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FOOD CHEMISTRY · 2018 · IF 4.946

The AP2/ERF transcription factor SmERF1L1 regulates the biosynthesis of tanshinones and phenolic acids in Salvia miltiorrhiza

Qiang Huang,Meihong Sun,Tingpan Yuan,Yu Wang,Min Shi,Sunjie Lu,Boping Tang,Jingxian Pan,Yao Wang,Guoyin Kai

Tanshinones and phenolic acids are two important metabolites synthesized by the traditional Chinese medicinal plant Salvia miltiorrhiza . There is increasing market demand for these compounds. Here, we isolated and functionally characterized SmERF1L1 , a novel JA (Jasmonic acid)-responsive gene encoding AP2/ERF transcription factor, from Salvia miltiorrhiza . SmERF1L1 was responsive to methyl jasmonate (MJ), yeast extraction (YE), salicylic acid (SA) and ethylene treatments. Subcellular localization assay indicated that SmERF1L1 located in the nucleus. Overexpression of SmERF1L1 significantly increased tanshinones production in transgenic S. miltiorrhiza hairy roots by comprehensively upregulating tanshinone biosynthetic pathway genes, especially SmDXR . Yeast one-hybrid (Y1H) and electrophoretic mobility shift assay (EMSA) showed that SmERF1L1 binds to the GCC-box of SmDXR promoter while dual luciferase (Dual-LUC) assay showed that SmERF1L1 positively regulated the expression of SmDXR . Our study suggested that the SmERF1L1 may be a good potential target for further metabolic engineering of bioactive component biosynthesis in S. miltiorrhiza .

研究领域: 植物学 · 药用植物学 · 分子生物学
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FOOD CHEMISTRY · 2017 · IF 4.529

Interaction of phenolic acids with trypsin: Experimental and molecular modeling studies

Benguo Liu,Huizhi Xiao,Jiaqi Li,Sheng Geng,Hanjun Ma,Guizhao Liang

Trypsin is a kind of protease for digestion and food processing, whose activity can be inhibited by phenolic acids in plant foods. However, most reports explained the inhibitory difference of phenolic acids based on the number and position of substituent groups, which failed to reveal the comprehensive inhibitory mechanism. In this work, the inhibitory effects of 11 common phenolic acids on trypsin were investigated. Amongst the tested cinnamic and benzoic acid derivatives, caffeic acid and gallic acid showed the strongest anti-trypsin activity with a noncompetitive inhibition pattern, respectively. The fluorescence analysis displayed that both the quenching rate constant (K q ) and binding constant (K A ) of caffeic acid were higher than those of gallic acid. Molecular docking illustrated their different binding modes with trypsin. The ONIOM calculations revealed that the binding capacity of caffeic acid was higher than that of gallic acid, which could explain their difference in their inhibitory behaviors.

研究领域: 食品科学 · 生物化学 · 分子生物学
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Food Science & Nutrition · 2020 ·Vol. 8 ·期 7 ·3234-3242 · IF 1.797

Copigmentation effect of three phenolic acids on color and thermal stability of Chinese bayberry anthocyanins

Yanyun Zhu,Hongji Chen,Leyan Lou,Yixin Chen,Xingqian Ye,Jianchu Chen

The copigmentation effects of three phenolic acids (ferulic acid, sinapic acid, and syringic acid) on the color and thermal stability of Chinese bayberry anthocyanins were investigated. The three copigments of ferulic acid, sinapic acid, and syringic acid were found to have significant effects on the color enhancement of bayberry anthocyanins ( p < .05). The maximum absorption wavelength of the anthocyanin aqueous solution exhibited a bathochromic shift, L * decreased, and a * increased with the increase in the molar ratio of copigments. The thermal stability of bayberry anthocyanins was significantly improved after copigmentation. No new anthocyanin derivatives appeared after copigmentation. The thermodynamic parameters (Δ G , Δ H , Δ S ) of the three processes were all negative, indicating the three copigmentations were generally spontaneous and exothermic. The equilibrium constant ( K ) of the sinapic acid group was the greatest among the three phenolic acids, indicating that sinapic acid was more effective in stabilizing the anthocyanins.

