Biodegradation of juvenoid diastereoisomers: radio-HPLC and MS analysis.
Microbial degradation of two diastereoisomeric forms 2 and 3 of a selected juvenoid (insect juvenile hormone bioanalog), ethyl N-{2-{4-[(2-hydroxycyclohexyl)methyl]phenoxy}ethyl}carbamate was studied and the degradation products analyzed. Degradation experiments were performed using simple modeling under laboratory conditions. A Candida sp. strain T1, isolated from soil, was chosen as a biodegradation species. Radiolabeling of the studied compounds 2 and 3 was used in combination with radio-HPLC and MS analysis to increase the limits of detection, monitoring and isolation of trace quantities of the products of degradation and/or transformation. Resulting from the microbial processes using 2 or 3 as source compounds, three identical products (4-6) of their biodegradation were produced. Compound 2 also afforded two additional products (7, 8). Radio-HPLC analysis and separation, and subsequent MS analysis of the degradation mixtures resulted in identification of the degradation products. The degree and the rate of biodegradation of 2 and 3 were analyzed after 1, 3 and 7 days from the beginning of the experiment.
Tykva
Richard
R
Institute of Organic Chemistry and Biochemistry, Academy of Sciences of the Czech Republic, Flemingovo námestí 2, CZ-16610 Prague 6, Czech Republic.
Wimmer
Zdenek
Z
Vlasáková
Vera
V
Novák
Jaroslav
J
Havlícek
Libor
L
D000818:Animals; D001673:Biodegradation, Environmental; D001711:Biotransformation; D002219:Carbamates / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D003621:Daphnia / Q000378:metabolism*; D007313:Insecta; D007553:Isotope Labeling; D007605:Juvenile Hormones / Q000737:chemistry / Q000378:metabolism* / Q000633:toxicity; D013058:Mass Spectrometry / Q000379:methods; D012988:Soil Microbiology; D013237:Stereoisomerism; D013997:Time Factors
D002219:Carbamates; D007605:Juvenile Hormones; C115356:ethyl N-(2-(4-((2,2-(ethylenedioxy)cyclohexyl)methyl)phenoxy)ethyl)carbamate