Agenda. Wood Chemistry. Stilbenes Biological Significance. Stilbenes. PSE 406/Chem E 470. Stilbenes. Flavonoids
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1 Agenda PSE 06/Chem E 70 Lecture 1,, and Condensed Tannins PSE 06: Lecture 1 1 PSE 06: Lecture 1 Biological Significance Phenolic extractive found in the heartwood of softwoods» Particularly prevalent in Pinus Cause light induced darkening in wood Most often aromatic rings: occasionally more Presence of double bond linkage» Naturally present most often in trans form H -Hydroxystilbene H Pinosylvin PSE 06: Lecture 1 Glu H Piceid Improves decay resistance» Reduces fungal activity. Improves Insect resistance» in leaves reduce insect feeding. Reduces animal damage» Pinosylvin containing leaves have been shown to suffer less damage from Snowshoe hare consumption. PSE 06: Lecture 1 1 1
2 Pulp and Paper Problems Effluent issues» Chlorinated stilbene derivatives cause problems in effluents Fish are affected at low levels Pulping problems» Discovered in 1800 s, that certain trees (pine and others) cannot be pulped by the acid sulfite process. Culprit turned out to be stilbenes which cause lignin crosslinking reactions (condensation). Referred to as the most ubiquitous monomeric natural product. Serve many roles in plants:» Protection» Coloration» ther unique roles. H Catechin (Western Hemlock) PSE 06: Lecture 1 PSE 06: Lecture 1 6 General Structural Information Classifications Polyphenolic compounds found in softwoods and hardwoods Composed of diphenylpropane units C 6 -C -C 6 Eight structural classifications differ through substitution on the rings» Typically or CH groups» Typical to have on positions: and 7, and Are also present as gylcosides A C ' B ' 6' ' ' Flavones Catechins Flavonols Leucoanthocyanidins Flavanoes Chalcones Flavanonols Aurones PSE 06: Lecture 1 7 PSE 06: Lecture 1 8
3 Representative Structures of Flavonoid Classes Biological Signifcance H Chrysin H H Pinobanskin H H Taxifolin (Douglas Fir) H H Catechin (Western Hemlock) H H Pinocembrin Quercitin (ak) H Not all flavonoids have same function in plants Anti-fungal Insects» some feeding deterrents/some stimulants Antioxidant Color: bright colors in plants PSE 06: Lecture 1 9 PSE 06: Lecture 1 10 Location in Tree Medicinal Uses Found in the heartwood of most tress» Referred to as most ubiquitous monomeric natural product» ften responsible for coloration Found in lesser amounts in the sapwood Are found in large amounts in bark Roots» Certain flavonoids play role in tree s interaction with beneficial organisms Leaves: Green tea can contain up to 0% flavonoids Flowers: Color is often due to flavonoids Higher flavonoid content in diet reduces chance of:» Heart Disease Strengthen capillaries Dilates blood vessels» Stroke» Cancer: all types reduced Finnish study = ½ rate of cancer PSE 06: Lecture 1 11 PSE 06: Lecture 1 1
4 Pulp and Paper Problems (flavanonols- taxifolin) also cause problems in sulfite pulping» Flavanonols are oxidized by bisulfite to flavonols producing thiosulfite Thiosulfite causes lignin condensation reactions H Taxifolin H HS - + S - Quercitin H Condensed tannins are formed through the polymerization of flavan--ol (catechin) and flavan,-diols (leucoanthocyanidins)» In tree, polymerization through acidic enzymatic non-oxidative coupling» -0 units Typically -8» Linkages can be through a variety of sites Flavan-,-diols (Leucoanthocyanidins) Flavan--ols (Catechins) PSE 06: Lecture 1 1 PSE 06: Lecture 1 1 Location in the Tree Catechins (flavan--ols) Leucoanthocyanidins (flavan-,-diols) H H H H Typical Structure of PSE 06: Lecture 1 1 Western hemlock» Bark: 18% tannins» Wood: % tannins Quebracho» In wood, tannins found in heartwood» Majority (80%) located in vessel lumina» Tannins deposit in dead cell starting at CML and ending in secondary wall PSE 06: Lecture 1 16
5 Biological Significance Uses of Condensed Tannins Protection of plants against insects/animals» Bad Taste/Astringency (bitter taste)» Animals: tannins reduce digestion of food Toxic to bacteria Pine calluses: created by fungal invasion» Tree forms calluses as protective tissue» Calluses contain high levels of tannins (Chinese 0-80% Wattle & Quebracho Leather tanning: 10,000+ year old industry» Vegetable tannins & chrome» Tannins interact with proteins in hides Adhesives Biocides Chelation: micronutrient fertilizers Mineral flotation PSE 06: Lecture 1 17 PSE 06: Lecture 1 18
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