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Chemical Composition and Antimicrobial Activities of Essential Oils of Laggera pterodonta Collected in Four Different Locations in Yunnan, China*

云南不同产地臭灵丹精油化学成分及抗菌活性



全 文 :云南不同产地臭灵丹精油化学成分及抗菌活性∗
顾健龙1ꎬ2ꎬ Guy S􀆰 S􀆰 NJATENG3ꎬ 李志坚1ꎬ 张红霞1ꎬ
代  琴1ꎬ2ꎬ 杜芝芝1∗∗
(1 中国科学院昆明植物研究所植物化学与西部植物资源持续利用国家重点实验室ꎬ 云南 昆明  650201ꎻ
2 中国科学院大学ꎬ 北京  100049ꎻ 3 Dschang大学自然科学系微生物学与
抗菌物质实验室ꎬ P.O. Box 67 Dschangꎬ Cameroon)
摘要: 采用水蒸气蒸馏的方法ꎬ 对采自云南 4 个不同地区 (昆明ꎬ 丽江ꎬ 普洱ꎬ 新平) 的臭灵丹叶子进
行挥发油提取ꎬ 并利用 GC ̄MS 和 GC ̄FID 气相色谱联用技术分析其化学组成ꎬ 分别从中鉴定出 39、 37、
33、 44个化合物ꎮ 鉴定的化合物各占挥发油总量的 93􀆰 32% (昆明)、 80􀆰 57% (丽江)、 92􀆰 24% (普洱)
和 93􀆰 85% (新平)ꎮ 研究结果表明ꎬ 采自这四个地区植物样品提取所得挥发油化学组成不尽相同: 昆明产
臭灵丹挥发油富含芳香族化合物 (38􀆰 06%)ꎻ 而从丽江和普洱样品中获得的挥发油化学成分以倍半萜
(分别为 19􀆰 89%和 44􀆰 65%) 和氧化倍半萜 (分别为 40􀆰 85%和 35􀆰 11%) 为主ꎻ 非氧化单萜和非氧化倍半
萜化合物 (分别为 42􀆰 23%和 33􀆰 25%) 则是新平产臭灵丹挥发油的主要化合物类型ꎮ 同时ꎬ 对这些不同
产地的臭灵丹挥发油也进行了抗菌活性测试ꎮ 从以上实验研究结果推测环境差异是影响臭灵丹挥发油化学
组成差异的重要因素ꎬ 而不同的化学组成可能是导致 4种样品抗菌敏感程度不同的原因ꎮ
关键词: 臭灵丹ꎻ 挥发油ꎻ GC ̄MSꎻ 抗菌活性
中图分类号: Q 946            文献标识码: A              文章编号: 2095-0845(2014)01-116-07
Chemical Composition and Antimicrobial Activities of Essential
Oils of Laggera pterodonta Collected in Four Different
Locations in Yunnanꎬ China∗
GU Jian ̄Long1ꎬ2ꎬ NJATENG Guy S􀆰 S􀆰 3ꎬ LI Zhi ̄Jian1ꎬ ZHANG Hong ̄Xia1ꎬ
DAI Qin1ꎬ2ꎬ DU Zhi ̄Zhi1∗∗
(1 State Key Laboratory of Phytochemistry and Plant Resources in West Chinaꎬ Kunming Institute of Botanyꎬ Chinese Academy
of Sciencesꎬ Kunming 650201ꎬ Chinaꎻ 2 University of Chinese Academy of Sciencesꎬ Beijing 100049ꎬ Chinaꎻ
3 Laboratory of Microbiology and Antimicrobial Substancesꎬ Faculty of Scienceꎬ
University of Dschangꎬ P.O. Box 67 Dschangꎬ Cameroon)
Abstract: Essential oils obtained by hydrodistillation from leaves of Laggera pterodonta collected from four different
locations (Kunmingꎬ Lijiangꎬ Puer and Xinping) in Yunnanꎬ Chinaꎬ were analyzed using GC ̄MS and GC ̄FID. The
number of compounds identified in each sample was 39ꎬ 37ꎬ 33 and 44ꎬ respectivelyꎬ representing 93􀆰 32% (Kun ̄
ming)ꎬ 80􀆰 57% (Lijiang)ꎬ 92􀆰 24% (Puer) and 93􀆰 85% (Xinping) of total essential oils. Chemical compositions
of essential oils differed between sample locations: thusꎬ those from Kunming were rich in benzenoid compounds
(38􀆰 06%) while those from Lijiang and Puer were largely dominated by sesquiterpenes (19􀆰 89% and 44􀆰 65% re ̄
spectively) and sesquiterpenes oxide (40􀆰 85% and 35􀆰 11%ꎬ respectively)ꎬ and those from Xinping contained a
植 物 分 类 与 资 源 学 报  2014ꎬ 36 (1): 116~122
Plant Diversity and Resources                                    DOI: 10.7677 / ynzwyj201413017

∗∗
基金项目: 云南省自然科学基金项目———两种滇产特色香料植物的应用基础研究 (2009CD111)
Author for correspondenceꎻ E ̄mail: duzhizhi@ mail. kib. ac. cn
Received date: 2013-02-01ꎬ Accepted date: 2013-03-22
作者简介: 顾健龙 (1988-) 男ꎬ 在读硕士研究生ꎬ 主要从事云南特色香料植物挥发性成分研究ꎮ
high proportion of monoterpene hydrocarbons and sesquiterpene hydrocarbons (42􀆰 23% and 33􀆰 25% respectively)
(75􀆰 48%). The results of tests on the antimicrobial activities of essential oils indicated that chemical composition
was affected by environmental variation causing differences in sensitivity to microbes among samples.
