Discovery of two novel laccase-like multicopper oxidases from Pleurotus citrinopileatus and their application in phenolic oligomer synthesis

Zerva, A.; Pentari, C.; Termentzi, A.; America, A. H. P.; Zouraris, D.; Bhattacharya, S. K.; Karantonis, A.; Zervakis, G. I.; Topakas, E.

doi:10.1186/s13068-021-01937-7

Biotechnology for Biofuels and Bioproducts

Table 6 LC–MS identification of the main ions detected during oxidation of ferulic acid by PcLac1 and PcLac2

From: Discovery of two novel laccase-like multicopper oxidases from Pleurotus citrinopileatus and their application in phenolic oligomer synthesis

Compound	Rt (min)	m/z [M-H]⁻	MF	MS/MS	Identification	PcLac1 samples	PcLac2 samples
Dimers
1	7.07	297.111	C₁₈H₁₇O₄	146 (C₉H₆O₂) 109 (C₆H₅O₂)	Double-decarboxylated diferulic acid	Minor	Major
2	7.07	341	C₁₉H₁₇O₆	281 (C₁₇H₁₃O₄), 267 (C₁₆H₁₁O₄), 209 (C₁₄H₉O₂), 159 (C₁₀H₇O₂), 146 (C₉H₆O₂)	Decarboxylated diferulic acid	Major	Major
3	7.28	385	C₂₀H₁₇O₈	267 (C₁₆H₁₁O₄), 239 (C₁₅H₁₁O₃)	Diferulic acid	Major	Major
4	7.29	341	C₁₉H₁₇O₆	281 (C₁₇H₁₃O₄), 267 (C₁₆H₁₁O₄), 209 (C₁₄H₉O₂), 159 (C₁₀H₇O₂), 146 (C₉H₆O₂)	Decarboxylated diferulic acid	Major	Major
5	7.99	341	C₁₉H₁₇O₆	281 (C₁₇H₁₃O₄), 267 (C₁₆H₁₁O₄), 209 (C₁₄H₉O₂), 159 (C₁₀H₇O₂), 146 (C₉H₆O₂)	Decarboxylated diferulic acid	Major	Major
Trimers
6	7.40	577	C₃₀H₂₅O₁₂	193	Triferulic acid	Not detected	Major
7	7.62	533	C₂₉H₂₆O₁₀	193	Triferulic acid, decarboxylated	Not detected	Major
8	7.63	577	C₃₀H₂₅O₁₂	193	Triferulic acid	Not detected	Major
9	7.65	533	C₂₉H₂₆O₁₀	193 (C₁₀H₉O₄),	Triferulic acid, decarboxylated	Minor	Major
10	7.67	533	C₂₉H₂₆O₁₀	193	Triferulic acid, decarboxylated	Not detected	Major
11	8.02	533	C₂₉H₂₆O₁₀	193	Triferulic acid, decarboxylated	Minor	Major
12	8.21	533	C₂₉H₂₆O₁₀	193	Triferulic acid, decarboxylated	Minor	Major
13	8.35	533	C₂₉H₂₆O₁₀	193	Triferulic acid, decarboxylated	Minor	Major
14	8.35	565	C₃₀H₂₉O₁₁	193 (C₁₀H₉O₄), 178 (C₉H₆O₄), 149 (C₉H₉O₂), 134 (C₈H₆O₂)	Unknown triferulic acid	Major	Major
15	8.63	533	C₂₉H₂₆O₁₀	193	Triferulic acid, decarboxylated	Not detected	Minor
Others
16	7.5	551	C₂₉H₂₈O₁₁	193 (C₁₀H₉O₄), 178 (C₉H₆O₄), 149 (C₉H₉O₂), 134 (C₈H₆O₂)	Triferulic acid, decarboxylated-H₂O*	Detected	Detected

*The MS/MS shows that it is a triferulic acid derivative but it is not obvious how. A carboxyl group and a H₂O molecule are missing

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