Anticancer effect of linalool via cancer-specific hydroxyl radical generation in human colon cancer

AIM To investigate the anticancer mechanisms of the monoterpenoid alcohol linalool in human colon cancer cells.METHODS The cytotoxic effect of linalool on the human colon cancer cell lines and a human fibroblast cell line was examined using the WST-8 assay. The apoptosisinducing effect of linalool was measured using the terminal deoxynucleotidyl transferase d UTP nickend labeling assay and flow cytometry with Annexin V. Oxidative stress was investigated by staining for diphenyl-1-pyrenylphosphine, which is a cellular lipid peroxidation marker, and electron spin resonance spectroscopy. Sixteen SCID mice xenografted with human cancer cells were randomized into 3 groups for in vivo analysis: control and low-dose and high-dose linalool groups. The control group was administered tap water orally every 3 d. The linalool treatment groups were administered 100 or 200 μg/kg linalool solution orally for the same period. All mice were sacrificed under anesthesia 21 d after tumor inoculation, and tumors and organs were collected for immunohistochemistry using an anti-4-hydroxynonenal antibody. Tumor weights were measured and compared between groups. RESULTS Linalool induced apoptosis of cancer cells in vitro, following the cancer-specific induction of oxidative stress, which was measured based on spontaneous hydroxyl radical production and delayed lipid peroxidation. Mice in the high-dose linalool group exhibited a 55% reduction in mean xenograft tumor weight compared with mice in the control group(P < 0.05). In addition, tumor-specific lipid peroxidation was observed in the in vivo model.CONCLUSION Linalool exhibited an anticancer effect via cancerspecific oxidative stress, and this agent has potential for application in colon cancer therapy.

Expression in Arabidopsis of a Strawberry Linalool Synthase Gene Under the Control of the Inducible Potato PI2 Promoter

To investigate the role of inducible linalool in Arabidopsis-insect interactions, the FANES 1 linalool synthase （LIS） cDNA from strawberry with plastid targeting and a synthetic intron （LIS＇） was placed under the control of the wound inducible proteinase inhibitor 2 （PI2） promoter from potato. The construct pBin-PPi2-LIS＇ was transformed to Arabidopsis thaliana ecotype Columbia 0. Kanamycin resistant TO seedlings were confirmed for the presence and transcription of the LIS＇ gene by PCR analysis on genomic DNA and by RT-PCR analysis on RNA. Genomic and RT-PCR products were sequenced to confirm correct splicing of the synthetic intron. The expression of active linalool synthase by the PPI2-LIS＇ gene construct in the transgenic lines was assessed by measuring linalool emission using solid phase micro-extraction （SPME） GC-MS measurements after induction with methyl jasmonate. Among 30 tested independent T2 transgenic lines, 10 exhibited linalool production. Linalool expression could be induced by methyl jasmonate treatment, but not by diamondback moth larvae.

Putative Mode of Action of the Monoterpenoids Linalool, Methyl Eugenol, Estragole, and Citronellal on Ligand-Gated Ion Channels

