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The Essential Oil of Bupleurum fruticosum L. from Corsica

The Essential Oil of Bupleurum fruticosum L.from Corsica:

A Comprehensive Study

by Kai Liu,Marie Laure Lota,Joseph Casanova,and Fe′lix Tomi*

Universite′de Corse-CNRS,UMR6134SPE,Equipe Chimie et Biomasse,Route des Sanguinaires, F-20000Ajaccio(phone:t33-495-524122;fax:t33-495-524142;e-mail:felix.tomi@univ-corse.fr)

A detailed analysis of Bupleurum fruticosum oil was carried out by combination of GC(RI),GC/ MS,and13C-NMR analyses.After fractionation by column chromatography,34components accounting for97.8%of the oils were identified.The main component was b-phellandrene(67.7%),followed by sabinene(9.3%),and limonene(5.6%).The evolution of the chemical composition according to the stages of development of the plant was investigated as well as the composition of leaf,twig,and flower oils.A solvent-free microwave extraction(SFME)of aerial parts was carried out and the composition of the extract compared with that of the essential oil.Finally,57oil samples isolated from aerial parts of individual plants,collected all around Corsica,were analyzed,and the data were submitted to statistical analysis.Although the contents of the main components varied,only one group emerged,accompanied with some atypical compositions.

Introduction.–Bupleurum is a genus of the Apiaceae family comprising ca.200 species and primarily located in the Northern hemisphere,Eurasia,and North Africa. In the Mediterranean basin and North Africa,ca.25species are represented with some restricted endemism(B.dianthifolium,Italy;B.barceloi and B.bourgaei,Balearic Islands,Spain).About50species from this genus(e.g.,B.falcatum,B.chinense,B. fruticosum,etc.)have been studied chemically,and more than100compounds have been isolated(saikosaponins,phenylpropanoids,lignans,coumarins,flavonoids,sterols, etc.)[1].

Bupleurum fruticosum L.is an evergreen,glaucous,perennial,bushy shrub,1-to-2-m high,with simple elliptic-oblong leaves,which is represented all around the Mediterranean basin and in the islands[1–3].B.fruticosum emits a strong odor and is repulsive for animals.On the contrary,the fragrant and tasty fruits have been used as spices[4].

Only a few studies were concerned with the chemical composition of the essential oil from Bupleurum fruticosum.The first study dates back to1911and reported the occurrence,in oil from Sardinia(Italy),of a-pinene,b-phellandrene,and the so-called buplerol,a monoterpene alcohol never identified later in the B.fruticosum oils[5].The next study was reported in1970by Peyron and Roubeau[2].They identified various monocyclic and bicyclic monoterpenes in an oil sample isolated from the flower heads of plants harvested in the French Alpilles.

Since1987,various investigations on the chemical composition of B.fruticosum essential oil were conducted using modern analytical techniques(e.g.,GC/MS in combination with GC retention indices(RI)).Although they related to wild growing

2009Verlag Helvetica Chimica Acta AG,Zürich

and cultivated plants as well as different parts of the plant(aerial parts,leaves,stems, flowers,or fruits),the results may be summarized by the occurrence of four chemical compositions,all dominated by monoterpene hydrocarbons.

The composition dominated by b-phellandrene was observed in oil samples of various origins:i)wild plants from Sardinia,Italy(64.5%;sabinene,20.7%;aerial parts, leaves,stems,and flowers)[6],ii)in vitro multiplied plants in the Botanical Garden of the University of Urbino,Italy,(60.9%;sabinene,12.8%;leaves)[7],and iii)wild plants of Eastern Libya(49.3%;a-pinene,15.3%;epigean parts)[8].Otherwise,a-pinene and b-pinene(41.2and35.9%,resp.)were the major components of fruit oil from Spain[9].

Finally,it should be mentioned that oils with different compositions were isolated from leaves and stems of the same plant cultivated at the Istituto Botanico di Urbino, Italy.Leaf oil was dominated by b-phellandrene and sabinene(41.7and35.8%,resp.

[7],or38.7and39.7%,resp.[4]),while stem oil contained mostly g-terpinene and a-phellandrene(49.8and18.3%,resp.[7],or48.8and12.2%,resp.[4]).

An oil sample from Sicily,Italy,isolated by hydrodistillation/simultaneous solvent extraction,contained a-pinene(21.7%),b-phellandrene(21.3%),and b-pinene (13.2%)as main components[10].

The aim of the present study was to give an overview of the essential oil from Bupleurum fruticosum L.growing wild in Corsica.First,we reported on the detailed analysis of a bulk sample,by combination of chromatographic and spectroscopic techniques.Then,we compared the compositions of leaf,stem,and flower oils.We followed the evolution of the chemical composition of the oil from aerial parts according to the stage of development of the shrub(before,during,and after flowering).Finally,we examined the chemical variability.An interesting point,in our opinion,is that sampling,preparation of the oils,and analyses were carried out at two periods separated by ten years,i.e.,in1997and2007.Individual components were identified by combination of GC(RI),GC/MS,and13C-NMR.

Results and Discussion.–Detailed Analysis of an Oil Sample of Bupleurum fruticosum.The essential oil was isolated by vapor distillation of the aerial parts of Bupleurum fruticosum by the society U Mandriolu.It was analyzed by combination of GC(RI),GC/MS,and13C-NMR.To identify more components and to confirm the identification of some compounds,the bulk sample was submitted to column chromatography(CC)and the fractions were analyzed by GC(RI)and13C-NMR. Moreover,two minor esters,cinnamyl isovalerate and cinnamyl2-methylbutyrate were identified by comparison of their spectral NMR data with those of authentic samples prepared by esterification of cinnamyl alcohol.

Individual components of the essential oil,their retention indices on apolar and polar columns,as well as their relative percentages and the mode of identification are reported in Table1.In total,34components,which represented97.8%of the total amount of the oil,were identified,most of them(25)by GC(RI),GC/MS,and 13C-NMR.Among the identified compounds,18were hydrocarbons,and the oil was characterized by a high content of b-phellandrene(67.7%).Two monoterpenes, sabinene(9.3%)and limonene(5.6%),were present in an appreciable amount.A few acyclic,non-terpenic compounds(decan-1-ol,hexyl acetate,octyl acetate,and hexyl

https://www.sodocs.net/doc/004793600.html,ponents of the Essential Oil Isolated from Aerial Parts of Bupleurum fruticosum L.from

Corsica

Components a)Retention index(RI)Composition[%]Identification mode

BP-1BP-20

a-Thujene92310270.1RI,MS

a-Pinene9311027 1.6RI,MS,13C-NMR Camphene94410730.1RI,MS

Sabinene96711299.3RI,MS,13C-NMR b-Pinene97211160.3RI,MS

Myrcene9821166 2.3RI,MS,13C-NMR Hexyl acetate99412750.1RI,MS,13C-NMR a-Phellandrene9991171 2.4RI,MS,13C-NMR d-Car-3-ene100611530.4RI,MS,13C-NMR a-Terpinene101111760.2RI,MS

p-Cymene101312760.3RI,MS,13C-NMR Limonene b)10261207 5.6RI,MS,13C-NMR b-Phellandrene b)1026122267.7RI,MS,13C-NMR g-Terpinene10501250 1.2RI,MS,13C-NMR Terpinolene108012880.2RI,MS

