Hydroxystilbene Glucosides Are Incorporated into Norway Spruce Bark Lignin
Journal Article
·
· Plant Physiology (Bethesda)
- Instituto de Recursos Naturales y Agrobiología de Sevilla (IRNAS), CSIC, Avda. Reina Mercedes, 10, 41012-Seville, Spain
- Centro de Estudos Florestais, Instituto Superior de Agronomia, Universidade de Lisboa, Tapada da Ajuda, 1349-017 Lisboa, Portugal
- Department of Energy Great Lakes Bioenergy Research Center, the Wisconsin Energy Institute, University of Wisconsin-Madison, Madison, Wisconsin 53726, Department of Biochemistry, University of Wisconsin-Madison, Madison, Wisconsin 53706
Recent investigations have revealed that, in addition to monolignols, some phenolic compounds derived from the flavonoid and hydroxystilbene biosynthetic pathways can also function as true lignin monomers in some plants. In this study, we found that the hydroxystilbene glucosides isorhapontin (isorhapontigenin-$$O$$-glucoside) and, at lower levels, astringin (piceatannol-$$O$$-glucoside) and piceid (resveratrol-$$O$$-glucoside), are incorporated into the lignin polymer in Norway spruce (Picea abies) bark. The corresponding aglycones isorhapontigenin, piceatannol, and resveratrol, along with glucose, were released by derivatization followed by reductive cleavage (DFRC), a chemical degradative method that cleaves $$β$$-ether bonds in lignin, indicating that the hydroxystilbene glucosides are (partially) incorporated into the lignin structure through $$β$$-ether bonds. Further, Two-dimensional NMR analysis confirmed the occurrence of hydroxystilbene glucosides in this lignin, and provided additional information regarding their modes of incorporation into the polymer. The hydroxystilbene glucosides, particularly isorhapontin and astringin, can therefore be considered genuine lignin monomers that participate in coupling and cross-coupling reactions during lignification in Norway spruce bark.
- Research Organization:
- Univ. of Wisconsin, Madison, WI (United States)
- Sponsoring Organization:
- USDOE Office of Science (SC)
- Grant/Contract Number:
- SC0018409
- OSTI ID:
- 1508886
- Alternate ID(s):
- OSTI ID: 1612977
- Journal Information:
- Plant Physiology (Bethesda), Journal Name: Plant Physiology (Bethesda) Journal Issue: 3 Vol. 180; ISSN 0032-0889
- Publisher:
- American Society of Plant BiologistsCopyright Statement
- Country of Publication:
- United States
- Language:
- English
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