Industrial Crops and Products 26 (2007) 345350

Insecticidal, antifeedant and antifungal activities of two glucosides

isolated from the seeds of Simmondsia chinensis
Moustafa A. Abbassy a , Samir A.M. Abdelgaleil b, ,
Abdel-Salam H. Belal a , Mona A.A. Abdel Rasoul a
a

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

that the jojoba seeds possess anti-inflammatory activity

(Habashy et al., 2005).
After oil extraction of jojoba seeds, a protein rich
residue remains, known as defatted jojoba meal. The
meal contains 2032% of protein, consisting mainly of
albumins (79%) and globulins (21%) (Shrestha et al.,
2002). This meal also contains approximately 15% of
a group of glucosides, known as simmondsins (Ellinger
et al., 1973; Van Boven et al., 2000). Eight glucoside
compounds (simmondsin and seven simmondsin derivatives) have been isolated and identified form jojoba seeds
(Bellirou et al., 2005). Among these the methylated
compounds simmondsin and simmondsin 2 -ferulate
exhibited food-intake inhibition in rodents and chickens.
In our search of the literature we have found no
studies on the bioactivity of extracts and glucosides
isolated from jojoba against agricultural pests. In addi-

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M.A. Abbassy et al. / Industrial Crops and Products 26 (2007) 345350

tion, the chloroform extract of S. chinensis seeds

displayed a higher pesticidal activity than petroleum
ether, diethyl ether and ethanol extracts in a preliminary
test. Therefore, this extract was selected to test for active
compounds responsible for this biological activity. The
present work was designed to isolate the active glucosides from the chloroform extract of jojoba seeds of this
plant and to evaluate their insecticidal and antifeedant
activities against cotton leafworm, Spodoptera littoralis
Boisduval (Lepidoptera: Noctuidae) as well as their antifungal activity against four plant pathogenic fungi.

of Agriculture, Alexandria University. The colony was

reared under laboratory conditions on caster bean, Ricinus communis L., leaves at 26 C 2 and 70 5 RH
(Eldefrawi et al., 1964). Four plant pathogenic fungi,
Pythium debarianum (Edson) Fitzp, Fusarium oxysporum Schi, Rhizocotonia solani Kuhn and Botrytis fabae
Pers, were used. The fungi were maintained during the
course of the experiments on Czapek-Dox Agar (CDA)
at 25 C.
2.4. Extraction and isolation of active glycosides
from the seed of S. chinensis

2. Materials and methods

2.1. Plant material
Seeds of S. chinensis (Link) Schneider were collected
from the Al-Bostan Region, Behera Governorate, Egypt
in September, 2004. The plant material was identified by
Prof. Dr. Fath Allah Zaitoon of Faculty of Agriculture
(El-Shatby), Alexandria University, where voucher No.
06/6 is deposited.
2.2. Instruments
UV spectra were measured with HEIOS UV-VL
Spectrophotometer V4.60 in methanol. IR spectra were
performed with Perkin Elmer 1430 Ratio Recording
Infrared Spectrometer in KBr disks. 1 H and 13 C NMR
spectra were recorded at 500 MHz and 125 MHz, respectively, on a JEOL JNM ECD 500 Spectrometer in
CD3 OD.
2.3. Test organisms
A susceptible cotton leafworm, S. littoralis, strain
was obtained from the Bioassay Laboratory, Faculty

Dried and powdered seeds of S. chinensis (1 kg) were

exhaustively extracted with petroleum ether (6080 C),
diethyl ether, chloroform and ethanol (3 L of each solvent), respectively, using a Soxhlet apparatus for 4 h.
After evaporation of the solvents under reduced pressure,
the chloroform extract (45.4 g) was subjected to silica gel
(1 kg, 70230 mesh, Merck) column chromatography,
eluted by a chloroform/methanol solvent system; starting with chloroform then 10% methanol/chloroform then
20% methanol/chloroform and finally with methanol.
Thirty fractions of 200 ml were collected and pooled to
two main fractions based on their TLC profiles. Fraction
1 (3.4 g) was further purified by silica gel column chromatography using 10% chloroform/methanol solvent
system to give 2.1 g of simmondsin 2 -ferulate (Fig. 1).
Similar purification of the second fraction (7.3 g) followed by recrystallization from acetone/chloroform
(1:4) gave 5.4 g pure prisms of simmondsin.
Simmondsin: 1 H NMR 1.68 (1H, dt, J = 14.5 and
3.9Hz, H-6a), 2.48 (1H, dt, J = 15.3 and 3.9 Hz, H-6b)
3.13 (1H, dd, 9.2 and 3.1 Hz H-2 ), 3.22 (1H, m H-4),
3.29 (1H, t, J = 8.4 Hz, H-5 ), 3.32 (1H, t, J = 9.2, H4 ), 3.36 (1H, t, J = 8.6 Hz, H-3 ), 3.43 (3H, s, 5-OCH3 ),
3.45 (3H, s, 4-OCH3 ), 3.64 (1H, dd, J = 12.3 and 5.4 Hz,

