This study systemically investigated the enantioselective bioaccumulation and degradation of etoxazole (ETZ) in earthworms along with the transcriptome and oxidative stress responses to ETZ enantiomer exposure. Based on the M-shaped bioaccumulation trends for ETZ enantiomers, R-ETZ was found to be preferentially bioaccumulated in earthworms. Sublethal toxicity analysis showed that S-ETZ induced greater changes in protein content, malondialdehyde content, detoxifying metabolic enzyme activity, and oxidative stress in earthworms, compared to those induced by R-ETZ. Integrated biomarker response analysis suggested that S-ETZ induced higher sublethal toxicity in earthworms than R-ETZ. Finally, transcriptomic analysis indicated that 845 and 314 genes were differentially expressed after R-ETZ and S-ETZ exposure, respectively, when compared to the nonexposed control group. Enrichment analysis indicated that these differentially expressed genes were primarily enriched in the digestion and absorption of proteins, lysosome, peroxisome, and peroxisome proliferator-activated receptor signaling pathways. These results suggest that earthworms exhibit distinct enantioselective responses to S-ETZ and R-ETZ. This study elucidates the enantioselective bioaccumulation, degradation, transcriptome, and oxidative stress characteristics of ETZ enantiomers in earthworms at the enantiomer level, offering a theoretical foundation to improve the risk assessment of ETZ in the soil-earthworm microsomes.

The volatile constituents of Blue Moon' and Blue Perfume' rose flowers, which, on an olfactory basis, are classified as a blue type' were analysed using Aromascope (R) technology (modified headspace technology) and solvent extraction methods followed by gas chromatographymass spectrometry analysis. One hundred and eighty components were identified in the headspace volatile components of Blue Moon' flower and 188 components were identified in solvent extracts. Among them, geraniol, nerol, citronellol, 1,3-dimethoxy-5-methylbenzene and dihydro--ionol were identified as the main odour components. On the other hand, in Blue Perfume', 165 components were identified in the headspace volatile components and 150 components were identified in solvent extracts. Among them, geraniol, nerol, citronellol, neral, and geranial were identified as the major odour compounds. From both rose flowers, three components were newly identified: 2-isopropyl-4-methylthiazole, (Z)-cyclododec-9-enolide (yuzu lactone), and methyl cis-(Z)-jasmonate. 2-Isopropyl-4-methylthiazole and methyl cis-(Z)-jasmonate were identified in both of the headspace components and solvent extracts of the two types of rose flower, and then yuzu lactone was identified only in solvent extracts as the one of the minor components. Several components identified in both flowers have asymmetric carbon atoms in their molecules, leading us to analyse their chirality. For the first time, the enantiomer ratios of linalool, (E)-nerolidol, theaspiranes and dihydro--ionol could be assigned by multi-dimensional gas chromatographymass spectrometry. The results were as follows in both rose flowers. The ratio of the (S)-enantiomer vs. the (R)-enantiomer of linalool was 8:92. Only the (S)-enantiomer was detected for (E)-nerolidol and dihydro--ionol. The ratios of the (2R,5R)-enantiomer vs. the (2S,5S)-enantiomer in theaspirane A and the (2R,5S)-enantiomer vs. the (2S,5R)-enantiomer in theaspirane B were about 4:96. Copyright (c) 2013 John Wiley & Sons, Ltd.