全 文 ：昆 虫 学 报 Acta Entomologica Sinica，December 2011，54(12):1368 － 1376 ISSN 0454-6296
基金项目:国家自然科学基金项目(31071715) ;教育部博士点新教师基金项目(20094320120002) ;湖南省教育厅青年基金项目(09B048)
作者简介:李有志，男，1970 年生，湖南常德人，博士，副教授，主要从事植物源杀虫成分研究，E-mail:liyouzhi2008@ sina． com
* 通讯作者 Corresponding author，E-mail:hhxu@ scau． edu． cn
收稿日期 Received:2011-07-04;接受日期 Accepted:2011-11-17
Isolation and identification of insecticidal compounds
from Tephrosia purpurea (Fabaceae)bark and
their insecticidal activity
LI You-Zhi1，2，LI Guan-Hua2，WEI Xiao-Yi4，
LIU Zhong-Hua1，XU Han-Hong3，*
(1． National Research Center of Engineering ＆ Technology for Utilization of Botanical Functional Ingredients，
Hunan Agricultural University，Changsha 410128，China;2． Hunan Provincial Key Laboratory for Biology and
Control of Plant Diseases and Insect Pests，College of Bio-Safety Science and Technology，Hunan Agricultural University，
Changsha 410128，China;3． Key Laboratory of Natural Pesticide and Chemical Biology，College of Natural Resources
and Environment，South China Agricultural University，Guangzhou 510642，China;4． South China Botanical Garden，
Chinese Academy of Sciences，Guangzhou 510650，China)
Abstract:In order to determine insecticidal compounds from the methanol extracts of Tephrosia purpurea
bark，the active compounds were isolated by activity-guided fractionation with column chromatography
and identified based on NMR (nuclear magnetic resonance)and MS (mass spectrometry)data． Slide-
dip method was performed to determine the insecticidal activities of each compound against Myzus persicae
adults，and topical application was conducted to determine contact toxicity of each compound against the
3rd instar larvae of Pluttella xylostella． Ten known compounds were isolated and identified，i． e．，12a-
hydroxyrotenone，4-hydroxyemoroidocarpan，pachyrrhizine，rotenone，6-methoxycoumarin，(-)-edunol，
obovatin， pongachin， 12-acetyelliptinol and 2-hydroxyrotenone． All these compounds exhibited
insecticidal activity against the 4th instar larvae of Aedes albopictus with the LC50 value being 12． 5，22． 1，
25． 0，34． 1，43． 4，58． 4，121． 9，191． 0，219． 8 and 250． 0 mg /L，respectively at 24 h after treatment．
Moreover，three compounds (4-hydroxyemoroidocarpan，rotenone and 12a-hydroxyrotenone)exhibited
insecticidal activity against M． persicae adults and the 3rd instar larvae of P． xylostella with their
corresponding LC50 values being 49． 9，1． 9 and 0． 9 mg /L against M． persicae adults，and with the LD50
values being 49． 8，197． 1 and 40． 9 μg / individual against P． xylostella larvae，respectively． Eight
known compounds， i． e．， 4-hydroxyemoroidocarpan， 2-hydroxyrotenone， 6-methoxycoumarin，
pachyrrhizine，(-)-edunol，12-acetyelliptinol，pongachin and obovatin，were isolated from T． purpurea
bark for the first time． The elucidation of the structure of these phytochemicals and their insecticidal
activity is important not only for understanding the insect-plant relationships，but also for assessing the
potential of this plant as botanical insecticide to be explored and utilized．
Key words:Tephrosia purpurea; insecticidal compounds; insecticidal activities;Aedes albopictus;
Pluttella xylostella;Myzus persicae
1 INTRODUCTION
At present， the control of insect pests is
primarily dependent on chemical insecticides such as
organophosphorus compounds and the synthetic
pyrethroids． However，the long-term use of synthetic
insecticides has caused environmental contamination，
toxicity to non-target organisms and resurgence of
target pests (Isman，2000)． These problems promote
researchers to develop new environmentally friendly
pesticides．
As is well known，plant secondary metabolites
play an important role in protection of the plants from
being damaged by pests，germs and adverse climate
(Chen，2004)． In fact，some phytochemicals have
been used to control pests for centuries (Huang et
al．，2010)． Even today，some farmers still use the
dried stems of Nicotiana tabacum and dried flowers
of Rhododendron molle to control pests in China
