Three New Derivatives of Zopfinol from Pseudorhypophila Mangenotii gen. et comb. nov.

Abstract

Triangularia mangenotti was analyzed for the production of secondary metabolites, resulting in the isolation of known zopfinol (1) and its new derivatives zopfinol B–C (2–4), the 10-membered lactones 7-O-acetylmultiplolide A (5) and 8-O-acetylmultiplolide A (6), together with sordarin (7), sordarin B (8), and hypoxysordarin (9). The absolute configuration of 1 was elucidated by the synthesis of MPTA-esters. Compound 1 showed antimicrobial activity against the Gram-positive bacteria Bacillus subtilis and Staphylococcus aureus and the fungus Mucor hiemalis. While 4 was weakly antibacterial, 3 showed stronger antibiotic activity against the Gram-positive bacteria and weak antifungal activity against M. hiemalis and Rhodotorula glutinis. We furthermore observed the cytotoxicity of 1, 3 and 4 against the mammalian cell lines KB3.1 and L929. Moreover, the new genus Pseudorhypophila is introduced herein to accommodate Triangularia mangenotii together with several species of Zopfiella—Z. marina, Z. pilifera, and Z. submersa. These taxa formed a well-supported monophyletic clade in the recently introduced family Navicularisporaceae, located far from the type species of the respective original genera, in a phylogram based on the combined dataset sequences of the internal transcribed spacer region (ITS), the nuclear rDNA large subunit (LSU), and fragments of the ribosomal polymerase II subunit 2 (rpb2) and β-tubulin (tub2) genes. Zopfiella submersa is synonymized with P. marina due to the phylogenetic and morphological similarity. The isolation of zopfinols 1–4 and sordarins 7–9 confirms the potential of this fungal order as producers of bioactive compounds and suggests these compounds as potential chemotaxonomic markers.

Corrections to recent changes in the taxonomy of the Sordariales

“…Moreover, the new genus Pseudorhypophila was introduced based on the production of the same class of compounds, i.e. zopfinol and derivatives, by members of the same monophyletic lineage (Harms et al 2021). In this later work, they observed that producers of sordarins, which are a class of natural antifungal agents, were all located in the Naviculisporaceae, supporting the introduction of this family based on molecular data by Marin-Felix et al (2020).…”

“…No sequences in Chaetomiaceae were included since no novelties were proposed in this family (Table 2). The maximum likelihood (ML) and Bayesian inference (BI) analyses including the four loci were performed as described by Harms et al (2021). The lengths of the individual alignments used in the combined dataset were 556 bp (ITS), 916 bp (LSU), 978 bp (RPB2) and 618 bp (TUB2), and the final combined alignment was 3068 bp.…”

Long-term prednisone treatment causes fungal microbiota dysbiosis and alters the ecological interaction between gut mycobiome and bacteriome in rats

“…The fungal species Triangularia mangenotii belongs to be the phylum Ascomycota . It has been reported that the relative abundance of Triangularia mangenotii decreased in heavy metal Pb–Zn contaminated soil ( Harms et al, 2021 ). However, Triangularia mangenotii and Ciliophora sp .…”

Plant-growth promoting activity of three fungal endophytes isolated from plants living in dehesas and their effect on Lolium multiflorum

“…Individual gene phylogenies were verified for conflicts before the three locus datasets were concatenated 47 , 48 . The maximum-likelihood (ML) and Bayesian inference analyses including the three loci were performed as described by Harms et al 49 . The best evolutionary model for each sequence dataset was calculated with MrModeltest v. 2.3 50 .…”