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Department of Pest Control and Environmental Protection, Faculty of Agriculture (Damanhour), Alexandria University, Damanhour, Egypt
b Department of Pesticide Chemistry, Faculty of Agriculture, Alexandria University, 21545 El-Shatby, Alexandria, Egypt
Received 24 January 2007; received in revised form 22 April 2007; accepted 24 April 2007
Abstract
Insecticidal, antifeedant and antifungal activities of two glucosides isolated from the seeds of jojoba plant, Simmondsia chinensis
(Link) Schneider, were tested. Bioassay-driven fractionations of the chloroform extract of the plant seeds over silica gel columns
followed by recrystallization afforded two glucosides, simmondsin and simmondsin 2 -ferulate. The structure of these glucosides was
confirmed by physico-chemical properties and spectroscopic analyses. In topical application assay, simmondsin and simmondsin
2 -ferulate showed a strong insecticidal activity against the third instar larvae of Spodoptera littoralis Boisduval (Lepidoptera:
Noctuidae) with LD50 values of 1.49 and 2.58 g/larva, respectively. Both compounds showed antifeedant activity against S.
littoralis in a concentration-dependent manner. In addition, the isolated compounds showed moderate to high antifungal activity
against four plant pathogenic fungi. This is the first study on the insecticidal, antifeedant and antifungal activities of these glucosides.
2007 Elsevier B.V. All rights reserved.
Keywords: Simmondsia chinensis; Glucosides; Simmondsin; Simmondsin 2 -ferulate; Insecticidal activity; Antifeedant activity; Antifungal activity
1. Introduction
Simmondsia chinensis (Link) Schneider is a semiarid evergreen shrub. It grows wild in the desert
south-western United States and north-western Mexico. However, the plant is cultivated in some of the
Middle East and Latin American countries (Borlaug
et al., 1985; Bellirou et al., 2005). Jojoba seeds contain about 5060% of a unique wax ester oil which is
composed mainly of straight chain monoesters in the
range of C40 C44 (Ellinger et al., 1973). Jojoba oil has
good markets in the cosmetics and lubricant industries
(Cokelaere et al., 1992), and recently, it has been reported
Corresponding author. Tel.: +20 3 584 7175; fax: +20 3 592 0067.
E-mail address: samir1969us@yahoo.com (S.A.M. Abdelgaleil).
0926-6690/$ see front matter 2007 Elsevier B.V. All rights reserved.
doi:10.1016/j.indcrop.2007.04.005
346
Fig. 1. Chemical structure of glucosides isolated from the seeds of Simmondsia chinensis.
H-6 a), 3.81 (1H, brd, J = 12.2 Hz, H-6 b), 3.90 (1H, q,
J = 3.7 Hz, H-5), 4.37 (1H, d, J = 8.4 Hz, H1 ), 4.71 (1H,
brd, J = 8.4, H-3), 4.86 (1H, t, J = 3.9, H-1) and 5.69 (1H,
s, H-7).
Simmondsin 2 -ferulate: 1 H NMR 1.47 (1H, d,
J = 12.3 Hz, H-6a), 2.39 (1H, d, J = 14.5 Hz, H-6b) 3.00
(1H, dd, 10.0 and 3.3 Hz, H-4), 3.23 (3H, s, 5-OCH3 ),
3.35 (1H, m H-5 ), 3.37 (3H, s, 4-OCH3 ), 3.45 (1H, dd,
J = 19.1 and 9.9, H-4 ), 3.60 (1H, m, H-3 ), 3.72 (2H, m,
H-6 ), 3.84 (3H, s, O-CH3 ), 3.84 (1H, H-1 ), 4.60 (1H,
d, J = 7.7 Hz, H-3), 4.73 (1H, dd, J = 21.4 and 11.5 Hz,
H-2 ), 4.86 (1H, t, J = 9.2 Hz, H-1), 5.71 (1H, s, H-7),
6.34 (1H, d, J = 15.3, H-2 ), 6.80 (1H, d, J = 5.1, H-8 ),
7.04 (1H, d, J = 8.4 Hz, H-9 ), 7.63 (1H, d, J = 15.3 Hz,
H-3 ), 7.76 (1H, s, H-5 ).