Key words: Laggera pterodontaꎻ Essential oilꎻ GC ̄MSꎻ Antimicrobial activity
  The genus Laggera (family Compositae) has a ̄
round 20 speciesꎬ which mainly distribute in tropical
Africa and Asia. Laggera alata and L􀆰 pterodonta are
the only two species in China which are employed as
traditional herbal medicines because of their anti ̄in ̄
flammatory and antibacterial activities (New Medical
School of Jiansuꎬ 1985). L􀆰 pterodonta (DC.) Benth
which called ‘Chou Ling Dan’ as it produces stimu ̄
lous odor is widely distributed in the Southwestern
Chinaꎬ especially in Yunnan Province.
Previous work revealed that sesquiterpenes are
the major components from the plant and many new
compounds were isolated from it during the last two
decades (Li et al.ꎬ 2007ꎻ Zhao et al.ꎬ 1997aꎬ b).
Other types of terpenoids and flavonoids were also i ̄
solated from aerial part of the plant (Yang et al.ꎬ
2007). In preliminary investigationsꎬ total flavonids
from L􀆰 pterodonta exhibited anti ̄inflammatory activity
(Wu et al.ꎬ 2006) and antineoplastic activity (Cao et
al.ꎬ 2010). Pterodontic acid and pterodondiol isola ̄
ted from the plant showed antimicrobial activity as
well (Yang et al.ꎬ 2007). Essential oil was also im ̄
portant secondary metabolites with bioactivities in
L􀆰 pterodonta on which had fewer researches (Wei et
al.ꎬ 1992ꎻ Xin et al.ꎬ 1999)ꎬ and none of these re ̄
searches involved pharmacological part to the best of
our knowledge. Some of essential oils in genus Lag ̄
gera were proved to have good antimicrobial and free
radical scavenging activities such as L􀆰 decurrens
(Mothana et al.ꎬ 2011). Essential oils collected in
different places were found to have different clinical
applications and the chemical constitutes of these es ̄
sential oils are diverse as well. These phenomena
mean that difference of oils’ chemical constitutes may
lead to different pharmacological activities. In the
present studyꎬ the essential oils derived from dry
leaves of L􀆰 pterodonta in four locations were analyzed
by GC ̄MS and their antimicrobial activities against
several bacterial and fungal strains were tested.
1  Material and methods
1􀆰 1  Plant material
Aerial parts of L􀆰 pterodonta were collected from
Kunmingꎬ Lijiangꎬ Puer and Xinping of Yunan
Provinceꎬ China during July and August in 2011 and
2012. All these samples were air ̄dried in the shade
then store in cool and dark place in ziplock bags be ̄
fore use. The plant samples were identified by Dr.
Liu En ̄de from Herbarium of Kunming Institute of
Botanyꎬ Chinese Academy of Sciences.
1􀆰 2  Isolation of essential oils
Air dried aerial parts (100 g) were subjected to
hydrodistillation for 4 h using the standard apparatus
described in the Chinese pharmacopoeia ( China
Pharmacopeia Commissionꎬ 2010). The essential oil
was separated from aqueous phase produced during
distillation and dried over anhydrous Na2 SO4 . The
yields of essential oils were calculated as % based on
the dry weight of the plant material. The essential
oils were stored at 4° in airtight sample bottles. They
were diluted in hexane to 2% concentration prior to
GC ̄FID and GC ̄MS analysis.
