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Cited by 316Steroid Chemistry and BiochemistryFungal and yeast genetics researchYeasts and Rust Fungi Studies

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Phylogenetic Distribution of Fungal Sterols

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Weete, John D., Abril, Maritza, Blackwell, Meredith·2010·PLoS ONE
DOI 10.1371/journal.pone.0010899PMC PMC2878339
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Abstract

BACKGROUND: Ergosterol has been considered the "fungal sterol" for almost 125 years; however, additional sterol data superimposed on a recent molecular phylogeny of kingdom Fungi reveals a different and more complex situation. METHODOLOGY/PRINCIPAL FINDINGS: The interpretation of sterol distribution data in a modern phylogenetic context indicates that there is a clear trend from cholesterol and other Delta(5) sterols in the earliest diverging fungal species to ergosterol in later diverging fungi. There are, however, deviations from this pattern in certain clades. Sterols of the diverse zoosporic and zygosporic forms exhibit structural diversity with cholesterol and 24-ethyl -Delta(5) sterols in zoosporic taxa, and 24-methyl sterols in zygosporic fungi. For example, each of the three monophyletic lineages of zygosporic fungi has distinctive major sterols, ergosterol in Mucorales, 22-dihydroergosterol in Dimargaritales, Harpellales, and Kickxellales (DHK clade), and 24-methyl cholesterol in Entomophthorales. Other departures from ergosterol as the dominant sterol include: 24-ethyl cholesterol in Glomeromycota, 24-ethyl cholest-7-enol and 24-ethyl-cholesta-7,24(28)-dienol in rust fungi, brassicasterol in Taphrinales and hypogeous pezizalean species, and cholesterol in Pneumocystis. CONCLUSIONS/SIGNIFICANCE: Five dominant end products of sterol biosynthesis (cholesterol, ergosterol, 24-methyl cholesterol, 24-ethyl cholesterol, brassicasterol), and intermediates in the formation of 24-ethyl cholesterol, are major sterols in 175 species of Fungi. Although most fungi in the most speciose clades have ergosterol as a major sterol, sterols are more varied than currently understood, and their distribution supports certain clades of Fungi in current fungal phylogenies. In addition to the intellectual importance of understanding evolution of sterol synthesis in fungi, there is practical importance because certain antifungal drugs (e.g., azoles) target reactions in the synthesis of ergosterol. These findings also invalidate use of ergosterol as an indicator of biomass of certain fungal taxa (e.g., Glomeromycota). Data from this study are available from the Assembling the Fungal Tree of Life (AFTOL) Structural and Biochemical Database: http://aftol.umn.edu.