Essential oil has been used as sedatives,anticonvulsants,and local anesthetics in traditional medical remedies;as preservatives for food,fruit,vegetable,and grain storage;and as bio-pesticides for food production.Linalool(LL),along with a few other major components such as methyl eugenol(ME),estragole(EG),and citronellal,are the active chemicals in many essential oils such as basil oil.Basil oil and the aforementioned monoterpenoids are potent against insect pests.However,the molecular mechanism of action of these chemical constituents is not well understood.It is well-known that the c-aminobutyric acid type A receptors(GABAARs)and nicotinic acetylcholine receptor(nAChR)are primary molecular targets of the synthetic insecticides used in the market today.Furthermore,the GABAAR-targeted therapeutics have been used in clinics for many decades,including barbiturates and benzodiazepines,to name just a few.In this research,we studied the electrophysiological effects of LL,ME,EG,and citronellal on GABAAR and nAChR to further understand their versatility as therapeutic agents in traditional remedies and as insecticides.Our results revealed that LL inhibits both GABAAR and nAChR,which may explain its insecticidal activity.LL is a concentration-dependent,noncompetitive inhibitor on GABAAR,as the half-maximal effective concentration(EC50)values of c-aminobutyric acid(GABA)for the rat a1b3c2L GABAAR were not affected by LL:(36.2±7.9)lmol-1 and(36.1±23.8)μmol·L-1 in the absence and presence of 5 mmol·L-1 LL,respectively.The half-maximal inhibitory concentration(IC50)of LL on GABAAR was approximately 3.2 mmol·L-1.Considering that multiple monoterpenoids are found within the same essential oil,it is likely that LL has a synergistic effect with ME,which has been previously characterized as both a GABAAR agonist and a positive allosteric modulator,and with other monoterpenoids,which offers a possible explanation for the sedative and anticonvulsant effects and the insecticidal activities of LL.

Ferric Chloride Catalyzed Isomerization and Cyclization of Geraniol, Linalool and Nerol

Ferric chloride catalyzes the isomerization and cyclization of geraniol, linalool and nerol in acetonitrile giving a-terpineol in good to high yields.

Supercritical Equilibrium Data of the Systems Carbon Dioxide—Linalool and Carbon Dioxide—Orange Essential Oil

In this paper experimental equilibrium data on the system supercritical CO2-orange essential oil and the system supercritical CO2-linalool are reported at 323.15 K and 343.15 K, for pressures in the ranges of 7.6-13.5 MPa. The behavior of the system supercritical CO2-orange essential oil was represented by means of thermodynamic model, based on Peng-Robinson equation of state. To this aim the orange essential oil was represented by a mixture of limonene, linalool and β-caryophyllene, selected to represent the classes of monoterpenes, oxygenated terpenes and sesquiterpenes respectively. The model uses only regression parameters calculated from binary sub-systems, CO2-limonene and CO2-β-caryophyllene (taken from literature) and CO2-linalool (calculated from the fitting of original data reported in the present work) thus being predictive with respect to the multicomponent mixture.

阜阳地区6种杂薰衣草的引种栽培

为探讨杂薰衣草在阜阳地区的生态适应性与应用潜质,以6种杂薰衣草引种品种为研究对象,在栽植第3年对株高、冠幅、花枝数等生长指标,叶色、花色、花期等观赏指标,精油含量、成分、产量等经济指标进行调查分析。结果显示,在阜阳地区各品种均能正常生长,其中‘Mentha’株高最高,达81.30 cm;‘Sumian’冠幅最大,达114.25 cm;‘Nizza’花量最大,干重达252.63 g/株;‘Arabian Nights’花萼、花冠颜色深,花期最早,观赏期最长。经济指标检测显示,‘Arabian Nights’精油提取率最高,达5.34%;‘Nizza’精油产量最高,达9.22 g/株。气相色谱-质谱联用仪(GC-MS)分析显示,‘Nizza’精油成分中芳樟醇、乙酸芳樟酯含量较高,品质显著优于其他品种。综上,在阜阳地区,‘Arabian Nights’最适宜用于观赏栽培,‘Nizza’最适宜用于精油提取栽培。

