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CARBOHYDRATE POLYMERS · 2020 · IF 7.182

Inhibition effect of three common proanthocyanidins from grape seeds, peanut skins and pine barks on maize starch retrogradation

Mengting Wang,Jianchu Chen,Shiguo Chen,Xingqian Ye,Donghong Liu

The inhibition effect of three common proanthocyanidins (PA) on the retrogradation properties of maize starch was investigated (including grape seed proanthocyanidins (GSPA), peanut skin proanthocyanidins (PSPA), and pine bark proanthocyanidins (PBPA)). Differential scanning calorimetry (DSC) and X-ray diffraction (XRD) analysis showed that PA could significantly decrease the values of melting enthalpy of retrogradation ( ΔH r ) and the degree of relative crystallinity, suggesting that the starch re-crystallization was retarded by PA. Scanning electron microscope (SEM) characterizations illustrated that retrograded PA-starch samples formed a looser matrix with less appearance of continuous flakes during storage. Overall, 0.5 %–2.0 % of three PAs exhibited suppression of starch retrogradation after 21-day cooling storage, mainly resulting from the PA-starch interaction. Among them, PSPA showed the most substantial inhibition effect on starch retrogradation, which might be attributed to its structural features. This study suggested that PA could be a new type of inhibitor to suppress starch retrogradation.

CAS / MDL: 9005-25-8
研究领域: 食品科学 · 化学 · 农业科学
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FOOD CHEMISTRY · 2023 · IF 8.8

Investigating wine astringency profiles by characterizing tannin fractions in Cabernet Sauvignon wines and model wines

Qinghao Zhao,Guorong Du,Pengtao Zhao,Anque Guo,Xiaomeng Cao,Chenyaqiong Cheng,Hui Liu,Fei Wang,Yuefan Zhao,Yan Liu,Xiaoyu Wang

Contribution of various phenols on wine astringency profiles was far from clear explanations. To effectively describe wine astringency profiles and determined the function of tannins/matrix (pH and ethanol), multiple chemical analyses combined RATA (Rate-all-that-apply) sensory method were applied in Cabernet Sauvignon and model wines. Results showed that polymeric flavanols determined the bulk of wine astringency intensity, oligomeric tannins enriched the smoothness and periodontium astringency, and monomeric phenol enhanced overall astringency intensity through synergistic effect. Astringency balance was effectively quantification, and its potential correlation relationship with epicatechin extension subunit (0.83) and fluorescence peak shift (0.75) cannot be ignored. The astringency profiles of condensed tannins with anthocyanins were enhanced. Low-pH (from 3.8 to 3.0) enhanced astringency by increasing the tannins affinity to proteins, while ethanol (from 10.0 % ∼ 15.0 %) decreased the hydrophobicity bond between tannins-protein interaction. This paper provided new insights to explain wine astringency profiles and a reference for astringency modification during winemaking.

CAS / MDL: 100-53-8 6203-18-5
研究领域: 食品科学 · 感官分析 · 化学
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CHEMICAL PHYSICS LETTERS · 2020 · IF 2.029

Synthesis of proanthocyanidins-functionalized Fe3O4 magnetic nanoparticles with high solubility for removal of heavy-metal ions

Yuzhe Shi,Yayan Xing,Shixian Deng,Baihan Zhao,Yujie Fu,Zhiguo Liu

Large-scale hydrophilic proanthocyanidins-functionalized Fe 3 O 4 nanoparticles were synthesized via a hydrothermal approach. The obtained Fe 3 O 4 nanocomposites were characterized by Fourier transform infrared spectroscopy (FTIR), scanning electron microscopy (SEM), transmission electron microscopy (TEM) and X-ray diffraction (XRD). The results revealed that the Fe 3 O 4 nanoparticles had cubic spinel structure and capped by proanthocyanidins outside. Furthermore, the proanthocyanidins-functionalized Fe 3 O 4 nanoparticles can be utilized to adsorb the heavy metal ions in water. The primary results indicated that the proanthocyanidins-functionalized Fe 3 O 4 nanoparticles have high removal rate for Cu 2+ , Cd 2+ and Pb 2+ in water.

