Production, isolation, and antimicrobial activity of hyalodendrin, a new antibiotic produced by a species of <i>Hyalodendron</i>

Stillwell, M. A.; Magasi, L. P.; Strunz, George M.

doi:10.1139/m74-116

Cited by 34 publications

(25 citation statements)

References 5 publications

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“…Five classes representing 14 genera are shown in Table 1: Dothideomycetes, Eurotiomycetes, Lecanoromycetes, Saccharomycetes and Sordariomycetes. At least two basidiomycetes, Stereum hirsutum and a Hyalodendron sp., produce ETPs: epicorazine and hyalodendrin, respectively (Kleinwachter et al, 2001;Stillwell et al, 1974). Lichens (presumably the fungal partner) produce the scabrosin ester ETPs (Ernst-Russell et al, 1999;Moerman et al, 2003).…”

Section: Sirodesminmentioning

confidence: 99%

The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis

2005

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Section: Sirodesminmentioning

confidence: 99%

The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis

2005

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“…A n AB quartet centered at 6 olites (1) is hyalodendrin (I),' produced by a 3.44 (2H, J = 14 Hz) represents the benzylic Hyalodendron sp. (2,3). We report here the protons, and demonstrates the tetrasubstituted isolation and identification of a new, related character of the neighboring carbon atom.…”

mentioning

confidence: 58%

“…Elution with benzene~hloroform (7 :3) afforded hyalodendrin (after crystallization, ca. 100 mg/l of culture medium) as described previously (2,3). Bisdethiodi(methy1thio)hyalodendrin (2) …”

Section: Isolatior~ Of Metabolitesmentioning

confidence: 99%

Metabolites of Hyalodendron sp.: Bisdethiodi(methylthio)hyalodendrin

Strunz¹,

Heissner²,

Kakushima³

et al. 1974

Can. J. Chem.

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Spectroscopic studies and chemical correlation with hyalodendrin show that a new metabolite of Hynlodetidrot~ sp. is bisdethiodi(methylthio)hyalodendrin (3-benzyl-6 hydroxymethyl-l,4-dimethyl-2,sdioxo-3,6-di(methy1 thi0)piperazine).Les t t i~d e s spectroscopiques et une correlation chinlique avec I'hyalodendrine dkmontrent q u ' i~n mttabolite nouveau d'une esptce d'Hynlorlet~rl,oti est la bisdethiodi(mtthylthio)hyalodendrine (3-benzyl-6-hydroxymtthyl-l,4-dim~thyl-2,5-dioxo-3,6-di(m~thylthio) piperazine).Can. J. Chem., 52,325 (1974) A recent addition to the group of biologically gens give rise to multiplets at 6 7.12 (2H) and active epidithiodiketopiperazine fungal metab-7.26 p.p.m. (3H). A n AB quartet centered at 6 olites (1) is hyalodendrin (I),' produced by a 3.44 (2H, J = 14 Hz) represents the benzylic Hyalodendron sp. (2, 3). We report here the protons, and demonstrates the tetrasubstituted isolation and identification of a new, related character of the neighboring carbon atom. metabolite, bisdethiodi(methylthio)hyalodendl.in Coupling with the hydroxyl proton ( J = 6 and (2), produced in culture by this organism.7 Hz), as well as geminal coupling ( J = 12 Hz) is observed for the two hydrogens attached to C y 3 0 the primary carbinol center, and they appear asdoublets The hydroxyl of doublets proton at 6 is 3.14 manifested and 3.85 p.p.m. as a broadened unsymmetrical "triplet" a t 6 1.43; as o 2~~expected, irradiation at 314 Hz collapsed the 1 signal for the carbinol protons to a n AB quartet ( J = 12 Hz). Singlets (3H each) a t 6 3.03 and and -CH20H functionality, as well as the two Comparison of the spectroscopic charac-meth~lthio groups was confirmed by the mass teristics of the new metabolite, C,6H22N203S2, spectral fragmentation Pattern (see Ex~erimen-with those of hyalodendrin (I), indicated that tal section). Ions a t n.l/e 132 and 72 can be the former compound is also an N-methylserine-rationalized in terms of the cleavages indicated N-methylphenylalanine diketopiperazine, bear-in Scheme 1 (c.f. ref. 8). ing substitution at the 3 and 6 positions.Correlation with hyalodendrin corroborated 2 displayed i.r. absorption indicative of amide the formulation 2. Thus, treatment of the former and hydroxyl functionality, as well as peaks with sodium borohydride in the presence of attributable to a monosubstituted phenyl group methyl iodide and ~~r i d i n e (5) at 0" gave a (see Experimental section) (2, 4). In the n.m.r. di(methylthi0) ether, identical in all respects spectrum (220 MHZ, CDCI,), the phenyl hydro-with the metabolite 2. Sodium borohydride For personal use only.

