Absolute Configuration of Native Oligomeric Proanthocyanidins with Dentin Biomodification Potency

Nam, Joo Won; Phansalkar, Rasika S.; Lankin, David C.; McAlpine, James B.; Leme-Kraus, Ariene A.; Vidal, Cristina; Gan, Li She; Bedran-Russo, Anakarina B.; Chen, Shao-Nong; Pauli, Guido F.

doi:10.1021/acs.joc.6b02161

Cited by 37 publications

(107 citation statements)

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“…Access to the full 3D structure of PAC trimers, tetramers, and even higher oligomers in their native, underivatized form is critical to establish structure activity relationships from the subsequent biological evaluation, such as for the dentin biomodification potential of the compounds presented here, which were isolated from fractions with known bioactivity. The presented structural data expands both our prior reports [9][10][11] as well as other PAC literature by providing accurately and precisely assigned 13 C NMR resonances. This forms the knowledge base for making absolute stereochemical assignments of PAC monomers via inclusion of the -gauche effect observed in the 13 C NMR resonances of PACs, as well as the determination of differential (s.c.s) 13 C chemical shift values (C) relative to those in the terminal monomers and analogous dimers (here: 2 and 46).…”

Section: ■ Conclusionsupporting

confidence: 82%

“…ABSTRACT: Guided by dentin biomechanical bioactivity, this phytochemical study led to the elucidation of an extended set of structurally demanding proanthocyanidins (PACs). Unambiguous structure determination involved detailed spectroscopic and chemical characterization of four A-type dimers (2,(4)(5)(6), seven trimers (10)(11)(12)(13)(14)(15)(16), and six tetramers (17)(18)(19)(20)(21)(22). New outcomes confirm the feasibility of determining the absolute configuration of the catechol monomers in oligomeric PACs by 1D and 2D NMR.…”

mentioning

confidence: 92%

“…In addition to the four known A-type dimers, epicatechin-(2→O→7,4→8)-catechin (2), 9 epicatechin-(2→O→7,4→8)-epicatechin (4), 9 epicatechin-(2→O→7,4→8)-ent-catechin (5), 10 and epicatechin-(2→O→7,4→8)-ent-epicatechin (6) 10 reported previously from this plant, seven trimers (10−16) and six tetramers (17−22) were isolated and characterized (Figure 1). Among these 13 PACs, eight are new structures, and one (11) 9 was revised based on new NMR evidence.…”

mentioning

confidence: 99%

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Tri- and Tetrameric Proanthocyanidins with Dentin Bioactivities from Pinus massoniana

Zhou¹,

Alania²,

Reis³

et al. 2020

Preprint

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Guided by dentin biomechanical bioactivity, this phytochemical study led to the elucidation of an extended set of structurally demanding proanthocyanidins (PACs). Unambiguous structure determination involved detailed spectroscopic and chemical characterization of four A-type dimers (2, 4–6), seven trimers (10–16), and six tetramers (17–22). New outcomes confirm the feasibility of determining the absolute configuration of the catechol monomers in oligomeric PACs by 1D and 2D NMR. Electronic circular dichroism (ECD) as well as phloroglucinolysis followed by MS and chiral phase HPLC analysis generated the necessary chiral reference data.

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Section: ■ Conclusionsupporting

confidence: 82%

mentioning

confidence: 92%

mentioning

confidence: 99%

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Tri- and Tetrameric Proanthocyanidins with Dentin Bioactivities from Pinus massoniana

Zhou¹,

Alania²,

Reis³

et al. 2020

Preprint

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“…Calculation of the number of potential isomers in a CT oligomer/polymer (Table 1) was performed using the equation (A m × B n ) = number of possible isomers, in which A = number of different flavan-3-ol subunit types in the compound, m = the actual number of flavan-3-ol subunits in the compound, B = the number of different types of interflavan linkages present in the compound, and n = the actual number of interflavan linkages present in the compound. Similar formulas have been reported to determine the number of CT structural isomers (Cheynier, 2005;Nam et al, 2017). The number of different unique compounds that could arise from CT containing two different flavan-3-ol subunits and only two types of interflavan linkages is listed in column A (Table 1).…”

