Journal
JOURNAL OF NATURAL PRODUCTS
Volume 77, Issue 4, Pages 800-806Publisher
AMER CHEMICAL SOC
DOI: 10.1021/np400880w
Keywords
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Funding
- National Natural Science Foundation of China [41376149, 41276146]
- 863 Foundation of China [2011AA09070201]
- Science & Technology Plan Project of Guangdong Province of China [2010B030600004, 2011A080403006]
- Guangzhou Project of Science & Technology Planning [2010J1-E331]
- China Postdoctoral Science Foundation [2013M542224]
- China's Marine Commonweal Research Project [201005022-2]
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A pair of unusual benzannulated 6,6-spiroketal enantiomers [(-)-1 and (+)-1] and three new biogenetically related compounds (2-4), together with two known related analogues (5 and 6), have been isolated from a mangrove fungus, Penicillium dipodomyicola HN4-3A. Their structures were elucidated on the basis of spectroscopic analysis (1D and 2D NMR data) and X-ray crystallography. The absolute configurations of enantiomers (-)-1 and (+)-1 were determined using quantum chemical calculations of the electronic circular dichroic (ECD) spectra. Compounds 2 and 3 exhibited strong inhibitory activity against Mycobacterium tuberculosis protein tyrosine phosphatase B (MptpB) with IC50 values of 0.16 +/- 0.02 and 1.37 +/- 0.05 mu M, respectively.
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