Research related to Chemistry & Biology

Methods and research techniques have been studied and developed to look specifically at Sainfoin polyphenols which include tannins and flavonoids. As anticipated there were significant differences between Sainfoin types and this will lead to further development of Sainfoin plant breeding.

Scientific Articles/Findings

Poster Presentations

Bioactive Tannins in Forage Legumes: Myths, Ignorance and Aspirations.

Prof. Irene Mueller Harvey - University of Reading

Current Research on the Potential of Bioactive Legumes for Animal Nutrition and Sustainability

I. Mueller-Harvey - University of Reading

First de-novo transcriptome assembly for gene identification, analysis and annotation, transcriptional level study, and molecular marker discovery in Onobrychis viciifolia

NIAB & IBERS - Marina Mora-Ortiz, Lydia Smith, Tom Wood, Leif Skot

Towards Developing Plants For Production Of Useful Tannins

University of Reading, NIAB & Rothamsted Research - I. Mueller-Harvey, E. Stringano, L. Falchero, C. Hayot-Carbonero, L. Smith, S. Hanley, I. Shield, A. Karp

Abstracts of Published Papers

1H-13C HSQC NMR spectroscopy for estimating procyanidin/prodelphinidin and cis/trans flavanol ratios of condensed tannin fractions: correlation with thiolysis. J. Agric. Food Chem. 2015, 63, 1967−1973

Zeller, W.E., Ramsay, A., Ropiak, H.M., Fryganas, C., Mueller-Harvey, I., Brown, R.H., Drake, C., Grabber, J.H.

Acetone enhances the direct analysis of procyanidin- and prodelphinidin-based condensed tannins in Lotus species by the butanol-HCl-iron assay. J. Agric. Food Chem. 2013, 61, 2669-2678.

Grabber J., Zeller, W.E., Mueller-Harvey, I.

Benefits of condensed tannins in forage legumes fed to ruminants: importance of structure, concentration and diet composition.

Prof. Irene Mueller-Harvey et al - University of Reading

Protein precipitation behavior of condensed tannins from Lotus pedunculatus and Trifolium repens with different mean degrees of polymerization. J. Agric. Food Chem. 2015, 63, 1160−1168.

Zeller, W.E., Sullivan, M.L., Mueller-Harvey, I., Grabber, J.H., Ramsay, A., Drake, C., Brown, R.H.

Rapid Qualitative and Quantitative Analyses of Proanthocyanidin Oligomers and Polymers by UPLC-MS/MS

University of Turku - Marica T. Engström, Maija Pälijärvi, Christos Fryganas, John H. Grabber, Irene Mueller-Harvey, and Juha-Pekka Salminen

Published Papers

Benefits of condensed tannins in forage legumes fed to ruminants: importance 1 of structure, 2 concentration and diet composition

Irene Mueller-Harvey et al - University of Reading

Benefits of Condensed Tannins in Forage Legumes Fed to Ruminants: Importance of Structure, Concentration, and Diet Composition

Irene Mueller-Harvey, Giuseppe Bee, Frigga Dohme-Meier, Hervé Hoste, Maarit Karonen, Roland Kölliker, Andreas Lüscher, Vincent Niderkorn, Wilbert F. Pellikaan, Juha-Pekka Salminen, Leif Skøt, Lydia M.J. Smith, Stig M. Thamsborg, Paul Totterdell, Ian Wilkinson, Andrew R. Williams, Blasius N. Azuhnwi, Nicolas Baert, Anja Grosse Brinkhaus, Giuseppe Copani, Olivier Desrues.

Characterization of Condensed Tannins from Purple Prairie Clover (Dalea purpurea Vent.) Conserved as either Freeze-Dried Forage, Sun-Cured Hay or Silage

Kai Peng 1,2,3, Qianqian Huang 4, Zhongjun Xu 2, Tim A. McAllister 2, Surya Acharya 2, Irene Mueller-Harvey 5, Christopher Drake 5, Junming Cao 1, Yanhua Huang 1, Yuping Sun 1, Shunxi Wang 3 and Yuxi Wang 2,*

Facile Purification of Milligram to Gram Quantities of Condensed Tannins According to Mean Degree of Polymerization and Flavan-3-ol Subunit Composition

Prof. Irene Mueller-Harvey - University of Reading

Forty-five years in the rumen; aroma, discovery, and fun

Waghorn, G.

