The analysis resulted in the identification of two antimycins antibiotics, which may be responsible for important anticandidal activity of the strain. On the basis of liquid chromatography and mass spectrometry the antibiotics were identified as Urauchimycin A and Kitamycin A. According tothe results from cultural, morphological, physiological, biochemical and 16S rRNA gene sequence methods, the strain was identified as Streptomyces albidoflavus. In addition, neighbor-joining phylogenetic tree confirmed the relationships of this strain to other members of Streptomyces genera.

Bacteria have been by far the most promising resource for antibiotics in the past decades and will in all undoubtedly remain an important resource of innovative bioactive natural products in the future. Actinobacteria have been screened for many years, whereas the Myxobacteria have been underestimated in the past. Even though Actinobacteria belong to the Gram-positive and Myxobacteria to the Gram-negative bacteria both groups have a number of similar characters, as they both have huge genomes with in some cases more than 10kB and a high GC content and they both can differentiate and have often cell cycles including the formation of spores. Actinobacteria have been used for the antibiotic research for many years, hence it is often discussed whether this resource has now been exhaustively exploited but most of the screening programs from pharmaceutical companies were basing on the cultivation mainly of members of the genus Streptomyces or Streptomyces like strains (e.g., some Saccharopolyspora, Amycolatopsis or Actinomadura species) by use of standard methods so that many of the so called "neglected" Actinobacteria were overlooked the whole time. The present review gives an overview on the state of the art regarding new bioactive compounds with a focus on the marine habitats. Furthermore, the evaluation of Myxobacteria in our ongoing search for novel anti-infectives is highlighted.

Planctomycetes are conspicuous, ubiquitous, environmentally important bacteria. They can attach to various surfaces in aquatic habitats and form biofilms. Their unique FtsZ-independent budding cell division mechanism is associated with slow growth and doubling times from six hours up to one month. Despite this putative disadvantage in the struggle to colonize surfaces, Planctomycetes are frequently associated with aquatic phototrophic organisms such as diatoms, cyanobacteria or kelp, whereby Planctomycetes can account for up to 50 % of the biofilm-forming bacterial population. Consequently, Planctomycetes were postulated to play an important role in carbon utilization, for example as scavengers after phototrophic blooms. However, given their observed slow growth, such findings are surprising since other faster- growing heterotrophs tend to colonize similar ecological niches. Accordingly, Planctomycetes were suspected to produce antibiotics for habitat protection in response to the attachment on phototrophs. Recently, we demonstrated their genomic potential to produce nonribosomal peptides, polyketides, bacteriocins, and terpenoids that might have antibiotic activities. In this study, we describe the development of a pipeline that consists of tools and procedures to cultivate Planctomycetes for the production of antimicrobial compounds in a chemically- defined medium and a procedure to chemically mimic their interaction with bacteria such as for example Cyanobacteria. We evaluated and adjusted screening assays to allow the hunt for planctomycetal antibiotics. As proof of principle, we demonstrate antimicrobial activities of planctomycetal extracts from Planctopirus limnophila DSM 3776, Rhodopirellula baltica DSM 10527, and the recently isolated strain Pan216. By combining UV/Vis and high resolution mass spectrometry data from High-Performance Liquid Chromatography fractionations with growth inhibition of indicator strains, we were able to assign the antibiotic activity to candidate peaks related to planctomycetal antimicrobial compounds. The MS analysis points towards the production of novel bioactive molecules with novel structures. Consequently, we developed a large scale cultivation procedure to allow future structural elucidation of such compounds. Our findings might have implications for the discovery of novel antibiotics as Planctomycetes represent a yet untapped resource that could be developed by employing the tools and methods described in this study.

Bacteria have been by far the most promising resource for antibiotics in the past decades and will in all undoubtedly remain an important resource of innovative bioactive natural products in the future. Actinobacteria have been screened for many years, whereas the Myxobacteria have been underestimated in the past. Even though Actinobacteria belong to the Gram-positive and Myxobacteria to the Gram-negative bacteria both groups have a number of similar characters, as they both have huge genomes with in some cases more than 10kB and a high GC content and they both can differentiate and have often cell cycles including the formation of spores. Actinobacteria have been used for the antibiotic research for many years, hence it is often discussed whether this resource has now been exhaustively exploited but most of the screening programs from pharmaceutical companies were basing on the cultivation mainly of members of the genus Streptomyces or Streptomyces like strains (e.g., some Saccharopolyspora, Amycolatopsis or Actinomadura species) by use of standard methods so that many of the so called “neglected” Actinobacteria were overlooked the whole time. The present review gives an overview on the state of the art regarding new bioactive compounds with a focus on the marine habitats. Furthermore, the evaluation of Myxobacteria in our ongoing search for novel anti-infectives is highlighted.