1􀆰 3  GC and GC ̄MS analysis
Essential oils were analyzed on Agilent 7890A
gas chromatograph with a flame ionization detector
(FID). Analysis of the essential oils were also carried
out using an Agilent 7890A gas chromatograph e ̄
quipped with a Agilent 5975C mass spectrometerꎬ fit ̄
ted with a HP ̄5 (5% diphenyl polysiloxane) capil ̄
lary column (50 m × 0􀆰 2 mm i􀆰 d.ꎬ 0􀆰 33 μm film
thickness)ꎬ with helium carrier gasꎬ initial head
pressure 46􀆰 3 psi (1􀆰 7 mL􀅰min-1). The FID detec ̄
tor temperature was held at 300 ℃ and the MSD
transfer line at 250 ℃ꎬ with the injector set at 250℃.
7111期    GU Jian ̄Long et al.: Chemical Composition and Antimicrobial Activities of Essential Oils of Laggera pterodonta 􀆺   
The oven temperature was programmed isothermal at 50
℃ꎬ then rising from 50 ℃ to 280 ℃ at 2 ℃ / min and
hold for 10 min at 280 ℃. The splitless ̄injection mode
was selectedꎬ and the ionization was carried out in the
mass spectrometer under vacuum by electron impact
(70 eV). Data were acquired and processed using MSD
ChemStation software (scan modeꎬ m / z 30-500).
The identification of the components was based
on i ) the comparison of their retention indices
(RIs) determined relatively to the tR values of a se ̄
ries of n ̄alkanes ( C7 - C30 ) with those data from
NIST 08 databaseꎬ ii) the comparison of fragmenta ̄
tion patterns in the mass spectra with those data from
NIST 08 database. Compound could be identified
when both of them were matched well.
1􀆰 4  Microbial strains
The antibacterial activity of essential oils from 4
locations were evaluated using nine laboratory con ̄
trol strains of bacteria obtained from the American
Type Culture Collection (Rockvilleꎬ MDꎬ USA): Gram ̄
positive bacteria Staphylococcus aureus (ATCC25922)ꎬ
Enterococcus faecalis ( ATCC 10541)ꎬ and Gram ̄
negative bacteria: Escherichia coli (ATCC 8739)ꎬ
E􀆰 coli (ATCC 10536)ꎬ E􀆰 coli (ATCC 11775)ꎬ En ̄
terobacter aerogenes (ATCC 13048)ꎬ Providencia stu ̄
artii ( ATCC 29916 )ꎬ Pseudomonas aeruginosa
(ATCC 27853)ꎬ Salmonella typhi (ATCC 6539).
Two dermatophytesꎬ one from “ Ecole Nationale
Vétérinaire d’ Aford” in Franceꎬ Trichophyton ajeloi
(E 1501) and one clinical isolate Trichophyton ter ̄
restreꎻ four strains of yeast including Candida albi ̄
cans ( ATCC1663)ꎬ Candida glabrata ( IP 35)ꎬ
Cryptococcus neoformans (IP95026)ꎬ Candida guilli ̄
mondii in which two IP strains from the “ Institute
Pasteur” (Parisꎬ France) and one clinical isolate.
Stock cultures were maintained at 4 ℃ on slopes
of Muller Hinton Agar for bacteria or on Sabouraud
Dextrose Agar for fungi and were activated for oneꎬ
two or fifteen days respectively for bacteriaꎬ yeasts
and dermatophytes before use in the experiment.
1􀆰 5  Antimicrobial activity
A broth micro ̄dilution method was used to de ̄
termine the minimum inhibitory concentration (MIC)
and minimum bactericidal concentration (MBC) ac ̄
cording to the National Committee for Clinical Labo ̄
ratory Standards ( NCCLSꎬ 2001). All tests were
performed in Mueller Hinton broth (MHB). The in ̄
ocula of the bacterial strains were prepared from 24 h
old cultures and suspensions were adjusted to 0􀆰 5
McFarland standard turbidity. The standardized inoc ̄
ulum was diluted five times to achieve a final inocu ̄
lum concentration of approximately 107 CFU / mL.