(Huang et al．，2010)． Botanicals with insecticidal
activities are the potential sources to be utilized as
insecticides (Xu， 2001 )． Therefore， most
researches on pesticides focused on seeking and
DOI:10.16380/j.kcxb.2011.12.004
12 期 LI You-Zhi et al．:Isolation and identification of insecticidal compounds from Tephrosia purpurea 1369
exploring new types of botanical pesticides，which
are biodegradable into nontoxic products and suitable
for the control of insect pests in the integrated
management programs (Ben et al．，2000;Nathan et
al．，2007;Pavela and Herda，2007)．
Tephrosia purpurea (Fabaceae) is a tropical
and subtropical species． Previous studies revealed
that some flavonoids occurred in this plant and
focused on medical values of these compounds and
the extracts from this plant (Sinha et al．，1982;Rao
and Raju，1984;Khan et al．，2001) ，while little
was reported on the insecticidal activity in the
extracts from this plant． In fact，some published
documents reported that its methanol extracts
possessed insecticidal activities against various
species of insect pests (Li et al．，2007，2011) ，
suggesting that exploration and utilization of the plant
as botanical insecticides deserve to be evaluated． It
was also reported that some flavonoids in this plant
are prenylated flavones(Sinha et al．，1982;Rao and
Raju，1984) ，which undergo further substitution and
cyclization leading to complex molecules (Sinha et
al．，1982)． According to these results， more
insecticidal compounds with complex chemical
structure presumably occur in this plant． So the aim
of this study was to isolate insecticidal compounds
from T． purpurea bark and to determine their
insecticidal activity，which may be useful for further
exploration and utilization of the plant as botanical
insecticides．
2 MATERIALS AND METHODS
2． 1 Plant materials
The stem bark of T． purpurea was collected in
South China Agricultural University， Guangdong
province， southern China， in April 2006， and
identified by Professor Zhong Ye-Cong from Guangxi
Academy of Forestry． An authenticated voucher
specimen (No． 200607)of this plant was deposited
at College of Bio-Safety Science and Technology，
Hunan Agricultural University．
2． 2 Insects
Aedes albopictus larvae were reared successively
in the laboratory with ten percentage yeast
suspension as the food source following the method of
Huang et al． (2010)． Pluttella xylostella and Myzus
persicae colonies， which were collected from
container-grown cauliflowers in glasshouses，were
reared respectively on cauliflowers in a thermostatic
chamber，Hunan Agricultural University． All the
tested insects were maintained at 25 ± 1℃，75% －
85% RH with a 12-hour photoperiod．
2． 3 Bioassays
Activity-guided method was performed to
determine the insecticidal activity in the plant
extracts or fractions (Li and Xu，2007;Huang et
al．，2010)． A volume of 24． 5 mL distilled water
was mixed into 500 μL dimethyl sulfoxide (DMSO)
solution containing extracts or fraction in a cup，with
gentle shaking to ensure a homogeneous test
solution，and then 30 4th instar mosquito larvae were
transferred to the cup． The control was exposed to
the mixture of 24． 5 mL distilled water and 500 μL
DMSO． The concentration of extracts or fractions was
500 mg /L． Mortality was recorded at 24 h after
treatment． For each treatment three replicates were
carried out．
Each compound was dissolved with acetone，
and then diluted into a series of five different
concentrations． Insecticidal activity in each
compound against mosquito larvae was determined by
the above-mentioned activity-guided method． Topical
application (Huang， 2000) was conducted to
determine the contact toxicity of the compounds
against the 3rd instar larvae of P． xylostella，and
every time 0． 1 μL the mixture of compound and
acetone was dipped on the pronotum of each larva．
Slide-dip method (Huang，2000)was performed to
determine the insecticidal activity of each compound
against M． persicae adults． Three replicates with a
total of 90 insects were carried out simultaneously for
