全 文 ：昆 虫 学 报 Acta Entomologica Sinica，December 2012，55(12):1355 － 1361 ISSN 0454-6296
基金项目:国家自然科学基金项目(31000868)
作者简介:黄继光，男，1976 年生，湖北赤壁人，博士，副教授，研究方向为天然源农药与害虫治理，E-mail:hnnyzx@ scau． edu． cn
* 通讯作者 Corresponding author，E-mail:hnnyzx@ scau． edu． cn
收稿日期 Received:2012-09-07;接受日期 Accepted:2012-12-16
Insecticidal activities and active ingredients of Cacalia tangutica
against Musca domestica and Aedes albopictus
HUANG Ji-Guang* ，ZHAO Huan-Huan，MIAO Hui，XU Han-Hong
(Key Laboratory of Natural Pesticide and Chemical Biology，Ministry of Education，
South China Agricultural University，Guangzhou 510642，China)
Abstract:To study the insecticidal activities and active ingredients of Cacalia tangutica，the methanol
extracts of C． tangutica against Musca domestica and Aedes albopictus were bioassayed with feeding
method and dipping method． The active ingredients of C． tangutica were isolated and identified． Results
indicated that the methanol extracts from different parts of C． tangutica showed highly insecticidal
activities against adult M． domestica and the 4th instar larvae of A． albopictus． Nine compounds
(stigmasterol，friedelin，7-hydroxy-8-methoxycoumarin，umbelliferone，daphnetin，daphnetin-8-O-β-D-
glucopyranoside，quercetin，kaempferol and β-daucosterol)were isolated and identified from extracts of
leaves and flowers of C． tangutica． Among them，friedelin，quercetin and kaempferol were firstly isolated
from this plant． At 48 h after treatment，the corrected mortalities of adult M． domestica caused by
friedelin，quercetin and kaempferol at the dosage of 500 μg /g were 88． 33%，69． 90% and 77． 04%，
respectively． At 72 h after treatment，the corrected mortalities of the 4th instar larvae of A． albopictus
caused by friedelin，quercetin and kaempferol at the concentration of 50 μg /g were 88． 49%，72． 22%
and 71． 06%，respectively． The studies suggest that C． tangutica would be a promising control agent on
medical insects and deserves a further study．
Key words:Cacalia tangutica;Musca domestica;Aedes albopictus;insecticidal activities;chemicals
Plants in the sunflower family (Asteraceae)
contain biologically active substances that have
potential for crop protection against many insect
species． The genus Cacalia is comprised of about 80
species distributed in Asia and North America． Many
species in this genus have different ingredients，such
as C． yatabei Matsum ＆ Koidz (Hikichi et al．，
1978) ，C． auriculata DC (EI-Emary et al．，1980) ，
C． roborowskii (Maxim)Ling (Zhang et al．，1998) ，
C． delphiniifolia Sleb et Zucc (Shindo et al．，2004) ，
C． pilgeriana (Diels)Ling (Li et al．，2005) ，and C．
ainsliaeflora (Franch)Hand-Mazz (Mao et al．，2003，
2005)． Compounds previously isolated from Cacalia
include sterols，alkaloids，terpenes，etc． C． tangutica
(Franch)H． -M． is a 1 － 2 m tall herb irregularly
distributed in mountainous areas of central China． It is
traditionally used to treat various diseases such as
headache， rheumatism， cough， etc． However， the
bioactive principles have not been investigated．
