Sesquiterpene lactone glycosides, eudesmanolides, and other constituents from Carpesium macrocephalum

Article abstract of DOI:10.1055/s-2002-32899

Two new sesquiterpene lactone glycosides and two new eudesmanolides, along with twelve known compounds were isolated from seeds of Carpesium macrocephalum. The structures of these new compounds were elucidated as 2α-O-β-D-glucopyranosyl-5α, 11αH-eudesma-4

Full text of DOI:10.1055/s-2002-32899

Sesquiterpene Lactone Glycosides, Eudesmanolides,
and Other Constituents from Carpesium
macrocephalum
Chao Yang1
Yan-Ping Shi2
Zhong-Jian Jia1
Abstract
spectroscopic methods including 2D NMR techniques (1H-1H
COSY, 1H-1H NOESY,HMQC,HMBC) and chemical transforma-
Two new sesquiterpene lactone glycosides and two new eudes- tions. Compounds 1, 6, 8, 9 and 10 exhibited moderate antibac-
manolides,along with twelve known compounds were isolated terial activity,while compound 4 showed appreciable cytotoxic
from seeds of Carpesium macrocephalum. The structures of these activity against cultured SMMC-7721 (human hepatoma cell).
new compounds were elucidated as 2a-O-b-D-glucopyranosyl-
5a,11 aH-eudesma-4(15)-en-12,8b-olide (1),2 a-O-b-D-glucopyr- Key words
anosyl-5aH-eudesma-4(15),11(13)-dien-12,8b-olide (2),2 a-acet- Carpesium macrocephalum ´ Compositae ´ eudesmanolide ´ ses-
oxy-5a-hydroxy-11aH-eudesma-4(15)-en-12,8b-olide (3) and quiterpene lactone glycosides ´ antibacterial activity ´ cytotoxic
2a,5a-dihydroxy-11aH-eudesma-4(15)-en-12,8b-olide (4) by activity
Introduction
The seeds of Carpesium (Compositae) species have been used as
a vermifuge in Chinese traditional medicine. Sesquiterpene lac-
tones have been reported as the most widespread main consti-
tuents in the genus [1],[2],[3],[4],[5],[6],[7],[8],[9].
626
Carpesium macrocephalum Franch. et Savat. has long been used
as a Chinese folk medicine for its hemostatic and antipyretic
Fig. 1
properties [10]. Its chemical constituents have not been pre-
viously investigated. We describe herein the isolation and
structural elucidation of four new compounds (1±4) and
twelve known compounds (5±16) from the seeds of Carpesium
macrocephalum,and the antibacterial activity test of ten com-
pounds (1, 4, 6, 8±14) and cytotoxic activity test of three com-
pounds (1, 4 and 14) (Figs.1 and 2).
Fig. 2
Affiliation
1 Department of Chemistry,National Laboratory of Applied Organic Chemistry,Lanzhou University,Lanzhou,
P.R. China
2 Lanzhou Institute of Chemical Physics,Chinese Academy of Sciences,Lanzhou,P.R. China
Correspondence
Prof. Zhong-Jian Jia ´ Department of Chemistry ´ Lanzhou University ´ Lanzhou,Gansu 730000 ´
Peoples Republic of China ´ E-Mail: Zhengrl@lzu.edu.cn ´ Fax: + 86-0931-8912582
Received October 5,2001 ´ Accepted February 3,2002
Bibliography
Planta Med 2002; 68: 626±630 ´ ꢀ Georg Thieme Verlag Stuttgart ´ New York ´ ISSN 0032-0943

Materials and Methods
Apparatus
extracted with CHCl3. The aqueous layer was neutralized with
NaHCO3 and concentrated under reduced pressure. The residue
on a silica gel column (1 g) was first eluted with acetone,then
Melting points were determined with a Kofler Melting point with anhydrous ethanol to afford a pure sugar (1.8 mg). The su-
apparatus,and not corrected. Optical rotations were taken on gar was confirmed as D-glucose by comparison with the authen-
a JASCO-20C automatic recording spectro-polarimeter. IR spec- tic sample on PC and measuring its optical rotation.
