Diterpene glycosides and phenolic compounds from the fruits of Xanthium strumarium

Cite this paper: Vietnam J. Chem., 2020, 58(5), 648-653 Article 
DOI: 10.1002/vjch.202000061 
648 Wiley Online Library © 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH 
Diterpene glycosides and phenolic compounds from the fruits of 
Xanthium strumarium 
Phan Van Kiem
1,2*
, Nguyen Huy Hoang
1
, Vu Kim Thu
3
, Bui Huu Tai
1,2
, Nguyen Xuan Nhiem
1,2
1
Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST), 
18 Hoang Quoc Viet, Cau Giay district, Hanoi 10000, Viet Nam 
2
Graduate University of Science and Technology, VAST, 
18 Hoang Quoc Viet, Cau Giay district, Hanoi 10000, Viet Nam 
3
Hanoi University of Mining and Geology, Pho Vien, Duc Thang, Bac Tu Liem Dist., Hanoi 10000, Viet Nam 
Submitted April 25, 2020; Accepted May 21, 2020 
Abstract 
Seven compounds including two diterpene glucosides atractyloside (1), carboxyatractyloside (2), and five phenolic 
compounds as 5-O-caffeoylquinic acid (3), 1,5-di-O-caffeoylquinic acid (4), 2,3-dihydroxy-1-(4(hydroxy-3-
methoxyphenyl)-propan-1-one (5), (erythro)-1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propandiol (6), and p-
hydroxybenzaldehyde (7) were isolated from the fruits of Xanthium strumarium. Their chemical structures were 
determined using ESI-MS, 1D NMR, and 2D NMR spectra as well as by comparison of the spectral data with those 
reported in the literature. Compounds 4 and 5 were reported from Xanthium genus for the first time. To our best 
knowledge, all these compounds were firstly reported from X. strumarium growing in Vietnam. 
Keywords. Xanthium strumarium, atractyloside, carboxyatractyloside, phenolic. 
1. INTRODUCTION 
Xanthium strumarium L. (Asteraceae) is a common 
and well-known traditional herbal medicine in China 
and Vietnam.
[1,2]
 It has been extensively applied to 
treat many diseases, such as rhinitis, urticaria, 
rheumatism bacterial, nasal sinusitis, headache, 
gastric ulcer, fungal infections and arthritis.
[1,2]
From the leaves, fruits, and roots of this plant, there 
are more than 170 compounds have been isolated 
including sesquiterpenoids, phenylpropenoids, 
lignanoids, steroids, glycosides, coumarins, 
thiazides, flavonoids, anthraquinones, 
naphthoquinones and other compounds.
[1,2]
However, no reports on phytochemical and biological 
studies of X. strumarium growing in Vietnam. This 
paper reported the isolation and structural elucidation 
of seven compounds including two diterpene 
glucosides and five other phenolic compounds from 
the fruits of this plant growing in Vietnam. 
2. MATERIALS AND METHODS 
2.1. Plant materials 
The fruits of Xanthium strumarium L. were 
collected in Viet Cuong, Yen My, Hung Yen, 
Vietnam in December 2019 and identified by Dr 
Nguyen The Cuong, Institute of Ecology and 
Biological Resources. A voucher specimen (NCCT-
P91) was deposited at the Institute of Marine 
Biochemistry, VAST. 
2.2. General experimental procedures 
See reference: 
[11]
2.3. Extraction and isolation 
The dried fruits of X. strumarium (10.0 kg) were 
grounded and ultrasonically extracted with MeOH at 
room temperature for three times (each, 20 L 
MeOH, 30 minutes). After filtration, the solvent was 
evaporated in vacuo to give the MeOH extract (220 
g). This crude extract was suspended with water (2 
L) and successively partitioned in n-hexane, 
dichloromethane, and ethyl acetate to give hexane 
(155 g), dichloromethane (12 g), ethyl acetate 
extracts (15 g), and water layer. 
The water layer was chromatographed on a 
Diaion HP-20 column eluting with water to remove 
sugar components, then increase concentration of 
Vietnam Journal of Chemistry Phan Van Kiem et al. 
