Zur Kenntnis der Proanthocyanidine, XI1) Konfigurationsbestimmung von C30H26O12‐Procyanidinen und Strukturaufklärung eines neuen Procyanidins

Weinges, Klaus; Göritz, Klaus; Nader, Franz W.

doi:10.1002/jlac.19687150118

Cited by 76 publications

(20 citation statements)

References 3 publications

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“…The observation of one set of signals for solutions in CDCI 3 therefore would be consistent with one dominating conformer being present. In this respect our data for procyanidin B3 concur within experimental accuracy with the data reported by WEINGES et al (16). As all the trimeric proanthocyanidins investigated in this study show a similar pattern, it is suggested that CDCI3 interferes with their molecular configurations yielding only one observable rotamer.…”

Section: H Outtrup ~S K Schaumburg: Ih Nmr Of Proanthocyanidinssupporting

confidence: 92%

“…However, the location of the 6[~-signal in procyanidin BI (15,16) excludes the presence of (-)-epicatechin as a unit in the four trimers investigated. The aliphatic signals arising from the pyrane rings are very similar in all four compounds (cf.…”

Section: H Outtrup ~S K Schaumburg: Ih Nmr Of Proanthocyanidinsmentioning

confidence: 93%

“…In Figure 2c it is seen that two secondary structures are present in almost equal quantities (6). Since D2 in every respect is identical with procyanidin B3 (9,12,13,16,17), it is assumed that the procyanidin D2 is identical with this compound. The prodelphinidin DI possesses the same configuration as D2 in the upper unit judged by the magnitude of the coupling constants (Table I).…”

Section: H Outtrup ~S K Schaumburg: Ih Nmr Of Proanthocyanidinsmentioning

confidence: 99%

“…In Figure 3 and Figure 4 the data for procyanidin B3 (D2)and the dimeric prodelphinidin (191) are represented on the same scale as those of (+)-catechin, (-)-epicatechin and procyanldin B1 (15,16). The 8-values for the four trimeric compounds (T1-T4) are represented in the upper halves of the same figures.…”

Section: H Outtrup ~S K Schaumburg: Ih Nmr Of Proanthocyanidinsmentioning

confidence: 99%

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Structure elucidation of some proanthocyanidins in barley by1H 270 MHz NMR spectroscopy

Outtrup

Schaumburg

1981

Carlsberg Res. Commun.

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In the present paper the composition of proanthocyanidins isolated from barley is investigated. Separation by affinity chromatography and HPLC yields a large number of substances. Six of these have been isolated in this work. Based on the chromatographic preparation they are expected to be two dimers DI and D2 and four trimeric substances TI -T4. Studies by means of IH NMR spectroscopy at 270 MHz confirmed DI and D2 as being dimeric compounds, a prodelphinidin and procyanidin B3 respectively. The spatial structure of the prodelphinidin corresponds to procyanidin B3. The peracetates of all six compounds have also been studied by means of IH NMR spectrocopy. By comparison with data for the analogous peracetates of (+)-catechin and (-)-epicatechin and with literature data, T1 -T4 have been identified as trimeric proanthocyanidins and their structures have been elucidated.

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Section: H Outtrup ~S K Schaumburg: Ih Nmr Of Proanthocyanidinssupporting

confidence: 92%

Section: H Outtrup ~S K Schaumburg: Ih Nmr Of Proanthocyanidinsmentioning

confidence: 93%

Section: H Outtrup ~S K Schaumburg: Ih Nmr Of Proanthocyanidinsmentioning

confidence: 99%

Section: H Outtrup ~S K Schaumburg: Ih Nmr Of Proanthocyanidinsmentioning

confidence: 99%

See 2 more Smart Citations

Structure elucidation of some proanthocyanidins in barley by1H 270 MHz NMR spectroscopy

Outtrup

Schaumburg

1981

Carlsberg Res. Commun.

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“…The 1 H-NMR spectrum of acetate 4a showed no difference from compound 3a (epicatechin pentaacetate). The heterocyclic protons displayed an ABMX-system characteristic for the spin pattern of 2,3-cis-flavan-3-ols (J 2,3 <2.0 Hz) [12,13]. ent-epicatechin.…”

Section: Nmr Cosy Mass Spectrometry-esi-ms [ ]°2mentioning

confidence: 99%

Antioxidant Capacity and In Vitro Prevention of Dental Plaque Formation by Extracts and Condensed Tannins of Paullinia cupana

et al. 2007

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Chemical evaluation of the semi-purified fraction from the seeds of guaraná, Paullinia cupana H.B.K. var. sorbilis (Mart.) Ducke, yielded the following compounds: caffeine, catechin, epicatechin, ent-epicatechin, and procyanidins B 1 , B 2 , B 3 , B 4 , A 2 , and C 1 . Measurement of the antioxidant activity by reduction of the DPPH radical confirmed the anti-radical properties of the aqueous (AqE) and crude (EBPC) extracts and semi-purified (EPA and EPB) fractions. The EPA fraction showed radical-scavenging activity (RSA) and protected DPPH from discoloration at 5.23±0.08 (RSD%=1.49) µg/mL, and for the phosphomolybdenum complex showed a higher Relative Antioxidant Capacity (RAC) at 0.75±0.01 (1.75). The EPA fraction had a total polyphenolics content of 65.80%±0.62 (RSD%=0.93). The plant drug showed 5.47% ± 0.19 (RSD%=3.51) and 6.19% ± 0.08 (RSD%=1.29) for total polyphenolics and methylxanthines, respectively. In vitro assessment of the antibacterial potential of the Paullinia cupana extracts against 1951Streptococcus mutans showed that these could be used in the prevention of bacterial dental plaque.

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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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Zur Kenntnis der Proanthocyanidine, XI¹⁾ Konfigurationsbestimmung von C₃₀H₂₆O₁₂‐Procyanidinen und Strukturaufklärung eines neuen Procyanidins

Cited by 76 publications

References 3 publications

Structure elucidation of some proanthocyanidins in barley by1H 270 MHz NMR spectroscopy

Structure elucidation of some proanthocyanidins in barley by1H 270 MHz NMR spectroscopy

Antioxidant Capacity and In Vitro Prevention of Dental Plaque Formation by Extracts and Condensed Tannins of Paullinia cupana

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

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