Direct proof of a homogeneous polyflavan-3-ol structure for polymeric proanthocyanidins

Czochanska, Z.; Foo, Lai Yeap; Newman, Roger H.; Porter, Lawrence J.; Thomas, Wayne A.; Jones, William T.

doi:10.1039/c39790000375

Cited by 49 publications

(23 citation statements)

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“…In addition, a NMR database exists listing 1 H and 13 C NMR chemical shifts for CTs (up to tetramers) reported in the literature through 2015 (Zeller and Schatz, 2017). Solution-state 13 C NMR spectroscopy has long been and remains a valuable tool for structural determination of purified CT samples and has been used for determination of PC/PD and cis/trans ratios and estimation of mDP (Czochanska et al, 1979(Czochanska et al, , 1980Foo et al, 2000a;Kraus et al, 2003) and boasts the only current analytical method for the identification of C4-C6 and C4-C8 linkages (Newman et al, 1987;Pizzi and Stephanou, 1993). A resurgence has occurred in the use of solid phase studies of CT-containing plant extracts using of cross-polarization magic angle spinning (CPMAS) solid-state 13 C NMR spectroscopy from which data similar to those of solutionstate 13 C NMR spectroscopy can be obtained (Hoong et al, 2010;Reid et al, 2013;Fryganas et al, 2018).…”

Section: Nmr Studiesmentioning

confidence: 99%

Activity, Purification, and Analysis of Condensed Tannins: Current State of Affairs and Future Endeavors

Zeller

2019

Crop Science

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As a class of plant polyphenolic compounds contained in some forages (i.e., sainfoin [Onobrychis viciifolia Scop.], big trefoil [Lotus pedunculatus Cav.], birdsfoot trefoil [Lotus corniculatus L.]), condensed tannins (CTs), also referred to as proanthocyanidins (PAs or PACs), exhibit a variety of biological effects on ruminants. The potential positive impact of CTs on the agricultural industry stems from their ability to modulate proteolysis during forage conservation and ruminal digestion, to prevent bloat, to reduce intestinal parasite burdens, to abate methane and ammonia emissions from ruminants, and to inhibit the activity of soil‐nitrifying bacteria. How CTs exert these effects on ruminants focuses on the interaction of CTs with proteins. The structure‐activity relationship in CT–protein interaction is not well understood but is known to be dependent on the structure and properties of both the CT and the protein. The purpose of this perspective is fivefold. First, we provide the reader with a better understanding of the structural diversity of CTs present in plant material and enable the reader to appreciate that not all CTs are the same. Second, we provide examples of how CT structural diversity affects the interaction of CTs with the protein, which, in turn, dictates the biological response from the animal. Third, we describe the hurdles in obtaining highly pure and well‐characterized CTs from natural sources for use in studies to attempt to elucidate how CTs impart each biological effect. We then describe improved and emerging techniques for CT analysis and, finally, we conclude this perspective with questions to address in future investigations and forward a list of recommendations for CT researchers to follow.

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Section: Nmr Studiesmentioning

confidence: 99%

Activity, Purification, and Analysis of Condensed Tannins: Current State of Affairs and Future Endeavors

Zeller

2019

Crop Science

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“…However, the bulk of PA polymers in plants usually have a higher degree of polymerisation (DP). Such polymers are then characterised by chemical degradation in the presence of a nucleophile, usually phloroglucinol33, 34 or benzylmercaptan,18, 26, 35, 36 and NMR spectroscopy 34. 35, 37, 38 Such methodologies allow characterisation of the nature of terminal and inner flavanol units and the average length of the chain.…”

Section: Chemical Structure Of Proanthocyanidinsmentioning

confidence: 99%

Proanthocyanidins and tannin-like compounds - nature, occurrence, dietary intake and effects on nutrition and health

