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1. (Article ID: 8341)
Vicente F, Basilio A, Platas G, Collado J, Bills GF, González del Val A, Martin J, Tormo JR, Harris GH, Zink DL, Justice M, Kahn JN, Peláez F
Distribution of the antifungal agents sordarins across filamentous fungi
Mycological Research 113(6-7) (2009)
754-770
Sordarins are a class of natural antifungal agents which act by specifically inhibiting fungal protein synthesis through their interaction with the elongation factor 2, EF2. A number of natural sordarins produced by diverse fungi of different classes have been reported in the literature. We have run an exhaustive search of sordarin-producing fungi using two different approaches consecutively, the first one being a differential sensitivity screen using a sordarin-resistant mutant yeast strain run in parallel with a wild type strain, and the second one an empiric screen against Candida albicans followed by early detection of sordarins by LC-MS analysis. Using these two strategies we have detected as many as 22 new strains producing a number of different sordarin analogues, either known (sordarin, xylarin, zofimarin) or novel (isozofimarin and 4'-O-demethyl sordarin). Sordarin and xylarin were the most frequently found compounds in the class. The producing strains were subjected to sequencing of the ITS region to determine their phylogenetic affinities. All the strains were shown to belong to the Xylariales, being distributed across three families in this order, the Xylariaceae, the Amphisphaeriaceae, and the Diatrypaceae. Despite being screened in large numbers, we did not find sordarin production in any other fungal group, including those orders where sordarin producing fungi are known to exist (i.e., Sordariales, Eurotiales, and Microascales), suggesting that the production of sordarin is a trait more frequently associated to members of the Xylariales than to any other fungal order
natural products, antifungal agents, sordarin, xylarin, Xylariales, zofimarin
NCBI PubMed ID: 19249360Publication DOI: 10.1016/j.mycres.2009.02.011Journal NLM ID: 8913481Publisher: Cambridge University Press
Correspondence: fpelaez

cnio.es
Institutions: Natural Products Chemistry, Merck Research Laboratories, Rahway, USA, Centro de Investigación Básica, Merck Sharp and Dohme de España, Madrid, Spain, Infectious Diseases, Merck Research Laboratories, Rahway, USA
Methods: DNA sequencing, DNA techniques, ESI-MS, HPLC, extraction, LC-MS, cell growth, antifungal activity test, HPLC-DAD
The publication contains the following compound(s):
- Compound ID: 20859
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Subst1-(1-3)-b-D-6dAltp4Me-(1-17)-Subst
Subst = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4;
Subst1 = (Z)-2-methyl-3-((2'S,3S,3'S)-3'-methyl-[2,2'-bioxiran]-3-yl)acrylic acid = SMILES C/C(=C/[C@@H]1OC1[C@H]2O[C@H]2C){1}C(=O)O |
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Structure type: monomer
Trivial name: hypoxysordarin, hypoxysordarin, FR231956
Compound class: glycoside
- Compound ID: 20247
|
b-D-6dAltp4Me-(1-17)-Subst
Subst = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4 |
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Structure type: monomer
C27H40O8
Trivial name: sordarin
Compound class: glycoside
Reference(s) to other database(s): GenDB:AJ302438
- Compound ID: 19655
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b-D-Altp4Me-(1-17)-Subst
Subst = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4 |
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Structure type: monomer
Trivial name: hydroxysordarin
Compound class: glycoside, diterpene glycoside
- Compound ID: 20869
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Subst1-(1-3)-b-D-6dAltp4Me-(1-17)-Subst
Subst = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4;
Subst1 = (2Z,5E)-7-hydroxy-2-methyl-4-oxoocta-2,5-dienoic acid = SMILES C/C(=C/C(=O)/C=C/C(C)O){1}C(=O)O |
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Structure type: monomer
Trivial name: neosordarin
Compound class: glycoside
- Compound ID: 20870
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b-D-Rhap4Me-(1-17)-Subst
Subst = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4 |
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Structure type: monomer
Trivial name: sordarin B
Compound class: glycoside
- Compound ID: 20874
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Subst1-(1-3)-b-D-6dAltp4Me-(1-17)-Subst
Subst = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4;
Subst1 = hexa-2Z,4E-dienoic acid = SMILES C/C=C/C=C\{1}C(=O)O |
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Structure type: monomer
Trivial name: zofimarin
Compound class: glycoside
Reference(s) to other database(s): GenDB:FJ175179
- Compound ID: 20875
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Subst1-(1-3)-b-D-6dAltp4Me-(1-17)-Subst
Subst = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4;
Subst1 = hexa-2E,4Z-dienoic acid = SMILES C/C=C\C=C\{1}C(=O)O |
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Structure type: monomer
Trivial name: isozofimarin
Compound class: glycoside
Reference(s) to other database(s): GenDB:FJ175177
- Compound ID: 20871
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Subst1-(1-3)-b-D-6dAltp4Me-(1-17)-Subst
Subst = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4;
Subst1 = 2-methylhexa-2E,4E-dienoic acid = SMILES C/C=C/C=C(C)/{1}C(=O)O |
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Structure type: monomer
Trivial name: GR135402-3
Compound class: glycoside
- Compound ID: 20872
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b-D-6dAltp3Ac4Me-(1-17)-Subst
Subst = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4 |
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Structure type: monomer
Trivial name: GR135402-6
Compound class: glycoside
- Compound ID: 20873
|
Subst1-(1-3)-b-D-6dAltp4Me-(1-17)-Subst
Subst = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4;
Subst1 = 2-methylhexa-2Z,4E-dienoic acid = SMILES C/C=C/C=C(/C)\{1}C(=O)O |
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Structure type: monomer
Trivial name: GR135402-7, GR135402
Compound class: glycoside
- Compound ID: 20876
|
Subst-(1-3:2-3)-b-D-Sugp4Me-(1-17)-Subst1
Subst = 2S-hydroxysebacic acid, 2S-hydroxydecanedioic acid = SMILES O=C(O)CCCCCCC{2}[C@H](O){1}C(=O)O;
Sug = 6-deoxy-3-hydroxy-arabino-hexose = SMILES C[C@H]1O{1}[C@@H](O)[C@@H](O){3}C(O)(O){4}[C@@H]1O;
Subst1 = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4 |
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Structure type: monomer
Trivial name: moriniafungin
Compound class: glycoside
- Compound ID: 20877
|
b-D-6dAltp-(1-17)-Subst
Subst = sordaricin = SMILES C[C@@H]1CC[C@@H]2[C@@H]1C[C@]3({17}CO)[C@@H]4C[C@@]2(C=O)[C@@]3({13}C(O)=O)C(C(C)C)=C4 |
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Structure type: monomer
Trivial name: 4'-O-demethylsordarin
Compound class: glycoside
Reference(s) to other database(s): GenDB:FJ175156
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