全 文 ：天然产物研究与开发 NatProdResDev2009, 21:976-979
文章编号:1001-6880(2009)06-0976-04
ReceivedMay26, 2008;Accepted
FoundationItem:ThisresearchwassupportedbytheKnowledgeInno-
vationProgramofChineseAcademyofSciences(KZCX2-YW-216),
theNationalSupportivePlanProjectofScienceandTechnology
(2006BAB19B02), andtheHundredTalentsProgramofChineseA-
cademyofSciences.
＊CorespondenceauthorTel:86-20-89023013;E-mail:lixiang@scsio.
ac.cn
裂叶荆芥不同部位香精油组成研究
谢练武 1, 2 ,戴世鲲 1, 2 ,王广华 1, 2 ,张君增 3 ,陈敏捷 1, 2 ,李 翔 1＊
1中国科学院南海海洋研究所 广东省海洋药物重点实验室 , 广州 510301;
2中国科学院研究生院 , 北京 100049;3加拿大国家研究院营养科学与健康研究所 ,夏洛特敦 PEIC1A4P3
摘 要:采用水蒸气蒸馏法 ,分别从裂叶荆芥的叶 、茎和花三个不同部位提取香精油并进行气相色谱 /质谱分
析。结果发现 ,叶 、茎 、花的香精油分别含有 23、 29、26种组分。叶和花香精油的组成和含量基本相似 , 主要成分
是含量分别为 15.09%、14.51%的薄荷酮和 29.26%、31.36%的(+)-胡薄荷酮等单萜化合物以及含量分别为
17.09%、5.00%的 α-律草烯等倍半萜。而茎香精油的萜类化合物含量较低 , 含薄荷酮为 4.15%, (+)-胡薄荷
酮为 7.68%,但其乙酯含量相对较高 , 如 (E)-9-十六碳烯酸乙酯含量为 11.92%,异戊酸乙酯为 9.38%。
关键词:裂叶荆芥;香精油;组成
中图分类号:R932;Q946.91 文献标识码:A
CompositionofEssentialOilfromtheAerialPartofSchizonepetatenuifolia
XIELian-wu1, 2 , DAIShi-kun1, 2 , WANGGuang-hua1, 2 , ZHANGJun-zeng3 , CHENMin-jie1, 2 , LIXiang1＊
1SouthChinaSeaInstituteofOceanology, ChineseAcademyofSciences, Guangzhou510301 , China;
2GraduateUniversityoftheChineseAcademyofSciences, Beijing100049, China;
3InstituteforNutrisciencesandHealth, NationalResearchCouncilofCanada, CharlotetownPEIC1A4P3, Canada
Abstract:Schizonepetatenuifolia(Benth.)Briq.ofLabiataefamilyiswidelyusedasakeycomponentsoftraditional
ChinesemedicineinChina.Thecompositionsofessentialoilextractedbyhydrodistillationfromtheleaf, stemandfasci-
cledflower(spike)ofSchizonepetatenuifoliawereidentifiedusingGC/MS.Theleafoilcomprisedof23 components,
whilethestemandspikeoilcontained29and26components, respectively.Theconstituentsandtheirlevelofcontentsin
essentialoilextractedfromtheleafandspikeweresimilarwiththemajorcomponentsof(1)monoterpenes:menthone
(15.09% fromleafand14.51% fromspike), (2)(+)-pulegone(29.26% fromleafand31.36% fromspike)and
(3)sesquiterpene:α-humulene(17.09% fromleafand5.00% fromspike).Thestemoilcontainsahighercontentof
ethylesters[ ethyl-(E)-9-hexadecenoate, 11.92%;ethylisovalerate9.38%] andalowerlevelofmonoterpenes(men-
thoneof4.15% and(+)-pulegoneof7.68%)thantheleafandspikeoil.
Keywords:SchizonepetatenuifoliaLabiatae;essentialoil;composition
Introduction
TheplantSchizonepetatenuifolia(Benth.) Briq.
