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Plants-Basel · 2023 ·Vol. 12 ·期 2 ·308 · IF 4.5

Volatile Metabolome and Aroma Differences of Six Cultivars of Prunus mume Blossoms

Ting Li,Xi Zhao,Xueli Cao

Prunus mumeis a traditional Chinese plant with high ornamental and application values due to its very early blooming and unique fragrance. Long-term breeding and cultivation have resulted in a variety ofP. mumeblossoms and have made their exploitation more possible. Existing studies on the volatile metabolome and aroma ofP. mumeblossoms are limited. In this study, six extensively planted cultivars ofP. mumeblossoms, including Gulihong (GLH), Yudie (YD), LvE (LE), Dongfang Zhusha (DFZS), Jiangmei (JM), and Gongfen (GF), were investigated for their differences in terms of volatile metabolome, as well as their aroma characteristics based on the strategies and methods of metabolomics. The volatile metabolites were analyzed using HS-SPME-GC-MS technique. A total of eighty-nine compounds were detected and sixty-five of them were tentatively identified, including thirty-seven phenylpropanoids/benzenes, seventeen fatty acid derivatives, ten terpenoids, and one other compound. YD contains the most volatile metabolites in terms of number and amounts, which impart more abundant aromas to this cultivar. Fifteen differential compounds were screened through the untargeted metabolic analysis of twenty-nine samples by principal component analysis (PCA) and partial least squares-discriminant analysis (PLS-DA), while nine compounds were screened based on the odor activity value (OAV) analysis of the sixty-five identified compounds. GLH and GF, JM and LE were found to be more similar to each other based on chemometrics analysis of both volatile contents and OAVs, while YD and DFZS were markedly different from other cultivars. Six main metabolites, including benzaldehyde, methyl benzoate, benzyl acetate, eugenol, (E)-cinnamic alcohol, and 4-allylphenol, together with 2-nonenal, 3,4-dimethoxytoluene, and trans-β-Ionone were screened as differential compounds, owing to their higher contents and/or lower olfactory threshold, which endow an almond, cherry, phenolic, wintergreen, cananga odorata, floral, jasmine, hyacinth, cinnamon, clove, woody, medicinal, and violet fragrance to each variety, and greatly contribute to the aroma differences of six cultivars ofP. mumeblossom.Keywords:aroma;HS-SPME-GC-MS;Prunus mumeblossom;untargeted metabolomics;volatile metabolome

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BIOCATALYSIS AND BIOTRANSFORMATION · 2022 · IF 2.325

A chlorogenic acid esterase from a metagenomic library with unique substrate specificity and its application in caffeic and ferulic acid production from agricultural byproducts

Jian Yao,Lun Gui,Qizhang Long

Soil microbes are an abundant source of enzymes with unique properties that may be useful for industrial applications. As most wild-type strains show low chlorogenic acid esterase expression and activity, and most microbes cannot be cultured in the laboratory, a metagenomic approach provides methods of identifying new enzymes. In this study, a gene encoding a chlorogenic acid esterase, named Tan410, was isolated from a soil metagenomic library and overexpressed in Escherichia coli BL21 (DE3). The recombinant enzyme, with a predicted molecular weight of 54.88 kDa, was purified to homogeneity. The Km and Vmax values for Tan410 were 1.26 mM and 0.33 mM min–1, respectively, with chlorogenic acid as the substrate. Its optimum temperature and pH for reaction were 30 °C and 7.5, respectively. The enzyme exhibited moderate thermostability and broad pH stability (3.0–10.0). Tan410 was also able to hydrolyse ethyl ferulate, methyl caffeate, propyl gallate, ethyl gallate, methyl vanillate, methyl benzoate, ethyl benzoate, methyl 2,5-dihydroxybenzoate, and methyl 3,5-dihydroxybenzoate, and it released caffeic and ferulic acids from agricultural byproducts (destarched wheat bran and coffee pulp). Tan140 has potential for industrial application in biomass valorization.

