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LWT-FOOD SCIENCE AND TECHNOLOGY · 2020 · IF 4.006

Different distribution of free and bound phenolic compounds affects the oxidative stability of tea seed oil: A novel perspective on lipid antioxidation

Xiaoqin Wang,María del Mar Contreras,Dunming Xu,Chen Xing,Lijuan Wang,Daomao Yang

Bound phenolic compounds have been widely investigated in food from plants, while research on vegetable oils is limited. Thus, to comparatively analyse free and bound phenolic compounds in a lipid system, different distributions of free and bound phenolic compounds were prepared by exogenous addition of chemical standards to model tea seed oil in this work. For that, the phenolic composition was quantified with UHPLC-QqQ-MS/MS, and the antioxidant capacity was evaluated by the DPPH assay and the Rancimat method. After pre-optimisation of concentrations, the results showed that the oil sample contained 12.3% bound phenolic compounds after incubation for 6 h, higher than the other samples (0, 2, 4, 8, 10 and 12 h) with equal addition. This sample also had a longer reduction time during Rancimat oxidation, corresponding to the higher total DPPH radical scavenging capacity. Further, docking, molecular dynamics and quantum mechanics analysis revealed that intermolecular forces might account for binding forms between phenolic compounds and glycerides, including hydrogen bonds and hydrophobic interactions. In addition, the structure-activity relationship of bound phenolic compounds was explored tentatively. Conclusively, bound phenolic compounds in vegetable oil, probably formed by intermolecular interactions, enhanced antioxidant capacity, a novel perspective on the antioxidation in lipids.

研究领域: 食品科学 · 脂质化学 · 植物化学
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Journal of Fungi · 2023 ·Vol. 9 ·期 2 ·237 · IF 4.7

Lignin Promotes Mycelial Growth and Accumulation of Polyphenols and Ergosterol in Lentinula edodes

Feifei Wu,Heqin Wang,Qiufeng Chen,Xiao Pang,Hao Jing,Lijun Yin,Xiuqing Zhang

It has been demonstrated that lignin was efficiently degraded byLentinula edodes(L. edodes). However, the process of lignin degradation and utilization byL. edodeshas not been discussed in detail. Therefore, the effects of lignin onL. edodesmycelium growth, chemical compositions, and phenolic profiles were investigated herein. It has been revealed that 0.10% lignin acted as the most effective concentration to accelerate mycelia growth, which yielded the highest biomass of 5.32 ± 0.07 g/L. Furthermore, a 0.10% concentration of lignin promoted the accumulation of phenolic compounds, especially protocatechuic acid, with peak value of 48.5 ± 1.2 μg/g. In contrast, the higher concentration of lignin (0.20%) exerted an inhibitory effect on the growth ofL. edodes. Overall, the application of lignin at the optimal concentration of 0.10% could not only enhance the mycelial growth but also accumulate the phenolic acids and raise the nutritional and medical values ofL. edodes.Keywords:lignin;shiitake mushroom;biomass;phenolic compound

CAS / MDL: 8061-51-6
研究领域: 真菌学 · 生物化学
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Journal of Food Measurement and Characterization · 2020 ·Vol. 15 ·期 1 ·247-255 · IF 1.648

Phenolics and ascorbic acid in pumpkin (Cucurbita maxima) slices: effects of hot air drying and degradation kinetics

Ouyang Mengyun,Cao Sheng,Huang Yiqun,Wang Yan

This study was aimed to investigate the effects of hot air drying (60–100 ℃, 1.5 m/s, 6–17 h; final products contained 10.50 ± 0.29% moisture) on the levels of total phenolic compounds (TPC) including both soluble phenolic compounds (SPC) and insoluble phenolic compounds (IPC) as well as ascorbic acid in pumpkin slices. IPC accounted for an average of 74.9% of the TPC in fresh pumpkin flesh, but only accounted for 49.4% (100 ℃ drying) to 59.7% (60 ℃ drying) of the TPC in the final dried pumpkin slices. As the drying temperature increased, the retention of IPC (22.8–42.7%), TPC (41.6–50.9%), and ascorbic acid (22.2–51.0%) in the dried products significantly decreased ( p  < 0.05), but the retention of SPC (74.5–92.7%) significantly increased which may be due to more conversion of IPC to SPC at a higher temperature. The degradation of ascorbic acid during hot air drying fitted well to the first-order kinetic function (R 2  = 0.985–0.999), and that of IPC, SPC and TPC fitted well to zero-order reactions (R 2  = 0.887–0.997). Unlike the other three compounds, the reduced level of SPC decreased as the temperature increased ( k  = 0.008–0.029/h, Ea  = 33.7 kJ/mol), corresponding to the increased retention of SPC in the final dried pumpkin slices.