CAS / MDL: 20347-71-1
研究领域: 材料科学 · 环境科学
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FOOD CHEMISTRY · 2024 · IF 8.5

Study on the extraction, purification, stability, free radical scavenging kinetics, polymerization degree and characterization of proanthocyanidins from Pinus koraiensis seed scales

Zhanjun Li,Yibin Xu,Yunwei Liu,Mingru Kong,Jiarong Wang,Yanxia Li,Yuhong Zhao

To efficiently harness resources from Pinus koraiensis seed scales, a type of forestry waste, rigorous studies on the extraction, purification , stability, and free radical scavenging capacity of the proanthocyanidins derived from these seed scales were conducted. Kinetic models showed that under ultrasonic conditions, the proanthocyanidins content reached 2.66 mg/g within 0.5 h. The optimal storage parameters include darkness, 4 °C, and pH 4. The degrees of polymerization of the mixture and the high- and low-polymer components were 4.89, 7.42 and 3.07, respectively, with the low-polymer component exhibiting the highest radical scavenging activity. Through HPLC–QE-MS/MS, 1 H NMR, and FT-IR analyses, we identified proanthocyanidin B1, proanthocyanidin B2, (−)-epicatechin, and polymeric trimer esters. The Pinus koraiensis proanthocyanidins exhibited a high molecular weight, a complex internal molecular structure, and commendable stability, with crystallization requiring elevated temperatures. Therefore, the proanthocyanidins from Pinus koraiensis seed scales have emerged as highly promising novel natural antioxidants .

研究领域: 林学 · 天然产物化学 · 生物化学
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COLLOIDS AND SURFACES B-BIOINTERFACES · 2018 · IF 3.997

Synthesis and characterization of proanthocyanidins-functionalized Ag nanoparticles

Linhai Biao,Shengnan Tan,Xuewei Zhang,Jing Gao,Zhiguo Liu,Yujie Fu

Preparation of Ag nanoparticles with high antibacterial activities and low adverse effects is urgently needed to apply to the medical and consumer products. In this study, a facile, one-step hydrothermal method has been developed to synthesize proanthocyanidins-functionalized Ag nanoparticles in aqueous solution. UV absorption spectra measurement indicated that the obtained Ag nanomaterials are mainly spherical in shape. FTIR results implied that the poly flavonoids moiety of proanthocyanidins have specific interactions with the surface of Ag nanoparticles. HR-TEM and XRD determination revealed that the Ag nanoparticles had a shell-core structure and the Ag core possessed a highly crystalline structure. Antibacterial tests demonstrated that the proanthocyanidins-functionalized-Ag nanoparticles have high bactericidal efficiency against both bacterial and fungus. Further taking into account their excellent stability, the proanthocyanidins-functionalized Ag nanoparticles in present study have the potential to be applied to the products required for the long-acting antibacterial action.

CAS / MDL: 20347-71-1
研究领域: 材料科学 · 微生物学 · 纳米生物学
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Arabian Journal of Chemistry · 2021 · IF 5.165

Cinnamomum camphora leaves as a source of proanthocyanidins separated using microwave-assisted extraction method and evaluation of their antioxidant activity in vitro

Zaizhi Liu,Hualan Li,Yanlong Qi,Zheng Zhu,Dai Huang,Ke Zhang,Jun Pan,Lan Wen,Zhengrong Zou

Cinnamomum camphora is a notable tree species of great significance to human beings. Proanthocyanidins (PCs) were separated from C. camphora leaves using microwave assisted extraction (MAE) method. Four variables of the MAE procedure were studied using the Box-Behnken design of response surface method. The results demonstrated that the optimal extraction conditions were: ethanol concentration of 77%; liquid/solid ratio of 20 mL/g, microwave time of 18 min, and microwave power of 530 W to achieve an actual yield of 81.56 ± 2.03 mg/g for C. camphora PCs. Extraction kinetic study results indicated that MAE is the most efficient method for C. camphora leaf PCs extraction under the obtained conditions in comparison to the reference methods (heat reflux extraction, ultrasound extraction, and Soxhlet extraction), by which the highest yield of PCs and the volumetric mass transfer coefficient were obtained in the shortest extraction time. Antioxidant activity study revealed that C. camphora leaf PCs could be used as a natural alternative to the synthetic commercial antioxidants.

研究领域: 植物化学 · 药理学
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PLoS One · 2015 ·Vol. 10 ·期 3 ·e0120480 · IF 3.234

Identification of Proanthocyanidins from Litchi (Litchi chinensis Sonn.) Pulp by LC-ESI-Q-TOF-MS and Their Antioxidant Activity

Qiang Lv,Fenglei Luo,Xiaoyong Zhao,Yu Liu,Guibing Hu,Chongde Sun,Xian Li,Kunsong Chen