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RENEWABLE ENERGY · 2022 · IF 8.634

Efficiently and directly produce triacetylglycerol from oils and fats over mesoporous polymeric solid acid catalysts

Lijuan Su,Xiaojie Shao,Lin Chai,Hui Ge,Hongliang Wang,Xiaojing Cui,Tiansheng Deng,Xianglin Hou

A series of mesoporous solid acid catalysts (PDS-x) with large BET surface area, superior thermal stability, strong sulfonic acid groups and tunable Brønsted acidity were synthesized by the copolymerization of divinylbenzene (DVB) and sodium p-styrenesulfonate (SPSS). The PDS-x catalysts showed high activity on the direct and efficient production of triacetylglycerol (TAG) via acyl exchange reaction of oils (fats) and acetic acid. The highest TAG yield of 93.0 mol% was obtained on the PDS-x catalysts at a mild condition of 200 °C. By combining SEM, TEM, FT-IR/DRIFTS, BET, XRD , XPS , EA, 31 P MAS NMR and TG-DTG, the key factors that affected the TAG yield were clarified on the PDS-x catalysts. Moreover, the origin of the slow deactivation on these catalysts was elucidated. The large BET surface area and abundant mesopores of catalysts allowed the contact of large-sized oils (fats) with the strong sulfonic acid groups, accounting for the high TAG yield.

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INTERNATIONAL JOURNAL OF BIOLOGICAL MACROMOLECULES · 2021 · IF 6.953

Effective removal of metal ions and cationic dyes from aqueous solution using different hydrazine–dopamine modified sodium alginate

Tianzhu Shi,Zhengfeng Xie,Zhu Zhu,Wei Shi,Yucheng Liu,Minyao Liu,Xinliang Mo

In this paper, DSA-AAD-DA and DSA-TPDH-DA were prepared to effectively remove metal ions and cationic dyes from aqueous solution. The hydrazone structure was prepared by hydrazide-modified SA which captured metal ions selectively, and the remaining functional groups were used as active adsorption sites for cationic dyes. The thermodynamic parameter for the sorption demonstrated the process is endothermic and spontaneous. In single process, the adsorption of metal ions by DSA-AAD-DA and DSA-TPDH-DA correlated well with the Freundlich model through the hydrazone structure coordination and ion exchange which was mainly chemical adsorption, and cationic dyes adsorption correlated well with the Langmuir model which was shown monolayer adsorption was dominant by hydrogen bonding, electrostatic interaction, and π-π interaction. In binary system, the mixed adsorption shown significant antagonism effect in high concentration, but cationic dyes and metal ions in low concentration were efficiently and simultaneously removed, the adsorption ability of DSA-TPDH-DA was much better than DSA-AAD-DA. Moreover, adsorption efficiency can still maintain more than 80% after five times adsorption-desorption recycle. Therefore, DSA-AAD-DA and DSA-TPDH-DA possessed great potential for wastewater treatment.

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AMB Express · 2021 ·Vol. 11 ·期 1 ·1-10 · IF 3.298

A novel esterase from a soil metagenomic library displaying a broad substrate range

Yao Jian,Gui Lun,Yin Shaocheng

A novel esterase gene was isolated from a soil metagenomic library. The gene encoded a protein of 520 amino acids which contained a 21 aa signal peptide. Primary structure analysis of the protein sequence revealed that it contained a conserved active site motif (SxSxG) and a structural motif (CS-D-HC). Then the esterase gene was cloned and expressed in Escherichia coli BL21(DE3). SDS-PAGE analysis of the purified esterase showed that it was expressed in a highly soluble form and its molecular mass was estimated to be 55 kDa. Characterization of the esterase revealed that it exhibited high activity toward p-nitrophenyl esters with short acyl chains and especially p-nitrophenyl acetate, suggesting that it was a typical carboxylesterase rather than a lipase. With p-nitrophenyl acetate as substrate, the enzyme showed its optimal activity at pH 7.0 and 30 °C, and it was stable at a broad pH range from 4.5 to 10.0 and temperature not higher than 50 °C. Furthermore, the enzyme showed different substrate specificity from known esterase, it was not only hydrolyzing against p-nitrophenyl esters, but also hydrolyzing all hydroxybenzoic esters and hydroxycinnamic ester assayed. As it was an enzyme active on a broad range of phenolic esters, simultaneously possessing feruloyl esterase, chlorogenate esterase and tannase activities, it could serve as a valuable candidate for applications in biotechnology.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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TALANTA · 2021 · IF 6.057

Preparation of functionalized graphene and ionic liquid co-doped polypyrrole solid phase microextraction coating for the detection of benzoates preservatives

