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. 2019 Jul 18;17(7):e3000347. doi: 10.1371/journal.pbio.3000347

Fig 5. Anthraquinone identification and characterisation.

Fig 5

(a) EIC in negative ionisation mode for shunt metabolites described in Fig 2A, in addition to anthraquinones produced by P. luminescens TT01 and predicted pathway end compounds. All EICs represent theoretical mass for [M-H]− ± 5 ppm. Red, blue, and black lines represent EICs of E. coli BL21 (host control), E. coli BL21 pACYCDuet-1 (plasmid control), and E. coli BL21 pACYCAnthraquinone normalized to final cell density. EICs displaying masses from positive ionisation mode are detailed in S17 Fig. (b) Schematic diagram showing intramolecular couplings between nuclei of E. coli–produced AQ256, which were determined by COSY (green), HSQC (grey), and HMBC (blue scale) two-dimensional NMR spectroscopies. Coupling constants are detailed in Materials and methods. COSY, correlation spectroscopy; DMAC, 3,8-dihydroxy-methylanthraquinone carboxylic acid; EIC, extracted ion chromatogram; HMBC, heteronuclear multiple bond correlation; HSQC, heteronuclear single quantum correlation; NMR, Nuclear magnetic resonance.