(JingjieinChinese)isamemberofLabiataefamily,
andmainlygrowsinSouthernandCentralChina.Itis
thedriedaerialpartincludingthespike, leafandstem
ofSchizonepetatenuifoliathatareoftenusedintradi-
tionalChinesemedicine(TCM)[ 1] .Withtheincreas-
inguseofherbalproducts, S.tenuifoliahasbeencom-
monlymarketedforthetreatmentofcommoncoldand
feverwithheadache, sorethroat[ 2] , alergicdermatitis,
pruritus[ 3] , andeczema[ 4] inTCM.Invitroandinvivo
studiesonitspharmacologicalactivitieshavealsobeen
carriedout[ 2-5] .Inaddition, thecarbonizedherbisrec-
ommendedandusedasaremedyforstoppingbleeding
duetoitshemostaticproperty[ 6] .Ithadbeenknown
thattheessentialoilsfrommanyaromaticplantand
herbpossessbioactivitysuchasantimicrobial[ 7] , anti-
fungal[ 8] andantioxidantproperties[ 9] .Soresearchon
DOI :10.16333/j.1001-6880.2009.06.024
compositionsofessentialoilfromTCMhadbecomein-
creasinglyimportant.Severalmajorcomponentsand
structuressuchasglycosides(schizonepetosideA, B,
C, DandE), schizonol, schizonodiol[ 10, 11] , volatileoils
(menthoneandpulegone)[ 12, 13] , andflavonoids[ 10] (di-
osmetin, hesperetin, andluteolin)havebeenisolated
andidentifiedfromS.tenuifolia.Althoughasmentioned
abovethatmanystudiesonitspharmacologicalactivi-
tieshavebeencariedout, butnodetailedanalysisof
theessentialoilfromitsspike, leafandstemhasbeen
reported.Therefore, aspartoffingerprintresearchon
S.tenuifolia, thepresentinvestigationsweredesignedto
identifythecompositionsoftheessentialoilsfromthe
leaf, stemandspikeofS.tenuifolia.
Experimental
Plantmaterialandextraction
Theaerialpartincludingthespikes, leavesandstems
ofS.tenuifoliawerecolectedfrommatureplants(in
anthesis)growinginHonganCounty, HubeiProvince,
China.Afterair-dried, about200geachofspikes, leav-
esandstemsweresubjectedtohydrodistilationin3L
boilingdistiledwaterwithanessentialoilcolector.
Theprocesswasperformeduntiltherewasnosignifi-
cantincreaseinvolumeofoilwithin6h, yielding2.92
gspikeoil, 1.56gleafoiland0.83 gstemoil.Aloil
samplesweredriedoveranhydroussodium sulphate
andstoredat10℃ intheabsenceoflight.
GC-MSanalysis
AnalysisofesentialoilextractemployedaThermo
FinniganTRACEgaschromatography(GC), equipped
withThermoFinniganTRACEMSplusandHP-5 silica
fusedcapilarycolumn(30 m ×0.25 mmi.d.with
0.25 μmmembranethickness, AgilentTechnology).
Splitlesssurgeinjectionof1 μLofextractwasmanual-
lyconducted.Theinjectorandthetransferlinetemper-
atureweremaintainedat250 ℃ and280 ℃, respec-
tively.Columntemperaturewasprogrammedfrom40℃
(holdfor1min)to100℃atarateof10℃/min, 100
℃ for2 min, folowedbyanincreaseto180 ℃ ata
rateof4.0℃/min, 180℃ for2min, thenincreasedto
280 ℃ atarateof5.0 ℃/min(holdfor8 min).Ul-
tra-purifiedheliumwasusedasthecarriergaswith
splitflow50mL/minfor2min, flowrateat1mL/min,
surgepressure300kPafor2min, andgassaverflow20
mL/minfor2min.
Massspectrawereacquiredattheelectronionization
(EI)modewithanelectronmultipliervoltageof2200
Vandanionizationvoltageof70 eV.Themassscan-
ningrangedbetweenm/z45 andm/z550 underscan
mode.
Identificationofcomponents
Identificationsofcomponentswereachievedbymatc-
hingtheirmassspectrawiththoseintheWILEY, MA-
INLIB, REPLIBandNISTDEMOlibrarieswithsimilar
index(SI) > 800 orwithpublishedMSdata
bank[ 14] .Thecomponentswereconfirmedbycomparing
theirKovatsretentionindiceswiththoseofauthentic
compounds.TheKovatsretentionindicesofthecompo-
nentsweredeterminedrelativetotheretentiontimesof
aseriesofn-alkanes.Quantificationwasperformedby
integrationoftheselectedionchromatogramsextracted
fromthetotalioncurrent.Quantitativedatawereob-
tainedfromthetotalioncurrentchromatogram(TIC)
peakareapercentageswithouttheuseofcorrectionfac-
tors.
ResultsandDiscussion
Theconstituentsoftheleafoil, thestemoilandthe
spikeoilofS.tenuifoliaweregiveninTable1, together
withexperimentalKovatsretentionindices(RI)on
HP-5 column, includingtheirpercentagepeakareas.