each dilution． Controls were exposed to the solvent
acetone alone． Mortality rate was recorded at 24 h
after treatment．
2． 4 Extraction and isolation of compounds
from T． purpurea bark
The air-dried and powered bark of T． purpurea
(2． 3 kg)was placed in a stopped conical flask and
continuously extracted with methanol (50 L)for 3 d
at room constant temperature (28 － 30℃) with
occasional stirring， and then filtered． After the
extraction was done successively three times，
evaporation of the combined filtrate under vacuum at
50℃ yielded a methanolic extract(257． 6 g，11． 2%
from the dried bark)．
The methanolic extract (20． 0 g per time)was
suspended in a mixture (2 L)of water and methanol
(4∶ 1，v /v)and repeatedly extracted in a 15 L glass-
bottle with 10 L solvent of increasing polarity starting
with petroleum ether (PE) ，then trichloromethane
(CHCl3) ，and finally ethyl acetate (EtOAc)． Thus
257． 6 g methanolic extract yielded petroleum ether-
(22． 3 g) ，CHCl3-(95． 0 g) ，EtOAc-(20． 6 g) ，
and H2O-soluble (119． 2 g)residues．
These residues were subjected to the
1370 昆虫学报 Acta Entomologica Sinica 54 卷
insecticidal assays against the 4th instar larvae of A．
albopictus and the CHCl3-soluble residue showed the
most potent activity． This residue (95． 0 g)was
subjected to silica gel column chromatography
(100 － 200 mesh)and eluted first with petroleum
ether and then with a gradient of PE-EtOAc (0 －
100%)and finally MeOH，to give 147 fractions of
1 000 mL each． Verified by thin layer
chromatography (TLC) ，fractions 5 － 16，45 － 56，
and 93 － 123 were found to be active in the
insecticidal activity evaluation， and the other
inactive fractions were discarded．
Fractions 5 － 16 were applied to TLC，and
eluted with PE-EtOAc (90 ∶ 10， v /v) to give
compound A (56． 3 mg)． Fractions 45 － 46 were
applied to a silica gel column (200 － 300 mesh)
again， and eluted with petroleum ether-EtOAc
(15∶ 85， v /v) to give 97 subfractions． These
subfractions were combined on the basis of the TLC
results，and then the residues were used for the
insecticidal assays against A． albopictus larvae．
Subfractions 26 － 37，which exhibited insecticidal
activity，were further subjected to a silica gel
(200 － 300 mesh)column，eluted with PE-EtOAc
(90∶ 10，v /v)to give compound H(32． 7 mg)and
compound J (48． 7 mg)．
Fractions 93 － 123 were applied to a silica gel
column (200 － 300 mesh)again，and eluted with
PE-EtOAc (15∶ 85，v /v)to give 116 subfractions．
These subfractions were combined on the basis of the
TLC results，and then the residues were used for the
insecticidal assays against A． albopictus larvae．
Subfractions 10 － 19 and subfractions 21 － 39
exhibited insecticidal activity． Subfractions 10 － 19
were further subjected to a silica gel (200 － 300
mesh)column，and eluted with PE-EtOAc (10∶ 90，
v /v) to give compounds C (178． 8 mg) and D
(10． 7 mg)． The rest subfractions 10 － 19 were
dissolved with actone， and submitted to HPLC
(ODS-Symmtryprep，7 μm，i． d． 7． 8 mm ×150 mm
column;MeOH-H2O 2∶ 1，v /v;2 mL /min)to give
compound E(94． 7 mg) ，compound F(27． 9 mg) ，
and compound I (26． 5 mg)． Subfractions 21 － 39
(1． 1 g)were processed again on silica gel (200 －
300 mesh)column chromatography using PE-actone
(85∶ 15，v /v)to give compound G (166． 7 mg)．
The rest subfractions 21 － 39， which exhibited
insecticidal activity，were subjected to Sephadex LH-
20 column chromatography using acetone to give
compound G (33． 1 mg)and compound B (17． 6 mg)．
2． 5 Identification of compounds isolated from
the extracts of T． purpurea bark
1H and 13C-NMR were recorded by using a
Bruker AVANCE-500 instrument． EI-MS and HR-
EI-MS were accomplished on a Thermo Finnigan
MAT-95XP instrument． TLC spots were visualized
by UV irradiation (254 and 365 nm) ，and by
spraying with the mixture of methanol and H2SO4
(1∶ 1，v /v)followed by heating． Optical rotations
were recorded with a Perkin-Elmer 343 polarimeter．
Melting points were uncorrected and determined on
an XT4A digital micromelting point apparatus．