In an antibiotic lead discovery program, the known strain Streptomyces armeniacus DSM19369 has been found to produce three new natural products when cultivated on a malt-containing medium. The challenging structural elucidation of the isolated compounds was achieved by using three independent methods, that is, chemical degradation followed by NMR spectroscopy, a computer-assisted structure prediction algorithm, and X-ray crystallography. The compounds, named armeniaspirol A-C (2-4), exhibit a compact, hitherto unprecedented chlorinated spiro[4.4]non-8-ene scaffold. Labeling experiments with [1-(13)C] acetate, [1,2-(13)C2] acetate, and [U-(13)C] proline suggest a biosynthesis through a rare two-chain mechanism. Armeniaspirols displayed moderate to high in vitro activities against gram-positive pathogens such as methicillin-resistant S. aureus (MRSA) or vancomycin resistant E. faecium (VRE). As analogue 2 was active in vivo in an MRSA sepsis model, and showed no development of resistance in a serial passaging experiment, it represents a new antibiotic lead structure.

Lantibiotics are peptides that are ribosomally synthesized from bacteria such as staphylococci, lactobacilli, and actinomycetes. The common structural characteristic of lantibiotics is the noncanonical amino acid lanthionine (Lan, 1; Figure 1), which confers conformational stability to the peptide. The most prominent representative is nisin, which is a lipid II binder, and has been known for its use as an antimicrobial food preservative for over 40 years. The majority of studies on molecular targets and bioactivities are focused on potential applications of lantibiotics as anti-infectives. Duramycin (Moli1901) is in phase II clinical trials for the treatment of cystic fibrosis because of its ability to increase chloride transport in airway epithelium. Biosurfactant function in the life cycle of streptomycetes has been elucidated for some members such as SapB. Herein, we present the structures, the biosynthesis gene cluster, and the bioactivities of labyrinthopeptins, which are lantibiotics that contain labionin, an unprecedented carbacyclic, posttranslationally modified amino acid. The culture extracts of the novel actinomycete Actinomadura namibiensis DSM 6313 attracted our attention because of their activity against the Herpes simplex virus. Active fractions of the extracts contained a peptide that was isolated by chromatographic methods. The high-resolution ESI-FTICR mass spectrum showed a mass of 984.3333 Da for the doubly charged sodium adduct of the compound, corresponding to a neutral monoisotopic mass of 1922.6872 Da and the molecular formula C85H110N20O24S4 (Dm/m= 0.7 ppm). Amino acid analysis revealed Gly and the l-enantiomers of Ala, Thr, Leu, Asx, Cys, Phe, Glx, Trp (ratio 1:1:1:2:1:2:1:1:2). However, the total molecular mass of the detected amino acids indicated a considerable mass difference, which could not be correlated with known peptidic or lantibiotic posttranslational modifications. Resolution of the structure by H NMR spectroscopy was impeded by broad signals in parts of the spectrum. The X-ray structure at 1.0 resolution (Figure 1) enabled interpretation of the analytical data and displayed several unique structural features. In view of its labyrinthine structure, the compound was named labyrinthopeptin A2 (2). Labyrinthopeptin A2 has a globular structure that consists primarily of hydrophobic amino acids. Formally, the structure can be dissected into two nonapeptides. Each peptide bears a C-terminal Cys residue that forms a disulfide bond, which is a comparatively rare modification in lantibiotics, but is found for sublancin 168 from B. subtilis. Each nonapeptide contains a tetrapeptide (ring A) and a pentapeptide (ring B) that share a quaternary aC atom; labyrinthopeptin A rings are formed by a methylene group between the aC atoms of Lab1/ Lab10 and Lab4/Lab13 (Figure 1). A carbacyclic side-chain linkage is unprecedented in peptides and proteins. We propose the name labionin (Lab) for the corresponding amino acid (Figure 1). Labionin 3 represents an aC quaternary substituted amino acid with a subtle structural resemblance to a-aminoisobutyric acid (Aib) or isovaline (Iva), which are incorporated in fungal peptaibol-type antibiotics. The stereocenters of 3 can be assigned to (2S,4S,8R)-labionin (Lab), which is consistent with the configuration of (2S,6R)lanthionine of other lantibiotics. The formation of the 11membered ring that involves 3 forces the peptide backbone into a conformation with cis-amide bonds between Asp2– Trp3 and Thr11–Gly12, respectively (Figure 1). The presence of cis-amide bonds and the absence of a hydrogen bond between Lab1–Lab4 and Lab10–Lab13, respectively, show that the turn motif in 2 is clearly different from a b-turn motif. Subsequent identification of the biosynthetic gene cluster was performed from a cosmid library of A. namibiensis by means of degenerated primer probes, followed by sequencing [*] Dr. T. Schmiederer, Dr. K. Schneider, Dr. A. Reicke, Dr. D. Butz, Dr. S. Keller, Prof. Dr. R. D. S ssmuth Technische Universit t Berlin, Fakult t II—Institut f r Chemie Strasse des 17. Juni 124, 10623 Berlin (Germany) Fax: (+49)30-314-24205 E-mail: suessmuth@chem.tu-berlin.de Homepage: http://www2.tu-berlin.de/fb5/Suessmuth/ contact.html Dr. K. Meindl, Prof. Dr. G. M. Sheldrick Universit t G ttingen (Germany)

