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1. Characterization by HPLC–ESI–MS2 of native and oxidized procyanidins from litchi (Litchi chinensis) pericarp

Author:
Miranda-Hernández, Angela M.; Muñiz-Márquez, Diana B.; Wong-Paz, Jorge E.; Aguilar-Zárate, Pedro; de la Rosa-Hernández, Martina; Larios-Cruz, Ramón; Aguilar, Cristóbal N.
Source:
Food chemistry 2019 v.291 pp. 126-131
ISSN:
0308-8146
Subject:
procyanidins,   etc   ; Litchi chinensis; acetone; bioactive properties; methanol; oxidation; pericarp; polymerization; solvents; tandem mass spectrometry; tannins;     Show all 11 Subjects
Abstract:
... Procyanidins (PCs) are polyphenols highly accumulated in litchi fruit (Litchi chinensis). Despite their bioactivity, the molecular composition of native and oxidized procyanidins is little understood. In this paper, polyphenols from litchi pericarp were extracted using two solvents (methanol and acetone). The mean degree of polymerization (mDP) of native and identification of oxidized PCs were car ...
DOI:
10.1016/j.foodchem.2019.04.020

2. Slow starch digestion in the rice cooked with adzuki bean: Contribution of procyanidins and the oxidation products

Author:
Takahama, Umeo; Hirota, Sachiko; Yanase, Emiko
Source:
Food research international 2019 v.119 pp. 187-195
ISSN:
0963-9969
Subject:
procyanidins,   etc   ; Vigna angularis; color; cooking; flavonoids; methanol; oxidation; red rice; reducing sugars; rice starch; starch; Japan;     Show all 12 Subjects
Abstract:
... Adzuki bean is often cooked with non-glutinous rice in Japan, and the dish is called adzuki-meshi. By the cooking, flavonoids in adzuki bean are transferred to rice, and the color of the rice becomes pale red. However, it has not been reported on starch digestion of the rice of adzuki-meshi. The purpose of this study is to elucidate that the transferred flavonoids, especially procyanidins could sl ...
DOI:
10.1016/j.foodres.2019.01.062

3. Valorization of lotus byproduct (Receptaculum Nelumbinis) under green extraction condition

Author:
Huang, Hao; Belwal, Tarun; Jiang, Lei; Hu, Juwu; Limwachiranon, Jarukitt; Li, Li; Ren, Guoping; Zhang, Xuebing; Luo, Zisheng
Source:
Food and bioproducts processing 2019 v.115 pp. 110-117
ISSN:
0960-3085
Subject:
procyanidins,   etc   ; byproducts; catechin; economic sustainability; food waste; glycerol; industrial applications; isoquercitrin; models; quercetin; solvents; temperature; viscosity;     Show all 13 Subjects
Abstract:
... Food waste including byproducts has been growing with increasing food and its products consumption, leading to various environmental problems. Considering valorization, the food waste could be converted into useful byproducts. Receptaculum Nelumbinis, a lotus byproduct, was considered to contain higher level of phenolic compounds. This study was designed to extract valuable phenolic compounds from ...
DOI:
10.1016/j.fbp.2019.03.006

4. A semisynthetic approach for the simultaneous reaction of grape seed polymeric procyanidins with catechin and epicatechin to obtain oligomeric procyanidins in large scale

Author:
Bai, Ruifang; Cui, Yan; Luo, Lanxin; Yuan, Danbing; Wei, Zongmin; Yu, Weichao; Sun, Baoshan
Source:
Food chemistry 2019 v.278 pp. 609-616
ISSN:
0308-8146
Subject:
procyanidins,   etc   ; bioactive properties; catechin; countercurrent chromatography; epicatechin; grape seeds; hydrochloric acid; response surface methodology; temperature;     Show all 9 Subjects
Abstract:
... Polymeric procyanidins (PPCs) were the major constituents of procyanidins, while they have poor bioactivity. To better utilize PPCs, a semisynthetic approach for converting PPCs to oligomeric procyanidins (OPCs) was proposed. Grape seed PPCs were simultaneously reacted with catechin (C) and epicatechin (EC) under acid condition. Combining response surface methodology (RSM) and single-factor experi ...
DOI:
10.1016/j.foodchem.2018.11.091