Fig. 1. Chemical structure of glucosides isolated from the seeds of Simmondsia chinensis.

M.A. Abbassy et al. / Industrial Crops and Products 26 (2007) 345350

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

treated discs were measured with a planimeter (Dethier,

1947). The percentage of feeding inhibition was determined after 24 h by the formula of Abivardi and Benz
(1984): antifeeding index (AFI) = 100(C T/C), where
C is the eaten area of leaf discs in the control and T is
the eaten area of leaf discs in the treatment. The data
were subjected to analysis of variance and means were
compared for significance by a StudentNewmanKeuls
test at the probability of 0.05 (Cohort Software Inc.,
1985).
2.7. Antifungal assay
The antifungal activity of the isolated glucosides
was tested using the radial growth inhibition technique
(Zambonelli et al., 1996). Appropriate volumes of the
stock solutions of the tested glucosides in dimethyl sulfoxide (DMSO) were added to molten nutrient agar
medium (Czapek-Dox Agar; CDA) to obtain a range of
concentrations (10, 50, 100, 250, 500 and 1000 g/ml)
before pouring into the Petri dishes (9.0 cm in diameter)
at 4045 C. Each concentration was tested in triplicate.
Parallel controls were maintained with DMSO mixed
with CDA medium. The discs of mycelial felt (0.5 cm
diameter) of the plant pathogenic fungi, taken from
8-day-old cultures on CDA plates, were transferred aseptically to the centre of Petri dishes. Tolcofos-methyl
was used as a reference fungicide. The treatments
were incubated at 25 C in the dark. Colony growth
diameter was measured after the fungal growth in the
control treatments had completely covered the Petri
dishes. Percentage of mycelial growth inhibition was
calculated from the formula: Mycelial growth inhibition = [(DC DT)/DC] 100 (Pandey et al., 1982),
where DC and DT are average diameters of the fungal colonies for control and treatments, respectively.
The concentration of the compound inhibiting fungal
mycelial growth by 50% (EC50 ) was calculated using
probit analysis (Finney, 1971).
3. Results
3.1. Isolation and structure elucidation of
glucosides from the chloroformic extract of S.
chinensis
The chloroform extract was fractionated on silica gel
column chromatography and the most active fractions
were further purified on a silica gel column followed by
recrystallization to give two glucosides, simmondsin and
simmondisn 2 -ferulate (Fig. 1). The chemical structures
of simmondsin and simmondsin 2 -ferulate were eluci-

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M.A. Abbassy et al. / Industrial Crops and Products 26 (2007) 345350

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

95% confidence limits (g/larva)

Lower

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

Dose causing 50% mortality after 24 h.

Slope of dose-concentration mortality regression line.
Intercept of regression line.

dated by using spectroscopic methods, including UV, IR,

1 H NMR,13 C NMR and MS.

was observed at 1000 g/ml where simmondsin and simmondsin 2 -ferulate caused antifeedant percentages of
92.12 and 90.0, respectively.

3.2. Insecticidal effect of the isolated glucosides

3.4. Antifungal activity of the isolated glucosides
The insecticidal activity of isolated compounds,
simmondsin and simmondsin 2 -ferulate was evaluated by topical application assay on the third instar
larvae of S. littoralis. Table 1 presents the LD50 values (g/larva) of the two compounds and a reference
insecticide, chlorpyrifos. Both compounds revealed a
pronounced insecticidal activity but were less active
than chlorpyrifos. Simmondsin (LD50 = 1.49 g/larva)
showed higher insecticidal activity than simmondsin 2 ferulate (LD50 = 2.58 g/larva).
3.3. Antifeedant efcacy of isolated glucosides
Antifeedant percentages of the two compounds
against the third instar larvae of S. littoralis are shown
in Table 2. The antifeedant activity for both compounds
was concentration-dependent. The isolated compounds
exhibited strong antifeedant activity even at a low concentration of 10 g/ml with antifeedant percentages of
38.05 and 32.30 for simmondsin and simmondsin 2 ferulate, respectively. The highest antifeedant activity
Table 2
Antifeedant activity of isolated glucosides against the third instar larvae
of S. littoralis using non-choice leaf disc assay
Concentration (g/ml)

Antifeedant index (AFI % S.E.M.)a

Simmondsin

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.

