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CHEMISTRY & BIODIVERSITY · 2023 ·Vol. 20 ·期 8 ·e202300942 · IF 2.9

Design, Synthesis, and Bioactivity Evaluation of Novel Rosin Diterpenoid Derivatives as Potential Anti-glioma Agents

Jiayi Ou,Weiyun Tan,Gong Chen,Xianjing Yang,Yan Luo,Xiaobao Jin,Lianbao Ye

Glioma is the most common brain tumor and its treatment options are limited. Abietic acid and dehydroabietic acid are tricyclic diterpenoid oxygen compounds with strong lip solubility and anti-glioma activity. In this study, novel rosin diterpenoid derivatives were designed and synthesized using abietic acid and dehydrogenated abietic acid as lead compounds and their activities against T98G, U87MG, and U251 cells were evaluated by CCK-8 methods. The in vivo activity of compounds with stronger activity in vitro was preliminarily studied through the Zebrafish model. The results showed that the IC 50 values of B6 , B8 , B10 , and B12 were 11.47 to 210.6 μM, which were exhibited higher antiproliferative potency against T98G, U87MG, and U251. The scratch experiment showed that B12 inhibited the migration of T98G in a time-dependent and concentration-dependent manner. The results of in vivo activity further explained that B12 could inhibit the proliferation of the T98G. The pKa values of B6 , B8 , B10 , and B12 were 7.17 to 7.35, which were within the ideal range of glioma drugs. The ADME predictions indicated that these derivatives could pass through the blood-brain barrier. In addition, molecular docking primarily explained interaction between compounds and protein. These results suggested that B12 should be a promising candidate that merits further attention in the development of anti-glioma drugs. Graphical

研究领域: 药理学 · 肿瘤学 · 药物化学 · 药物发现
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SENSORS AND ACTUATORS B-CHEMICAL · 2024 · IF 8

Copper abietate/polyvinyl acetate composite film for enhanced humidity sensing in Chinese herbal medicine monitoring systems

Ningning Tan,Yaohang Weng,Haijun Li,Bo Chen,Lan Zhao,Biao Huang,Beili Lu,Lirong Tang

Sensing materials derived from natural and biodegradable sources are increasingly being developed and applied to realize environmentally friendly technologies. In this paper, we present the synthesis, characterization, and application of a novel copper abietate/polyvinyl acetate (CuA/PVAc) composite film, specifically engineered to enhance the humidity-sensing capabilities of Chinese herbal medicine monitoring systems. The sensing material was synthesized by strategically melding copper abietate, a natural renewable material, with PVAc to exploit their combined synergistic properties for optimal humidity-sensing performance. Comprehensive characterization techniques, including inductively coupled plasma optical emission spectrometry (ICP-OES), field-emission scanning electron microscopy (FESEM), water contact angle measurements, and Fourier transform infrared (FT-IR) spectroscopy, were employed to confirm the formation of CuA/PVAc composites. These analyses confirmed the homogeneity and intended chemical composition of the composite films.The resultant CuA-1/PVAc-4 (0.4 μg/μL) composite film exhibited a good logarithmic relation (0.9988) with relative humidity (RH) over a wide range (11 %–97 %) and high sensitivity (24.55 Hz/%RH). Moreover, this study introduces a novel, eco-friendly approach by integrating the CuA/PVAc composite with a quartz crystal microbalance (QCM) sensor and a sophisticated wireless circuit that enables real-time, Wi-Fi-based humidity monitoring tailored for the preservation of Chinese herbal medicines. The implementation of this wireless humidity detection system represents a significant advancement in the application of environmentally friendly materials in sensor technology and offers a practical and scalable approach for precise environmental monitoring.

研究领域: 材料科学 · 传感器技术 · 中医药学
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ENERGY & FUELS · 2019 · IF 3.021

Thermal Stability of Abietic Acid and Its Oxidation Products

Yuanlin Li,Xingliang Xu,Mengmeng Niu,Jing Chen,Jiahua Wen,Hao Bian,Chang Yu,Min Liang,Li Ma,Fang Lai,Xiongmin Liu

