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.
Highlights
The genus Triangularia was recently found to be polyphyletic, and its species were scattered along the phylogenetic tree of the order Sordariales [1,2]
A phylogenetic analysis based on the combination of sequences of the internal transcribed spacer region (ITS), the nuclear rDNA large subunit (LSU), and fragments of ribosomal polymerase II subunit 2 and β-tubulin genes, and was carried out including sequences of the type strain of Triangularia mangenotii and selected members of the Sordariales, with Camarops amorpha SMH 1450 as an outgroup (Table 1)
The ex-type strain of Triangularia mangenotii was located in the Naviculisporaceae clade, forming a well-supported clade (100% bs/1 pp) independent from the other lineages of the family, together with the type strains of Zopfiella marina, Z. pilifera and Z. submersa
Summary
The genus Triangularia was recently found to be polyphyletic, and its species were scattered along the phylogenetic tree of the order Sordariales [1,2]. Delimited the genus to the type species, together with other species previously placed in the genera Apiosordaria, Podospora, and Zopfiella. Triangularia karachiensis was transferred to the new genus Lundqvistomyces, since it was not located in the monophyletic clade comprising Triangularia [4]. The genus Zopfiella could so far not be correctly delimited due to the lack of type material of the type species Z. tabulata [4]. One reference strain of this species was placed with other ones producing ascospores with septate upper cell in the family Lasiosphaeriaceae, suggesting that this is the right monophyletic lineage representing the genus [3,4]. Other species of Zopfiella not located in this lineage have been transferred to other genera, e.g., Z. longicaudata and
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