Content of total proanthocyanidins as well as total phenolics, flavonoids, antioxidant activities were evaluated for litchi ( Litchi chinensis Sonn.) pulp of 32 cultivars. One cultivar, Hemaoli, showed the highest total proanthocyanidins and total phenolics, and DPPH or ABTS radical scavenging activities. ESI-MS and NMR analysis of the Hemaoli pulp crude extracts (HPCE) showed that procyandins composed of ( epi )catechin unites with degree of polymerization (DP) of 2–6 were dominant proanthocyanidins in HPCE. After the HPCE was fractionated by a Sephadex LH-20 column, 32 procyanidins were identified by LC-ESI-Q-TOF-MS in litchi pulp for the first time. Quantification of individual procyanidin in HPCE indicated that epicatechin, procyanidin B2, procyanidin C1 and A-type procyanidin trimer were the main procyanidins. The radical scavenging activities of different fractions of HPCE as well as six procyanidins standards were evaluated by both DPPH and ABTS assays. HPCE fractions showed similar antioxidant activities with those of Vc and six individual procyanidins, the IC 50 of which ranged from 1.88 ± 0.01 to 2.82 ± 0.10 μg/ml for DPPH assay, and from 1.52 ± 0.17 to 2.71 ± 0.15 μg/ml for ABTS assay. Such results indicate that litchi cultivars rich in proanthocyanidins are good resources of dietary antioxidants and have the potential to contribute to human health.

CAS / MDL: 28752-68-3
研究领域: 食品科学 · 植物化学 · 营养学
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INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES · 2023 ·Vol. 24 ·期 7 ·6379 · IF 5.6

Proanthocyanidin Structure-Activity Relationship Analysis by Path Analysis Model

Zhaoxuan Li,Jingling Liu,Jie You,Xin Li,Zongsuo Liang,Junli Du

To fully explore the influence mechanism of interactions between different monomer units of proanthocyanidins (PAs) on biological activity, a path analysis model of the PA structure-activity relationship was proposed. This model subdivides the total correlation between each monomer unit and activity into direct and indirect effects by taking into account not only each monomer unit but also the correlation with its related monomer units. In addition, this method can determine the action mode of each monomer unit affecting the activity by comparing the direct and total indirect effects. Finally, the advantage of this model is demonstrated through an influence mechanism analysis ofRhodiola crenulataPA monomer units on antioxidant and anti-diabetes activities.Keywords:proanthocyanidins;structure-activity relation;path analysis;Rhodiola crenulata

CAS / MDL: 484-11-7
研究领域: 药理学 · 化学生物学 · 植物科学
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PLANT CELL AND ENVIRONMENT · 2024 · IF 6

A structural variation in the promoter of the leucoanthocyanidin reductase gene AaLAR1 enhances freezing tolerance by modulating proanthocyanidin accumulation in kiwifruit (Actinidia arguta)

Shihang Sun,Xiujuan Qi,Zhenzhen Zhang,Leiming Sun,Ran Wang,Yukuo Li,Jinyong Chen,Hong Gu,Jinbao Fang,Miaomiao Lin

Proanthocyanidins (PAs) are important metabolites that enhance freezing tolerance of plants. Actinidia arguta , especially freezing-tolerant germplasms, accumulate abundant PAs in dormant shoots and thereby enhance freezing tolerance, but the underlying mechanism is unknown. In this study, we used two A. arguta with contrasting cold-resistant phenotypes, KL and RB, to explore the mechanisms in response to cold tolerance. We determined that a leucoanthocyanidin reductase gene ( AaLAR1 ) was more highly expressed in freezing-tolerant KL than in freezing-sensitive RB. Moreover, overexpressing AaLAR1 in kiwifruit promoted PAs biosynthesis and enhanced cold tolerance. The AaLAR1 promoters of various A. arguta germplasms differ due to the presence of a 60-bp deletion in cold-tolerant genotypes that forms a functional binding site for MYC-type transcription factor. Yeast one-hybrid and two-hybrid, dual-luciferase reporter, bimolecular fluorescence complementation and coimmunoprecipitation assays indicated that the AaMYC2a binds to the MYC-core cis -element in the AaLAR1 promoter with the assistance of AaMYB5a, thereby promoting PAs accumulation in the shoots of cold-tolerant kiwifruit. We conclude that the variation in the AaLAR1 promoter and the AaMYC2a–AaMYB5a– AaLAR1 module shape freezing tolerance in A. arguta . The identification of a key structural variation in the AaLAR1 promoter offers a new target for resistance breeding of kiwifruit.

