메뉴 건너뛰기




Volumn 50, Issue 21, 2002, Pages 6008-6016

Model studies of ferulate - Coniferyl alcohol cross-product formation in primary maize walls: Implications for lignification in grasses

Author keywords

Coniferyl alcohol; Cross coupling; Cross link; Cross product; Dehydrogenation polymer; Diferulic acids; Ferulic acid; Lignin; Nucleation site; Primary cell wall; Zea mays

Indexed keywords

CONIFERYL ALCOHOL; FERULIC ACID; LIGNIN; XYLAN;

EID: 0037048762     PISSN: 00218561     EISSN: None     Source Type: Journal    
DOI: 10.1021/jf0205312     Document Type: Article
Times cited : (108)

References (29)
  • 1
    • 0026245034 scopus 로고
    • Isolation and characterization of a diferuloyl arabinoxylan hexasaccharide from bamboo shoot cell-walls
    • Ishii, T. Isolation and characterization of a diferuloyl arabinoxylan hexasaccharide from bamboo shoot cell-walls. Carbohydr. Res. 1991, 219, 15-22.
    • (1991) Carbohydr. Res. , vol.219 , pp. 15-22
    • Ishii, T.1
  • 2
    • 84986777998 scopus 로고
    • Monomeric and dimeric phenolic acids released from cell walls of grasses by sequential treatment with sodium hydroxide
    • Hartley, R. D.; Morrison, W. H., III. Monomeric and dimeric phenolic acids released from cell walls of grasses by sequential treatment with sodium hydroxide. J. Sci. Food Agric. 1991, 55, 365-375.
    • (1991) J. Sci. Food Agric. , vol.55 , pp. 365-375
    • Hartley, R.D.1    Morrison W.H. III2
  • 3
    • 37049067514 scopus 로고
    • Lignin-feruloyl ester cross-links in grasses. Part 1. Incorporation of feruloyl esters into coniferyl alcohol dehydrogenation polymers
    • Ralph, J.; Helm, R. F.; Quideau, S.; Hatfield, R. D. Ligninferuloyl ester cross-links in grasses. Part 1. Incorporation of feruloyl esters into coniferyl alcohol dehydrogenation polymers. J. Chem. Soc., Perkin Trans. 1 1992, 2961-2969.
    • (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 2961-2969
    • Ralph, J.1    Helm, R.F.2    Quideau, S.3    Hatfield, R.D.4
  • 4
    • 33745044318 scopus 로고
    • Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls
    • Ralph, J.; Quideau, S.; Grabber, J. H.; Hatfield, R. D. Identification and synthesis of new ferulic acid dehydrodimers present in grass cell walls. J. Chem. Soc., Perkin Trans. 1 1994, 3485-3498.
    • (1994) J. Chem. Soc., Perkin Trans. 1 , pp. 3485-3498
    • Ralph, J.1    Quideau, S.2    Grabber, J.H.3    Hatfield, R.D.4
  • 5
    • 0028816429 scopus 로고
    • Ferulate cross-linking in cell walls isolated from maize cell suspensions
    • Grabber, J. H.; Hatfield, R. D.; Ralph, J.; Zon, J.; Amrhein, N. Ferulate cross-linking in cell walls isolated from maize cell suspensions. Phytochemistry 1995, 40, 1077-1082.
    • (1995) Phytochemistry , vol.40 , pp. 1077-1082
    • Grabber, J.H.1    Hatfield, R.D.2    Ralph, J.3    Zon, J.4    Amrhein, N.5
  • 6
    • 0001449541 scopus 로고
    • New ether-linked ferulic acid-coniferyl alcohol dimers identified in grass straws
    • Jacquet, G.; Pollet, B.; Lapierre, C.; Mhamdi, F.; Rolando, C. New ether-linked ferulic acid-coniferyl alcohol dimers identified in grass straws. J. Agric. Food Chem. 1995, 43, 2746-2751.
    • (1995) J. Agric. Food Chem. , vol.43 , pp. 2746-2751