Linalool108415500.1RI,MS,13C-NMR Cryptone115716830.1RI,MS,13C-NMR Terpinen-4-ol116316050.3RI,MS,13C-NMR Estragole117616780.5RI,MS,13C-NMR Octyl acetate119314780.5RI,MS,13C-NMR Hexyl isovalerate122614480.2RI,MS,13C-NMR Decanol125517680.8RI,MS,13C-NMR Bornyl acetate12711583tr c)RI,MS,13C-NMR Citronellyl acetate133516660.3RI,MS,13C-NMR Geranyl acetate13611762 1.9RI,MS,13C-NMR (E)-b-Farnesene14481669tr c)RI,MS,13C-NMR Germacrene D1*******tr c)RI,MS,13C-NMR Bicyclogermacrene149517380.2RI,MS,13C-NMR b-Bisabolene15031730tr c)RI,MS,13C-NMR Elemicine151722370.1RI,MS,13C-NMR Viridiflorol158720930.3RI,MS,13C-NMR Ledol159820370.1RI,MS,13C-NMR Cinnamyl2-methylbutyrate164623100.3RI,MS,13C-NMR Cinnamyl isovalerate165523340.4RI,MS,13C-NMR Total97.8

a)Order of elution and percentages of components are given for the apolar column(BP-1),except for compounds with b).b)Percentages are given for the polar column(BP-20).c)tr:traces. isovalerate)were also identified.Phenyl propanoids were represented by cinnamyl esters,estragole,and elemicine(Fig.1).

The actual content of b-phellandrene was determined using quantitative13C-NMR spectroscopy.Waiting a period of5T1of the longest T1value before applying another pulse,combined with a908pulse angle,allows both maximal steady-state magnetization and complete relaxation of each C-atom[11].Applying the aforementioned

parameters with the gated-decoupling technique,which provides the suppression of the nuclear Overhauser enhancement(NOE),is well-known as the standard sequence for quantitative NMR measurements[12].The mean value of the integrals of the signals of the protonated C-atoms was compared to those of the CH2groups of diglyme,used as internal standard(see Exper.Part).The percentage of b-phellandrene determined by GC(FID)is in agreement with that evaluated from NMR data(67.7and65.8%,resp.).

Essential Oils from Various Parts of the Plant.It could happen that essential oils isolated from different parts of the plant have different compositions.To verify this point,we first compared the composition of leaf and stem oils isolated from two individual plants(Samples A and B),and we observed,in both cases,that the oils exhibited a very similar composition,the yield of the leaf oil(2.1and3.6%)being higher than that of the stem oil(1.6and2.1%).More interesting is the comparison of leaf and stem oils with flower oil.The yield of oil isolated from leaves and stems(1.6 and2.2%)is higher than that isolated from flowers(1.1and1.3%).The nine major components of the corresponding oils,identified by GC(RI)and13C-NMR,accounted for95.9–97.9%of the total amount(Table2).Although the composition is quite similar with respect to the monoterpene hydrocarbons and oxygenated monoterpenes,

Table2.Chemical Composition(major components)[%]of the Flower and the Leaf and Stem Essential

Oils of Bupleurum fruticosum L.from Corsica

Components a)Sample A Sample B

Flower Leaf and stem Flower Leaf and stem a-Pinene 1.5 2.0 1.6 1.9 Sabinene 2.5 1.5 1.0 1.1 Myrcene 2.0 2.3 2.0 2.3

a-Phellandrene 3.0 3.4 3.0 3.3 Limonene b) 5.5 5.7 5.5 6.0

b-Phellandrene b)71.377.371.879.1 Estragole 4.8– 6.6tr c)

Decanol 1.1 1.2 1.30.7

Geranyl acetate 2.3 2.4 1.7 1.2

Yield[%(w/w)] 1.1 1.6 1.3 2.2

a)Order of elution and percentages of components are given for the apolar column(BP-1),except for

compounds with b).b)Percentages are given for the polar column(BP-20).c)tr:traces.

some differences are observed for phenyl propanoids.Indeed,it could be pointed out that the flower oil contained appreciable amounts of estragole(6.6and4.8%),not present in leaf and stem oils.

Solvent-Free Microwave Extraction.Solvent-free microwave extraction(SFME)is an original combination of microwaves and dry distillation[13].The essential oils from two individual samples(Samples C and D),extracted by SFME for30min,exhibited a chemical composition qualitatively and quantitatively similar to those obtained by conventional hydrodistillation with a Clevenger apparatus for3–4h(Table3).We just noted that the content of the major component,b-phellandrene,was slightly lower,and that higher percentages of oxygenated compounds were observed by SFME in comparison with conventional hydrodistillation.In terms of time and energy,SFME allows,in general,substantial savings of costs and may be considered as a green technology.However,due to the very low yields(0.21and0.25%)obtained by this technique in comparison to those attained with conventional hydrodistillation(1.71and 1.86%),SFME seems not appropriate for the industrial isolation of the volatiles of Bupleurum fruticosum.

Table3.Chemical Composition(major components)[%]of the Essential Oil Isolated from Aerial Parts of Bupleurum fruticosum by SFME and by Conventional Hydrodistillation(HD) Components a)Sample C Sample D

HD SFME HD SFME a-Pinene 2.1 1.1 2.1 1.3 Sabinene 1.00.7 1.00.9 b-Pinene0.40.20.30.3 Myrcene 2.4 2.0 2.3 2.0 a-Phellandrene 3.4 3.5 3.3 2.8 para-Cymene0.20.20.30.4 Limonene b) 6.1 6.1 6.1 5.9 b-Phellandrene b)79.776.879.177.5 Octyl acetate0.30.50.30.5 Decanol0.4 1.30.4 1.0 Geranyl acetate0.8 1.2 1.6 2.5 Elemicin0.20.90.10.2 Cinnamyl isovalerate0.10.60.20.5 Yield[%(w/w)] 1.710.21 1.860.25 a)Order of elution and percentages of components are given for the apolar column(BP-1),except for compounds with b).b)Percentages are given for the polar column(BP-20).