In antifungal assay, the isolated glucosides showed

moderate activity against the four fungi tested; P. debarianum, F. oxysporum, R. solani and B. fabae as shown
in Table 3. Simmondsin revealed higher inhibition than
simmondsin 2 -ferulate against all of the test fungi. B.
fabae was the most sensitive fungus to simmondsin,
while F. oxysporum was the less sensitive one. Simmondsin 2 -ferulate showed more inhibitory activity to
R. solani and B. fabae than P. debarianum and F. oxysporum. The isolated glucosides were less active than a
reference fungicide, tolcofos-methyl.
4. Discussion
Extensive studies of spectroscopic data of the isolated
glucosides from the seed of S. chinensis allowed us to
confirm the two isolated compounds as simmondsin and
simmondsin 2 -ferulate. The two glucosides have been
isolated before from jojoba seed (Van Boven et al., 1994,
1995). Comparing the bioactivities of these compounds
with that of the chloroform extract of the seeds revealed
that the isolated glucosides were more active than the
crude extract against all of the tested pests. This finding suggests that the isolated glucosides are among the
active compounds responsible to the bioactivity of this
plant. It has been reported that simmondsin was the compound responsible for reduction in food intake of jojoba
meal (Booth et al., 1974). In addition, Cokelaere et al.
(1992) and Flo et al. (1997) stated that simmondsin and
simmondsin 2 -ferulate exhibited food-intake inhibitory
activity on experimental animals.
The results of insecticidal activity of the isolated
glucosides against S. littoralis indicated that both compounds had a remarkably toxic effect. In addition,

M.A. Abbassy et al. / Industrial Crops and Products 26 (2007) 345350

349

Table 3
Fungicidal activity of isolated glucosides against plant pathogenic fungi using radial growth inhibition assay
Fungus

EC50 a (mg/l)

95% confidence limits (mg/l)

Lower

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

Concentration causing 50% fungal growth inhibition.

Slope of log-concentration inhibition regression line.
Intercept of regression line.

the isolated compounds showed promising antifeedant

activity. This activity was stronger than that of limonoids
isolated from Khaya senegalensis (Abdelgaleil and
Nakatani, 2003), Khaya ivorensis, Chukrasia tabularis and Swietenia mahogani tested against the same
insect (Abdelgaleil and El-Aswad, 2005) but comparable with that of neo-clerodane diterpenoids isolated from
Salvia spp. However some of these neo-clerodane diterpenoids were more active than the isolated compounds
(Simmonds et al., 1996). Moreover, the isolated glucosides showed moderate antifungal activity against the
four tested plant pathogenic fungi. The isolated compounds were more active than monoterpenes; camphor
(EC50 = 488 mg/l), cinnamaldehyde (EC50 = 169 mg/l)
and borneol (EC50 = 447 mg/l) against R. solani. However, they were less active than monoterpenes; thymol
(EC50 = 4 mg/l), carvacrol (EC50 = 41 mg/l) and carveol
(EC50 = 92 mg/l) (El-Zemity and Ahmed, 2005). Furthermore, the isolated glucosides were more potent than
sesquiterpenes (costunolide and parthenolide) isolated
from Magnolia grandiora against F. oxysporum but
less potent than them against R. solani (Ahmed and
Abdelgaleil, 2005).
The present results indicate that the isolated glucosides; simmondsin and simmondsin 2 -ferulate have
remarkable insecticidal and antifeedant activities against
S. littoralis. Moreover, they have moderate antifungal
activity against the four tested plant pathogenic fungi. It
is concluded from these studies that the isolated glu-

cosides might be considered as key compounds for

developing safe alternative plant protection agents. Further investigations on pesticidal and toxicological effects
of these glucosides are highly recommended.
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