Organic Letters · 2016 · 116 citations · 28 references
Life SciencesBiochemistryBotanyPlant BiochemistrySteroid BiochemistryStructure-activity RelationshipsFungal Secondary MetabolitesSecondary Metabolite BiosynthesisSteroid BiosynthesisSteroid StructureStructure-activity Relationship AnalysisTerpenoid BiosynthesisAnti-inflammatory ActivityAnti-inflammatory ResponseBioactive Fungal MetabolitesEndophytic Fungal MetabolitesFungal Bioactive CompoundsFungal Metabolite BiosynthesisFungal Terpenoid BiosynthesisStructure Elucidation Of Fungal Metabolites
Two new functionalized ergostane-type steroids, phomopsterones A (1) and B (2), were isolated from the plant-derived Phomopsis sp. TJ507A. Their structures were determined on the basis of spectroscopic data, a modified Mosher's method, X-ray crystallographic analysis, and quantum chemical calculations. Compound 1 is an unprecedented ergosteroid featuring a rearranged bicyclo[3.3.1]nonane motif resulting from B-ring scission and a subsequent 180° rotation of the ring A during biosynthesis. Compound 2 exhibited anti-inflammatory activity.
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Phomopsichalasin, a novel antimicrobial agent from an endophytic Phomopsis sp.
Wendy S. Horn, MSJ Simmonds, Robert E. Schwartz et al. · Tetrahedron · 1995 · 129 citations