Coumarins from C． tangutica have been reported (Yue
et al．，2005)． In 2009，in our preliminary study，we
reported the insecticidal activities of crude extracts
from this species and two constituents，friedelin and
stigmasterol， against Musca domestica and Aedes
albopictus (Skuse) (Huang et al．，2009)． As a
further understanding of the insecticidal activities of C．
tangutica，we systematically report herein insecticidal
activities and the constituents of C． tangutica that are
effective on M． domestica and A． albopictus (Skuse)．
1 MATERIALS AND METHODS
1． 1 Insects
M． domestica and A． albopictus，maintained for
more than 200 generations without any known
insecticide resistance，were obtained from laboratory
colonies in Guangdong Center for Disease Control
and Prevention， Guangzhou， China． Housefly
rearing methods were as per Zhou et al． (2006a)
and A． albopictus rearing methods followed Huang et
al． (2009)． The test insects were 2 － 4 day old
adult houseflies and 4th instar larvae of A．
albopictus． The insectary room was maintained at
25 ± 1℃，75% relative humidity and a 16L ∶ 8D
photoperiod．
1． 2 Plants materials
Whole plants of C． tangutica were collected in
full bloom from Enshi County，Hubei Province，in
July， 2009． These plants were identified by
Professor Li Bing-Tao of South China Agricultural
DOI:10.16380/j.kcxb.2012.12.005
1356 昆虫学报 Acta Entomologica Sinica 55 卷
University． Herbarium specimens were deposited in
the Key Laboratory of Natural Pesticide ＆ Chemical
Biology， Ministry of Education (South China
Agricultural University) ，China．
1． 3 Extraction and isolation of compounds
from C． tangutica
The materials (leaves and flowers)were air-
dried (4 kg)for up to 2 weeks at ambient laboratory
temperature and several hours in a 50 － 60℃
incubator prior to pulverization． A methanol extract
prepared by cold immersion extraction for 3 d was
concentrated in vacuo． Petroleum ether fraction
(400 g) ，chloroform fraction (50 g) ，ethyl acetate
fraction (35 g)and water fraction of extracts were
got by liquid-liquid partition method．
The petroleum ether fraction was subjected to
silica gel column chromatography (CC)and eluted
with petroleum ether-acetone (100 ∶ 0 － 0 ∶ 100) ，
petroleum ether-EtOAc (100 ∶ 0 － 0 ∶ 100) ，
respectively，and then separated by Sephadex LH-20
column with acetone，CHCl3-MeOH (2∶ 1)to obtain
compound 1 (68． 0 mg)and 2 (11． 2 mg)． The
chloroform fraction was chromatagraphed on a silica
gel column eluted with CHCl3-MeOH (100 ∶ 0 －
0∶ 100) ，petroleum ether-acetone(90∶ 10 － 30∶ 70) ，
petroleum ether-EtOAc (97 ∶ 3 － 20 ∶ 80)again and
again， respectively， sequentially separated by
Sephadex LH-20 column with CHCl3-MeOH (1 ∶ 1)
to yield compound 3 (187． 1 mg) ，4 (25． 5 mg) ，
and 5 (18． 8 mg)． The ethyl acetate fraction was
eluted with increasing polarity CHCl3-MeOH (98∶ 2 －
0∶ 100) ，and then eluted with petroleum ether-
EtOAc (95 ∶ 5 － 0 ∶ 100) ，CHCl3-EtOAc (97 ∶ 3 －
20∶ 80) ，CHCl3-acetone (98 ∶ 2 － 20 ∶ 80) ，
