FLAVOUR AND FRAGRANCE JOURNAL, VOL.

8,1-4(1993)

Aromatic Plants of Tropical Central Africa. Part X* Chemical

Composition of the Essential Oils of Ageratum houstonianum
Mill. and Ageratum conyzoides L. from Cameroon
C. Menut and G. Lamatyt
hboratoire & Chimie Organique Physque, Universiti & Montpellier 11, Sciences et Techniques du h g u e a b c , 34095 Montpellier,
Ciakx S, France

P.H. Amvam Zollo and J. R. Koiate

Luboratoire de Biochimie, Faculth des Sciences, B.P. 812, Y a o d , Cameroun

J. M. Bemibre
Luboratoire de Phytochimie, ENSCM, 34053 Montpellier, Ckdex I , France

The essential oils isolated from the leaves of Ageratum houstonianum Mill. and Ageratum conyzoides L. by
hydrodistillation were analysed by GLC and GC-MS. The essential oil of A . houstonianum contained 7-methoxy-2.2-
dimethylchromene (precocene I) and ageratochromene (precocene 11) in almost similar amounts (32% and 24%
respectively) whereas that of A. conyzoides was rich in precocene I (81%)and poor in precocene I1 (0.2%).Our findings
are compared with those of the literature.
KEY WORDS Ageratum houstonianum Mill. Ageratum conyzoides L. Astcraceae Essential oil
Ageratochromene

INTRODUCTION used in the treatment of parasites, rheumatism,

Ageratum houstonianum Mill. (Asteraceae) is an
annual herbaceous violaceous plant with involucral
bracts and white or bluish-purple florets. Leaves
are opposite, simple, serrate, pilous, 5-10 cm long,
3-6cm wide.’ It grows on the skirts of tracks in
forest zone; in Cameroon the plant is utilized for
soil protection and as food for cattle.3
Ageratum conyzoides L. is a faintly aromatic erect
or procumbent annual herb, 0.4-1 m high with
mauve florets in heads about 0.7 cm long. Leaves
are supple, opposite, oval, 5-8 cm long, 3-4 cm
wide. It is widespread throughout the tropics and
subtropics where it grows wild near habitations
and on fallow land.’.’
The plant is used in folk medicine as a remedy for
numerous disease^.'^ In Cameroon, the leaves are
*Part IX sce Reference 1.
tSenior author.
0882-S734/93/010001-0$07.00
0 1993 by John Wiley & Sons, Ltd
headaches and
This species has been already studied several
times; the numerous chemical investigations of the
essential oil constituents of A. conyzoides from
different originse” indicate the presence of benzo-
pyran derivatives as typical components. The three
most recent papers dealing with the essential oils of
A. conyzoides show that fl-caryophyllene, agera-
tochromene (6,7dimethoxy-2,2dimethylchromene,
precocene 11) and 7-methoxy-2,2-dimethylchro-
mene (precocene I) are the main constituents of the
oils; however, the amounts of each compound may
be very different, depending upon the geographic
origin of the sample and the part of the plant
extracted.
On the other hand, A. houstonianum has been
mainly examined for its non-volatile constituents:
flavonoids,”” triterpenoids and steroids
constituent^^^ or benzofuran The
only work on the volatile components of this
Received 17 June 1992
Accepted 11 August 1992
2 C. MENUT ET AL.

species deals with the biosynthesis of precocene I
and I1 in the different parts of the plant2’ (studied
by HPLC analysis of the acetone extracts of differ-
ent parts of the plant material).
To our knowledge, no earlier analysis of the
essential oil of A. houstonianum has been carried
out.
This paper describes a study of the essential oils
of the leaves of A. houstonianum and A. conyzoides
collected in Cameroon.
EXPERIMENTAL
Collection of Plant Material and Isolation of
Essential Oil
A. houstonianum and A. conyzoides non-flower-
ing plants were collected respectively in December
1990 in the Bafoussam region (western province of
Cameroon) and in November 1987 in the Yaounde
region.
The botanical identification of the material col-
lected was carried out by Dr Amougou Akoa
(Laboratoire de Botanique, Universitt de
Yaoundt). Voucher specimens are kept at National
Herbarium of Yaounde.
Samples of 300g of the air-dried leaves of the
individual plants (1200 g for each species) were
subjected to hydrodistillation for 6 hours using a
Clevenger-type apparatus. The oils obtained were
dried over anhydrous Na2S0,. No significant dif-
ference was observed by rapid GC analysis between
the several fractions of distillation which were
mixed and analysed more accurately.

