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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 pinene.In 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 characterized.The insecticidal activities of these derivatives against Mythimna separate and Semiaphis heraclei were tested.The structure characterization results showed that the characterization data of amide-containing derivatives were in full agreement with their proposed structures.The 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 heraclei.After 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/L.The structure-activity relationship analysis results showed that the introduction of an amide group into the structure of derivatives improved their insecticidal activity against Semiaphis heraclei.Meanwhile,the amide-containing derivatives containing the F and NO_(2) substituted benzene ring might improve their insecticidal activity against Semiaphis heraclei.This 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

Genomic and transcriptional changes in response to pinene tolerance and overproduction in evolved Escherichia coli

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Synthetic and Systems Biotechnology 2019年第3期4卷 113-119页

作者： Fu-Xing Niu Yuan-Bin Huang Liang-Nian Ji Jian-Zhong Liu Institute of Synthetic Biology MOE Key Laboratory of Bioinorganic and Synthetic ChemistrySchool of Life SciencesSun Yat-Sen UniversityGuangzhou 510275China

α-pinene is an important monoterpene,which is widely used as a flavoring agent and in fragrances,pharmaceuticals and biofuels.Although an evolved strain Escherichia coli YZFP,which had higher tolerance to pinene and titer,has been successfully used to produce high levels of pinene,the pinene titer is much lower than that of hemiterpene(isoprene)and sesquiterpenes(farnesene)to date.Moreover,the overall cellular physiological and metabolic changes caused by higher tolerance to pinene and overproduction of pinene remains unclear.To reveal the mechanism of Escherichia coli YZFP with the higher tolerance to pinene and titer,a comparative genomics and transcriptional level analyses combining with CRISPR activation(CRISPRa)and interference(CRISPRi)were carried out.The results show that the tolerance to pinene and the overproduction of pinene in E.coli may be associated with:1)the mutations of the DXP pathway genes,the rpoA and some membrane protein genes,and their upregulations of transcription levels;and 2)the mutations of some genes and their downregulation of transcriptional levels.These comparative omics analyses provided some genetic modification strategies to further improve pinene production.Overexpression of the mutated cbpA,tabA,pitA,rpoA,sufBCDS,mutS,ispH,oppF,dusB,dnaK,dxs,dxr and flgFGH genes further improved pinene production.This study also demonstrated that combining comparative omics analysis with CRISPRa and CRISPRi is an efficient technology to quickly find a new metabolic engineering strategy.

关键词： Comparative omics analysis CRISPRa CRISPRi pinene Escherichia coli Biosynthesis

Zeolite-catalyzed three-phase hydration of α-pinene

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Chinese Journal of Chemistry 1986年第3期4卷 239-247页

作者： LIU Chu-Tsin CHENG Qing-Zhi YU Zheng SHEN Ben Guangzhou Institute of Chemistry, Academic Sinica Guangzhou Guangzhou Institute of Chemistry Academia Sinica Guangzhou

In this paper, the kinetics, the product distributions and the corresponding reactionsof some products of zeolite-catalyzed hydration of α-pinene have been studied. The results indicate:1. α-pinene is hydrated mainly to borneol, but isomerizations always accompany the hydrationand camphene and limonene are the main olefines formed. 2. The disappearance of α-pinenefollows the first-order kinetics, of which the rate constants, the activation energy as well as the activa-tion entropies have been calculated. 3. A probable mechanism has been proposed, in which thehydration of α-pinene through two equilibrating adsorbed intermediates, which, via three pathways,lead to derivatives of fenchane, bornane and p-menthane respectively. The distributions of the threepathways have been examined and appear to be determined by the stability of the adsorbed inter-mediates themselves

关键词： Zeolite-catalyzed three-phase hydration of show data pinene

Diversity in chemical compositions of essential oil of myrtle leaves from various natural habitats in south and southwest Iran

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Journal of Forestry Research 2015年第4期26卷 971-981页

