Wedelia urticaefolia Bl. DC. (Vietnamese name Sơn cúc nhám) has not yet been chemically studied. From leaves of this plant, four compounds were isolated: phytol (1), 3β-O-acetyl-b-amyrin (2), 3-O-tetradecanoylurs-12-ene-16β-ol (3), ent-kaur-16-ene-19-oic acid (4) and from the flowers, three compounds were isolated: b-amyrin (5), stigmasterol (6) and 3-O-tetradecanoylurs-12-ene-16β-ol (3). Their chemical structures were established by spectroscopic analysis

Phi Phung et al, Nguyen Kim

Vietnam Academy of Science and Technology: Journals Online

Journal of Chemistry, Vol. 47 (1), P. 127 - 132 (2009) 
 
SOME DI- AND TRITERPENES OF WEDELIA URTICAEFOLIA (Bl.) 
(ASTERACEAE) 
Received  
NGUYEN THANH HOANG, VO THI LINH CHI, NGUYEN KIM PHI PHUNG 
Department of Chemistry, UNS, National University  Ho Chi Minh City 
 
Abstract 
Wedelia urticaefolia Bl. DC. (Vietnamese name Sơn cúc nhám) has not yet been chemically 
studied. From leaves of this plant, four compounds were isolated: phytol (1), 3β-O-acetyl-β-
amyrin (2), 3-O-tetradecanoylurs-12-ene-16β-ol (3), ent-kaur-16-ene-19-oic acid (4) and from 
the flowers, three compounds were isolated: β-amyrin (5), stigmasterol (6) and 3-O-
tetradecanoylurs-12-ene-16β-ol (3). Their chemical structures were established by spectroscopic 
analysis. 
 
I - INTRODUCTION 
In the continuation of a chemical study on 
the genus Wedelia we now report the isolation 
and characterization of some di- and 
triterpenoids from Wedelia urticaefolia (Bl.) 
DC, the plant grows widely in the urban of Ho 
Chi Minh city. As far as we know no chemical 
research has been reported on this plant.  
A review on the chemical constituents of the 
genus Wedelia showed that this genus contained 
derivatives of ent-kaur-16-ene-19-oic acid, 
ursolic acid and derivatives of oleanolic acid. 
The last one often contained long side chain 
ester at C-3 [1 - 4].  Our research showed that 
Wedelia urticaefolia (Bl.) DC also agrees with 
the phytochemistry of the genus Wedelia so far 
investigated but this plant contained ursane-
type-triterpene with aliphatic long chain ester at 
C-3.
   
 
Part of the plant Wedelia urticaefolia  HO
OC
O
H3C-(H2C)12
OH
OC
O
H3C
CH2
COO H
HO
     β-Amyrin (5)
28
3
2324
12
3029
25 26
27
18
28
3
2324
12
30
29
25 26
27
18
16
1'14'
28
3
2324
12
25 26
27
18
      3-O -Acetyl-β-amyrin (2)
ent-Kaur-16-ene-19-oic acid  (4)
     Phytol (1)
1
19
9
8
15
16
1713
75
4
14
20
18
3-O -Tetradecanoylurs-12-ene-16β -ol (3)
12
 
