• Akanthopyrones A-D, α-Pyrones Bearing a 4-O-Methyl-β-d-glucopyranose Moiety from the Spider-Associated Ascomycete Akanthomyces novoguineensis.

      Kuephadungphan, Wilawan; Helaly, Soleiman E; Daengrot, Charuwan; Phongpaichit, Souwalak; Luangsa-Ard, Janet Jennifer; Rukachaisirikul, Vatcharin; Stadler, Marc; Helmholtz Centre for infection research, Inhoffenstr. 7, 38124 Braunschweig, Germany. (2017-07-18)
      Hypocrealean fungi have proved to be prolific bioactive metabolite producers; they have caught the attention of mycologists throughout the world. However, only a few studies on the insect and spider parasitic genus Akanthomyces have so far been carried out. In this study, we report the isolation, structural elucidation and biological activities of four unprecedented glycosylated α-pyrone derivatives, akanthopyrones A-D (1-4), from a culture of Akanthomyces novoguineensis collected in Thailand. The chemical structures of the akanthopyrones were determined by extensive 1D- and 2D-NMR, and HRMS spectroscopic analysis. Their absolute configurations were determined. Akanthopyrone A (1) exhibited weak antimicrobial activity against Bacillus subtilis DSM10 and cytotoxicity against the HeLa cell line KB-3-1, while akanthopyrone D (4) showed weak activity against Candida tenuis MUCL 29892.
    • Discovery of novel biologically active secondary metabolites from Thai mycodiversity with anti-infective potential

      Kuephadungphan, Wilawan; Macabeo, Allan Patrick G.; Luangsa-Ard, Janet Jennifer; Stadler, Marc; HZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany. (Elsevier, 2021-01-01)
      This mini-review is dedicated to the summary of results of the EU-funded Project “Golden Mycological Triangle” (acronym GoMyTri), which was carried out in collaboration of three research infrastructures in Germany, the Netherlands and Thailand during the years 2014–2018. The cooperation explored the mycological and microbiological biodiversity of Europe and Southeast Asia with regard to the search for the badly needed new antibiotics and other biologically active secondary metabolites. The project was conducted to foster international collaboration networks, know-how exchange and interdisciplinary training of young scientists. The first two years of the project were mainly dedicated to field work, and several hundreds of fungal cultures have been isolated from material mostly collected in Thailand. These fungal strains were characterized by morphological and molecular phylogenetic methods and several new taxa were discovered. The cultures underwent screening for antimicrobial and nematicidal metabolites and a number of bioactive metabolites have already been found, isolated and characterized. Several large phylogenetic studies have already been published that resulted from the project work. The results were also brought to the attention of the scientific community as well as the general public through various dissemination events. Based on the tremendous success of this project, a follow-up project application including additional partners from Africa and further European countries has recently been filed and approved, and the international, interdisciplinary collaboration will now continue in the new RISE-MSCA-Project (acronym “Mycobiomics”).
    • Five Unprecedented Secondary Metabolites from the Spider Parasitic Fungus Akanthomyces novoguineensis.

      Helaly, Soleiman E; Kuephadungphan, Wilawan; Phongpaichit, Souwalak; Luangsa-Ard, Janet Jennifer; Rukachaisirikul, Vatcharin; Stadler, Marc; Helmholtz Centre for infection research, Inhoffenstr. 7, 38124 Braunschweig, Germany. (2017-06-14)
      Five new compounds including the glycosylated β-naphthol (1, akanthol), a glycosylated pyrazine (2, akanthozine), and three amide derivatives including a hydroxamic acid derivative (3-5) were isolated from the spider-associated fungus Akanthomyces novoguineensis (Cordycipitaceae, Ascomycota). Their structures were elucidated by using high resolution mass spectrometry (HRMS) and NMR spectroscopy. In this study, the antimicrobial, cytotoxic, anti-biofilm, and nematicidal activities of the new compounds were evaluated. The distribution pattern of secondary metabolites in the species was also revealed in which more isolates of A. novoguineensis were encountered and their secondary metabolite profiles were examined using analytical HPLC with diode array and mass spectrometric detection (HPLC-DAD/MS). Remarkably, all isolated compounds are specifically produced by A. novoguineensis.
    • New nematicidal and antimicrobial secondary metabolites from a new species in the new genus, .

      Rupcic, Zeljka; Chepkirui, Clara; Hernández-Restrepo, Margarita; Crous, Pedro W; Luangsa-Ard, Janet Jennifer; Stadler, Marc; Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7, 38124 Braunschweig, Germany. (2018-01-01)
      During the course of a study on the functional biodiversity of the mycobiota inhabiting rainforests in Thailand, a fungal strain was isolated from a plant sample and shown to represent an undescribed species, as inferred from a combination of morphological and molecular phylogenetic methods. Molecular phylogenetic analyses, based on four DNA loci, revealed a phylogenetic tree with the newly generated sequences clustering in a separate branch, together with members of the Sulcatisporaceae (Pleosporales, Ascomycota). The Thai specimen morphologically resembled
    • New nematicidal and antimicrobial secondary metabolites from a new species in the new genus, .