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“…The production and isolation of hyalodendrin and bisdethiodi(methy1thio) hyalodendrin have been detailed elsewhere (1)(2)(3). In a typical isolation sequence, material extracted with chloroform from 37 1 of filtered culture medium which had supported growth of Hyalodendron sp.…”

Section: Isolation Of 'Na/ural' Tetrasulfidementioning

confidence: 99%

“…(1)(2)(3). Metabolites 1 and 2, and the trisulfide 3, of undetermined absolute configuration, were obtained from cultures of an unidentified fungus (NRRL 3888) (4).…”

mentioning

confidence: 99%

An Epitetrathiodioxopiperazine with 3S,6S Configuration from Hyalodendron sp.

Strunz¹,

Kakushima²,

Stillwell³

1975

Can. J. Chem.

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Can. J. Chem. 53,295 (1975).(3S,6S)3-Benzyl-6-hydroxymethyl-1,4dimethyl-3,6-epitetrathiopiperazine-2,5-dione has been isolated from cultures of Hynlodendron sp. The same compound is produced when hyalodendrin is heated with methanol -hydrochloric acid. The fungitoxic epidithiodioxopiperazine hyalodendrin, 1, and the corresponding di(methy1-thio) ether, 2, both with 3S,6S configuration have recently been isolated from culture filtrates of Hyalodendron sp. (1-3). Metabolites 1 and 2, and the trisulfide 3, of undetermined absolute configuration, were obtained from cultures of an unidentified fungus (NRRL 3888) (4). The metabolite 1, with R configuration at positions 3 and 6, and compounds 2 and 4, evidently belonging to the same stereochemical series, are produced by Penicillium turbatum (5). Gliovictin, a metabolite of Helminthosporium victoriae also has structure 2 (6) and is likewise enantiomeric (3R,6R) with the corresponding Hyalodendron product.We record here some observations made during a study of the 3S,6S tetrasulfide 4, isolated from fermentations of Hyalodendron sp. This compound, Cl,H16N,0,S,, was present in chloroform extracts of the filtered culture medium in amounts which ranged up to 3% of the yield of pure hyalodendrin. It was slightly more polar than the latter, and could be separated and purified by preparative-layer chromatography, followed by crystallization. Comparison of the spectral characteristics of 4 (see Experimental section) with those of its co-metabolites 1 and 2 leave no doubt as to its constitution. Comparison of the circular dichroism curve of the Hyalodendron tetrasulfide (see Experimental section) with that published for the Penicillium metabolite (5) establishes that these compounds are enantiomeric at positions 3 and 6. A detailed discussion of the geometry of the tetrasulfide system of 4 is deferred at this stage, although it is noted that the synthetic compound N,N1 -dimethyl -3,6 -epitetrathiopiperazine -2,5-dione and sporidesmin G have been shown by X-ray analysis to be structurally similar with respect to the epitetrathiodioxopiperazine moiety (7,8).A tetrasulfide, identical in all respects (including c.d. spectrum) with the Hyalodendron tetrasulfide, was obtained in modest yield when hyalodendrin was refluxed in methanolic hydrochloric acid until no starting material remained (t.1.c.). By-products from this transformation, depleted in sulfur, resisted preliminary purificaCan. J. Chem. Downloaded from www.nrcresearchpress.com by 34.214.212.150 on 05/12/18For personal use only.

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Production, isolation, and antimicrobial activity of hyalodendrin, a new antibiotic produced by a species of Hyalodendron

Cited by 34 publications

References 5 publications

The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis

The epipolythiodioxopiperazine (ETP) class of fungal toxins: distribution, mode of action, functions and biosynthesis

Metabolites of Hyalodendron sp.: Bisdethiodi(methylthio)hyalodendrin

An Epitetrathiodioxopiperazine with 3S,6S Configuration from Hyalodendron sp.

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