Evolution of the Composition before,during,and after Flowering.The composition of essential oils isolated from aerial parts of plants collected before(May2005),during (July or September2005),and after(November2005)the flowering period are reported in Table4.The13major components,which represented from92.6to96.6% of the total amount of the oils,were identified by GC(RI)and13C-NMR.b-Phellandrene is strongly predominant all along the physiological cycle of the plant.The percentage of this major component(70.4–78.3%)varied slightly between samples, although the two samples varied in their composition by the content of sabinene(6.0

and8.2%in Sample E vs.1.2and1.5%in Sample F).There was no significant variation in the composition of the essential oils collected before,during,and after the flowering period.Conversely,the yield of essential oils varied drastically,being lower(0.8and 1.2%)before and higher during and after the flowering period(2.4–2.9%)(Table4). Table4.Evolution of the Chemical Composition(major components)in[%]of the Essential Oils Isolated from Aerial Parts of Bupleurum fruticosum before(BF),during(DF),and after(AF)Flowering

Components a)RI Sample E Sample F

BP-1BP-20BF DF AF BF DF AF a-Pinene9311027 1.9 1.8 1.8 2.0 2.0 1.9 Sabinene96711297.3 6.08.2 1.5 1.2 1.2 Myrcene9821166 2.3 2.1 2.2 2.1 2.3 2.0 Hexyl acetate99312730.20.10.20.10.5 1.2 a-Phellandrene9991171 2.6 3.0 2.5 3.0 3.5 2.3 p-Cymene101312760.30.20.50.30.10.6 Limonene b)10251207 5.6 5.4 5.4 5.8 5.9 5.9 b-Phellandrene b)1026122272.873.670.475.778.371.6 g-Terpinene105012500.30.3 1.40.10.10.2 Cryptone115716830.3–0.20.8– 2.1 Terpinen-4-ol116316050.60.40.90.2–0.1 Decanol125517680.3 1.20.8 1.20.2 1.6 Geranyl acetate13611762 1.2 1.6 2.1 1.8 1.5 1.9 Yield[%(w/w)] 1.2 2.9 2.60.8 2.4 2.4 a)Order of elution and percentages of components are given for the apolar column(BP-1),except for compounds with b).b)Percentages are given for the polar column(BP-20).

Chemical Variability.Aerial parts of57individual plants of Bupleurum fruticosum were collected in various places in Corsica(Fig.2)from July to September1997(20 samples)and from April(or July)to November2007(37samples).The fresh material was hydrodistilled and the oil samples were analyzed by GC(RI).Some samples, selected on the basis of their chromatographic profile,were submitted to GC/MS and/ or13C-NMR analysis.The57compositions were submitted to principal component analysis(PCA;Fig.3),and k-means partitioning was performed on all the terpene data with individual compounds expressed as a percentage.In PCA,the first two axes accounted for86.56and8.36%,respectively.Only one group emerged,although a few samples,characterized by a lower content of b-phellandrene and a higher content of sabinene,were present(Table5).

As expected,b-phellandrene was by far the major component.Indeed,its content varied between59.0and80.3%for all samples,except one(49.1%).Moreover,its content was higher than70.0%for72%of the samples.Among other monoterpenes, sabinene accounted for more than10%in10samples out of57and reached29.2%in one sample.Limonene(4.0–9.2%)was always present at appreciable content,while a-pinene and b-pinene reached punctually8.8and6.6%,respectively.

Conclusions.–It appears from that study on a large group of samples(57), harvested in various locations of a well-defined area,that Bupleurum fruticosum

Fig.2.Sampling locations of Bupleurum fruticosum..:Main city;&:Sampling location:1,Barchetta;2, Caporalino;3,Cardo;4,Casanova de Venaco;5,Casella;6,Cateraggio;7,Erbalunga;8,Luri;9, Marinca;10,Meria;11,Morsiglia;12,Nonza;13,Patrimonio;14,Pino;15,Ponte Leccia;16,Ponte Novo;17,Saint-Pierre de Venaco;18,San Nicolau;19,Sisco;20,Tolare;21,Tolla. growing wild in the island of Corsica produces a b-phellandrene-rich oil(more than 70%for72%of the samples).For comparison purposes,it could be noted that the highest percentage of b-phellandrene reported so far in the literature reached64.5% (Italy).No sample dominated by g-terpinene,a-pinene,b-pinene,or sabinene was detected.Leaves and stems produced oils with similar composition.The composition of flower oil,although dominated by b-phellandrene,exhibited a small content of the

phenylpropanoid estragole (Fig.1).The composition of oils extracted from aerial parts varied only slightly,qualitatively and quantitatively,along the physiological cycle of the plant.However,the yield was higher during and after the flowering stage.Finally,oil produced by SFME had a similar composition than that isolated by conventional hydrodistillation,but the yield was drastically lower.

Fig.3.Principal component analysis scatter plot of 57samples of Bupleurum fruticosum essential oil from

Corsica Table 5.Chemical Variability (major components)[%]of 57Samples of Bupleurum fruticosum Essential Oil .Results are given as mean value (Mean)with standard deviation (SD),minimum content (Min),

and maximum content (Max).Components a )Mean SD Min Max a -Pinene 2.1 1.18 1.68.8Sabinene 5.3 5.670.629.2b -Pinene 0.5 1.030.3 6.6Myrcene

1.50.88 1.8

2.5a -Phellandrene 2.60.49 1.7

3.6p -Cymene 1.1 1.090.1 1.1Limonene b )

5.60.63 4.09.2b -Phellandrene b )72.5

6.0949.180.3g -Terpinene 0.60.73tr c ) 3.1Cryptone 0.40.48– 3.1Terpinen-4-ol 0.60.57tr c ) 2.1Estragole 0.40.320 1.7Decanol

1.00.500.2

2.5Geranyl acetate

1.6

0.45

0.6

2.5

)Order of elution and percentages of components are given for the apolar column (BP-1),except for compounds with b ).b )Percentages are given for the polar column (BP-20).c )tr:traces.

The authors are indebted to the Collectivite′Territoriale de Corse(ARP Ressources Naturelles)and to the European Community Program INTERREG3Corsica-Sardinia-Tuscany for partial financial support.We also thank Mr.Alessandri from the society U Mandriolu,Corsica,for the gift of an oil sample and Mrs.Hugot for the identification of the plant material.

Experimental Part

Plant Material.To differentiate oils isolated from various parts of the plant,leaves,stems,and flowers of Bupleurum fruticosum L.were collected from two plants growing wild near Corte,in the centre of Corsica,in September2005,and they were submitted independently to hydrodistillation.Aerial parts of two individual plants were collected in May,in July or September,and in November2005to follow the evolution of the composition before,during,and after flowering.Finally,aerial parts of individual plants were collected from July to September1997(20samples)and2007(37samples),in the following locations:Barchetta,Caporalino,Cardo,Casanova de Venaco,Casella,Cateraggio,Erbalunga,Luri, Marinca,Meria,Morsiglia,Nonza,Patrimonio,Pino,Ponte Leccia,Ponte Novo,Saint-Pierre de Venaco, San Nicolau,Sisco,Tolare,and Tolla(Fig.2).It could be noted that B.fruticosum is abundant in the so-called Alpine Corsica and it is scarce in the other part,called Crystalline Corsica [14].Identification of the species was confirmed by https://www.sodocs.net/doc/004793600.html,etitia Hugot,Office de l Environnement de la Corse.

Essential-Oil Isolation and Fractionation.The oil sample used for detailed analysis was supplied by the society U Mandriolu,Corsica.It was obtained by vapor distillation in an industrial apparatus,with plants harvested during July2005,near Corte.The bulk sample(1.030g)was submitted to column chromatography(CC)on silica gel(SiO2).Elution with a solvent gradient of increasing polarity (pentane/Et2O100:0–0:100)led to four fractions:Fr.1(812mg)and Fr.2(18mg)eluted with pentane, Fr.3(115mg)eluted with pentane/Et2O97:3,and Fr.4(86mg)eluted with Et2O.

