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Cytotoxic dimeric epipolythiodiketopiperazines from the ascomycetous fungus Preussia typharum.

ABSTRACT: Two new dimeric epipolythiodiketopiperazines, preussiadins A (1) and B (2), together with two known diastereomers, leptosins C (6) and A (7), were obtained from the mycelia of a Preussia typharum isolate. The structures of the new compounds were established by spectroscopic methods, and the absolute configurations of 1 and 2 were assigned by chemical transformations and comparisons of quantum chemical ECD and VCD calculations to experimental data. Compound 1 exhibited potent cytotoxic activity in the NCI-60 cell line panel with an average LC50 value of 251 nM. Further studies demonstrated that 1 circumvents P-glycoprotein-mediated drug resistance, yet had no significant antitumor activity in a xenograft UACC-62 melanoma model.

SUBMITTER: Du L

PROVIDER: S-EPMC4073660 | biostudies-literature | 2014 Jun

REPOSITORIES: biostudies-literature

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Cytotoxic dimeric epipolythiodiketopiperazines from the ascomycetous fungus Preussia typharum.

Du Lin L Robles Andrew J AJ King Jarrod B JB Mooberry Susan L SL Cichewicz Robert H RH

Journal of natural products 20140603 6

Two new dimeric epipolythiodiketopiperazines, preussiadins A (1) and B (2), together with two known diastereomers, leptosins C (6) and A (7), were obtained from the mycelia of a Preussia typharum isolate. The structures of the new compounds were established by spectroscopic methods, and the absolute configurations of 1 and 2 were assigned by chemical transformations and comparisons of quantum chemical ECD and VCD calculations to experimental data. Compound 1 exhibited potent cytotoxic activity i ...[more]

PMID: 24893224

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