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1.
Figure 2.

Figure 2. From: Cloning and Expression Analysis of Bioluminescence Genes in Omphalotus guepiniiformis Reveal Stress-Dependent Regulation of Bioluminescence.

Amino acid sequence identity and similarity matrices of bioluminescence pathway genes in the species of the Omphalotus lineage. The pairwise amino acid sequence identities and similarities of hispidin synthase (HispS), hispidin-3-hydroxylase (H3H), and luciferase (Luz) of the fungal species in the Omphalotus lineage, including Omphalotus guepiniiformis, were calculated in Sequence Identity and Similarity (http://imed.med.ucm.es/Tools/sias.html) using the sequence alignment obtained by Clustal Omega (https://www.ebi.ac.uk/Tools/msa/clustalo/). The percent identities and similarities were presented on the upper right and the bottom left, respectively. Og, O. guepiniiformis; Oo, O. olearius; Ng, Neonothopanus gardneri; Nn, N. nambi.

Mi-Jeong Park, et al. Mycobiology. 2024;52(1):42-50.
2.
Figure 2

Figure 2. From: Microbial and Plant Derived Low Risk Pesticides Having Nematocidal Activity.

Metabolites produced by Lachnum papyraceum and in part also from Gilmaniella humicola (2234, 3537, 3841, 4245, and 47) and by Omphalotus olearius (4850).

Antonio Evidente. Toxins (Basel). 2022 Dec;14(12):849.
3.
Figure 4

Figure 4. From: Genomic and transcriptomic analyses reveal differential regulation of diverse terpenoid and polyketides secondary metabolites in Hericium erinaceus.

Unrooted Neighbor-Joining phylogram of sesquiterpene synthase (STS) of Hericium erinaceus were constructed based homologous protein sequences. STS from Coprinopsis cinereus (Cop), Omphalotus olearius (Omp), Fomitopsis pinicola (Fompi1), Stereum hirsutum (Sh) and the single STS described from Armillaria gallica (Armga1) and Boreostereum vibrans (SqtB) are labeled. Detail information of the sequences used in phylogram can be found in Supplement Table .

Juan Chen, et al. Sci Rep. 2017;7:10151.
4.
Figure 5

Figure 5. From: Ectomycorrhizal Influence on the Dynamics of Sesquiterpene Release by Tricholoma vaccinum.

Phylogenetic clustering of putative basidiomycete sesquiterpene synthases. The protein sequences identified from the T. vaccinum genome are labeled in red; conceptually translated protein sequences of other basidiomycetes are from Antrodia cinnamomea, Armillaria gallica, Boreostereum vibrans, Coprinopsis cinerea, Coniophora puteana, Fomitopsis pinicola, Lignosus rhinoceros, Omphalotus olearius, Stereum hirsutum, and Schizophyllum commune; gene identifiers are given in brackets if no protein names are available.

Marycolette Ndidi Ezediokpu, et al. J Fungi (Basel). 2022 Jun;8(6):555.
5.
Figure 2

Figure 2. Phylogenetic analysis of sesquiterpene synthase homologs. From: Mushroom hunting using bioinformatics: Application of a predictive framework facilitates the selective identification of sesquiterpene synthases in Basidiomycota.

Sesquiterpene synthase homologs from Coprinus cinereus (Cop), Omphalotus olearius (Omp) and Stereum hirsutum (Stehi1) are labeled. A) Sesquiterpene synthases form distinct clades in an unrooted neighbor-joining phylogram. Clade III, described previously,[] is highlighted with a box. Gene accession numbers highlighted with a circle indicate cloned and characterized sesquiterpene synthases. B) An unrooted neighbor-joining tree of members of Clade III. Branches are labeled with their bootstrap values. Gene accession numbers highlighted in bold indicate cloned and characterized sesquiterpene synthases.

Maureen B. Quin, et al. Chembiochem. ;14(18):10.1002/cbic.201300349.
6.
Fig. 3

Fig. 3. From: Exploring fungal RiPPs from the perspective of chemical ecology.