2.5. Insecticidal assay
The third instar larvae of S. littoralis were used to
assess the larvicidal activity of the isolated glucosides,
simmondsin and simmondsin 2 -ferulate. A series of
concentrations of the isolated compounds and a reference insecticide, chlorpyrifos were prepared in acetone.
One microliter of test solution was applied on the dorsum of larvae by a microapplicator. Three replicates of
10 larvae in each one were maintained for each dose and
control treatment. The treated larvae were then transferred to glass cups and supplied with fresh castor bean
leaves. The percentages of mortality were recorded after
24 h of treatment and corrected if necessary by Abbotts
formula (Abbott, 1925). The lethal dose causing 50%
mortality (LD50 ) expressed as g/larva was calculated
using probit analysis (Finney, 1971).
2.6. Antifeedant assay
The antifeeding activity of the isolated glucosides
was tested against the third-instar larvae of the cotton
leafworm, S. littoralis, by using a non-choice leaf disc
method as described by Kubo and Nakanishi (1977).
Stock solutions in acetone of test compounds were prepared. A series of concentrations of each compound were
prepared by dilution with distilled water then Triton-X
100 was added at a constant concentration of 0.05%.
Leaf discs (15 mm diameter) of castor bean plant were
immersed in test solutions for 10 s and left to dry. Five
treated discs were transferred into a glass cup with 10
third instar larvae. Three replicates of each concentration and control were arranged. Control discs were
immersed in a solution containing water, acetone and
Triton-X 100. The larvae were left to feed for 24 h at 26
C 2 and 70 5 RH. The eaten areas in the control and
347
348
Table 1
Insecticidal activity of isolated glucosides against the third instar larvae of Spodoptera littoralis using topical application assay
Compound
Simmondsin
Simmondsin 2 ferulate
Chlorpyrifos
a
b
c
LD50 a (g/larva)
1.49
2.58
0.12
Upper
0.92
1.71
0.10
2.31
3.84
0.14
Slope S.E.b
Intercept S.E.c
d.f.
0.63 0.06
0.69 0.07
1.55 0.11
0.11 0.07
0.29 0.07
1.43 0.11
17.4
12.5
19.7
4
4
5
was observed at 1000 g/ml where simmondsin and simmondsin 2 -ferulate caused antifeedant percentages of
92.12 and 90.0, respectively.
10
50
100
500
1000
38.1
46.2
63.4
78.9
92.1
0.3 a
0.5 b
0.3 c
0.7 d
0.4 e
Simmondsin 2 ferulate
32.3
44.2
60.9
76.9
90.0
0.7 a
0.6 b
0.7 c
0.4 d
0.8 e
a Antifeedant index percentages within a column followed by different letters are significantly different at P = 0.05 by StudentNewman
Keuls test.
349
Table 3
Fungicidal activity of isolated glucosides against plant pathogenic fungi using radial growth inhibition assay
Fungus
EC50 a (mg/l)
Upper
Slope S.E.b
Intercept S.E.c
d.f.
Simmondsin
Rhizoctonia solani
Pythium debaryanum
Botrytis fabae
Fusarium oxysporum
129.3
146.8
116.5
223.3
94.2
108.7
95.5
154.1
177.4
198.4
161.9
325.1
0.86
0.91
0.82
0.75
0.09
0.09
0.09
0.09
1.81
1.97
1.69
1.76
0.19
0.20
0.19
0.20
1.8
4.6
2.1
0.8
4
4
4
4
Simmondsin 2 ferulate
Rhizoctonia solani
Pythium debaryanum
Botrytis fabae
Fusarium oxysporum
146.1
153.9
145.9
293.2
105.8
112.3
103.4
202.0
201.9
211.3
206.1
428.1
0.84
0.97
0.78
0.79
0.09
0.09
0.09
0.09
1.81
1.98
1.69
1.95
0.20
0.20
0.19
0.20
1.0
3.6
1.9
1.4
4
4
4
4
Tolcofos-methyl
Rhizoctonia solani
Pythium debaryanum
Botrytis fabae
Fusarium oxysporum
5.7
8.9
21.9
51.3
3.6
5.5
12.3
26.2
9.1
14.7
41.5
112.7
0.59
0.57
0.49
0.48
0.06
0.06
0.06
0.06
0.45
0.53
0.66
0.81
0.08
0.08
0.08
0.08
9.8
9.3
5.9
1.8
4
4
4
4
a
b
c
350
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