The lack of new antibiotics in the pharmaceutical pipeline guides more and more researchers to leave the classical isolation procedures and to look in special niches and ecosystems. Bioprospecting of extremophilic Actinobacteria through mining untapped strains and avoiding resiolation of known biomolecules is among the most promising strategies for this purpose. With this approach, members of acidtolerant, alkalitolerant, psychrotolerant, thermotolerant, halotolerant and xerotolerant Actinobacteria have been obtained from respective habitats. Among these, little survey exists on the diversity of Actinobacteria in arid areas, which are often adapted to relatively high temperatures, salt concentrations, and radiation. Therefore, arid and desert habitats are special ecosystems which can be recruited for the isolation of uncommon Actinobacteria with new metabolic capability. At the time of this writing, members of Streptomyces, Micromonospora, Saccharothrix, Streptosporangium, Cellulomonas, Amycolatopsis, Geodermatophilus, Lechevalieria, Nocardia and Actinomadura are reported from arid habitats. However, metagenomic data present dominant members of the communities in desiccating condition of areas with limited water availability that are not yet isolated. Furthermore, significant diverse types of polyketide synthase (PKS) and nonribosomal peptide synthetase (NRPS) genes are detected in xerophilic and xerotolerant Actinobacteria and some bioactive compounds are reported from them. Rather than pharmaceutically active metabolites, molecules with protection activity against drying such as Ectoin and Hydroxyectoin with potential application in industry and agriculture have also been identified from xerophilic Actinobacteria. In addition, numerous biologically active small molecules are expected to be discovered from arid adapted Actinobacteria in the future. In the current survey, the diversity and biotechnological potential of Actinobacteria obtained from arid ecosystems, along with the recent work trend on Iranian arid soils, are reported.

The taxonomic status of ‘Actinoplanes liguriae’ A/6353 and ‘Actinoplanes teichomyceticus’ AB8327 was established by using a polyphasic approach. Strains A/6353 and AB8327 form distinct phylogenetic lineages in the 16S rRNA gene tree of members of the genus Actinoplanes and are related moderately and closely to Actinoplanes rectilineatus and Actinoplanes cyaneus, respectively. Morphological, cultural and physiological properties indicated that strains A/6353 and AB8327 represent separate, novel species of the genus Actinoplanes, Actinoplanes liguriensis sp. nov. (type strain A/6353T=FH 2244T=DSM 43865T=ATCC 31048T=BCRC 12121T=CBS 355.75T=IMSNU 22127T=JCM 3250T=KCTC 9536T=KCC A-0250T=NBRC 13997T=NCIMB 12636T=NRRL B-16723T=SANK 62178T) and Actinoplanes teichomyceticus sp. nov. (type strain AB8327T=FH 2149T=DSM 43866T=ATCC 31121T=BCRC 12106T=FERM P-3462T=IMSNU 20043T=IMET 9254T=JCM 3252T=KCC A-0252T=KCTC 9543T=NBRC 13999T=NCIMB 12640T=NRRL B-16726T=SANK 60479T).

