Journal of Natural Products · 2019 · 57 citations · 16 references
Natural SciencesBiochemistryChemistryBioorganic ChemistryOrganic ChemistryStructure-activity RelationshipsFungal Secondary MetabolitesHeterocyclic ChemistryHeterocyclic CompoundsMarine Bioactive CompoundsMarine Natural ProductsTerpenoid BiosynthesisBioactive Compounds From Marine FungiBioactive Compounds From Marine MollusksBivalve BioactivesFungal Bioactive CompoundsMarine Fungal MetabolitesMarine Fungal Natural ProductsMarine Fungal Secondary MetabolitesProtein Tyrosine Phosphatase Inhibitors
Five new indole-terpenoids named penerpenes E–I (1–5), along with seven known ones (6–12), were isolated from the marine-derived fungus Penicillium sp. KFD28 from a bivalve mollusk, Meretrix lusoria. The structures of the new compounds were elucidated from spectroscopic data and ECD spectroscopic analyses. Compound 1 was assigned as an indole-diterpenoid with a unique 6/5/5/6/6/5/5 heptacyclic ring system. Compound 2 represents an indole-diterpenoid with a new carbon skeleton derived from paxilline by the loss of three carbons (C-23/24/25). Compound 3 contains an additional oxygen atom between C-21 and C-22 compared to paxilline to form an unusual 6/5/5/6/6/7 hexacyclic ring system bearing a 1,3-dioxepane ring, which is rarely encountered in natural products. Compounds 1, 2, 4, and 6 showed inhibitory activities against protein tyrosine phosphatase 1B (PTP1B) with IC50 values of 14, 27, 23, and 13 μM, respectively.
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The structure of paxilline, a tremorgenic metabolite of bainier
James P. Springer, Jon Clardy, John M. Wells et al. · Tetrahedron Letters · 1975 · 95 citations