Mutterkorn‐Farbstoffe, XVII. Biosynthese der Ergochrome

Franck, Burchard; Hüper, Fritz; Gröger, D.; Erge, D.

doi:10.1002/cber.19681010610

Cited by 26 publications

(5 citation statements)

References 18 publications

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“…Different relative peak heights for the two compounds in the mass spectrum for the molecular ion and a peak corresponding to [M–CO 2 Me] + reveal that ergochrysin A loses this fragment more readily than ergochrysin B. Another paper from Franck et al in 1968 investigated the biosynthesis of the ergochrome class of compounds with 1- 14 C, 2- 14 C, and 1- 3 H sodium acetate feeding of several Claviceps species . The results indicated that the species are acetate-derived and that an anthraquinone intermediate is involved in the biosynthetic pathway, which proceeds to the ergochromes with oxidative ring-opening and subsequent oxa-Michael addition (see Schemes and ).…”

Section: Dimers and Heterodimersmentioning

confidence: 99%

“…The results indicated that the species are acetate-derived and that an anthraquinone intermediate is involved in the biosynthetic pathway, which proceeds to the ergochromes with oxidative ring-opening and subsequent oxa-Michael addition (see Schemes and ). The authors exposed radioactive shikimic acid to the Claviceps cultures, but this material was not fed into the ergochrome species isolated at the ending, which is due to the contrasting xanthone biosynthesis pathways in fungi to those found in plants (which use shikimic acid as a biosynthetic precursor) …”

Section: Dimers and Heterodimersmentioning

confidence: 99%

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Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis

2012

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The majority of xanthones reported from fungi, bacteria, and lichens, and particularly those reported relatively early on, have a monomeric and fully aromatized structure. These include arthothelin, asemone, asperxanthone, austocystins, bikaverin, chaetoxanthones, chodatin, conioxanthone A, erythrommone, emericellin, globosuxanthones C and D, griseoxanthone C, lichexanthones and norlichexanthones, Microsphaeropsis xanthones, mycoxanthone, Phoma and Phomopsis xanthones, pinselin and pinselic acid, sterigmatocystins, tajixanthone, thiomelin, thiophanic acid, thiophaninic acid, thuringione, umbilicaxanthones, vinetorin, varixanthone, vertixanthone, and Wardomyces and Xylaria xanthones.Arthothelin. Santesson reported observing this compound in the mass-spectral analysis of the lichen Leconora reuteri. 65 Arthothelin (2,4,5-trichloronorlichexanthone, 19, Figure 2) has

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Section: Dimers and Heterodimersmentioning

confidence: 99%

Section: Dimers and Heterodimersmentioning

confidence: 99%

Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis

2012

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“…Krolikiewicz Research Laboratories of Schering AG, Berlin/Bergkamen 1 Berlin 65, Postfach 6503 1 I (Germany) material after 5min at 24°C. The 'H-NMR spectra of the precipitated perchlorates in [D,]pyridine confirmed quantitative removal of the BOC group leaving the Z group in (3) and the benzyl and tert-butyl esters in ( 4 ) intact (Table 1).…”

Section: By Helmut Vorbriiggen and Konrad Krolikiewicz"]mentioning

confidence: 84%

Secoanthraquinones from Emodin

Franck¹,

Berger‐Lohr²

1975

Angew. Chem. Int. Ed. Engl.

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conclusions to bedrawn about the topology of the environment of reactive thiol groups. The scope of the above addition can be widened considerably since lipophilic, hydrophilic, colored, or polymer-bound P-nitrostyrenes are readily accessible via suitably substituted aldehydes and could also find application in the isolation and chromatography of cysteine peptides. N-tert-Butoxycarbonyl-S-(2-nitro-l-phenylethyl)-L-cysteinr N-Methylmorpholine (10ml) is added to a stirred solution of N-tert-butoxycarbonyl-L-cysteineL'] (0.1 mol) and 0-nitrostyrene (0.1 mol) in anhydrous, N,-saturated ethanol (100ml). The colorless N-methylmorpholinium salt of the adduct precipitates within 2min. After 10min the mixture is cooled to O'C, filtered, and the precipitate washed with ether (yield 70%; m.p. 131-133°C). The S-and N-protected acid can be liberated by ethyl acetate extraction of an acidified aqueous solution of the salt and recrystallized from ethyl acetatepight petroleum; m.p. 74-77°C; R,=0.85 (CHC13/CH30H,I CH, COOH/H, 0 60 : 45 : 6 : 24).

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“…Several natural products were isolated from the bark of Cratoxylum cochinchinense in 1995 by Sim et al 102 Aer extensive HPLC purication of the isolated compounds, detailed high eld NMR spectroscopy was used to identify a novel dimeric xanthone, named cratoxyxanthone (48).…”

Section: Cratoxyxanthonementioning

confidence: 99%

“…a secalonic acid seems unlikely. Despite efforts in the detailed study of the biosynthesis of dimeric xanthones, particularly of the secalonic acids by Frank and co-workers, 23,40,[48][49][50] the dimerisation of xanthones remains a tricky subject for both the synthetic and biosynthetic chemistthe extent of the involvement of enzymes, and their nature, is at present unclear. There has been, at the time of writing, no direct observation of enzymatic dimerisation of the monomer units.…”

Section: Xanthone Dimerisationmentioning

confidence: 99%

Xanthone dimers: a compound family which is both common and privileged

2015

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Covering: up to 2014. Xanthone dimers are a widespread, structurally-diverse family of natural products frequently found in plants, fungi and lichens. They feature an intriguing variety of linkages between the component xanthones (benzannulated chromanones). These synthetically elusive secondary metabolites are of great interest due to their broad array of bioactivities, which has led to the xanthones being designated as 'privileged structures'. We seek herein to give an overview of all reliably-described xanthone dimers, their structures, occurrence, and the bioactivities established to date. The possible biosynthetic pathways leading to members of this family are also discussed in light of our current knowledge.

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Mutterkorn‐Farbstoffe, XVII. Biosynthese der Ergochrome

Cited by 26 publications

References 18 publications

Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis

Xanthones from Fungi, Lichens, and Bacteria: The Natural Products and Their Synthesis

Secoanthraquinones from Emodin

Xanthone dimers: a compound family which is both common and privileged

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