Antimicrobial cuparene-type sesquiterpenes, enokipodins C and D, from a mycelial culture of Flammulina velutipes.
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, (1)H and (13)C, and 2D NMR). The absolute configuration of enokipodin C was determined from the observed (1)H 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.
Ishikawa
N K
NK
Division of Environmental Resources and Division of Applied Bioscience, Graduate School of Agriculture, Hokkaido University, Kita-ku, Sapporo 060-8589, Japan.
Fukushi
Y
Y
Yamaji
K
K
Tahara
S
S
Takahashi
K
K
D000935:Antifungal Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D001412:Bacillus subtilis / Q000187:drug effects; D001487:Basidiomycota / Q000737:chemistry*; D002723:Chlorobenzoates / Q000737:chemistry; D002963:Cladosporium / Q000187:drug effects; D004926:Escherichia coli / Q000187:drug effects; D007564:Japan; D011551:Pseudomonas fluorescens / Q000187:drug effects; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D013211:Staphylococcus aureus / Q000187:drug effects
C435775:2-(2'-methoxy-1'-naphthyl)-3,4-dichlorobenzoic acid; D000935:Antifungal Agents; D002723:Chlorobenzoates; D012717:Sesquiterpenes