Fungal RiPP-producers with presumed roles in defence. A Amanita phalloides [], B A lupin leaf showing symptoms of Phomopsis leptostromiformis infection [], C Omphalotus olearius [], D False smut disease symptoms on rice following Ustilaginoidea virens infection []. Permission to reproduce figures from the publishers of Kaya et al. (2013) (Elsevier); Bal et al. (2016) (Taylor & Francis), Lin et al. (2018) (Springer Nature) and Cowley et al. (2012) (Taylor & Francis)

R. E. Ford, et al. Fungal Biol Biotechnol. 2022;9:12.
7.
Figure 2

Figure 2. From: Draft genome of Omphalotus olearius provides a predictive framework for sesquiterpenoid natural product biosynthesis in Basidiomycota.

Time course of sesquiterpene production by O. olearius. Volatile metabolites produced by liquid cultures of O. olearius were sampled by solid phase microextraction (SPME) and analyzed by Gas Chromatography-Mass Spectrometry (GC-MS). Identified sesquiterpene compounds are numbered and structures are shown for each compound (see for compound mass spectra). One major sesquiterpene product and many small terpene peaks could not be conclusively identified. See also . Genome assembly statistics and associated data can be found in and .

Grayson T. Wawrzyn, et al. Chem Biol. ;19(6):772-783.
8.
Figure 7

Figure 7. Phylogenetic analysis of putative Δ-6 protoilludene-associated P450 monooxygenase homologs. From: Mushroom hunting using bioinformatics: Application of a predictive framework facilitates the selective identification of sesquiterpene synthases in Basidiomycota.

An unrooted neighbor-joining tree of P450 monoxygenase homologs from the Omphalotus olearius (Omp) and Stereum hirsutum (Stehi1) Δ-6 protoilludene synthase associated biosynthetic gene clusters. Branches are labeled with their bootstrap values. P450 labeling is consistent with that of and previously described biosynthetic gene clusters.[] (Note that Stehi|25180 -i and -j appear to result from a gene duplication event (, )).

Maureen B. Quin, et al. Chembiochem. ;14(18):10.1002/cbic.201300349.
9.
Figure 4

Figure 4. From: Draft genome of Omphalotus olearius provides a predictive framework for sesquiterpenoid natural product biosynthesis in Basidiomycota.

Proposed cyclization pathways leading to O. olearius sesquiterpene products. Ionization of FPP results in a primary carbocation from (E,E)-FPP that can either undergo two different ring closures (1,10 or 1,11) or is isomerized to a secondary carbocation from (3R)-NPP, which can undergo four different ring closures (1,6; 1,7; 1,10 or 1,11). Shown are pathways leading to major sesquiterpene products identified in the culture headspace of O. olearius (pentalenene 1, Δ-6 protoilludene 2, african-2-ene 3, african-3-ene 4, α-barbatene 5, δ-cadinene 7, and trans-dauca-4(11),8-diene 8) and synthesized by recombinant Omp sesquiterpene synthases (Δ-6 protoilludene 2, α-barbatene 5, δ-cadinene 7, trans-dauca-4(11),8-diene 8, α-muurolene 9, β-elemene 10, γ-cadinene 13, and daucene 14) (see for compound mass spectra). Also shown is the cyclization pathway leading to α-cuprenene 15 synthesized by sesquiterpene synthase Fompi1 cloned from Fomitopsis pinicola.

Grayson T. Wawrzyn, et al. Chem Biol. ;19(6):772-783.
10.
Figure 1

Figure 1. From: Draft genome of Omphalotus olearius provides a predictive framework for sesquiterpenoid natural product biosynthesis in Basidiomycota.