tra were measured on a Nicolet 170SX FT-IR instrument. 1H-
NMR (400 MHz), 13C-NMR (100 MHz) and 2D NMR spectra Sugar of 1: [a]D20: + 48.08 (c 0.12,H 2O).
were recorded on a Bruker AM-400 FT-NMR spectrometer using
TMS as internal standard. HRESI-MS was recorded on a Bruker 2a-(b-D-Glucopyranosyloxy)-5a,11 aH-eudesma-4(15)-en-12,8b-
APEX II,EI-MS on an HP 5988A GC/MS instrument and FAB-MS
on a VG-ZAB-HS mass spectrometer. Silica gel (200±300 mesh) + 17.98 (c 0.56,CH OH). IR (KBr): nmax = 3577,3389 (OH),2936,
olide (1): Colorless needles from CH3OH,m.p. 206±208 8C. [a]D20
:
3
was used for column chromatography,and silica gel GF
for 1778 (g-lactone),1646,1460,1360,1266,1166,1079,971,902
254
TLC were supplied by the Qingdao Marine Chemical Factory in cm±1. HRMS: revealed m/z = 435.1996 [M + Na]+,requires
China.
435.1989. 1H- and 13C-NMR: see Tables 1, 2.
Plant material
2a-(b-D-Glucopyranosyloxy)-5aH-eudesma-4(15),11(13)-dien-
Carpesium macrocephalum Franch. et Savat. were collected in 12,8b-olide (2): Colorless needles from CH3OH,m.p. 176±178 8C.
Tianshui,Gansu province,P. R. China,in September 1998. It was
identified by Prof. Guoliang Zhang,Department of Biology,Lanz-
[a]D25: + 13.08 (c 0.69,CH OH). IR (KBr): nmax = 3574 (OH),3408,
3
2932,1768 ( g-lactone),1650,1600,1454,1349,1170,1081,1039,
hou University. A voucher specimen (NO.9803) was deposited in 964,895,818 cm ±1. HRMS: revealed m/z = 428.2295 [M + NH4]+,
the Institute of Organic Chemistry,Lanzhou University. Seeds
were harvested,then air-dried.
requires 428.2279. 1H- and 13C-NMR: see Tables 1, 2.
2a-Acetoxy-5a-hydroxy-11aH-eudesma-4(15)-en-12,8b-olide (3):
[a]D25: + 77.08 (c 0.44,CHCl 3). IR (KBr): nmax = 3482 (OH),2962,
Extraction and isolation
Air-dried seeds of Carpesium macrocephalum (980 g) were pul- 1756 (g-lactone),1702 (OAc),1376,1265,1174,1020,964,918,
verized and extracted with methanol (3200 ml”4 times,7 days
881 cm±1. HRMS: revealed m/z = 331.1515 [M + Na]+,requires
each time) at room temperature. The extract was evaporated giv- 331.1516. EI-MS: m/z (%) = 248 [M _ AcOH]+ (12),230 [248 _ H2O]+
ing a residue (68 g) which was column (6.0”75 cm) chromato-
graphed over silica gel (200±300 mesh,720 g) with a gradient
of petroleum ether (60±908C)±acetone (1:0,15:1,7.5:1,5:1,
2.5:1 and 1:1). Seven fractions A-G were collected according to
TLC analysis. The eluent of 1:0 (5800 ml) was fraction A,which
was purified by CC on silica gel (150 g) using petroleum ether±