CAS / MDL: 50-81-7 149-91-7
研究领域: 食品科学 · 植物化学
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RENEWABLE ENERGY · 2022 · IF 8.634

Synergetic effect between Pd clusters and oxygen vacancies in hierarchical Nb2O5 for lignin-derived phenol hydrodeoxygenation into benzene

Siteng Rong,Hongzi Tan,Zhaobin Pang,Zhiyuan Zong,Rongrong Zhao,Zhihe Li,Zhe-Ning Chen,Ning-Ning Zhang,Weiming Yi,Hongyou Cui

Lignin could be depolymerized into large amount of phenolic compounds via fast pyrolysis . The upgrade of phenolic compounds via hydrodeoxygenation (HDO) involves multiple reaction pathways. It is challenging to selectively remove the oxygen-containing groups while keeping the aromatic rings intact. In this work, hierarchical Nb 2 O 5 (H–Nb 2 O 5 ) microspheres with abundant oxygen vacancies were synthesized to anchor the Pd clusters, which is featured with strong metal-support interaction via the electron transfer between Pd species and Nb species. For phenol HDO reaction, the oxygen vacancies were prone to interact with the phenolic hydroxy groups, resulting in phenol molecule adsorbed in a “nonplanar” manner, greatly weakening the C Ar -O bonds and averting the ring hydrogenation. Besides, the activated hydrogen atoms on Pd clusters could migrate to the vicinity of oxygen vacancies via spillover, promoting the cleavage of C Ar -O bond to obtain benzene. Current work provides a deep insight into the synergetic catalytic mechanism of Pd/H–Nb 2 O 5 catalyst for phenol HDO reaction, and also sheds light on the design and synthesis of high-efficient catalysts in other heterogeneous catalysis fields.

研究领域: 催化化学 · 材料科学 · 能源化学
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MOLECULES · 2019 ·Vol. 24 ·期 23 ·4328 · IF 3.06

Simultaneous Determination of Six Compounds in Destructive Distillation Extracts of Hawthorn Seed by GC-MS and Evaluation of Their Antimicrobial Activity

Hongyu Rao,Peibo Li,Hao Wu,Chong Liu,Wei Peng,Weiwei Su

Hawthorn seed can be used to produce various bioactive compounds through destructive distillation. In this study, an accurate and feasible analytical method based on a gas chromatography mass spectrometer (GC-MS) was developed for simultaneous determination of six major compounds (contributing to more than 3% in total peak area) in destructive distillation extracts of hawthorn seed collected at different temperatures ranging from 150 to 270 °C. Then, a broth microdilution method coupled with grey correlation analysis was engaged in the evaluation of their antimicrobial activities and the screening of primarily active compounds. Results indicate that the extract collected from 211 to 230 °C had the highest content of six major compounds (furfural, 2-methoxyphenol, 2-methoxy-4-methylphenol, 4-ethyl-2-methoxyphenol, 2,6-dimethoxyphenol, and 5-tertbutylpyrogallol) and the strongest antibacterial activity. Besides, 2,6-dimethoxyphenol was found to be a potential compound in inhibiting the growth of vaginitis pathogens. This study provided an optimum temperature for the destructive distillation of hawthorn seed, reducing the waste of energy, and saving the cost of production in the hawthorn industry.Keywords:hawthorn seed;GC-MS;phenolic compounds;antimicrobial activity

研究领域: 植物化学 · 微生物学
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JOURNAL OF ORGANIC CHEMISTRY · 2019 · IF 4.745

Phosphorous Acid-Catalyzed Alkylation of Phenols with Alkenes

Shaofeng Wu,Jianyu Dong,Dan Zhou,Wan Wang,Long Liu,Yongbo Zhou

A H3PO3-catalyzed alkylation of phenols with alkenes is achieved in a facile, efficient, and selective manner. The reaction shows a unique selectivity, i.e., excellent regioselectivity, thorough suppression of overalkylation, without alkylation of a simple phenyl ring, and can selectively provide ortho-, meta-, or para-alkylated phenol derivatives in good to excellent yields. This feature along with mild reaction conditions, sensitive functional group tolerance, and scale-up synthesis and late modification of phenolic bioactive compounds make it an ideal and practical alternative for the modification of phenols.