研究领域: 食品科学 · 植物化学
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JOURNAL OF POLYMER SCIENCE · 2021 ·Vol. 59 ·期 18 ·2057-2068 · IF 0

The chemical effect of furfuryl amide on the enhanced performance of the diphenolic acid derived bio-polybenzoxazine resin

Zizhao Qian,Qing Li,Lujie Wang,Feiya Fu,Xiangdong Liu

As a renewable chemical, diphenolic acid (DPA) has attracted immense interest in bio-based polymer science. However, its application for polybenzoxazines is limited due to decarboxylation, that is, the release of CO 2 during the curing reaction of benzoxazine. In this study, the amidation strategy of converting DPA to diphenolic amides (DPAM) was demonstrated to solve this problem while simultaneously improving the thermal properties of polybenzoxazine. DPA was amidated by separately using four amines (hexamine, cyclohexylamine, furfurylamine, and aniline), then reacted with furfurylamine and paraformaldehyde to synthesize their benzoxazine monomers. By using TGA and DMA, all amide-containing polybenzoxazines were found to exhibit excellent thermal stabilities. Among all of the benzoxazine resins, poly(DFA-fa), which was obtained from amidation with furfurylamine, exhibited the highest glass transition temperature ( T g ) of 310°C and a decomposition temperature ( T d10 ) of 406°C. Furthermore, a possible post-curing reaction mechanism was proposed to explain the outstanding thermal performance of poly(DFA-fa) resin. This study proposes an innovative strategy to solve the decarboxylation of DPA-based polymers, which is of significance for high-performance bio-based polymers. Graphical

研究领域: 材料科学 · 高分子化学
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CHEMICAL ENGINEERING JOURNAL · 2022 · IF 16.744

Bio-based epoxy resins derived from diphenolic acid via amidation showing enhanced performance and unexpected autocatalytic effect on curing

Zizhao Qian,Yuanxiang Xiao,Xujun Zhang,Qing Li,Lujie Wang,Feiya Fu,Hongyan Diao,Xiangdong Liu

Bisphenol A (BPA) is the main precursor in the synthesis of epoxy resins. However, because of its toxic and nonrenewable nature, BPA is unsuitable in the sustainable preparation of epoxy resins. In contrast, Diphenolic acid (DPA) is renewable but its carboxyl group limits its applications in bio-based thermosets. In this study, we report a novel amidation route to tailor DPA to produce epoxide monomers that present epoxy resins with a high performance. The diphenolic amides exhibited very low toxicities when compared with that of BPA, and also provided an unexpected autocatalytic effect on the curing reactions when succinic anhydride (SA) was used as the hardener. Dynamic mechanical analyses (DMA) and tensile test results confirmed the remarkable thermomechanical properties of the cured epoxy resins, which may be attributed to the increased cross-linking density and enhanced hydrogen bonding by the amide groups. Among the SA-cured epoxy resins, diglycidyl ether of diphenolic ethylamide exhibited the best performance, which included a high T g of 114 °C, char yield (CY) of 20%, tensile strength of 60.2 MPa, and toughness value of 185 MPa. In addition, the DPA-derived epoxy resins have great potential in the preparation of bio-based composites because they act as excellent interfaces between the resin and cotton fibers (CoFs). Our study presents a new strategy to prepare bio-based epoxy resins with a high performance, emphasizing the greater potential of amidated DPA derivatives to replace BPA in the epoxy resin market.

研究领域: 材料科学 · 化学工程 · 可再生资源利用
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Catalysts · 2025 ·Vol. 15 ·期 3 ·210 · IF 4

Phenolic Acid Decarboxylase for Carbon Dioxide Fixation: Mining, Biochemical Characterization, and Regioselective Enzymatic β-carboxylation of para-hydroxystyrene Derivatives

Jie Chen,Shirong Wang,Junru Zhou,Jiaxing Xu,Bin Wu,Zhen Gao,Bingfang He

The use of CO2as a C1 carbon source for the synthesis of valuable chemicals through biotechnology methods represents an effective strategy to fix carbon dioxide. Phenolic acid decarboxylases possess the capability to introduce a carboxyl group intopara-hydroxystyrenes for the regionally selective synthesis of (E)-para-hydroxycinnamic acids, utilizing bicarbonate as a CO2source. It is difficult to achieve this reaction with traditional chemical methods, and only a few enzymes have been isolated and characterized. Here, we mined which low amino acid sequence shared its identity with those of related decarboxylases and which heterologously expressed phenolic acid decarboxylase PAD_Cs fromClostridiumsp. DSM 8431 inE. coli. The recombinant PAD_Cs displayed maximum activity at 50 °C, and pH 5.0. PAD_Cs showed distinct carboxylation ability. The carboxylated substrates have a wide range of substitution modes on aromatic systems, including alkyl and alkoxy groups as well as halogens. Furthermore, the carboxylation conversion rates were impressive:para-hydroxystyrene exceeded 20% and 2-methoxy-4-vinylphenol surpassed 26%. This study indicated that PAD_Cs might serve as a potential enzyme source in biotechnological CO2fixation.