EtOAc (30:1 ® 10:1,680 ml each eluent) to yield 12 (12 mg,
20:1), 11 (21 mg,20:1) and b-sitosterol 15 (10:1). Fraction B
(15:1,4800 ml) gave 8 (125 mg) by repeated recrystallization
from EtOAc,and carabrone 9 (586 mg) was obtained from frac-
tion C (7.5:1,5800 ml). The residue of fraction B,further isolated
over a silica gel column (30 g) with petroleum ether±Et2O (2:1)
yielded 7 (18 mg). The fraction D (7.5:1,5800±15600 ml) was
purified using CC on silica gel (120 g) with petroleum ether±
EtOAc (3:1,1200 ml) to give carabrol 10 (1680 mg) and 3 (14
mg). Scopoletin 13 (22 mg), 6 (58 mg) and 5 (12 mg) were obtain-
ed from fraction E (5:1,6800 ml) after CC on silica gel (120 g)
with CHCl3-CH3OH (60:1,1080 ml) and repeated recrystalliza-
tion. Eluents of 5:1 (6800±11000 ml) and 2.5:1 (8200 ml)
were combined to yield fraction F,which was chromatographed
on a silica gel column (100 g) with CHCl3-CH3OH (30:1 ® 20:1,
590 ml each eluent) to obtain 4 (38 mg,30:1) and 14 (50 mg,
20:1),which were purified by recrystallization (CH 3OH). Frac-
tion G (1:1,15800 ml) afforded 16 by recrystallization. The resi-
due was chromatographed on a silica gel column (160 g) and
eluted with CHCl3-CH3OH (20:1 ® 10:1,500 ml each eluent) to
Table 1 1H-NMR data of 1 and 2 (CD3OD, TMS, d, ppm)a,b
627
No.
1
2
1a
1b
1.25 (br.dd, 12.5, 12.5)
1.99 (ddd, 2, 5, 12.5)
1.24 (t, 12, 12)
2.00 (ddd, 2, 5, 12)
2b
3.87* (m)
3.85* (m)
3a
3b
2.11* (t, 12.5, 12.5)
2.79 (ddd, 2, 5, 12.5)
2.12* (t, 12, 12)
2.79 (ddd, 2, 5, 12)
4
±
±
5a
1.88 (br.d, 12.5)
1.94 (br.d, 13)
6a
6b
1.63* (m)
1.06 (ddd, 12.5, 12.5, 12.5)
1.82 (ddd, 2, 6, 13)
1.26 (ddd, 13, 13, 13)
7a
8a
2.49 (m, 4, 7, 12.5)
4.52 (ddd, 2, 4, 4.5)
3.10 (ddd, 4, 7, 13)
4.56 (ddd, 2, 4, 5)
9a
9b
1.58 (dd, 4.5, 15.5)
2.16* (dd, 2, 15.5)
1.63 (dd, 5, 15.5)
2.20 (br.d, 15.5)
10
±
±
11a
12
2.93 (dq, 7, 7)
±
±
±
13
1.18 (d, 7)
0.78 (s)
6.06, 5.70 (br.s)
0.80 (s)
14
154.89, 4.62 (br.s)
49.8(7b,r.4s.)5
1¢
2¢
3¢
4¢
5¢
6¢
4.34 (d, 8)
4.34 (d, 8)
3.12 (t, 8.2)
3.12 (t, 8.2)
3.34* (t, 8.8)
3.30* (t, 8.8)
3.26* (m, 2, 5.8)
3.34* (t, 8.8)
3.30* (t, 8.8)
3.26* (m, 2, 5.8)
afford 1 (56 mg,10:1),which was recrystallized in CH OH,and 2
3
(7 mg,10:1),which was purified by preparative TLC (GF
CH2Cl2-CH3OH,6:1,180 ml two developments).
,
254
3.85* (dd, 2, 11.8),
3.65(dd, 5.8, 11.8)
3.85* (dd, 2, 11.8),
3.65(dd, 5.8, 11.8)
Acid hydrolysis of 1
a Signal multiplicity and coupling constants (Hz) are in parentheses.
b *Overlapping signals.