The following sesquiterpenoid compounds have been isolated from O. olearius and are proposed to be derived from the Δ-6 protoilludene scaffold: Illudin A and B, illudalenol (); illudin C,D,E (); illudosin (); dihydroilludin (); 4α-Hydroxyilludin M (); neoilludol (); illudacetalic acid (); illudol (); illudalic acid and illudinine (); illudosone hemiacetal, isoomphadione and illudiolone (), and omphadiol (). The sesquiterpene alcohol (+) torreyol () (in square brackets) is not derived from Δ-6 protoilludene, instead it is proposed to be a derivative of α–muurolene.

Grayson T. Wawrzyn, et al. Chem Biol. ;19(6):772-783.
11.
Figure 7

Figure 7. From: Draft genome of Omphalotus olearius provides a predictive framework for sesquiterpenoid natural product biosynthesis in Basidiomycota.

Unrooted Neighbor-Joining phylogram of STS homologs identified in 42 Basidiomycota genomes. Five clades are highlighted with colors as in . STS from C. cinereus (Cop), O. olearius (Omp), F. pinicola (Fompi1), and the single STS described from Armillaria gallica (Armga1) () are labeled. Refer to the methods for tree construction parameters. Sequences used in the final alignment and the resultant phylogram data can be found in . See also for a breakdown of total number of putative STS and number of STS sequences used in tree building after manual inspection of alignment. See for product analysis of the STS from F. pinicola.

Grayson T. Wawrzyn, et al. Chem Biol. ;19(6):772-783.
12.
FIG 3

FIG 3. From: A Highly Conserved Basidiomycete Peptide Synthetase Produces a Trimeric Hydroxamate Siderophore.

Neighbor-joining tree of adenylation domains of selected fungal siderophore synthetases. Organism and enzyme names and accession numbers are indicated on leaves, as well as the number of A domains (i.e., A1 to A3 in the case of multiple A domains per enzyme). CsNPS2 belongs to the monophyletic type VI clade, a subclade of N5-acyl-N5-hydroxy-l-ornithine (acyl-HO)-activating A domains and consists exclusively of basidiomycete sequences. Bootstrap values above 50% are shown above the branches. The scale bar represents the number of amino acid substitutions per site. The branch to Omphalotus olearius Fso1 A3 is not drawn to scale. Accession numbers refer to entries in the NCBI, PDB, or the JGI databases (protein IDs) of the Joint Genome Institute.

Eileen Brandenburger, et al. Appl Environ Microbiol. 2017 Nov 1;83(21):e01478-17.
13.
Fig. 4

Fig. 4. From: Identification of sesquiterpene synthases from the Basidiomycota Coniophora puteana for the efficient and highly selective β-copaene and cubebol production in E. coli.

Unrooted neighbor-joining phylogram of all 29 reported and experimentally characterized STPSs from Basidiomycota. The protein sequence based analysis includes STPSs from Antrodia cinnamomea [], Armillaria gallica [], Boreostereum vibrans [], Coprinopsis cinereus [], Fomitopsis pinicola [], Lignosus rhinocerus [] Stereum hirsutum [], Omphalotus olearius [] as well as Coniophora puteana. The phylogenetic analysis revealed four distinct clades, divided into different cyclization mechanisms and product profiles. Copu1-3 belong to clade I including all other known β-copaene or cubebol synthases from Basidiomycota. For detailed information about the used sequences and accession numbers, see Additional file

Wolfgang Mischko, et al. Microb Cell Fact. 2018;17:164.
14.
Figure 4

Figure 4. From: Purification, crystallization and preliminary X-ray diffraction analysis of Omp6, a protoilludene synthase from Omphalotus olearius .

Crystals of Omp6. The scale bar represents 100 µm.

Maureen B. Quin, et al. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2013 May 1;69(Pt 5):574-577.
15.
Figure 5

Figure 5. From: Purification, crystallization and preliminary X-ray diffraction analysis of Omp6, a protoilludene synthase from Omphalotus olearius .

Diffraction pattern from a single Omp6 crystal. The crystal diffracted to a resolution of 2.9 Å.