5. Self-aggregation of oxidized procyanidins contributes to the formation of heat-reversible haze in apple-based liqueur wine

Author:
Millet, Melanie; Poupard, Pascal; Guilois-Dubois, Sophie; Zanchi, Drazen; Guyot, Sylvain
Source:
Food chemistry 2019 v.276 pp. 797-805
ISSN:
0308-8146
Subject:
procyanidins,   etc   ; liqueurs; liquid chromatography; mass spectrometry; models; oxidation; polymerization; tannins; temperature; wines;     Show all 10 Subjects
Abstract:
... The ability of tannins to self-associate or form complexes with other macromolecules has important nutritional implications but can also result in defects in beverages. In addition, oxidation may be involved in the aggregation properties of tannins.In order to assess the impact of tannin oxidation on their self-association, oligomeric procyanidins were oxidized in a model solution and their aggreg ...
DOI:
10.1016/j.foodchem.2018.09.171

6. Protein–polyphenol interactions enhance the antioxidant capacity of phenolics: analysis of rice glutelin–procyanidin dimer interactions

Author:
Dai, Taotao; Chen, Jun; McClements, David Julian; Hu, Peng; Ye, Xiaoqin; Liu, Chengmei; Li, Ti
Source:
Food & function 2019 v.10 no.2 pp. 765-774
ISSN:
2042-650X
Subject:
procyanidins,   etc   ; antioxidant activity; computer simulation; emulsions; fluorescence emission spectroscopy; functional foods; glutelins; hydrophobicity; rice; rice protein;     Show all 10 Subjects
Abstract:
... Rice glutelin and procyanidins are often used in functional foods as sources of plant-based proteins and polyphenols, respectively, but little is currently known about the interactions between them. In our research, the interaction between rice glutelin and the B-type procyanidin dimer (PB2) was investigated. The presence of the PB2 decreased the α-helix and random coil structure of the rice prote ...
DOI:
10.1039/c8fo02246a

7. Some New Findings Regarding the Antiadhesive Activity of Cranberry Phenolic Compounds and Their Microbial-Derived Metabolites against Uropathogenic Bacteria

Author:
González de Llano, Dolores; Liu, Haiyan; Khoo, Christina; Moreno-Arribas, M. Victoria; Bartolomé, Begoña
Source:
Journal of agricultural and food chemistry 2019 v.67 no.8 pp. 2166-2174
ISSN:
1520-5118
Subject:
procyanidins,   etc   ; Enterococcus faecalis; Escherichia coli; bacteria; cranberries; hippuric acid; metabolites; methylation; propionic acid; urinary tract diseases;     Show all 10 Subjects
Abstract:
... Findings concerning the antiadhesive activity of cranberry phenolic compounds and their microbial-derived metabolites against Gram-negative (Escherichia coli ATCC 53503 and DSM 10791) and Gram-positive (Enterococcus faecalis 04-1) bacteria in T24 cells are reported. A-Type procyanidins (A2 and cinnamtannin B-1) exhibited antiadhesive activity (at concentrations ≥250 μM), a feature that was not obs ...
DOI:
10.1021/acs.jafc.8b05625

8. Effect of procyanidin on dietary iron absorption in hereditary hemochromatosis and in dysmetabolic iron overload syndrome: A crossover double-blind randomized controlled trial

Author:
Lobbes, Hervé; Gladine, Cécile; Mazur, Andrzej; Pereira, Bruno; Dualé, Christian; Cardot, Jean-Michel; Ruivard, Marc
Source:
Clinical nutrition 2019
ISSN:
0261-5614
Subject:
procyanidins,   etc   ; bioavailability; blood serum; food composition; hemochromatosis; iron; iron absorption; patients; placebos; test meals;     Show all 10 Subjects
Abstract:
... Type I hereditary hemochromatosis (HH) and dysmetabolic iron overload syndrome (DIOS) are the two most prevalent iron overload diseases. Although many food components, particularly polyphenols, reduce iron bioavailability, there is no clinically validated nutritional strategy to reduce food-iron absorption in patients with these diseases. We aimed to determine whether supplementation with 100 mg o ...
DOI:
10.1016/j.clnu.2019.02.012

