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

doi:10.3390/molecules22060991

Cited by 19 publications

(19 citation statements)

References 28 publications

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“…Invertebrate-pathogenic fungi, in particular the spider-pathogenic fungi, have recently proved to be a promising source of bioactive compounds [8][9][10]. Thus, during the current study, which is part of a project aiming to discover novel biofilm inhibitors from Thai fungi [11], a number of invertebrate-pathogenic fungi collected from various parts of Thailand were studied for production of bioactive secondary metabolites.…”

Section: Introductionmentioning

confidence: 99%

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

Helaly¹,

Kuephadungphan²,

Phainuphong³

et al. 2019

Beilstein J. Org. Chem.

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In 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.

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Section: Introductionmentioning

confidence: 99%

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

Helaly¹,

Kuephadungphan²,

Phainuphong³

et al. 2019

Beilstein J. Org. Chem.

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“…Biological activities of secondary metabolites from a diverse range of microorganisms have been demonstrated in many studies. Many studies have been done on the secondary metabolites of some antagonistic fungi and many antimicrobial compounds have been identified (Helaly et al, 2017;Richter et al, 2016;Surup et al, 2017).…”

Section: Introductionmentioning

confidence: 99%

Cytotoxic, antimicrobial and antiviral secondary metabolites produced by the plant pathogenic fungus Cytospora sp. CCTU A309

et al. 2019

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Chemical analysis of extracts from cultures of the plant pathogenic fungus Cytospora sp. strain CCTU A309 collected in Iran led to the isolation of two previously unreported heptanedioic acid derivatives namely (2R,3S) 2-hydroxy-3-phenyl-4-oxoheptanedioic acid (1) and (2S,3S) 2-hydroxy-3-phenyl-4-oxoheptanedioic acid (2) as diastereomers, four previously undescribed prenylated p-terphenyl quinones 3-6 in addition to five known metabolites. Their structures were elucidated on the basis of extensive spectroscopic analysis and highresolution mass spectrometry. While the relative configurations of 1 and 2 were reasoned by a J-based analysis and confirmed by comparison of 13 C chemical shifts to literature data, their absolute configurations were deduced from comparison of the 1 H NMR difference of their (S)-and (R)-phenylglycine methyl ester derivatives. The isolated compounds were tested for their cytotoxic, antimicrobial, biofilm inhibition, antiviral, and nematicidal activities. While only moderate antimicrobial effects were observed, the terphenyl quinone derivatives 3-6 and leucomelone (10) exhibited significant cytotoxicity against the mouse fibroblast L929 and cervix carcinoma KB-3-1 cell lines with IC 50 values ranging from 2.4 to 26 µg/mL. Furthermore, metabolites 4-6 showed interesting antiviral activity against hepatitis C virus (HCV).

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“…The minimum inhibitory concentrations (MICs) of alkaloids 1 and 2 against Bacillus subtilis DSM10, Escherichia coli DSM498, Candida tenuis MUCL29892, and Mucor plumbeus MUCL49355 were determined using a broth microdilution method previously described by Kuephadungphan et al (2017). Their nematicidal activity against Caenorhabditis elegans and anti-biofilm activity against Staphylococcus aureus DSM1104 (ATCC25923) as well as Pseudomonas aeruginosa PA14 were also investigated using the protocols according to Helaly et al (2017) and Chepkirui et al (2018). The cytotoxicity assay was performed on mouse fibroblast (L929), HeLa (KB3.1), human breast adenocarcinoma (MCF-7), human prostate cancer (PC-3), squamous carcinoma (A431), human lung carcinoma(A549), and ovarian carcinoma (SKOV-3) cell lines using a 5-day MTT assay and IC 50 values were expressed in micrograms per milliliter (Chepkirui et al 2017).…”

Section: Biological Activity Screeningmentioning

confidence: 99%

Studies on the biologically active secondary metabolites of the new spider parasitic fungus Gibellula gamsii

et al. 2018

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Numerous gatherings of a new species of the genus Gibellula, closely resembling the monotypic, neotropical G. mirabilis were encountered in Thailand. The taxon was cultured successfully although no in vitro sporulation was observed. The new species, Gibellula gamsii, could be distinguished from closely related other Gibellula species on the basis of morphological features and phylogenetic inferences recruiting concatenated sequences of five DNA loci including ITS, LSU, RPB1, RPB2, and EF1-α. The secondary metabolites of G. gamsii, strain BCC47868, were studied concurrently after preparative separation of the crude extract by preparative high-performance liquid chromatography (HPLC). Two new 1,3-disubstituted β-carboline alkaloids, for which we propose the trivial names, gibellamines A (1) and B (2), were isolated. The chemical structures of these compounds were elucidated by interpretation of spectral data, generated by nuclear magnetic resonance spectroscopy (NMR) and mass spectrometry (MS). The alkaloid 1 also exhibited moderate anti-biofilm activity against Staphylococcus aureus.

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Five Unprecedented Secondary Metabolites from the Spider Parasitic Fungus Akanthomyces novoguineensis

Cited by 19 publications

References 28 publications

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

Pigmentosins from Gibellula sp. as antibiofilm agents and a new glycosylated asperfuran from Cordyceps javanica

Cytotoxic, antimicrobial and antiviral secondary metabolites produced by the plant pathogenic fungus Cytospora sp. CCTU A309

Studies on the biologically active secondary metabolites of the new spider parasitic fungus Gibellula gamsii

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