© 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 649 
methanol in water (25, 50, 75 and 100 %, v/v) to 
obtain four fractions, KN1-KN4, respectively. The 
KN3 fraction was separated on a silica gel column 
chromatography, eluting with dichloromethane/ 
methanol (20/1, 10/1, 5/1, 1/1, v/v) to give four sub-
fractions KN3A-KN3D, respectively. The KN3B 
(2.5 g) was chromatographed on a RP-18 column 
eluting with acetone/water (1/2, v/v) to give four 
smaller fractions, KN3B1-KN3B4. The KN3B1 was 
chromatographed on a silica gel column eluting with 
dichloromethane/acetone/water (1/4/0.5, v/v/v) as 
solvent to give four fractions, K3A-K3D. The K3A 
was purified on HPLC column (J’sphere ODS H-80, 
250 mm×20 mm column) eluting with 40 % 
acetonitrile to yield 1 (11.0 mg). The K3D was 
purified on HPLC column (J’sphere ODS H-80, 250 
mm×20 mm column) eluting with 45 % acetonitrile 
to yield 2 (9.0 mg). Compounds 3 (8.5 mg) and 4 
(7.6 mg) from KN3B2 fraction by purifying on 
HPLC using J’sphere ODS H-80, 250 mm×20 mm 
column, ACN in H2O (32 %). The KN3B3 (3.1 g) 
fraction was chromatographed on a silica gel column 
eluting with dichloromethane/methanol (20/1, 10/1, 
5/1, v/v) to give compounds 5 (8.4 mg), 6 (9.1 mg), 
and 7 (4.5 mg). 
Figure 1: Chemical structures of compounds 1-7 
Atractyloside (1): Colorless amorphous powder; 
[ ] 
 -54
o
 (c 0.1, MeOH); mp. 205-206 
o
C; ESI-MS 
m/z 725.2129 [M-H]
-
, (Calcd. [C30H45O16S2]
-
, 
725.2149); 
1
H-NMR (CD3OD, 500 MHz) and 
13
C-
NMR (CD3OD, 125 MHz) data, see table 1. 
Carboxyatractyloside (2): Colorless amorphous 
powder; [ ] 
 -45.0 (c 0.1, MeOH); mp. 273-275 
o
C. HR-ESI-MS m/z 793.2012 [M+Na]
+
, (Calcd. 
[C31H46O18S2Na]
-
, 793.2023); 
1
H-NMR (CD3OD, 
500 MHz) and 
13
C-NMR (CD3OD, 125 MHz) data, 
see table 1. 
5-O-caffeoylquinic acid (neochlorogenic acid) 
(3): Colorless amorphous; [ ] 
 +52 (c 0.1, MeOH); 
ESI-MS m/z 353 [M-H]
-
; C16H18O9. 
1
H-NMR 
(CD3OD, 500 MHz) and 
13
C-NMR (CD3OD, 125 
MHz) data, see table 2. 
1,5-di-O-caffeoylquinic acid (4): Colorless 
amorphous; [ ] 
 +34.0 (c 0.1, MeOH); ESI-MS 
m/z 515 [M-H]
-
; C25H24O12; 
1
H-NMR  ... 9 [M-H]
-
; C17H20O6. 
1
H-NMR (CD3OD, 500 
MHz) and 
13
C-NMR (CD3OD, 125 MHz) data, see 
table 3. 
p-Hydroxybenzaldehyde (7): Light yellow 
powder; Mp 112-116 
o
C. ESI-MS m/z 123 [M+H]
+
. 
1
H-NMR (500 MHz, DMSO-d6) δ (ppm): 7.68 (2H, 
d, J = 8.5 Hz, H-2, H-6), 6.83 (2H, d, J = 8.5 Hz, H-
3, H-5), 9.71 (1H, s, H-7). 
13
C-NMR (125 MHz, 
DMSO-d6) δ (ppm): 126.8 (C-1), 132.1 (C-2, C-6), 
116.4 (C-3, C-5), 166.0 (C-4), 190.2 (C-7). 
