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High-Value-Added Utilization of Turpentine:Screening of Anti-Influenza Virus Agents fromβ-Pinene Derivatives

Journal of Renewable Materials 2024年第1期12卷 45-56页

作者： Yiwen Li Hongyan Si Peng Wang Hai Luo Minggui Shen Xiaoping Rao Zhanqian Song shibin shang Zongde Wang Shengliang Liao East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration Camphor Engineering Research Center of National Forestry and Grassland AdministrationCollege of ForestryJiangxi Agricultural UniversityNanchang330045China Institute of Chemical Industry of Forestry Products China Academy of ForestryNational Engineering Laboratory for Biomass Chemical UtilizationKey and Open Laboratory of Forest Chemical EngineeringState Forestry AdministrationKey Laboratory of Biomass Energy and MaterialJiangsu ProvinceNanjing210042China College of Chemical Engineering Huaqiao UniversityXiamen361021China

Turpentine is a renewable and resourceful forest *** deep processing and utilization of turpentine,particularly its primary componentβ-pinene,has garnered widespread *** study aimed to synthesize 40 derivatives ofβ-pinene,including nopinone,3-cyanopyridines of nopinone,myrtanyl acid,myrtanyl acylthioureas,and myrtanyl *** assessed the antiviral activities of theseβ-pinene derivatives against influenza virus A/Puerto Rico/8/34(H1N1)using the 3-(4,5-dimetylthiazol-2-yl)-2,5-diphenyltetrazolium bromide ***β-pinene derivatives were used before and after cellular infection with the influenza virus to evaluate their preventive and therapeutic effects against the H1N1 *** results showed that only compound 10o exhibited a preventive effect against the H1N1 virus with a half-maximal inhibitory concentration(IC50)value of 47.6μmol/*** the compounds,4e,4i,and 4l demonstrated therapeutic effects against cellular infection,with compound 4e displaying the most potent therapeutic effect(IC50=17.5μmol/L),comparable to the positive control *** findings indicated that certainβ-pinene derivatives exhibited in vitro antiviral activity against the H1N1 influenza A virus,warranting further investigation as potential anti-influenza agents.

关键词： Antiviral activity β-pinene derivative 3-cyanopyridine influenza virus

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松香基非异氰酸酯聚氨酯的制备及其性能研究

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林产化学与工业 2024年第1期44卷 1-8页

作者：张博文周月敏刘鹤刘仕伟商士斌宋湛谦青岛科技大学化工学院山东青岛266042 中国林业科学研究院林产化学工业研究所江苏南京210042

以松香衍生物丙烯海松酸(APA)为原料合成了丙烯海松酸二缩水甘油醚(AE),并进一步制得丙烯海松酸环碳酸酯(AC),利用AC中环碳酸酯基团与聚乙烯亚胺(PEI)、聚酯多元胺(Priamine 1074)中的氨基反应制备得到了松香基非异氰酸酯聚氨酯(ACPP)... 详细信息

以松香衍生物丙烯海松酸(APA)为原料合成了丙烯海松酸二缩水甘油醚(AE),并进一步制得丙烯海松酸环碳酸酯(AC),利用AC中环碳酸酯基团与聚乙烯亚胺(PEI)、聚酯多元胺(Priamine 1074)中的氨基反应制备得到了松香基非异氰酸酯聚氨酯(ACPP)薄膜材料。采用红外光谱(FT-IR)、热重(TG)、动态热机械法(DMA)等技术对ACPP材料的结构和性能进行了表征。研究结果表明:随着AC含量的增加,松香结构中氢化菲环刚性结构的引入量增加,从而使ACPP的力学性能增强,当氨基/环碳酸酯基物质的量比值为1时材料(ACPP_(1))的拉伸强度可达到15 MPa;同时ACPP材料的玻璃化转变温度(T_(g))显著增大,均大于40℃,当氨基/环碳酸酯基物质的量比值为0.8时,制备得到的材料(ACPP_(0.8))的T_(g)达到最大值,为49.4℃。自愈合性能测试结果显示:当带有划痕的ACPP_(1)在160℃、 5 MPa条件下,加热1 h后可以实现划痕的完全愈合,愈合率高达100%;另外,ACPP_(1)分别经过物理再加工和化学回收再加工后,力学性能仍可以恢复到原始强度的85%,展现出了优异的回收再加工性能。

