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DHP
MOLECULES · 2021 ·Vol. 26 ·期 19 ·5740 · IF 4.412

Elucidation of the Structure of Lignin–Carbohydrate Complexes in Ginkgo CW-DHP by 13C-2H Dual Isotope Tracer

Kai Zhang,Yanchao Liu,Sheng Cui,Yimin Xie

To elucidate the chemical linkages between lignin and carbohydrates in ginkgo cell walls,13C-2H-enriched cell wall-dehydrogenation polymers (CW-DHP) were selectively prepared with cambial tissue fromGinkgo bilobaL. by feeding D-glucose-[6-2H2], coniferin-[α-13C], and phenylalanine ammonia-lyase (PAL) inhibitor. The abundant detection of13C and2H confirmed that D-glucose-[6-2H2] and coniferin-[α-13C] were involved in the normal metabolism of ginkgo cambial cells that had been effectively labelled with dual isotopes. In the ginkgo CW-DHP, ketal and ether linkages were formed between the C-α of lignin side chains and carbohydrates, as revealed by solid state CP/MAS13C-NMR differential spectroscopy. Furthermore, the DMSO/TBAH ionic liquids system was used to fractionate the ball-milled CW-DHP into three lignin-carbohydrate complex (LCC) fractions: glucan–lignin complex (GL), glucomannan–lignin complex (GML), and xylan–lignin complex (XL). The XRD determination indicated that the cellulose type I of the GL was converted into cellulose type II during the separation process. The molecular weight was in the order of Ac-GL > Ac-GML > XL. The13C-NMR and1H-NMR differential spectroscopy of13C-2H-enriched GL fraction indicated that lignin was linked with cellulose C-6 by benzyl ether linkages. It was also found that there were benzyl ether linkages between the lignin side chain C-α and glucomannan C-6 in the13C-2H-enriched GML fraction. The formation of ketal linkages between the C-α of lignin and xylan was confirmed in the13C-2H-enriched XL fraction.Keywords:lignin–carbohydrate complexes;CW-DHP;isotope labelling;ginkgo;NMR

CAS / MDL: 9012-54-8
研究领域: 植物科学 · 化学 · 生物技术
✓ 已验证 产品关联 DOI PubMed 高影响因子
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Polymers · 2024 ·Vol. 16 ·期 22 ·3139 · IF 4.7

Thermal Condensation of Dehydrogenation Polymer (DHP) with Xylose

Peng Wang,Jiaju Xie,Wenyao Peng,Junxian Xie,Junjian An,Guangyan Zhang,Junjun Chen

Conventional adhesives used in wood-based panels typically contain volatile organic compounds, including formaldehyde, which can potentially lower indoor air quality and damage human health. Lignin, a natural adhesive present in wood, offers significant advantages over other materials due to its ready availability, renewable nature, rich aromatic rings, and aliphatic and aromatic hydroxyl groups, as well as quinone groups. However, when modified as an adhesive for wood-based panels, lignin suffers from poor water resistance and formaldehyde release. Dehydrogenation polymer (DHP), as a lignin model compound, possesses a structure similar to lignin and excellent water resistance, making it a potential substitute for lignin as a formaldehyde-free adhesive. A DHP-xylose complex was obtained from a condensation reaction between DHP and xylose in hemicellulose in a simulated hot-pressing environment. The feasibility of DHP bonding with hemicellulose components was verified using FT-IR and NMR spectroscopic methods. In addition, the structure of the adduct and condensation process were also studied. DHP and xylose underwent condensation under simulated hot-pressing conditions. Xylose and DHP may be linked by C-C bonds. The thermal condensation of DHP with xylose was investigated. This may contribute to a better understanding of the adhesive bonding process for xylose during hot-pressing and offer support for practical applications.

CAS / MDL: 25990-60-7
研究领域: 林产化学 · 生物质材料 · 木材科学与技术
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INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES · 2024 ·Vol. 25 ·期 19 ·10533 · IF 4.9

Study on the Thermal Condensation Mechanism of Dehydrogenated Polymer (DHP) and Glucuronic Acid