    • Jacquet, G.1    Pollet, B.2    Lapierre, C.3    Mhamdi, F.4    Rolando, C.5
  • 7
    • 0029117332 scopus 로고
    • Lignin-ferulate cross-links in grasses: Active incorporation of ferulate polysaccharide esters into ryegrass lignins
    • Ralpfi, J.; Grabber, J. H.; Hatfield, R. D. Lignin-ferulate cross-links in grasses: active incorporation of ferulate polysaccharide esters into ryegrass lignins. Carbohydr. Res. 1995, 275, 167-178.
    • (1995) Carbohydr. Res. , vol.275 , pp. 167-178
    • Ralpfi, J.1    Grabber, J.H.2    Hatfield, R.D.3
  • 8
    • 0000870167 scopus 로고    scopus 로고
    • Lignin-ferulate cross-links in grasses. Part 4. Incorporation of 5-5-coupled diferulate into lignin
    • Quideau, S.; Ralph, J. Lignin-ferulate cross-links in grasses. Part 4. Incorporation of 5-5-coupled diferulate into lignin. J. Chem. Soc., Perkin Trans. 1 1997, 2351-2358.
    • (1997) J. Chem. Soc., Perkin Trans. 1 , pp. 2351-2358
    • Quideau, S.1    Ralph, J.2
  • 9
    • 0034524722 scopus 로고    scopus 로고
    • Cross-linking of maize walls by ferulate dimerization and incorporation into lignin
    • Grabber, J. H.; Ralph, J.; Hatfield, R. D. Cross-linking of maize walls by ferulate dimerization and incorporation into lignin. J. Agric. Food Chem. 2000, 48, 6106-6113.
    • (2000) J. Agric. Food Chem. , vol.48 , pp. 6106-6113
    • Grabber, J.H.1    Ralph, J.2    Hatfield, R.D.3
  • 10
    • 0003126240 scopus 로고
    • Primary cell wall metabolism
    • Milflin, B. J., Ed.; Oxford University Press: New York
    • Fry, S. C. Primary cell wall metabolism. In Oxford Surveys of Plant Molecular and Cell Biology; Milflin, B. J., Ed.; Oxford University Press: New York, 1985; pp 1-42.
    • (1985) Oxford Surveys of Plant Molecular and Cell Biology , pp. 1-42
    • Fry, S.C.1
  • 11
    • 0002255130 scopus 로고
    • Phenylpropanoid metabolism in cell walls. An overview
    • Lewis, N. G., Paice, M. G., Eds.; American Chemical Society: Washington, DC
    • Yamamoto, E.; Bokelman, G. H.; Lewis, N. G. Phenylpropanoid metabolism in cell walls. An overview. In Plant Cell Wall Polymers. Biogenesis and Biodegradation; Lewis, N. G., Paice, M. G., Eds.; American Chemical Society: Washington, DC, 1989; pp 68-88.
    • (1989) Plant Cell Wall Polymers. Biogenesis and Biodegradation , pp. 68-88
    • Yamamoto, E.1    Bokelman, G.H.2    Lewis, N.G.3
  • 12
    • 85102324334 scopus 로고
    • Lignin/hydroxycinnamic acid/polysaccharide complexes: Synthetic models for regiochemical characterization
    • Jung, H. G., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI
    • Ralph, J.; Helm, R. F. Lignin/hydroxycinnamic acid/polysaccharide complexes: Synthetic models for regiochemical characterization. In Forage Cell Wall Structure and Digestibility; Jung, H. G., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI, 1993; pp 201-246.
    • (1993) Forage Cell Wall Structure and Digestibility , pp. 201-246
    • Ralph, J.1    Helm, R.F.2
  • 13
    • 0001567529 scopus 로고
    • The morphological origin of milled wood lignin
    • Whiting, P.; Goring, D. A. I. The morphological origin of milled wood lignin. Svensk Papperstidn. 1981, 84, R120-RI22.
    • (1981) Svensk Papperstidn , vol.84
    • Whiting, P.1    Goring, D.A.I.2
  • 14