Otherwise,the fresh material(aerial parts or various organs of the plant)was submitted to hydrodistillation for3h,using a Clevenger-type apparatus.The yield of oil was expressed as%(w/w)vs. fresh material.Solvent-free microwave extraction(SFME)was carried out using a Milestone DryDist microwave apparatus.The temp.was monitored and controlled by feedback to the microwave power regulator.Extraction time,30min;power,500W.

Analytical GC.GC Analysis was carried out with a Perkin-Elmer Autosystem GC apparatus equipped with FID and two fused-silica cap.columns(50m?0.22mm i.d.,film thickness0.25m m),BP-1 (poly(dimethylsiloxane))and BP-20(poly(ethyleneglycol)).The oven temp.was programmed from60 to2208at28/min and then held isothermal at2208for20min;injector temp.,2508;detector temp.,2508; carrier gas,He(0.8ml/min);split,1:60.The relative proportions of the oil constituents were expressed as percentage obtained by peak area normalization,without using correcting factors.Retention indices(RI) were determined rel.to the retention times of a series of n-alkanes with linear interpolation(Target Compounds software from Perkin-Elmer).

GC/MS Analysis.The essential oils were analyzed with a Perkin-Elmer TurboMass detector (quadrupole),directly coupled to a Perkin-Elmer Autosystem XL,equipped with a fused-silica cap. column(60m?0.22mm i.d.,film thickness0.25m m),Rtx-1(polydimethyl siloxane).Carrier gas,He (1ml/min);split,1:80;injection vol.,0.2m l;injector temp.,2508;oven temp.programmed from608to 2308at28/min and then held isothermal at2308for45min;ion-source temp.,1508;energy ionization, 70eV;electron ionization mass spectra were acquired over the mass range35–350Da.

NMR Analysis.All13C-NMR spectra were recorded in CDCl3,with chemical shifts referred to int. Me4Si.Spectra of mixtures(essential oil or CC fractions)isolated in2007were recorded on a Bruker AVANCE400Fourier Transform spectrometer,operating at100.63MHz,equipped with a5-mm probe, with the following parameters:pulse width,4m s(flip angle458);acquisition time,2.7s for128K data table with a spectral width of24000Hz(240ppm);CPD mode decoupling;digital resolution,0.183Hz/ pt.The number of accumulated scans was3000for each sample(ca.40mg of the sample in0.5ml of CDCl3).Spectra of oil samples isolated in1997were recorded on a Bruker AC200Fourier Transform spectrometer operating at50.323MHz,equipped with a10-mm probe,with the following parameters: pulse width,5.0m s(flip angle458);spectral width,12500Hz(250ppm);CPD mode decoupling.The

number of accumulated scans was 3000–5000for each sample (200mg of the oil in 2ml of CDCl 3).An exponential multiplication of the free induction decay with line broadening of 1.0Hz was applied before Fourier transformation.

H-,13C-,and 2D-NMR Spectra (DEPT,HSQC,HMBC)of pure compounds were recorded using Bruker microprograms (Bruker AVANCE 400).For T 1measurements,the longitudinal relaxation delays of the 13C-nuclei (T 1values)were determined for each protonated C-atom of b -phellandrene (Fig.1)and for the two CH 2groups of diglyme (bis(2-methoxyethyl)ether)by the inversion-recovery method,using the standard sequence 1808-t -908-D 1,with a relaxation delay D 1of 10–50s (Table 6).Each delay of inversion (t )was thus taken into account for the computation of the corresponding T 1using Eqn.1.

I P ?I 0tp áe àt =T 1

(1)

For the quant.determination of b -phellandrene in the oil sample of the society U Mandriolu ,a quantitative spectrum was acquired using the inverse gated decoupling sequence with the following parameters:pulse width,8.5m s (flip angle 908);acquisition time,2.7s for 128K data table with a spectral width of 24000Hz (240ppm);repetition time 40s (5?longest T 1of protonated C-atoms,Table 6);digital resolution,0.183Hz/pt.The number of accumulated scans was 256(52mg of the oil sample in 0.5ml of CDCl 3).Diglyme was used as int.standard (T 1of CH 2group C-atoms,3.8s).The amount,m P in mg,of b -phellandrene was determined using Eqn.2:

m P ?

2A P áM P ám D

D D

(2)

A P ,mean values of the integrals of the protonated C-atoms of b -phellandrene;A D ,mean values of the integrals of the two CH 2groups of diglyme used as int.standard;M P and M D ,molecular weight [g/mol]of b -phellandrene and diglyme,resp.;m D ,weight of diglyme [mg].Experimental data:A P ,1.711;A D ,1.006;M P ,136.23g/mol;M D ,134.17g/mol;m D ,10.0mg;m EO ,52.0mg;m P ,34.2;m P %?65.8.

Identification of Components.Identification of the individual components was based:i )on comparison of their GC retention indices (RI )on polar and apolar columns with those of authentic compounds and literature data [15][16],ii )on computer matching with commercial mass spectral libraries [17–19]and comparison of spectra with literature data [15][20][21],and iii )on comparison of the signals in the 13C-NMR spectra of the mixtures with those of reference spectra compiled in the laboratory spectral library,with the help of a laboratory-made software [22–24].In the investigated samples,individual components were identified by NMR at contents as low as 0.5%.

Preparation of Cinnamyl Esters.To a soln.of cinnamyl alcohol (276mg,2.05mmol or 519mg,3.87mmol,resp.)in 30ml CH 2Cl 2and Et 3N (326mg,3.22mmol or 780mg,7.74mmol,resp.)cooled to

Table 6.1H-,13C-,and 2D-NMR Data of b -Phellandrene .At 400/100MHz,respectively,in CDCl 3;d in

ppm,J in Hz.Position d (C)T 1[s]DEPT d (H)

1143.72n.m.a )C –

2129.627.9CH 6.16(dd ,J ?9.8,2.7)3134.157.9CH 5.75(br.d ,J ?9.8)442.167.4CH 2.00–2.10(m )

525.81 4.0CH 2 1.77(dq ,J ?12.7,4.0),1.43(tdd ,J ?12.7,10.0,3.8)630.25 4.2CH 2 2.44(dt ,J ?14.9,3.8),2.29(dd ,J ?14.9,12.7)7109.95 4.6CH 2 4.76–4.78(m ),4.73–4.75(m )831.997.5CH 1.60–1.70(m )919.54 3.5CH 30.94(d ,J ?6.7)10

19.73

3.5

CH 3

0.91(d ,J ?6.7)

)n.m.:Not measured

08,a soln.of2-methylbutyryl chloride(518mg,4.29mmol)or isovaleryl chloride(978mg,7.74mmol)in CH2Cl2(30ml)was added dropwise.The mixture was stirred until r.t.was reached and then refluxed for 3h.The mixture was poured into200ml of cold H2O.After decantation,the org.phase was separated, washed twice with H2O,dried(Na2SO4),and concentrated in vacuum.The crude esters were purified by CC(SiO2).Yields(not optimized)were80and79%,resp.