A previous phylogenetic study on type strains of the genus Micromonospora and Micromonospora species bearing non-validly published names has pointed towards the species status of several of latter strains. Subsequent studies on morphological, cultural, chemotaxonomic, metabolic, and genomic properties, and on whole cell mass spectrometric analyses by matrix adsorbed laser desorption/ionization time-of-flight (MALDI-TOF) confirmed the species status, leading to the proposal of eight new Micromonospora species: Micromonospora citrea sp. nov., type strain DSM 43903T, Micromonospora echinaurantiaca sp. nov., type strain DSM 43904T, Micromonospora echinofusca sp. nov., type strain DSM 43913T, Micromonospora fulviviridis sp. nov., type strain DSM 43906T, Micromonospora inyonensis sp. nov., type strain DSM 46123T, Micromonospora peucetia sp. nov., type strain DSM 43363T, Micromonospora sagamiensis sp. nov., type strain DSM 43912T and Micromonospora viridifaciens sp. nov., type strain DSM 43909T.

Strain DSM 44594T, which produces the glycopeptide antibiotic decaplanin, is a member of the genusAmycolatopsisbased on 16S rRNA gene sequence analysis and chemotaxonomic properties. It is the first member of this genus that is reported to form pseudosporangia, which resemble those of members of the genusKibdelosporangium. Phylogenetically, the novel taxon is related toAmycolatopsis orientalis,Amycolatopsis lurida,Amycolatopsis azurea,Amycolatopsis japonicaandAmycolatopsis keratiniphila. Morphological, cultural and physiological properties, the production of a unique glycolipid and DNA–DNA similarity of Trepresents a novel species of the genus, for which the nameAmycolatopsis decaplaninasp. nov. (type strain, FH 1845T=DSM 44594T=NRRL B-24209T) is proposed.

Ustilago species produce an extracellular oil that shows activity in various pharmaceutical assays. We isolated several complexes of this heterogeneous glycolipid from cultures of Ustilago maydis DSM 11494 and Geotrichum candidum ST 002515, and determined the chemical structures of these new compounds, termed ustilipids, on the basis of NMR experiments, mass spectra, and fatty acid analyses. They all possess a 4-O-beta-D-mannopyranosyl D-erythritol basic framework, the configuration of which was confirmed, after initial solvolysis, by a single-crystal X-ray structure analysis. All the investigated ustilipids and related compounds are similarly constructed: the three hydroxy groups of the erythritol side chain are free in all cases, whereas the hydroxy groups of the mannose residue are for the most part acylated. Medium-chain fatty acids have for the first time been detected as components of glycolipids produced by Ustilaginales. While the 2-hydroxy group of the mannose residue is esterified with a C2-C8 carboxylate side chain, the 3-hydroxy group is in all cases esterified by a longer, C12-C20 fatty acid residue. The oxygen functionalities at the 4 and 6 positions are either acetylated or present as free hydroxy groups. Ustilipids antagonize dopamine D3 receptors in micromolar quantities; other members of this class of compounds have been found to possess an inhibitory action on the neurotensin receptor. The hemolytic activity of ustilipids is low.

Screening of Indian soils for strains producing antibiotics active against methicillin resistant staphylococci resulted in the isolation of the actinomycetes FH 1894T, ST 101170T, and FH 1893T, producing novel glycopeptide antibiotics and a polyenic compound, respectively. Studies of the cellular fatty acids and the absence of mycolic acids as well as the 16S rRNA gene sequence analysis of the producers indicated their membership to the genus Amycolatopsis. Comparison of genomic and metabolic properties of these strains with known species of this genus indicated that they represent new species for which the names Amycolatopsis balhimycina (type strain FH 1894T, DSM 44591T) and Amycolatopsis vancoresmycina (type strain ST 101170T, DSM 44592T) are proposed. The producer of the antibiotic Tolypomycin, strain IFO 14664T, representing the invalid species "Amycolatopsis tolypophorus", was also included in this investigation. As this strain was found to represent a valid species of the genus Amycolatopsis the name Amycolatopsis tolypomycina is proposed for this species, with the type strain IFO 14664T (DSM 44544T). The producer of the antibiotic Nogabecin, strain FH 1893T, was found to be closely related to the type strain of A. keratiniphila DSM 44409T which justifies the description of two subspecies of this species, A. keratiniphila subsp. keratiniphila DSM 44409T and A. keratiniphila subsp. nogabecina DSM 44586T.