Peng Wang,Xu Zhang,Wenyao Peng,Junjun Chen,Junjian An,Guangyan Zhang,Junxian Xie

The preparation of traditional wood-based panels mostly uses adhesives such as urea-formaldehyde resin and phenolic resin, which not only consumes petrochemical resources but also releases formaldehyde, posing potential health risks to the human body. Lignin, a natural adhesive in plant cells, is characterized by high reactivity, and it is expected to aid in the development of a new generation of green formaldehyde-free adhesives. However, current studies of lignin adhesives have revealed that while strides have been made in reducing formaldehyde emissions, its residual presence remains a concern, an issue which is compounded by inadequate water resistance. Dehydrogenated Polymer (DHP) has a lignin-like structure and good water resistance, offering a new option for the development of formaldehyde-free adhesives. In this paper, DHP and glucuronic acid were reacted with each other in a simulated hot-pressing environment to obtain DHP-glucuronic acid complex, and then the structure of the complex was characterized by infrared nuclear magnetic resonance to verify whether DHP can be efficiently connected with hemicellulose components under hot-pressing conditions. The results showed that the thermal condensation reaction of DHP and glucuronic acid can generate ester bonds at the Cα position in a simulated hot-pressing environment. This paper explores the thermal condensation mechanism of DHP and glucuronic acid, which is helpful for understanding the bonding process between adhesives and components of wood-based panels in the hot-pressing process, and provides key theoretical support for the design of more sustainable lignin adhesives.

CAS / MDL: 6556-12-3
研究领域: 林产化学 · 绿色材料科学 · 生物质利用
✓ 已验证 产品关联 DOI PubMed 高影响因子
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FISH & SHELLFISH IMMUNOLOGY · 2023 · IF 4.7

Preparation, identification, and application of PEG/ZIF-8@ Dendrobium huoshanense polysaccharide as an adjuvant to enhance immune responses

Zhiqiang Zhang,Li Wang,Dai Zeng,Xia Ma,Hui Wang

Zeolitic imidazolate framework-8 (ZIF-8) nanoparticles loaded with polysaccharides are excellent drug-delivery carriers with high loading capacity and pH sensitivity. This study describes the one-step encapsulation of Dendrobium huoshanense polysaccharides (DHP) in ZIF-8. The resultant PEG6000/ZIF-8@DHP complex exhibited drug release properties in acidic microenvironments, possessed water solubility, demonstrated high drug loading capacity, and displayed effective encapsulation. The effects of PEG6000/ZIF-8@ DHP administration on immunoregulation, antioxidant activities, and resistance against Aeromonas veronii in channel catfish were assessed. The study revealed that the PEG6000/ZIF-8@DHP complex stimulated cellular proliferation and phagocytosis, while also inducing the production of cytokines and nitric oxide. Additionally, the complex exhibited improved antioxidant properties and increased serum lysozyme and alkaline phosphatase activities. PEG6000/ZIF-8@DHP exhibited efficacy in vivo against Aeromonas veronii infection. These results indicate that PEG6000/ZIF-8@DHP is an efficient immunostimulant and vaccine adjuvant for enhancing immunity in channel catfish.

CAS / MDL: 693-98-1 10196-18-6
研究领域: 纳米技术 · 免疫学 · 水产养殖 · 药剂学
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MACROMOLECULES · 2025 · IF 5.2

Revisiting the Classical Multicomponent Hantzsch Reaction to Form Fluorescent Dextran Hydrogels with Antibacterial Activity

Jingqin Yang,Yanchi Liu,Chunfeng Yin,Yuqi Lu,Yu Du,Chengxiao Wang,Shaoyun Shan,Hongying Su

There has been considerable interest in developing hydrogels derived from natural polysaccharides that combine controllable luminescent properties, enhanced functionality, and inherent biocompatibility. Herein, the classical multicomponent Hantzsch reaction was explored to fabricate luminescent dextran-based hydrogels with antibacterial activity. This reaction facilitates the formation of 1,4-dihydropyridine (DHP) derivatives from cross-linking of acetoacetylated dextran, aldehyde, and NH4OAc. Both low molecular weight aldehydes (formaldehyde and glutaraldehyde) and polyaldehyde (oxidized dextran) have been successfully applied in the Hantzsch cross-linking strategy, resulting in a series of intrinsically luminescent hydrogels (DHPD) with tunable gelation kinetic, mechanical properties, and operating windows. The DHPD hydrogels exhibited superior antibacterial activity, achieving an antimicrobial rate of over 90% against Gram-negative bacteria (Escherichia coli). Notably, significantly promoted wound healing and anti-inflammation effects were achieved in E. coli-infected wound models by the DHPD-F2 hydrogel dressing. Therefore, the Hantzsch cross-linking strategy provides a robust platform for the fabrication of photoluminescent dextran hydrogels, offering promising potential for advanced antibacterial wound dressing applications.

