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dc.contributor.authorSurup, Frank
dc.contributor.authorMinh Thi Tran, Thu
dc.contributor.authorPfütze, Sebastian
dc.contributor.authorBudde, Jarmo
dc.contributor.authorMoussa-Ayoub, Tamer E
dc.contributor.authorRohn, Sascha
dc.contributor.authorJerz, Gerold
dc.date.accessioned2020-12-16T09:18:02Z
dc.date.available2020-12-16T09:18:02Z
dc.date.issued2020-07-13
dc.identifier.citationFood Chem. 2021 Jan 1;334:127552. doi: 10.1016/j.foodchem.2020.127552. Epub 2020 Jul 13.en_US
dc.identifier.pmid32795786
dc.identifier.doi10.1016/j.foodchem.2020.127552
dc.identifier.urihttp://hdl.handle.net/10033/622657
dc.description.abstractExtracts of Opuntia stricta var. dillenii fruits were fractionated by semi-preparative high-performance countercurrent chromatography (HPCCC) to study the secondary metabolite formation, whereby HPCCC showed a superior separation capacity to fractionate minor metabolites compared to HPLC. A family of new peptides was detected in semi-polar fractions when monitoring the HPCCC separation by off-line injections of fractions to ESI-MS/MS. Planar structures of the major compounds, two 14-ring-membered cyclopeptide alkaloids, which were named opuntisines A and B, were elucidated by 1D- and 2D-NMR spectroscopy and HR-ESI-MS/MS spectrometry, while a combination of chemical derivatisation and degradation revealed the stereo-configurations. Specifically, the methods of Marfey and Mosher indicated l-Glu, l-Ile, l-Phe and 1S-configurations, respectively; ROESY correlations revealed 8S, 9S. The novel opuntisine A showed moderate activity against the Gram-negative bacterium Escherichia coli, but no further antibacterial, antifungal nor cytotoxic effects. This bioactive natural product class is reported for the first time in the plant family Cactaceae.en_US
dc.language.isoenen_US
dc.publisherElsevieren_US
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 International*
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subject1D/2D-NMRen_US
dc.subjectCactaceaeen_US
dc.subjectCyclopeptide alkaloidsen_US
dc.subjectHigh-performance countercurrent chromatographyen_US
dc.subjectOpuntia stricta var. dilleniien_US
dc.subjectSecondary metabolitesen_US
dc.subjectStructure elucidationen_US
dc.titleOpuntisines, 14-membered cyclopeptide alkaloids from fruits of Opuntia stricta var. dillenii isolated by high-performance countercurrent chromatography.en_US
dc.typeArticleen_US
dc.identifier.eissn1873-7072
dc.contributor.departmentHZI,Helmholtz-Zentrum für Infektionsforschung GmbH, Inhoffenstr. 7,38124 Braunschweig, Germany.en_US
dc.identifier.journalFood chemistryen_US
dc.source.volume334
dc.source.beginpage127552
dc.source.endpage
dc.source.journaltitleFood chemistry
dc.source.countryEngland


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