respectively，by silica gel CC repeatedly，followed
by Sephadex LH-20 eluted with MeOH and
crystallization to afford compound 6 (52． 3 mg) ，7
(8． 3 mg) ，8 (6． 7 mg) ，and 9 (49． 8 mg)．
The compounds were identified according to
their spectrum of NMR，MS．
1． 4 Bioassay of extracts and compounds against
M． domestica
Housefly adults (males and females)at 2 d
after emergence were used． The standard assay was
performed by placing granulated cane sugar in a 20
mL vial followed by the test extract or fraction
dissolved in acetone． The sugar which was dissolved
in acetone only was used as the control． When the
acetone was completely evaporated，leaving most of
the dissolved compounds as a coating on the sugar，
the adult houseflies were introduced and the vial was
closed with a screw cap． Mortality in these ingestion
assays was recorded regularly． Each treatment was
replicated 3 times，with 10 houseflies per replicate
(Huang et al．，2009)．
1． 5 Bioassay of extracts and compounds against
A． albopictus
The extracts and compounds were individually
dissolved and serially diluted with acetone． Each
resultant solution (2 mL)was added to a beaker
containing 98 mL of distilled water to give a
concentration of 0． 1% (m/v) ，and then 20 the 4th
instar larvae were transferred into the beaker． The
solution comprised of 98 mL distilled water and 2 mL
acetone was used as the control． Mortality in these
assays was recorded regularly． Each treatment was
replicated 5 times (Huang et al．，2009)．
1． 6 Data analysis
Control mortality was corrected by using
Abbott’s formula． The regression line was
determined for the percentage mortality data
corrected using Abbott’s formula and the LC50 value
was calculated from the equation of this line．
Duncan’s multiple range test was used at P = 0． 05
to compare the differences among means with
converted data．
2 RESULTS
2． 1 Toxicities of the extracts from different
parts of C． tangutica against adult Musca
domestica and the 4th instar larvae of
A． albopictus
The extracts from different parts of C． tangutica
were toxic to adult M． domestica and the 4th instar
larvae of A． albopictus． Particularly，the extracts
from leaves and flowers showed significant activities
against these two species (Table 1)．
Petroleum ether fraction， chloroform fraction
and ethyl acetate fraction of extracts from leaves and
flowers were toxic to adult M． domestica，with the
mortalities varying from 66． 12% to 88． 14% ． The
most toxic one was the petroleum ether fraction of
extracts from C． tangutica leaves，which caused a
mortality of 88． 14% at 48 h after treatment．
Chloroform fraction and ethyl acetate fraction of
extracts from leaves and flowers were toxic to the 4th
instar larvae of A． albopictus，with the mortalities
varying from 66． 29% to 78． 65% ． Chloroform
fraction of leaf extracts and ethyl acetate fraction of
flower extracts were equitoxic to the 4th instar larvae
of A． albopictus and the mortalities were 78． 65%
and 78． 48%，respectively．