Cinnamyl2-Methylbutyrate.1H-NMR:7.37–7.40(m,2H);7.29–7.33(m,2H);7.23–7.26(m,1H);

6.65(d,J?15.9,1H);6.28(dt,J?15.9,6.4,1H);4.74(dd,J?6.4,1.2,2H);2.43(sext.,J?

7.0,1H);

1.66–1.77(m,1H);1.44–1.55(m,1H);1.17(d,J?7.0,3H);0.92(t,J?7.4,3H).13C-NMR:176.56; 136.32;133.96;128.61;128.02;126.61;123.48;64.79;41.12;26.83;16.64;11.65.

Cinnamyl Isovalerate.1H-NMR:7.37–7.40(m,2H);7.30–7.35(m,2H);7.25–7.28(m,1H);6.65(d, J?15.8,1H);6.28(dt,J?15.8,6.4,1H);4.74(dd,J?6.4,1.4,2H);2.24(d,J?7.3,2H);2.08–2.19(m, 1H);0.97(d,J?6.7,6H).13C-NMR:172.96;136.28;134.08;128.61;128.04;126.61;123.37;64.79;43.44;

25.75;22.44.

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Version1.7,Perkin-Elmer Corporation,Norwalk,CT,1999.

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Received October17,2008

The way常见用法

The way 的用法 Ⅰ常见用法： 1)the way+ that 2)the way + in which（最为正式的用法） 3)the way + 省略（最为自然的用法）举例：I like the way in which he talks. I like the way that he talks. I like the way he talks. Ⅱ习惯用法：在当代美国英语中，the way用作为副词的对格，“the way+ 从句”实际上相当于一个状语从句来修饰整个句子。 1)The way =as I am talking to you just the way I’d talk to my own child. He did not do it the way his friends did. Most fruits are naturally sweet and we can eat them just the way they are—all we have to do is to clean and peel them. 2）The way= according to the way/ judging from the way The way you answer the question, you are an excellent student. The way most people look at you, you’d think trash man is a monster. 3）The way =how/ how much No one can imagine the way he missed her. 4）The way =because

The way的用法及其含义(二)

The way的用法及其含义（二）二、the way在句中的语法作用 the way在句中可以作主语、宾语或表语： 1.作主语 The way you are doing it is completely crazy.你这个干法简直发疯。 The way she puts on that accent really irritates me. 她故意操那种口音的样子实在令我恼火。The way she behaved towards him was utterly ruthless. 她对待他真是无情至极。 Words are important, but the way a person stands, folds his or her arms or moves his or her hands can also give us information about his or her feelings. 言语固然重要,但人的站姿,抱臂的方式和手势也回告诉我们他(她)的情感。 2.作宾语 I hate the way she stared at me.我讨厌她盯我看的样子。 We like the way that her hair hangs down.我们喜欢她的头发笔直地垂下来。 You could tell she was foreign by the way she was dressed. 从她的穿著就可以看出她是外国人。 She could not hide her amusement at the way he was dancing. 她见他跳舞的姿势，忍俊不禁。 3.作表语 This is the way the accident happened.这就是事故如何发生的。 Believe it or not, that's the way it is. 信不信由你, 反正事情就是这样。 That's the way I look at it, too. 我也是这么想。 That was the way minority nationalities were treated in old China. 那就是少数民族在旧中

(完整版)the的用法

定冠词the的用法：定冠词the与指示代词this ,that同源,有“那(这)个”的意思,但较弱,可以和一个名词连用,来表示某个或某些特定的人或东西. (1)特指双方都明白的人或物 Take the medicine.把药吃了. (2)上文提到过的人或事 He bought a house.他买了幢房子. I've been to the house.我去过那幢房子. (3)指世界上独一无二的事物 the sun ,the sky ,the moon, the earth (4)单数名词连用表示一类事物 the dollar 美元 the fox 狐狸或与形容词或分词连用,表示一类人 the rich 富人 the living 生者 (5)用在序数词和形容词最高级,及形容词等前面 Where do you live?你住在哪? I live on the second floor.我住在二楼. That's the very thing I've been looking for.那正是我要找的东西. (6)与复数名词连用,指整个群体 They are the teachers of this school.(指全体教师) They are teachers of this school.(指部分教师) (7)表示所有,相当于物主代词,用在表示身体部位的名词前 She caught me by the arm.她抓住了我的手臂. (8)用在某些有普通名词构成的国家名称,机关团体,阶级等专有名词前 the People's Republic of China 中华人民共和国 the United States 美国 (9)用在表示乐器的名词前 She plays the piano.她会弹钢琴. (10)用在姓氏的复数名词之前,表示一家人 the Greens 格林一家人(或格林夫妇) (11)用在惯用语中 in the day, in the morning... the day before yesterday, the next morning... in the sky... in the dark... in the end... on the whole, by the way...

“the way+从句”结构的意义及用法

“tｈｅwａｙ+从句”结构的意义及用法首先让我们来看下面这个句子: Ｒead the foｌloｗｉnｇpassagｅａnd talkａbout ｉt wi ｔh your classmaｔes．Try tｏｔeｌl whaｔyｏu thiｎk ｏf Tom aｎd ｏｆｔhe ｗay the chiｌｄrenｔrｅated ｈim. 在这个句子中，ｔhe waｙ是先行词,后面是省略了关系副词that或in whｉch的定语从句。下面我们将叙述“the ｗaｙ+从句”结构的用法。 1.tｈe wａy之后，引导定语从句的关系词是tｈat而不是hoｗ,因此，<<现代英语惯用法词典＞＞中所给出的下面两个句子是错误的：Ｔhｉs is ｔｈeｗayｈowｉtｈａppened. This is the way how he ａlwａｙs treats me. 2．在正式语体中,thaｔ可被in which所代替;在非正式语体中，ｔhat则往往省略。由此我们得到theｗay后接定语从句时的三种模式：1) tｈe ｗaｙ＋ｔhａt-从句２）the way +ｉn whiｃh－从句3) the ｗay +从句例如：Ｔｈe way(in whiｃh ，thａt) ｔhｅｓｅｃomｒade ｓloｏｋａｔｐrobｌems is wrong．这些同志看问题的方法

不对。Ｔｈｅｗａy(that ,ｉn ｗhiｃh)yoｕ’ｒe doinｇit is comple ｔeｌy crａzy.你这么个干法,简直发疯。 Wｅａdmiｒｅd him for thｅｗay ｉｎｗhｉch he fａｃeｓdiｆficultieｓ． Waｌlａｃe ａｎd Ｄarwiｎｇreed ｏn the way ｉｎwhi ｃh ｄｉfｆｅrｅnt forms ｏf life had ｂegｕn.华莱士和达尔文对不同类型的生物是如何起源的持相同的观点。 Thｉs is ｔｈe ｗaｙ（tｈａｔ) hｅdｉd it. I lｉkeｄｔhe waｙ(ｔhat) ｓｈeｏｒganized ｔhe ｍeetｉng． 3.theｗay(tｈat)有时可以与hｏw(作“如何”解）通用。例如： That’s tｈe ｗaｙ(tｈaｔ) shｅspoke. = Tｈat’s how shｅspoke.