Section: Limitations and Future Directionsmentioning

confidence: 79%

The role of condensed tannins in ruminant animal production: advances, limitations and future directions

et al. 2017

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-Tannins represent one of the most abundant polyphenolic compounds in plants. Tannins exist as a multitude of chemically unique entities in nature. The most commonly occurring tannins are typically divided into two major classes based on chemical structure: hydrolysable (HT) or condensed tannins (CT). Hydrolysable tannins are esters of gallic or ellagic acid linked to a polyol core, typically glucose. Condensed tannins or proanthocyanidins consist of flavan-3-ol subunits linked together to form oligomers and polymers. Both HT and CT are defined as astringent, medium-to-high-molecular weight polyphenolic compounds that characteristically bind and precipitate soluble proteins. The objective of this paper was to present recent advances in CT-ruminant interactions, the limitations associated with understanding and using CT in ruminant animal production, and future needs for research to further advance our knowledge of the role of CT in optimization of ruminant animal production. Condensed tannins pose some anti-nutritional problems to ruminants due to their astringent property that reduces feed intake and, consequently, animal performance. Ruminants can, however, tolerate CT by slowly adapting the ruminal microbes to the toxic effects of CT and by releasing CT-binding salivary proteins. The protein-binding ability of CT has some benefits to the ruminant due to complexes formed with essential amino acids, preventing their degradation in the rumen, but releasing them in the lower gut for absorption by the animal. Recent data have suggested increased N retention when CT is given to growing animals. There are potential benefits of using CT and HT for anthelmintic purposes due to their ability to inhibit egg hatching and larval motility of gastrointestinal nematode parasites, especially in small ruminants. Condensed tannins also bind to minerals (Al, Ca, Co, Cu, Fe, Mg, Mn, P, and Zn). Although studies with ruminants have been contradictory, it has been reported that because the CT-metal ion complex is stable over a wide pH range, CT may reduce the bioavailability of minerals. Methane mitigation by feeding CT might be the most impactful benefit for ruminant production. Many empirical equations have been developed to predict ruminal methane emissions, but very few have included CT. Future research should focus on the improvement of methodology to assess CT biological activity, interaction with other plant-specialized metabolites, and associated physiological and nutritional impacts on ruminants.

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“…The relatively great stability of OP(A)Cprotein complexes suggests structural specificity. Indeed, two new trimeric and tetrameric A-type OP(A)Cs capable of strengthening the micromolecular backbone of teeth via intermolecular and intermicrofibrillar cross-linking have been reported (79). The applications in dentistry include disease prevention (caries) and partial tooth repair.…”

Section: Expanding the Repertoire Of Vitamin P Candidatesmentioning

confidence: 99%

Vitamin P – Do Certain Polyphenolic IMPS Have a Vital Function?

Pauli¹

2020

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Abbreviations used: IMPS, invalid/improbable/interfering metabolic panaceas; PAC, proanthocyanidins; OPAC, oligomeric proanthocyanidins. AbstractIn the 1930s, it was discovered that the ability of synthetic Vitamin C to treat scurvy was inferior to plant extracts containing Vitamin C. This observation led to the proposal of Vitamin P (permeability), as an essential phytochemical dietary nutrient. Subsequent attempts to isolate and characterize Vitamin P led to confusing and sometimes irreproducible results. Over the years several flavonoids and coumarins have been identified as having Vitamin P-like activity.Essentially all of these Vitamin P candidates were recently identified as IMPs (Invalid/Improbable/Interfering Metabolic Panaceas) in a NAPRALERT meta analysis. While the historic inability to define a single compound and specific mode of action led to general skepticism about the Vitamin P proposition, the more logical conclusion is that several abundant and metabolically labile plant constituents fill this essential role in human nutrition. This review of 100+ years of multilingual Vitamin P and C literature provides the rationales for this conclusion.

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Absolute Configuration of Native Oligomeric Proanthocyanidins with Dentin Biomodification Potency

Cited by 37 publications

References 35 publications

Tri- and Tetrameric Proanthocyanidins with Dentin Bioactivities from Pinus massoniana

Tri- and Tetrameric Proanthocyanidins with Dentin Bioactivities from Pinus massoniana

The role of condensed tannins in ruminant animal production: advances, limitations and future directions

Vitamin P – Do Certain Polyphenolic IMPS Have a Vital Function?

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