 127
II - EXPERIMETAL 
1. General  
Melting points were determined on a block 
maquene apparatus and uncorrected. IR (KBr) 
spectra were recorded on a Perkin-Elmer FT-IR 
2000 spectrometer. 1H- and 13C-NMR were 
recorded on Bruker Avance 500 MHz and 125 
MHz, respectively. MS spectra were carried out 
on Agilent-MSD-Trap-SL. 
2. Plant material  
Leaves and flowers of Wedelia urticaefolia 
were separatedly collected in Ho Chi Minh City 
in April 2006. A voucher specimen was 
prepared and deposited by Mr. Phan Duc Binh, 
University of Medicine–Ho Chi Minh City. 
3. Extraction and isolation 
Dried and powdered leave (1100 g) of 
Wedelia urticaefolia was exhaustively extracted 
with ethanol at room temperature to yield the 
ean cethanolic crude extract (79g). The crude 
extract was subjected successively to silica gel 
solid phase extraction to obtain petroleum ether, 
chloroform, ethyl acetate and methanol 
fractions. The chloroform fraction of leave 
(12.5g) was chromatographed on silica gel 
column eluting with increasing amount of ethyl 
acetate in petroleum ether to yield seven 
fractions. Fraction 3 was carried out column 
chromatography with CHCl3-EtOAc (9: 1) to 
yield (1, 22 mg) and (2, 22 mg). Fraction 5 was 
carried out column chromatography with 
CHCl3-EtOAc (8:2) to yield (3) (11 mg). The 
ethyl acetate fraction of leave (7.7 g) was 
chromatographed on silica gel column eluting 
with increasing amount of ethyl acetate in 
chloroform to yield six fractions. Fraction 3 was 
carried out column chromatography with 
EtOAc: methanol (9:1) to yield (4) (8.2 mg).  
Dried and powdered flower (850 g) was 
exhaustively extracted with ethanol at room 
temperature. During the removal under reduced 
pressure the ethanolic solution gave a prepicitate 
(2.4 g). This precipitate was chromatographed 
on silica gel 60H using mixture of petroleum 
ether: ethyl acetate as eluant and eight main 
fractions were collected. Fraction 3 (0.5g, eluted 
by chloroform: ethyl acetate 8:2) was 
rechromatographed on silica gel eluting with the 
same eluant, then preparative TLC and  finally 
recrystallized in appropriate solvent, afforded 
(5, 11.8 mg) and (3, 21.4 mg), respectively.  
Phytol (1): White powder. M.p. 206 - 
209°C. EI-MS: m/z = 284 [M]+. IR (KBr), νmax 
cm-1: 3613 (O-H), 1638 (C=C), 1095 (C-O). 1H-
NMR (CDCl3), δ ppm = 5.40 (1H, t, =CH), 4.16 
(2H, d, J=7.0 Hz, =CH-CH2-OH), 1.9 - 0.8 (-
CH, -CH2, -CH3). 
13C-NMR (CDCl3), δ ppm = 
59.4 (-CH2OH, C1), 123.1 (=CH, C2), 140.33 
(C=, C3), 39.9 (-CH2-, C4), 25.2 (-CH2-, C5), 
36.7 (-CH2-, C6), 32.7 (-CH, C7), 37.4 (-CH2-, 
C8), 24.5 (-CH2-, C9), 37.4   (-CH2-, C10), 32.8 
(-CH, C11), 37.3  (-CH2-, C12), 24.8 (-CH2-, 
C13), 39.4 (-CH2-, C14), 27.9 (-CH, C15), 22.6 
(C16), 22.7 (-CH3, C17), 19.7 (-CH3, C18), 19.7 
(-CH3, C19) and 16.2 (-CH3, C20).   
β-Amyrin acetate (2): White powder. 
IR(KBr), νmax cm-1: 3505 (O-H), 1734 (C=O), 
1248 (C-O). 1H-NMR (CDCl3), δ ppm = 5.18 
(1H, t, =CH, H12), 4.50 (2H, dd, J=3.5, 7.0 Hz, 
H-3), 2.08 (3H, s, H2’), 1.11 (3H, s, H-27), 0.97 
(3H, s, H-26), 0.94 (3H, s, H-26), 0.94 (3H, s, 
H-25), 0.88 (6H, s, H-29; H-30), 0.84 (3H, s, H-
28), 0.72 (3H, s, H-24). 13C-NMR, CDCl3, 
δppm: 38.3 (C1), 26.7 (C2), 81.0 (C3), 37.7 
(C4), 55.3 (C5), 18.3 (C6), 32.6 (C7), 39.9 (C8), 
47.6 (C9), 37.0 (C10), 23.6 (C11), 121.7 (C12), 
145.2 (C13), 41.7 (C14), 27.0 (C15), 26.2 
(C16), 32.5 (C17), 47.3 (C18), 46.8 (C19), 31.1 
(C20), 34.8 (C21), 37.2 (C22), 28.4 (C23), 16.8 
(C24), 15.6 (C25), 16.7 (C26), 25.9 (C27), 28.1 
(C28), 33.3 (C29), 23.6 (C30), 171.02 (C-1’) 
and 21.3 (C-2’).  
3-O-Tetradecanoylurs-12-ene-16β-ol (3): 
Yellow oil. ESI-MS (Positive mode): m/z = 635 
[M+H−H2O]+. (C44H76O3). IR (KBr), νmax cm-1: 
3449 (O-H), 1729 (C=O), 1049 (C-O). The 1H-, 
13C and HMBC-NMR were presented in table 1 
and figure 1. 
ent-Kaur-16-ene-19-oic acid  (4): mp. 
196oC. [α]D = - 91 (C=2, CH2Cl2). IR(KBr) νmax 
cm-1: 3444 (O-H), 1690 (C=O of COOH), 1654 
(C=C), 1261 (C-O). LC-MS-ESI: m/z = 303 
[M+H]+, 256 [M-HCOOH]. 1H-, 13C and 
 128
HMBC-NMR were presented in table 2. 
  