      Rupcic, Zeljka; Chepkirui, Clara; Hernández-Restrepo, Margarita; Crous, Pedro W; Luangsa-Ard, Janet Jennifer; Stadler, Marc; Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7, 38124 Braunschweig, Germany. (2018-01-01)
      During the course of a study on the functional biodiversity of the mycobiota inhabiting rainforests in Thailand, a fungal strain was isolated from a plant sample and shown to represent an undescribed species, as inferred from a combination of morphological and molecular phylogenetic methods. Molecular phylogenetic analyses, based on four DNA loci, revealed a phylogenetic tree with the newly generated sequences clustering in a separate branch, together with members of the Sulcatisporaceae (Pleosporales, Ascomycota). The Thai specimen morphologically resembled
    • Ophiocordyceps flavida sp. nov. (Ophiocordycipitaceae), a new species from Thailand associated with Pseudogibellula formicarum (Cordycipitaceae), and their bioactive secondary metabolites

      Mongkolsamrit, Suchada; Noisripoom, Wasana; Pumiputikul, Siraphop; Boonlarppradab, Chollaratt; Samson, Robert A.; Stadler, Marc; Becker, Kevin; Luangsa-Ard, Janet Jennifer; HZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany. (Springer Nature, 2021-04-01)
      During a diversity study of entomopathogenic fungi in an agricultural ecosystem, two fungi were collected, isolated, and identified based on molecular phylogenetic analyses of three nuclear loci (LSU, TEF1, and RPB1) combined with morphological data. In this study, one novel species is described, Ophiocordyceps flavida, and a new record of Pseudogibellula formicarum for Thailand. Ophiocordyceps flavida morphologically resembles the Hirsutella anamorph of Ophiocordyceps pruinosa by having a mononematous character of the conidiophores and the same insect host (Hemiptera: Cicadellidae). Pseudogibellula formicarum is found to occur simultaneously with O. flavida, producing white conidiophores on the host. Additionally, secondary metabolites of both fungi were investigated and the major compound in O. flavida was identified as 2-[2-(4-chlorophenyl)ethyl]-2-(1,1-dimethylethyl)-oxirane. Pseudogibellula formicarum from Ghana and Thailand produces 6-methoxy-1H-indole-3-carbonitrile as a main component. These compounds are known from chemical synthesis or as products of biotransformation, respectively. However, they were obtained in our study as genuine fungal metabolites for the first time and may even constitute chemotaxonomic markers for the respective species
    • Pigmentosins from Gibellula sp. As antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

      Helaly, Soleiman E.; Kuephadungphan, Wilawan; Phainuphong, Patima; Ibrahim, Mahmoud A.A.; Tasanathai, Kanoksri; Mongkolsamrit, Suchada; Luangsa-Ard, Janet Jennifer; Phongpaichit, Souwalak; Rukachaisirikul, Vatcharin; Stadler, Marc; et al. (Beilstein Institut, 2019-12-16)
      n the course of our exploration of the Thai invertebrate-pathogenic fungi for biologically active metabolites, pigmentosin A (1) and a new bis(naphtho-α-pyrone) derivative, pigmentosin B (2), were isolated from the spider-associated fungus Gibellula sp. Furthermore, a new glycosylated asperfuran 3, together with one new (6) and two known (4 and 5) cyclodepsipeptides, was isolated from Cordyceps javanica. The pigmentosins 1 and 2 showed to be active against biofilm formation of Staphylococcus aureus DSM1104. The lack of toxicity toward the studied microorganism and cell lines of pigmentosin B (2), as well as the antimicrobial effect of pigmentosin A (1), made them good candidates for further development for use in combination therapy of infections involving biofilm-forming S. aureus. The structure elucidation and determination of the absolute configuration were accomplished using a combination of spectroscopy, including 1D and 2D NMR, HRMS, Mosher ester analysis, and comparison of calculated/experimental ECD spectra. A chemotaxonomic investigation of the secondary metabolite profiles using analytical HPLC coupled with diode array detection and mass spectrometry (HPLC–DAD–MS) revealed that the production of pigmentosin B (2) was apparently specific for Gibellula sp., while the glycoasperfuran 3 was specific for C. javanica.
    • Studies on the biologically active secondary metabolites of the new spider parasitic fungus Gibellula gamsii

      Kuephadungphan, Wilawan; Macabeo, Allan Patrick G.; Luangsa-Ard, Janet Jennifer; Tasanathai, Kanoksri; Thanakitpipattana, Donnaya; Phongpaichit, Souwalak; Yuyama, Kamila; Stadler, Marc