way 用法

表示“方式”、“方法”，注意以下用法： 1.表示用某种方法或按某种方式，通常用介词in(此介词有时可省略)。如： Do it (in) your own way. 按你自己的方法做吧。 Please do not talk (in) that way. 请不要那样说。 2.表示做某事的方式或方法，其后可接不定式或of doing sth。如： It’s the best way of studying [to study] English. 这是学习英语的最好方法。 There are different ways to do [of doing] it. 做这事有不同的办法。 3.其后通常可直接跟一个定语从句(不用任何引导词)，也可跟由that 或in which 引导的定语从句，但是其后的从句不能由how 来引导。如：我不喜欢他说话的态度。正：I don’t like the way he spoke. 正：I don’t like the way that he spoke. 正：I don’t like the way in which he spoke. 误：I don’t like the way how he spoke. 4.注意以下各句the way 的用法： That’s the way (=how) he spoke. 那就是他说话的方式。 Nobody else loves you the way(=as) I do. 没有人像我这样爱你。 The way (=According as) you are studying now, you won’tmake much progress. 根据你现在学习情况来看，你不会有多大的进步。 2007年陕西省高考英语中有这样一道单项填空题： ——I think he is taking an active part insocial work. ——I agree with you_____. A、in a way B、on the way C、by the way D、in the way 此题答案选A。要想弄清为什么选A，而不选其他几项，则要弄清选项中含way的四个短语的不同意义和用法，下面我们就对此作一归纳和小结。一、in a way的用法表示：在一定程度上，从某方面说。如： In a way he was right.在某种程度上他是对的。注：in a way也可说成in one way。二、on the way的用法 1、表示：即将来(去)，就要来(去)。如： Spring is on the way.春天快到了。 I'd better be on my way soon.我最好还是快点儿走。 Radio forecasts said a sixth-grade wind was on the way.无线电预报说将有六级大风。 2、表示：在路上，在行进中。如： He stopped for breakfast on the way.他中途停下吃早点。 We had some good laughs on the way.我们在路上好好笑了一阵子。 3、表示：(婴儿)尚未出生。如： She has two children with another one on the way.她有两个孩子，现在还怀着一个。 She's got five children，and another one is on the way.她已经有5个孩子了，另一个又快生了。三、by the way的用法

The way的用法及其含义(一)

The way的用法及其含义（一）有这样一个句子：In 1770 the room was completed the way she wanted. 1770年，这间琥珀屋按照她的要求完成了。 the way在句中的语法作用是什么？其意义如何？在阅读时，学生经常会碰到一些含有the way 的句子，如：No one knows the way he invented the machine. He did not do the experiment the way his teacher told him.等等。他们对the way 的用法和含义比较模糊。在这几个句子中，the way之后的部分都是定语从句。第一句的意思是，“没人知道他是怎样发明这台机器的。”the way的意思相当于how；第二句的意思是，“他没有按照老师说的那样做实验。”the way 的意思相当于as。在In 1770 the room was completed the way she wanted.这句话中，the way也是as的含义。随着现代英语的发展，the way的用法已越来越普遍了。下面，我们从the way的语法作用和意义等方面做一考查和分析：一、the way作先行词，后接定语从句以下3种表达都是正确的。例如：“我喜欢她笑的样子。” 1. the way+ in which +从句 I like the way in which she smiles. 2. the way+ that +从句 I like the way that she smiles. 3. the way + 从句(省略了in which或that) I like the way she smiles. 又如：“火灾如何发生的，有好几种说法。” 1. There were several theories about the way in which the fire started. 2. There were several theories about the way that the fire started.

way 的用法

way 的用法【语境展示】 1. Now I’ll show you how to do the experiment in a different way. 下面我来演示如何用一种不同的方法做这个实验。 2. The teacher had a strange way to make his classes lively and interesting. 这位老师有种奇怪的办法让他的课生动有趣。 3. Can you tell me the best way of working out this problem? 你能告诉我算出这道题的最好方法吗？ 4. I don’t know the way (that / in which) he helped her out. 我不知道他用什么方法帮助她摆脱困境的。 5. The way (that / which) he talked about to solve the problem was difficult to understand. 他所谈到的解决这个问题的方法难以理解。 6. I don’t like the way that / which is being widely used for saving water. 我不喜欢这种正在被广泛使用的节水方法。 7. They did not do it the way we do now. 他们以前的做法和我们现在不一样。【归纳总结】 ●way作“方法，方式”讲时，如表示“以……方式”，前面常加介词in。如例1； ●way作“方法，方式”讲时，其后可接不定式to do sth.，也可接of doing sth. 作定语，表示做某事的方法。如例2，例3；

the-way-的用法讲解学习

t h e-w a y-的用法

The way 的用法 "the way+从句"结构在英语教科书中出现的频率较高, the way 是先行词, 其后是定语从句.它有三种表达形式:1) the way+that 2)the way+ in which 3)the way + 从句(省略了that或in which),在通常情况下, 用in which 引导的定语从句最为正式,用that的次之,而省略了关系代词that 或 in which 的, 反而显得更自然,最为常用.如下面三句话所示,其意义相同. I like the way in which he talks. I like the way that he talks. I like the way he talks. 一.在当代美国英语中,the way用作为副词的对格,"the way+从句"实际上相当于一个状语从句来修饰全句. the way=as 1)I'm talking to you just the way I'd talk to a boy of my own. 我和你说话就象和自己孩子说话一样. 2)He did not do it the way his friend did. 他没有象他朋友那样去做此事. 3)Most fruits are naturally sweet and we can eat them just the way they are ----all we have to do is clean or peel them . 大部分水果天然甜润,可以直接食用,我们只需要把他们清洗一下或去皮.