The thermal oxidation characteristics of abietic acid were investigated through tracing the oxidation process in custom-designed mini closed pressure vessel test under isothermal and step temperature conditions. Peroxide generation and the peroxide value of abietic acid oxidation process were measured using thin-layer chromatographic analysis and iodimetry. The primary oxidation product—peroxide—was separated by column chromatography with further structure characterization, and its thermal decomposition characteristics were assessed via a differential scanning calorimeter (DSC). The oxidation was mainly initiated through the radical generation from hydrogen abstraction on the unsaturated conjugated double bonds of abietic acid above 343 K. The main hydroperoxide, 7-hydroperoxy-13-abiet-8(14)-enoic acid, was found in abietic acid with a high peroxide value. The exothermic onset temperature (T0) and decomposition heat (QDSC) of this peroxide were 353.94 K and 545.37 J·g–1, respectively. Finally, a second-stage oxidation process of abietic acid was first investigated when the temperature reached the abietic acid melt point (448 K) with complex oxidation products forming, such as dehydroabietic acid, palustric acid, 7-oxodehydroabietic acid, neoabietic acid, 7-methoxy-tetradehydroabietic acid, 12-deoxyroyleanone acid, and 12-methoxy-abietic acid.

研究领域: 有机化学 · 物理化学
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FOOD CHEMISTRY · 2024 · IF 8.5

Self-assembled Abietic acid encapsulated nanoparticles to improve the stability of Proanthocyanin B2

Ying Han,Xuening Yang,Shiyao Fu,Xiaoting Wang,Hua Zhang,Xiaojie Wei,Bin Li,Xin Yang

Procyanidin B2 ( Pac B2 ) has attracted much attention due to its strong antioxidant activity , but poor in vivo stability limits its wide application in food and medicine. In this paper, composite nanoparticles ( NPs ) were constructed using abietic acid ( AA ) as a carrier, which significantly enhanced Pac B2 stability. A spherical morphology and average diameter of 396.05 nm were observed in AA-Pac B2 NPs synthesized by solvent co-precipitation. Pac B2 encapsulation was 11.28 %, and thermal stability is improved. Infrared, Ultraviolet spectrum, and MD (molecular dynamics) spectroscopy revealed hydrogen bonding and hydrophobic interaction between AA and Pac B2 . For up to 2 h at 37 °C, Pac B2 can be sustainably released in simulated gastric and intestinal fluids. In vitro , AA-Pac B2 NPs at the same concentration exhibited higher bioavailability and uptake efficiency than free Pac B2 . The data demonstrate the potential of AA NPs for improving polyphenol thermal stability and bioavailability.

CAS / MDL: 3326-32-7
研究领域: 食品科学 · 药学
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Soft Matter · 2021 ·Vol. 17 ·期 43 ·9950-9956 · IF 3.679

Formation of asymmetric belt-like aggregates from a bio-based surfactant derived from dehydroabietic acid

Hao Chen,Tingting Yan,Jinpeng Zhang,Xiaomei Pei,Zhenggang Cui,Binglei Song

The morphology and physicochemical properties of ordered molecular aggregates are closely related to surfactant molecules. Herein, a rosin-based amine oxide surfactant containing a large hydrophobic group (abbreviated R-10-AO) was synthesized from dehydroabietic acid, which is an important derivative of rosin. Cryogenic transmission electron microscopy (cryo-TEM) images and small-angle X-ray scattering (SAXS) showed that at a concentration of ∼5 mM, R-10-AO molecules formed flexible nanobelts with a thickness of only 2–3 nm. The width of these nanobelts was 50–150 nm and the length was more than 1 μm. The formation of the stable nanobelts arose from the strong van der Waals forces of the bulky hydrophobic portions of R-10-AO in solution, facilitating the stability of the asymmetrical aggregates. Rheological tests showed that the formed nanobelts were thermodynamically stable. The entanglement of these nanobelts led to significant viscoelasticity of the solutions. The zero-shear viscosity (η0) of the R-10-AO solution reached 10 Pa s at a concentration of 5 mM, which is much greater than that of most wormlike micellar solutions. This work provides the inspirations of preparing aggregates with novel properties using natural products.