Santos‐Buelga

Scalbert²

2000

J. Sci. Food Agric.

1,063

712

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Proanthocyanidins (syn condensed tannins) are complex flavonoid polymers naturally present in cereals, legume seeds and particularly abundant in some fruits and fruit juices. They share some common structural features—phenolic nature and high molecular weight—with phenolic polymers found in black tea and red wine (called here tannin‐like compounds). The polymeric nature of proanthocyanidins makes their analysis and estimation in food difficult. For this reason, little is known about their consumption, although they likely contribute a large part of the daily polyphenol intake. They also share common physicochemical properties: they form stable complexes with metal ions and with proteins and are, like other polyphenols, good reducing agents. Many of their biological effects of nutritional interest derive from these properties. As metal ion chelators, they influence the bioavailability of several minerals. The nutritional significance of the non‐specific complexation of proteins is less clear. As reducing agents, they may participate in the prevention of cancers, both of the digestive tract and inner organs. They may also protect LDLs against oxidation and inhibit platelet aggregation and therefore prevent cardiovascular diseases. In vitro, animal and human studies on the prevention of these chronic diseases are reviewed with particular attention to wine and tea polyphenols. The lack of data on their bioavailability and the paucity of human studies are emphasised. © 2000 Society of Chemical Industry

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“…Jji vitro and in vivo studies indicate that bean tannins decrease protein digestibility and protein quality (14). Condensed tannins and procyanidins are terms used to describe the same general class of compounds, plant phenolics that are polymers of the flavan-3-ols (Figure 2), (+) catechin and/or (-) epicatechin (15).…”

Section: Tannins/procyanidinsmentioning

confidence: 99%

Protein-Procyanidin Interaction and Nutritional Quality of Dry Beans

Artz¹,

Swanson²,

Sendzicki³

et al. 1986

Plant Proteins: Applications, Biological Effects, and Chemistry

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Thermodynamic analysis of the temperature dependance of procyanidin binding to bovine serum albumin (BSA) and bean glycoprotein G-1 suggested predominantly hydrophobic and hydrophilic binding, respectively. A cis-parinaric acid fluorescence assay for surface hydrophobicity supported amphiphilic interactions of procyanidin. Heat denatured G-1 had a surface hydrophobicity greater than native G-1. Procyanidin dimer and trimer inhibited trypsin digestion of BSA. In vitro digestibility and Tetrahymena-Protein Efficiency Ratio (t-PER) were inversely related to procyanidin concentration. Procyanidin intubation restricts rat growth and damages intestinalvilli. Procyanidins intubated with food or as dry beans were not as inhibitory as procyanidins intubated alone. Digestibility and PER of tempeh prepared with red beans and corn were less than the digestibility and PER of soybean tempeh. Tempeh, Rhizopus oligosporus, fermentation did not improve digestibility or nutritional quality of dry black beans.The common dry bean, Phaseolus vulgaris, is a grain legume consumed in large quantities around the world. Black and other colored beans provide appreciable protein, vitamins, minerals and calories for rural and urban populations of developing countries. The nutritional importance of beans is great since access to protein of animal origin is limited. Legumes and cereals, which contain complementary proteins, provide protein of greater quality than consumption of legumes or cereals alone. However, consumption of beans and cereals in a favorable nutritional quality ratio and amount tends to be infrequent in developing countries. World production of legumes appears to be declining compared to production and greater yields of cereals. Legume production, however, is still encouraged internationally to fix atmospheric nitrogen and contribute to increased soil fertility in developing countries. Dry

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Direct proof of a homogeneous polyflavan-3-ol structure for polymeric proanthocyanidins

Cited by 49 publications

References 0 publications

Activity, Purification, and Analysis of Condensed Tannins: Current State of Affairs and Future Endeavors

Activity, Purification, and Analysis of Condensed Tannins: Current State of Affairs and Future Endeavors

Proanthocyanidins and tannin-like compounds - nature, occurrence, dietary intake and effects on nutrition and health

Protein-Procyanidin Interaction and Nutritional Quality of Dry Beans

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