Jie Du,Faqiong Zhao,Baizhao Zeng

A novel solid-phase microextraction coating based on polypyrrole (Ppy) with manganese dioxide modified 6-aminohexanoic acid functionalized graphene (MnO 2 -fGr) and 1-allyl-3-vinylimidazolium bis(trifluoromethylsulfonyl)imide ([AVIm]NTf 2 ) as dopants (Ppy/MnO 2 -fGr/[AVIm]NTf 2 ) was successfully prepared by electrochemical method. The composite coating was characterized by scanning electron microscope (SEM), Fourier infrared spectrum (FT-IR) and thermogravimetry (TG). The composite coating showed coarse structure, which could improve the specific surface area of it, and according to the TG curve, it also had good thermal stability. The composite coating was used for the headspace-solid phase microextraction (HS-SPME) and chromatographic analysis of benzoates (i.e. methyl benzoate , ethyl benzoate, propyl benzoate, butyl benzoate),by coupling with gas chromatography with hydrogen flame ionization detector (GC-FID). Under optimal conditions, their enrichment factors were 140–460, linear detection ranges were 25–60000 ng L −1 , and detection limits were 2.84–6.42 ng L −1 . The standard deviations for five consecutive extractions of 100 μg L −1 analytes were 3.00–10.20%, while the standard deviation for the extractions of 100 μg L −1 analytes with five different coatings were 5.70–13.80%. The proposed method was applied for the detection of the benzoates in cosmetics, and the recoveries for the spiked benzoates were 82.8–116.8%.

✓ 已验证 产品关联 DOI PubMed 高影响因子
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APPLIED CATALYSIS B-ENVIRONMENTAL · 2021 · IF 19.503

Biomimetic donor-acceptor motifs in carbon nitrides: Enhancing red-light photocatalytic selective oxidation by rational surface engineering

Chong Wang,Yuchen Hou,Jiajia Cheng,Mei-Jin Lin,Xinchen Wang

Oxidation, especially selective oxidation by a heterogeneous catalyst with molecular oxygen, is a core technology for the conversion of petrochemical feedstock to commodity chemicals and pharmaceuticals. Existing catalytic approaches for efficient aerobic oxidation normally rely on the engagement of organometallic centers or transition-metal nanoparticles. In light of the necessity to develop sustainable production methodologies, multiple approaches for the metal-free polymeric carbon nitride (PCN) photocatalytic selective oxidation have been evaluated. However, the insufficient visible light optical absorption, poor charge-carriers separation and the weak driving force towards oxidation reaction impart a serious restriction on the efficiency and selectivity of the organic photosynthesis, especially under extended wavelength solar light irradiation. Here, we report a surface engineering photochemical modification method to fabricate a donor-acceptor (D-A) functional carbon nitride photocatalyst (ECN) under ambient conditions. The well-developed d -A structure, preserved high crystallinity and enlarged π-conjugation framework of the hybrid semiconductor-molecule ECN samples favor the improvement of the optical absorption, as well as the enhanced separation and migration of the photo-generated charge carriers. As a result, the obtained ECN photocatalysts exhibited remarkable enhancement in the photocatalytic aerobic oxidation of alcohols, even under an extended light wavelength of 620 nm red-light irradiation. The photocatalytic aerobic sulfides and sp 3 C–H oxidation reactions were also considerably accelerated over ECN and may serve as a direct approach for the construction of value-added sulfoxide and ketone products.

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JOURNAL OF FOOD SCIENCE · 2021 ·Vol. 86 ·期 5 ·1714-1725 · IF 3.167

Enzymatic acylation of rutin with benzoic acid ester and lipophilic, antiradical, and antiproliferative properties of the acylated derivatives

Hai-Mei Li,Ting-Ting Xu,Qing-Xia Peng,Yong-Sheng Chen,Hua Zhou,Yu-Yun Lu,Ri-An Yan

