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Shornephine A: Structure, Chemical Stability, and P‑Glycoprotein Inhibitory Properties of a Rare Diketomorpholine from an Australian Marine-Derived Aspergillus sp.

Overview of attention for article published in Journal of Organic Chemistry, September 2014
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Title
Shornephine A: Structure, Chemical Stability, and P‑Glycoprotein Inhibitory Properties of a Rare Diketomorpholine from an Australian Marine-Derived Aspergillus sp.
Published in
Journal of Organic Chemistry, September 2014
DOI 10.1021/jo501501z
Pubmed ID
Authors

Zeinab G. Khalil, Xiao-cong Huang, Ritesh Raju, Andrew M. Piggott, Robert J. Capon

Abstract

Chemical analysis of an Australian marine sediment-derived Aspergillus sp. (CMB-M081F) yielded the new diketomorpholine (DKM) shornephine A (1) together with two known and one new diketopiperazine (DKP), 15b-β-hydroxy-5-N-acetyladreemin (2), 5-N-acetyladreemin (3), and 15b-β-methoxy-5-N-acetyladreemin (4), respectively. Structure elucidation of 1-4 was achieved by detailed spectroscopic analysis, supported by chemical degradation and derivatization, and biosynthetic considerations. The DKM (1) underwent a facile (auto) acid-mediated methanolysis to yield seco-shornephine A methyl ester (1a). Our mechanistic explanation of this transformation prompted us to demonstrate that the acid-labile and solvolytically unstable DKM scaffold can be stabilized by N-alkylation. Furthermore, we demonstrate that at 20 μM shornephine A (1) is a noncytotoxic inhibitor of P-glycoprotein-mediated drug efflux in multidrug-resistant human colon cancer cells.

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Mendeley readers

Mendeley readers

The data shown below were compiled from readership statistics for 34 Mendeley readers of this research output. Click here to see the associated Mendeley record.

Geographical breakdown

Country Count As %
Unknown 34 100%

Demographic breakdown

Readers by professional status Count As %
Researcher 7 21%
Student > Ph. D. Student 6 18%
Student > Doctoral Student 4 12%
Student > Master 4 12%
Student > Bachelor 2 6%
Other 3 9%
Unknown 8 24%
Readers by discipline Count As %
Chemistry 14 41%
Biochemistry, Genetics and Molecular Biology 4 12%
Medicine and Dentistry 2 6%
Agricultural and Biological Sciences 2 6%
Pharmacology, Toxicology and Pharmaceutical Science 1 3%
Other 2 6%
Unknown 9 26%
Attention Score in Context

Attention Score in Context

This research output has an Altmetric Attention Score of 1. This is our high-level measure of the quality and quantity of online attention that it has received. This Attention Score, as well as the ranking and number of research outputs shown below, was calculated when the research output was last mentioned on 03 September 2014.
All research outputs
#22,778,604
of 25,394,764 outputs
Outputs from Journal of Organic Chemistry
#27,854
of 28,631 outputs
Outputs of similar age
#213,086
of 248,700 outputs
Outputs of similar age from Journal of Organic Chemistry
#125
of 134 outputs
Altmetric has tracked 25,394,764 research outputs across all sources so far. This one is in the 1st percentile – i.e., 1% of other outputs scored the same or lower than it.
So far Altmetric has tracked 28,631 research outputs from this source. They receive a mean Attention Score of 4.5. This one is in the 1st percentile – i.e., 1% of its peers scored the same or lower than it.
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We're also able to compare this research output to 134 others from the same source and published within six weeks on either side of this one. This one is in the 1st percentile – i.e., 1% of its contemporaries scored the same or lower than it.