Distinctqualitativeandquantitativediferenceswere
observedinthreekindsofessentialoilsstudied.Major
compoundsover5% ofeachoftheessentialoilswere
describedbelow.
Therewere18 terpenoidsofthe23volatilecompounds
fromtheleafoil, makingup86.92% ofthetotaloil
composition.Majortermnoidcompoundswere(+)-
pulegone(29.26%), α-humulene(17.09%)and
menthone(15.09%).Non-terpenoidsidentifiedfrom
theleafoilonlyrepresented13.08% oftheoil.Terpe-
noidswereonegroupofinterestingcomponentsbecause
oftheirbroadbioactivities, notablyantibacterialand
977Vol.21 XIELian-wu, etal:CompositionofEssentialOilfromtheAerialPartofSchizonepetatenuifolia
Table1 CompositionofessentialoilfromSchizonepetatenuifoliaa
Compound RIb Leaf Stem Spike Methodofidentificationc
Ethylisovalerate 859 1.28 9.38 - RI, MS
3-Octanone 968 0.21 0.23 0.38 MS
1-Octen-3-one 982 0.05 0.43 0.21 MS
Myrcene 991 0.23 0.16 0.35 RI, MS
3-Octanol 993 0.85 1.12 0.31 MS
Limonene 1022 2.98 3.00 4.50 RI, MS
1-Ocrenyl, acetate 1048 2.26 1.84 2.15 RI, MS
cis-p-Menth-2, 8-dien-1-ol 1123 - 1.31 1.53 RI, MS
Menthone 1157 15.09 4.15 14.51 RI, MS
Menthofuran 1165 2.43 2.53 2.95 RI, MS
Isopulegone 1187 1.49 1.11 2.29 RI, MS
(E, E)-5, 7-Dodecadiene 1201 - 4.36 5.08 RI, MS
(+)Pulegone 1225 29.26 7.68 31.36 RI, MS
(-)Pulegone 1236 4.21 2.49 1.90 RI, MS
4, 5-Epoxy-carane 1290 0.51 0.40 - RI, MS
Cinerone 1292 - - 0.60 RI, MS
2-Undecenal＊ 1350 - 1.68 1.96 MS
(E)-β-Farnesene 1458 1.73 1.02 2.19 RI, MS
α-Acoradiene 1463 2.38 2.12 2.47 RI, MS
(Z, E)-α-Farnesene 1491 1.31 1.65 0.93 RI, MS
Cadina-1, 4-diene 1532 0.25 0.23 0.49 RI, MS
α-Humulene 1558 17.09 21.42 5.00 RI, MS
Cedrenol 1696 0.05 0.28 0.32 MS
6, 10, 14-Trimethyl-2-pentadecanone 1849 0.22 0.43 0.29 RI, MS
Hexadecanoicacid 1995 0.36 0.16 0.09 RI, MS
Ethyl-(E)-9-hexadecenoate 2027 3.98 11.92 2.78 RI, MS
Ethyl, linoleate 2155 - 1.48 1.73 RI, MS
Farnesylacetate＊ 2283 0.22 0.29 0.32 RI, MS
Tetracosane 2400 - 0.11 - RI, MS
Heptacosane 2700 - 0.14 - RI, MS
Note:ashowspercentageofcompoundsofesentialoils;bKovatsretentionindicesonHP-5 GCcolumn;CCompoundswereidentifiedbycomparison
withtheauthenticstandardsonthefolowingcriteria:RIonHP-5GCcolumnandmassspectraattheelectronionizationmode;＊cis-transisomernotiden-
tified.
antioxidantproperties.
Although29 compoundsfromthestemoilwereana-
lyzed, onlytwocompoundsα-humulene(21.42%)
and(+)-pulegone(7.68%)werepredominatedones
in19terpenoidscomponents.Theothertwomajorcom-
ponentethyl-(E)-9-hexadecenoate(11.92%)and
ethylisovalerate(9.38%)werebothethylesters.The
contentofalterpenoidsofstemoil(58.73%)was
30% lessthanthatoftheleafoil.
Theanalysisofthespikeoilrevealedthat(+)-pule-
gone(31.36%), menthone(14.51%), (E, E)-5, 7-
dodecadiene(5.08%)andα-humulene(5.00%)as
themajorcomponents.Thecontentof17 terpenoids
from26 compoundsidentifiedfromthespikeoilwas
978 NatProdResDev Vol.21
similartothatofleafoil, makingup81.37% oftheto-
talextract.