The samples were dissolved in 10% dimethylsulfox ̄
ide (DMSO) and diluted to the highest concentra ̄
tions (1 mg􀅰mL-1). Further serial dilutions of the
extracts were performed to reach a final concentra ̄
tion range between 1 000 and 7􀆰 8 μg􀅰mL-1 . For ev ̄
ery experimentꎬ a sterility check ( volume fraction
10% aqueous DMSO and medium)ꎬ negative control
(volume fraction 10% aqueous DMSOꎬ medium and
inocula) and positive control (volume fraction 10%
aqueous DMSOꎬ mediumꎬ inoculums and rifampicin
ranging from 50 to 0􀆰 39 μg􀅰mL-1) was included. All
assays were performed in triplicate. After incubation
at 37 ℃ for 24 hꎬ growth was monitored colorimet ̄
rically using iodonitrotetrazolium chloride (INT).
All concentrations at which no visible colour
change were considered as inhibitory concentrations
and the lowest of these concentrations was considered
as the MIC. The microbicidal concentrations was de ̄
termined by adding 50 μL aliquots of the preparations
(without INT)ꎬ which did not show any visible colour
change after incubation during MIC assaysꎬ into 150
μL of essential oil free MHB. These preparations were
further incubated at the above mentioned temperature
and period. Laterꎬ the microorganism growth was re ̄
vealed as indicated above. The smallest concentration
at which no colour change was observed was consid ̄
ered as the minimal bactericidal concentration (MBC).
The assay was carried out in triplicate.
MIC values were determined using broth dilution
techniques as described by the Clinical and Laborato ̄
ry Standards Institute (CLSIꎬ formerly National Com ̄
mittee for Clinical and Laboratory Standards ) for
811                                  植 物 分 类 与 资 源 学 报                            第 36卷
yeasts (M27 ̄A2) (NCCLSꎬ 2002a) as well for fila ̄
mentous fungi (M38 ̄A) (NCCLSꎬ 2002b) in micro ̄
titers of 96 wells with slight modifications. All tests
were performed in Sabouraud Dextrose broth (SDB).
The two ̄fold serial dilution in concentration of the es ̄
sential oil (500-3􀆰 9 μg􀅰mL-1) was prepared in Sab ̄
ouraud Dextrose Broth (SDB) for yeast and dermato ̄
phytes. The contents were incubated at 37 ℃ for 48 h
for yeasts and at 28 ℃ for 5 days for dermatophytes.
The minimal fungicidal concentration (MFC) was re ̄
garded as the lowest concentration of test sample
which did not produce a colour or turbidity change.
2  Results and discussion
2􀆰 1   Chemical components of L􀆰 pterodonta es ̄
sential oils from 4 locations
The essential oils of L􀆰 pterodonta were obtained
from the leaves by hydrodistillaionꎬ affording yellowish
oils in 0􀆰 15%ꎬ 0􀆰 16%ꎬ 0􀆰 16%ꎬ 0􀆰 16% yieldsꎬ re ̄
spectivelyꎬ from dry plant materials collected in Kun ̄
ming (KM)ꎬ Lijiang (LJ)ꎬ Puer (PE) and Xinping
(XP) locations.
GC ̄MS analyses led to the identification of 39ꎬ
37ꎬ 33 and 44 components in the essential oil of 4
locationsꎬ identified by comparing their RI values
with literature values ( Adamsꎬ 2007 ) and their
mass spectra with NIST08 MS library. The volatile
constituents are listed in Table 1 according to their
elution order on an apolar HP ̄5 MS capillary col ̄
umn. The main constituents in KM oil were 1 ̄Meth ̄
yl ̄2ꎬ 5 ̄dimethoxy ̄4 ̄isopropyl benzene (36􀆰 75%)ꎬ
α ̄humulene ( 10􀆰 12%)ꎬ β ̄pinene ( 9􀆰 97%)ꎬ γ ̄
Eudesmol ( 8􀆰 99%)ꎬ β ̄caryophyllene ( 5􀆰 64%).