Compound 1 (8 mg) dissolved in 2% HCl was heated in a 90 8C
water-bath for 3 hours. After cooling,the reaction mixture was

Table 2 13C-NMR (DEPT) and HMBC data of 1 and 2 (CD3OD, TMS, d, Table 3 1H-NMR data of 3 (CDCl3, TMS, d, ppm) and 4 (CD3OD, TMS,
ppm)
d, ppm)a,b
No
13C (DEPT)
1
HMBC (C/H)
1
13C (DEPT)
2
No
3
4
1a
1b
1.92* (dd, 12, 12)
1.40* (dd, 4.5, 12.5)
1.81* (dd, 12, 12)
1.40* (dd, 5, 12.5)
1
48.5t
76.0 d
45.5 t
148.4 s
/H-3 C-5
22.2 t
41.6 d
79.6 d
42.2 t
35.2 s
42.8 d
182.0 s
9.5q
C-1/H-14
48.4 t
75.8 d
45.5 t
2
C-2/H- 3, 1a, 1¢
C-3/H-15
2b
4.98 (dddd, 4.5, 6, 11, 12)
3.79 (dddd, 5, 5.5, 11.5, 12)
3
3a
3b
2.64* (ddd, 2, 11, 12)
2.58* (ddd, 2, 6, 12)
2.59 (ddd, 2, 11.5, 12)
2.42 (ddd, 2, 5.5, 12)
4
C-4/H-3, 5148.1 s
b, 9b, 15, 14
C-6/H-11
4
5
±
±
546.9 d
46.5 d
28.5t
±
±
6
6a
6b
1.65(dd, 6, 14)
1.56* (dd, 12, 14)
1.69 (dd, 6, 13.8)
1.42* (dd, 12, 13.8)
7
C-7/H-9b, 11, 13
C-8/H-9b
41.5d
8
78.8 d
41.9 t
7a
8a
2.84* (dddd, 5, 6, 7, 12)
4.54 (ddd, 2.4, 4.5, 5)
2.86 (dddd, 5, 6, 7, 12)
4.58 (ddd, 2, 4.6, 5)
9
C-9/H-14
10
11
12
13
14
C-10/H-1a, 5, 9, 14
C-11/H-13
C-12/H-11, 13
C-13/H-11
C-14/H-1a
1t09.5
34.7 s
144.0 s
173.0 s
120.9 t
18.9 q
9a
9b
2.02 (dd, 4.5, 15)
1.83* (dd, 2.4, 15)
2.02 (dd, 4.6, 15)
1.83* (dd, 2, 15)
10
±
±
11a
12
2.97 (dq, 7, 7)
±
2.97 (dq, 7, 7)
±
19.1 q
15109.2 t
/HC-315
13
1.16 (d, 7)
0.90 (s)
1.16 (d, 7)
0.90 (s)
1¢
2¢
3¢
4¢
5¢
6¢
102.9 d
C-1¢/H-2¢
102.9 d
75.1 d
78.1 d
71.6 d
77.9 d
62.8 t
14
75.1 d
78.1 d
71.6 d
77.9 d
62.8 t
±
154.93, 4.80 (br.s)
4.93, 4.80 (br.s)
C-3¢/H-2¢, 5¢
C-4¢/H-3¢
1¢
2¢
±
2.04* (s)
C-5¢/H-4¢
a Signal multiplicity and coupling constants (Hz) are in parentheses.
b *Overlapping signals.
±
(1),233 (15),204 (14),149 (32),123 (38),109 (100),95 (43),94
Table 4 13C NMR (DEPT) and HMBC data of 3 (CDCl3, TMS, d, ppm)
and 4 (CD3OD, TMS, d, ppm)
(28),91 (33),81 (77),69 (42),55 (43),41 (64).
see Tables 3, 4.
