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. 2020 Apr 7;9:e53582. doi: 10.7554/eLife.53582

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© 2020, Miyamoto et al

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Figure 5. — (A) Structures and simplified structures of type 1α, 1ω, 2α and 2ω WdiEs. Blue, red, and orange represent fatty diols, hydroxy FAs, and FAls, respectively. (B–D) Product ion scanning of the type 2ω WdiE ([1,ω-O-C18:1]-C16:0) (B) and the type 2α WdiE [(1,α-O-C18:1)-C16:0] (C) was performed using LC-MS/MS by selecting [M + H]⁺ ions with m/z 787.7 as the precursor ions. The MS spectra (B, C), the predicted cleavage positions (B, C), and the LC chromatogram (D) are shown. Synthesis schemes for the type 2ω WdiE hexadecane-1,16-diyl dioleate ([1,ω-O-C18:1]-C16:0) and type 2α WdiE 1-([hexadec-8-enoyl]oxy)-octadecan-2-yl oleate ([1,α-O-C18:1]-C16:0), and their fragment predictions in MS product ion scanning are provided in Figure 5—figure supplements 1–3. (E–G) Lipids were extracted from the meibomian glands of 12-month-old control (Tg-Cyp4f39^+/+ [n = 2] and Tg-Cyp4f39^+/– [n = 1]) (E–G) and Tg-Cyp4f39^–/– (n = 3) mice (E, G), and type 2ω WdiEs (E, F) and type 2α WdiEs (G) were analyzed by LC-MS/MS. (E, G) The peak areas of WdiE species of different chain lengths, with or without saturation, and their total amounts (insets) are shown. Values presented are means ± SD (*, p<0.05; **, p<0.01; Student’s t-test). The simplified structure representing each WdiE is shown below the graph. nd, not detected; Tg –/–, Tg-Cyp4f39^–/–. (F) Product ion scanning was performed by selecting the [C66:3 WdiE + H]⁺ ion, which has an m/z value of 981.7, as the precursor ion. The MS spectrum of type 2ω C66:3 WdiE is shown.

Figure 5—figure supplement 1. — (A) Structures and simplified structures of type 1α, 1ω, 2α and 2ω WdiEs. Blue, red, and orange represent fatty diols, hydroxy FAs, and FAls, respectively. (B–D) Product ion scanning of the type 2ω WdiE ([1,ω-O-C18:1]-C16:0) (B) and the type 2α WdiE [(1,α-O-C18:1)-C16:0] (C) was performed using LC-MS/MS by selecting [M + H]⁺ ions with m/z 787.7 as the precursor ions. The MS spectra (B, C), the predicted cleavage positions (B, C), and the LC chromatogram (D) are shown. Synthesis schemes for the type 2ω WdiE hexadecane-1,16-diyl dioleate ([1,ω-O-C18:1]-C16:0) and type 2α WdiE 1-([hexadec-8-enoyl]oxy)-octadecan-2-yl oleate ([1,α-O-C18:1]-C16:0), and their fragment predictions in MS product ion scanning are provided in Figure 5—figure supplements 1–3. (E–G) Lipids were extracted from the meibomian glands of 12-month-old control (Tg-Cyp4f39^+/+ [n = 2] and Tg-Cyp4f39^+/– [n = 1]) (E–G) and Tg-Cyp4f39^–/– (n = 3) mice (E, G), and type 2ω WdiEs (E, F) and type 2α WdiEs (G) were analyzed by LC-MS/MS. (E, G) The peak areas of WdiE species of different chain lengths, with or without saturation, and their total amounts (insets) are shown. Values presented are means ± SD (*, p<0.05; **, p<0.01; Student’s t-test). The simplified structure representing each WdiE is shown below the graph. nd, not detected; Tg –/–, Tg-Cyp4f39^–/–. (F) Product ion scanning was performed by selecting the [C66:3 WdiE + H]⁺ ion, which has an m/z value of 981.7, as the precursor ion. The MS spectrum of type 2ω C66:3 WdiE is shown.