XP oil showed a different compositionꎬ since β ̄pi ̄
nene (30􀆰 42%)ꎬ α ̄humulene (9􀆰 89%)ꎬ δ ̄terpin ̄
eol (7􀆰 95%) and β ̄bisabolene (5􀆰 18%) were the
main constituents. The LJ and PE oils were domina ̄
ted by sesquiterpenes and sesquiterpenes oxide com ̄
ponentsꎬ with β ̄Caryophyllene ( LJ 16􀆰 08%ꎬ PE
32􀆰 71%) and γ ̄Eudesmol (LJ 20􀆰 32%ꎬ PE 19􀆰 37%)
were the major constituents. The total identified com ̄
pounds from the 4 essential oil samples amounted to
KM 93􀆰 32%ꎬ LJ 80􀆰 57%ꎬ PE 92􀆰 24% and XP
93􀆰 85% of the total oil composition.
Table 1  Chemical composition of the essential oils obtained from Laggera pterodonta collected in 4 locations
Compound name RI1 a)
Peak area / %
Kunming Lijiang Puer Xinping
Compound name RI1 a)
Peak area / %
Kunming Lijiang Puer Xinping
Tricyclene 926  ̄  ̄  ̄ 0􀆰 47 3 ̄methylene ̄
α ̄Pinene 933  ̄  ̄  ̄ 0􀆰 56 Ethanoneꎬ 1 ̄(1ꎬ 1122  ̄ 0􀆰 39  ̄  ̄
β ̄Pinene 975 9􀆰 97  ̄  ̄ 30􀆰 42  4 ̄dimethyl ̄3 ̄
3 ̄Octanone 984 0􀆰 23  ̄  ̄  ̄ cyclohexen ̄1 ̄yl) ̄
Myrcene 989 0􀆰 63  ̄  ̄ 1􀆰 06 m ̄Methylacetophenone 1133  ̄ 0􀆰 20  ̄  ̄
α ̄Phellandrene 1004 0􀆰 48  ̄  ̄ 0􀆰 22 1 ̄Methyl ̄2 ̄ methylene ̄3ꎬ 1159  ̄  ̄  ̄ 0􀆰 33
α ̄Terpinene 1016 0􀆰 88  ̄  ̄ 1􀆰 38 5 ̄divinylcyclohexane
o ̄Cymene 1024 0􀆰 61  ̄  ̄ 0􀆰 15 Tricyclo[5􀆰 2􀆰 1􀆰 0(2ꎬ6)] 1162 1􀆰 03  ̄  ̄  ̄
β ̄Phellandrene 1029 0􀆰 17  ̄  ̄ 0􀆰 23 dec ̄3 ̄eneꎬ 4 ̄ethyl ̄
1ꎬ 8 ̄Cineol 1033 1􀆰 11 0􀆰 19  ̄ 0􀆰 87 δ ̄Terpineol 1163  ̄ 7􀆰 38 0􀆰 39 7􀆰 95
Benzeneacetaldehyde 1044 0􀆰 28  ̄  ̄  ̄ 3ꎬ 6 ̄Dimethyl ̄2ꎬ 1170  ̄ 0􀆰 28  ̄  ̄
Ocimene 1046 0􀆰 09  ̄  ̄ 2􀆰 63 3ꎬ 3aꎬ 4ꎬ 5ꎬ 7α ̄
γ ̄Terpinene 1058 2􀆰 12 1􀆰 33 0􀆰 03 2􀆰 55 hexahydrobenzofuran
Terpinolene 1088 0􀆰 54 2􀆰 55  ̄ 0􀆰 59 Terpinen ̄4 ̄ol 1181 3􀆰 60  ̄  ̄  ̄
3ꎬ 4 ̄dimethyl ̄2ꎬ 4ꎬ 1098  ̄  ̄  ̄ 1􀆰 63 α ̄Terpineol 1193 0􀆰 26 0􀆰 53 0􀆰 11 2􀆰 76
6 ̄Octatriene Methyl salicylate 1197 0􀆰 21  ̄  ̄  ̄
Nonanal 1101  ̄  ̄ 0􀆰 04  ̄ Myrtenol 1201  ̄ 0􀆰 29  ̄  ̄
2 ̄Nonen ̄1 ̄ol 1103 0􀆰 27  ̄  ̄  ̄ neoiso ̄Menthol 1207  ̄  ̄ 0􀆰 03 0􀆰 16
Cyclohexaneꎬ 2 ̄ 1115 0􀆰 21  ̄  ̄  ̄ trans ̄Carveol 1212  ̄ 0􀆰 26  ̄  ̄
ethenyl ̄1ꎬ 1 ̄dimethyl ̄ p ̄Mentha ̄6ꎬ 8 ̄ dien ̄2 ̄ one 1227  ̄ 0􀆰 42  ̄  ̄