way的用法总结大全

way的用法总结大全 way的用法你知道多少，今天给大家带来way的用法，希望能够帮助到大家，下面就和大家分享，来欣赏一下吧。 way的用法总结大全 way的意思 n. 道路,方法,方向,某方面 adv. 远远地，大大地 way用法 way可以用作名词 way的基本意思是“路,道,街,径”,一般用来指具体的“路,道路”,也可指通向某地的“方向”“路线”或做某事所采用的手段,即“方式,方法”。way还可指“习俗,作风”“距离”“附近,周围”“某方面”等。 way作“方法,方式,手段”解时,前面常加介词in。如果way前有this, that等限定词,介词可省略,但如果放在句首,介词则不可省略。

way作“方式,方法”解时,其后可接of v -ing或to- v 作定语,也可接定语从句,引导从句的关系代词或关系副词常可省略。 way用作名词的用法例句 I am on my way to the grocery store.我正在去杂货店的路上。 We lost the way in the dark.我们在黑夜中迷路了。 He asked me the way to London.他问我去伦敦的路。 way可以用作副词 way用作副词时意思是“远远地,大大地”,通常指在程度或距离上有一定的差距。 way back表示“很久以前”。 way用作副词的用法例句 It seems like Im always way too busy with work.我工作总是太忙了。 His ideas were way ahead of his time.他的思想远远超越了他那个时代。 She finished the race way ahead of the other runners.她第一个跑到终点,远远领先于其他选手。 way用法例句

the_way的用法大全教案资料

t h e_w a y的用法大全

The way 在the way+从句中, the way 是先行词, 其后是定语从句.它有三种表达形式:1) the way+that 2)the way+ in which 3)the way + 从句(省略了that或in which),在通常情况下, 用in which 引导的定语从句最为正式,用that的次之,而省略了关系代词that 或 in which 的, 反而显得更自然,最为常用.如下面三句话所示,其意义相同. I like the way in which he talks. I like the way that he talks. I like the way he talks. 如果怕弄混淆，下面的可以不看了另外，在当代美国英语中,the way用作为副词的对格,"the way+从句"实际上相当于一个状语从句来修饰全句. the way=as 1)I'm talking to you just the way I'd talk to a boy of my own. 我和你说话就象和自己孩子说话一样. 2)He did not do it the way his friend did. 他没有象他朋友那样去做此事. 3)Most fruits are naturally sweet and we can eat them just the way they are ----all we have to do is clean or peel them . 大部分水果天然甜润,可以直接食用,我们只需要把他们清洗一下或去皮. the way=according to the way/judging from the way 4)The way you answer the qquestions, you must be an excellent student. 从你回答就知道,你是一个优秀的学生. 5)The way most people look at you, you'd think a trashman was a monster. 从大多数人看你的目光中,你就知道垃圾工在他们眼里是怪物. the way=how/how much 6)I know where you are from by the way you pronounce my name. 从你叫我名字的音调中,我知道你哪里人. 7)No one can imaine the way he misses her. 人们很想想象他是多么想念她. the way=because 8) No wonder that girls looks down upon me, the way you encourage her. 难怪那姑娘看不起我, 原来是你怂恿的

the way 的用法

The way 的用法 "the way+从句"结构在英语教科书中出现的频率较高, the way 是先行词, 其后是定语从句.它有三种表达形式:1) the way+that 2)the way+ in which 3)the way + 从句(省略了that或in which),在通常情况下, 用in which 引导的定语从句最为正式,用that的次之,而省略了关系代词that 或in which 的, 反而显得更自然,最为常用.如下面三句话所示,其意义相同. I like the way in which he talks. I like the way that he talks. I like the way he talks. 一.在当代美国英语中,the way用作为副词的对格,"the way+从句"实际上相当于一个状语从句来修饰全句. the way=as 1)I'm talking to you just the way I'd talk to a boy of my own. 我和你说话就象和自己孩子说话一样. 2)He did not do it the way his friend did. 他没有象他朋友那样去做此事. 3)Most fruits are naturally sweet and we can eat them just the way they are ----all we have to do is clean or peel them . 大部分水果天然甜润,可以直接食用,我们只需要把他们清洗一下或去皮.

the way=according to the way/judging from the way 4)The way you answer the qquestions, you must be an excellent student. 从你回答就知道,你是一个优秀的学生. 5)The way most people look at you, you'd think a trashman was a monster. 从大多数人看你的目光中,你就知道垃圾工在他们眼里是怪物. the way=how/how much 6)I know where you are from by the way you pronounce my name. 从你叫我名字的音调中,我知道你哪里人. 7)No one can imaine the way he misses her. 人们很想想象他是多么想念她. the way=because 8) No wonder that girls looks down upon me, the way you encourage her. 难怪那姑娘看不起我, 原来是你怂恿的 the way =while/when(表示对比) 9)From that day on, they walked into the classroom carrying defeat on their shoulders the way other students carried textbooks under their arms. 从那天起,其他同学是夹着书本来上课,而他们却带着"失败"的思想负担来上课.

The way的用法及其含义(三)

The way的用法及其含义（三）三、the way的语义 1. the way=as（像） Please do it the way I’ve told you.请按照我告诉你的那样做。 I'm talking to you just the way I'd talk to a boy of my own.我和你说话就像和自己孩子说话一样。 Plant need water the way they need sun light. 植物需要水就像它们需要阳光一样。 2. the way=how（怎样，多么） No one can imagine the way he misses her.没人能够想象出他是多么想念她！ I want to find out the way a volcano has formed.我想弄清楚火山是怎样形成的。 He was filled with anger at the way he had been treated.他因遭受如此待遇而怒火满腔。That’s the way she speaks.她就是那样讲话的。 3. the way=according as （根据） The way you answer the questions, you must be an excellent student.从你回答问题来看，你一定是名优秀的学生。 The way most people look at you, you'd think a trash man was a monster.从大多数人看你的目光中,你就知道垃圾工在他们眼里是怪物。 The way I look at it, it’s not what you do that matters so much.依我看，重要的并不是你做什么。 I might have been his son the way he talked.根据他说话的样子，好像我是他的儿子一样。One would think these men owned the earth the way they behave.他们这样行动，人家竟会以为他们是地球的主人。

way的用法

一．Way：“方式”、“方法” 1.表示用某种方法或按某种方式 Do it (in) your own way. Please do not talk (in) that way. 2.表示做某事的方式或方法 It’s the best way of studying [to study] English.。 There are different ways to do [of doing] it. 3.其后通常可直接跟一个定语从句(不用任何引导词)，也可跟由that 或in which 引导的定语从句正：I don’t like the way he spoke. I don’t like the way that he spoke. I don’t like the way in which he spoke.误：I don’t like the way how he spoke. 4. the way 的从句 That’s the way (=how) he spoke. I know where you are from by the way you pronounce my name. That was the way minority nationalities were treated in old China. Nobody else loves you the way(=as) I do. He did not do it the way his friend did. 二．固定搭配 1. In a/one way：In a way he was right. 2. In the way /get in one’s way I'm afraid your car is in the way， If you are not going to help，at least don't get in the way. You'll have to move－you're in my way. 3. in no way Theory can in no way be separated from practice. 4. On the way (to……) Let’s wait a few moments. He is on the way Spring is on the way. Radio forecasts said a sixth-grade wind was on the way. She has two children with another one on the way. 5. By the way By the way，do you know where Mary lives? 6. By way of Learn English by way of watching US TV series. 8. under way 1. Elbow one’s way He elbowed his way to the front of the queue. 2. shoulder one’s way 3. feel one‘s way 摸索着向前走；We couldn’t see anything in the cave, so we had to feel our way out 4. fight/force one’s way 突破。。。而前进The surrounded soldiers fought their way out. 5.. push/thrust one‘s way（在人群中）挤出一条路He pushed his way through the crowd. 6. wind one’s way 蜿蜒前进 7. lead the way 带路，领路；示范 8. lose one‘s way 迷失方向 9. clear the way 排除障碍，开路迷路 10. make one’s way 前进，行进The team slowly made their way through the jungle.

