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Further Antibacterial Geranium macrorrhizum L. Metabolites and Synthesis of Epoxygermacrones
Author(s) -
Radulović Niko S.,
Zlatković Dragan,
Dekić Milan,
StojanovićRadić Zorica
Publication year - 2014
Publication title -
chemistry and biodiversity
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.427
H-Index - 70
eISSN - 1612-1880
pISSN - 1612-1872
DOI - 10.1002/cbdv.201300295
Subject(s) - chemistry , geranium , bacillus subtilis , geraniaceae , antimicrobial , stereochemistry , antibacterial activity , minimum inhibitory concentration , botany , organic chemistry , bacteria , biology , genetics , cultivar
4,5‐ and 1,10‐Epoxygermacrones were isolated from the essential oil of aerial parts of Geranium macrorrhizum L. (Geraniaceae) . The structures of the epoxy derivatives were deduced from their 1D‐ and 2D‐NMR spectra, molecular modeling, and confirmed by synthesis starting from germacrone. The epoxy compounds were screened for their antimicrobial activities by a microdilution assay, which revealed high activities of both compounds against Bacillus subtilis (minimum inhibitory concentrations ( M/C s) determined were 4.3 and 43 nmol/ml for 1,10‐ and 4,5‐epoxygermacrone, resp.) and Pseudomonas aeruginosa (0.043 and 0.855 μmol/ml for 1,10‐ and 4,5‐epoxygermacrone, resp.). The discovery and observed activity of the two epoxides fills the gap in our knowledge of the active principles in this highly renowned ethnomedicinal plant species.