1H- and 13C-NMR:
628
No
13C (DEPT)
3
HMBC (C/H)
3
13C (DEPT)
4
2a,5a-Dihydroxy-11aH-eudesma-4(15)-en-12,8b-olide (4): Color-
less crystals from CH3OH,m.p. 108±110 8C. [a]D20: + 68.08 (c 0.74,
CH3OH). IR (KBr): nmax = 3407,3312 (OH),2944,1738 ( g-lactone),
1
40.0 t
69.2 d
37.2 t
C-1/H-3b, 9a, 14
C-2/H-1, 3
45.1 t
67.5d
1656,1186,1042,964,912,878 cm
±1. HRMS: revealed m/z
=
2
289.1413 [M + Na]+,requires 289.1410. EI-MS: m/z (%) = 266
[M]+ (1.6),248 [M _ H2O]+ (9.3),230 [248 _ H2O]+ (2.7),182 (100),
155 (19),137 (16),109 (62),94 (48),91 (28),81 (21),69 (27),55
(32),41 (31). 1H- and 13C-NMR: see Tables 3, 4.
3
C-3/H-1b, 1542.3 t
C-4/H-3, 15
4
147.5s
151.1 s
73.5d
573.3 d
/H-1 C-5
b, 3b, 6a,
9b, 14, 15
6
27.3 t
37.0 d
77.5d
35.4 t
37.1 s
41.0 d
179.1 s
9.4 q
C-6/H-11
28.0 t
38.5d
79.9 d
36.8 t
37.9 s
42.1 d
182.2 s
9.6 q
7
C-7/H-6, 9b, 11, 13
C-8/H-6 a, 9b
C-9/H-1a, 14
C-10/H-6a, 9, 14
C-11/H-6b, 7, 13
C-12/H-11, 13
C-13/H-11
The [a]D25 of known compounds 5±12, 15 and 16 were: + 110.28 (c
0.74,CHCl 3); + 138.08 (c 1.19,CHCl 3); + 122.28 (c 0.50,CHCl 3);
+ 220.38 (c 1.41,CHCl 3); + 104.18 (c 0.61,CHCl 3); + 74.98 (c 1.43,
CHCl3); + 18.68 (c 0.70,CHCl 3); + 0.28 (c 1.43,CHCl 3); ±37.08 (c
8
9
10
11
1.82,CHCl 3); ±46.68 (c 1.12,C H5N).
5
12
13
14
22.3 q
C-14/H-1a, 9
110.2 t
22.9 q
Results and Discussion
15111.9 t
/H-3C-15
1¢
2¢
170.4 s
21.3 q
C-1¢/H-2, 2¢
±
From the methanol extracts of the seeds of Carpesium
macrocephalum two new sesquiterpene lactone glycosides 1
and 2,two new sesquiterpene lactones 3 and 4,together with
twelve known compounds: 11a,13-dihydroivalin 5 [11],ivalin
6 [11],11 a,13-dihydrotelekin 7 [4],telekin 8 [4],carabrone
[2],carabrol 10 [3],5 a,11aH-eudesma-4(15)-en-12,8b-olide 11 ture,and compounds 15 ± 16 by comparison with authentic
[12],5 aH-eudesma-4(15),11(13)-dien-12,8b-olide 12 [13],sco- samples. Compounds 3±12 are sesquiterpene lactones,charac-
9
(MS, 1H-NMR and 13C-NMR) with reported values in the litera-
poletin 13 [14],34, ¢,5,7-tetrahydroxydihydroflavonol 14 [15], teristic for the genus. Compounds 1 and 2 are sesquiterpene
b-sitosterol 15 and sitogluside 16. The known compounds 5± lactone glycosides,and to our knowledge,previously unreport-
14 were identified by direct comparison of their spectral data ed from the genus Carpesium.