茶树橙花叔醇和芳樟醇樱草糖苷含量全基因组关联分析及候选基因预测

橙花叔醇与芳樟醇是广泛分布于植物中的挥发性萜烯醇类化合物,在茶树新梢中主要以樱草糖苷形式存在,提高其含量对茶叶香气品质改良具有重要意义。为揭示茶树橙花叔醇和芳樟醇樱草糖苷的遗传机制,本研究以169个茶树自然杂交后代单株为关联群体,利用均匀分布在茶树染色体上的675,245个SNP标记,对3个年份下茶树新梢中橙花叔醇与芳樟醇樱草糖苷含量进行全基因组关联分析(genome-wide association study,GWAS)。结果表明,橙花叔醇与芳樟醇樱草糖苷含量的表型变异系数为60.83%~80.08%,广义遗传力分别为51.29%与61.87%,基本符合正态分布,具有典型的数量性状遗传特征。全基因组关联分析共检测到50个显著关联位点,各位点分别对橙花叔醇和芳樟醇樱草糖苷含量变化的贡献率均超过20%,其中橙花叔醇樱草糖苷含量(nerolidol primeveroside content,NPC)变化位点最大贡献率为38.73%,芳樟醇樱草糖苷含量(linalool primeveroside content,LPC)变化位点最大贡献率为39.07%。通过等位变异效应分析,鉴定出4个主效SNP位点及其优异等位变异,并发现1个可同时调控NPC和LPC的一因多效位点。结合已有的文献报道和基因的功能注释,筛选出每个显著位点置信区间内最有可能的候选基因共59个,主要涉及茶树的糖类代谢、转录调控、萜烯类生物合成等多个生物学过程,其中26个基因在适制绿茶品种和适制乌龙茶品种单芽中的表达水平存在显著差异。本研究为深入解析茶树橙花叔醇和芳樟醇樱草糖苷含量的遗传机制提供了新的信息,为加速培育高香型优异茶树新品种提供了重要的基因资源。

芳樟醇对生姜枯萎病菌的抑制作用

为明确芳樟醇对生姜枯萎病菌尖孢镰刀菌(Fusarium oxysporum)的抑菌效果与作用机制,以不同质量浓度的芳樟醇处理尖孢镰刀菌,对尖孢镰刀菌菌丝体生长、孢子萌发和细胞膜的损伤以及防治效果进行系统研究。结果表明:芳樟醇可显著抑制尖孢镰刀菌的菌丝生长,其半数有效浓度为1.183 g/L,最小抑菌浓度(minimal inhibitory concentration,MIC)为2.0 g/L,抑制效果与芳樟醇质量浓度呈剂量效应关系;以芳樟醇MIC处理尖孢镰刀菌6 h,其孢子浓度为(1.43±0.12)×10^(4)spores/mL,显著低于对照组((5.79±0.19)×10^(4)spores/mL)(P<0.05);MIC芳樟醇处理枯萎病菌尖孢镰刀菌12 h,其孢子萌发率仅为(5.83±2.16)%,显著低于对照组((95.12±3.78)%)(P<0.05)。1/2 MIC与MIC芳樟醇处理破坏了细胞膜的完整性,导致菌丝悬液中相对电导率、核酸渗漏量显著增加,菌丝中丙二醛浓度也显著增加,麦角固醇含量显著降低,减弱了尖孢镰刀菌的致病力;MIC芳樟醇处理3 d后姜块上没有病斑产生,有良好的防治效果。综上所述,芳樟醇通过抑制生姜枯萎病菌尖孢镰刀菌菌丝生长与孢子萌发、破坏细胞结构从而影响其正常的生理功能,本研究可为防治生姜枯萎病提供新思路。

Fabrication linalool-functionalized hollow mesoporous silica spheres nanoparticles for efficiently enhance bactericidal activity

To develop a novel food preservation technology for efficiently enhance bactericidal activity in a long term,hollow mesoporous silica spheres(HMSS)with regular nanostructures were applied to encapsulate natural organic antimicrobial agents.The chemical structures,morphologies and thermal stabilities of linalool,HMSS and linalool-functionalized hollow mesoporous silica spheres(L-HMSS)nanoparticles were evaluated by polarimeter,field emission scanning electron microscope(FE-SEM),transmission electron microscope(TEM),fourier transform infrared(FT-IR),thermal gravimetric analyzer(TGA),nitrogen adsorption-desorption,zeta potential and small angle X-ray diffraction(SXRD).The results show that the linalool was successfully introduced into the cavities of HMSS,and the inorganic host exhibited a high loading capacity of about 1500 mg/g.In addition,after 48 h of incubatio n,the minimum bactericidal concentrations(MBC)of L-HMSS against Escherichia coli(E.coli),Salmonella enterica(S.enterica)and Staphylococcus aureus(S.aureus),Listeria monocytogenes(L.monocytogenes)were decreased to be 4(<5)mg/mL and 8(<10)mg/mL,respectively.These results revealed linaloolfunctionalized hollow mesoporous spheres could efficiently improve the bactericidal activities of the organic component.Furthermore,SEM images clearly showed that L-HMSS indeed had an extremely inhibitory effect against gram-negative(E.coli)and gram-positive(S.aureus)by breaking the structure of the cell membrane.This research is of great significance in the application of linalool in nano-delivery system as well as food industry.

