Pullularins E and F, two new peptides from the endophytic fungus Bionectria ochroleuca isolated from the mangrove plant Sonneratia caseolaris

Acknowledgements This project was supported by grants of the BMBF (to P.P.) and MOST (to W.L.). We wish to thank W.E.G. Müller (Johannes-Gutenberg-University, Mainz, Germany) for carrying out the cytotoxicity assay. A scholarship (Grant No. 10/6/117) granted and financed by the Egyptian Government (Ministry of High Education) to W.E. is gratefully acknowledged.Peer reviewedPublisher PD

New Natural Product from Botryosphaeria australis, an Endophyte from Mangrove Avicennia marina

Chemical investigation of the endophytic fungus Botryosphaeria australis isolated from Avicennia marina originally from Hainan Province, P.R. China, yielded a new compound botryosphaenin (1), from the class of napthoquinone, together with 5 known compounds, botryosterpene (2) and 5-hydroxy-2,7-dimethoxynaphthalene-1,4-dione (3) and its derivatives, 6-ethyl-5-hydroxy-2,7-dimethoxynaphthalene-1,4-dione (4), O-methylaspmenone (5), O-methylasparvenone (6) and 5-(carboxymethyl)-7-hydroxy-1,4a-dimethyl-6-methylene decahydron aphthalene-1-carboxylic acid (7). Their structures were determined on the basis of spectroscopic methods including 1D (1H, 13C, and DEPT) and 2D (COSY, HMQC, HMBC, and ROESY) NMR experiments and by mass spectroscopic measurements The new compounds, 1 showed activity against the bacterial pathogens Staphylococcus aureus, several Streptococcus species and Bacillus subtilis, but also against the eukaryotic cell lines THP-1 (human leukemia monocyte) and BALB/3T3 (mouse embryonic fibroblast)

Enhancement of botrallin and TMC-264 production in liquid culture of endophytic fungus Hyalodendriella sp. Ponipodef12 after treatments with metal ions

Background: Hyalodendriella sp. Ponipodef12, an endophytic fungus from a poplar hybrid, was a high producer of botrallin and TMC-264 with various bioactivities. In this study, the influences of eight metal ions (i.e., Mn2+, Na+, Mg2+, Zn2+, Cu2+, Fe2+, Fe3+ and Al3+) on botrallin and TMC-264 production in liquid culture of the endophytic fungus Hyalodendriella sp. Ponipodef12 were investigated. Results: Three most effective metal ions (Zn2+, Cu2+ and Mg2+) along with their optimum concentrations were screened. The optimum addition time and concentrations of Zn2+, Cu2+ and Mg2+ were further obtained respectively for improving botrallin and TMC-264 production. The combination effects of Zn2+, Cu2+ and Mg2+ on the production of botrallin and TMC-264 by employing statistical method based on the central composite design (CCD) and response surface methodology (RSM) were evaluated, and two quadratic predictive models were developed for botrallin and TMC-264 production. The yields of botrallin and TMC-264, which were predicted as 144.12 mg/L and 36.04 mg/L respectively, were validated to be 146.51 mg/L and 36.63 mg/L accordingly with the optimum concentrations of Zn2+ at 0.81 mmol/L, Cu2+ at 0.20 mmol/L, and Mg2+ at 0.13 mmol/L in medium. Conclusion: The results indicated that the enhancement of botrallin and TMC-264 accumulation in liquid culture of the endophytic fungus Hyalodendriella sp. Ponipodef12 by the metal ions and their combination should be an effective strategy

Secondary Metabolites from Acremonium Fungi: Diverse Structures and Bioactivities

Background: Acremonium fungi have been isolated from various sources, such as soil, plants, and marine organisms. Method: The species in Acremonium have been proved to be rich sources of novel and bioactive secondary metabolites. Up to now, 356 metabolites belonging to steroids (6 compounds), terpenoids (86), meroterpenoids (66), polyketides (89), alkaloids (28), peptides (75), and miscellaneous types (6) have been isolated from Acremonium fungi. These metabolites displayed a wide range of biological activities including antimicrobial, cytotoxic, antitumor, immunosuppressive, antioxidant, antiinflammatory, antimalarial, phytotoxic, tremorgenic, antiviral, neuritogenic, insecticidal and enzymesinhibiting activities. Conclusion: This review highlights the structures and bioactivities of the secondary metabolites from Acremonium fungi reported until July 2016

Structural Diversity and Biological Activities of Cyclic Depsipeptides from Fungi

