Fitoterapia 73 (2002) 520522

Short report

Molluscicidal and radical scavenging activity of

quinones from the root bark of Caryopteris x
clandonensis
S. Hannedouche*, J.P. Souchard, I. Jacquemond-Collet,
C. Moulis
Laboratoire Pharmacophores Redox, Phytochimie et Radiobiologie,

Faculte des Sciences Pharmaceutiques, 35 Chemin des Marachers,

F-31062 Toulouse Cedex 04,
France
Received 13 September 2001; accepted 18 July 2002

Abstract
In the search for new molluscicidal natural products, the activity of the chloroform extract
of the root barks of Caryopteris x clandonensis was tested. The LC100 was -5 ppm. The
fractionation and purification of the extract afforded 15-deoxyfuerstione, fuerstione and acaryopterone as the main compounds. These compounds were tested against the snail Bulinus
truncatus, an intermediate host snail of a schistosomiasis parasite and showed strong
molluscicidal activity with LC100 -4 ppm. In addition, they were found to have potent radical
scavenging properties on superoxide radical.
2002 Elsevier Science B.V. All rights reserved.
Keywords: Caryopteris x clandonensis; a-Caryopterone; Dehydro-a-lapachone; 15-Deoxyfuerstione;
Fuerstione; Molluscicidal activity; Antioxidant activity

Plant. Caryopteris x clandonensis Simmonds (Lamiaceae), commonly known as

bluebeard, was purchased from a commercial supplier in Toulouse in September
1997. A voucher specimen (CC-9709) was deposited at the Pharmacognosy
Department, Faculty of Pharmaceutical Sciences, Toulouse, France.
*Corresponding author. Fax: q33-5-61554330.
E-mail address: shannedouche@hotmail.com (S. Hannedouche).
0367-326X/02/$ - see front matter 2002 Elsevier Science B.V. All rights reserved.
PII: S 0 3 6 7 - 3 2 6 X 0 2 . 0 0 1 6 3 - 6

S. Hannedouche et al. / Fitoterapia 73 (2002) 520522

521

Uses in traditional medicine. No report for this species. However, Caryopteris

incana (Thumb.) Miq., one of the parent of the studied hybrid, has been used in
China as a folk medicine for the relief of colds, coughs and rheumatic pains w1x.
Previously isolated constituents. Iridoids w2,3x and quinone w4x.
New isolated constituents. a-Caryopterone (1) w4x (0.087%), dehydro-a-lapachone
(2) w5x (0.003%), 15-deoxyfuerstione (3) w6x (0.33%) and fuerstione (4) w7x
(0.013%). The three last compounds are newly isolated in the genus Caryopteris.

Tested material. Chloroform extract, a-caryopterone (1), dehydro-a-lapachone (2),

15-deoxyfuerstione (3) and fuerstione (4).
Studied activities. Molluscicidal, according to the protocols of the World Health
Organization w8x. Niclosamide was used as a reference. Radical scavenging activity
on superoxide anion was determined using Electron Spin Resonance (ESR) and
spin trapping technique. The superoxide dependent ESR signals decrease when the
antioxidant compounds are incubated with the acetaldehydeyxanthine oxidase
superoxide generating system w9x. L-ascorbic acid and a-tocopherol were used as
references. All compounds were tested at 4=10y4 M.
Used organisms. Tropical water snail Bulinus truncatus, intermediate host of the
schistosomiasis parasite Schistosoma haematobium.
Results. Molluscicidal activity is reported in Table 1. The crude chloroform extract
displayed significant molluscicidal activity with 100% of the snails killed at

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S. Hannedouche et al. / Fitoterapia 73 (2002) 520522

Table 1
Molluscicidal and radical scavenging activity
Compound

Molluscicidal activity
LD100 (ppm)

Radical scavenging activity

% inhibition ESR signal

CHCl3 extract
a-caryopterone (1)
dehydro-a-lapachone (2)
15-deoxyfuerstione (3)
fuerstione (4)
a-tocopherol
L-ascorbic acid

-5
12
nt
34
34
nt
nt

nt
47
1
28
nt
52
100

nt: non-tested.

concentrations of 5 ppm after 24 h. a-caryopterone promoted a mortality of 100%

at 2 ppm, while the two diterpenes (15-Deoxyfuerstione and Fuerstione) were
almost 2 times less active with 100% of mortality at 4 ppm.
Radical scavenging activity is also reported in Table 1.
Conclusions. The results are suggestive of a strong molluscicidal activity against
the adult snail, and are in good agreement with WHO recommendations with
LD100-20 ppm w10x. In the search for molluscicidal agents, these preliminary
results are interesting and further studies have to be undertaken.
Concerning the superoxide scavenging activity, the pattern of inhibitory effect of
a-caryopterone on the formation of the ESR adduct was similar to that of atocopherol. The scavenging effect of 15-deoxyfuerstione on the superoxide anion
was almost half of a-tocopherol, and dehydro-a-lapachone was not able to scavenge
the radical. Thus, the presence of a phenolic hydroxyl group in the potent
antioxidative compounds may be important in the observed radical scavenging
activity. a-Caryopterone was more efficient than 15-deoxyfuerstione. Mesomeric
forms, which stabilize the quinone radical, could explain the best activity of acaryopterone.
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