Identification of Structural Features of Condensed Tannins That Affect Protein Aggregation

Honorata M. Ropiak, Peter Lachmann, Aina Ramsay, Rebecca J. Green, Irene Mueller-Harvey

Supplementary Material - Facile Purification of Milligram to Gram Quantities of Condensed Tannins According to Mean Degree of Polymerization and Flavan-3-ol Subunit Composition

Relevant and Pre-existing Material

Grabber Reaction - HCl, Butanol, Acetone reaction – Outline with videos

Irene Mueller-Harvey, University of Reading

In Situ Thiolysis Procedure – Outline with videos

Irene Mueller-Harvey, University of Reading

Wide Column fractionation Procedure - Outline with Videos

Irene Mueller-Harvey, University of Reading

Results from The Healthy Hay Project

Acylated flavonol glycosides from the forage legume, Onobrychis viciifolia (sainfoin). Phytochemistry, 2011, 72, 423-429.

Veitch N.C., Regos I., Kite . G.C., Treutter D.

Binding of pentagalloyl glucose to two globular proteins occurs via multiple surface sites

University of Reading - Dobreva, M.A., Frazier, R.A., Mueller-Harvey, I., Clifton, L.A., Gea, A., Green, R.J. Biomacromolecules 2011, 12, 710-715.

Binding of pentagalloyl glucose to two globular proteins occurs via multiple surface sites. Biomacromolecules 2011, 12, 710-715.

Dobreva, M.A., Frazier, R.A., Mueller-Harvey, I., Clifton, L.A., Gea A., Green, R.J.

Biosynthesis of flavonoids in Sainfoin

Technical University of Vienna - Asma F. Ahmad, Jana Thill, Ionela Regos, Christine Hayot, Heidi Halbwirth, Lydia Smith, Dieter Treutter, Karl Stich

Characterisation of sainfoin (Onobrychis viciifolia) condensed tannins by MALDI-TOF mass spectrometry

Reading University - Elisabetta Stringano, An Gea, Rainer K. Cramer, Wayne Hayes & Irene Mueller-Harvey

Characterisation of Sainfoin tannins by degradation studies chromatography and calorimetry

Reading University - An Gea, Elisabetta Stringano, Marina A. Dobreva, Trevor Gibson, Richard A. Frazier, Rebecca J. Green & Irene Mueller- Harvey

Deciphering the complexity of sainfoin (Onobrychis viciifolia) proanthocyanidins by MALDI-TOF mass spectrometry with a judicious choice of isotope patterns and matrices. Anal. Chem. 2011, 83, 4147-4153

Stringano, E., Cramer, R., Hayes, W., Smith, C., Gibson, T., Mueller-Harvey, I.

Deciphering the complexity of sainfoin (Onobrychis viciifolia) proanthocyanidins by MALDI-TOF mass spectrometry with a judicious choice of isotope patterns and matrices. Analytical Chemistry 2011, 83, 4147-4153.

Reading University - Stringano E., Cramer R., Hayes W., Smith, C., Gibson T., Mueller-Harvey I.

Effect of different conservation methods and maturity stages on peroxidase activity in sainfoin (Onobrychis viciifolia)

Technical University of Vienna - Asma Faqir Ahmad, Katerina Theodoridou, Heidi Halbwirth, Jocelyne Aufrère, Karl Stich

Effect of wilting, silage additive, PEG treatment and tannin content on the distribution of N between different fractions after ensiling of three different sainfoin (Onobrychis viciifolia) varieties. Grass and Forage Science, 65, 175-184.

Lorenz, M.M., Eriksson, T., Uden, P. 2010

Exploring variation in proanthocyanidin composition and content of sainfoin (Onobrychis viciifolia). J. Sci. Food Agric. 2013, 93, 2102-2109.

Azuhnwi, B.N., Boller, B., Dohme-Meier, F., Hess, H.D., Kreuzer, M., Stringano, E., Mueller-Harvey, I.

Flavonoids and their formation in different sainfoin varieties (Onobrychis viciifolia)

Technical University of Vienna & Technische Universitat, Munchen - Jana Thill, Ionela Regos, Christine Hayot, Ilya Gadjev, Karin Schlangen, Heidi Halbwirth, Dieter Treutter, Lydia Smith, Karl Stich

Identification and quantification of phenolic compounds from the forage legume sainfoin (Onobrychis viciifolia). J. Agric. Food Chem. 2009, 57, 5843-5852.

Regos I., Urbanella A., Treutter D.

In situ analysis and structural elucidation of sainfoin (Onobrychis viciifolia) tannins for high throughput germplasm screening. J. Agric. Food Chem. 2011, 59, 495-503.

Gea, A., Stringano, E., Brown, R.H., Mueller-Harvey, I.

In vitro protein degradation of 38 sainfoin accessions and its relationship to tannin content by different assays. J. Agric. Food Chem. 60, 5071−5075

Lorenz, M.M., Hayot Carbonero, C., Smith, L., Udén, P., 2012

Influence of formic acid and dry matter on protein degradation in the tanniniferous legume sainfoin. Animal Feed Sci Technol. 164, 217–224.