关键词：丙烯海松酸非异氰酸酯聚氨酯自愈合再加工

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Fabricating Cationic Lignin Hydrogels for Dye Adsorption

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Journal of Renewable Materials 2023年第4期11卷 1793-1805页

作者： Chao Wang Xuezhen Feng Wanbing Li shibin shang Haibo Zhang Institute of Chemical Industry of Forest Products CAF、National Engineering Laboratory for Biomass Chemical Utilization、Key Laboratory of Chemical Engineering of Forest ProductsNational Forestry and Grassland Administration、Key Laboratory of Biomass Energy and MaterialJiangsu Co-Innovation Center of Efficient Processing and Utilization of Forest ResourcesNanjing210042China

Due to the low content of adsorption-active groups in lignin,its application in the field of adsorption is ***,we first prepared cationic kraft lignin acrylate,from which a cationic lignin(CKLA)hydrogel was further prepared by cationic kraft lignin acrylate,acrylamide,and N,N’-*** morphology,compression properties and swelling properties of CKLA hydrogels were *** prepared CKLA hydrogel was applied as an adsorbent for Congo *** effect of CKLA hydrogel dosages,initial concentration of Congo red,and pH on adsorption efficiency was *** maximum Congo red removal efficiency was obtained at the initial concentration of Congo red of 50 mg/L,pH 7,and 5 mg dosage of CKLA hydrogel with 20%cationic lignin *** five cycles of adsorption,the adsorption efficiency of the hydrogel for Congo red still reached more than 80%.The CKLA hydrogel showed pseudo-second-order adsorption kinetics for Congo red *** results demonstrate the potential of the CKLA hydrogel as an adsorbent for water treatment.

关键词： Adsorption lignin congo red hydrogel

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基于脱氢枞酸二芳胺的D-A-D型聚集诱导红光化合物的合成及其光谱性能

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林产化学与工业 2024年第4期44卷 1-8页

作者：许立君窦立薇罗汉荣高宏商士斌宋湛谦中国林业科学研究院林产化学工业研究所、江苏省生物质能源与材料重点实验室、国家林业和草原局林产化学工程重点实验室、林木生物质低碳高效利用国家工程研究中心江苏南京210042 南京林业大学、江苏省林业资源高效加工利用协同创新中心江苏南京210037 杭州弘纶浆纸有限公司浙江杭州311407

以12-脱氢枞酸二芳胺为供体(D),蒽醌基团为受体(A),通过C-N偶联的方法合成D-A-D型化合物6,6'-((9,10-二氧代-9,10-二氢蒽-2,6-二基)双((4-甲氧基苯基)氮二基))双(7-异丙基-1,4-二甲基-1,2,3,4,4a,9,10,10-八氢蒽-1-羧酸酯)(2DDPA-AQ),用核磁共振波谱和质谱表征其结构。测试2DDPA-AQ的紫外吸收光谱、荧光发射光谱、荧光量子产率及寿命、溶致变色效应、聚集诱导发光特性和抗光漂白特性;通过理论计算探讨其结构与性能间的关系。研究结果显示:2DDPA-AQ在甲苯中的最大紫外吸收波长为449 nm,在甲苯中和固体状态下的最大发射波长分别为630和653 nm,呈现红光发射;2DDPA-AQ在正己烷、环己烷、甲苯、二氧六环、四氢呋喃、乙酸乙酯中的最大荧光发射波长分别为578、584、630、638、645、650 nm。2DDPA-AQ的最大发射波长随溶剂极性的增大依次红移,表明其具有溶致变色效应和分子内的电荷转移行为。2DDPA-AQ的荧光发射强度随水/四氢呋喃(H2O/THF)中水体积分数的变化趋势表明其具有聚集诱导发光(AIE)特性;2DDPA-AQ在水体积分数为95%的H2O/THF中经连续30 min的紫外灯照射后,其荧光发射强度仅轻微减弱,表明其具有较强的抗光漂白特性。由实验所得数据计算2DDPA-AQ的HOMO/LUMO能级为-5.18 eV/-2.86 eV,带隙值为2.32 eV,按理论计算2DDPA-AQ的HOMO/LUMO能级为-4.91 eV/-2.14 eV,带隙值为2.77 eV,实验值与理论值略有偏差,由数据可知:2DDPA-AQ具有较窄带隙,符合红光分子的带隙特征。