9. A Computational Study on the Stereo- and Regioselective Formation of the C4α–C6′ Bond of Tethered Catechin Moieties by an Exhaustive Search of the Transition States

Author:
Fukaya, Keisuke; Saito, Akiko; Nakajima, Noriyuki; Urabe, Daisuke
Source:
Journal of organic chemistry 2019 v.84 no.5 pp. 2840-2849
ISSN:
1520-6904
Subject:
procyanidins,   etc   ; catechin; chemical reactions; geometry; hydrogen bonding; mechanics; models; moieties; organic chemistry; regioselectivity;     Show all 10 Subjects
Abstract:
... We previously reported the total synthesis of procyanidin B6 by using the stereo- and regioselective C–C bond formation of tethered catechin moieties as the key step. The reaction afforded the product bearing a new C4α–C6′ bond linkage instead of the inherently preferable C4α–C8′ bond. However, the origin of this selectivity remained unclear due to the complex structure of the substrate. Here we r ...
DOI:
10.1021/acs.joc.8b03263

10. Impact of a post-fermentative maceration with overripe seeds on the color stability of red wines

Author:
Rivero, Francisco J.; Jara-Palacios, M. José; Gordillo, Belén; Heredia, Francisco J.; González-Miret, M. Lourdes
Source:
Food chemistry 2019 v.272 pp. 329-336
ISSN:
0308-8146
Subject:
procyanidins,   etc   ; catechin; color; colorimetry; epicatechin; gallic acid; maceration; polymerization; red wines; seeds;     Show all 10 Subjects
Abstract:
... With the purpose of modulating the copigmentation equilibria of red wines, an environmentally sustainable process was performed based on post-fermentative addition of overripe seeds (OS). Simple (SW) and double (DW) addition were performed to produce different enrichment of phenolics from seeds, hence different copigmentation/polymerization ratios.The determination of the phenolic composition show ...
DOI:
10.1016/j.foodchem.2018.08.008

11. An approach for degradation of grape seed and skin proanthocyanidin polymers into oligomers by sulphurous acid

Author:
Luo, Lanxin; Cui, Yan; Cheng, Jinhui; Fang, Bairui; Wei, Zongmin; Sun, Baoshan
Source:
Food chemistry 2018 v.256 pp. 203-211
ISSN:
0308-8146
Subject:
procyanidins,   etc   ; grape seeds; grapes; polymers; proanthocyanidins; temperature;     Show all 6 Subjects
Abstract:
... To develop an efficient method for degradation of grape seed and skin proanthocyanidins polymers into oligomers, an optimized sulphurous acid degradation conditions for grape seed with the temperature of 60 °C, reaction time of 60 min and sample-sulphurous acid ratio of 1:0.2, and for grape skin with the temperature of 40 °C, reaction time of 60 min and sample-sulphurous acid ratio of 1:0.2, were ...
DOI:
10.1016/j.foodchem.2018.02.097

12. High performance thin-layer chromatography–mass spectrometry methods on diol stationary phase for the analyses of flavan-3-ols and proanthocyanidins in invasive Japanese knotweed

Author:
Glavnik, Vesna; Vovk, Irena
Source:
Journal of chromatography 2019 v.1598 pp. 196-208
ISSN:
0021-9673
Subject:
procyanidins,   etc   ; Reynoutria japonica; absorption; acetonitrile; chromatography; ethyl acetate; flavanols; polymerization; proanthocyanidins; rhizomes; silica gel; solvents; tandem mass spectrometry;     Show all 13 Subjects
Abstract:
... We developed the first four HPTLC methods for the separation of proanthocyanidins according to degree of polymerization on HPTLC diol F254S plates. Acetonitrile, ethyl acetate, ethyl acetate–formic acid (9:0.1, v/v) and toluene–acetone–formic acid (3:6:1, v/v) were used as developing solvents and 4-dimethylaminocinnamaldehyde (DMACA) as the detection reagent. Each of these methods enables separati ...
DOI:
10.1016/j.chroma.2019.03.050

