Linked Life Data

19082162

Source:http://linkedlifedata.com/resource/pubmed/id/19082162

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pubmed-article:19082162pubmed:abstractTextGilvocarcin-type polyketide glycosides represent some of the most powerful antitumor therapeutics. Bioactivity-guided fractionation of a culture extract of Streptomyces polyformus sp. nov. (YIM 33176) yielded the known gilvocarcin V (2) and a novel related compound, polycarcin V (1). Structure elucidation by NMR and chemical derivatization revealed that the congener (1) features a C-glycosidically linked alpha-L-rhamnopyranosyl moiety in lieu of the D-fucofuranose. The concomitant production of two distinct furanosyl and pyranosyl C-glycosides that share the same aglycone is unprecedented in bacteria. A conversion of both isoforms via a quinone methide intermediate can be ruled out, thus pointing to two individual C-glycosylation pathways. Cytotoxicity profiling of polycarcin V in a panel of 37 tumor cell lines indicated significant antitumoral activity with a pronounced selectivity for non-small-cell lung cancer, breast cancer and melanoma cells. As the antiproliferative fingerprint is identical to that of actinomycin D, the known DNA interaction of gilvocarcins was established as a general principle of antitumorigenic activity.lld:pubmed
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pubmed-article:19082162pubmed:articleTitlePlasticity in gilvocarcin-type C-glycoside pathways: discovery and antitumoral evaluation of polycarcin V from Streptomyces polyformus.lld:pubmed
pubmed-article:19082162pubmed:affiliationLeibniz Institute for Natural Product Research and Infection Biology, Hans-Knöll-Institute, Beutenbergstr. 11a, D-07745, Jena, Germany.lld:pubmed
pubmed-article:19082162pubmed:publicationTypeJournal Articlelld:pubmed
pubmed-article:19082162pubmed:publicationTypeResearch Support, Non-U.S. Gov'tlld:pubmed
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