The DOI matches its Crossref record; 29 of the 29 references it cites were found in a registry or an index.
Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls
Abstract
Seven isomeric dehydrodimers of ferulic acid (4-hydroxy-3-methoxycinnamic acid) have been synthesized and identified in extracts of saponified cell walls of cocksfoot, switchgrass, and suspension-cultured corn. Dehydrodimers (E,E)-4,4′-dihydroxy-5,5′-dimethoxy-3,3′-bicinnamic acid, trans-5-[(E)-2-carboxyvinyl]-2-(4-hydroxy-3-methoxyphenyl)-7-methoxy-2,3-dihydrobenzofuran-3-carboxylic acid, (Z)-β-{4-[(E)-2-carboxyvinyl]-2-methoxyphenoxy}-4-hydroxy-3-methoxycinnamic acid, (E)-3-{4-[(E)-2-carboxyvinyl]-2-methoxyphenoxy}-4-hydroxy-5-methoxycinnamic acid, (E,E)-4,4′-dihydroxy-3,5′-dimethoxy-β,3′-bicinnamic acid, 4,4′-dihydroxy-3,3′-dimethoxy-β,β′-bicinnamic acid, and trans-7-hydroxy-1-(4-hydroxy-3-methoxyphenyl)-6-methoxy-1,2-dihydronaphthalene-2,3-dicarboxylic acid, all arise from oxidative coupling of ferulate esters in cell walls and represent products of 8–5, 8–8, 8–O–4, 4–O–5, and 5–5 radical coupling. Prior literature has acknowledged only the presence of the 5–5-coupled dehydrodimer (E,E)-4,4′-dihydroxy-5,5′-dimethoxy-3,3′-bicinnamic acid. Consequently, by measuring only a single dehydrodimer and assuming inappropriate response factors, ferulate dehydrodimers have been underestimated by factors of up to 20. Synthetic routes to all seven isomers have been developed to provide structural authentication and determination of GC response factors.
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Cites
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Sensitivity-enhanced two-dimensional heteronuclear shift correlation NMR spectroscopy
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Pathway of p-Coumaric Acid Incorporation into Maize Lignin As Revealed by NMR
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Self-citationLinkage of p-coumaroyl and feruloyl groups to cell-wall polysaccharides of barley straw
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Cited by
Lignin structure and its engineering
Ralph, J., Lapierre, C., & Boerjan, W. (2019) · Current Opinion in Biotechnology · doi:10.1016/j.copbio.2019.02.019 · Cited by 1,054
Self-citationDeconstruction of Lignocellulosic Biomass to Fuels and Chemicals
Chundawat, S. P. S., Beckham, G. T., Himmel, M. E., & Dale, B. E. (2011) · Annual Review of Chemical and Biomolecular Engineering · doi:10.1146/annurev-chembioeng-061010-114205 · Cited by 1,017
STRUCTURE AND BIOGENESIS OF THE CELL WALLS OF GRASSES
Carpita, N. C. (1996) · Annual Review of Plant Physiology and Plant Molecular Biology · doi:10.1146/annurev.arplant.47.1.445 · Cited by 881
Arabinoxylans and Endoxylanases in Wheat Flour Bread-making
Courtin, C. M., & Delcour, J. A. (2002) · Journal of Cereal Science · doi:10.1006/jcrs.2001.0433 · Cited by 720
Ralph, J., Grabber, J. H., & Hatfield, R. D. (1995) · Carbohydrate Research · doi:10.1016/0008-6215(95)00237-n · Cited by 448
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Metadata
- Authors
- Ralph, J., Quideau, S., Grabber, J. H., & Hatfield, R. D.
- Venue
- Journal of the Chemical Society, Perkin Transactions 1
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 1994
- Issue
- 23
- Pages
- 3485
- ISSN
- 1364-5463 (ISSN-L)
- 0300-922X
- OpenAlex
- W2037683681
- Cited by
- 462
- References
- 29
- FWCI
- 13.26
- Type
- journal article
- Language
- en
- Open access
- closed
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