Characterization of bioactive plant ellagitannins by chromatographic, spectroscopic and mass spectrometric methods
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Ellagitannins are widely distributed plant polyphenols showing potent anti-herbivore activities, but rather complex chemical structures. Here we show how ellagitannins with different structures can be efficiently characterized from plant extracts by utilizing the information obtained from four universal methods used for ellagitannin analysis: Sephadex LH-20 gel chromatography, high-performance liquid chromatography, ultraviolet spectroscopy, and mass spectrometry. We show that by combining the information obtained from the ellagitannins’ chromatographic elution order, specific shapes of the ultraviolet spectra, molecular masses and characteristic mass spectral fragmentations, it is possible to classify these polyphenols into different ellagitannin sub-groups, and even characterize the structures within the sub-groups. These findings aid in the fast screening of complex plant samples for their ellagitannin composition without having to isolate compounds for individual characterization.
KeywordsPolyphenol Hydrolyzable tannin Structure elucidation
The authors thank Maarit Karonen, Jaana Liimatainen, Matti Vihakas and Anu Tuo-minen for their comments on the earlier versions of the manuscript. Chris Yarnes and Kati Tuominen are acknowledged for their help with the purification of Quercus gambelii ellagitannins. This work was supported by the Academy of Finland (Grant No 119659 and 258992 to JPS) and the Kone Foundation (JM).
- Doig AJ, Williams DH, Oelrichs PB, Baczynskyj L (1990) Isolation and structure elucidation of punicalagin, a toxic hydrolysable tannin, from Terminalia oblongata. J Chem Soc Perkin Trans 1:2317–2321Google Scholar
- Hagerman AE (2012) The tannin handbook. http://www.users.muohio.edu/hagermae/. Accessed 4 December 2012
- Pfundstein B, El Desouky SK, Hull WE, Haubner R, Erben G, Owen R (2010) Polyphenolic compounds in the fruits of Egyptian medicinal plants (Terminalia bellerica, Terminalia chebula and Terminalia horrida): characterization, quantitation and determination of antioxidant capacities. Phytochemistry 71:1132–1148PubMedCrossRefGoogle Scholar
- Silva O, Gomes ET, Wolfender J-L, Marston A, Hostettmann K (2000) Application of high performance liquid chromatography coupled with ultraviolet spectroscopy and electrospray mass spectrometry to the characterisation of ellagitannins from Terminalia macroptera roots. Pharm Res 17:1396–1401PubMedCrossRefGoogle Scholar