研究领域: 生物化学 · 环境科学 · 合成生物学
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POLYMER DEGRADATION AND STABILITY · 2020 · IF 4.032

A DOPO-based phosphorus-nitrogen flame retardant bio-based epoxy resin from diphenolic acid: Synthesis, flame-retardant behavior and mechanism

Zhiyuan Chi,Zongwei Guo,Zice Xu,Mengjie Zhang,Ming Li,Lei Shang,Yuhui Ao

Searching a renewable and flame-retardant alternative to bisphenol A epoxy resins is a necessary development trend. Diphenolic acid , a plant derivative, has been proven to be one of the sustainable alternatives to bisphenol A. However, how to impart the flame-retardant property to diphenolic acid thermosets is still a challenge to synthesize high performance intrinsic flame-retardant bio-based epoxy resins. A flame-retardant bio-based epoxy resin (TEBA) was designed and synthesized via a three-step synthetic pathway from 9,10-dihydro-9-oxa-10-phosphaphenanthrene-10-oxide (DOPO)、diethanolamine and diphenolic acid (DPA). The chemical structures of the intermediate and final products were confirmed by 1 HNMR and FTIR spectroscopy. TEBA cured with 4,4′-diaminodiphenylmethane (DDM) curing agent was compared with a standard bisphenol A epoxy resin (DGEBA). Due to the combination of phosphorus and nitrogen in the main chain, the TEBA-DDM shows superior flame retardancy. Compared with DGEBA-DDM, LOI of TEBA-DDM increased from 25.8% to 42.3%, UL-94 test rating from no rating to V-0 rating, self-extinguishing within 3s. The peak heat release rate (PHRR) in the cone calorimetry test decreased by 67%. total heat release (THR) and total smoke generation (TSP) decreased by 27% and 35%, respectively. In addition, the flame retardant mechanism of TEBA epoxy thermosets was researched by FTIR, residual char photograph, SEM, TG-IR analysis and Raman spectroscopy . Meanwhile, TEBA-DDM and DGEBA-DDM have comparable mechanical properties .

研究领域: 材料科学 · 化学工程 · 高分子科学 · 可持续化学
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LANGMUIR · 2024 · IF 3.7

Fine-Tuning Electron–Donor Capability in the Basic Anion of Poly(ionic liquid) Frameworks for Revolutionizing Catalytic Synthesis of Ethyl Methyl Carbonate with Both Ultrahigh Catalytic Activity and Selectivity

Jie Chen,Huiyao Huang,Wangquan Gong,Yi Chen,Rong Dong,Limei Ren,Ting Qiu

Ethyl methyl carbonate (EMC) is a crucial solvent extensively utilized in lithium-ion battery electrolytes; the transesterification of dimethyl carbonate (DMC) with ethanol is a pivotal reaction for EMC production. However, this reaction faces challenges due to the trade-off between catalytic activity and selectivity from the basic catalysts. In this issue, we report an innovative strategy through fine-tuning the electron-donor capability of the basic phenolate anion ([PhO]) in a novel poly(ionic liquid) (PIL) framework, as synthesized via an alkylation reaction between 1,3,5-tris(bromomethyl)benzene, biphenyldiimidazole, and N,N′-carbonyldiimidazole (CDI) to trigger targeted basicity that can directionally catalyze the transesterification of DMC with ethanol, so as to achieve both ultrahigh catalytic activity and selectivity toward EMC. By varying the substituent groups with electron-withdrawing and electron-donating effects on the phenolate anion, the PILs show expected changes in the catalytic performance, following well with the trend of charge density on these substituted phenolate anions. The optimized catalyst [CPIL-CDI][MeOPhO], induced by p-methoxyphenolate anions, allows an extraordinary EMC yield of 72.19% and an EMC selectivity of 91.48% under mild conditions without any process intensifications, suppressing all of the reported catalysts reported to date. Outcomes and approaches shown in this work have the potential to expedite the systematic design of cations and anions within PILs for industrial-scale EMC production through environmentally friendly transesterification processes.

研究领域: 化学 · 材料科学 · 催化 · 能源存储
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