ABSTRACT
A new cyclopropane-containing sesquiterpenoid, phellilane L (1), was isolated from the medicinal mushroom Phellinus linteus ("Meshimakobu" in Japanese), a member of the Hymenochaetaceae family and a well-known fungus that is widely used in East Asia. The planar structure of 1 was determined on the basis of spectroscopic analysis. The authors achieved the first total synthesis of 1. Our protecting group-free synthesis features a highly stereoselective one-pot synthesis involving an intermolecular alkylation/cyclization/lactonization strategy for construction of the key cyclopropane-γ-lactone intermediate. Additionally, our synthesis determined the absolute configuration of phellilane L (1).
Subject(s)
Agaricales/chemistry , Basidiomycota/chemistry , Sesquiterpenes/chemistry , Chemistry, Pharmaceutical , Molecular StructureABSTRACT
This corrects the article DOI: 10.1038/ja.2017.35.
Subject(s)
Anti-Bacterial Agents/isolation & purification , Plant Extracts/chemistry , Porphyromonas gingivalis/drug effects , Sesquiterpenes/isolation & purification , Anti-Bacterial Agents/chemistry , Anti-Bacterial Agents/pharmacology , Microbial Sensitivity Tests , Phellinus , Sesquiterpenes/chemistry , Sesquiterpenes/pharmacologyABSTRACT
Activity-guided fractionations of leaf extracts from Laurus nobilis L. led to the isolation of a known sesquiterpene lactone, deacetyl laurenobiolide (1). Compound 1 showed antimicrobial activity against periopathic pathogens (Actinomyces viscosus, Porphyromonas gingivalis, Prevotella intermedia and Actinobacillus actinomycetemcomitans), opportunistic Gram-positive bacteria (Staphylococcus aureus and Streptococcus pyogenes) and fungi (Candida albicans, Cryptococcus neoformans and Aspergillus fumigatus). Furthermore, acetylation and cyclisation of deacetyl laurenobiolide (1) yielded laurenobiolide (2) and a new compound, (5S,6R,7S,8S,10R)-6,8-dihydroxyeudesma-4(15),11(13)-dien-12-oic acid 12,8-lactone (3), respectively. Compounds 2 and 3 also showed antimicrobial activities. All compounds 1-3 demonstrated growth inhibitory effects with minimum inhibitory concentrations ranging from 31 to 1000 µg mL(-1). This is the first report of compounds 1-3 showing antimicrobial activities.