the way的用法大全

在the way+从句中, the way 是先行词, 其后是定语从句.它有三种表达形式:1) the way+that 2)the way+ in which 3)the way + 从句(省略了that或in which),在通常情况下, 用in which 引导的定语从句最为正式,用that的次之,而省略了关系代词that 或in which 的, 反而显得更自然,最为常用.如下面三句话所示,其意义相同. I like the way in which he talks. I like the way that he talks. I like the way he talks. 如果怕弄混淆，下面的可以不看了另外，在当代美国英语中,the way用作为副词的对格,"the way+从句"实际上相当于一个状语从句来修饰全句. the way=as 1)I'm talking to you just the way I'd talk to a boy of my own. 我和你说话就象和自己孩子说话一样. 2)He did not do it the way his friend did. 他没有象他朋友那样去做此事. 3)Most fruits are naturally sweet and we can eat them just the way they are ----all we have to do is clean or peel them . 大部分水果天然甜润,可以直接食用,我们只需要把他们清洗一下或去皮. the way=according to the way/judging from the way 4)The way you answer the qquestions, you must be an excellent student. 从你回答就知道,你是一个优秀的学生. 5)The way most people look at you, you'd think a trashman was a monster. 从大多数人看你的目光中,你就知道垃圾工在他们眼里是怪物. the way=how/how much 6)I know where you are from by the way you pronounce my name. 从你叫我名字的音调中,我知道你哪里人. 7)No one can imaine the way he misses her. 人们很想想象他是多么想念她. the way=because 8) No wonder that girls looks down upon me, the way you encourage her. 难怪那姑娘看不起我, 原来是你怂恿的 the way =while/when(表示对比) 9)From that day on, they walked into the classroom carrying defeat on their shoulders the way other students carried textbooks under their arms.

“the-way+从句”结构的意义及用法知识讲解

“the way+从句”结构的意义及用法首先让我们来看下面这个句子： Read the following passage and talk about it with your classmates. Try to tell what you think of Tom and of the way the children treated him. 在这个句子中，the way是先行词，后面是省略了关系副词that 或in which的定语从句。下面我们将叙述“the way+从句”结构的用法。 1．the way之后，引导定语从句的关系词是that而不是how,因此，<<现代英语惯用法词典>>中所给出的下面两个句子是错误的：This is the way how it happened. This is the way how he always treats me. 2. 在正式语体中，that可被in which所代替；在非正式语体中，that则往往省略。由此我们得到the way后接定语从句时的三种模式：1) the way +that-从句2) the way +in which-从句3) the way +从句例如：The way(in which ,that) these comrades look at problems is wrong.这些同志看问题的方法不对。

The way(that ,in which)you’re doing it is completely crazy.你这么个干法，简直发疯。 We admired him for the way in which he faces difficulties. Wallace and Darwin greed on the way in which different forms of life had begun.华莱士和达尔文对不同类型的生物是如何起源的持相同的观点。 This is the way (that) he did it. I liked the way (that) she organized the meeting. 3.the way(that)有时可以与how(作“如何”解)通用。例如： That’s the way (that) she spoke. = That’s how she spoke. I should like to know the way/how you learned to master the fundamental technique within so short a time. 4．the way的其它用法：以上我们讲的都是用作先行词的the way，下面我们将叙述它的一些用法。

定冠词the的12种用法

定冠词the的12种用法定冠词the 的12 种用法，全知道?快来一起学习吧。下面就和大家分享，来欣赏一下吧。定冠词the 的12 种用法，全知道? 定冠词the用在各种名词前面，目的是对这个名词做个记号，表示它的特指属性。所以在词汇表中，定冠词the 的词义是“这个，那个，这些，那些”，可见，the 即可以放在可数名词前，也可以修饰不可数名词，the 后面的名词可以是单数，也可以是复数。定冠词的基本用法： (1) 表示对某人、某物进行特指，所谓的特指就是“不是别的，就是那个!”如： The girl with a red cap is Susan. 戴了个红帽子的女孩是苏珊。 (2) 一旦用到the，表示谈话的俩人都知道说的谁、说的啥。如：

The dog is sick. 狗狗病了。(双方都知道是哪一只狗) (3) 前面提到过的，后文又提到。如： There is a cat in the tree.Thecat is black. 树上有一只猫，猫是黑色的。 (4) 表示世界上唯一的事物。如： The Great Wall is a wonder.万里长城是个奇迹。(5) 方位名词前。如： thenorth of the Yangtze River 长江以北地区 (6) 在序数词和形容词最高级的前面。如： Who is the first?谁第一个? Sam is the tallest.山姆最高。但是不能认为，最高级前必须加the，如： My best friend. 我最好的朋友。 (7) 在乐器前。如： play the flute 吹笛子

Way的用法

Way用法 A:I think you should phone Jenny and say sorry to her. B:_______. It was her fault. A. No way B. Not possible C. No chance D. Not at all 说明：正确答案是A. No way，意思是“别想！没门！决不！” 我认为你应该打电话给珍妮并向她道歉。没门！这是她的错。再看两个关于no way的例句：（1）Give up our tea break? NO way! 让我们放弃喝茶的休息时间？没门儿！（2）No way will I go on working for that boss. 我决不再给那个老板干了。 way一词含义丰富，由它构成的短语用法也很灵活。为了便于同学们掌握和用好它，现结合实例将其用法归纳如下：一、way的含义 1. 路线

He asked me the way to London. 他问我去伦敦的路。 We had to pick our way along the muddy track. 我们不得不在泥泞的小道上择路而行。 2. （沿某）方向 Look this way, please. 请往这边看。 Kindly step this way, ladies and gentlemen. 女士们、先生们，请这边走。 Look both ways before crossing the road. 过马路前向两边看一看。 Make sure that the sign is right way up. 一定要把符号的上下弄对。 3. 道、路、街，常用以构成复合词 a highway（公路），a waterway（水路），a railway（铁路），wayside（路边）

way与time的特殊用法

way/time的特殊用法 1、当先行词是way意思为”方式.方法”的时候,引导定语从句的关系词有下列3种形式： Way在从句中做宾语 The way that / which he explained to us is quite simple. Way在从句中做状语 The way t hat /in which he explained the sentence to us is quite simple. 2、当先行词是time时,若time表示次数时,应用关系代词that引导定语从句,that可以省略; 若time表示”一段时间”讲时,应用关系副词when或介词at/during + which引导定语从句 1.Is this factory _______ we visited last year? 2.Is this the factory-------we visited last year? A. where B in which C the one D which 3. This is the last time _________ I shall give you a lesson. A. when B that C which D in which 4.I don’t like the way ________ you laugh at her. A . that B on which C which D as 5.He didn’t understand the wa y ________ I worked out the problem. A which B in which C where D what 6.I could hardly remember how many times----I’ve failed. A that B which C in which D when 7.This is the second time--------the president has visited the country. A which B where C that D in which 8.This was at a time------there were no televisions, no computers or radios. A what B when C which D that