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Elseiver 1
Elseiver 1
Departments of Biology and Chemistry, University of Ottawa, Ottawa, Ont., Canada ON K1N 6N5
b
Agriculture and Agri-Food Canada, Winnipeg, Canada MB R3T 2M9
c
Herbario Juvenal, Universidad Nacional, Heredia 3000, Costa Rica
d
Departamento de Farmacia, Facultad de Quimica, UNAM, Coyoacan, Mexico, D.F., Mexico
Accepted 30 November 2005
Abstract
Terpenes isolated from tropical species of the Rutales were tested for insect antifeedant activity against rice weevil, Sitophilus oryzae
(L.) using a our disk bioassay that requires only small amounts of compounds (0, 0.05, 0.25 and 0.50% w/w). At 0.50% (w/w) ve
compounds isolated from Lansium domesticum (iso-onoceratriene, 3-keto-22-hydroxyonoceradiene, onoceradienedione, lansiolic acid
and lansiolic acid A) were shown to exhibit signicant antifeedant activity. Humilinolide C and D isolated from Swietenia humilis, and
gedunin from Cedrela odorata, were also active at 0.50% (w/w). The most interesting results were obtained from the spirocaracolitones
from Ruptiliocarpon caracolito which produced total feeding inhibition at 0.50% and potent antifeedant activity at concentrations as low
as 0.05%. In conclusion, the antifeedant bioassay provides a rapid and inexpensive method for screening novel compounds available in
small quantities to assess their activity as insect antifeedants.
r 2006 Elsevier Ltd. All rights reserved.
Keywords: Insect control agents; Antifeedants; Sitophilus oryzae
1. Introduction
In the New World tropics as well as in Southeast Asia,
native trees of the order Rutales are well known for the
production of bioactive terpenoids (Isman et al., 1997;
Arnason et al., 1993, 1987). In particular, the plant family
Meliaceae is noted for the production of useful bitter
principles which are insect antifeedant and growth-reducing substances with low mammalian toxicity (Butterworth
and Morgan, 1968; Arnason et al., 1985; Schmutterer,
1990; Isman et al., 1997). In recent years, bioactive
terpenoids have been isolated from different neotropical
species including Cedrela odorata L., Ruptilocarpon caracolito L. (MacKinnon, 1995), and Swietenia humilis Zucc.
(Jimenez et al., 1997).
0022-474X/$ - see front matter r 2006 Elsevier Ltd. All rights reserved.
doi:10.1016/j.jspr.2005.11.005
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93
2.2. Bioassay
CH3
H3C
H3C
CH3
CH3
CH3
CH3
H3C
H3C
CH2
H3C
CH2
O
CH3
H3C
H3C
ONOCERATRIENE
CH3
ONOCERADIENEDIONE
COOH
OH
H3C
CH3
H3C
O
H3C
H3C
CH3
CH3
H3C
CH2
O
H3C
CH3
3-KETO-22-HYDROXYONOCERADIENE
CH2
CH3
3-KETOLANSIOLIC ACID
COOH
H3C
COOH
CH2
H3C
CH2
H3C
CH3
CH3
CH2
H3C
CH3
CH3
CH3
CH2
H2C
CH2
HO
HO
H3C
CH3
LANSIOLIC ACID
O
H3C
CH3
LANSIOLID ACID A
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CH3
CH3
OAc
O
O
CH3
O
O
OAc
MeO
O
O
OAc
OAC
OAc
H3C
CH3
SPIROCARACOLITONE B
GEDUNIN
HO
AcO
OH
AcOH2C
OAc
OCOPh
H3CO
O
O
OAc
O
OAc
OAc
MeO
OR
H3CO
R=CO C(CH3)=CHCH3
SPIROCARACOLITONE D
SPIROCARACOLITONE E
O
Me
Me
OAc Me
H
H Me
H
O
MeO2C
O
Me
OH
Me
OCOCH(CH3)2
HUMILINOLIDE B
H
MeO2C
Me
O
H Me
H
O
O
MeO2C
Me
Me
O
H
OAc
OCOC(CH3)=CHCH3
HUMILINOLIDE C
Fig. 2. Structures of triterpenes isolated from neotropical plants.
Me
OH
Me
OCOCH3
HUMILINOLIDE D
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Table 1
Antifeedant activity of crude extracts and pure compounds isolated from
Lansium domesticum against Sitophilus oryzae (0.5% w/w)
Treatment
Consumption of diet
(% control7SEM)
Control
3-ketolansiolic acid
Iso-onoceratriene
Lansiolic acid
Lansiolic acid A
3-keto-22-hydroxyonoceradiene
Onoceradienedione
Ethyl acetate fraction
Hexane fraction
Water fraction
100.0710.2a
68.9717.4a,b
64.777.5b
63.273.8b
56.174.5b
53.873.4b
40.176.2b
0.0c
0.0c
184.6729d
Table 2
Antifeedant activity of spirocaracolitones against Sitophilus oryzae
Multiple range test using Tukeys test (Po0.05). The same letters denote
treatments not signicantly different from each other.
P value
Compound
Concentration
(% w/w)
Consumption
of diet
(% control7SEM)
Control
Spirocaracolitone B
0
0.05
0.25
0.50
100.078.5a
67.176.1b
8.873.9c
0.0
o 0.05
o 0.001
o 0.001
Spirocaracolitone D
0.05
0.25
0.50
74.676.3b
2.971.3c
0.0
0.05
o0.001
o0.001
Spirocaracolitone E
0.05
0.25
0.50
78.3710.1a,b
19.079.9d
0.0
40.08
o0.001
o0.001
P value
40.05
o0.05
o0.01
o0.01
o0.01
o0.001
o0.001
o0.001
o0.001
95
Multiple range test using Tukeys test (Po0.05). The same letters denote
treatments not signicantly different from each other.
Table 3
Antifeedant activity of humilinolides and gedunin against Sitophilus
oryzae
Compound
Control
Humilinolide B
Humilinolide C
Humilinolide D
Gedunin
Concentration
(% w/w)
0.50
0.50
0.50
0.50
Consumption
of diet
(% control7SEM)
10077.4a
79.7716.7a
24.871.0b
65.2711.1c
31.276.3b
P value
40.05
o0.05
o0.05
o0.05
Multiple range test using Tukeys test (Po0.05). The same letters denote
treatments not signicantly different from each other.
Acknowledgements
Funding was provided by the Natural Science and
Engineering Research Council of Canada and Ontario
Ministry of Science and Technology.
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