研究领域: 有机化学 · 药物化学
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RSC Advances · 2015 ·Vol. 5 ·期 123 ·101507-101518 · IF 3.84

Phenolic profiles and antioxidant activity in four tissue fractions of whole brown rice

Huihui Ti,Jinjie Guo,Ruifen Zhang,Zhencheng Wei,Lei Liu,Yajuan Bai,Mingwei Zhang

In view of the fact that different types of processed rice contain different tissue fractions, the present study quantified free and bound phenolic profiles and antioxidant activity in the pericarp, aleurone layer, embryo and endosperm fractions of japonica and indica whole brown rice. Significant differences were found in the total phenolic content, oxygen radical absorbance capacity (ORAC) and cellular antioxidant activity (CAA) of the different fractions. The ratios of free and bound phenolics to total phenolics varied between the fractions. Thirteen individual phenolic compounds (gallic, protocatechuic, hydroxybenzoic, chlorogenic, vanillic, caffeic, syringic, isoferulic, coumaric and ferulic acids, as well as catechin, epicatechin and quercetin) were detected in both free and bound forms. The contributions of the pericarp, aleurone layer and embryo fractions to whole brown rice were 13.0%, 28.5% and 8.8% for total phenolics, 14.1%, 29.7% and 9.1% for total flavonoids, 18.2%, 38.0%, and 11.1% for total ORAC values and 14.6%, 38.0%, and 16.9% for CAA values, respectively. These findings indicate that the phenolics in brown rice can be concentrated by processing different fractions or by milling to different levels because of the uneven distribution of chemical constituents.

研究领域: 食品科学 · 植物化学
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JOURNAL OF FOOD PROCESSING AND PRESERVATION · 2022 ·Vol. 46 ·期 7 ·e16679 · IF 2.609

Effects of phenols with different structure characteristics on properties of potato starch: Action rule and molecular mechanism

Nan Chen,Zi-Jian Feng,Hao-Xiang Gao,Qiang He,Wei-Cai Zeng

Four phenols (protocatechuic acid, ellagic acid, naringin, and tannic acid), could affect the particle size and microstructures of potato starch, while the action sequence was as: tannic acid > naringin > ellagic acid > protocatechuic acid. Meanwhile, all phenols could decrease the thermal stability of potato starch and changed its crystallinity. In addition, hydrogen bonds were determined as the main molecular force between phenols and potato starch. Furthermore, molecular dynamics simulation indicated that phenols could significantly affect the spatial configuration of starch molecules by changing the formation of hydrogen bonds, and phenols with more hydroxyl groups and higher molecular weight exhibited stronger binding effects than simple phenols. All present results suggested that the hydroxyl groups amount and molecular weight of phenols could affect their effects on starch molecules, so as to significantly affected the properties of potato starch, which showed the potential application in chemical and food industries. Novelty impact statement Phenols affected the properties of potato starch and changed the spatial configuration of starch molecules by a hydrogen bond. Phenols action sequence was: tannic acid > naringin > ellagic acid > protocatechuic acid, and more hydroxyls and higher molecular weight promoted the effects of phenols on starch.

研究领域: 食品科学 · 分子生物学
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MICROCHEMICAL JOURNAL · 2025 · IF 5.1

A flower-like Cu-doped ZIF with intrinsic reference signal for ratiometric electrochemical assay of phenolic compounds

Jijun Guan,Liwei Wang,Fugang Xu,Guangran Ma

Ratiometric electrochemical probes are vital for reliable sensing but often suffer from complex preparation, reference molecule leakage, and single function. To address these limitations, this study reports a flower-like Cu-doped zeolite imidazolate framework (Zn 0.5 /Cu 0.5 /Co-ZIF) prepared at room temperature via simple stirring. This material acts as both an electrode material and a robust ratiometric probe for detecting catechol (CC) and acetaminophen (AP). Compared with pristine Zn/Co-ZIF, Cu doping confers several advantages: transforming lamellar Zn/Co-ZIF into a flower-like structure for enhanced electron and mass transfer; significantly improving redox current of CC/AP for high sensitivity; and generating a stable Cu-based redox signal as an internal reference, improving accuracy. The sensor achieved wide linear ranges (CC: 0.5–150 μM; AP: 0.2–300 μM) and low detection limits (CC: 0.12 μM; AP: 0.04 μM) for determination of phenol compounds. Compared to single-signal assay, the ratiometric approach showed lower RSDs and superior linear correlations. The sensor also achieved satisfactory simultaneous detection of CC and AP, along with accurate quantification in lake water samples. This work presents a facile strategy for a MOF based reference probe, offering a promising platform for stable and accurate ratiometric electrochemical sensors.

