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. 2020 Nov 27;33(1):129–152. doi: 10.1093/plcell/koaa014

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© The Author(s) 2020. Published by Oxford University Press on behalf of American Society of Plant Biologists.

This is an Open Access article distributed under the terms of the Creative Commons Attribution License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted reuse, distribution, and reproduction in any medium, provided the original work is properly cited.

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Lignans and neolignans. (A) The biosynthetic pathways of lignans and neolignans. DIR, dirigent protein; LAC, laccase; PLR, pinoresinol/lariciresinol reductase; PrR, pinoresinol reductase; PRX, peroxidase; SIRD, secoisolariciresinol dehydrogenase. (B) Structures of neolignans in Arabidopsis seeds (see also Supplemental Table 1). G, Guaiacyl moiety; S, Syringyl moiety; SC, sinapoylcholine; FC, feruloylcholine; Hex, hexose. Asterisks indicate the compounds authenticated with chemically synthesized standards. (C) Synthetic scheme for neolignans SC(4-O-8)G (1) and FC(4-O-8)G (4). Reaction conditions: (i) acetone/K₂CO₃/reflux; (ii) dioxane/K₂CO₃/formaldehyde/r.t.; (iii) ethanol/NaBH₄/r.t.; (iv) NaOH aq./r.t.; (v) DMF/bromocholine bromide/NaOH/90°C; (vi) preparative HPLC. r.t., room temperature.