    • 85102331755 scopus 로고
    • Comprehensive model of the lignified plant cell wall
    • Jung, H. G., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI
    • Terashima, N.; Fukushima, K.; He, L.-F.; Takabe, K. Comprehensive model of the lignified plant cell wall. In Forage Cell Wall Structure and Digestibility; Jung, H. G., Buxton, D. R., Hatfield, R. D., Ralph, J., Eds.; ASA-CSSA-SSSA: Madison, WI, 1993; pp 247-270.
    • (1993) Forage Cell Wall Structure and Digestibility , pp. 247-270
    • Terashima, N.1    Fukushima, K.2    He, L.-F.3    Takabe, K.4
  • 15
    • 0031177709 scopus 로고    scopus 로고
    • Study of lignification by noninvasive techniques in growing maize intemodes
    • Joseleau, J. P.; Ruel, K. Study of lignification by noninvasive techniques in growing maize intemodes. Plant Physiol. 1997, 114, 1123-1133.
    • (1997) Plant Physiol. , vol.114 , pp. 1123-1133
    • Joseleau, J.P.1    Ruel, K.2
  • 16
    • 0020199907 scopus 로고
    • Observations on the use of guaiacol and 2,2′-azino-di(3-ethylbenzthiazoline-6-sulfonic acid) as peroxidase substrates
    • Makinen, K.; Terovuo, J. Observations on the use of guaiacol and 2,2′-azino-di(3-ethylbenzthiazoline-6-sulfonic acid) as peroxidase substrates. Anal. Biochem. 1982, 126, 100-108.
    • (1982) Anal. Biochem. , vol.126 , pp. 100-108
    • Makinen, K.1    Terovuo, J.2
  • 17
    • 37049079319 scopus 로고
    • Lignin-feruloyl ester cross-links in grasses. Part 2. Model compound syntheses
    • Ralph, J.; Helm, R. F.; Quideau, S. Lignin-feruloyl ester cross-links in grasses. Part 2. Model compound syntheses. J. Chem. Soc., Perkin Trans. 1 1992, 2971-2980.
    • (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 2971-2980
    • Ralph, J.1    Helm, R.F.2    Quideau, S.3
  • 19
    • 0000292769 scopus 로고
    • Lignin-hydroxycinnamyl model compounds related to forage cell wall structure 1. Ether-linked structures
    • Helm, R. F.; Ralph, J. Lignin-hydroxycinnamyl model compounds related to forage cell wall structure. 1. Ether-linked structures. J. Agric. Food Chem. 1992, 40, 2167-2175.
    • (1992) J. Agric. Food Chem. , vol.40 , pp. 2167-2175
    • Helm, R.F.1    Ralph, J.2
  • 20
    • 0031753576 scopus 로고    scopus 로고
    • Severe inhibition of maize wall degradation by synthetic lignins formed with coniferaldehyde
    • Grabber, J. H.; Ralph, J.; Hatfield, R. D. Severe inhibition of maize wall degradation by synthetic lignins formed with coniferaldehyde. J. Sci. Food Agric. 1998, 78, 81-87.
    • (1998) J. Sci. Food Agric. , vol.78 , pp. 81-87
    • Grabber, J.H.1    Ralph, J.2    Hatfield, R.D.3
  • 22
    • 0020553586 scopus 로고
    • Stereochemical aspects of addition reactions involving lignin model quinone methides
    • Ralph, J.; Young, R. A. Stereochemical aspects of addition reactions involving lignin model quinone methides. J. Wood Chem. Technol. 1983, 3, 161-181.
    • (1983) J. Wood Chem. Technol. , vol.3 , pp. 161-181
    • Ralph, J.1    Young, R.A.2
  • 23
    • 0038833406 scopus 로고
    • On the mechanism of formation of noncyclic benzyl ethers during lignin biosynthesis. Pt. 4: The reactions of a β-O-4 type quinone methide with carboxylic acids in the presence of phenols. The formation and stability of benzyl esters between lignin and carbohydrates