2． 6 Data statistics and analysis
The insecticidal activity tests with higher than
20% mortality in controls were discarded and then
repeated． If the control mortalities ranged between
5% and 20%，they were corrected using Abbott’s
formula (Huang， 2000)． LC50 (median lethal
concentration)and LD50(median lethal dosage)of
compounds against the tested pests were calculated
by Probit Analysis (DPS software，version 9． 5)．
The 95% confidence interval，values and degrees of
freedom of the χ2 goodness of fit tests，and regression
equation were calculated and analyzed． Whenever
the goodness of χ2 was found to be significant (P ＜
0． 05) ，a heterogeneity correction factor was used in
the calculation of the confidence limits．
3 RESULTS
3． 1 Identification of compounds
Compound A is colourless needle crystal． 1H
NMR［500 MHz，(CD3)2CO］:δH 1． 41 (3 H，s，
-CH3) ，142 (3 H，s，-CH3) ，2． 86 (1 H，dd，J =
17． 1 Hz，3． 1 Hz，H-3) ，3． 17 (1 H，dd，J = 17． 0
Hz，12． 8 Hz，H-3) ，5． 59 － 5． 63 (2 H，m，H-2，
H-3″) ，5． 90 (1 H，s，H-6) ，6． 51 (1 H，d，J =
10． 0 Hz，H-4″) ，7． 40 (1 H，t，J = 7． 4 Hz，H-
4) ，7． 45 (2 H，t，J = 7． 7 Hz，H-2，H-6) ，
7． 58 (2 H，d，J = 7． 4 Hz，H-3，H-5) ，12． 22
(s， 1 H， HO-5 ) ;13C NMR (125 MHz，
(CD3)2CO) :δC 29． 4 (-CH3) ，29． 7 (-CH3) ，
44． 5 (C-3) ，79． 9 (C-2″) ，81． 1 (C-2) ，98． 7 (C-
6) ，103． 7 (C-10) ，104． 6 (C-9) ，117． 1 (C-4″) ，
128． 2 (C-2，C-6) ，128． 6 (C-4) ，130． 5 (C-
3″) ，130． 6 (C-3，C-5) ，140． 9 (C-1) ，158． 9
(C-8) ，163． 8 (C-7) ，165． 4 (C-5) ，198． 1 (C-
4)． The spectroscopic data is consistent with that
listed in the literature (Waterman and Mahmoud，
1985;Andrei et al．，2000) ，socompound A is
identified as obovatin．
Compound B is colourless needle crystal． 1H
NMR［500 MHz，(CD3)2CO］:δH 1． 42 (3 H，s，-
CH3) ，1． 44 (3 H，s，-CH3) ，2． 69 (1 H，dd，J =
16． 3 Hz，3． 0 Hz，3-H) ，2． 95 (1 H，dd，J = 16． 3
Hz，12． 7 Hz，3-H) ，3． 82 (3 H，s，-OCH3) ，
12 期 LI You-Zhi et al．:Isolation and identification of insecticidal compounds from Tephrosia purpurea 1371
5． 53 (1 H，dd，J = 12． 7 Hz，3． 0 Hz，H-2) ，5． 57
(1 H，d，J = 10． 0 Hz，H-3″) ，6． 10 (1 H，s，H-
6) ，6． 56 (1 H，d，J = 10． 0 Hz，H-10) ，7． 37 (1
H，t，J = 7． 2 Hz，H-4) ，7． 44 (2 H，t，J = 7． 8
Hz，H-2，H-6) ，7． 56 (2 H，d，J = 7． 2 Hz，H-
3，H-5) ;13C NMR (125 MHz，CDCl3) :δC 29． 4
(-CH3) ，29． 6 (-CH3) ，47． 3 (C-3) ，57． 3 (-
OCH3) ，79． 5 (C-2″) ，80． 9 (C-2) ，95． 6 (C-6) ，
104． 5 (C-10) ，107． 6 (C-8) ，117． 7 (C-4″) ，
128． 0 (C-2，6) ，128． 4 (C-4) ，130． 2 (C-3″) ，
130． 5 (C-3，5) ，141． 5 (C-1) ，160． 5 (C-9) ，
161． 4 (C-7) ，164． 1 (C-5) ，188． 8 (C-4)． The
spectroscopic data is consistent with that listed in the
literature (Andrei et al．，2000) ，so compound B is
identified as pongachin．
Compound C is white plate crystal． mp:162 －
164℃，［α］25D = － 228° (C0． 024，benzene)． MS
(m/z) :394(M +) ，192 (100 ) ，149，191;1H
NMR (500 MHz，CDCl3) :δ = 1． 77 (3 H，s，H-
3″) ，2． 95 (1 H，dd，J = 15． 7 Hz，8． 1 Hz，H-2) ，
3． 31 (1 H，dd，J = 15． 6 Hz，9． 8 Hz，H-2) ，3． 77
(3H，s，OCH3) ，3． 81 (3H，s，OCH3) ，3． 84
(1 H，d，J = 3． 0 Hz，H-6) ，4． 17 (1H，d，J =
12． 1 Hz，H-12a) ，4． 60 (1H，dd，J = 12． 1 Hz，
J = 3． 0 Hz，H-6) ，4． 93 (1H，s，H-2″) ，5． 08
(1H，s，H-11) ，5． 24 (1H，t，J = 9． 30 Hz，H-
2) ，6． 45 (1H，s，H-4) ，6． 50 (1H，d，J = 8． 5
Hz，H-10) ，6． 77 (1H，s，H-1) ，7． 83 (1H，d，
J = 8． 5 Hz，H-11) ;13C NMR (125 MHz，CDCl3) :
δC 17． 1 (C-3″) ，31． 3 (C-3) ，44． 6 (C-12a) ，
55． 8 (C22-OMe) ，56． 3 (C23-OMe) ，66． 3 (C-6) ，
72． 2 (C-6a) ，87． 8 (C-2) ，100． 9 (C-4) ，104． 8
(C-10) ，110． 4 (C-12b) ，112． 6 (C-1) ，112． 9
(C-11a) ，113． 3 (C-8) ，129． 9 (C-2″) ，143． 0
(C-1″) ，143． 9 (C-2) ，147． 4 (C-3) ，149． 5 (C-
4a) ，157． 9 (C-7a) ，167． 3 (C-9) ，188． 9 (C-
12)． Its MS data is consistent with rotenone’s (Li
and Xu，2007) ，and the spectroscopic data is
consistent with that listed in the literature (Li and
Xu，2007) ，so compound A is identified as rotenone．
Compound D is colourless needle crystal． 1H
NMR (500 MHz，CDCl3) :δH 1． 77 (3H， s，
CH3) ，2． 95 (1 H，dd，J = 15． 7 Hz，8． 1 Hz，H-
1) ，3． 31 (1 H，dd，J = 15． 7 Hz，9． 8 Hz，H-
1) ，3． 82 (3 H，s，OCH3) ，4． 18 (1 H，d，J =
12． 0 Hz，H-6) ，4． 60 (1 H，dd，J = 12． 0 Hz，3． 0