Water fraction of extracts from leaves and
flowers were the least toxic to both species (Table
2)．
12 期 HUANG Ji-Guang et al．:Insecticidal activities and active ingredients of Cacalia tangutica 1357
Table 1 Toxicity of the extracts from different parts of Cacalia tangutica against adult Musca domestica and
the 4th instar larvae of Aedes albopictus
Plant parts Extraction rates
(%)
Corrected mortality (%)
M． domestica A． albopictus
24 h 48 h 24 h 48 h
Roots 10． 22 79． 66 ± 5． 08 a 91． 38 ± 2． 99 b 72． 27 ± 4． 37 b 88． 03 ± 5． 34 b
Stems 9． 38 55． 93 ± 7． 77 b 82． 76 ± 2． 99 c 55． 46 ± 3． 85 c 78． 63 ± 1． 48 c
Leaves 19． 89 83． 05 ± 2． 94 a 100． 00 ± 0． 00 a 80． 67 ± 1． 46 a 97． 44 ± 2． 56 a
Flowers 17． 59 81． 36 ± 2． 94 a 98． 28 ± 2． 99 a 84． 03 ± 3． 85 a 95． 73 ± 1． 48 a
Control － 1． 67 ± 0． 91 c 3． 33 ± 0． 87 d 0． 83 ± 0． 36 d 2． 50 ± 1． 05 d
The data of control were mortalities． The tested dosage against adult M． domestica and the tested concentration against the 4th instar larvae of A． albopictus
were 1% and 0． 1% (m/v) ，respectively． The data (mean ± SE)within a column followed by different small letters were significantly different at P =
0． 05 based on Duncan’s multiple range test (DMRT)． The same for the following tables．
Table 2 Toxicity of different partition fractions of extracts from Cacalia tangutica leaves and
flowers against adult Musca domestica and the 4th instar larvae of Aedes albopictus (48 h)
Partition fractions Plant parts
Corrected mortality (%)
M． domestica A． albopictus
Petroleum ether fraction
Leaves 88． 14 ± 2． 59 a 33． 71 ± 1． 72 b
Flowers 66． 12 ± 2． 14 a 29． 61 ± 2． 03 b
Chloroform fraction
Leaves 85． 05 ± 1． 85 a 78． 65 ± 3． 61 a
Flowers 79． 38 ± 4． 55 a 73． 62 ± 3． 34 a
Ethyl acetate fraction
Leaves 78． 85 ± 3． 27 a 66． 29 ± 1． 12 a
Flowers 71． 19 ± 2． 11 a 78． 48 ± 1． 67 a
Water fraction
Leaves 43． 18 ± 2． 96 b 37． 08 ± 1． 72 b
Flowers 29． 53 ± 2． 63 b 30． 56 ± 1． 95 b
Control
Leaves 1． 67 ± 0． 96 c 1． 11 ± 0． 64 c
Flowers 3． 03 ± 0． 87 c 0． 00 ± 0． 00 c
For M． domestica，the sugar which was dissolved in acetone was used as the control;for A． albopictus，the solution comprised of 98 mL
distilled water and 2 mL acetone was used as the control． The same for Tables 4，5 and 6． The tested dosage against adult M． domestica
and the tested concentration against the 4th instar larvae of A． albopictus were 1% and 0． 1% (m/v) ，respectively．
Based on the LC50 values 48 h after treatment，the
toxicity of leaf extracts to adult M． domestica from high
to low was chloroform fraction，petroleum ether fraction
and ethyl acetate fraction，with the LC50 values ranging
from 342． 72 to 398． 10 μg /g sugar． While the toxicity
of flower extracts to adult M． domestica from high to
low was chloroform fraction，ethyl acetate fraction and
petroleum ether fraction，with the LC50 values ranging
from 322． 06 to 642． 73 μg /g sugar (Table 3)．
To A． albopictus larvae， the LC50 values of
chloroform fraction and ethyl acetate fraction were less