关键词：脱氢枞酸二芳胺蒽醌 D-A-D型聚集诱导红光发射

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马来海松酸十八酰胺双羧酸钠表面活性剂的制备及其自组装性能研究

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林产化学与工业 2024年第4期44卷 51-60页

作者：张文静孙兴燊翟兆兰王丹商士斌宋湛谦中国林业科学研究院林产化学工业研究所、江苏省生物质能源与材料重点实验室、国家林业和草原局林产化学工程重点实验室、林木生物质低碳高效利用国家工程研究中心江苏南京210042 南京林业大学、江苏省林业资源高效加工利用协同创新中心江苏南京210037

以松香为原料经D-A加成、酰胺化和酸碱中和反应,合成了马来海松酸十八酰胺双羧酸钠(C_(18)MPA2Na),并利用FT-IR、^(1)H NMR、质谱确证了结构。采用表面张力法和尼罗红(NR)荧光探针法研究了C_(18)MPA2Na的表面活性,其临界胶束浓度(cmc)为... 详细信息

以松香为原料经D-A加成、酰胺化和酸碱中和反应,合成了马来海松酸十八酰胺双羧酸钠(C_(18)MPA2Na),并利用FT-IR、^(1)H NMR、质谱确证了结构。采用表面张力法和尼罗红(NR)荧光探针法研究了C_(18)MPA2Na的表面活性,其临界胶束浓度(cmc)为0.29 mmol/L,达到cmc时的表面张力值(γcmc)为41.11 mN/m,具有良好的表面活性。将C_(18)MPA2Na与十六烷基三甲基溴化铵(CTAB)复配,成功制备了一类黏弹溶液,采用原位冷冻电镜(Cryo-TEM)和流变性能测试研究了复配体系的微观结构和流变行为,结果表明黏弹溶液的聚集体为蠕虫胶束。固定复配体系中CTAB的浓度为80 mmol/L,零剪切黏度(η0)随C_(18)MPA2Na浓度的增加先增加后降低,C_(18)MPA2Na为15 mmol/L时,η0最大值为5.67×10^(4)mPa·s;固定复配体系中C_(18)MPA2Na与CTAB的比例(3∶16),η0随复配体系中C_(18)MPA2Na和CTAB总浓度的增加,表现出先快速升高后趋于平稳的趋势,η0与浓度的幂指数值为11.7;当C_(18)MPA2Na为15 mmol/L,CTAB浓度为80 mmol/L时,随着pH值的降低,η0先增加后降低,且在pH值为7.13时η0值最大,为7.67×10^(4)mPa·s。该研究表明松香的刚性骨架能够促进表面活性剂自组装。

关键词：松香表面活性剂黏弹溶液蠕虫状胶束

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Fluorescent properties and in vitro studies of new dehydroabietic acid-based diarylamines fluorescent probes

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Frontiers of Agricultural Science and Engineering 2017年第1期4卷 106-115页

作者： Hong GAO Jie SONG shibin shang Zhanqian SONG Institute of Chemical Industry of Forest Products Chinese Academy of ForestryNational Engineering Laboratory of Biomass Chemical Utilization/Key Laboratory of Biomass Energy and Material Department of Chemistry and Biochemistry University of Michigan-Flint

A series of dehydroabietic acid-based diarylamines have been synthesized in order to investigate their fluorescent properties, photostability, cell toxicity and in vitro fluorescence imaging. The geometries as well as their molecular properties were optimized at the B3LYP/6-31G~* level using Gaussian 03. The results indicate that molecular geometry, HOMO and LUMO energies, and energy gaps are important to predict absorption and fluorescent properties. Five of the compounds can be effectively taken up by human cervical carcinoma, human hepatocellular carcinoma SMMC-7721, human gastric cancer SGC-7901 and human lung adenocarcinoma A549 cells and strong blue fluorescent signals are detected in these cells. These compounds are potential candidates for fluorescent probes in biological diagnosis.