Hz，H-6) ，4． 91 (1 H，t，J = 3． 2 Hz，H-2″) ，
4． 93 (1 H，s，H-2″) ，5． 07 (1 H，s，H-6a) ，5． 23
(1 H，d，J = 5． 4 Hz，H-2) ，5． 25 (1 H，s，
-OH) ，6． 44 (1 H，s，H-4) ，6． 50 (1 H，d，J =
8． 5 Hz，H-10) ，6． 83 (1 H，s，H-1) ，7． 82 (1 H，
d，J = 8． 5 Hz) ;13C NMR (125 MHz，CDCl3) :δC
17． 1 (C-3″) ，31． 3 (C-3) ，44． 6 (C-12a) ，55． 9
(-OMe) ，66． 3 (C-6) ，72． 2 (C-6a) ，87． 8 (C-
2) ，100． 1 (C-4) ，104． 8 (C-10) ，105． 9 (C-
12b) ，112． 5 (C-1) ，112． 9 (C-1″) ，113． 1 (C-
11a) ，113． 3 (C-8) ，130． 0 (C-2″) ，140． 2 (C-
2) ，143． 1 (C-11) ，146． 7 (C-4a) ，146． 9 (C-3) ，
157． 8 (C-7a) ，167． 3 (C-9) ，188． 6 (C-12)． The
spectroscopic data is consistent with that shown in
the literature (Charalambous et al．，1995) ，so
compound D is identified as 2-hydroxyrotenone．
Compound E is brown paste． 1H NMR (500
MHz，CDCl3) :δH 1． 76 (3 H，s，H-3″，-CH3) ，
2． 94 (1 H，dd，J = 15． 8 Hz，8． 2 Hz，H-3) ，
3． 29 (1 H，dd，J = 15． 8 Hz，9． 8 Hz，H-3) ，
3． 73 (3H，s，-OCH3) ，3． 82 (3 H，s，-OCH3) ，
4． 50 (1 H，d，J = 11． 6 Hz，H-6) ，4． 61 (1 H，d，
J = 2． 4 Hz，H-6 ) ，4． 59 (1 H，s，H-6a) ，4． 94
(1 H，s，H-2″，= CH2) ，5． 07 (1 H，s，H-2″，=
CH2) ，5． 24 (1 H，t，J = 9． 0 Hz，H-2) ，6． 49
(1 H，s，H-4) ，6． 54 (1 H，d，J = 8． 6 Hz，H-
10) ，6． 56 (1 H，s，H-1) ，7． 83 (1 H，d，J = 8． 6
Hz，H-11) ;13C NMR (125 MHz，CDCl3) :δC17． 1
(C-3″) ，31． 1 (C-3) ，55． 9 (-OMe) ，56． 4
(-OMe) ，63． 9 (C-6) ，67． 6 (C-12a) ，87． 9 (C-
2) ，101． 1 (C-4) ，105． 3 (C-10) ，108 (C-12b)
109． 5 (C-1) ，118 (C-11a) ，112． 7 (C-2″) ，113． 2
(C-8) ，130． 1 (C-11) ，142． 9 (C-1″) ，144． 0 (C-
2) ，148． 4 (C-4a) ，151． 2 (C-3) ，157． 7 (C-7a) ，
168． 0 (C-9) ，191． 1(C-12)． The spectroscopic
data is consistent with that listed in the literature
(Phrutivorapongkul et al．，2002) ，so compound E is
identified as 12a-hydroxyrotenone．
Compound F is colourless needle crystal．
［α］25D = － 265°(C0． 01，CDCl3)．
1H NMR ［500
MHz，(CD3)2CO］:δH1． 72 (3 H，s，-CH3) ，
1． 73 (3 H，s，-CH3) ，3． 33 (2 H，d，J = 7． 3
Hz，H-1) ，3． 50 － 3． 59 (2 H，m，H-6) ，4． 21 (1
H，dd，J = 10． 1 Hz，4． 0 Hz，H-6a) ，5． 33 － 5． 37
(1 H，m，H-11a) ，5． 46 (1 H，d，J = 6． 6 Hz，H-
2) ，5． 90 (1 H，d，J = 1． 0 Hz，-OCH2O-) ，5． 92
(1 H，d，J = 1． 0 Hz，-OCH2O-) ，6． 37 (1 H，s，
H-4) ，6． 40 (1 H，s，H-10) ，6． 87 (1 H，s，H-
7) ，7． 15 (1 H，s，H-1) ，8． 47 (1 H，s，-OH) ;
13C NMR ［125 MHz，(CD3 )2CO］: δC 18． 8
(-CH3) ，26． 9 (-CH3) ，29． 4 (C-1) ，42． 2 (C-
6a) ，68． 1 (C-6 ) ，80． 6 (C-11a ) ，95． 0
(-OCH2O-) ，103． 1 (C-10) ，104． 6 (C-4) ，106． 9
(C-7) ，113． 6 (C-1a) ，120． 6 (C-2) ，123． 9 (C-
6b) ，124． 9 (C-2) ，133． 3 (C-3) ，133． 5 (C-
1) ，143． 5 (C-4a) ，149． 9 (C-9) ，156． 4 (C-
10a) ，156． 7 (C-4a ) ，158． 0 (C-3 )． The
spectroscopic data is consistent with that listed in the
literature (Reyes-Chilpa et al．， 1994 ) ，so
compound F is identified as (-)-edunol．
1372 昆虫学报 Acta Entomologica Sinica 54 卷
Compound G is white amorphous powder．
［α］25D = － 17． 4°． It has a molecular formula of
C21H18O6 as determined from the ion peaks at m/z
366［M］+ and 335［M-CH2OH］
+ in the EI-MS and
m/z 366． 1092［M］+ in the HR-EI-MS． Its 1H and
13C NMR spectra (Table 1)were closely similar to
those of emoroidocarpan (Palazzino et al．，2003) ，
except the absence of proton and carbon signals for
3-Me． Instead， the spectra exhibited resonances
indicating the presence of an oxygenated methylene
［δH 4． 28 (1H，d，J = 13． 8 Hz) ，4． 24 (1H，d，
J = 13． 8 Hz) ;δC 63． 0］． In the HMBC spectrum
(Table 1) ，the oxygenated methylene protons were
observed to be correlated with C-2 (δC 84． 6) ，C-3
(δC147． 4) ，and C-5 (δC 112． 3)． These findings
in combination with the molecular formula showed
that a hydroxyl group is attached to C-4 in this
compound． The relative stereochemistry was deduced
to be identical with that of emoroidocarpan from the
1H NMR coupling constant (J = 6． 8 Hz)between
H-6a and H-11a and the NOESY spectrum (Table
1) ，in which an NOE interaction is observed
between H-6a and H-11a． Thus，the compound is
identified as 4-hydroxyemoroidocarpan．
Table 1 1H and 13C NMR data，and NOESY and HMBC correlations of 4-hydroxyemoroidocarpan
Position δH(J in Hz) NOESY δC HMBC
1 7． 27 s 126． 5 C-3，4a，11a，1