than 50 μg /mL． The ethyl acetate fraction of flower
extract was the most toxic，with the LC50 value of
24． 13 μg /mL (Table 4)．
Table 3 LC50 values of different partition fractions of extracts from Cacalia tangutica leaves
and flowers against adult Musca domestica (48 h)
Extracts Plant parts Toxicity regression equation Coefficient correlation LC50(μg /g sugar) 95% Confidence interval
Petroleum ether fraction
Leaves y = 0． 1051 + 1． 9239x 0． 9945 350． 09 279． 45 － 438． 57
Flowers y = 1． 0634 + 1． 4019x 0． 9814 642． 73 429． 45 － 961． 94
Chloroform fraction
Leaves y = 0． 0250 + 1． 9626x 0． 9958 342． 72 275． 39 － 426． 50
Flowers y = 1． 3549 + 1． 4534x 0． 9850 322． 06 245． 37 － 422． 72
Ethyl acetate fraction
Leaves y = 0． 6880 + 1． 6585x 0． 9910 398． 10 304． 85 － 519． 88
Flowers y = 1． 8672 + 1． 1932x 0． 9800 422． 12 294． 71 － 604． 61
1358 昆虫学报 Acta Entomologica Sinica 55 卷
Table 4 LC50 values of chloroform fraction and ethyl acetate fraction of extracts from Cacalia tangutica leaves
and flowers against the 4th instar larvae of Aedes albopictus (48 h)
Extracts Plant parts Toxicity regression equation Coefficient correlation LC50(μg /mL) 95% Confidence interval
Chloroform fraction
Leaves y = 2． 5488 + 1． 5257x 0． 9893 40． 42 33． 50 － 48． 78
Flowers y = 3． 1508 + 1． 1756x 0． 9878 37． 41 29． 37 － 47． 65
Ethyl acetate fraction
Leaves y = 2． 9982 + 1． 2209x 0． 9885 43． 62 34． 61 － 54． 96
Flowers y = 3． 3828 + 1． 1697x 0． 9913 24． 13 19． 01 － 30． 62
2． 2 Structure identification of the isolated
chemicals
Stigmasterol (1) :white needles (petroleum
ether-EtOAc) ，m． p．: 167 － 169℃ ． 1H-NMR
(CDCl3，500 MHz)δ:3． 53 (1H，m，H-3) ，5． 36
(1H，d，J = 4． 65 Hz，H-6) ，0． 71 (3H，s，H-
18) ，0． 93 (3H，s，H-19) ，1． 02 (3H，s，H-21) ，
5． 16 (1H，dd，J = 15． 15，8． 65 Hz，H-22) ，5． 02
(1H，dd，J = 15． 1，8． 75 Hz，H-23) ，0． 83 (3H，
s，H-26) ，0． 81 (3H，s，H-27) ，0． 85 (3H，d，
J = 1． 4 Hz，H-29)． 13C-NMR (CDCl3，125 MHz)
δ:37． 3 (C-1) ，29． 3 (C-2) ，71． 9 (C-3) ，39． 9
(C-4) ，140． 8 (C-5) ，121． 7 (C-6) ，32． 0 (C-7) ，
31． 9 (C-8) ，50． 2 (C-9) ，36． 6 (C-10) ，21． 1
(C-11) ，39． 8 (C-12) ，42． 3 (C-13) ，56． 0 (C-
14) ，24． 4 (C-15) ，28． 9 (C-16) ，56． 9 (C-17) ，
12． 0 (C-18) ，19． 4 (C-19) ，40． 5 (C-20) ，21． 2
(C-21) ，138． 3 (C-22) ，129． 4 (C-23) ，51． 3 (C-
24) ，31． 7 (C-25) ，19． 0 (C-26) ，21． 0 (C-27) ，
25． 4 (C-28) ，12． 2 (C-29) (Zhao et al．，2007)．
Friedelin (2) :colorless needles (CHCl3-
MeOH) ，m． p．:265 － 267℃;EI-MS m/z:426．
1H-NMR (CDCl3，500 MHz)δ:0． 88 (3H，s，H-
23) ，0． 73 (3H，s，H-24) ，0． 87 (3H，s，H-25) ，
1． 01 (3H，s，H-26) ，1． 05 (3H，s，H-27) ，1． 18
(3H，s，H-28) ，0． 95 (3H，s，H-29) ，1． 00 (3H，
s，H-30)． 13C-NMR (CDCl3，125 MHz)δ:22． 3
(C-1) ，41． 5 (C-2) ，213． 0 (C-3) ，58． 3 (C-4) ，
42． 1 (C-5) ，41． 4 (C-6) ，18． 3 (C-7) ，53． 2 (C-
8) ，37． 5 (C-9) ，59． 6 (C-10) ，35． 7 (C-11) ，
30． 5 (C-12) ，39． 8 (C-13) ，38． 4 (C-14) ，32． 5
(C-15) ，36． 1 (C-16) ，30． 0 (C-17) ，42． 9 (C-
18) ，35． 4 (C-19) ，28． 2 (C-20) ，32． 9 (C-21) ，
39． 3 (C-22) ，6． 8 (C-23) ，14． 7 (C-24) ，18． 0
(C-25) ，20． 3 (C-26) ，18． 7 (C-27) ，32． 1 (C-