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Figures

Figure 1 Structures of main fungal sterols. (A) Cholesterol (B) Lanosterol (C) Brassicasterol (D) Ergosterol (E) 24-Ethyl cholesterol and (F) 24-Methyl cholesterol.
Figure 1 Structures of main fungal sterols. (A) Cholesterol (B) Lanosterol (C) Brassicasterol (D) Ergosterol (E) 24-Ethyl cholesterol and (F) 24-Methyl cholesterol.CC BY · PubMed Central
Figure 2 Fungal phylogenetic tree based on James et al. (2006), White et al. (2006), and Hibbett et al. (2007), and major sterols associated with each taxon. The zygosporic fungi are indicated by flagellated cell diagrams and zygosporic fungi, by zygospore diagrams. Filled squares indicate the predominant sterol present within a terminal taxon (usually a phylum). Distinctive sterols are present in some clades within phyla: 1 Erysiphales; 2 Tuber and Terfezia also contain some ergosterol; 3 Pneumocystis; 4 Schizosaccharomyces; 5 Taphrina and Protomyces; 6 several core polypores; 7 Pucciniales; 8 one member of Mucorales reported to contain 22-dihydroergosterol; 9 several members of Mucorales contain episterol; 10 Kickxellales; 11 Most members of Entomophthorales contain 24-methyl cholesterol although several are known to have cholesterol or 24-methylene cholesterol or mixtures of 24-methyl cholesterol and 24-methylene cholesterol; 12 Catenaria anguillulae; 13 Allomyces macrogynus; 14 most species of Chytridiales tested; 15 Rhizophydium sphaerotheca; 16 only Spizellomyces punctatum sampled; 17 only Monoblepharella sp. sampled. Mesomycetozoa (Mendoza et al. 2002) is considered to be the sister group to fungi, and this group is poorly sampled. Note that many clades are undersampled or completely unsampled (see text for details).
Figure 2 Fungal phylogenetic tree based on James et al. (2006), White et al. (2006), and Hibbett et al. (2007), and major sterols associated with each taxon. The zygosporic fungi are indicated by flagellated cell diagrams and zygosporic fungi, by zygospore diagrams. Filled squares indicate the predominant sterol present within a terminal taxon (usually a phylum). Distinctive sterols are present in some clades within phyla: 1 Erysiphales; 2 Tuber and Terfezia also contain some ergosterol; 3 Pneumocystis; 4 Schizosaccharomyces; 5 Taphrina and Protomyces; 6 several core polypores; 7 Pucciniales; 8 one member of Mucorales reported to contain 22-dihydroergosterol; 9 several members of Mucorales contain episterol; 10 Kickxellales; 11 Most members of Entomophthorales contain 24-methyl cholesterol although several are known to have cholesterol or 24-methylene cholesterol or mixtures of 24-methyl cholesterol and 24-methylene cholesterol; 12 Catenaria anguillulae; 13 Allomyces macrogynus; 14 most species of Chytridiales tested; 15 Rhizophydium sphaerotheca; 16 only Spizellomyces punctatum sampled; 17 only Monoblepharella sp. sampled. Mesomycetozoa (Mendoza et al. 2002) is considered to be the sister group to fungi, and this group is poorly sampled. Note that many clades are undersampled or completely unsampled (see text for details).CC BY · PubMed Central
Figure 3 Diagram of the five predominant end products of sterol biosynthesis in fungi. Cholesterol, ergosterol (the primary sterol in many groups of fungi), 24-methyl cholesterol, 24-ethyl cholesterol, and brassicasterol and intermediates in the formation of 24-ethyl cholesterol, as major sterols reported in 175 fungal species across the kingdom Fungi.
Figure 3 Diagram of the five predominant end products of sterol biosynthesis in fungi. Cholesterol, ergosterol (the primary sterol in many groups of fungi), 24-methyl cholesterol, 24-ethyl cholesterol, and brassicasterol and intermediates in the formation of 24-ethyl cholesterol, as major sterols reported in 175 fungal species across the kingdom Fungi.CC BY · PubMed Central

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Research works printed but not linked: 2

  1. C Tanret, 1889, Sur un nouveau principle immediate de l'ergot deseigle ergosterine., C.R. Seances Acad Sci, 108, 98
  2. P Singh, 1966, Occurrence of 22-Dihydroergosterol in Polyporus pargamenus., Curr Sci, 20, 515

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Metadata

Authors
Weete, J. D., Abril, M., & Blackwell, M.
Affiliations
Louisiana State University (US)
Corresponding author
Blackwell, Meredith
ORCID
Venue
PLoS ONE
Publisher
Public Library of Science (PLoS)
Published
2010-05-28
Volume
5
Issue
5
Pages
e10899
ISSN
1932-6203 (ISSN-L)
DOI
10.1371/journal.pone.0010899
PMC
PMC2878339
OpenAlex
W2043642851
Cited by
316
References
37
Citations by year
2026: 23 · 2025: 25 · 2024: 23 · 2023: 28 · 2022: 25 · 2021: 22 · 2020: 36 · 2019: 28 · 2018: 22 · 2017: 18 · 2016: 12 · 2015: 13 · 2014: 9 · 2013: 8 · 2012: 12
FWCI
4.17
Type
journal article
Language
en
Open access
Licence
Locations
  • PLoS ONE (publishedVersion, cc-by)
  • PubMed Central (publishedVersion, cc-by)
  • PubMed (publishedVersion)
  • DOAJ (DOAJ: Directory of Open Access Journals) (submittedVersion, cc-by-sa)
Funders
National Science Foundation (0732671)
Topics
  • Physical Sciences › Chemistry › Organic Chemistry › Steroid Chemistry and Biochemistry
  • Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Fungal and yeast genetics research
  • Life Sciences › Immunology and Microbiology › Microbiology › Yeasts and Rust Fungi Studies
Keywords
fungal sterols, ergosterol, sterol biosynthesis, fungal phylogeny, cholesterol, brassicasterol, rust fungi, Glomeromycota, zoosporic fungi, azole antifungals
MeSH terms
Fungi, Phylogeny, Seawater, Sterols

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