1a 112． 4
2 120． 6
3 160． 8
4 6． 41 s 98． 5 C-1a，2，3，4a
4a 156． 1
6 4． 21 dd (5． 0，11． 0) ，3． 62 t (11． 0) H-6a 66． 6
6a 3． 47 ddd (5． 0，6． 8，11． 0) H2-6，H-11a 40． 2
6b 118． 0
7 6． 72 s 104． 8 C-6a，8，9，10a
8 141． 7
9 148． 1
10 6． 43 s 93． 8 C-6b，8，9，10a
10a 154． 2
11a 5． 47 d (6． 8) H-6a 79． 0 C-1，1a，4a，6，6a
1 3． 36 dd (9． 5，15． 5) ，3． 12 dd (8． 0，15． 5) H-2 34． 4 C-1，2，3，2，3
2 5． 37 t (8． 0) H2-1 84． 6 C-2，3，1，3，4，5
3 147． 4
4 4． 28 d (13． 8) ，4． 24 (13． 8) 63． 0 C-2，3，5
5 5． 27 br s 112． 3 C-2，3，4
OCH2O 5． 92 d (1． 1) ，5． 89 d (1． 1) 101． 3 C-8，9
Compound H is colourless needle crystal． mp:
150 － 152℃，［α］25D = － 304° (C0． 05，CHCl3)．
1H
NMR (500 MHz，CDCl3) :δH 1． 75 (3H，s，CH3-
OOC-) ，3． 65 (1H，t，J = 5． 3 Hz，H-6) ，3． 85
(6H，s，2 × OCH3) ，4． 32 － 4． 35 (1H，m，H-6) ，
4． 53 (1H，t，J = 11． 3 Hz，H-12a) ，4． 98 － 5． 03
(1H，m，H-6a) ，6． 43 (1H，s，H-4) ，6． 44 (1H，
d，J = 4． 6 Hz，H-12) ，6． 69 (1H，s，H-1) ，6． 87
(1H，d，J = 2． 0 Hz，H-3) ，7． 11 (1H，d，J = 8． 4
Hz，H-10) ，7． 21 (1H，d，J = 8． 4 Hz，H-11) ，7． 57
(1H，d，J = 2． 2 Hz，H-2) ;13C NMR (125 MHz，
CDCl3) :δC 112． 0 (C-1) ，143． 6 (C-2) ，146． 9 (C-
3) ，100． 2 (C-4) ，148． 7 (C-4a) ，64． 4 (C-6) ，
66． 6 (C-6a) ，149． 5 (C-7a) ，108． 6 (C-8) ，156． 8
(C-9) ，104． 0 (C-10) ，126． 8 (C-11) ，111． 3 (C-
11a) ，69． 1 (C-12) ，36． 7 (C-12a) ，117． 0 (C-
12b) ，144． 3 (C-2)105． 2 (C-3) ，56． 5 (2-OMe) ，
55． 9 (3-OMe) ，20． 8 (-CH3) ，170． 4 (-COO-)． The
spectroscopic data is consistent with that listed in the
literature (Lin et al．，1993) ，so compound H is
identified as 12-acetyelliptinol．
Compound I is brown crystal． 1H NMR (500
12 期 LI You-Zhi et al．:Isolation and identification of insecticidal compounds from Tephrosia purpurea 1373
MHz，CDCl3) :δH 3． 78 (3 H，s，OCH3) ，5． 97
(2 H，s，-OCH2O-) ，6． 64 (1 H，s，H-3″) ，6． 83
(1 H，dd，J = 2． 1 Hz，0． 8 Hz，H-3) ，6． 90 (1 H，
s，H-6″) ，7． 50 (1 H，s，H-8) ，7． 68 (1 H，s，H-
5) ，7． 69 (1 H，d，J = 2． 2 Hz，H-2) ，7． 89 (1 H，
s，H-4) ;13C NMR (125 MHz，CDCl3) :δC 56． 8
(-OMe) ，95． 5 (C-3″) ，99． 5 (C-8) ，101． 5
(-OCH2O-) ，106． 4 (C-3) ，110． 3 (C-6″) ，116． 2
(C-1″) ，116． 2 (C-4a) ，119． 6(C-5) ，124． 0 (C-
3) ，124． 8 (C-6) ，141． 3 (C-5″) ，142． 4 (C-4) ，
146． 7 (C-2) ，148． 8 (C-4″) ，151． 6 (C-8a) ，152． 9
(C-2″) ，156． 1 (C-7) ，160． 7 (C-2)． The
spectroscopic data is consistent with that listed in the
literature (Phrutivorapongkul et al．， 2002 ) ，so
compound I is identified as pachyrrhizine．
Compound J is yellow crystal． mp:101 － 103℃ ．
1H NMR (500 MHz，CDCl3) :δH 7． 63 (1H，d，J =
9． 5 Hz，H-4) ，7． 11 (1H，d，J = 8． 5 Hz，H-8) ，
6． 90 (1H，d，J = 8． 5 Hz，H-7) ，6． 46 (1H，s，H-
5) ，6． 24 (1H，d，J = 9． 5 Hz，H-3) ，4． 11 (3H，s，
C11-OMe) ;
13C NMR (125 MHz，CDCl3) :δC 160． 4
(C-2) ，112． 6 (C-3) ，144． 3 (C-4) ，112． 1 (C-5) ，
152． 1 (C-6) ，113． 2 (C-7) ，123． 3 (C-8) ，147． 2
(C-9) ，133． 7 (C-10) ，61． 8 (C-11)． The
spectroscopic data is consistent with that listed in the
literature (Kitamura et al．，2003;Kotani et al．，2004;
Oyamada and Kitamura，2006) ，so compound J is
identified as 6-methoxycoumarin．
3． 2 Insecticidal activity of compounds
The LC50 or LD50values were as showed in Table
2． Based on the LC50 or LD50 values，ten potential
insecticidal compounds against A． albopictus larvae
were arranged in the following order from high to low:
12a-hydroxyrotenone ＞ 4-hydroxyemoroidocarpan ＞
pachyrrhizine ＞ rotenone ＞ 6-methoxycoumarin ＞(-)-
edunol ＞ obovatin ＞ pongachin ＞ 12-acetyelliptinol ＞
2-hydroxyrotenone，with the LC50 values of 12． 5，
22． 1，25． 0 mg /L，34． 1，43． 4，58． 4，121． 9，191．
0，219． 8 and 250． 0 mg /L， respectively． Three
compounds，i． e．，12a-hydroxyrotenone，rotenone and
4-hydroxyemoroidocarpan， exhibited insecticidal
activity against M． persicae adults and the 3rd larvae
of P． xylostella， and their insecticidal potential
against M． persicae adults was arranged in the
following order from high to low:12a-hydroxyrotenone
＞ rotenone ＞ 4-hydroxyemoroidocarpan;and their
insecticidal potential to the 3rd P． xylostella larvae
was arranged in the following order from high to low:
12a-hydroxyrotenone ＞ 4-hydroxyemoroidocarpan ＞