28) ，35． 0 (C-29) ，31． 8 (C-30) (Fu et al．，
2004)．
7-Hydroxy-8-methoxycoumarin(3) :white flaky
crystals (CHCl3-MeOH) ，obvious fluorescence in
UV，m． p．:154 － 156℃ ． 1H-NMR (CDCl3，500
MHz)δ:6． 25 (1H，d，J = 11． 4 Hz，H-3) ，7． 64
(1H，d，J = 11． 4 Hz，H-4) ，7． 12 (1H，d，J =
10． 2 Hz，H-5) ，6． 91 (1H，d，J = 10． 2 Hz，H-
6) ，4． 11 (3H，s，8-OCH3) (Zhou，2004)．
Umbelliferone (4 ) : colorless needles
(petroleum ether-acetone) ，blue fluorescence in
UV． 1H-NMR (CD3COCD3，400 MHz)δ:6． 16
(1H，d，J = 9． 6 Hz，H-3) ，7． 85 (1H，d，J = 9． 6
Hz，H-4) ，7． 50 (1H，d，J = 8． 4 Hz，H-5) ，6． 83
(1H，dd，J = 5． 6，2． 4 Hz，H-6) ，6． 74 (1H，d，
J = 2． 0 Hz，H-8)． 13C-NMR (CD3COCD3，100
MHz)δ:161． 9 (C-2) ，103． 3 (C-3) ，144． 7 (C-
4) ，130． 4 (C-5) ，113． 7 (C-6) ，156． 9 (C-7) ，
112． 9 (C-8) ，161． 0 (C-9) ，117． 9 (C-10)
(Wang et al．，2002)．
Daphnetin (5) :colorless needles (petroleum
ether-acetone) ，blue fluorescence in UV． 1H-NMR
(CD3COCD3，400 MHz)δ:6． 14 (1H，d，J = 9． 6
Hz，H-3) ，7． 83 (1H，d，J = 9． 6 Hz，H-4) ，7． 04
(1H，d，J = 8． 4 Hz，H-5) ，6． 85 (1H，d，J = 8． 4
Hz，H-6)． 13C-NMR (CD3COCD3，100 MHz)δ:
160． 6 (C-2) ，112． 7 (C-3) ，145． 3 (C-4) ，113． 1
(C-5) ，132． 7 (C-6) ，113． 4 (C-7) ，149． 8 (C-
8) ，144． 5 (C-9) ，120． 0 (C-10) (Yu and Yang，
1999)．
Daphnetin-8-O-β-D-glucopyranoside (6 ) :
colorless needles (CHCl3-MeOH) ，soluble in
C5H5N and DMSO．
1H-NMR (CD3SOCD3，600
MHz)δ:6． 23 (1H，d，J = 9． 6 Hz，H-3) ，7． 93
(1H，d，J = 9． 6 Hz，H-4) ，7． 31 (1H，d，J = 9
Hz，H-5) ，6． 87 (1H，d，J = 8． 4 Hz，H-6) ，4． 98
(1H，d，J = 7． 8 Hz，H-1) ，3． 22 － 3． 75 (6H，
m，H-2，3，4，5，6)． 13C-NMR (C5D5N，100
MHz)δ:160． 9 (C-2) ，113． 0 (C-3) ，144． 5 (C-
4) ，124． 9 (C-5) ，112． 4 (C-6) ，155． 2 (C-7) ，
133． 3 (C-8) ，149． 1 (C-9) ，114． 3 (C-10) ，
107． 1 (C-1) ，75． 5 (C-2) ，79． 2 (C-3) ，71． 3
(C-4) ，78． 2 (C-5) ，62． 6 (C-6) (Ullah et al．，
1999)．
Quercetin (7) :pale yellow powder (MeOH) ，
m． p．:310 － 312℃ ． 1H-NMR (CD3OD，400 MHz)
δ:6． 17 (1H，d，J = 2． 5 Hz，H-6) ，6． 38 (1H，
d，J = 2． 5 Hz，H-8) ，7． 73(1H，d，J = 2． 5 Hz，
H-2) ，6． 88 (1H，d，J = 8． 5 Hz，H-5) ，7． 63
(1H，dd，J = 8． 5，2． 5 Hz，H-6)． 13C-NMR
(CD3OD，100 MHz)δ:148． 0 (C-2) ，137． 2 (C-
3) ，177． 3 (C-4) ，158． 2 (C-5) ，99． 2 (C-6) ，
165． 6 (C-7) ，94． 4 (C-8) ，162． 5 (C-9) ，104． 5
12 期 HUANG Ji-Guang et al．:Insecticidal activities and active ingredients of Cacalia tangutica 1359
(C-10) ，124． 1 (C-1) ，116． 0 (C-2) ，146． 2 (C-
3) ，148． 8 (C-4) ，116． 2 (C-5) ，121． 7 (C-6)
(Fossen et al．，1998)．
Kaempferol (8) :yellow needles (MeOH) ，m．
p．:281 － 283℃ ． 1H-NMR (CD3OCD3，400 MHz)
δ:6． 26 (1H，d，J = 2． 0 Hz，H-6) ，6． 53 (1H，
d，J = 2． 0 Hz，H-8) ，8． 15 (2H，dd，J = 8． 0，2． 0
Hz H-2，6) ，7． 01 (2H，dd，J = 8． 0，2． 0 Hz，
H-3，5)． 13C-NMR (CD3OCD3，100 MHz)δ:
148． 1 (C-2) ，137． 2 (C-3) ，176． 6 (C-4) ，162． 3
(C-5) ，99． 1 (C-6) ，165． 0 (C-7) ，94． 5(C-8) ，
157． 8 (C-9) ，104． 2 (C-10) ，123． 6 (C-1) ，
130． 4 (C-2，6) ，160． 2 (C-4) ，116． 3 (C-3，
5) (Liu and Wang，2007)．
β-daucosterol (9) :white powder， ESI-MS
m/z:575 ［M + H］ + ． 1H-NMR (C5D5N，400
MHz)δ:2． 71 (1H，d，J = 3． 6 Hz，H-3) ，5． 34
(1H，s，H-6) ，0． 64 (3H，s，H-18) ，0． 98 (3H，
