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Caption : figure s1. 2d hsqc nmr of eucalyptus cellulolytic enzyme lignin (cel). abbreviations of polysaccharides: x (xylan), β-d-glcp (β-d-glucopyranoside), α-d-xylp (α-d-xylopyranoside), and β-d-xylp (β-d-xylopyranoside)

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Caption : figure s2. preliminary analysis of the products from “s-s” β-aryl ether compound (syringyl glycol β-syringyl ether) by using gc-ms after alkaline treatment (1 mol/l naoh, 170 ºc, 1 h). according to a preliminary analysis, “s-s” β-aryl ether compound reacted to produce several kinds of condensed products (d3, d7, d17, d18 and t1)

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Caption : figure s3. preliminary analysis of the products from the cα-condensed β-aryl ether compound (t2) by using gc-ms after alkaline treatment (1 mol/l naoh, 170 ºc, 1 h). according to a preliminary analysis, apart from styryl ether products (d16 and d20), diaryl ethanols (d19) and diarylethenes (d6, d7 and d21) were presumably produced

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Caption : figure s4. evidence for the generation of two kinds of diarylethenes (1,1-diarylethene and 1,2-diarylethene) from cα-condensed β-aryl ether compound (t2). after separation of the products of t2, 1,1-diarylethene and 1,2-diarylethene were authenticated by analytical techniques. (a) shows that the compounds have different retention time whereas a similar ms information; (b) shows the representative signals of “=ch2” and “=ch-” in 2d hsqc nmr in 1,1-diarylethene and 1,2-diarylethene.

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Caption :  figure s5. analysis of the product of β-β model compound (syringaresinol, d14) after alkali treatment (1 mol/l naoh, 170 ºc, 1 h). (a) gc-ms analysis of the products. two signals with retention time of 52.0 min and 54.9 min in the chromatogram have similar ms information with the syringaresinol (retention time 55.1 min), which presumably come from the isomers of syringaresinol. (b) partial 2d hsqc nmr spectrum of the syringaresinol product. according to the assignment of multiple signals in the spectrum,7,8 two isomers of syringaresinol, dia-syringaresinol (d12) and epi-syringaresinol (d13), were proved to be generated in the product