Compound 1 was obtained as colorless needles,with molecular
was confirmed by long-range coupling between H-2 and C-1¢
formula C21H32O8 deduced from HRESI-MS (m/z = 435.1996 [M in compound 3. Finally,the stereochemistry was established
+ Na]+,calc. 435.1989). Its IR spectra showed the presence of a
by H1-H1 NOESY spectra. Clear NOE correlations (shown by ar-
rows in Fig. 3) between H-2b and H-14,H-8 and H-11,H-6 b and
carbonyl group (1778 cm±1),hydroxy groups (3389 cm ±1),double
1
bond (1646 cm±1) and a glycosidic linkage (1079 cm±1). The H- H-13,H-14,as well as H-15 and H-6 a,H-6 b indicated that 14-
and 13C-NMR spectra (Tables 1 and 2) of 1 showed the typical sig- CH3,13-CH 3 and H-2 had b-configurations,while H-7,8,11 and
nals for a b-glucopyranosyl,which was confirmed by PC after
hydrolysis of 1. Because the optical rotation of the pure sugar ob- (dH = 0.90 s) and H-15 (dH = 4.93 br.s,4.80 br.s) signals were
tained after hydrolysis of 1 was + 48.08,the sugar was deter- similar to those of the known methyl ester of 5a-hydroxycostic
the hydroxy at C-5 were a-orientated. The shifts of H-14
mined to have the D-configuration. The remaining signals indica- acid,which further confirmed an a-orientation of the 5-hydro-
ted that the aglycone was a sesquiterpene lactone with one ter- xy [16]. Consequently,the two new eudesmanolides were char-
tiary and one secondary methyl,a g-lactone moiety,one terminal
double bond,and two > CH±O± units. Moreover,these signals
acterized as 2a-acetoxy-5a-hydroxy-11aH-eudesma-4(15)-en-
12,8b-olide 3 and 2a,5a-dihydroxy-11aH-eudesma-4(15)-en-
were similar to those of the know eudesmanolide,2 a-hydroxy- 12,8b-olide 4.
5a,11aH-eudesma-4(15)-en-12,8b-olide 1a [11],with the ob-
vious difference in chemical shifts of C-2 from 67.2 ppm in 1a to Antibacterial activity
76.0 ppm in 1,explicable by assuming the additional O-glucoside The compounds 1, 4, 6, 8±14 were tested for their antibacterial
moiety is located at C-2. The doublet for H-1¢ at d = 4.34 (d, J = 8 activities against Bacillus subtilis, Staphylococcus aureus and
Hz) and the resonance for C-1¢ at d = 102.9 indicated that the Escherichia coli using the cup-plate technique in the nutrient
glucosidic bond of 1 had the b-configuration. Furthermore,struc-
tural elucidation was confirmed by 1H-1H COSY,HMQC and
agar media by measuring the inhibition zone in mm. The test
was performed at 200 ppm concentration of each compound in
HMBC spectra. The attachment of glucose to the hydroxy at C-2 a cup of 8 mm diameter. Positive control was choromycetin.
is deduced by the long-range coupling between H-1¢ and C-2. From antibacterial activity data (Table 5) it was found com-
The large coupling of H-2 (J2b 1a
,
= J2b,3a = 12.5 Hz) confirmed pounds 1, 6, 8, 9 and 10 exhibited moderate activity against the
that the 2-hydroxy group was a-oriented. Hence,compound
1
microorganisms.
was identified as 2a-(b-D-glucopyranosyloxy)-5a,11aH-eudes-
ma-4(15)-en-12,8b-olide.
Cytotoxic activity
The compounds 1, 4 and 14 were evaluated for their cytotoxic ac-
The 1H- and 13C-NMR spectra of compound 2 (Tables 1 and 2) tivity against cultured SMMC-7721 (human hepatoma) and HO-
were similar to those of 1 except that the signals of the 11b-or- 8910 (human ovarian carcinoma) cells using the MTT method.
iented methyl g-lactone group (dC = 182.0,C; dH = 2.93 dq, From cytotoxic activity data (Table 6) it was found compound 4
dC = 42.8,CH; dH = 1.18 d, dC = 9.5,CH 3) in 1 had been replaced shows appreciable cytotoxic activity against SMMC-7721.
by the signals of an a-methylene-g-lactone group (d = 173.0,C;
629
d = 144.0,C; dH = 6.06,5.70,brs, dC = 120.9,CH 2). So compound
2 was determined as 2a-(b-D-glucopyranosyloxy)-5aH-eudes-
ma-4(15),11(13)-dien-12,8b-olide.