s，H-19) ，0． 90 (3H，s，H-21) ，0． 84 (3H，s，H-
26) ，0． 86 (3H，s，H-27) ，0． 88 (3H，s，H-29) ，
5． 06 (1H，d，J = 12 Hz，H-1) ，4． 43 (1H，t，
J = 13． 2 Hz，H-2) ，4． 08 (1H，t，J = 11． 4 Hz，
H-3) ，3． 99 (1H，m，H-4)，4． 58 (1H，d，J =16． 8
Hz，H-5) ，4． 30 (2H，t，J = 7． 2 Hz，H-6)． 13C-
NMR (C5D5N，100 MHz)δ:37． 5 (C-1) ，29． 5
(C-2) ，78． 1 (C-3) ，40． 0 (C-4) ，140． 9 (C-5) ，
122． 0 (C-6) ，32． 2(C-7) ，32． 1 (C-8) ，50． 4 (C-
9) ，37． 0 (C-10) ，21． 3 (C-11) ，39． 4 (C-12) ，
42． 5(C-13) ，56． 9 (C-14) ，24． 5(C-15) ，28． 6
(C-16) ，56． 1 (C-17) ，12． 0 (C-18) ，19． 2 (C-
19) ，36． 4 (C-20) ，19． 1 (C-21) ，34． 2 (C-22) ，
26． 4 (C-23) ，46． 1 (C-24) ，29． 5 (C-25) ，19． 5
(C-26) ，20． 0 (C-27) ，23． 4 (C-28) ，12． 2(C-
29) ，102． 6 (C-1) ，75． 4 (C-2) ，78． 1 (C-3) ，
71． 7(C-4) ，78． 5 (C-5) ，62． 3 (C-6) (Li et
al．，2007)．
2． 3 Insecticidal activities of the isolated
chemicals against adult M． domestica and the 4th
instar larvae of A． albopictus
At the dosage of 500 μg /g， friedelin and
rotenone (the positive control)were equitoxic to
adult M． domestica 24 h after treatment and the
corrected mortalities were 55． 63% and 69． 47%，
respectively． Friedelin，rotenone，kaempferol and
quercetin were equitoxic to adult M． domestica 48 h
after the treatment and the corrected mortalities were
88． 30%， 87． 96%， 77． 04% and 69． 90%，
respectively． Daphnetin-8-O-β-D-glucopyranoside，
daphnetin， 7-hydroxy-8-methoxycoumarin and
umbelliferone exhibited toxicities to some extent
(Table 5)．
All the tested chemicals except umbelliferone
were equitoxic to the 4th instar larvae of A．
albopictus at 48 h after treatment at the concentration
of 50 μg /mL． At 72 h after treatment，rotenone，
friedelin，quercetin and kaempferol were equitoxic
and the corrected mortalities of the 4th instar larvae
of A． albopictus they caused were 88． 33%，88． 49%，
72． 22% and 71． 06%，respectively (Table 6)．
3 DISCUSSION
Many plants in Asteraceae showed bioactivities
(Zhou et al．，2006b，2010)． We found that C．
tangutica had obvious insecticidal activities against
M． domestica and A． albopictus，two insect species
important in public health． However，the outdoor
activities are not clear and it needs further
researches．
Table 5 Toxicity of seven compounds isolated from Cacalia tangutica against adult Musca domestica
Compounds
Corrected mortality (%)
24 h 48 h
Friedelin 55． 63 ± 1． 99 ab 88． 30 ± 1． 03 a
7-Hydroxy-8-methoxycoumarin 39． 12 ± 2． 38 bc 57． 09 ± 3． 23 d
Umbelliferone 36． 67 ± 4． 19 cd 50． 85 ± 2． 59 d
Daphnetin 35． 00 ± 1． 67 cd 59． 32 ± 1． 69 cd
Daphnetin-8-O-β-D-glucopyranoside 34． 60 ± 4． 56 cd 68． 36 ± 1． 82 bcd
Quercetin 52． 46 ± 2． 50 bc 69． 90 ± 1． 90 abcd
Kaempferol 51． 97 ± 4． 06 bc 77． 04 ± 1． 85 abc
Rotenone 69． 47 ± 3． 35 a 87． 96 ± 0． 93 ab
Control 0． 00 ± 0． 00 e 1． 67 ± 0． 96 e
The tested dosage was 500 μg /g． The other isolated compounds were not listed for insufficient quantity for bioassay or no
activities;the same for Table 6．
1360 昆虫学报 Acta Entomologica Sinica 55 卷
