Die Bildung von Vanillin aus Fichtenlignin

Freudenberg, Karl; Lautsch, W.; Engler, Kurt

doi:10.1002/cber.19400730302

Cited by 100 publications

(29 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…As known for many years, lignin polymers may be related to the taxonomical status (Freudenberg et al, 1940;Creighton et al, 1944;Towers & Gibbs, 1953;Freudenberg, 1959). Using degradative techniques such as oxidation (Morrison, 1958), this fact has been looked for in the study of marine environments (Pocklington & McGregor, 1973;Hedges & Mann, 1976).…”

Section: Low-water Periodmentioning

confidence: 99%

Nature and distribution of phenolic compounds in water and sediments from Mediterranean deltaic and lagunal environments

1991

View full text Add to dashboard Cite

The nature and distribution of phenolic compounds were studied in suspended particles, sediment trap material and deposits in deltaic, marine and lagunal environments of the northwestern Mediterranean sea (Gulf of Lions).In deltaic environments (Rh6ne delta), the river flow controlled amounts of terrestrial run-off offshore as characterized by the abundance of phenolic compounds. A clear distinction appeared between surface water layers and deep layers. In the former, organic matter was less degraded and richer in phenolic acids than in the latter, where an abundant lithogenic phase was associated with degraded organic material rich in phenolic aldehydes, partly due to anthropogenic pollution. During the spate period, some compounds, such as phenolic aldehydes, were good indicators of hydrodynamic conditions, as they were carried down from the river bed to the prodelta. There, associated with the organo-mineral complex, they sank down to reach the benthic nepheloYd layer and flowed out offshore.Considering the chemical nature of phenolics, suspended material contained more labile phenolic compounds such as syringyl phenols. In contrast, vanillyl phenols, which are rather refractory components, were more concentrated in sediments.In the Lacaze-Duthiers Canyon (south of the Gulf of Lions), trapped material from the euphotic zone was relatively rich in phenols of marine origin. Similarities in phenolic composition appeared between trapped organic material in bottom layers of the Tt prodelta and of the side of the Canyon, reflecting a transfer of particles by advective currents from the shelf to the deep sea.In deposits containing relatively abundant phenols, humic acids were richer in phenols than fulvic acids.In lagunal environments, phenol contents in suspended material and deposits were relatively high, resulting from the abundant vegetal cover. Highest dissolved phenol contents occurred in water at the end of summer and early autumn on the edges of the Canet lagoon where abundant debris of decaying plants accumulated. Their nature depended essentially on the extent of phanerogam populations (Ruppia maritima, Phragmites australis), which are their major sources. In this area, fine deposits contained humic fractions richer in phenols than coarse sediments were. 90

show abstract

Section: Low-water Periodmentioning

confidence: 99%

Nature and distribution of phenolic compounds in water and sediments from Mediterranean deltaic and lagunal environments

1991

View full text Add to dashboard Cite

show abstract

“…The yieltl of vanillin obtainecl by nitrobenzene osiclation of spruce \voocl is about 25%, based 011 Iclason lignin (12,13). The percentage col1versions to lignin (va~~illin) shown in ' Table Vi are t l~~l s a fraction of the true conversions.…”

Section: Discussionmentioning

confidence: 98%

“…Furthermoi-e the percentage conversions of some phenylpropanoicl compounc1s to pungenin aglycone seem higher than would be expected by a mechanism involving exteilsive breakdown and rebuilding. Can The steps shown between caffeic acid and 3,4-dihydroxyacetophenone (R-CO-CI- 13) are speculative since the precursors sho\vn have not been tested yet; this schenie is to be regarded as a working hypothesis.…”

Section: Discussionmentioning

confidence: 98%

BIOSYNTHESIS OF PUNGENIN FROM C¹⁴-LABELLED COMPOUNDS BY COLORADO SPRUCE

Neish¹

1959

Can. J. Bot.