Oxygen vacancy engineering on cerium oxide nanowires for room-temperature linalool detection in rice aging

It is a huge challenge for metal oxide semiconductor gas sensors to inspect volatile organic compounds(VOCs)at room temperature(RT).Herein,the effective utilization of cerium oxide(CeO_(2))nanowires for RT detection of VOCs was realized via regulating its surface chemical state.Oxygen vacancy engineering on CeO_(2) nanowires,synthesized via hydrothermal method,can be manipulated by annealing under various controlled atmospheres.The sample annealed under 5%H_(2)+95%Ar condition exhibited outstanding RT sensing properties,displaying a high response of 16.7 towards 20 ppm linalool,a fast response and recovery time(16 and 121 s,respectively),and a low detection of limit of 0.54 ppm.The enhanced sensing performance could be ascribed for the synergistic effects of its nanowire morphology,the large specific surface area(83.95 m^(2)/g),and the formation of extensive oxygen vacancy accompanied by an increase in Ce^(3+).Additionally,the practicability of the sensor was verified via two varieties of rice(Indica and Japonica rice)stored in various periods(1,3,5,7,15,and 30 d).The experimental results revealed that the sensor was able to distinguish Indica rice from Japonica rice.Accordingly,the as-developed sensor delivers a strategic material to develop high-performance RT electronic nose equipment for monitoring rice quality.

一标多测法同时测定艾纳香药材中6种成分的含量

目的建立一标多测法同时测定艾纳香药材中β-蒎烯、樟脑、芳樟醇、β-石竹烯、α-石竹烯和龙脑6种主要活性成分含量。方法采用气相色谱法,色谱柱为PEG-20M(30 m×0.32 mm,10μm)石英毛细管柱,升温程序:起始温度60℃,维持2 min,以5℃·min^(-1)升至140℃,维持2 min,以2℃·min^(-1)升至150℃。高纯氮气为载气(99999%),火焰离子化检测器和进样口温度均设定为240℃。以龙脑为内参物,建立其与β-蒎烯、樟脑、芳樟醇、β-石竹烯和α-石竹烯的相对校正因子,计算各待测组分的含量,并将测定结果与用内标法测定结果进行比对。结果β-蒎烯、樟脑、芳樟醇、β-石竹烯、α-石竹烯和龙脑分别在2.01~80.4μg·mL^(-1)、6.03~241.2μg·mL^(-1)、2.00~80.0μg·mL^(-1)、6.06~242.4μg·mL^(-1)、4.04~161.6μg·mL^(-1)和80.1~3204μg·mL^(-1)浓度范围内具有良好线性关系,方法平均回收率(n=9)分别为98.4%(RSD=06%)、99.1%(RSD=1.2%)、98.9%(RSD=1.2%)、99.0%(RSD=1.3%),98.8%(RSD=1.5%)和98.5%(RSD=1.1%),与常规内标法比较,一标多测法所得结果无显著性差异。结论该方法简便快速,准确可靠,可用于艾纳香药材的质量控制。

Zwitterionic comb-like lipid polymers encapsulating linalool for increasing the fragrance retention time

Fragrances are widely used in cosmetics,apparel and detergents.However,the rapid evaporation of the aro ma shortens the useful life of the aromatic product.Therefore,improving the fragrance retention time of aromatic products and prolonging the service life of aromatic products are the key scientific problems that need to be solved in current aromatic products.In this study,zwitterionic comb-like lipid polymers were synthesized to encapsulate the fragrance molecule linalool.The results showed that the zwitterionic comb lipid molecules were capable of encapsulating more linalool than linear lipid molecules.At the same time,the zwitterionic comb-like lipid molecules also limited the slow release rate of the aroma,thereby increasing the fragrance retention time of the nano-fragrance.