作者： Abdollah Ghasemi Pirbalouti Lyle E.Craker Department of Medicinal Plants Islamic Azad UniversityShahrekord Branch Medicinal Plants Program Stockbridge School of AgricultureCollege of Natural SciencesUniversity of Massachusetts

Myrtle, Myrtus communis L. （Myrtaceae）, an evergreen shrub also known as wild myrtle, has a history of use as a culinary and medicinal plant. To determine the diversity within the species, plant leaves of myrtle were collected in 12 natural habitats in Iran for investigation of chemical constituents in the essential oil. Extraction of the essential oils produced yields ranging from 0.7 to 1.5 mL per 100 g dry tissue. An analysis of the oils by GC and GC/MS revealed 40 compounds, constituting 90.1-99.9 % of the essential oils. Chemical constituents varied with the site of sample origin, although the principal essential oil compo- nents from all populations, were pinene （17.5-37.1%）, 1,8-cineole （9.9-29.8 %）, linalool （7.0-23.1%）, and a-ter- pineol （5.3-8.3 %）. Limonene （tr, 22.7 %） was a major constituent in three populations. Characterized chemotypes included Chemotype pinene/1,8-cineole/linalool, Chemotype II： a-pinene/linalool, Chemotype III： a-pinene/1,8- cineole, and Chemotype IV： pinene/1,8-cineole/limonene.The main source of variabifity in chemical composition and oil yield appeared to be differences in environmental conditions and chemotypes as plant populations collected from close geographical areas could be classified in a cluster.

关键词： Chemotypes Myrtus communis Limonene Linalool 1,8-Cineole pinene Variation

Emissions of non-methane hydrocarbons from cars in China

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Science China Chemistry 2010年第1期53卷 263-272页

作者： DAI TianYou,WANG Wei,REN LiHong,CHEN JianHua & LIU HongJie Chinese Research Academy of Environmental Science,Beijing 100012,China Chinese Research Academy of Environmental Science Beijing China

This study investigated the exhaust emission of non-methane hydrocarbons(NMHCs) from cars in China at the Beijing driving cycle on the chassis dynamometer.The emission factor average of NMHCs was 0.9 g/km,which was over twice that from the Australian car fleet and 2-4 times that of the American car emission in the 1990s-2000s.The emission profile of Beijing cars showed higher fractions of aromatics and C4?C7 HCs,and lower percentages of C2?C3 HCs,compared with those of the US car fleet.The average ratio of benzene/toluene for cars tested was 0.5,the average benzene/toluene/ethyl benzene/xylenes(BTEX) ratios were 1/2.2/0.1/1.8,which were consistent with those of the Tanyugou tunnel located in the suburb of Beijing.α-pinene and β-pinene were detected from the exhaust gas on dynamometer for the first time,and had likely similar exhaust emission characteristics with C2?C3 HCs and styrene,giving an evidence that air pinenes may be related to human activities.Isoprene was also detected directly.These observations suggest that the procedure regarding pinenes and isoprene as coming from biologic sources of VOCs in the atmosphere should be applied with great care,especially in the core of the big city like Beijing.The specific reactivity of NMHCs was higher than that of cars of US,and the specific reactivity of volatile aromatic compounds was higher than that of the US SPECIATE database.

关键词： emission factor isoprene pinene photochemical reactivity Beijing driving cycle car

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室内空气中单萜类化合物检测方法的研究

分析测试学报 2008年第S1期27卷 120-123页

作者：沈朝烨徐以盛蒋志宏汪国权上海市疾病预防控制中心上海200336

Monoterpenoids are widely existing in indoor air.A GC-MS method was established for determination of monoterpenoids in the indoor air by using silonite coated canisters(SUMMA canisters),and preconcentrating low level samples utilizing three stages focuser.The method was suitable for the determination of trace VOCs in indoors air.The detection limits of method for α-pinene and β-pinene were both 0.71 μg/m3.