Vietnam Journal of Chemistry Diterpene glycosides and phenolic compounds 
 © 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 650 
3. RESULTS AND DISCUSSION 
Compound 1 was obtained as a colorless amorphous 
powder. The molecular formula was determined as 
C30H16O16S2 based on HR-ESI-MS m/z 725.2129 
[(Calcd. [C30H45O16S2]
-
, 725.2149). The 
1
H-NMR 
spectrum of 1 (in CD3OD) showed one methyl 
singlet at δH 1.04, two other singlets of the =CH2 
protons at δH 5.20 and 5.09, two methine cacbinol 
protons at δH 3.78 (br s) and 4.30 (m). 
Table 1: 
1
H- and 
13
C-NMR data for compounds 1 and 2 and reference compounds 
C 
1 2 
#δC 
 a,bδC
 a,cδH (mult., J in Hz)
 @δC 
 a,bδC
 a,cδH (mult., J in Hz)
1 47.9 48.5 0.77 (dd, 11.5, 11.5) 
2.32 (dd, 11.5, 2.0) 
49.3 48.5 0.83 (dd, 11.5, 11.5) 
2.29 (dd, 11.5, 2.0) 
2 72.6 74.3 4.30 (m) 76.6 74.6 4.39 (m) 
3 35.2 35.9 1.20 (m)/2.45 (dd, 10.0, 
2.0) 
42.4 40.9 1.50*/2.56 (dd, 10.0, 
3.0) 
4 45.6 46.2 2.64 (t, 4.0) 63.2 61.1 - 
5 49.4 50.5 1.44 (m) 54.1 53.2 1.73 (m) 
6 25.8 26.6 1.67 (m)/1.95 (m) 25.7 23.9 1.77 (m)/1.84 (m) 
7 35.9 36.2 1.46 (m)/1.70 (m) 37.6 36.2 1.44 (m)/1.63 (m) 
8 47.2 48.5 - 50.2 48.7 - 
9 52.7 54.7 1.06 (d, 7.5) 55.6 55.1 1.10 (d, 7.5) 
10 40.2 41.8 - 42.8 41.7 - 
11 17.9 19.2 1.50 (m)/1.65 (m) 20.9 19.3 1.50 (m)/1.65 (m) 
12 32.3 33.6 1.50 (m)/1.64 (m) 35.0 33.7 1.50 (m)/1.64 (m) 
13 41.8 43.7 2.72 (br s) 44.8 43.7 2.71 (br s) 
14 36.0 37.2 1.40 (dd, 11.0, 5.0) 
1.91 (d, 11.0) 
38.8 38.8 1.39 (dd, 11.5, 4.5) 
1.92 (d, 11.5) 
15 81.3 83.6 3.78 (br s) 85.0 83.5 - 
16 159.5 160.4 - 161.5 160.4 - 
17 107.4 109.0 5.20 (s)/5.09 (s) 111.7 108.9 5.19 (s)/5.08 (s) 
18 181.3 179.1 - 
19 178.4 179.5 - 180.6 179.1 - 
20 16.9 17.3 1.04 (s) 19.9 17.9 1.05 (s) 
1 98.1 100.5 4.75 (d, 8.0) 100.9 100.7 4.74 (d, 8.0) 
2 71.9 73..4 4.90 (dd, 9.0, 8.0) 74.6 72.6 4.80 (dd, 9.0, 8.0) 
3 77.7 80.3 4.59 (t, 9.0) 81.8 82.9 4.42 (t, 9.0) 
4 73.6 75.3 4.35 (t, 9.0) 77.0 70.9 3.65 (t, 9.0) 
5 75.3 76.3 3.53 (m) 76.9 77.3 3.42 (m) 
6 61.1 62.4 3.90 (br s) 63.2 62.3 3.74 (dd, 11.5, 4.0) 
3.88 (br d, 11.5) 
1 170.7 174.7 - 177.7 173.9 - 
2 43.0 44.5 2.30 (d, 7.0) 46.0 44.4 2.28 (d, 7.0) 
3 24.7 26.4 2.10 (m) 28.1 26.5 2.13 (m) 
4 22.5 23.1 0.99 (d, 6.5) 24.9 23.0 0.99 (d, 6.5) 
5 22.5 23.0 0.98 (d, 6.5) 24.8 22.9 0.98 (d, 6.5) 
Measured in a)CD3OD, 
b)125 MHz, c)500 MHz. #δC of atractyloside in DMSO-d6,
[4] @δC of carboxyatractyloside in D2O
[4] 
*Overlapped signals. 
