Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2008 Dec 4;13(12):2986-97.
doi: 10.3390/molecules13122986.

HPLC, NMR and MALDI-TOF MS analysis of condensed tannins from Lithocarpus glaber leaves with potent free radical scavenging activity

Liang Liang Zhang  1 , Yi Ming Lin
Affiliations

HPLC, NMR and MALDI-TOF MS analysis of condensed tannins from Lithocarpus glaber leaves with potent free radical scavenging activity

Liang Liang Zhang et al. Molecules. .

Abstract

Using acid-catalyzed degradation in the presence of cysteamine, the condensed tannins from Lithocarpus glaber leaves were characterized, following thiolysis, by means of reversed-phase HPLC, 13C-NMR and matrix-assisted laser desorption/ionization time of flight mass spectrometry (MALDI-TOF MS) analyses. The thiolysis reaction products showed the presence of the procyanidin (PC) and prodelphinidin (PD) structures. The 13C-NMR spectrum revealed that the condensed tannins were comprised of PD (72.4%) and PC (27.6%), and with a greater content of cis configuration rather than the trans configuration of C2-C3. The MALDI-TOF MS analysis proved the presence of PD units, and the maximum degree of polymerization (DP) was an undecamer. The antioxidant activity of condensed tannins from L. glaber leaves was evaluated by using a free radical scavenging activity assay.

PubMed Disclaimer

Figures

Figure 1
Figure 1
Structures of proanthocyanidins polymer (a), monomeric flavan-3-ol (b), and their aminomethylthio derivatives (c).
Figure 2
Figure 2
Reversed-phase HPLC chromatograms of condensed tannins from L. glaber leaves degraded in the presence of cysteamine; EC, (-)-epicatechin; Cat, (+)-catechin; EGC, (-)-epigallocatechin; GC, (-)-gallocatechin; Cya-Cat, 4β-(2-aminoethylthio)catechin; Cya-GC, 4β-(2-aminoethylthio) gallocatechin.
Figure 3
Figure 3
13C-NMR (150 MHz) spectrum of condensed tannins from L. glaber leaves in acetone-d6/D2O; t, terminal unit; m, middle unit; e, extension unit; PC, procyanidin; PD, prodelphinidin.
Figure 4
Figure 4
MALDI-TOF MS of condensed tannins from L. glaber leaves.
Figure 5
Figure 5
Percentage of free radical scavenging activity of condensed tannins, BHA and ascorbic acid. ●, condensed tannins of L. glaber; ○, BHA; ▼, ascorbic acid.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Scalbert A., Monties B., Janin G. Tannins in wood: comparison of different estimation methods. J. Agric. Food Chem. 1989;37:1324–1329. doi: 10.1021/jf00089a026. - DOI
    1. Kennedy J.A., Taylor A.W. Analysis of proanthocyanidins by high-performance gel permeation chromatography. J. Chromatogr. A. 2003;995:99–107. doi: 10.1016/S0021-9673(03)00420-5. - DOI - PubMed
    1. Tanner G.J., Francki K.T., Abrahams S., Watson J.M., Larkin P.J., Ashton A.R. Proanthocyanidin biosynthesis in plants: purification of legume leucoanthocyanidin reductase and molecular cloning of its cDNA. J. Biol. Chem. 2003;278:31647–31656. - PubMed
    1. Haslam E. Cambridge University Press; Cambridge, UK: 1989. Plant Polyphenols: Vegetable Tannins Revisited.
    1. Svedstrom U., Vuorela H., Kostiainen R., Huovinen K., Laakso I., Hiltunen R. High-performance liquid chromatographic determination of oligomeric procyanidins from dimers up to the hexamer in hawthorn. J. Chromatogr. A. 2002;968:53–60. doi: 10.1016/S0021-9673(02)01000-2. - DOI - PubMed

Publication types

MeSH terms

LinkOut - more resources