Maureen B. Quin, et al. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2013 May 1;69(Pt 5):574-577.
16.
Figure 3

Figure 3. From: Purification, crystallization and preliminary X-ray diffraction analysis of Omp6, a protoilludene synthase from Omphalotus olearius .

Activity of purified Omp6. GC-MS analysis of an in vitro assay of Omp6 incubated with (E,E)-FPP. The enzyme produces Δ-6 protoilludene as its sesquiterpene product.

Maureen B. Quin, et al. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2013 May 1;69(Pt 5):574-577.
17.
Figure 1

Figure 1. From: Purification, crystallization and preliminary X-ray diffraction analysis of Omp6, a protoilludene synthase from Omphalotus olearius .

Proposed cyclization pathway leading to Δ-6 protoilludene. A 1,11 ring closure of the carbocation from (E,E)-FPP would yield a trans-humulyl cation intermediate. Hydride shifts and two cyclization steps would result in the hydrocarbon Δ-6 protoilludene. OPP represents the diphosphate moiety of the 15-carbon compound.

Maureen B. Quin, et al. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2013 May 1;69(Pt 5):574-577.
18.
Figure 2

Figure 2. From: A Sesquiterpene Synthase from the Endophytic Fungus Serendipita indica Catalyzes Formation of Viridiflorol.

Phylogenetic analysis of selected functionally characterized basidiomycete STSs, Cop1-6 [,] from Coprinopsis cinerea, Omp1-10 from Omphalotus olearius, Fompi|84944 from Fomitopsis pinicola [], Stehi1|159379, 128017, 25180, 64702, 73029 [,] from Stereum hirsutum, ArmGa1 [] from Armillaria gallica, AaVS [] from Cyclocybe aegerita (syn. Agrocybe aegerita), SiTPS from Serendipita indica and the SvTPS (NCBI accession number: PVF97777.1) from Serendipita vermifera were included in the analysis. A maximum-likelihood tree shows the 4 different STS clades formed, described also in [,] and . The enzymes falling in one clade are considered to catalyze the first cyclization of the substrate in the same specific way; STS Clade I catalyze 1,10 cyclization of E,E-FPP (pink); Clade II, 1,10 cyclization of (3R)-NPP (blue); Clade III, 1,11 cyclization of E,E-FPP (red); Clade IV, 1,6 or 1,7 cyclization of (3R)-NPP (yellow). SiTPS is found in Clade I. The scale bar indicates a genetic distance of 1 and the bootstrap values are shown below the branches.

Fani Ntana, et al. Biomolecules. 2021 Jun;11(6):898.
19.
Figure 2

Figure 2. From: Purification, crystallization and preliminary X-ray diffraction analysis of Omp6, a protoilludene synthase from Omphalotus olearius .

Purification of Omp6 by size-exclusion chromatography. The chromatogram shows two main peaks; SDS–PAGE (15%) analysis of the proteins contained within these fractions shows that the peak at the void volume (8.0 ml) contains unwanted proteins, while the 41 kDa Omp6 (highlighted with an arrow) elutes as a distinct peak (15.2 ml) from the Superdex 200 column.

Maureen B. Quin, et al. Acta Crystallogr Sect F Struct Biol Cryst Commun. 2013 May 1;69(Pt 5):574-577.
20.
Figure 5

Figure 5. From: Draft genome of Omphalotus olearius provides a predictive framework for sesquiterpenoid natural product biosynthesis in Basidiomycota.

Activities of purified Δ-6 protoilludene synthases Omp6 and Omp7. (a) Kinetic parameters for Omp6 and Omp7 were determined using (E,E)-FPP as the substrate in a coupled spectrophotometric assay. (b) GC-MS analysis of in vitro reactions containing purified Omp6 or Omp7 incubated with (E,E)-FPP. Both enzymes produce greater than 99 % Δ-6 protoilludene. Omp7 also produces a very small amount of pentalenene 1.

Grayson T. Wawrzyn, et al. Chem Biol. ;19(6):772-783.

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