Abstract
Four unusual indole-terpenoids, penerpenes A-D (1-4), along with two known ones paxilline (5) and emindole SB (6), were isolated from the marine-derived fungus Penicillium sp. KFD28. The absolute structures of 1-4 were elucidated on the basis of spectroscopic data and ECD spectra analysis along with quantum ECD calculations. Compounds 1 and 2 showed potent inhibitory activity toward protein tyrosine phosphatases (PTP1B and TCPTP). Plausible biosynthetic pathways of compounds 1-4 are proposed.
Publication types
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Research Support, Non-U.S. Gov't
MeSH terms
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Enzyme Inhibitors / chemistry
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Enzyme Inhibitors / isolation & purification
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Enzyme Inhibitors / pharmacology*
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Humans
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Indoles / chemistry
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Indoles / isolation & purification
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Indoles / pharmacology*
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Models, Molecular
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Molecular Conformation
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Penicillium / chemistry*
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Protein Tyrosine Phosphatase, Non-Receptor Type 1 / antagonists & inhibitors*
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Protein Tyrosine Phosphatase, Non-Receptor Type 1 / metabolism
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Protein Tyrosine Phosphatase, Non-Receptor Type 2 / antagonists & inhibitors*
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Protein Tyrosine Phosphatase, Non-Receptor Type 2 / metabolism
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Quantum Theory
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Terpenes / chemistry
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Terpenes / isolation & purification
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Terpenes / pharmacology*
Substances
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Enzyme Inhibitors
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Indoles
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Terpenes
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indole
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PTPN1 protein, human
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PTPN2 protein, human
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Protein Tyrosine Phosphatase, Non-Receptor Type 1
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Protein Tyrosine Phosphatase, Non-Receptor Type 2