In addition, one glucosyl unit was identified by 
the exhibition of an anomeric proton at δH 4.75 (J = 
7.5 Hz), two oxygenated methylene protons at δH 
3.90 (2H), and the isovaleryl moiety was identified 
by two doublet methyl groups at δH 0.98 and 0.99 (J 
= 6.5 Hz), and two methylene protons at δH 2.30 (d, 
J = 7.0 Hz). The 
13
C-NMR spectrum of 1 exhibited 
30 carbon signals including two carbonyl groups at 
δC 179.5 and 174.7, the >C=CH2 group at δC 160.4 
(C) and 109.0 (CH2), one glucosyl unit was 
identified by the signals at 100.5, 73.4, 80.3, 75.3, 
76.3 (5 x CH) and 62.4 (CH2), and the isovaleryl 
Vietnam Journal of Chemistry Phan Van Kiem et al. 
© 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 651 
ester moiety was identified by signals at 174.7 (C), 
44.5 (CH2), 26.4 (CH), 23.0 and 23.1 (2xCH3). 
Besides, two signals at 74.3 (CH) and 83.6 (CH) 
were assigned to two methine cacbinol carbons of 
the aglycone. The above data suggested that 
compound 1 was a diterpene glycoside bearing a 
isoprenyl moiety by an ester linkage. By comparing 
the NMR and MS data of 1 with the corresponding 
data of the reported literature of atractyloside, 
compound 1 was identified as atractyloside.
[4]
 The 
NMR data of 1 and of atractyloside were found to 
match well (table 1).
[4]
 Furthermore, the structure as 
well as the assignments of all protons and carbons of 
1 were confirmed by HSQC and HMBC spectra as 
shown in figure 2. The HMBC correlation from 
anomeric proton (δH 4.75) to carbon δC 74.3 
confirmed the sugar unit linked to C-2 of the 
aglycone The HMBC correlation from H-2 of the 
sugar (δH 4.90, dd, J = 9.0, 8.0 Hz) to carbonyl 
carbon at δC 174.1 determined that the isovaleryl 
ester moiety attached to C-2 of the glucosyl unit. 
The sugar linkage was confirmed in the β form as 
judged from the coupling constant (J = 8.0 Hz) of 
the anomeric proton at δH 4.75 ppm, and two sulfuric 
acid moiety were confirmed by the matching NMR 
data of 1 with atractyloside as well as by HR-ESI MS 
result. From the above data, compound 1 was 
identified as atractyloside, the compound have been
isolated from X. strumarium growing in China, 
however it was first isolated from this plant growing 
in Vietnam. 
Compound 2 was obtained as a colorless 
amorphous powder. The molecular formula was 
determined as C31H46O18S2 based on HR-ESI-MS 
m/z 793.2012 [M+Na]
+
, (Calcd. [C31H46O18S2Na]
-
, 
793.2023). The NMR spectra of 2 were similar to the 
corresponding NMR spectra of 1 except for the 
carbon signals at C-3 (δC 40.9) and C-4 (δC 61.1) of 
2 differed from C-3 (δC 35.9) and C-4 (δC 46.2) of 1. 
This evidence together with the HR-ESI-MS results 
suggested that compound 2 was 
cacboxyatractyloside. The assignments of carbon and 
proton chemical shifts were determined first by 
comparing the NMR data of 2 with those of 
cacboxyatractyloside (table 1),
[4]
 and further 
confirmed by HSQC and HMBC spectra (figure 2). 