9111期    GU Jian ̄Long et al.: Chemical Composition and Antimicrobial Activities of Essential Oils of Laggera pterodonta 􀆺   
Table 1 continued
Compound name RI1 a)
Peak area / %
Kunming Lijiang Puer Xinping
Compound name RI1 a)
Peak area / %
Kunming Lijiang Puer Xinping
Methyl thymyl ether 1233 0􀆰 33  ̄ 0􀆰 06  ̄ (+) ̄Epi ̄bicycloses ̄ 1531 0􀆰 31  ̄  ̄  ̄
1 ̄methoxy ̄4 ̄methyl ̄ 1242 0􀆰 12  ̄ 0􀆰 03  ̄ quiphellandrene
2 ̄(1 ̄methylethyl) ̄ Wieland ̄Michler ketone 1531  ̄ 3􀆰 71  ̄  ̄
Benzenev Eudesma ̄3ꎬ 7(11) ̄diene 1543  ̄  ̄ 0􀆰 12  ̄
6ꎬ 7 ̄Dimethyl ̄1ꎬ 2ꎬ 1271  ̄ 1􀆰 77  ̄  ̄ Elemol 1553  ̄  ̄  ̄ 0􀆰 26
3ꎬ 5ꎬ 8ꎬ 8α ̄ Germacrene B 1557 0􀆰 16  ̄ 0􀆰 62 1􀆰 05
hexahydronaphthalene Spathulenol 1569  ̄ 0􀆰 73  ̄  ̄
Lavandulyl acetate 1286  ̄  ̄  ̄ 0􀆰 10 Caryophyllene oxide 1594 0􀆰 65 3􀆰 83 2􀆰 99 1􀆰 64
Carvacrol 1290 0􀆰 07  ̄  ̄  ̄ 2 ̄Naphthalenemethanol 1598  ̄ 0􀆰 68  ̄  ̄
Eugenol 1340 0􀆰 30 1􀆰 04 0􀆰 06 0􀆰 16 Humulene epoxide II 1602  ̄ 3􀆰 21  ̄  ̄
3 ̄ Allyl ̄6 ̄ methoxyphenol 1353  ̄ 0􀆰 65  ̄  ̄ γ ̄Eudesmol 1616 8􀆰 99 20􀆰 32  19􀆰 37   ̄
Copaene 1380  ̄  ̄ 0􀆰 14 1􀆰 17 Cedrelanol 1632  ̄ 0􀆰 73  ̄ 0􀆰 20
β ̄Elemene 1387 0􀆰 59  ̄ 0􀆰 05 0􀆰 23 α ̄Eudesmol 1638 0􀆰 12 2􀆰 77 0􀆰 79  ̄
β ̄Bourbonene 1394 0􀆰 08  ̄  ̄  ̄ p ̄Hexylacetophenone 1640  ̄  ̄ 0􀆰 46 0􀆰 32
β ̄Copaene 1395  ̄  ̄ 1􀆰 08 3􀆰 93 Eudesm ̄4(14) ̄en ̄11 ̄ol 1644  ̄ 0􀆰 38  ̄  ̄
α ̄Cedrene 1406  ̄  ̄  ̄ 0􀆰 29 Torreyol 1649  ̄  ̄ 0􀆰 43  ̄
2 ̄Allyl ̄1ꎬ 4 ̄dimethoxy ̄ 1425  ̄ 0􀆰 37  ̄  ̄ Valerianol 1656  ̄  ̄ 2􀆰 32 0􀆰 13
3 ̄methyl ̄benzene Ledene oxide ̄(II)∗ 1661  ̄ 0􀆰 46  ̄  ̄
β ̄Caryophyllene 1429 5􀆰 64 16􀆰 08  32􀆰 71  3􀆰 77 Cubenol 1661  ̄  ̄ 0􀆰 52  ̄
1 ̄Methyl ̄2ꎬ 5 ̄ 1431 36􀆰 75  2􀆰 94 11􀆰 27   ̄ β ̄Bisabolol 1672 2􀆰 51 3􀆰 08 3􀆰 93 1􀆰 32
dimethoxy ̄4 ̄ Cadalene 1683  ̄  ̄ 0􀆰 08  ̄
isopropyl benzene α ̄Bisabolol 1690  ̄  ̄ 0􀆰 04 2􀆰 09
Aromadendrene 1437  ̄ 0􀆰 15  ̄  ̄ Guaiac acetate 1710  ̄  ̄ 4􀆰 41  ̄
trans ̄α ̄Bergamotene 1439  ̄  ̄  ̄ 1􀆰 44 6 ̄Isopropenyl ̄4ꎬ 8α ̄ 1722  ̄ 0􀆰 24 0􀆰 23  ̄
trans ̄Geranylacetone 1451  ̄  ̄  ̄ 0􀆰 42 dimethyl ̄1ꎬ 2ꎬ 3ꎬ 5ꎬ 6ꎬ