Rutin (3′,4′,5,7-tetrahydroxy-flavone-3-rutinoside) was enzymatically acylated with benzoic acid and its esters (methyl benzoate and vinyl benzoate) using Thermomyces lanuginosus lipase (Lipozyme TLIM). The acylation reaction was optimized by varying the reaction medium, reaction temperature, acyl donor, substrate molar ratio, and reaction time. The highest conversion yield (76%) was obtained in tert -amyl alcohol (60 °C, 72 hr) using vinyl benzoate (molar ratio of 1:10) as acyl donor. The acylation occurred at the 2′′′-OH and 4′′′-OH of the rhamnose unit and the 2′′-OH position of the glucose moieties. Three novel rutin acylated derivatives (compounds 1 – 3 ) were purified and characterized by HR-MS and 1D and 2D NMR spectroscopy. We found that acylation significantly improved lipophilicity, capacity to inhibit lipid peroxidation, anticancer capacity and substantially maintained the antioxidant activity of rutin. This research provides important insights in the acylation of flavonoids with different glycosyl moieties. Practical Application In this study, three novel rutin derivatives were successfully synthesized and the highest conversion yield (76%) was obtained by reacting the rutin and vinyl benzoate at molar ratio of 1:10 in tert -amyl alcohol for 72 hr at 60 °C. Introducing a benzoic acid substituent into rutin molecule significantly improved their lipophilicity and inhibition of lipid peroxidation in lipophilic system. Furthermore, this study demonstrated that acylation significantly improved anticancer capacity and substantially maintained the antioxidant activity.

CAS / MDL: 65-85-0 93-58-3
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JOURNAL OF SOLUTION CHEMISTRY · 2020 ·Vol. 49 ·期 11 ·1402-1418 · IF 1.273

Investigation of the Effect of Alkyl Chain Length on Molecular Interactions Between Methyl Benzoate with Alcohols: A Study of Physicochemical Properties

Chen Tingting,Feng Xiao,Yin Yuqiao,Xu Yingjie

Densities, speeds of sound, and viscosities of binary mixtures of methyl benzoate (MB) with ethanol, 1-propanol, and 1-butanol were measured at temperature ranging from T  = 293.2 to 313.2 K and refractive indices were determined at T  = 303.2 K. Excess molar volumes, V E , isentropic compressibility deviations ∆ κ s and viscosity deviations, Δ η , were obtained and fitted with the Redlich–Kister equation with satisfactory results. Based on the measured and derived physicochemical properties, the influence of the alkyl chain length of the alcohol on the molecular interactions of the studied mixtures was explored. The results show that both hydrogen bond interaction between carbonyl group of MB and hydroxyl group of alcohol and the packing efficiency, such as accommodation of alcohol in the interstice of MB, play an important role in the microstructure of the mixtures, which leads to the disruption of alcohol with the addition of MB. Moreover, by comparing V E , ∆ κ s and Δ η values of MB (1) + alcohol (2) systems at T  = 303.2 K, it is found that the strength of hydrogen bond interaction and the packing efficiency significantly weakens with increasing alkyl chain length of alcohol in going from ethanol to 1-butanol, resulting in the V E values of the studied systems gradually changing from a negative deviation to an S shape, the ∆ κ s and Δ η values have negative deviations, and the ∆ n D values have positive deviations. The obtained results will provide thermodynamic guidance for the industrial purification of methyl benzoate.

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JOURNAL OF MOLECULAR LIQUIDS · 2020 · IF 5.065

A detail study of the microstructure of methyl benzoate/methanol mixture proved by IR spectra, excess infrared wavenumber, and physicochemical properties

Xiao Feng,Tingting Chen,Yuqiao Yin,Yingjie Xu

By a comparative study of the concentration-dependent IR spectra of methyl benzoate (MB)/methanol- d 4 and MB/ n -hexane mixtures, it is found that the infrared wavenumber ( υ ˜ ) of ester group (O C O) of MB in the former system decreased exponentially with the increase of mole fraction of MB ( x 1 ), while that of the latter system decreased linearly, suggesting that H-bonding interaction plays an important role in the microstructure of MB/methanol- d 4 mixture. Therefore, to explore the microstructure and characterize the strength of H-bonding interaction of MB/methanol mixture, the excess infrared wavenumber of a group ( υ ˜ group E ) is proposed, showing that υ ˜ O − D E of methanol- d 4 presents an S shape with a minimum value at x 1  ≈ 0.4 and a maximum value at x 1  ≈ 0.8, respectively. Furthermore, the absolute value of υ ˜ O − D E (| υ ˜ O − D E |) of the former is greater than that of the latter, suggesting that H-bonding interaction in methanol- d 4 molecules is stronger than that between methanol- d 4 and MB. While both υ ˜ C = O E and υ ˜ C − O E of MB show a negative deviation with minimum values at x 1  ≈ 0.4, and | υ ˜ C = O E | is larger than | υ ˜ C − O E |, indicating that C O is directly involved in H-bonding interaction with O D, resulting in the change of υ ˜ C − O E through the electronic conjugation effect. To confirm the microstructure obtained from IR spectra, densities, speeds of sound , and viscosities of MB/methanol mixture are measured and excess properties are calculated. The results show that both excess molar volumes and isentropic compressibility deviations have a negative deviation with a minimum value at x 1  ≈ 0.4, which is good consistent with x 1 corresponding to the minimum value of υ ˜ O − D E , υ ˜ C = O E , and υ ˜ C − O E , respectively. Moreover, viscosity deviations exhibit a negative deviation with a minimum value at x 1  ≈ 0.8, which is good consistent with x 1 corresponding to the maximum value of υ ˜ O − D E .