关键词： dehydroabietic acid-based diarylamine DFT study fluorescent probe in vitro imaging

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IN VITRO ACTIVITY OF EXTRACTS OF FIVE MEDICINAL PLANT SPECIES ON PLANT PATHOGENIC FUNGI

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Frontiers of Agricultural Science and Engineering 2021年第4期8卷 635-644页

作者： Shufeng YAO Jiali XU Haibo ZHANG Hong GAO shibin shang Dan WANG Institute of Chemical Industry of Forest Products Chinese Academy of ForestryKey Laboratory of Biomass Energy and MaterialJiangsu ProvinceKey Laboratory of Chemical Engineering of Forest ProductsNational Forestry and Grassland AdministrationNanjing 210042China Co-Innovation Center of Efficient Processing and Utilization of Forest Resources Nanjing Forestry UniversityNanjing 210037China

The antifungal effectiveness of extracts of five medicinal plant species was *** inhibitory activity of extracts of Eucalyptus tereticornis,Xanthium sibiricum,Artemisia argyi,Tupistra chinensis and Pyrola calliantha were evaluated against the mycelial growth of the plant pathogenic fungi Aspergillus niger,Botrytis cinerea,Penicillium digitatum,***,*** and Rhizopus *** plant extracts were prepared at 60°C using solvents(either water,50%ethanol(v/v),95%ethanol(v/v),ethyl acetate or petroleum ether).Fungicidal effects of all plants tested were *** extracts from the same plant species gave different degrees of *** aqueous extracts had weak or no activity on all fungi *** acetate and 95%ethanol extracts from *** rhizomes gave greater inhibition and a broader spectrum inhibition than the other *** may have potential as a new natural fungicide and may be used for the preservation of agricultural and forestry products such as fruits and vegetables.

关键词： Botrytis cinerea food preservation plant diseases plant pathogenic fungi Tupistra chinensis

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Preparation of Amide-Containing Insecticidal Derivatives from the Renewable Natural Productβ-Pinene

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Journal of Renewable Materials 2023年第5期11卷 2368-2380页

作者： Jiulong Wang Yanqing Gao Xiaoping Rao Zongde Wang shibin shang Zhanqian Song Hongyan Si Shengliang Liao East China Woody Fragrance and Flavor Engineering Research Center of National Forestry and Grassland Administration Camphor Engineering Research Center of National Forestry and Grassland AdministrationCollege of ForestryJiangxi Agricultural UniversityNanchang330045China College of Plant Protection Northwest Agriculture and Forestry UniversityYangling712100China College of Chemical Engineering Huaqiao UniversityXiamen361021China Institute of Chemical Industry of Forest Products China Academy of ForestryNational Engineering Laboratory for Biomass Chemical UtilizationState Forestry Administration’s Key and Open Laboratory for Forest Chemical EngineeringJiangsu Provincial Key Laboratory for Biomass Energy and MaterialNanjing210042China

The preparation of bioactive derivatives from the renewable natural product pinene is a hot research topic in the deep processing and utilization of *** this study,β-pinene was used to develop novel molecules as a promising new precursor of insecticide.A series of amide-containing derivatives ofβ-pinene were synthesized and *** insecticidal activities of these derivatives against Mythimna separate and Semiaphis heraclei were *** structure characterization results showed that the characterization data of amide-containing derivatives were in full agreement with their proposed *** insecticidal activities evaluation results indicated that amide-containing derivatives exhibited weak insecticidal activity against Mythimna separate,but exhibited moderate to good insecticidal activity against Semiaphis *** testing for 72 h,the corrected mortality against Semiaphis heraclei of compounds 5c,5e,5f,5 h,5j,and 5 m was 100%at 1000 mg/*** structure-activity relationship analysis results showed that the introduction of an amide group into the structure of derivatives improved their insecticidal activity against Semiaphis ***,the amide-containing derivatives containing the F and NO_(2) substituted benzene ring might improve their insecticidal activity against Semiaphis *** study will be helpful for the high value-added utilization of the natural renewable resourceβ-pinene and the development of novel insecticides.