CAS / MDL: 20347-71-1
研究领域: 植物生理学 · 分子生物学 · 遗传学
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Scientific Reports · 2015 ·Vol. 5 ·期 1 ·1-15 · IF 5.578

Analysis of accumulation patterns and preliminary study on the condensation mechanism of proanthocyanidins in the tea plant [Camellia sinensis]

Jiang Xiaolan,Liu Yajun,Wu Yahui,Tan Huarong,Meng Fei,Wang Yun sheng,Li Mingzhuo,Zhao Lei,Liu Li,Qian Yumei,Gao Liping,Xia Tao

In the present study, proanthocyanidins were qualitatively and quantitatively identified using hydrolysis and thiolysis assays, NP-HPLC, HPLC-ESI-MS, MALDI-TOF-MS, 1 H-NMR and 13 C-NMR techniques in different organs of tea plants. The results showed that in leaves, the tri-hydroxyl, cis - and galloylated flavan-3-ols were the main monomeric catechins units and (epi)catechin was found to be the major unit of polymeric flavan-3-ols when the degree of polymerization was greater than five. In roots, the PAs were found to be abundant and epicatechin formed the predominant extension unit of oligomeric and polymeric PAs. In order to understand the mechanism of proanthocyanidins polymerization, auto-condensation of the flavan-3-ols was investigated. The results showed that the same trimers ( m/z 865) were detected in the extracts of tea plants and in the non-enzymatic in vitro assay, in weak acid as well as weak alkaline solutions at room temperature, when the substrates used were either procyanidin B2 and monomeric flavan-3-ols (epicatechin or catechin), or only procyanidin B2. This suggested that procyanidin B2 not only released carbocation as electrophilic upper units, but also could be used as nucleophilic lower units directly itself, to form the procyanidin trimer in vitro or in vivo .

研究领域: 植物化学 · 代谢组学 · 分子生物学
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JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE · 2024 · IF 3.3

Dynamic changes in proanthocyanidin composition, biosynthesis, and histochemistry in spine grape (Vitis davidii Foëx) tissues during berry development

Yinfang Yan,Lin Li,Mingyuan Zheng,Bingbing Duan,Jiajing Zhang,Yashan Li,Wei Liu,Xu Liu

BACKGROUND Spine grapes are widely cultivated in southern China because of their strong adaptability to hot and humid climates. As a wild species native to China, spine grape ( Vitis davidii Foëx) was studied as a resource of proanthocyanidins (PAs). PA composition, biosynthesis, and histochemistry in different tissues (skins, seeds, and stems) during berry development were analyzed in this study. RESULTS The findings revealed that PA accumulation occurred in concurrence with flowering and was completed by veraison. High-performance liquid chromatographic results showed that the epicatechin type was the most dominant. The skins were more likely to accumulate PA polymers. Reverse transcription–quantitative polymerase chain reaction analysis revealed that the expression levels of structural genes (flavonoid-3′-hydroxylase, flavonoid-3′5′-hydroxylase, dihydroflavonol 4-reductase, leucoanthocyanidin reductase, and leucoanthocyanidin dioxygenase) were positively associated with PA dynamic changes. Histochemical results revealed that PAs in skins were mainly found in the hypodermis of the exocarp, PAs in seeds were mainly found in the middle layer of the outer integument of the testa, and PAs in stems were mainly found in the phloem. CONCLUSION This study provides a clear understanding of the spatial and temporal accumulation of PAs in spine grape, and forms a basis for the analysis of structural profiles and synthesis of PAs and their biological effects. © 2024 Society of Chemical Industry.

研究领域: 植物学 · 生物化学
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2017 · IF 2.329

Adsorption of procyanidins onto chitosan-modified porous rice starch

Suwei Jiang,Zhenyu Yu,Hailiang Hu,Jian Lv,Hualin Wang,Shaotong Jiang

Polyphenolic bioflavonoids are easily oxidized when exposed to oxygen during the processing or storage. This research developed a porous chitosan-modified starch for the adsorption of procyanidins . The modified starch was fabricated by a facile surface modification of chitosan on porous rice starch. Besides the investigation of the morphologies and structures of starches, the adsorption kinetics of procyanidins onto starches was evaluated. The modified starch was mesoporous with a relative moderate specific surface area at 1.13 ± 0.05 m 2 /g, and the interactions between starch and chitosan were intermolecular hydrogen bonds. The modification of chitosan resulted in the positive zeta potential of starch at pH 2-10. The enzymolysis reduced starch size slightly and induced a decrease in the apparent viscosity of starch suspension, while the modification of chitosan increased starch size and induced an increase in the apparent viscosity of the suspension. The adsorption capacity of the modified starch towards procyanidins was significantly improved and reached 96 ± 3% of the total amount of procyanidins, and the adsorption was chemisorption or strong surface complexation rather than mass transport. The results suggested that the porous chitosan-modified starch might be used as an efficient adsorbent for polyphenols.

研究领域: 食品科学 · 生物化学
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