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JOURNAL OF ASIA-PACIFIC ENTOMOLOGY · 2020 · IF 1.101

Development of lady beetle attractants from floral volatiles and other semiochemicals for the biological control of aphids

Jinhao Zhao,Zhongyan Wang,Zhongshan Li,Jiayu Shi,Ling Meng,Guorong Wang,Jingli Cheng,Yongjun Du

Aphids are among the most destructive phytophagous pests of host plants, because of their rapid reproduction, parthenogenesis, extensive crop damage, and the transmission of many plant viruses. Since lady beetles are important predatory natural enemies of aphids, developing lady beetle attractants to increase their field abundance is vital for aphid control. Floral volatiles and other semiochemicals are reportedly attractive to lady beetles. In this research, a total of 58 floral volatiles were tested by Y-tube olfactometer assays, among which 29 were highly attractive to both Harmonia axyridis (Coleoptera: Coccinellidae) and Coccinella septempunctata (Coleoptera: Coccinellidae). Meanwhile, the results of wind tunnel trials showed that only isoamyl acetate, α -humulene, trans -3-hexen-1-ol, methyl salicylate, and β -pinene lure these two species. Thereafter, 15 semiochemicals from pests, natural enemies, and pest-infested crops were mixed with the selected floral volatiles, to determine optimum formulations for attracting lady beetles through wind tunnels and further field trials. Eventually, formulas (1) α -humulene: β -pinene: methyl salicylate: trans -3-hexen-1-ol = 1:3:3:10; (5) α -humulene: β -pinene: methyl salicylate:1-nonanal = 1:3:3:10; (8) α -humulene: β -pinene: methyl salicylate: indole = 1:3:3:10 ( 1 , 5 , and 8 are labels used for the various formulations in field trials) were successfully verified to be attractive to lady beetles in both pumpkin and wheat fields. These formulations will be of great significance in developing integrated pest management strategies for aphid control.

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APPLIED CATALYSIS B-ENVIRONMENTAL · 2019 · IF 14.229

C60 Fullerol promoted Fe(III)/H2O2 Fenton oxidation: Role of photosensitive Fe(III)-Fullerol complex

Peng Zhou,Jing Zhang,Zhaokun Xiong,Yang Liu,Xiaowei Huo,Xin Cheng,Wenshu Li,Feng Cheng,Yongli Zhang

Hydroxylated C 60 Fullerene (Fullerol) induced photochemical production of reactive oxygen species (ROS, e.g. singlet oxygen ( 1 O 2 ) and hydroxyl radical ( OH)) is a slow process, and the role of its surface groups other than high water-solubility is still lack of investigation. In this study, we demonstrate Fullerol can promote Fe(III)/Fe(II) cycles to degrade dimethyl phthalate (DMP) in Fe(III)/H 2 O 2 Fenton system as both an electron donor and an electron-transfer mediator. At acidic condition, the formation of carbonyl and carboxyl via pinacol rearrangement and subsequent keto-enol isomerization can produce cage-opened structure of Fullerol, resulting in the pH-dependent formation of Fe(III)-Fullerol complex. Two pathways of Fe(II) recovery via intramolecular electron transfer of Fe(III)-Fullerol complex to enhance Fe(III)/H 2 O 2 Fenton oxidation were proposed: 1) Fullerol direct reduces Fe(III) into Fe(II) as an electron donor in dark, and it was strongly enhanced under visible light irradiation; 2) Fullerol mediates electron transfer from electron donor (e.g. hydrogen peroxide and organics) to Fe(III) in visible light condition. Furthermore, DMP degradation pathway was proposed based on variation of main intermediates.

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