A new pathway for the degradation of a sesquiterpene alcohol, nerolidol by Alcaligenes eutrophus.
An oxidative pathway hitherto unknown for the degradation of a sesquiterpene alcohol, nerolidol (I) by Alcaligenes eutrophus is presented. Fermentation of nerolidol (I) by this organism in a mineral salts medium resulted in the formation of geranylacetone (II) and an optically active alcohol (S)-(+)-geranylacetol (III), as major metabolites. Nerolidol (I) induced cells readily transformed 1,2-epoxynerolidol (IV) and 1,2-dihydroxynerolidol (V) into geranylacetone (II). These cells also exhibited their ability to carry out stereospecific reduction of II into (S)-(+)-geranylacetol (III). Oxygen uptake studies clearly indicated that nerolidol induced cells oxidized compounds II, III, IV, V and ethyleneglycol. Based on these observations a new oxidative pathway for the degradation of I is suggested which envisages the epoxidation of the terminal double bond, opening of the epoxide and cleavage between C-2 and C-3 in a manner similar to the periodate oxidation of diol.
Department of Organic Chemistry, Indian Institute of Science, Bangalore.
K M
KM
Madyastha
T L
TL
Gururaja
D000421:Alcaligenes / Q000378:metabolism*; D001673:Biodegradation, Environmental; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D010100:Oxygen / Q000378:metabolism; D012717:Sesquiterpenes / Q000378:metabolism*
D012717:Sesquiterpenes; C037055:nerolidol; D010100:Oxygen