13. Comprehensive structural characterization of phenolics in litchi pulp using tandem mass spectral molecular networking

Author:
Lyu, Qiang; Kuo, Ting-Hao; Sun, Chongde; Chen, Kunsong; Hsu, Cheng-Chih; Li, Xian
Source:
Food chemistry 2019 v.282 pp. 9-17
ISSN:
0308-8146
Subject:
procyanidins,   etc   ; Litchi; alpha-glucosidase; bioactive properties; enzyme inhibition; glycosides; health promotion; isorhamnetin; kaempferol; myricetin; pulp; quercetin; secondary metabolites;     Show all 13 Subjects
Abstract:
... Phenolic compounds are a large class of plant secondary metabolites with various health-promoting effects, and are known for their structural diversity. Therefore, high efficiency characterization of phenolic profiles is of key importance in identifying their potential bioactivity. In the present study, Global Natural Products Social (GNPS) Molecular Networking was applied to trace the phenolic co ...
DOI:
10.1016/j.foodchem.2019.01.001

14. Guaraná (Paullinia cupana) catechins and procyanidins: Gastrointestinal/colonic bioaccessibility, Caco-2 cell permeability and the impact of macronutrients

Author:
Mendes, Thaíse Maria Nogueira; Murayama, Yukihisa; Yamaguchi, Natsumi; Sampaio, Geni Rodrigues; Fontes, Luciana Cristina Brigatto; Torres, Elizabeth Aparecida Ferraz da Silva; Tamura, Hirotoshi; Yonekura, Lina
Source:
Journal of functional foods 2019 v.55 pp. 352-361
ISSN:
1756-4646
Subject:
procyanidins,   etc   ; Paullinia cupana; bioavailability; casein; catechin; epicatechin; human cell lines; humans; intestinal mucosa; oxidative stress; permeability; provenance; seeds; vegetable oil;     Show all 14 Subjects
Abstract:
... Guaraná (Paullinia cupana) seeds are rich in flavan-3-ols (catechins) and reduce oxidative stress in humans. We determined the concentration and in vitro bioaccessibility of catechins in guaraná seeds from two geographical origins, and measured their Caco-2 permeability. The effect of macronutrients on catechins’ bioaccessibility and Caco-2 permeability was also evaluated. Guaraná seeds from south ...
DOI:
10.1016/j.jff.2019.02.026

15. Pear ripeness and tissue type impact procyanidin-cell wall interactions

Author:
Brahem, Marwa; Renard, Catherine M.G.C.; Bureau, Sylvie; Watrelot, Aude A.; Le Bourvellec, Carine
Source:
Food chemistry 2019 v.275 pp. 754-762
ISSN:
0308-8146
Subject:
procyanidins,   etc   ; calorimetry; cell walls; hydrogen bonding; hydrophobic bonding; infrared spectroscopy; pears; ripening; sorption isotherms; titration; ultraviolet-visible spectroscopy;     Show all 11 Subjects
Abstract:
... Procyanidins and cell walls were extracted from pear at ripe and overripe stages in order to investigate the impact of ripening stage on their association. Procyanidin composition and structure remained stable at the overripe stage. Mid Infrared Spectroscopy (MIR) discriminated cell wall-procyanidin complex from initial purified cell wall material (CWM). Interactions between procyanidins and CWM i ...
DOI:
10.1016/j.foodchem.2018.09.156

16. Structure-activity relationship of procyanidins on advanced glycation end products formation and corresponding mechanisms

Author:
Chen, Yuanyuan; Tang, Shimiao; Chen, Yashu; Zhang, Roujie; Zhou, Mengzhou; Wang, Chao; Feng, Nianjie; Wu, Qian
Source:
Food chemistry 2019 v.272 pp. 679-687
ISSN:
0308-8146
Subject:
procyanidins,   etc   ; advanced glycation end products; beta-glucosidase; computer simulation; diabetes; free radicals; glycosylation; medicine; nutrition risk assessment; structure-activity relationships;     Show all 10 Subjects
Abstract:
... Nonenzymatic glycosylation (NEG) can generate advanced glycation end products (AGEs) and its intermediates α-dicarbonyl compounds, which contribute to the risk of diabetes. This study investigated the anti-glycation mechanisms and structure–activity relationship of (+)-catechin (CC) and (−)-epicatechin (EC). The results showed that the effect of CC on inhibiting AGEs was significantly better than ...
DOI:
10.1016/j.foodchem.2018.08.090