(6Z) ̄7ꎬ 11 ̄Dimethyl ̄ 1455  ̄  ̄  ̄ 0􀆰 48 7ꎬ 8ꎬ 8α ̄octahydro ̄
3 ̄methylene ̄1ꎬ 6ꎬ naphthalen ̄2 ̄ol
10 ̄dodecatriene 2 ̄(4αꎬ8 ̄Dimethyl ̄ 1771  ̄ 0􀆰 72  ̄  ̄
β ̄Santalene 1457 0􀆰 15  ̄  ̄  ̄ 1ꎬ 2ꎬ 3ꎬ 4ꎬ 4αꎬ 5ꎬ
α ̄Humulene 1466 10􀆰 12  1􀆰 48 8􀆰 35 9􀆰 89 6ꎬ 7 ̄octahydro ̄
Eudesma ̄4(14)ꎬ 1476  ̄ 0􀆰 20  ̄  ̄ naphthalen ̄2 ̄yl) ̄
11 ̄diene prop ̄2 ̄en ̄1 ̄ol
2 ̄Isopropenyl ̄4αꎬ 8 ̄ 1481  ̄  ̄ 0􀆰 12 0􀆰 55 Hexahydrofarnesyl 1821  ̄ 0􀆰 45  ̄  ̄
dimethyl ̄1ꎬ 2ꎬ 3ꎬ 4ꎬ acetone
4aꎬ 5ꎬ 6ꎬ 7 ̄octahyd ̄ ( ̄) ̄Isolongifololꎬ 1837 0􀆰 96  ̄  ̄  ̄
ronaphthalene acetate
β ̄Ionone 1491  ̄ 0􀆰 32  ̄  ̄ Phytol 2088  ̄ 0􀆰 23  ̄  ̄                                                                                       
Eremophilene 1491  ̄  ̄ 0􀆰 24 2􀆰 02 Total 93􀆰 32  80􀆰 56  92􀆰 23  93􀆰 85                                                                                        
α ̄Muurolene 1492 0􀆰 87  ̄ 0􀆰 40 0􀆰 48 Monoterpene 16􀆰 73  3􀆰 88 0􀆰 03 42􀆰 23 
α ̄Chamigren 1495 0􀆰 27  ̄  ̄  ̄ hydrocarbons
( ̄) ̄Zingiberene 1496  ̄  ̄  ̄ 0􀆰 37 Oxygenated 5􀆰 47 10􀆰 25  0􀆰 56 12􀆰 25 
α ̄Selinene 1498 0􀆰 15  ̄ 0􀆰 44 0􀆰 45 monoterpenes
Valencene 1500  ̄  ̄  ̄ 1􀆰 08 Sesquiterpene 18􀆰 34  19􀆰 89  44􀆰 65  33􀆰 25 
Cadina ̄1(10)ꎬ 4 ̄diene 1509  ̄ 0􀆰 21  ̄  ̄ hydrocarbons
β ̄Bisabolene 1512  ̄  ̄  ̄ 5􀆰 18 Oxygenated 14􀆰 72  40􀆰 85  35􀆰 11  5􀆰 62
Isolongifolan ̄8 ̄ol 1516 1􀆰 49  ̄  ̄  ̄ sesquiterpenes
Cadina ̄3ꎬ 9 ̄diene 1527  ̄  ̄ 0􀆰 38 0􀆰 87 Phenolic ether 38􀆰 06  5􀆰 69 11􀆰 88  0􀆰 48
a) RI: Retention indices determined relative to n ̄alkanes (C7-C30) on a HP ̄5 MS column
021                                  植 物 分 类 与 资 源 学 报                            第 36卷
2􀆰 2  Antimicrobial activities of L􀆰 pterodonta es ̄
sential oils from 4 locations
The essential oils were tested against several
bacterial and fungal strainsꎬ and the results are sum ̄
marized in Tables 2 and 3. The antimicrobial activi ̄
ties were evaluated by broth microdilution method on
the basis of minimum inhibitory concentration (MIC)
and minimum bactericidal concentration (MBC) or
minimal fungicidal concentration (MFC).
