ArticleArchives of biochemistry and biophysics2015
Pityriazepin and other potent AhR ligands isolated from Malassezia furfur yeast.
Article in Archives of biochemistry and biophysics, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 24 papers.
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Who cites it
24 citing papers in PubMed.
- Chemistry and Biological Activity of 11Molecules (Basel, Switzerland) · 2026Review
- The aryl hydrocarbon receptor: structure, signaling, physiology and pathology.Signal transduction and targeted therapy · 2026Review
- The role of the AHR in host-pathogen interactions.Nature reviews. Immunology · 2025Review
- Synthesis and Evaluation of the AhR Activity of Indolo[3,2Molecules (Basel, Switzerland) · 2025Article
- Anti-Microorganisms · 2023Review
- Review
- An insight into the recent developments in anti-infective potential of indole and associated hybrids.Journal of molecular structure · 2022Review
- Article
- Urinary metabolomic profiling from spontaneous tolerant kidney transplanted recipients shows enrichment in tryptophan-derived metabolites.EBioMedicine · 2022Article
- Review
- Gut microbiota-derived tryptophan metabolism mediates renal fibrosis by aryl hydrocarbon receptor signaling activation.Cellular and molecular life sciences : CMLS · 2021Review
- Recent Advances in the Synthesis of β-Carboline Alkaloids.Molecules (Basel, Switzerland) · 2021Review
- Aryl Hydrocarbon Receptor (AHR) Ligands as Selective AHR Modulators (SAhRMs).International journal of molecular sciences · 2020Review
- Retracted Article: The synthesis and biological activity of marine alkaloid derivatives and analogues.RSC advances · 2020Article
- Ah receptor ligands and their impacts on gut resilience: structure-activity effects.Critical reviews in toxicology · 2020Review
- A Biomimetic, One-Step Transformation of Simple Indolic Compounds toChemical research in toxicology · 2019Article
- Microbiota Metabolism Promotes Synthesis of the Human Ah Receptor Agonist 2,8-Dihydroxyquinoline.Journal of proteome research · 2019Article
- The mammalian mycobiome: A complex system in a dynamic relationship with the host.Wiley interdisciplinary reviews. Systems biology and medicine · 2019Review
- Diverse Secondary Metabolites from the Marine-Derived Fungus Dichotomomyces cejpii F31-1.Marine drugs · 2017Article
- Skin Fungi from Colonization to Infection.Microbiology spectrum · 2017Review
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Authors and funding
6 authors.
Funding
Abstract
Malassezia furfur yeast strains isolated from diseased human skin preferentially biosynthesize indole alkaloids which can be detected in the human skin and are highly potent activators of the aryl hydrocarbon receptor (AhR) and AhR-dependent gene expression. Chemical analysis of an EtOAc extract of a M. furfur strain obtained from diseased human skin and grown on l-tryptophan agar revealed several known AhR active tryptophan metabolites along with a previously unidentified compound, pityriazepin. While its structure resembled that of the known alkaloid pityriacitrin, the comprised pyridine ring had been transformed into an azepinone. The indoloazepinone scaffold of pityriazepin is extremely rare in nature and has only been reported once previously. Pityriazepin, like the other isolated compounds, was found to be a potent activator of the AhR-dependent reporter gene assay in recombinant cell lines derived from four different species, although significant species differences in relative potency were observed. The ability of pityriazepin to competitively bind to the AhR and directly stimulate AhR DNA binding classified it as a new naturally-occurring potent AhR agonist. M. furfur produces an expanded collection of extremely potent naturally occurring AhR agonists, which produce their biological effects in a species-specific manner.
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