Antimicrobial Cuparene-Type Sesquiterpenes, Enokipodins C and D, from a Mycelial Culture of Flammulina velutipes

• Published in: Journal of natural products (Washington, D.C.) Vol. 64; no. 7; pp. 932 - 934
• Main Authors: ISHIKAWA, Noemia Kazue, FUKUSHI, Yukiharu, YAMAJI, Keiko, TAHARA, Satoshi, TAKAHASHI, Kunihide
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 01.07.2001; Amer Chemical Soc; American Society of Pharmacognosy
• Subjects: Antifungal Agents - chemistry; Antifungal Agents - isolation & purification; Antifungal Agents - pharmacology; Bacillus subtilis; Bacillus subtilis - drug effects; Basidiomycota - chemistry; Biological and medical sciences; Chemistry, Medicinal; Chlorobenzoates - chemistry; Cladosporium - drug effects; Cladosporium herbarum; enokipodin C; enokipodin D; Escherichia coli - drug effects; Flammulina velutipes; General pharmacology; Japan; Life Sciences & Biomedicine; Medical sciences; Pharmacognosy. Homeopathy. Health food; Pharmacology & Pharmacy; Pharmacology. Drug treatments; Plant Sciences; Pseudomonas fluorescens - drug effects; Science & Technology; Sesquiterpenes - chemistry; Sesquiterpenes - isolation & purification; Sesquiterpenes - pharmacology; Staphylococcus aureus; Staphylococcus aureus - drug effects; Japan; SUBSTANCES; (+/-)-ALPHA-CUPARENONE; MUSHROOMS; Bacillus subtilis; Ketol; Basidiomycetes; Bacillaceae; Oxygen heterocycle; Antimicrobial agent; Medicinal plant; Fungi; Antifungal agent; Cladosporium herbarum; Bacillales; Bacteria; Micrococcales; Micrococcaceae; Aromatic compound; Fungi Imperfecti; Edible fungi; Monocyclic compound; Staphylococcus aureus; Thallophyta; Culture medium; Quinone; Benzoquinone derivatives; Hemiacetal; Tricyclic compound; Ketone; In vitro; Biological activity; Plant origin; Benzenic compound; Isolation; Antibacterial agent; Structural analysis
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np000593r

Two new cuparene-type sesquiterpenes, enokipodins C (1) and D (2), were isolated from culture medium of an edible mushroom, Flammulina velutipes, along with enokipodins A (3) and B (4). The structures of 1 and 2 were determined using spectroscopic methods (HRMS, H-1 and C-13, and 2D NMR). The absolute configuration of enokipodin C was determined from the observed IH NMR chemical shifts and NOEs in NOESY experiments after conversion into the corresponding esters with the chiral reagent 2-(2'-methoxy-1'-naphthyl)-3,4-dichlorobenzoic acid. All the metabolites showed antimicrobial activity against a fungus, Cladosporium herbarum, and Gram-positive bacteria, Bacillus subtilis and Staphylococcus aureus.