rotenone．
Table 2 Insecticidal activity of the compounds from Tephrosia purpurea bark against the 4th instar larvae of Aedes albopictus，
the 3rd instar larvae of Pluttella xylostella and the adults of Myzus persicae
Compounds Insects Toxicity regressionequation
LC50(mg /L)
(95% confidence interval)
LD50(μg / individual)
(95% confidence interval) χ
2
4-Hydroxyemoroidocarpan A． albopictus y = 2． 3 + 1． 9x 22． 1 (16． 6 － 28． 9) 0． 8590
Rotenone y = 2． 9 + 1． 4x 34． 1 (22． 4 － 49． 2) 0． 5385
2-Hydroxyrotenone y = 0． 2 + 1． 9x 250． 0 (190． 3 － 333． 5) 2． 5078
12-Acetyelliptinol y = 0． 9 + 1． 7x 219． 8 (163． 1 － 302． 1) 0． 9553
12a-Hydroxyrotenone y = 3． 4 + 1． 4x 12． 5 (8． 3 － 17． 7) 0． 2567
Pachyrrhizine y = 1． 3 + 2． 7x 25． 0 (18． 9 － 30． 5) 1． 6413
Obovatin y = 2． 1 + 1． 4x 121． 9 (83． 1 － 179． 0) 1． 8289
6-Methoxycoumarin y = 1． 7 + 2． 0x 43． 4 (32． 5 － 56． 5) 3． 2719
(-)-Edunol y = 2． 8 + 1． 2x 58． 4 (30． 9 － 87． 3) 0． 2940
Pongachin y = 0． 2 + 2． 1x 191． 0 (146． 2 － 247． 7) 0． 8408
4-Hydroxyemoroidocarpan P． xylostella y = 2． 7 + 1． 4x 49． 8 (33． 7 － 73． 4) 0． 6642
Rotenone y = 0． 9 + 1． 8x 197． 1 (144． 4 － 265． 2) 0． 9732
12a-Hydroxyrotenone y = 2． 4 + 1． 6x 40． 8 (28． 2 － 55． 8) 0． 4494
4-Hydroxyemoroidocarpan M． persicae y = 2． 7 + 1． 4x 49． 9 (33． 7 － 73． 4) 0． 6642
Rotenone y = 4． 7 + 1． 2x 1． 9 (1． 1 － 2． 8) 0． 5257
12a-Hydroxyrotenone y = 5． 0 + 1． 5x 0． 9 (0． 6 － 1． 4) 0． 3984
1374 昆虫学报 Acta Entomologica Sinica 54 卷
4 DISCUSSION
In this study， ten known compounds with
insecticidal property were isolated and identified
from T． purpurea bark by activity-guided
fractionation with column chromatography，including
two coumarins ( 6-methoxycoumarin and
pachyrrhizine)and eight flavonoids［rotenone，12a-
hydroxyrotenone， 4-hydroxyemoroidocarpan，(-)-
edunol， obovatin， pongachin， 12-acetyelliptinol，
and 2-hydroxyrotenone］． Except rotenone and 12a-
hydroxyrotenone，the others were isolated from T．
purpurea bark for the first time．
Various compounds (including flavonoids，
terpenoids，phenolics and alkaloids)existed in plant
extracts and jointly or independently contributed to
bioefficacy such as insecticidal，ovicidal，repellent，
and antifeeding activities against various insect
species (Isman，2000)． Some researchers focused
on the determination of the distribution，nature，and
practical use of plant extracts-derived chemical
constituents with insecticidal activities (Pavela and
Herda，2007;Li et al．，2007，2011)． The results
of this study indicated that at least two classes of
phytochemicals， flavonoids and coumarins， with
insecticidal property existed in T． purpurea bark．
Flavonoids play a key role in stress response
mechanisms in plants，which act as antioxidants or
as enzyme inhibitors involved in photosynthesis and
cellular energy transfer processes，and may serve as
the precursor of toxic substances with insecticidal
activity (Ververidis et al．，2007)． The adaptive role
of flavonoids in plant defense against bacterial，
fungal and viral diseases has been confirmed． The
methanol extracts from T． purpurea bark exhibited
insecticidal activity against various species of insect
pests including A． albopictus larvae，with LC50 value
being 97． 7 mg /L against the 4th instar larvae of A．
albopictus at 24 h after treatment (Li et al．，2007)．
In this study，eight flavonoids and two coumarins
independently exhibited insecticidal activity against
the mosquito larvae (Table 2)． Thus，insecticidal
activity of the bark extracts against the mosquito
larvae is due to the joint contribution of these
compounds．
Earlier phytochemical research revealed that
flavonoids including isoflavones， flavones，
flavanones，chalcones，flavonols and rotenoids were
the main constituents occurring in this plant (Sinha
et al．，1982)． Within the group of flavonoids，5，7-
oxygenated and 7-oxygenated compounds
characterized by the presence of C-8 prenyl unit are
well known． In many cases， these prenylated
flavones have undergone further substitution and
