Hypoxylon luteogranulatum (Hypoxylaceae, Xylariales), a novel species from Thailand with distinct chemical and ecological traits

During the course of our ongoing study of the diversity of Thai fungi and their secondary metabolites, numerous specimens within the Hypoxylaceae have been characterised by traditional morphology, chemotaxonomy using ultra-high-performance liquid chromatography coupled to diode array detection and i...

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Main Authors: Sarunyou Wongkanoun, Esteban Charria-Girón, Marjorie Cedeño-Sanchez, Boonchuai Chainuwong, Sayanh Somrithipol, Eric Kuhnert, Prasert Srikitikulchai, Natapol Pornputtapong, Frank Surup, Jennifer Luangsa-ard, Marc Stadler
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Language:English
Published: Taylor & Francis Group 2025-01-01
Series:Mycology
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Online Access:https://www.tandfonline.com/doi/10.1080/21501203.2024.2435979
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author Sarunyou Wongkanoun
Esteban Charria-Girón
Marjorie Cedeño-Sanchez
Boonchuai Chainuwong
Sayanh Somrithipol
Eric Kuhnert
Prasert Srikitikulchai
Natapol Pornputtapong
Frank Surup
Jennifer Luangsa-ard
Marc Stadler
author_facet Sarunyou Wongkanoun
Esteban Charria-Girón
Marjorie Cedeño-Sanchez
Boonchuai Chainuwong
Sayanh Somrithipol
Eric Kuhnert
Prasert Srikitikulchai
Natapol Pornputtapong
Frank Surup
Jennifer Luangsa-ard
Marc Stadler
author_sort Sarunyou Wongkanoun
collection DOAJ
description During the course of our ongoing study of the diversity of Thai fungi and their secondary metabolites, numerous specimens within the Hypoxylaceae have been characterised by traditional morphology, chemotaxonomy using ultra-high-performance liquid chromatography coupled to diode array detection and ion mobility tandem mass spectrometry (UHPLC-DAD-IM-MS/MS), and molecular phylogenetic analyses. MS/MS-based analysis of the major stromatal metabolites of a newly identified taxon, Hypoxylon luteogranulatum, indicated the production of distinct compounds compared to the azaphilone and binaphthalene pigments commonly found in the Hypoxylaceae, aside from the presence of the chemotaxonomic marker binaphthalene tetrol (BNT). Further analysis suggested that one of the major metabolites had the molecular formula C13H13NO3, identical to hypoxyvermelhotin A, a yellow pigment so far exclusively found in Hypoxylon lechatii. Its identity was confirmed after purification by preparative high-performance liquid chromatography with nuclear magnetic resonance (NMR) data, and genome analysis of H. lechatii revealed the presence of different hybrid polyketide synthases-non-ribosomal peptide synthetases (PKS-NRPS) hybrid clusters. Despite chemotaxonomic similarities with H. lechatii, we propose a new species, which is morphologically distinct from H. lechatii. Our molecular phylogenetic study provides substantial evidence distinguishing H. luteogranulatum clearly from H. lechatii and allied members within the Hypoxylaceae. Additionally, future studies are needed to better understand the ecological behaviour of H. luteogranulatum and identify the ecological role of the vermelhotin-like molecules within this putative interaction.
