Arylpropane-1,3-diols in lignins from normal and CAD-deficient pines

Organic Letters

Volumn 1, Issue 2, 1999, Pages 323-326

  Ralph, John ^a,b   Kim, Hoon ^a,b   Peng, Junpeng ^a   Lu, Fachuang ^a,b  

^a U S DAIRY FORAGE RESEARCH CENTER   (United States)

^b UNIVERSITY OF WISCONSIN MADISON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DEHYDROGENASE; CINNAMYL ALCOHOL DEHYDROGENASE; LIGNIN; PROPANOL;

ARTICLE; CHEMISTRY; GENETICS; MUTATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TREE;

ALCOHOL OXIDOREDUCTASES; LIGNIN; MAGNETIC RESONANCE SPECTROSCOPY; MUTATION; PROPANOLS; TREES;

EID: 0033614870     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol9906559     Document Type: Article

References (24)

1. Ralph, J.; MacKay, J. J.; Hatfield, R. D.; O'Malley, D. M.; Whetten, R. W.; Sederoff, R. R. Science 1997, 277, 235-239.
2. Ralph, J.; Hatfield, R. D.; Piquemal, J.; Yahiaoui, N.; Pean, M.; Lapierre, C.; Boudet, A.-M. Proc. Nat. Acad. Sci. U.S.A. 1998, 95, 12803-12808.
3. Boudet, A.-M. Trends Plant Sci. 1998, 3, 67-71.
4. MacKay, J. J.; O'Malley, D. M.; Presnell, T.; Booker, F. L.; Campbell, M. M.; Whetten, R. W.; Sederoff, R. R. Proc. Natl. Acad. Sci. U.S.A. 1997, 94, 8255-8260.
5. (a) Freudenberg, K.; Neish, A. C. Constitution and Biosynthesis of Lignin; Springer-Verlag: Berlin-Heidelberg-New York, 1968.
6. (b) Harkin, J. M. In Oxidative Coupling of Phenols; Taylor, W. I., Battersby, A. R., Eds.; Marcel Dekker: New York, 1967; pp 243-321.
7. Sederoff, R. R.; MacKay, J. J.; Ralph, J.; Hatfield, R. D. Curr. Opin. Plant Biol. 1999, 2, 145-152, and references therein.
8. 1 (8) Lignin is the term used for the phenylpropanoid polymer in the cell walls of normal plants and will be used here although there remain issues regarding the biochemical and functional roles of "nontraditional" lignins in mutants and transgenics (see refs 6 and 11).
9. Ralph, J.; Marita, J. M.; Ralph, R. A.; Hatfield, R. D.; Lu, F.; Ede, R. M.; Peng, J.; Quideau, S.; Helm, R. F.; Grabber, J. H.; Kim, H.; MacKay, J. J.; Sederoff, R. R.; Chapple, C.; Boudet, A. M. In Progress in Lignocellulosics Characterization; Argyropoulos, D. S., Rials, T., Eds.; TAPPI Press: Atlanta, GA, 1999; in press.
10. (a) Lundquist, K.; Stern, K. Nordic Pulp Paper Res. J. 1989, 210-213.
11. (b) Fukagawa, N.; Meshitsuka, G.; Ishizu, A. J. Wood Chem. Technol. 1991, 11, 373-396.
12. (c) Brunow, G.; Ämmålahti, E.; Niemi, T.; Sipilä. J.; Simola, L. K.; Kilpeläinen, I. Phytochem. 1998, 47, 1495-1500.
13. (a) Gang, D. R.; Fujita, M.; Davin, L. D.; Lewis, N. G. In Lignin and Lignan Biosynthesis; Lewis, N. G., Sarkanen, S., Eds.; American Chemical Society: Washington, DC, 1998; ACS Symposium Series 697, pp 389-421.
14. (b) Lewis, N. G.; Davin, L. B.; Sarkanen, S., ref 11a, pp 1-27.
15. (c) Lewis, N. G. In Abstracts of Papers, 215th National Meeting of the American Chemical Society, Dallas, TX; American Chemical Society: Washington, DC, 1998; Vol. 1, p Cell-09.
16. 1 For this study, the lignins were acetylated, extracted into EtOAc, and washed with 6 mM EDTA to improve NMR relaxation properties (cf. ref 2).
17. H-73.2/5.85 (α), 35.8/ 2.18 (β), 61.2/4.08 (γ). Unambiguously assigned full NMR data will be deposited in the Internet-accessible NMR Database of Lignin and Cell Wall Model Compounds (Ralph, S. A.; Ralph, J.; Landucci, W. L.; Landucci, L. L.; http://www.dfrc.ars.usda.gov/software.html 1999, entry #3029) Various APD-containing products have also been isolated from radical coupling reactions of DHCA, as will be described elsewhere.
18. (a) Schleucher, J.; Schwendinger, M.; Sattler, M.; Schmidt, P.; Schedletzky, O.; Glaser, S. J.; Sorensen, O. W.; Griesinger, C. J. Biomol. NMR 1994, 4, 301-306.
19. (b) Palmer, A. G.; Cavanagh, J.; Wright, P. E.; Rance, M. J. Magn. Reson. Ser. A 1991, 93, 151-170.
20. Zanarotti, A. Tetrahedron Lett. 1982, 23, 3815-18.
21. C (assignment): 3.31/37.5 (β), 4.41/ 60.4 (γ), 196.3 (α).
22. (a) Lu, F.; Ralph, J. J. Agric. Food Chem. 1997, 45, 2590-2592.
23. (b) Lu, F.; Ralph, J. J. Agric. Food Chem. 1997, 45, 4655-4660.
24. (c) Lu, F.; Ralph, J. In Lignin and Lignan Biosynthesis; Lewis, N. G., Sarkanen, S., Eds.; American Chemical Society: Washington, DC, 1998; pp 294-322