Table 1. Percentage composition of essential oils of Ageratum houstonianum Mill.

and A. conyzoides L. leaves from Cameroon

No. Peak compound A. houston-

ianwn A. conyroides Kovats index
(sample A) (sample B) on OV-101

1 a-Pinene <0.1 - 931

2 Camphene 0.7 - 956
3 8-Pinene <0.1 - 968
4 Myrcene 0.7 - 975
5 a-Phellandrene <0.1 - 1000
-
6

7
ILimonene
1,8-Cineole
Linalol
co.1
t0.1
<0.1
-
-
1025
1025
1083
8 Thymol 0.9 0.3 1264
9 Carvacrol <0.1 <0.1 1273
10 Thymyl acetate <0.1 <0.1 1343
11 Carvacryl acetate <0.1 <0.1 1349
12 a-Cubebene co.1 - 1355
13 8-Bourbonene <0.1 - 1362
14 a-Copaene <O.l - 1384
15 8-Elemene 0.9 0.5 1385
16 8-Caryophyllene 27.5 10.5 1420
17 (E>B-Farnesene 2.0 0.3 1435
a-Humulene 0.9 0.9 1435
18 7-Methoxy-2,2-dimethyl
chromene (precocene I) 32.0 81.0 1440
19 Germacrene-D -

20
I(E)-a-Farnesene
8-Selinene
-
t0.1
0.9
0.3
<0.1
1468
1468
1477
21 a-Selinene <O.l <0.1 1484
22 8-Sesquiphellandrene 4.5 1.9 1513
23 (E)-Nerolidol <0.1 0.2 1524
24 Spathulenol t0.1 - 1565
25 Caryophyllene epoxide 1.4 0.2 1569
26 Demethoxyencecalin <0.1 0.1 1616
27 Ageratcchromene
(precocene 11) 24.0 0.2 1619
28 6-Vinyl-7-methoxy-2,2-
dimethylchromene <0.1 0.2 1645
 ESSENTIAL OILS OF AGERATUM SPP.
Table 2. Comparative compositional data on characteristicconstituents of Ageratum leaf oils (%)
A. conyzoides L.
India9 Nigeria15 Vietnam16
Yields (%) 0.2 0.06 0.16-0.26
p-Caryophyllene 7 1.9 16.5
Precocene I 10 82.2 29.0
Precocene I1 75.4 0.7 31.1
Identification of the Oil Components
GC analyses were performed on two fused-silica
capillary columns (25 m x 0.25 mm i.d.), coated
with OV-101 or Carbowax 20 M; the oven temper-
ature was programmed from 50°C to 200°C at
5 "C/min.
GC-MS analyses were carried out on a Hewlett-
Packard capillary GC-quadrupole MS system
(model 5970) fitted with a 25 m x 0.23 mm i.d.
fused-silica column coated with DB-1 and using the
same gas-chromatographic parameters. The oil
components were identified by comparison with
those of reference compound^.'^^^*-^^
RESULTS AND DISCUSSION
The essential oils were obtained in 1.0% and 0.7%
(w/w) mean yields respectively for A. houstonianum
(sample A) and A. conyzoides (sample B). Both are
pale yellow liquids with very strong long-lasting
odours.
The results of the chromatographic analyses of
these oils are presented in Table 1. The components
we have identified are arranged according to their
order of elution on OV-101 and their linear reten-
tion indices are indicated.
There is a great qualitative resemblance between
the two oils; both contain 8-caryophyllene and the
same benzopyran derivatives as main constituents
but the amount of each of them is quite different.
The A. conyzoides essential oil contains mainly
the precocene I (81%), 10.5% of 8-caryophyllene
and only a trace (0.2%) of precocene 11; on the
contrary the oil of A. houstonianurn contains similar
amounts of precocene I1 (24%) and precocene I
(32%) along with 8-caryophyllene (27.5%).
We have gathered together, for comparison pur-
3
A . houstonianum
Fiji" Cameroon Cameroon
Suva Nadi
0.13 0.21 0.7 1.o
21.9 16.0 10.5 27.5
37.5 59.3 81.0 32.0
21.3 0.3 0.2 24.0
pose, the literature data on the analyses performed
on A. conyzoides oils from different origins (Table 2).
The most salient feature which stems from Table
2 is that there is a great variability in the amounts
of precocene I and I1 found in the oils of A.
conyzoides: that from India is rich in precocene 11;
those from Nigeria and Cameroon in precocene I;
those from Vietnam and Fiji (Suva) containing
roughly comparable amounts of both compounds.
We can remark that the A. houstonianum oil from
Cameroon belong to the third category of oil. It is
worth noting that the yield of essential oil is much
higher for the Cameroonian species than for those
of other countries. This relatively high oil content
of the Cameroonian plants can perhaps make them
an interesting natural source of precocene I and I1
which have been found to possess insect-control
properties as anti-juvenile hormones.
Finally, although detected in low concentrations,
thymol, carvacrol and their acetylated derivatives,
have been identified for the first time in the genus
Ageratum.
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