Natural variation in linalool metabolites:One genetic locus,many functions?

The ubiquitous volatile linalool is metabolized in plants to nonvolatile derivatives.We studied Nicotiana attenuata plants which naturally vary in(S)-(+)-linalool contents,and lines engineered to produce either(R)-(-)-or(S)-(+)-linalool.Only(S)-(+)-linalool production was associated with slower growth of a generalist herbivore,and a large fraction was present as nonvolatile derivatives.We found that variation in volatile linalool and its nonvolatile glycosides mapped to the same genetic locus which harbored the biosynthetic gene,NaLIS,but that free linalool varied more in environmental responses.This study reveals how(S)-(+)-linalool and conjugates differ in their regulation and possible functions in resistance.

桧木醇通过TGF-β1/Foxp3/RORγt通路抑制乳腺癌细胞侵袭、迁移及凋亡的影响

目的 研究桧木醇对乳腺癌MCF-7细胞增殖和凋亡的影响及其相关机制。方法 用0、5、10和20μmol/L桧木醇处理人乳腺癌MCF-7细胞,采用划痕法检测细胞的迁移、Transwell法检测细胞侵袭能力、流式细胞技术检测细胞凋亡情况、采用蛋白免疫印迹法检测TGF-β1/Foxp3/RORγt信号通路相关蛋白的表达。结果 与对照组比较,5、10和20μmol/L桧木醇组细胞细胞划痕愈合率、侵袭能力均显著降低(P<0.01或P<0.05),且随着桧木醇浓度的升高,细胞划痕愈合率和侵袭能力逐渐下降,差异有统计学意义(P<0.05);细胞凋亡率显著升高(P<0.01或P<0.05),且随着桧木醇浓度的升高,细胞凋亡率逐渐升高,差异有统计学意义(P<0.05);TGF-β1、Foxp3、RORγt蛋白显著降低(P<0.05),随着桧木醇浓度的升高,TGF-β1、Foxp3、RORγt蛋白表达水平逐渐降低,差异有统计学意义(P<0.05)。结论 桧木醇可以通过抑制乳腺癌细胞中TGF-β1/Foxp3/RORγt信号通路来调节乳腺癌细胞的侵袭、迁移和凋亡,具有成为乳腺癌免疫治疗的潜在靶点。

烟叶香型特征致香成分研究及含量测定

采用高效液相色谱法(HPLC)对烟叶致香成分麦芽酚、乙基麦芽酚、香兰素、芳樟醇、β-大马酮的含量进行分析、鉴定和评价。通过查阅相关文献,确定以麦芽酚、乙基麦芽酚、香兰素、芳樟醇、β-大马酮烟叶特征致香成分为考查对象,在规定色谱条件下对检测方法的精密度、稳定性进行研究,并对湖南永州(2019)陈化烟叶样品中5种特征致香成分含量进行了测定分析。在规定色谱条件下,5种致香物质的特征吸收峰与其他各组分均达到良好的基线分离。建立的麦芽酚、乙基麦芽酚、香兰素、芳樟醇、β-大马酮HPLC测定方法可行。