关键词： Turpentine pinene derivative amide insecticidal activity

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Synthesis and characterization of castor oil-based polymeric surfactants

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Frontiers of Agricultural Science and Engineering 2016年第1期3卷 46-54页

作者： Xujuan HUANG He LIU shibin shang Zhaosheng CAI Jie SONG Zhanqian SONG Institute of Chemical Industry of Forestry Products Chinese Academy of Forestry Key Laboratory of Biomass Energy and MaterialNational Engineering Laboratory for Biomass Chemical Utilization Key and Laboratory on Forest Chemical Engineering State Forestry Administration School of Chemical and Biological Engineering Yancheng Institute of Technology Institute of Chemical Industry of Forestry Products Chinese Academy of Forestry Key Laboratory of Biomass Energy and MaterialNational Engineering Laboratory for Biomass Chemical Utilization Key and Laboratory on Forest Chemical Engineering State ForestryAdministration Department of Chemistry and Biochemistry University of Michigan-Flint

Dehydrated castor oil was epoxidized using phosphoric acid as a catalyst and acetic acid peroxide as an oxidant to produce epoxidized castor oil(ECO). Ringopening polymerization with stannic chloride was used to produce polymerized ECO(PECO), and sodium hydroxide used to give hydrolyzed PECO(HPECO). The HPECO was characterized by Fourier transform infrared,1H and13 Cnuclear magnetic resonance spectroscopies,gel permeation chromatography, and differential scanning calorimetry. The weight-average molecular weight of soluble PECO and HPECO were 5026 and2274 g$mol^(–1), respectively. PECO and HPECO exhibited glass transition. Through neutralizing the carboxylic acid of HPECO with different counterions, castor oil-based polymeric surfactants(HPECO-M, where M = Na^+, K^+or triethanolamine ion) exhibited high ef ficiency to reduce the surface tension of water. The critical micelle concentration(CMC) values of HPECO-M ranged from0.042 to 0.098 g$L^(–1)and the minimum equilibrium surface tensions at CMC(g cmc) of HPECO-M ranged from 25.6 to30.0 m N$m^(–1). The water-hexadecane interfacial energy was calculated from measured surface tension using harmonic and geometric mean methods. Measured values of water-hexadecane interfacial tension agreed well with those calculated using the harmonic and geometric mean methods.

关键词： epoxidized vegetable oil ring-opening polymerization interfacial tension polymeric surfactant

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Synthesis and bulk polymerization kinetics of monomer dehydroabietic acid-(2-acryloyloxy-ethoxy)-ethyl ester

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Frontiers of Agricultural Science and Engineering 2017年第1期4卷 97-105页

作者： Haibo ZHANG Yanping YANG He LIU Jie SONG shibin shang Zhanqian SONG National Engineering Laboratory for Biomass Chemical Utilization Key and Open Laboratory of Forest Chemical Engineering State Forestry Administration Key Laboratory of Biomass Energy and Material Institute of Chemical Industry of Forest ProductsChinese Academy of Forestry Department of Chemistry and Biochemistry University of Michigan-Flint Institute of New Technology of Forestry Chinese Academy of Forestry

A bulk polymerization monomer dehydroabietic acid-(2-acryloyloxy-ethoxy)-ethyl ester(DHADG-AC) was synthesized from dehydroabietic acid(DHA). The chemical structure of DHA-DG-AC was characterized by1~HNMR,(13)~CNMR, MS and FT-IR. The kinetics of the bulk polymerization of DHA-DG-AC was investigated by Differential Scanning Calorimeter(DSC).Two kinds of kinetic model(nth-order model and autocatalytic model) were used to investigate the polymerization process. The results showed that the experim e nt al DSC c u r ve s w e r e c o n si st e nt wi th t he computational data generated by the autocatalytic kinetic model, and the value of E_a was 95.73 k J·mol^(–1).

关键词： dehydroabietic acid bulk polymerization kinetics autocatalytic kinetic model

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