研究领域: 生物传感 · 分析化学 · 纳米材料 · 环境监测 · 电化学检测
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LWT-FOOD SCIENCE AND TECHNOLOGY · 2019 · IF 3.714

Phenolic profile and antioxidant activity of Chinese rice wine fermented with different rice materials and starters

Haiying Cai,Qi Zhang,Lingzhi Shen,Jie Luo,Ruiyu Zhu,Jianwei Mao,Minjie Zhao,Chenggang Cai

The polyphenolic compounds in wines are beneficial to human health. To better understand the effect of different factors on the phenolics and antioxidant activities of wine during rice wine fermentation, 6 rice materials and 7 rice wine starters from rural areas were used to ferment Chinese rice wine. The results showed that black rice and the starter O4 were preferred for the optimum polyphenolic content and antioxidant activity, respectively. In addition, the results indicated that the polyphenolics of the rice wines were mainly derived from their plant materials and that various rice materials could result in drastically different wine quality. In contrast, the total polyphenol contents could be less significantly changed by using different starters. The antioxidant activity results of these fermented wines were consistent with the results of the total polyphenol contents. The rice wines produced using 6 different rice materials were significantly different in antioxidant activity measured by ABTS and FRAP assay . Similar to the results of the total polyphenol content and the antioxidant activity, the wine samples with different rice materials showed significantly different polyphenolic profiles compared with those of the rice wine group with different starters. These results suggested that rice materials and starters have different effects on polyphenol extraction and conversion of rice wines.

研究领域: 食品科学 · 生物化学
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FOOD CHEMISTRY · 2018 · IF 4.946

Distribution and quantitative analysis of phenolic compounds in fractions of Japonica and Indica rice

Chao Ding,Qiang Liu,Peng Li,Yongsheng Pei,Tingting Tao,Yan Wang,Wei Yan,Guofeng Yang,Xiaolong Shao

Utilization of phenolic compounds in rice husk and bran is important for improving the functionality of rice by-products. Eight rice varieties planted in different area were selected to analyze the phenolic compounds distribution of fractions in Japonica and Indica rice by using UPLC-MS method. A total of 12 phenolic compounds were identified in all rice varieties. Ferulic acid, gallic acid, protocatechuic acid and syringic acid were the dominant phenolic compounds in rice bran, while p-Hydroxybenzaldehyde was the main phenolic compounds existed in rice husk (14.46–23.72 µg·g −1 ). Bran and husk fractions provide more than 90% of phenolic compounds and antioxidant activity of whole rice. Regardless of the planting environmental effects, Japonica rice has significant higher phenolic compounds and antioxidant activity than Indica rice (P < 0.05). Therefore, it can be concluded that the distribution of phenolic compounds were strongly correlated with the rice varieties and fractions.

CAS / MDL: 1898-66-4 149-91-7
研究领域: 食品科学 · 植物化学
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Foods · 2022 ·Vol. 11 ·期 9 ·1252 · IF 5.561

Evaluation of Different Black Mulberry Fruits (Morus nigra L.) Based on Phenolic Compounds and Antioxidant Activity

Ri-Si Wang,Pan-Hao Dong,Xi-Xiang Shuai,Ming-Shun Chen

This study evaluated thirteen different black mulberry fruits (Morus nigraL.) grown in the Guangdong region in order to select the best cultivar for health benefits and commercial applications. The phenolic compounds were identified and quantified using UPLC-ESI-MS/MS. The antioxidant activity was evaluated by three in vitro methods. Significant differences among samples were found regarding total soluble solids (6.20–15.83 °Brix), titratable acidity (5.82–48.49 mg CA/g), total phenolic contents (10.82–27.29 mg GAE/g), total flavonoid contents (1.21–2.86 mg RE/g) and total anthocyanin contents (2.91–11.86 mg CE/g). Fifty-five different phenolic compounds were identified, of which fifteen were reported in mulberry for the first time, but only forty-six of them were quantitated. The DPPH radical scavenging activity, ABTS radical scavenging activity and ferric ion-reducing antioxidant power varied significantly among the samples. Overall, cultivars with better combinations of phenolic compounds and antioxidant activity were Qiong46 (M-2), Yuebanguo (M-4) and Heizhenzhu (M-10), which were recommended for commercial cultivation.Keywords:mulberry fruit;cultivar;phenolic compounds;antioxidant activity

研究领域: 植物学 · 食品科学
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