Taninos o polifenoles vegetales

Scientia Et Technica 01/2007;
Source: DOAJ

ABSTRACT El término tanino se acuñó históricamente por el uso empírico que se daba a algunos extractos vegetales para el proceso de tanaje o conversión de las pieles de animales en cuero desde hace más de cien años. El desarrollo de las modernas técnicas instrumentales para la elucidación estructural de sustancias orgánicas, permitió el inicio científico en el área de polifenoles vegetales, término sugerido por el doctor Edwin Haslam en lugar de taninos. En esta revisión se discuten algunos hechos históricos, definiciones, técnicas de aislamiento y elucidación estructural, clasificación y aplicaciones de estos compuestos, desde la curtiembre hasta la industria alimenticia.

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    ABSTRACT: The tanoak (Lithocarpus densiflorus) acorn was a staple food in the Native American diet and is still used in traditional dishes. Acorns from the genus Quercus have been shown to contain a large range of hydrolyzable tannins. However, neither hydrolyzable nor condensed tannins have been characterized in tanoak acorns. The aim of this study was to identify the full range of hydrolyzable and condensed tannins in extracts of tanoak acorns using liquid chromatography/electrospray ionization-mass spectrometry/mass spectrometry. Condensed tannins were identified as B type oligomers of (epi)-catechin (procyanidins) with a degree of polymerization up to six. Oligomers up to and including tetramers were identified by UV spectra and MS detection whereas pentamers and hexamers were detected only by MS. The total concentration of condensed tannins was 464 mg/100 g acorn pericarp. The concentration of propocyanidin monomers, dimers, trimers, and tetramers in acorn pericarp (mg/100 g acorn pericarp) were 95 +/- 10.9, 148 +/- 35.0, 90 +/- 17.9, and 131 +/- 1.9, respectively. No procyanidins were found in the acorn cotyledon tissue. A total of 22 hydrolyzable tannins were identified in methanolic extracts of acorn cotyledon tissue. Gallic acid derivatives predominated and included galloylated esters of glucose, hexahydrodiphenoyl esters of glucose, and methylated gallates. Galloylated esters of glucose were present as isomers of galloyl glucose, digalloyl glucose, and trigalloyl glucose. Mass spectral fragmentation patterns indicate the presence of one gallic acid-galloyl glucose isomer and two gallic acid-digalloyl-glucose isomers. No isomers of tetragalloyl glucose and pentagalloyl glucose were identified. Ellagic acid and ellagic acid pentoside were also identified.
    Journal of Agricultural and Food Chemistry 11/2006; 54(20):7686-91. · 3.11 Impact Factor
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    ABSTRACT: The pantropical plant family Melastomataceae produces characteristic hydrolyzable tannin oligomers. The latter in this family are distinguished from those in other plant families by the fact that the oligomers from dimers to tetramers are composed of two different alternating monomeric units: casuarictin and pterocaryanin C. These oligomers are metabolites that are produced by intermolecular C-O oxidative coupling between the monomers (or their desgalloyl-or des-hexahydroxydiphenoyl derivatives) forming a valoneoyl group as the link between monomers. The chemotaxonomically significant oligomerization pattern of melastomataceous plants provided helpful suggestions for determining the structures of new oligomers (nobotanins Q-T and melastoflorins A-D) isolated from Monochaetum multiflorum, which belongs to this family. Melastoflorins A-D were characterized as pentamers, which are the largest hydrolyzable tannins composed of different monomeric units.
    Phytochemistry 10/2005; 66(17):1972-83. · 3.35 Impact Factor
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    ABSTRACT: A speculative scheme for procyanidin (condensed tannin) biosynthesis involving multienzyme complexes is presented in which the stereochemistry at C-3 and C-4 of (+)-dihydroquercetin is maintained in (+)-catechin and its oligomeric products. This is in contrast to Haslam's speculation involving a symmetrical flav-3-en-3-ol intermediate, which requires the re-introduction of the stereochemistry at the terminal reduction steps. In the proposed scheme, the origin of the 2,3-cis stereochemistry of (−)-epicatechin from (+)-dihydroquercetin would require an epimerase, in addition to two reductases and a condensing enzyme neeeded for (+)-catechin stereochemistry.
    Phytochemistry 01/1983; 22(12):2643-2646. · 3.35 Impact Factor

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