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. Author manuscript; available in PMC: 2019 Feb 28.
Published in final edited form as: J Am Chem Soc. 2018 Feb 16;140(8):2841–2852. doi: 10.1021/jacs.7b11811

Figure 5.

Figure 5

a) Generic structures of N-acylethanolamine, GPE, and GPE glucosides. b) Levels of EPEA (m/z 346.2741), arachidonic acid ethanolamides (AEA, m/z 348.2898) and other ethanolamides are significantly reduced in the metabolome of daf-22 growth medium, but largely unaffected in the L1 metabolome. The two peaks for AEA correspond to N- and O-acylethanolamines as determined by MS/MS (Tables S2–S9). c) Structures of npar#1 and ubas#6 previously identified from wildtype P pacificus. d) ES+ EICs for m/z 616.2368, showing two peaks present in Ppa-daf-22 but not in wildtype. Proposed structures for two isomers along with selected MS/MS fragmentations used in structure assignments are shown in e) and full ES+ MS/MS spectra for both isomers are shown in f) for phesad#1 and in g) for phesad#2.