关键词： indoor air monoterpenoids pinene SUMMA canister GC-MS

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合成正龙脑的研制

林产化学与工业 1984年第4期 10-19页

作者：李世新顾树春陈传鹤上海无机化工研究所

作者研制成功了一种合成龙脑的新方法——氯乙酸法。此法所得产品质量很好,其中正龙脑含量通常在96％以上,而不含异龙脑。试验证明,在适当的温度(70℃)和催化剂存在下,正龙脑得率很高,蒎烯转化率较高。酯化反应能在稳定条件下操作,不会... 详细信息

作者研制成功了一种合成龙脑的新方法——氯乙酸法。此法所得产品质量很好,其中正龙脑含量通常在96％以上,而不含异龙脑。试验证明,在适当的温度(70℃)和催化剂存在下,正龙脑得率很高,蒎烯转化率较高。酯化反应能在稳定条件下操作,不会发生爆炸事故,克服了草酸法的缺点。本文论述了氯乙酸法的工艺过程,并对其反应条件、小型试验放大和模拟扩大试验的结果等,进行了讨论。

关键词： Synthetic borneol pinene Chloroacetic acid

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室内空气中单萜类化合物检测方法的研究

室内空气中单萜类化合物检测方法的研究

曲安奈德鼻喷雾剂联合桉柠蒎肠溶胶囊治疗分泌性中耳炎

2008年全国有机质谱学术会议

作者：沈朝烨徐以盛蒋志宏汪国权上海市疾病预防控制中心

室内空气中的挥发性有机化合物(volatile organic compounds,VOCs)来源广泛,种类繁多且成分复杂,包括大量具有化学毒性或生理学毒性的化合物。随着人们生活水平的日益提高,越来越多有潜在影响的挥发性、半挥发性有机物被广泛使用于日常... 详细信息

室内空气中的挥发性有机化合物(volatile organic compounds,VOCs)来源广泛,种类繁多且成分复杂,包括大量具有化学毒性或生理学毒性的化合物。随着人们生活水平的日益提高,越来越多有潜在影响的挥发性、半挥发性有机物被广泛使用于日常生活中,成为危害人类身体健康的隐形杀手。特别是近年来人们对居家环境、室内装修要求的不断提高,室内空气中VOCs的种类及浓度已不容忽视。本文着重研究室内空气中萜类化合物的分布水平,为室内空气中低浓度VOCs的检测及毒物学研究提供一定的依据。

关键词： indoor air monoterpenoids pinene SUMMA canister GC-MS

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中国耳鼻咽喉头颈外科 2012年第7期19卷 392-392,396页

作者：孟东蕊河北省河间市人民医院耳鼻咽喉头颈外科河北河间062450

分泌性中耳炎（secretory otitis media,SOM）主要以传导性聋及鼓室积液为主要特征的中耳炎症,儿童和成人发生率均较高,治疗方法主要为药物和鼓膜穿刺、切开置管术等,如何尽量减少有创治疗一直是临床医师探讨的问题。本研究用曲安奈德... 详细信息

分泌性中耳炎（secretory otitis media,SOM）主要以传导性聋及鼓室积液为主要特征的中耳炎症,儿童和成人发生率均较高,治疗方法主要为药物和鼓膜穿刺、切开置管术等,如何尽量减少有创治疗一直是临床医师探讨的问题。本研究用曲安奈德鼻喷雾剂（triamcinolone acetonide nasal spray,TANS）喷鼻加桉柠蒎肠溶胶囊（eucalyptol,limonene and pinene enteric soft capsules,ELPESC）治疗SOM取得了较好的临床治疗效果,

关键词：中耳炎,伴渗出液(Otitis Media with Effusion) 临床方案(Clinical Protocols) 曲安奈德鼻喷雾剂(triamcinolone acetonide nasal spray) 桉柠蒎肠溶胶囊(eucalyptol,limonene and pinene enteric soft capsules)