View full text Add to dashboard Cite

A number of ClLlabelled compounds were fed to detached leafy twigs of Colorado spruce (Picen pz~ngens Engelm.), and after a metabolic period of 24 hours the pungenin was isolated and the specified activities of the glucose lnqiety and the aglycone (3,4-dihydroxyacetophenone) were determined. 111 some Instances the aglycone was degraded further to determine the C1" in the methyl and carbonyl carbons separately.Caffeic acid and L-phenylalanine were the best precursors of the aglycone; cinnamic acid, 9-coumaric acid, phenyllactic acid, and shikimic acid were quite good. Sodium acetate was a poor precursor, and was converted to glucose more readily than to the aglycone. Compounds found to be very poor precursors include tyrosine, 3,4-dihydroxyphenylalanine, 3-hydroxytyramine, phenylacetic acid, mandelic acid, 9-hydrosyphenylpyr~~vic acid, 9-hydroxyphenyllactic acid, p-hydrosybenzoic acid, and protocatechuic acid. Cinnarnic acid-a-Cll gave 3,4-dihydroxyacetophenone labelled chiefly in the methyl group, while cinnamic acid-P-Cl", ~-phenylalanine-P-C1~~, 9-couinaric acid-P-Cl", and carfeic acid-P-C1.1 formed 3,4-dihydrosyacetophenone labelled mainly in the carbonyl carbon. I t appears that a phenylethanoid compound is formed by a process involving the loss of the terminal carbon of a phenylpropanoid co~npound.3,4-Dihydroxyacetophenone-carbonyl-CN was fed t o spruce twigs bearing new terminal growth; up t o 20% was converted to pungenin but most of it formed unidentified compounds. I t was a poor precursor of lignin, compared with cinnamic acid, and a poor precursor of glutamic acid, relative to acetate.'Manuscript

show abstract

“…O procedimento foi a reação original descrita por Freudenberg et al (1940) com modificações sugeridas por . No presente trabalho o método foi ligeiramente alterado.…”

Section: Oxidação Com Nitrobenzenounclassified

Composição fenólica de ligninas dioxano determinadas pela reação oxidativa com o nitrobenzeno

Fukushima

Hatfield

2003

Pesq. agropec. bras.

View full text Add to dashboard Cite

Resumo -A correta quantificação da concentração de lignina em plantas forrageiras, pelo método espectrofotométrico, pressupõe a existência de um padrão de referência. Um padrão de referência deve ter composição fenólica semelhante à da lignina da parede celular. O objetivo deste trabalho foi verificar se ligninas extraídas com solução ácida de dioxano para serem utilizadas como padrão de referên-cia, apresentariam variação na composição fenólica da mesma maneira que a lignina da parede celular. Amostras de parede celular de "bromegrass", milho e trevo-vermelho foram submetidas ao método para extração de ligninas com solução ácida de dioxano. A composição fenólica das ligninas foi analisada mediante oxidação alcalina pelo nitrobenzeno com posterior separação dos componentes monoméricos via HPLC. As ligninas extraídas confirmaram a existência de variação na composição fenólica da mesma maneira às ligninas intactas presentes na parede celular e de substancial presença de ácidos cinâmicos nas ligninas de gramíneas. No que diz respeito à composição fenólica, ligninas extraídas com solução ácida de dioxano podem ser consideradas potenciais padrões de referência paras as análises espectrofotométricas.Termos para indexação: parede celular, planta forrageira, ácido cinâmico, ácido ferúlico. Phenolic composition of dioxane lignins as determined by nitrobenzene oxidative reactionAbstract -The correct quantification of lignin concentration in forages through the spectrophotometric method presumes the existence of a reference standard. This standard must have a phenolic composition similar to the cell wall lignin. The objective of this work was to verify if the lignins extracted with acidic dioxane solution to be used as reference standard would present the same variation in the phenolic composition as it occurs in the cell wall lignin. Bromegrass, corn and red clover cell wall samples were submitted to the method for extraction of lignins with an acidic dioxane solution. The phenolic composition of the extracted lignins was analyzed by alkaline nitrobenzene oxidation followed by HPLC separation. Extracted lignins confirmed that they have phenolic composition variation the same way as do intact lignins present in the cell wall and that grass lignins showed substantial presence of cinnamic acids. Concerning to phenolic composition lignins extracted by acidic dioxane may potentially be used as reference standards in the spectrophotometric analysis.

show abstract

Die Bildung von Vanillin aus Fichtenlignin

Cited by 100 publications

References 4 publications

Nature and distribution of phenolic compounds in water and sediments from Mediterranean deltaic and lagunal environments

Nature and distribution of phenolic compounds in water and sediments from Mediterranean deltaic and lagunal environments

BIOSYNTHESIS OF PUNGENIN FROM C¹⁴-LABELLED COMPOUNDS BY COLORADO SPRUCE

Composição fenólica de ligninas dioxano determinadas pela reação oxidativa com o nitrobenzeno

Contact Info

Product

Resources

About

Die Bildung von Vanillin aus Fichtenlignin

Cited by 100 publications

References 4 publications

Nature and distribution of phenolic compounds in water and sediments from Mediterranean deltaic and lagunal environments

Nature and distribution of phenolic compounds in water and sediments from Mediterranean deltaic and lagunal environments

BIOSYNTHESIS OF PUNGENIN FROM C14-LABELLED COMPOUNDS BY COLORADO SPRUCE

Composição fenólica de ligninas dioxano determinadas pela reação oxidativa com o nitrobenzeno

Contact Info

Product

Resources

About

BIOSYNTHESIS OF PUNGENIN FROM C¹⁴-LABELLED COMPOUNDS BY COLORADO SPRUCE