A novel myxobacterium, MCy1366T (Ar1733), was isolated in 1981 from a soil sample collected from a region near Tokyo, Japan. It displayed general myxobacterial features like Gram-negative-staining, rod-shaped vegetative cells, gliding on solid surfaces, microbial lytic activity, fruiting-body-like aggregates and myxospore-like structures. The strain was mesophilic, aerobic and showed a chemoheterotrophic mode of nutrition. It was resistant to many antibiotics such as cephalosporin C, kanamycin, gentamicin, hygromycin B, polymyxin and bacitracin, and the key fatty acids of whole cell hydrolysates were iso-C15 : 0, iso-C17 : 0 and iso-C17 : 0 2-OH. The genomic DNA G+C content of the novel strain was 65.6 mol%. The 16S rRNA gene sequence showed highest similarity (97.60 %) to ‘Stigmatella koreensis’ strain KYC-1019 (GenBank accession no. EF112185). Phylogenetic analysis based on 16S rRNA gene sequences and MALDI-TOF MS data revealed a novel branch in the family Myxococcaceae . DNA–DNA hybridization showed only 28 % relatedness between the novel strain and the closest recognized species, Corallococcus exiguus DSM 14696T (97 % 16S rRNA gene sequence similarity). A recent isolate from a soil sample collected in Switzerland, MCy10622, displayed 99.9 % 16S rRNA gene sequence similarity with strain MCy1366T and showed almost the same characteristics. Since some morphological features like fruiting-body-like aggregates were barely reproducible in the type strain, the newly isolated strain, MCy10622, was also intensively studied. On the basis of a comprehensive taxonomic study, we propose a novel genus and species, Aggregicoccus edonensis gen. nov., sp. nov., for strains MCy1366T and MCy10622. The type strain of the type species is MCy1366T ( = DSM 27872T = NCCB 100468T).

The terpene peptide memnopeptide A (1), C76H108N16O18S, MW 1564, was isolated from a culture of the fungus Memnoniella echinata FH 2272 on casein peptone. The structure of the novel compound was elucidated with the aid of 2D NMR experiments and from amino acid analysis and mass spectrometric sequencing of the peptide. The compound consists of a known phenylspirodrimane subunit linked to the decapeptide Met-His-Gln-Pro-His-Gln-Pro-Leu-Pro-Pro. This proline-rich peptide is a subsequence of beta-casein. From the observed absence in the literature of any other highly significant sequence homologues, memnopeptide A can be assumed to arise from metabolic products of the fungus with direct incorporation of constituents of the nutrient medium. The formation of memnopeptide A suggests this may be a mechanism for storage of amines by the fungus. Memnopeptide A has weak antibacterial activity against gram-positive bacteria and effects half-maximal activation of sarco(endo)plasmic reticulum Ca2+ ATPase (SERCA2) at a concentration of 12.5 microM.

The novel peptide feglymycin has been isolated from cultures of Streptomyces sp. DSM 11171 by solid phase extraction, size exclusion chromatography and repeated reversed-phase chromatography. The molecular weight was found to be 1900.90 g/mol and the molecular formula is C95H97Nl3O30. Feglymycin contains 13 amino acids of which four are 3-hydroxyphenylglycine and five are 3,5-dihydroxyphenylglycine residues. The structure of the linear peptide has been determined by 1H and 13C NMR spectroscopy. The sequence was confirmed by the observed mass spectroscopic fragmentation pattern. As well as having weak antibacterial activity, feglymycin inhibits the replication of the human immunodeficiency virus (HIV) in vitro.

Three strains of Myxozyma mucilagina including the type strain were reexamined. Based on differences in their carbon utilization pattern, mobility of isoenzymes, mol% G + C of their DNA and extent of DNA complementary the new species Myxozyma neglecta is proposed.

In 2000, an actinomycete strain that showed strong antibacterial activity in culture extracts was isolated from a soil sample. The antibiotic activity corresponds to a lipopeptide complex that was named friulimycin, as the producing micro-organism was isolated from a soil sample from the region of Friaul in Italy. Taxonomic investigations showed that the producer strain belonged to a novel species of the genus Actinoplanes , for which the name Actinoplanes friuliensis was proposed. During further taxonomic studies, another antibiotic-producing isolate belonging to the genus Actinoplanes , FH 2241T, was characterized; in a patent, the name ‘Actinoplanes nipponensis’ was proposed for this strain. This organism was shown to be related to A. friuliensis . ‘A. nipponensis’ was never described in detail and the name was never validly published. Here we present a complete description of Actinoplanes nipponensis sp. Nov. (type strain FH 2241T = ATCC 31145T = DSM 43867T) and an emended description of Actinoplanes friuliensis (type strain HAG 010964T = DSM 45797T = CCUG 63250T).

A lactose-containing fermentation medium initiated the formation of 7-O-beta-D-galactosyl-brefeldin A [1] in the brefeldin A-producing organism, Penicillium brefeldianum. The detection, isolation, and physicochemical properties of 1, which has been produced by biological derivatization via transglycosylation, are described. Compound 1 is the first glycosylated brefeldin A derivative to have been prepared.

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.

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.

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.