炭焙和电焙白茶的关键风味物质和品质差异

以炭焙和电焙的不同等级白茶为实验材料,采用气相色谱-质谱联用和高效液相色谱技术,结合化学计量学方法,研究二者的香气物质、主要呈味物质与感官品质差异。结果表明:从样品中共检测出262种挥发性化合物,以萜类、杂环化合物、醇类、酯类和酮类为主,相对含量较高的有2-苯乙醇、芳樟醇、香叶醇、水杨酸甲酯、月桂烯、(E)-芳樟醇氧化物等。对比电焙的白茶,炭焙银针、白牡丹和寿眉分别筛选出77、16种和93种差异挥发性物质。香气活性值分析表明,芳樟醇、香叶醇、2-苯乙醇和月桂烯是炭焙白茶的重要香气物质,这些物质主要呈现天然清香、花果香或甜香。通过检测非挥发性化合物,结果表明炭焙与电焙白茶的儿茶素组分及总量、茶多酚、咖啡碱、水浸出物含量差异显著。感官审评分析表明,审评结果与挥发性物质、非挥发性物质的检测结果较一致。本研究有助于了解炭焙白茶的香气和滋味品质化学,为提高白茶品质提供理论支撑。

响应曲面法优化芳樟醇合成香叶基丙酮的工艺研究

在Na_(2)HPO_(4)·12H_(2)O催化剂作用下,通过Carroll反应,以芳樟醇与乙酰乙酸乙酯为原料合成了香叶基丙酮。考察反应温度、反应时间、物料摩尔比、催化剂用量对香叶基丙酮产率的影响。结果表明,优化出香叶基丙酮合成工艺为:反应温度174℃,反应时间7 h,芳樟醇与乙酰乙酸乙酯摩尔比1∶2.0,催化剂用量为3%(以芳樟醇质量为基准)。优化工艺条件下,香叶基丙酮的产率达89.1%。

酒花内生菌转化β-月桂烯合成芳樟醇和香叶醇

利用微生物催化酒花油中β-月桂烯生成芳樟醇和香叶醇是一种理想的生物转化途径,有利于提升酒花β-月桂烯的经济价值。该文从酒花雌花果中筛选出一株内生菌Z1,通过菌落形态观察、生理生化以及16S rDNA序列分析鉴定该菌株;研究其催化β-月桂烯合成芳樟醇和香叶醇的条件,并用于转化酒花油的β-月桂烯。结果表明,酒花内生菌Z1与菠萝泛菌(Pantoea ananatis)的菌落形态和生理生化特点相同,16S rDNA的同源性为98.2%,命名为Pantoea ananatis Z1。将该菌株于葡萄糖蛋白胨酵母麦芽粉(glucose peotone yeast and malt,GPYM)培养基中培养,转化14.1 g/L的β-月桂烯,产物芳樟醇和香叶醇浓度分别为0.89 mg/L和1.09 mg/L。对含有1.41 g/Lβ-月桂烯的酒花油进行转化,芳樟醇和香叶醇生成量达0.52 g/L和0.09 g/L,转化率分别提高了10248倍和1483倍。研究表明,P.ananatis Z1可将酒花油中的β-月桂烯一次性转化为芳樟醇和香叶醇,初步分析认为酒花油中β-月桂烯和芳樟醇的共同存在促进P.ananatis Z1对β-月桂烯转化。

传统中药浆糊的改良研究

针对传统中药浆糊存在制备繁琐、颜色较深、防霉效果有限等问题。通过向浆糊中直接添加花椒、黄柏的主要有效抗菌成分芳樟醇和盐酸小檗碱的方式对传统中药浆糊进行改良,从pH值、黏度、抗菌性能、吸湿性能对纸张颜色的影响等方面对改良后浆糊的性能进行研究。结果表明,添加芳樟醇和盐酸小檗碱后浆糊从弱酸性变成弱碱性,添加花椒或黄柏后浆糊含水率降低,盐酸小檗碱会显著改变浆糊颜色,芳樟醇对浆糊和纸张的颜色几乎没有影响,对黏度改变较小,有望用于面纸的修缮。添加质量分数10%盐酸小檗碱的浆糊防霉时间增长了约100 d,是黄柏浆糊的6倍。对古代传统中药浆糊的创新改良,具有重要意义。