Cyclic depsipeptides (CDPs) are cyclopeptides in which amide groups are replaced by corresponding lactone bonds due to the presence of a hydroxylated carboxylic acid in the peptide structure. These peptides sometimes display additional chemical modifications, including unusual amino acid residues in their structures. This review highlights the occurrence, structures and biological activities of the fungal CDPs reported until October 2017. About 352 fungal CDPs belonging to the groups of cyclic tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, and tridecadepsipeptides have been isolated from fungi. These metabolites are mainly reported from the genera Acremonium, Alternaria, Aspergillus, Beauveria, Fusarium, Isaria, Metarhizium, Penicillium, and Rosellina. They are known to exhibit various biological activities such as cytotoxic, phytotoxic, antimicrobial, antiviral, anthelmintic, insecticidal, antimalarial, antitumoral and enzyme-inhibitory activities. Some CDPs (i.e., PF1022A, enniatins and destruxins) have been applied as pharmaceuticals and agrochemicals

Structural Diversity and Biological Activities of Fungal Cyclic Peptides, Excluding Cyclodipeptides

Cyclic peptides are cyclic compounds formed mainly by the amide bonds between either proteinogenic or non-proteinogenic amino acids. This review highlights the occurrence, structures and biological activities of fungal cyclic peptides (excluding cyclodipeptides, and peptides containing ester bonds in the core ring) reported until August 2017. About 293 cyclic peptides belonging to the groups of cyclic tri-, tetra-, penta-, hexa-, hepta-, octa-, nona-, deca-, undeca-, dodeca-, tetradeca-, and octadecapeptides as well as cyclic peptides containing ether bonds in the core ring have been isolated from fungi. They were mainly isolated from the genera Aspergillus, Penicillium, Fusarium, Acremonium and Amanita. Some of them were screened to have antimicrobial, antiviral, cytotoxic, phytotoxic, insecticidal, nematicidal, immunosuppressive and enzyme-inhibitory activities to show their potential applications. Some fungal cyclic peptides such as the echinocandins, pneumocandins and cyclosporin A have been developed as pharmaceuticals

Structural Diversity and Biological Activities of the Cyclodipeptides from Fungi

Cyclodipeptides, called 2,5-diketopiperazines (2,5-DKPs), are obtained by the condensation of two amino acids. Fungi have been considered to be a rich source of novel and bioactive cyclodipeptides. This review highlights the occurrence, structures and biological activities of the fungal cyclodipeptides with the literature covered up to July 2017. A total of 635 fungal cyclodipeptides belonging to the groups of tryptophan-proline, tryptophan-tryptophan, tryptophan–Xaa, proline–Xaa, non-tryptophan–non-proline, and thio-analogs have been discussed and reviewed. They were mainly isolated from the genera of Aspergillus and Penicillium. More and more cyclodipeptides have been isolated from marine-derived and plant endophytic fungi. Some of them were screened to have cytotoxic, phytotoxic, antimicrobial, insecticidal, vasodilator, radical scavenging, antioxidant, brine shrimp lethal, antiviral, nematicidal, antituberculosis, and enzyme-inhibitory activities to show their potential applications in agriculture, medicinal, and food industry

Natural Dibenzo-α-Pyrones and Their Bioactivities

Natural dibenzo-α-pyrones are an important group of metabolites derived from fungi, mycobionts, plants and animal feces. They exhibit a variety of biological activities such as toxicity on human and animals, phytotoxicity as well as cytotoxic, antioxidant, antiallergic, antimicrobial, antinematodal, and acetylcholinesterase inhibitory properties. Dibenzo-α-pyrones are biosynthesized via the polyketide pathway in microorganisms or metabolized from plant-derived ellagitannins and ellagic acid by intestinal bacteria. At least 53 dibenzo-α-pyrones have been reported in the past few decades. This mini-review aims to briefly summarize the occurrence, biosynthesis, biotransformation, as well as their biological activities and functions. Some considerations related to synthesis, production and applications of dibenzo-α-pyrones are also discussed

Metabolites from Clonostachys Fungi and Their Biological Activities

Clonostachys (teleomorph: Bionectria) fungi are well known to produce a variety of secondary metabolites with various biological activities to show their pharmaceutical and agrochemical applications. Up to now, at least 229 secondary metabolites, mainly including 84 nitrogen-containing metabolites, 85 polyketides, 40 terpenoids, and 20 other metabolites, have been reported. Many of these compounds exhibit biological activities, such as cytotoxic, antimicrobial, antileishmanial, antimalarial activities. This mini-review aims to summarize the diversity of the secondary metabolites as well as their occurrences in Clonostachys fungi and biological activities