Lorenz, M.M., Udén, P., 2011

Investigation of sainfoin (Onobrychis viciifolia) cultivar differences on nitrogen balance and fecal egg count in artificially infected lambs. J. Anim. Sci. 2013, 91, 2342-2354.

Azuhnwi, BN, Hertzberg, H, Arrigo, Y, Gutzwiller, A, Hess, HD, Mueller-Harvey, I., Torgerson, P, Kreuzer, M, Dohme-Meier, F

Morphology, tannin concentration and forage value of 15 Swiss accessions of sainfoin (Onobrychis viciifolia Scop) as influenced by harvest time and cultivation site. Grass Forage Sci. 2011, 66, 474-487.

Azuhnwi, B.N., Boller, B., Martens, M., Dohme-Meier, F., Ampuero S., Gunter, S., Kreuzer, M., Hess, H.D.,

Near Infrared Spectroscopy (NIRS) for Screening Sainfoin Germplasm

Reading University - Martin-Lorenzo M, Hayot C, Stringano E, Falco-Sales L, Smith L, Barnes R, Oliver J, Brown R H, Mueller-Harvey I

Optimization of a high-performance liquid chromatography method for the analysis of complex polyphenol mixtures and application for sainfoin extracts (Onobrychis viciifolia). J. Chromatogr A 1217, 6169-77.

Regos I., Treutter D. 2010

Phylogenetic characterisation of Onobrychis species with special focus on the forage crop Onobrychis viciifolia Scop.

Reading University & NIAB - Hayot Carbonero Christine, Carbonero Franck, Smith Lydia, Brown Terence

Polyphenol metabolism provides a screening tool for beneficial effects of Onobrychis viciifolia (sainfoin). Phytochemistry. 82, 67-80

Thill J., Regos I., Farag M.A., Ahmad A.F., Kusek J., Castro A., Schlangen K., Carbonero C.H., Gadjey I.Z., Smith L.M., Halbwirth H., Treutter D., Stich K. 2012.

Proanthocyanidin diversity in the EU ‘HealthyHay’ sainfoin (Onobrychis viciifolia) germplasm collection

University of Reading and NIAB - Stringano, E., Hayot Carbonero, C, Smith, L, Brown, RH, Mueller-Harvey, I. Phytochemistry (doi: 10.1016/j.phytochem.2012.01.013)

Proanthocyanidin diversity in the EU ‘HealthyHay’ sainfoin (Onobrychis viciifolia) germplasm collection Phytochemistry 2012, 77, 197-208.

Stringano, E., Hayot Carbonero, C., Smith, L.M.J., Brown, R.H., Mueller-Harvey, I.

Ruminal dry matter and crude protein degradation kinetics of five sainfoin (Onobrychis viciifolia Scop) accessions differing in condensed tannin content and obtained from different harvest. Anim. Feed Sci. Tech. 2012, 177, 135-143.

Simple solution for a complex problem: proanthocyanidins, galloyl glucoses and ellagitannins fit on a single calibration curve in high performance-gel permeation chromatography.

University of Reading and University of Turku, Finland - Stringano, E., Gea, A., Salminen, J-P, Mueller-Harvey, I. J. Chromatogr. A 2011, 1218, 7804-7812.

Simple solution for a complex problem: proanthocyanidins, galloyl glucoses and ellagitannins fit on a single calibration curve in high performance-gel permeation chromatography. J. Chromatogr. A 2011, 1218, 7804-7812.

Stringano, E., Gea, A., Salminen, J-P., Mueller-Harvey, I.

Size and molecular flexibility affect the binding of ellagitannins to bovine serum albumin. J. Agric. Food Chem. 2014, 62, 9186-9194.

Dobreva M.A., Green R.J., Mueller-Harvey I., Salminen J-P., Howlin B.J., Frazier R.A.

Tannins Explained

Reading University - Gea, A., Stringano, E., Brown, R.H., Mueller‐Harvey, I. In situ analysis and structural elucidation of sainfoin (Onobrychis viciifolia) tannins for high throughput germplasm screening. J. Agric. Food Chem. 2011, 59, 495‐503.

The effects of condensed tannins against cattle nematodes (oral presentation). 23rd International Conference of the World Association for the Advancement of Veterinary Parasitology Congress, 21 to 25 August 2011, Buenos Aires, Argentina.

Swedish University of Agricultural Sciences, University of Copenhagen, University of Reading - Novobilský, A., Thamsborg, S.M., Mueller-Harvey, I.

Towards Developing Plants for Production of Useful Tannins

Univerity of Reading - I. Mueller-Harvey, E. Stringano, L. Falchero, C. Hayot-Carbonero, L. Smith, S. Hanley, I. Shield, A. Karp