 
Figure 1: Part of HMBC-NMR of (3) 
  
β-Amyrin (5): mp. 178oC. 1H-NMR, CDCl3, 
δppm: 5.18 (1H, t, J = 3.5 Hz, H-12), 3.22 (1H, 
t, J= 6.0 Hz, H-3), 1.13 (3H, s, H-27), 0.97 (3H, 
s, H-26), 0.94 (3H, s, H-26), 0.94 (3H, s, H-25), 
0.87 (6H, s, H-29; H-30), 0.83 (3H, s, H-28), 
0.79 (3H, s, H-24). 13C-NMR, CDCl3, δppm: 
38.6 (C1), 26.9 (C2), 79.1 (C3), 38.8 (C4), 55.2 
(C5), 18.4 (C6), 32.7 (C7), 39.8 (C8), 47.7 (C9), 
36.9 (C10), 23.6 (C11), 121.7 (C12), 145.2 
(C13), 41.8 (C14), 26.2 (C15), 27.3 (C16), 32.5 
(C17), 47.3 (C18), 46.8 (C19), 31.1 (C20), 34.7 
(C21), 37.2 (C22), 28.1 (C23), 15.5 (C24), 15.6 
(C25), 16.8 (C26), 26.0 (C27), 28.4 (C28), 33.4 
(C29) and 23.7 (C30).  
III - RESULTS AND DISCUSSION 
The determination of the chemical structure 
of the oleanane type of this plant was easy by 
recognizing the characteristic resonances at low 
field with δppm 171.0, 145.2, 121.6, 80.9, 55.3 
(for β-amyrin acetate), 145.2, 121.7, 79.1, 55.2 
(for β-amyrin). Their spectroscopic data well 
suited to the ones of authentic samples. 
Plants of the genus Wedelia contained ent-
kaur-16-ene-19-oic acid and its derivatives. In 
these derivatives, one of the carbons at C-2, 3, 9, 
13, 15 of ent-kaur-16-ene-19-oic acid was 
oxygenated [1 - 6]. Wedelia urticaefolia also 
 129
contained ent-kaur-16-ene-19-oic acid and its 
structure was determined by spectroscopic 
method and the comparison with the one in 
Wedelia glauca [6]. Owing to the 1 and 2D-
NMR, some chemical shifts of protons and 
carbons thirteen were corrected comparing to 
the data presented in the literature [6]. 
(3) was quickly recognized as an ursane 
type triterpene by the typical resonances at 
δppm 138.1 (quaternary =C) and 125.0 (=CH) 
of the double bond at C-12. A resonance at 
δppm 80.5 (CH-O) was oxygenated carbon C-3 
as normal. The appearance of the second 
oxygenated carbon (CH-O) at δppm 67.0 caused  
Table 1: Spectroscopic data of (3) 
N δC δH (J in Hertz) HMBC (H to C) 
1 38.5   
2 25.2   
3 80.5 4.50 (1H, dd, 4.5,10.5) C1, C1’, C4 
4 37.8   
5 55.3   
6 18.2   
7 32.8   
8 39.6   
9 46.9   
10 36.8   
11 23.4  C12, C13 
12 125.1 5.19 (1H, t, 3.5) C14 
13 138.0   
14 44.1   
15 35.9  C13, C16  
16 67.1 4.22 (1H, dd, 5.5, 11.5) C28 
17 38.6   
18 60.7 1.51 (1H, d, 6,0) C12, C13, C16 
19 40.1   
20 39.5   
21 30.5   
22 35.2   
23 28.1 1.03 (3H, s) C3, C4, C5  
24 16.8 0.94 (3H, s) C3, C4, C5  
25 15.7 0.77 (3H, s) C1, C5, C9, C10 
26 16.9 1.15 (3H, s) C7, C8, C9, C14 
27 24.5 1.25 (3H, s) C4, C8, C13, C15 
28 21.9 0.98 (3H, s) C16, C17, C18 
29 21.4 0.89 (3H, d, 3.0) C18, C19, C20 
30 17.6 0.87 (3H, d, 2.5 ) C19, C20, C21 
1’ 173.7   
2’ 34.8 2.29 (2H, t, 7.5) C1’, C2’ 
3’ 31.9  C1’ 
4’-11’ 29.8, 29.7, 29.6, 29.6, 29.5, 29.5, 29.3, 29.2   
12’ 23.6   
13’ 22.7   
14’ 14.1 0.90 (3H, t, 6.5) C12’, C13’ 
 130
the difficulty in the determination the position 
of this carbon in the ursane skeleton. The 
HSQC, HMBC-NMR (figure 1) showed the 
correlation of the protons H-15, H-18, H-28 to 
C-16 so the second hydroxyl group was at C-16. 
The presence at the same time of the hydroxyl 
group at C-16 and the double bond at C-12 
caused carbon C-18 down field to δppm 60.7. 
Proton H-18 had correlations to C-12, C13 and 
C16.  
The hydroxyl group at C-3 was esterified to be 
–O-CO-R because the HMBC spectrum 
showed that H-3 (δppm 4.50) had the 
correlation with the resonant peak at δppm 
173.7 (C=O,     C-1’). This spectrum also 
showed the correlation of proton H-2’ with C-1’. 
Protons H-2’ (2H, triplet) confirmed the 
presence of the acyl group –O-CO-CH2-CH2-R 
at C-3. The long side chain ester at C-3 was 
determined by MS.
Table 2: Spectroscopic data of (4) 
δCN 
(*) (* *) (4) 
DEPT 
-NMR δH (J in Hertz) 
HMBC 
(H to C) 
1 40.8 39.5 40.7 -CH2- 1.89 (1H, brs), 0.82 (1H, m)  2, 20 
2 18.8 24.0 18.5 -CH2- 1.60 (2H, m)   
3 37.8 78.7 37.9 -CH2- 2.16 (1H, dbr, 14), 
1.01 (1H, m)  
 
