Chemical modifications of zearalenone. I

Jensen, N. P.; Brown, R. D.; Schmitt, S. M.; Windholz, T. B.; Patchett, A. A.

doi:10.1021/jo00975a040

Cited by 14 publications

(10 citation statements)

References 2 publications

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“…To confirm the putative structure of P16 as ZEN-11,12-oxide, ZEN was subjected to chemical epoxidation using m -chloroperbenzoic acid (mCPBA). As noted previously by Jensen et al , the olefinic double bond of ZEN is quite resistant to epoxidation. However, the profile obtained by LC-DAD-MS analysis of the reaction mixture after 5 h showed that, in addition to ∼55% unreacted ZEN, two peaks had formed that had [M − H] − ions at m / z 333, indicative of monooxygenated ZENs.…”

Section: Resultssupporting

confidence: 63%

Identification of an Aliphatic Epoxide and the Corresponding Dihydrodiol as Novel Congeners of Zearalenone in Cultures of Fusarium graminearum

Pfeiffer

Hildebrand

Becker

et al. 2010

J. Agric. Food Chem.

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The mycotoxin zearalenone (ZEN) is produced by various Fusarium fungi and frequently found as a contaminant in food and feed. There are reports in the literature that several closely related analogues of ZEN are also formed in cultures of Fusarium species. We have therefore analyzed the organic extract from a 40 day culture of Fusarium graminearum by LC-DAD-MS and detected 15 compounds, which could be congeners of ZEN because of their ultraviolet, mass spectroscopy, and tandem mass spectroscopy spectra. In addition to confirming the previously reported α- and β-stereoisomers of 5-hydroxy-ZEN and 10-hydroxy-ZEN, we identified seven ZEN congeners for the first time. One of the major novel congeners was shown by nuclear magnetic resonance spectroscopy and chemical synthesis to have the structure of an aliphatic ZEN epoxide, whereas two minor products proved to be the corresponding dihydrodiols. In addition, three stereoisomers of a cyclization product of the dihydrodiols, carrying a spiro-acetal group, were identified as fungal products for the first time. The latter may be artifacts, because the ZEN epoxide and dihydrodiol are unstable under acidic conditions and rearrange easily to the spiro-acetal compounds.

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Section: Resultssupporting

confidence: 63%

Identification of an Aliphatic Epoxide and the Corresponding Dihydrodiol as Novel Congeners of Zearalenone in Cultures of Fusarium graminearum

Pfeiffer

Hildebrand

Becker

et al. 2010

J. Agric. Food Chem.

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“…These compounds act on the human estrogen receptor in competition with 17-estradiol . In our own studies, zearalenone ( 15 ), both stereoisomers of zearalenol ( 16 , 17 ), and semisynthetic derivatives from hydrogenation, methylation, and acetylation were studied in comparison with the metabolites of P 0297. − Zearalenone ( 15 ) and α-zearalenol ( 16 ) and their derivatives did not exhibit any activity against HSV1, while β-zearalenol ( 17 ) was the most potent among all compounds examined in this study (Table ). Hydrogenation of β-zearalenol ( 17 ) to β-zearalanol ( 21 ) resulted in decreased activities, while the methylation and acetylation products of 17 were inactive.…”

Section: Resultsmentioning

confidence: 99%

“…Pochonin C (6): brownish oil; HPLC, tR 6.6 min (system 1); 1 H NMR ([D6]DMSO, 500 MHz), see Table 2; 13 + , 349 (43), 347 (100) (system 5); EIMS m/z 402 (7), 400 (11) [M + H] + , 366 (6), 364 (6), 314 (3), 312 (7), 229 (12), 203 89), 201 (26), 186 (33), 184 (100), 157 (16), 155 (16), 121 (25), 96 (32); HREIMS m/z 400.0472 (calcd for C 18H18Cl2O6, 400.0480).…”

Section: Methodsmentioning

confidence: 99%

Pochonins A−F, New Antiviral and Antiparasitic Resorcylic Acid Lactones from Pochonia chlamydosporia var. catenulata

et al. 2003

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Monorden (1) and the novel resorcylic acid lactones pochonins A (2), B (4), C (6), D (7), and E (8) as well as tetrahydromonorden (5) and pseurotin A (22) were isolated from cultures of the clavicipitaceous hyphomycete Pochonia chlamydosporia var. catenulata strain P 0297. Fermentation of P 0297 in bromide-containing culture media led to a shift in secondary metabolite production and yielded monocillins III (3) and II (9) as major metabolites besides monorden (1) as well as the novel compounds pochonin F (10) and a monocillin II glycoside (11) as minor metabolites. Most of these compounds showed moderate activities in a cellular replication assay against Herpes Simplex Virus 1 (HSV1) and against the parasitic protozoan Eimeria tenella. In contrast to the structurally related zearalenone derivatives none of the metabolites of strain P 0297 were found to be active in a fluorescence polarization assay for determination of modulatory activities on the human estrogenic receptor ERbeta. Beta-zearalenol (17), but not zearalenone (15) and alpha-zearalenol (16), showed antiherpetic effects. We report the production, isolation, and structure elucidation of compounds 1-11 and their biological characterization.

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“…Returning to the chemical objectives of the New Lead Discovery Department, it had become evident by the mid 1970s that the random synthesis of compounds for screening was not a cost-effective way of making new discoveries. In its place, we decided to organize an enzyme inhibitor design project and enlisted two expert consult- (12) interest in our laboratories. It reduces histamine levels most rapidly in tissues in which there is a high turnover of histamine and it is active, especially when chronically administered, in various animal models of allergic inflammation, ulcers, and asthma.…”

Section: E B Hershberg Award Addressmentioning

confidence: 99%

Excursions in drug discovery

Patchett¹

1993

J. Med. Chem.

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Chemical modifications of zearalenone. I

Abstract: Chemical transformations of the aliphatic portion of the mold metabolite zearalenone were examined. Reactions at the C'-6 ketone and the C'-l double bond and positions adjacent to these reaction centers are reported.The reactions proved to be quite regioselective.

Cited by 14 publications

References 2 publications

Identification of an Aliphatic Epoxide and the Corresponding Dihydrodiol as Novel Congeners of Zearalenone in Cultures of Fusarium graminearum

Identification of an Aliphatic Epoxide and the Corresponding Dihydrodiol as Novel Congeners of Zearalenone in Cultures of Fusarium graminearum

Pochonins A−F, New Antiviral and Antiparasitic Resorcylic Acid Lactones from Pochonia chlamydosporia var. catenulata

Excursions in drug discovery

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