All the spectroscopic data of 2 were found to match 
well with cacboxyatractyloside, a compound had 
been isolated from X. strumarium growing in China, 
however, it was first isolated from this plant growing 
in Vietnam. Carboxyatractyloside is a highly toxic 
diterpene glycoside that inhibits the ADP/ATP 
translocase. It's about 10 times more potent than 
atractyloside. While atractyloside is effective in the 
inhibition of oxidative phosphorylation, carboxy-
atractyloside is considered to be more effective.
[5,6,7]
Table 2: 
1
H- and 
13
C-NMR data for compounds 3 and 4 and reference compounds 
C 
3 
4
#
δC
 a,b
δC
 a,c
δH (mult., J, Hz)
C 
@
δC
 a,b
δC
 a,c
δH (mult., J, Hz)
1 73.6 73.1 - 1 80.1 81.9 - 
2 37.2 37.0 1.60-2.00* 2 34.2 34.9 1.60-2.00* 
3 68.3 69.0 3.92 (m) 3 66.5 67.0 3.92 (m) 
4 70.5 71.2 3.48 (m) 4 73.2 74.2 3.48 (m) 
5 70.9 71.5 5.17 (br s) 5 71.4 72.0 5.17 (br s) 
6 37.0 37.2 1.60-2.00* 6 39.4 39.4 1.60-2.00* 
7 175.0 176.7 - 7 173.1 173.8 - 
1′ 125.6 125.5 - 1′,1′′ 125.7; 125.8 125.4; 125.8 - 
2′ 114.8 114.7 7.05 (br s) 2′,2′′ 116.2; 115.7 115.0; 115.8 7.03 (d, 2.0); 7.10 (d, 2.0) 
3′ 145.6 145.7 3′,3′′ 145.3; 146.0 145.9; 145.9 - 
4′ 148.3 148.5 - 4′,4′′ 148.6; 148.9 148.1; 148.9 - 
5′ 115.8 115.8 6.77 (br d, 8.0) 5′,5′′ 116.4; 116.3 116.0; 115.0 6.73 (d, 8.0); 6.74 (d, 8.0) 
6′ 
121.4 121.2 6.97 (br d, 8.0) 
6′,6′′ 
120.5; 121.4 120.2; 121.3 6.92 (dd, 8.0, 2.0); 
6.95 (dd, 8.0, 2.0) 
7′ 144.9 144.6 7.45 (d, 16.0) 7′,7′′ 145.8; 145.8 144.8; 143.6 7.45 (d, 16.0); 7.47 (d, 16.0) 
8′ 114.4 114.6 6.23 (d, 16.0) 8′,8′′ 114.6; 114.9 114.3; 114.3 6.24 (d, 16.0); 6.17 (d, 16.0) 
9′ 165.8 166.3 - 9′,9′′ 165.5; 165.7 166.3; 165.0 - 
Measured in a)CD3OD, 
b)125 MHz, c)500 MHz. #δC of 5-O-caffeoylquinic acid in DMSO-d6,
[8] @δC of 1,5-di-O-caffeoylquinic acid in 
DMSO-d6.
[8] 
Vietnam Journal of Chemistry Diterpene glycosides and phenolic compounds 
 © 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 652 
Figure 2: The key HMBC correlations of compounds 1 and 2 
Table 3: 
1
H- and 
13
C-NMR data for compounds 5 and 6 and reference compounds 
C 
5 6
#δC
 a,bδC
 a,cδH (mult., J, Hz)
 @δC
 a,bδC
 a,cδH (mult., J, Hz)
1 199.7 199.6 - 74.6 75.6 4.94 (d, 5.5) 
2 75.8 75.5 5.13 (m) 57.1 56.7 2.94 (m) 
3 
67.1 66.3 3.74 (dd, 11.5, 5.0) 
3.90 (dd, 11.5, 3.5) 
64.5 64.5 3.71 (dd, 11.5, 2.0) 
3.86 (dd, 11.5, 6.5) 
1′ 125.4 128.0 - 137.1 136.5 - 
2′ 113.1 112.5 7.59 (d, 1.5) 111.6 111.7 6.66 (d, 2.0) 
3′ 149.2 149.3 - 148.2 148.5 - 
4′ 153.8 154.0 - 146.9 146.6 - 
5′ 116.2 116.0 6.90 (d, 8.0) 115.9 115.7 6.72 (d, 8.5) 
6′ 125.4 125.1 7.61 (dd, 8.0, 1.5) 120.2 120.3 6.68 (dd, 8.5, 2.0) 
3′-OMe 57.1 56.5 3.93 (s) 55.7 56.2 3.70 (s) 
1′′ 132.6 132.3 - 
2′′ 114.8 114.6 6.68 (d, 2.0) 
3′′ 148.1 148.4 - 
4′′ 146.7 146.2 - 
5′′ 115.8 115.5 6.72 (d, 8.5) 
6′′ 123.3 123.2 6.63 (dd, 8.5, 2.0) 
3′′-OMe 55.8 56.3 3.78 (s) 
Measured in a)CD3OD, 
b)125 MHz, c)500 MHz; #δC of 2,3-dihydroxy-1-(4(hydroxy-3-methoxyphenyl)-propan-1-one
[9] in DMSO-d6, 
@δC of (erythro)-1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propandiol
[10] in Py-d5. 
