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J Nat Prod. 2014 Jun 27;77(6):1459-66. doi: 10.1021/np5002253. Epub 2014 Jun 3.

Cytotoxic dimeric epipolythiodiketopiperazines from the ascomycetous fungus Preussia typharum.

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1
Natural Products Discovery Group, ‡Institute for Natural Products Applications and Research Technologies, and §Department of Chemistry and Biochemistry, Stephenson Life Sciences Research Center, 101 Stephenson Parkway, University of Oklahoma , Norman, Oklahoma 73019-5251, United States.

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.

PMID:
24893224
PMCID:
PMC4073660
DOI:
10.1021/np5002253
[Indexed for MEDLINE]
Free PMC Article
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