cyclization leading to complex molecules (Sinha et
al．，1982)． Our experiment indicated that some
prenylated flavonoids probably turn into more
complex compounds because of the above-mentioned
substitution and cyclization． Some flavonoids were
isolated from T． purpurea bark for the first time，
which provides proof to support the above-mentioned
hypothesis．
Coumarins are also a major class of secondary
metabolites in plants． To date there are about 900
coumarins documented in plants and the list is
steadily increasing (Chen， 2004 )． Most of
coumarins exhibit bioefficacy in plant defense against
bacterial，fungal and viral diseases，and a few with
light-sensitive character often exhibit insecticidal
activities (Chen， 2004)． In this study， two
coumarins (6-methoxycoumarin and pachyrrhizine)
exhibited insecticidal activity (Table 2) ，and their
mechanism of action deserves to be further
researched．
Elucidation of insecticidal compounds in plants
is the basis to develop new botanical insecticides
(Belmain et al．， 2001 )． Derris elliptica，
Azadirachta indica and Chryaanthemum
cinerariaefotiumvis are very successful examples．
Azadirachtin isolated from A． indica showed great
bioactivity against pests，so did rotenoids isolated
from D． spp． and pyrethrin I isolated from C．
cinerariaefotiumvis (Xu，2001)． Azadirachtin and
rotenone have been explored and introduced into the
market to control various species of agricultural
pests，and pyrethrin I as a lead compound has been
developed into a series of insecticides on the basis of
structure optimization．
According to this study，12a-hydroxyrotenone
and 4-hydroxyemoroidocarpan exhibited insecticidal
activities against three species of pests (Table 2) ，
especially to P． xylostella larvae，and the corres-
ponding LD50 value is lower than that of the
conventional botanic insecticidal compound
rotenone，suggesting that the insecticidal activity of
the two compounds against P． xylostella larvae is
superior to that of rotenone． P． xylostella is one of
the most important insect pests on brassica crops
(Ma et al．，2005)． At present，chemical control of
P． xylostella is becoming less effective because many
populations of this pest developed resistance to some
insecticides (Ma et al．， 2005)． So the two
compounds deserve to be further evaluated before they
are developed into insecticides by structure optimi-
zation and directly used as insecticidal ingredient．
12 期 LI You-Zhi et al．:Isolation and identification of insecticidal compounds from Tephrosia purpurea 1375
ACKNOWLEDGMENTS The authors greatly thank Prof．
Zhong Ye-Cong from Guangxi Academy of Forestry for his help in
identification of the plant specimens．
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1376 昆虫学报 Acta Entomologica Sinica 54 卷
灰毛豆树皮中的杀虫成分及其杀虫活性
李有志1，2，李冠华2，魏孝义4，刘仲华1，徐汉虹3，*
(1． 湖南农业大学，国家植物功能成分利用工程技术研究中心，长沙 410128;
2． 湖南农业大学生物安全科技学院，植物病虫害生物学与防控湖南省重点实验室，长沙 410128;
3． 华南农业大学资源环境学院，天然农药与化学生物学教育部重点实验室，广州 510642;
4． 中国科学院华南植物园，广州 510650)
摘要:为确定灰毛豆 Tephrosia purpurea树皮甲醇提取物中的杀虫成分，以白纹伊蚊 Aedes albopictus 4 龄幼虫为靶标昆
虫，在活性跟踪的基础上利用色谱技术分离其活性成分，然后根据各化合物的核磁共振图谱和质谱数据确定化合物
的结构，并利用玻片载蚜法和点滴法测定了各化合物对桃蚜 Myzus persicae 无翅蚜成虫和小菜蛾 Pluttella xylostella 3
龄幼虫的毒杀活性。结果表明:从该植物树皮甲醇提取物中共分离、鉴定了 10 个对白纹伊蚊幼虫具有毒杀作用的
化合物，即 12a-羟基鱼藤酮(12a-hydroxyrotenone) ，4-hydroxyemoroidocarpan，豆薯内酯(pachyrrhizine) ，鱼藤酮
(rotenone) ，6-甲 氧 基 香 豆 素 (6-methoxycoumarin) ，(-)-edunol， obovatin， pongachin， 12-acetyelliptinol 和 2-
hydroxyrotenone。这些化合物对该蚊虫幼虫处理 24 h的 LC50值分别是 12． 5，22． 1，25． 0，34． 1，43． 4，58． 4，121． 9，
191． 0，219． 8 和 250． 0 mg /L。3 个化合物(4-hydroxyemoroidocarpan，鱼藤酮和 12a-羟基鱼藤酮)对桃蚜成虫和小菜
蛾 3 龄幼虫表现出毒杀活性，它们对桃蚜 24 h的 LC50值分别是 49． 9，1． 9 和 0． 9 mg /L，对小菜蛾幼虫 24 h的 LD50值
分别是 49． 8，197． 1 和 40． 9 μg /头。首次从该植物中分离得到 6 个已知的黄酮类化合物［4-hydroxyemoroidocarpan，
2-hydroxyrotenone，(-)-edunol，12-acetyelliptinol，pongachin和 obovatin］和 2 个已知的香豆素类化合物(6-甲氧基香豆
素和豆薯内酯)。阐明这些杀虫化合物的结构不仅有利于理解植物和昆虫的关系，而且有助于评价该植物及其活性
化合物作为植物源农药开发利用的潜力。
关键词:灰毛豆;杀虫化合物;杀虫活性;白纹伊蚊;小菜蛾;桃蚜
中图分类号:Q965． 9 文献标志码:A 文章编号:0454-6296(2011)12-1368-09
(责任编辑:赵利辉)