title: Peniphenones A-D from the mangrove fungus Penicillium dipodomyicola HN4-3A as inhibitors of Mycobacterium tuberculosis phosphatase MptpB.
abstract: 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 μM, respectively.
authors.affiliation: School of Chemistry and Chemical Engineering, Sun Yat-sen University , Guangzhou 510275, People's Republic of China.
authors.forename: Hanxiang
authors.initials: H
authors.lastname: Li
authors.forename: Jieyi
authors.initials: J
authors.lastname: Jiang
authors.forename: Zhaoming
authors.initials: Z
authors.lastname: Liu
authors.forename: Shaoe
authors.initials: S
authors.lastname: Lin
authors.forename: Guoping
authors.initials: G
authors.lastname: Xia
authors.forename: Xuekui
authors.initials: X
authors.lastname: Xia
authors.forename: Bo
authors.initials: B
authors.lastname: Ding
authors.forename: Lei
authors.initials: L
authors.lastname: He
authors.forename: Yongjun
authors.initials: Y
authors.lastname: Lu
authors.forename: Zhigang
authors.initials: Z
authors.lastname: She
mesh_terms: D002681:China; D018360:Crystallography, X-Ray; D020128:Inhibitory Concentration 50; D008968:Molecular Conformation; D015394:Molecular Structure; D009169:Mycobacterium tuberculosis / Q000187:drug effects* / Q000201:enzymology; D019906:Nuclear Magnetic Resonance, Biomolecular; D010407:Penicillium / Q000737:chemistry*; D017027:Protein Tyrosine Phosphatases / Q000037:antagonists & inhibitors*; D043982:Rhizophoraceae / Q000382:microbiology*; D013141:Spiro Compounds / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism
chemical_list: D013141:Spiro Compounds; C000589637:peniphenone A; D017027:Protein Tyrosine Phosphatases