The different compositions of the 4 essential oils
are likely responsible for the different activities
found against bacteria and fungi. The KMꎬ LJ and
PE samples have moderate activity on some gram ̄
negative bacteriumꎬ such as Pseudomonas aerugino ̄
sa (MIC = 500 μg􀅰mL-1)ꎬ Escherichia coli (MIC
250 μg􀅰mL-1)ꎬ and Enterobacter aerogenes (MIC =
125 μg􀅰mL-1 to 250 μg􀅰mL-1). Howeverꎬ XP es ̄
sential oil was less sensitive to most of bacteria
strains than the other three samples we tested. XP oil
had only weak inhibitory activities against some fun ̄
gal strains (Table 3).
The antimicrobial activity may be related to the
presence of constituents like caryophyllene which is
known to posses activity against Staphylococcus au ̄
reusꎬ Candida albican ( Su and Hoꎬ 2012)ꎻ β ̄Pi ̄
neneꎬ which is known to have antibacterial activity
on Enterococcus faecalisꎬ Escherichia coliꎬ Pseudo ̄
monas aeruginosaꎬ Staphylococcus aureus ( Dorman
and Deansꎬ 2008 )ꎻ and γ ̄Eudesmolꎬ which is
known to have antimicrobial activity against Pseudo ̄
monas aeruginosaꎬ Staphylococcus aureus and Candi ̄
da albicans (Costa et al.ꎬ 2008). Caryophyllene ox ̄
ide and terpinen ̄4 ̄ol were also reported having good
effect on Enterobacter aerogenes (Dorman and Deansꎬ
2008ꎬ Skaltsa et al.ꎬ 2003). All the tested essential
oils have strong activity against Enterobacter aero ̄
genes (125 μg􀅰mL-1 to 250 μg􀅰mL-1) which indi ̄
cates some of the same components presented in the
4 oils were relate to their antibacterial activities of
the bacteria.
Table 2  Antibacterial activities of the essential oils obtained from Laggera pterodonta collected in 4 locations
Microorganims and Source No.
EO Kunming
MIC MBC
EO Lijiang
MIC MBC
EO Puer
MIC MBC
EO Xinping
MIC MBC
Rifampicin
MIC MBC
Pseudomonas aeruginosa ATCC 27853 500 >500 500 >500 500 >500 500 >500 25    50   
Escherichia coli ATCC 8739 500 >500 500 >500 500 >500 500 >500 0.09 6.25
Escherichia coli ATCC 10536 250 >500 250 >500 250 >500 >500 >500 0.19 0.78
Escherichia coli ATCC 11775 >500 >500 >500 >500 >500 >500 >500 >500 0.39 1.56
Enterococus faecalis ATCC10541 500 >500 500 >500 500 >500 >500 >500 0.19 1.56
Staphylococcus aureus ATCC 25922 >500 >500 >500 >500 500 >500 >500 >500 0.19 0.78
Enterobacter aerogene ATCC 13048 125 250 250 250 125 125 125 125 0.19 0.19
Providencia stuartii ATCC 29916 >500 >500 500 >500 >500 >500 >500 >500 0.09 0.19
Salmonella typhi ATCC 6539 500 >500 500 500 250 500 500 >500 0.09 6.25
Table 3  Antifungal activities of the essential oils obtained from Laggera pterodonta collected in 4 locations
Microoganisms
EO Kunming
MIC MFC
EO Lijiang
MIC MFC
EO Puer
MIC MFC
EO Xinping
MIC MFC
amphotericin B
MIC MFC
Trichophyton ajeloi (E 1501) 250 500 250 250 250 500 250 250 25    50   
Trichophyton terrestre 500 500 250 500 250 500 500 500 6.25 50   
Candida albicans (ATCC 1663) >500  >500  >500  25    >50   
Candida glabrata (CIP 35) 250 250 125 125 250 250 250 250 1.56 12.5 
Candida guilimondii 250 250 125 125 250 250 250 250 6.25 12.50
Cryptococcus neoformans (CIP95026) 250 250 250 250 250 250 250 500 1.56 12.50
1211期    GU Jian ̄Long et al.: Chemical Composition and Antimicrobial Activities of Essential Oils of Laggera pterodonta 􀆺   
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