Table 6 Toxicity of seven compounds isolated from Cacalia angutica against the 4th instar larvae of Aedes albopictus
Compounds
Corrected mortality (%)
48 h 72 h
Friedelin 59． 05 ± 1． 76 ab 88． 49 ± 1． 01 a
7-Hydroxy-8-methoxycoumarin 44． 37 ± 1． 99 ab 55． 79 ± 2． 69 b
Umbelliferone 41． 67 ± 3． 47 b 51． 67 ± 4． 19 b
Daphnetin 56． 27 ± 2． 55 ab 65． 00 ± 2． 89 b
Quercetin 63． 97 ± 1． 77 a 72． 22 ± 2． 31 ab
Kaempferol 60． 00 ± 4． 41 ab 71． 06 ± 2． 63 ab
Rotenone 56． 67 ± 1． 92 ab 88． 33 ± 0． 96 a
Control 0． 00 ± 0． 00 d 0． 00 ± 0． 00 d
The tested concentration was 50 μg /mL．
Most work on C． tangutica focused on the
chemical constituents． Main constituents of this plant
were terpenes． From the root of C． tangutica，Liu
and Tian (2004) got one novel eremophilane
sesquiterpene and eight known chemicals including
petasine，α-amyrin，ursolic acid，hydroxytremetone，
daphnetol， hydrangetin， umbelliferone and β-
sitosterol． From the flowers of C． tangutica，Liu and
Shi (2005)got two novel epimeric sesquiterpenes，
two novel eremophilane sesquiterpenes and nine
known triterpenes． Liu et al． (2007)also found 7
sesquiterpenes from the upper part of C． tangutica．
Other researches also revealed that there were sterols
and coumarins in this plant (Liu et al．，2008)．
Little work has been done on the bioactivities of
C． tangutica． In 2009，we reported the insecticidal
and cytotoxic activities of extracts of C． tangutica
and its two active ingredients against M． domestica
and A． albopictus (Huang et al．，2009)． Methanol
extracts from different tissues of C． tangutica were
toxic to adult M． domestica and the 4th instar larvae
of A． albopictus，and those from leaves and flowers
showed higher insecticidal activities． In this further
study，we got nine chemicals including stigmasterol，
friedelin，7-hydroxy-8-methoxy-coumarin，umbelliferone，
daphnetin， daphnetin-8-O-β-D-glucopyranoside，
quercetin，kaempferol and β-daucosterol from this
plant． Friedelin， quercetin and kaempferol were
isolated from the plant for the first time and they
possessed obvious toxicities to M． domestica and A．
albopictus，which was not different from that of
rotenone． Therefore， the application of friedelin，
quercetin and kaempferol on the control of medical
insects is promising and deserves a further study．
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羽裂蟹甲草对家蝇和白纹伊蚊的杀虫活性和活性成分
黄继光* ，赵欢欢，苗 辉，徐汉虹
(华南农业大学天然农药与化学生物学教育部重点实验室，广州 510642)
摘要:为探明羽裂蟹甲草 Cacalia tangutica的杀虫活性及其活性成分，通过拌糖饲喂法和浸渍法测定了羽裂蟹甲
草甲醇提取物对家蝇 Musca domestica成虫和白纹伊蚊 Aedes albopictus 4 龄幼虫的毒杀活性，并采用色谱分离技术
和现代波谱技术对羽裂蟹甲草中的化学成分进行了分离鉴定。结果表明:该植物不同部位甲醇提取物对家蝇成虫
和白纹伊蚊 4 龄幼虫均具有较高的生物活性。从该植物叶和花甲醇提取物中分离鉴定了豆甾醇、无羁萜、7-羟基-
8-甲氧基香豆素、7-羟基香豆素、7，8-二羟基香豆素、瑞香素-8-O-β-D-葡萄糖苷、槲皮素、山奈酚和 β-胡萝卜苷 9
个化合物。无羁萜、槲皮素和山奈酚为首次从该植物中分离得到，500 μg /g拌糖处理 48 h后，其对家蝇成虫的校
正死亡率分别为 88． 30%，69． 90%和 77． 04%;50 μg /mL药液处理 72 h后，其对白纹伊蚊 4 龄幼虫的校正死亡率
分别为 88． 49%，72． 22%和 71． 06%;均与鱼藤酮差异不显著(P ＜ 0． 05) ，表现出良好的杀虫活性。本研究说明羽
裂蟹甲草对家蝇和白纹伊蚊具有明显的毒杀活性，是一种潜在的卫生害虫控制剂。
关键词:羽裂蟹甲草;家蝇;白纹伊蚊;杀虫活性;化学成分
中图分类号:Q965． 9 文献标志码:A 文章编号:0454-6296(2012)12-1355-07
(责任编辑:赵利辉)