    • Sipila, J.; Brunow, G. On the mechanism of formation of noncyclic benzyl ethers during lignin biosynthesis. Pt. 4: The reactions of a β-O-4 type quinone methide with carboxylic acids in the presence of phenols. The formation and stability of benzyl esters between lignin and carbohydrates. Holzforschung 1991, 45, 8-14.
    • (1991) Holzforschung , vol.45 , pp. 8-14
    • Sipila, J.1    Brunow, G.2
  • 24
    • 0010839733 scopus 로고    scopus 로고
    • Lignincarbohydrate model compounds. Formation of lignin-methyl arabinoside and lignin-methyl galactoside benzyl ethers via quinone methide intermediates
    • Toikka, M.; Sipila, J.; Teleman, A.; Brunow, G. Lignincarbohydrate model compounds. Formation of lignin-methyl arabinoside and lignin-methyl galactoside benzyl ethers via quinone methide intermediates. J. Chem. Soc., Perkin Trans. 1 1998, 3813-3818.
    • (1998) J. Chem. Soc., Perkin Trans. 1 , pp. 3813-3818
    • Toikka, M.1    Sipila, J.2    Teleman, A.3    Brunow, G.4
  • 25
    • 0010907074 scopus 로고    scopus 로고
    • Lignin-carbohydrate model compounds. Reactivity of methyl 3-O-(α-L-arabinofuranosyl)-β-D-xylopyranoside and methyl β-D-xylopyranoside towards a β-O-4-quinone methide
    • Toikka, M.; Brunow, G. Lignin-carbohydrate model compounds. Reactivity of methyl 3-O-(α-L-arabinofuranosyl)-β-D-xylopyranoside and methyl β-D-xylopyranoside towards a β-O-4-quinone methide. J. Chem. Soc., Perkin Trans. 1 1999, 1877-1883.
    • (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 1877-1883
    • Toikka, M.1    Brunow, G.2
  • 26
    • 0033064480 scopus 로고    scopus 로고
    • Modeling the feasibility of intramolecular dehydrodiferulate formation in grass walls
    • Hatfield, R. D.; Ralph, J. Modeling the feasibility of intramolecular dehydrodiferulate formation in grass walls. J. Sci. Food Agric. 1999, 79, 425-427.
    • (1999) J. Sci. Food Agric. , vol.79 , pp. 425-427
    • Hatfield, R.D.1    Ralph, J.2
  • 27
    • 0034695715 scopus 로고    scopus 로고
    • Regioselectivity in lignin biosynthesis. The influence of dimerization and cross-coupling
    • Syrjanen, K.; Brunow, G. Regioselectivity in lignin biosynthesis. The influence of dimerization and cross-coupling. J. Chem. Soc., Perkin Trans. 1 2000, 183-187.
    • (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 183-187
    • Syrjanen, K.1    Brunow, G.2
  • 28
    • 0001157046 scopus 로고
    • Mechanical constraints on lignin deposition during lignification
    • Donaldson, L. A. Mechanical constraints on lignin deposition during lignification. Wood Sci. Technol. 1994, 28, 111-118.
    • (1994) Wood Sci. Technol. , vol.28 , pp. 111-118
    • Donaldson, L.A.1
  • 29
    • 84949418325 scopus 로고
    • A biomimetic route to lignin model compounds via silver (I) oxide oxidation 1. Synthesis of dilignols and non-cyclic benzyl aryl ethers
    • Quideau, S.; Ralph, J. A biomimetic route to lignin model compounds via silver (I) oxide oxidation. 1. Synthesis of dilignols and non-cyclic benzyl aryl ethers. Holzforschung 1994, 48, 12- 22.
    • (1994) Holzforschung , vol.48 , pp. 12-22
    • Quideau, S.1    Ralph, J.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.