CAS / MDL: 646-25-3 24424-99-5
研究领域: 材料科学 · 胶体与界面化学
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INDUSTRIAL CROPS AND PRODUCTS · 2021 · IF 5.645

Synthesis and properties of rosin grafted polymers via “grafting from” ATRP: The role of rosin-based initiator

Juan Yu,Chaoqun Xu,Xiaoli Song,Chuanwei Lu,Chunpeng Wang,Jifu Wang,Fuxiang Chu

Rosin is an important renewable resource. However, preparation of rosin-based polymers with good performance is still challenging. In this work, a series of rosin-based polymers were prepared via “grafting from” atom transfer radical polymerization (ATRP) using dehydroabietic acid (DA, extracted from pine trees) derived ATRP initiator (2-BriBEDA, (2-bromoisobutyric) hydroxyethyl ester of dehydroabietic acid). The graft polymerization behavior of polar monomer methyl methacrylate (MMA), nonpolar monomer lauryl methacrylate (LMA) from DA were investigated. The kinetic studies showed that the ATRP processes of MMA, LMA as well as MMA- co -LMA were all living and controlled, which indicated that 2-BriBEDA was a good ATRP initiator. With the introduction of DA, all rosin-based copolymers showed improved thermal stability, UV-blocking performance, hydrophobicity and mechanical properties. In addition, DA- g -P(MMA- co -LMA) polymers showed good mechanical and elastic properties with highest tensile strength of 5.10 ± 0.87 MPa and strain of 513 ± 32 % and elastic strain recovery above 70 % which was comparable with other reported sustainable thermoplastic elastomers (TPEs) polymers. This work demonstrates an alternative avenue for rosin-based polymer design to achieve the improvement in thermal, UV-blocking and mechanical performance.

研究领域: 材料科学 · 化学工程
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RESEARCH ON CHEMICAL INTERMEDIATES · 2016 ·Vol. 42 ·期 6 ·6181-6190 · IF 1.833

Hydrogenation of rosin over PVP-stabilized Pd nanoparticles in aqueous/organic biphasic system

Wang Meng-Meng,Liu Shi-Wei,Li Lu,Yu Shi-Tao,Xie Cong-Xia,Song Zhan-Qian

Rosin hydrogenation using polyvinylpyrrolidone (PVP)-stabilized Pd colloidal nanoparticles as catalyst in an aqueous/organic biphasic system was investigated. The influence of preparation methods on the size of Pd nanoparticles for hydrogenation of rosin was marked. Compared with traditional catalysts Pd/C and Raney-Ni, PVP-stabilized Pd colloidal nanoparticles showed excellent catalytic activity and promoted formation of the product tetrahydroabietic acid (THAA). More than 93 % rosin was hydrogenated, and the mass fraction of THAA was 54.2 % when the reaction was carried out at 160 °C for 4 h. It was also found that PVP-stabilized Pd colloidal nanoparticles exhibited good reusability for hydrogenation, with no obvious decrease in catalytic performance when reused six times.

研究领域: 催化化学 · 纳米材料 · 有机合成 · 绿色化学 · 胶体化学
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JOURNAL OF MATERIALS SCIENCE · 2017 ·Vol. 53 ·期 4 ·2434-2442 · IF 2.599

Synthesis and characterization of ordered mesoporous silica using rosin-based Gemini surfactants

Li Wenkai,Xie Danhua,Song Binglei,Feng Lin,Pei Xiaomei,Cui Zhenggang

As structure-directing agents, the molecular structure of surfactants is critical for determining the properties of prepared mesoporous materials. Using dehydroabietic acid as a starting material, a series of rosin-based Gemini surfactants (abbreviated as R- n -R, n  = 3, 6, 8 and 10, indicating the carbon atom number contained in the spacer) were synthesized and applied as templates in the preparation of ordered mesoporous silica. The structures and morphologies of the samples were characterized by X-ray diffraction, scanning electron microscope, transmission electron microscope and N 2 adsorption–desorption. The R- n -R surfactants feature rigid tricyclic hydrophobic groups with large volumes, which are beneficial for the formation of a three-dimensional cubic phase. Furthermore, the spacer length was found to have a tremendous effect on the structure of the prepared mesoporous silica materials. The head group of R-3-R, which has a short spacer, is excessively charged, leading to silica nanoparticles with an irregular morphology and a rather low BET surface area. With longer spacer lengths, R-6-R, R-8-R and R-10-R are conducive to generating silica nanoparticles with a novel dumbbell-like morphology and with higher BET surface areas of 1171, 1096 and 1186 m 2  g −1 , respectively. The results demonstrate the particularities of the Gemini surfactant structure in the preparation of mesoporous silica nanoparticles with novel morphologies, and the details of the molecular interactions that occur in the condensation of silicate anions are also revealed.

CAS / MDL: 109-55-7
研究领域: 材料科学 · 化学 · 纳米技术
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