New benzodioxepin type strobilurins from basidiomycetes. Structural revision and determination of the absolute configuration of strobilurin D and related β-methoxyacrylate antibiotics

Hellwig, Veronika; Dasenbrock, Johannes; Klostermeyer, Dörte; Kroiß, Stefan; Sindlinger, Tilman; Spiteller, Peter; Steffan, Bert; Steglich, Wölfgang; Engler-Lohr, Michaela; Semar, Sylvia; Anke, Timm

doi:10.1016/s0040-4020(99)00563-3

Cited by 28 publications

(38 citation statements)

References 29 publications

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“…Allyl phenyl ether (11) has been known to be converted to 2,3-dihydro-2-methylbenzofuran (2a) in moderate to good yields using heterogeneous catalyst, [12] In(III), [13] or Mo(CO) 6 [14]. We also tested the reaction of 11 using our catalysts and found that 11 was converted to 2a in moderate yield using Cu(OTf) 2 or silver catalysts.…”

Section: Claisen Rearrangement and Intramolecular Cyclization Of Allymentioning

confidence: 89%

“…AgOTf (3 mol% 3,4-Dihydro-2H-1,5-benzodioxepin structure is important framework in Strobilurin I and K that exhibit antifungul activities and cytostatic activities [11]. Therefore, our catalyst system was applied to the reaction of 2-(3-butenyloxy)phenol (7).…”

Section: Silver Catalystmentioning

confidence: 99%

“…3,4-Dihydro-2,6-dimethyl-2H-1,5-benzodioxepin (11) 1 H NMR (CDCl 3 ) d 1.46 (3H, d, J = 6.3, CH 3 ), 2.01-2.23 (2H, m, CH 2 CH 2 CH), 2.30 (3H, s, CH 3 ), 4.02-4.10 (1H, m, OCHHCH 2 ), m,CH), (1H, m, OCHHCH 2 ), 6.81-6.91 (3H, m, Ar). GC-MS (m/z) 178.…”

Section: 3-dihydro-2-methylbenzofuran (2a)mentioning

confidence: 99%

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Intramolecular cyclization of phenol derivatives with C C double bond in a side chain

Ito

Kato

Hamashima

et al. 2007

Journal of Organometallic Chemistry

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Section: Claisen Rearrangement and Intramolecular Cyclization Of Allymentioning

confidence: 89%

Section: Silver Catalystmentioning

confidence: 99%

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Intramolecular cyclization of phenol derivatives with C C double bond in a side chain

Ito

Kato

Hamashima

et al. 2007

Journal of Organometallic Chemistry

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“…Antifungal compounds such as the strobilurins, which have served as lead structures for the development of commercially available fungicides, [12] have been found in the mycelia of a variety of fungi including several Mycena species. Hydroxystrobilurin D (= hydroxystrobilurin G) from M. sanguinolenta is a benzodioxepine-type strobilurin [13] structurally related to the benzoxepines from M. galopus.…”

Section: Resultsmentioning

confidence: 99%

“…UV spectra were recorded with a Varian Cary 100 Bio UV/Vis spectrometer. NMR spectra were recorded with a Bruker DMX 250 spectrometer ( 1 H at 250.06, 13 C at 62.9 MHz), with a Bruker DMX 500 spectrometer equipped with a TXI probe ( 1 H at 500.11, 13 C at 125.8 MHz) and a Bruker DMX 600 spectrometer equipped with a TXI cryo probe ( 1 H at 600.13, 13 C at 150.9 MHz). Chemical shifts were determined relative to the solvent CDCl 3 (δ H = 7.26, δ C = 77.0 ppm) as internal standard.…”

Section: Methodsmentioning

confidence: 99%

Benzoxepine Esters as Precursors of the Wound‐Activated Chemical Defence of Mycena galopus

2008

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The native precursors E/Z‐1a to E/Z‐1e and 2a–2e of the antifungally active benzoxepines E/Z‐1 and 2 have been isolated from intact fruiting bodies of Mycena galopus. These precursors turned out to be fatty acid esters of the benzoxepines (pterulones) E/Z‐1 and 2. Metabolic profiling of ethyl acetate extracts from intact fruiting bodies, from the latex and from mechanically wounded fruiting bodies revealed that the known antifungally active benzoxepines E/Z‐1 and the previously unknown benzoxepines 2 are only present in injured fruiting bodies. Intact fruiting bodies and the latex, however, exclusively contain the corresponding ester derivatives E/Z‐1a to E/Z‐1e and 2a–2e. Unlike the antifungally active benzoxepines E/Z‐1 and 2, the esters E/Z‐1a to E/Z‐1e present in intact fruiting bodies turned out to be inactive. Upon injury the inactive esters E/Z‐1a to E/Z‐1e are cleaved by a putative esterase, and the bioactive benzoxepines E/Z‐1 and 2 are released, suggesting a wound‐activated defence mechanism of M. galopus against yeasts and parasitic fungi. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)

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Chemical Defence Strategies of Higher Fungi

Spiteller

2008

Chemistry A European J

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116

107

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Like plants, fungi have evolved a variety of defence strategies in order to protect themselves against feeding mammals, insects and infection with parasitic fungi. In contrast to plants little is known on the chemical ecology of fruiting bodies of higher fungi, particularly those defence mechanisms which are induced upon wounding have only occasionally been recognised. Methods both for the detection of permanently present defence compounds and for the elucidation of wound-activated chemical defence mechanisms are discussed in this concept paper.

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New benzodioxepin type strobilurins from basidiomycetes. Structural revision and determination of the absolute configuration of strobilurin D and related β-methoxyacrylate antibiotics

Cited by 28 publications

References 29 publications

Intramolecular cyclization of phenol derivatives with C C double bond in a side chain

Intramolecular cyclization of phenol derivatives with C C double bond in a side chain

Benzoxepine Esters as Precursors of the Wound‐Activated Chemical Defence of Mycena galopus

Chemical Defence Strategies of Higher Fungi

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