研究领域: 材料科学 · 高分子化学 · 生物医学工程 · 抗菌治疗 · 伤口愈合研究
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DYES AND PIGMENTS · 2018 · IF 3.767

A water-soluble fluorescent probe for the sensitive detection of endogenous alkaline phosphatase in living cells

Longbin Xu,Xu He,Pinyi Ma,Xin Liu,Fangmei Zhang,Ying Sun,Daqian Song,Xinghua Wang

Alkaline phosphatase (ALP) is an essential enzyme in various tissues, which has been reported to be extensively involved in various physiological and pathological processes. Fluorescent probe assays carried out in vivo are desirable for monitoring the ALP activity. In this study, a novel red-light fluorescent DHP probe, which exhibited good selectivity and high sensitivity, for monitoring the ALP activity in real time was described. The DHP probe exhibited good water solubility, and the detection limit of ALP was determined as 0.031 U/L; this value is almost less than those of the other probes reported previously. The probe exhibited high selectivity, which will not interfere with various enzymes and amino acids. Moreover, the sensing and luminescence mechanisms of ALP to DHP was investigated by density functional theory (DFT) and time-dependent DFT. Furthermore, the DHP probe was applied for the detection of endogenous ALP in BEL-7402 cells, and the fluctuation of the ALP levels in BEL-7402 and HEK 293  T cells was successfully tracked by fluorescence microscopy .

研究领域: 生物化学 · 细胞生物学 · 分子生物学 · 分析化学
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eLife · 2022 · IF 8.713

Augmentation of progestin signaling rescues testis organization and spermatogenesis in zebrafish with the depletion of androgen signaling

Gang Zhai,Tingting Shu,Guangqing Yu,Haipei Tang,Chuang Shi,Jingyi Jia,Qiyong Lou,Xiangyan Dai,Xia Jin,Jiangyan He,Wuhan Xiao,Xiaochun Liu,Zhan Yin

Disruption of androgen signaling is known to cause testicular malformation and defective spermatogenesis in zebrafish. However, knockout of cyp17a1, a key enzyme responsible for the androgen synthesis, in ar-/- male zebrafish paradoxically causes testicular hypertrophy and enhanced spermatogenesis. Because Cyp17a1 plays key roles in hydroxylation of pregnenolone and progesterone (P4), and converts 17α-hydroxypregnenolone to dehydroepiandrosterone and 17α-hydroxyprogesterone to androstenedione, we hypothesize that the unexpected phenotype in cyp17a1-/-;androgen receptor (ar)-/- zebrafish may be mediated through an augmentation of progestin/nuclear progestin receptor (nPgr) signaling. In support of this hypothesis, we show that knockout of cyp17a1 leads to accumulation of 17α,20β-dihydroxy-4-pregnen-3-one (DHP) and P4. Further, administration of progestin, a synthetic DHP mimetic, is sufficient to rescue testicular development and spermatogenesis in ar-/- zebrafish, whereas knockout of npgr abolishes the rescue effect of cyp17a1-/- in the cyp17a1-/-;ar-/- double mutant. Analyses of the transcriptomes among the mutants with defective testicular organization and spermatogenesis (ar-/-, ar-/-;npgr-/- and cyp17a-/-;ar-/-;npgr-/-), those with normal phenotype (control and cyp17a1-/-), and rescued phenotype (cyp17a1-/-;ar-/-) reveal a common link between a downregulated expression of insl3 and its related downstream genes in cyp17a-/-;ar-/-;npgr-/- zebrafish. Taken together, our data suggest that genetic or pharmacological augmentation of the progestin/nPgr pathway is sufficient to restore testis organization and spermatogenesis in zebrafish with the depletion of androgen signaling.

CAS / MDL: 57-83-0
研究领域: 生物学 · 生殖生物学 · 内分泌学 · 遗传学
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ANALYST · 2018 ·Vol. 144 ·期 2 ·536-542 · IF 3.864

Two aggregation-induced emission (AIE)-active reaction-type probes: for real-time detecting and imaging of superoxide anions

Hengchang Ma,Manyi Yang,Shaoxiong Zhang,Pei Yin,Tao Wang,Yuan Yang,Ziqiang Lei,Yucheng Ma,Yanfang Qin,Zengming Yang

Fluorescent probes are powerful tools for investigating reactive oxygen species (ROS) in living organisms. The overproduced “primary” ROS of superoxide anions (O2˙−) cause a chain of oxidative damage. In order to monitor O2˙− level fluctuations in living cells, we synthesized two reaction-type probes of TPA-DHP-1,2,3 and TPA-PPA-1,2,3, which were composed of an electron-rich triphenylamine (TPA) and the very active functional groups of dihydropyridine (DHP) and pyridinium (PPA). Intriguingly, DHP and PPA were able to carry out easy proton abstractions and nucleophilic reactions in the presence of O2˙−, resulting in the corresponding products with sharp wavelength shifts, and elevated fluorescence intensities. Therefore, undesirable background fluorescence interference can be reduced during the monitoring and imaging process. Meanwhile, the developed dual-channel monitoring strategy not only provides observations of the O2˙− level fluctuations, but could also be employed to image the dynamic accumulation process of probes in the different cell organelles. Therefore, the design could provide a simple, accurate and universal platform for biological applications in future research work.

研究领域: 化学 · 生物学 · 材料科学 · 生物医学工程
✓ 已验证 产品关联 DOI PubMed 高影响因子
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