The ESI-MS of 3 exhibited a quasi-molecular 
ion peak at m/z 353 [M-H]
-
, corresponding to the 
molecular formula of C16H18O9. The 
1
H-NMR 
spectrum of 3 showed three ABX signals of the 
1,3,4-tri-substituted aromatic ring at δH 7.05 (s), 6.97 
(d, J = 8.0 Hz), 6.77 (d, J = 8.0 Hz), a trans double 
bond at δH 6.23 and 7.45 (d, J = 16.0 Hz). These 
data together with the 
13
C-NMR data [as δC 166.3 
(C=O), 114.6 and 144.6 (CH=CH trans), 125.5, 
114.7, 145.7, 148.5, 115.8, 121.2 (Ar ring)] 
confirmed the appearance of the caffeoyl moiety. 
The quinic acid was also identified by the 
appearance of carbon chemical shifts at δC 176.7 
(C=O), 73.1 (C), 71.5, 71.2, 69.0 (3xCH), 37.0 
(2xCH2), as well as by proton signals at δH 1.64-2.00 
(4H, 2 x CH2), 3.48 (1H), 3.92 (1H), and 5.17 (1H). 
All the NMR data of 3 were compared to that of 3-
O-caffeoylquinic acid and found to match.
[8]
From the NMR spectra and ESI-MS results, 
compound 4 was found to be similar to 3, suggesting 
that 4 also was a caffeoylquinic acid as 3. However, 
compound 4 had one more caffeoyl group compared 
to 3. The NMR data of 4 were directly compared to 
the corresponding data of 1,5-di-O-caffeoylquinic 
acid
[8]
 and found to match (table 2). This is the first 
time compounds 3 and 4 were isolated from X. 
strumarium. Compounds 5 and 6 were determined as 
2,3-dihydroxy-1-(4(hydroxy-3-methoxyphenyl)-
propan-1-one (5),
[9]
 (erythro)-1,2-bis(4-hydroxy-3-
methoxyphenyl)-1,3-propandiol (6)
[10]
 by their NMR 
data with those reported in the literature. 
Compounds 5 and 6 were also isolated from X. 
strumarium for the first time. From the ESI-MS and 
NMR data, compound 7 was identified as p-
Vietnam Journal of Chemistry Phan Van Kiem et al. 
© 2020 Vietnam Academy of Science and Technology, Hanoi & Wiley-VCH GmbH www.vjc.wiley-vch.de 653 
formylphenol, a compound had been reported from X. 
strumarium.
[2] 
Acknowledgment. The authors are indebted to 
Vietnam Academy of Science and Technology for 
financial support under grant number 
NVCC38.02/20-20. 
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truxinic acids from Trigonostemon honbaensis with 
their anoctamin-1 inhibitory activity, Bioorganic 
Chemistry, 2020, 102, 104058. 
Corresponding author: Phan Van Kiem 
Institute of Marine Biochemistry 
Vietnam Academy of Science and Technology 
18, Hoang Quoc Viet, Cau Giay district, Hanoi 10000, Viet Nam 
E-mail: phankiem@yahoo.com.