Amongthe6 maincomponentsmentionedabove, 4 of
them, suchasmenthone, (+)-pulegone, α-humulene,
andethyl-(E)-9-hexadecenoatepresentedinalthree
kindsofoils.Ethylisovaleratewasnotdetectedinthe
spikeoil, withonly1.28% ethylisovalerateintheleaf
oilcomparedwiththatofthestemoil.Inaddition, the
leafoildidnotcontain(E, E)-5, 7-dodecadiene,
whereasitshowedbothinstemoil(4.36%)and
spikeoil.Thestemoilwascharacteristicofhavinga
highercontentofethylesters(ethyl-(E)-9-hexade-
cenoateandethylisovalerate)andalowercontentof
monoterpenes(menthone4.15% and(+)-pulegone
7.68%), whencomparedwithleafandspikeoil.The
constituentsandcontentsofessentialoilextractedfrom
theleavesandspikesweresimilar, withthemajorcom-
ponentsbeingmonoterpenes(menthoneand(+)-
pulegone)andsesquiterpene(α-humulene).
Acknowledgments Thisresearchwassupportedby
theKnowledgeInnovationProgramofChineseAcademy
ofSciences(KZCX2-YW-216)andNationalSupport-
ive Plan Project of Science and Technology
(2006BAB19B02).Wealsothankthefundingofthe
HundredTalentsProgramofChineseAcademyofSci-
encestoXL.
References
1 GuoJX, XiePS, QiP, etal.PharmacopoeiaofthePeople s
RepublicofChina.Beijing:ChemicalIndustryPress, 1997.
102-103.
2 ChangHM, ButPPH.PharmacologyandApplicationsofChi-
neseMateriaMedica.Singapore:WorldScientific, 1986.855-
856.
3 TohdaC, KakiharaY, KomatsuK, etal.Inhibitoryefectsof
methanolextractsofherbalmedicinesonsubstanceP-in-
duceditch-scratchresponse.BiolPharmBull, 2000, 23:599-
601.
4 KirbyAJ, SchmidtRJ.TheantioxidantactivityofChinese
herbsforeczemaandofplaceboherbs.JEthnopharmacol,
1997, 56:103-108.
5 ZhuYP.ChineseMateriaMedica—Chemistry, Pharmacolo-
gy, andApplications.Amsterdam:HarwoodAcademic, 1998,
60-61.
6 DingAW.HemostaticeffectofSchizonepetatenuifoliabefore
andaftercarbonization.ZhongYaoTongBao, 1986, 11:23-
25.
7 StojanovicG, AsakawaY, PalicR, etal.Compositionand
antimicrobialactivityofAchilleaclavennaeandAchileaho-
losericeaessentialoils.FlavourFragrJ, 2005, 20:86-88.
8 Lis-BalchinM, DeansSG, EagleshamE.Relationshipbe-
tweenbioactivityandchemicalcompositionofcommerciales-
sentialoils.FlavourFragrJ, 1998, 13:98-104.
9 BarataMT, DamienHJ, DeansDSG, etal.Antimicrobialand
antioxidantpropertiesofsomecommercialessentialoils.Fla-
vourFragrJ, 1998, 13:235-244.
10 SasakiH, TaguchiH, EndoT, etal.TheconstituentsofSchi-
zonepetatenuifoliaBriq:I.Structuresoftwonewmonoterpene
glucosides, schizonepetosidesAandB.ChemPharmBull,
1981, 29:1636-1643.
11 OshimaY, TakataS, HikinoH.Schizonodiol, schizonol, and
schizonepetosidesDandE, monoterpenoidsofSchizonepeta
tenuifoliaspikes.PlantaMed, 1989, 55:179-180.
12 ZhengHZ, DongZH, SheJ.ModernStudyofTraditionalChi-
neseMedicine.Vol4.Beijing:BeijingXueYuanPress,
1997.3072-3081.
13 ChenY, JiangZH, TianJK.GC-MSanalysisofvolatileoil
fromtheearofSchizonepetatenifoliaBriq.JChinMedMat.
2006, 29:140-142.
14 AdamsRP.IdentificationofEssentialOilComponentsbyGas
Chromatography/MassSpectroscopy.Allured:CarolStream,
IL, 1995.
979Vol.21 XIELian-wu, etal:CompositionofEssentialOilfromtheAerialPartofSchizonepetatenuifolia