From HRESI-MS,the molecular formulas of compounds 3 and 4
could be deduced as C17H24O5 and C15H22O4 on the basis of the
quasi-molecular ion peaks at m/z = 331.1516 [M + Na]+ and m/z
= 289.1410 [M + Na]+. Except for the additional signals of an acet-
Fig. 3 Key NOEs observed for compound 4.
yl group [C-1¢ (C, dC = 170.4),C-2 ¢ (CH3, dC = 21.3, dH = 2.04 s)],
the 1H- and 13C-NMR spectral data (Tables 3 and 4) of com-
pounds 3 were very similar to those of 4,which suggested that
compounds 3 and 4 have the same basic carbon skeleton: one
Table 5 Antibacterial activity
tertiary and one secondary methyl,a g-lactone moiety,a termi-
nal double bond,one oxygenated quaternary carbon and two
> CH±O± units.
Compound
B. subtilis
S. aureus
E. coli
1
+
++
+
++
+
Structural elucidation of 3 and 4 was based on 1H- and 13C-NMR
(DEPT) spectra,including 1H-1H COSY,HMQC,and HMBC,which
allowed the full assignment of all carbon and proton resonan-
ces. By 1H-1H COSY experiments,two partial structures:
_CH2_CH(_O_)_CH2_ and _CH2_CH(CH_CH3)_CH(_O_)_CH2_ were re-
4
±
6
++
+
+
+
8
++
+
+
9
++
++
±
+
10
+
+
1
vealed. Together with H-13C long-range correlations (Table 4):
11
+
+
12
+
+
+
C-1/H-9,H-14; C-3/H-15; C-5/H-1,H-3,H-9,H-14,H-15; C-10/H-
6; C-12/H-13,in an HMBC experiment,the whole planar struc-
ture was formed. Comparison of chemical shifts showed that H-
2 (dH = 4.98,in 3) was now downfield (dH = 3.79,in 4),which
implicated that the additional acetyl group is located at the C-
2 hydroxy group. Moreover,this location of the acetyl group
13
+
+
±
14
+
+
+
Chloromycetin
+++
+++
+++
ª±ª: Zone diameter of growth inhibition less than 10 mm, ª+ª equal to 11±13 mm, ª++ª
equal to 14±15mm, ª+++ª more than 15mm.

4 Dong YF,Ding YM. Sesquiterpene lactone from Carpesium abrotanoides.
Acta Botanica Sinica 1988; 30: 71±5
Table 6 Cytotoxic activity
5 Maruyama M. Sesquiterpene lactone from Carpesium divaricatum.
Phytochemistry 1990; 29: 547±50
Compound
SMMC-7721
HO-8910
6 Maruyama M,Watanabe K,Kwakami T, Nozoe S,Ohta T. Ineupatoro-
lides from Carpesium glossophyllum. Planta Medica 1995; 61: 388±9
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terpene lactones from Carpesium nepalense. J. Nat. Prod. 1996; 59:
991±3
1
297.59  1.80
70.28  4.12
> 400
> 400
4
286.28  22.4
> 400
14
8 Kim DK,Baek NI,Choi SU,Lee KR,Zee OP. Four new cytotoxic germa-
cranolides from Carpesium divaricatum. J. Nat. Prod. 1997; 60: 1199±
202
Vinblastine
56.78  4.08
46.57  2.35
Half inhibition concentration IC50 (mg ml±1).
9 Shi YP,Guo W,Jia ZJ. Germacranolides from Carpesium lipskyi. Planta
Medica 1999; 65: 94±6
10
Xue ZW,Yu YQ. ZhongGuo ZhongChaoYao MingJia. People's Health
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407±10
Acknowledgements
11
This work was financially supported by the National Natural Sci-
ence Foundation of China NO. 29972017 and the Foundation of
Ministry of Education of China for Doctoral Program NO.
98073003.
12
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