17. Insight of Stability of Procyanidins in Free and Liposomal Form under an in Vitro Digestion Model: Study of Bioaccessibility, Kinetic Release Profile, Degradation, and Antioxidant Activity

Author:
Toro-Uribe, Said; López-Giraldo, Luis Javier; Alvarez-Rivera, Gerardo; Ibáñez, Elena; Herrero, Miguel
Source:
Journal of agricultural and food chemistry 2019 v.67 no.7 pp. 1990-2003
ISSN:
1520-5118
Subject:
procyanidins,   etc   ; antioxidant activity; bioavailability; catechin; chemical structure; depolymerization; gastrointestinal system; in vitro digestion; lipids; models; polymers; tandem mass spectrometry;     Show all 12 Subjects
Abstract:
... Small unilamellar and multilayered liposomes loaded with polymeric (epi)catechins up to pentamers were produced. The bioaccessibility, kinetic release profile, and degradation under in vitro gastrointestinal conditions were monitored by UHPLC-DAD-QTOF-MS/MS. The results show that all of the procyanidins underwent depolymerization and epimerization into small molecular oligomers and mainly to (epi) ...
DOI:
10.1021/acs.jafc.9b00351

18. Rapid assembly of the procyanidin A skeleton

Author:
Kraus, George A.; Geraskin, Ivan M.
Source:
Tetrahedron letters 2017
ISSN:
0040-4039
Subject:
procyanidins,   etc   ; chemical reactions; chemical structure;     Show all 3 Subjects
Abstract:
... Arylpropynals and two equivalents of phloroglucinol react to produce pentacyclic ketals. In addition, 4-methoxydibromocinnamaldehyde also reacted to form procyanidin A-skeleton. ...
DOI:
10.1016/j.tetlet.2017.10.067

19. Predictive kinetic optimisation of hydrophilic interaction chromatography × reversed phase liquid chromatography separations: Experimental verification and application to phenolic analysis A

Author:
Muller, Magriet; Tredoux, Andreas G.J.; de Villiers, André
Source:
Journal of chromatography 2018 v.1571 pp. 107-120
ISSN:
0021-9673
Subject:
procyanidins,   etc   ; comprehensive two-dimensional liquid chromatography; hydrophilic interaction chromatography;     Show all 3 Subjects
Abstract:
... Method development and optimisation for comprehensive two-dimensional liquid chromatography (LC × LC) is complex, since this involves the intricate relationships between a large number of experimental parameters with the aim of achieving three conflicting goals: maximising separation performance (peak capacity), minimising analysis time and minimising dilution. This is especially true for the on-l ...
DOI:
10.1016/j.chroma.2018.08.004

20. Vine-Shoot Tannins: Effect of Post-pruning Storage and Toasting Treatment

Author:
Cebrián-Tarancón, Cristina; Sánchez-Gómez, Rosario; Gómez-Alonso, Sergio; Hermosín-Gutierrez, Isidro; Mena-Morales, Adela; García-Romero, Esteban; Salinas, M. Rosario; Zalacain, Amaya
Source:
Journal of agricultural and food chemistry 2018 v.66 no.22 pp. 5556-5562
ISSN:
1520-5118
Subject:
procyanidins,   etc   ; cultivars; polymerization; proanthocyanidins; storage time; tannins; toasting;     Show all 7 Subjects
Abstract:
... For the first time vine-shoot tannin composition was carried out by means of HPLC-DAD-ESI-MS/MS. Two vine-shoot cultivars (Airén and Cencibel) with different post-pruning storage times were submitted to a toasting process and assayed. There were no traces of gallotannins nor ellagitannins, but a high proanthocyanidin content and a mean degree of polymerization (mDP) close to 3 were characterized. ...
DOI:
10.1021/acs.jafc.8b01540