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spelling doaj-art-8736bf94bffd4485b8d88f00fc4f09322025-01-16T08:22:24ZengTaylor & Francis GroupMycology2150-12032150-12112025-01-0111910.1080/21501203.2024.2435979Hypoxylon luteogranulatum (Hypoxylaceae, Xylariales), a novel species from Thailand with distinct chemical and ecological traitsSarunyou Wongkanoun0Esteban Charria-Girón1Marjorie Cedeño-Sanchez2Boonchuai Chainuwong3Sayanh Somrithipol4Eric Kuhnert5Prasert Srikitikulchai6Natapol Pornputtapong7Frank Surup8Jennifer Luangsa-ard9Marc Stadler10Department of Biochemistry and Microbiology, Center of Excellence for DNA Barcoding of Thai Medicinal Plants, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, ThailandDepartment of Microbial Drugs, Helmholtz Centre for Infection Research GmbH (HZI), German Centre for Infection Research Association (DZIF), Braunschweig, GermanyDepartment of Microbial Drugs, Helmholtz Centre for Infection Research GmbH (HZI), German Centre for Infection Research Association (DZIF), Braunschweig, GermanyNational Biobank of Thailand (NBT), National Center for Genetic Engineering and Biotechnology (BIOTEC), Pathum Thani, ThailandPlant Microbe Interaction Research Team (APMT), National Center for Genetic Engineering and Biotechnology (BIOTEC), Pathum Thani, ThailandGinkgo Bioworks, Inc., Boston, USANational Biobank of Thailand (NBT), National Center for Genetic Engineering and Biotechnology (BIOTEC), Pathum Thani, ThailandDepartment of Biochemistry and Microbiology, Center of Excellence for DNA Barcoding of Thai Medicinal Plants, Faculty of Pharmaceutical Sciences, Chulalongkorn University, Bangkok, ThailandDepartment of Microbial Drugs, Helmholtz Centre for Infection Research GmbH (HZI), German Centre for Infection Research Association (DZIF), Braunschweig, GermanyPlant Microbe Interaction Research Team (APMT), National Center for Genetic Engineering and Biotechnology (BIOTEC), Pathum Thani, ThailandDepartment of Microbial Drugs, Helmholtz Centre for Infection Research GmbH (HZI), German Centre for Infection Research Association (DZIF), Braunschweig, GermanyDuring the course of our ongoing study of the diversity of Thai fungi and their secondary metabolites, numerous specimens within the Hypoxylaceae have been characterised by traditional morphology, chemotaxonomy using ultra-high-performance liquid chromatography coupled to diode array detection and ion mobility tandem mass spectrometry (UHPLC-DAD-IM-MS/MS), and molecular phylogenetic analyses. MS/MS-based analysis of the major stromatal metabolites of a newly identified taxon, Hypoxylon luteogranulatum, indicated the production of distinct compounds compared to the azaphilone and binaphthalene pigments commonly found in the Hypoxylaceae, aside from the presence of the chemotaxonomic marker binaphthalene tetrol (BNT). Further analysis suggested that one of the major metabolites had the molecular formula C13H13NO3, identical to hypoxyvermelhotin A, a yellow pigment so far exclusively found in Hypoxylon lechatii. Its identity was confirmed after purification by preparative high-performance liquid chromatography with nuclear magnetic resonance (NMR) data, and genome analysis of H. lechatii revealed the presence of different hybrid polyketide synthases-non-ribosomal peptide synthetases (PKS-NRPS) hybrid clusters. Despite chemotaxonomic similarities with H. lechatii, we propose a new species, which is morphologically distinct from H. lechatii. Our molecular phylogenetic study provides substantial evidence distinguishing H. luteogranulatum clearly from H. lechatii and allied members within the Hypoxylaceae. Additionally, future studies are needed to better understand the ecological behaviour of H. luteogranulatum and identify the ecological role of the vermelhotin-like molecules within this putative interaction.https://www.tandfonline.com/doi/10.1080/21501203.2024.2435979Phylogenytetramic acidsmetabolomicsgenome miningSordariomycetes: new speciesXylariales
spellingShingle Sarunyou Wongkanoun
Esteban Charria-Girón
Marjorie Cedeño-Sanchez
Boonchuai Chainuwong
Sayanh Somrithipol
Eric Kuhnert
Prasert Srikitikulchai
Natapol Pornputtapong
Frank Surup
Jennifer Luangsa-ard
Marc Stadler
Hypoxylon luteogranulatum (Hypoxylaceae, Xylariales), a novel species from Thailand with distinct chemical and ecological traits
Mycology
Phylogeny
tetramic acids
metabolomics
genome mining
Sordariomycetes: new species
Xylariales
title Hypoxylon luteogranulatum (Hypoxylaceae, Xylariales), a novel species from Thailand with distinct chemical and ecological traits
title_full Hypoxylon luteogranulatum (Hypoxylaceae, Xylariales), a novel species from Thailand with distinct chemical and ecological traits
title_fullStr Hypoxylon luteogranulatum (Hypoxylaceae, Xylariales), a novel species from Thailand with distinct chemical and ecological traits
title_full_unstemmed Hypoxylon luteogranulatum (Hypoxylaceae, Xylariales), a novel species from Thailand with distinct chemical and ecological traits
title_short Hypoxylon luteogranulatum (Hypoxylaceae, Xylariales), a novel species from Thailand with distinct chemical and ecological traits
title_sort hypoxylon luteogranulatum hypoxylaceae xylariales a novel species from thailand with distinct chemical and ecological traits
topic Phylogeny
tetramic acids
metabolomics
genome mining
Sordariomycetes: new species
Xylariales
url https://www.tandfonline.com/doi/10.1080/21501203.2024.2435979
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