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. 2019 May 9;14(5):e0216753. doi: 10.1371/journal.pone.0216753

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© 2019 Chiu et al

This is an open access article distributed under the terms of the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original author and source are credited.

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Fig 2 — Panels A-D show different regions of the same chromatograms of CYP6DJ1 assays and extracts of beetles treated with (–)-(4S)-limonene. (A) (1S,2R,4S)-Limonene-1,2-epoxide (peak 1) and (1R,2S,4S)-limonene-1,2-epoxide (peak 2) were detected in beetles treated with (–)-(4S)-limonene. (4S,8S)-Limonene-8,9-epoxide (peak 3) and (4S,8R)-limonene-8,9-epoxide (peak 4) were produced by CYP6DJ1 in in vitro assays with (–)-(4S)-limonene and were detected in beetles treated with (–)-(4S)-limonene. (B) An unidentified product (peak 5), (–)-trans-(3S,4R)-isopiperitenol (peak 6), (–)-cis-(4R,6R)-carveol (peak 7) and (–)-trans-(4R,6S)-carveol (peak 8) were detected in beetles treated with (–)-(4S)-limonene. (C) (4S)-Perilla alcohol (peak 9) was produced in CYP6DJ1 assays with (–)-(4S)-limonene and was detected in beetles treated with (–)-(4S)-limonene. (D) (4S)-Limonene-1,2-diol was detected in beetles treated with (–)-(4S)-limonene. Chromatograms are shown with the total of the extracted ions 91, 94, 108, 109, 119, 121, 137, 152 m/z. Retention indices and mass spectra of peaks 1–10 are shown in S2 Table and S4 and S5 Figs.