4 43.9 48.0 43.9 Quater C   
5 57.2 56.4 57.1 CH 1.07 (1H, dbr)  6, 19 
6 21.9 21.5 21.8 -CH2- 1.85 (2H, m)  
7 33.1 40.9 39.7 -CH2- 2.04 (1H, dd, 2.5, 10.0)  
1.12 (1H, dd, 5.0, 11.5)  
9, 15 
8 64.9 43.8 43.7 Quater C   
9 55.2 55.1 55.1 CH 1.03 (1H, dbr)  8, 10, 12 
10 39.7 39.4 39.7 Quater C   
11 19.1 18.5 19.1 -CH2- 1.86 (1H, brs), 1.40 (1H, m)  10 
12 29.7 33.0 33.1 -CH2- 1.53 (2H, m), 1.42 (1H, m)   
13 41.7 43.7 44.2 CH 2.63 (1H, brs)   
14 44.3 38.7 41.3 -CH2- 1.42 (2H, m) 7, 8 
15 49.1 48.7 48.9 -CH2- 2.06 (2H, m)   7, 9, 13, 16, 17 
16 155.8 155.4 155.9 Quater 
C= 
  
17 103.0 103.3 103.0 =CH2 4.79 (1H, brs); 4.74 (1H, brs)  13, 15 
18 28.9 23.9 28.9 CH3 1.24 (3H, s)  3, 4, 5, 19 
19 184.5 180.6 183.3 COOH   
20 15.6 15.3 15.6 CH3 0.95 (3H, s)  5, 9, 10  
Note: (*): 
13C-NMR data of ent-kaur-16-ene-19-oic acid [5] 
(**):
13C-NMR data of 3α-tigloyloxykaur-16-ene-19-oic acid [6]. 
 
The ESI-MS (Positive mode) showed a 
molecular ion peak at m/z = 635 [M+H−H2O]+ 
corresponding to the formular of C44H76O3. The 
aglycone moiety with two hydroxyl groups had 
the mass of 441 amu (C30H49O2) so the side 
chain moiety had the mass of 211 amu. This 
mass well suited to the alcanoyl group of CH3–
(CH2)12-CO-. So the compound was determined 
as        3-O-tetradecanoylurs-12-ene-16β-ol. 
This compound was also found in the flowers of 
 131
Chrysanthemum morifolium (CAS registry 
number: 357419-19-3).    
Acknowledgements: This work was supported 
by Minister of Sciences and Technology through 
the National University- Ho Chi Minh City 
(Fundamental research in natural sciences, 
grand number 5006 06). 
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Rasheduzzaman, Mottakin A.K.M.,  Sohrab 
Mohammad Hossain, Hasan Choudhury M., 
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Rashid Mohammad A. Biochemical 
Systematics and Ecology. 31(5), 539 - 540 
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3. Calanasan Cleof A., Macleod John K. A. 
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Some di- and triterpenes of Wedelia urticaefolia (Bl.) (Asteraceae)

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Some di- and triterpenes of Wedelia urticaefolia (Bl.) (Asteraceae)

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