Study on chemical constituents of the leaves of sterculia foetida linn

 TẠP CHÍ KHOA HỌC HO CHI MINH CITY UNIVERSITY OF EDUCATION 
 TRƯỜNG ĐẠI HỌC SƯ PHẠM TP HỒ CHÍ MINH JOURNAL OF SCIENCE 
 Tập 18, Số 3 (2021): 425-430 Vol. 18, No. 3 (2021): 425-430 
 ISSN: 
 1859-3100 Website:  
 Research Article* 
 STUDY ON CHEMICAL CONSTITUENTS OF THE LEAVES 
 OF STERCULIA FOETIDA LINN. 
 Nguyen Thi Quynh Trang1, Duong Thuc Huy2, Pham Nguyen Kim Tuyen1* 
 1Saigon University, Vietnam 
 2Ho Chi Minh City University of Education, Việt Nam 
 *Corresponding author: Pham Nguyen Kim Tuyen – Email: phngktuyen@gmail.com 
 Received: January 18, 2021; Revised: March 23, 2021; Accepted: March 25, 2021 
ABSTRACT 
 Phytochemical data of Sterculia foetida Linn. are scarce. The leaves of Sterculia foetida Linn. 
collected in Binh Thuan Province were chemically investigated using multiple chromatographic 
methods. Three compounds, hesperidin (1), kaempferol (2) and ursolic acid (3) were isolated and 
elucidated. Their chemical structures were elucidated by comparing their spectroscopic data with 
those in previous studies. These compounds were found for the first time from the leaves of 
Sterculia foetida Linn. Compounds 1 was obtained for the first time in Sterculia genus. 
 Keywords: hesperidin; kaempferol; Sterculia foetida Linn.; ursolic acid 
1. Introduction 
 Sterculia foetida Linn. (Sterculiaceae) is grown in tropical areas around the world 
(Chi, 2002; Peng et al., 2009). The latex of this species can be used as herbal drinks and 
beverages (Vo, 2002). The S. foetida extracts showed antidiabetic, anticancer, antibacterial, 
anti-inflammatory and analgesic activities (Peng et al., 2009). Flavonoids, triterpenoids, 
steroids and fatty acids were addressed (Peng et al., 2009; Mujumdar et al., 2000; 
Anjaneyulu et al., 1981, Kale et al., 2011). Our previous phytochemical studies on this 
species reported some oleanane-type triterpenoids, quercetin derivatives and phenolic 
compounds (Pham et al., 2018; Pham et al., 2019). This paper presented the isolation and 
structural elucidation of three compounds, including hesperidin (1), kaempferol (2) and 
ursolic acid (3) from S. foetida leaves collected in Binh Thuan Province, Vietnam. 
Cite this article as: Nguyen Thi Quynh Trang, Duong Thuc Huy, & Pham Nguyen Kim Tuyen (2021). Study on 
chemical constituents of the leaves of sterculia foetida Linn. Ho Chi Minh City University of Education Journal 
of Science, 18(3), 425-430. 
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HCMUE Journal of Science Vol. 18, No. 3 (2021): 425-430 
 30
 OH 29
 6" OCH 19 21
 3' 3 12
 O 4' OH 13
 4' 11
 '" O 17 28
 1 HO B B 25 26
 O 14 COOH
 H3C O H HO O HO O
 1" 7 2 1 9
HO A 7 2 15
 OH C A C 5 7
 3 3 3
 HO H 5 3 5 HO 27
 OH OH
 O O 24 23
 1 OH OH 2 3
 ( ) ( ) ( ) 
 Figure 1. Chemical structures of isolated compounds 1-3 
2. Experimental 
2.1. General experimental procedures 
 The NMR spectra were recorded on a Bruker Avance 500 spectrometer (500 MHz 
 1 13
for H–NMR and 125 MHz for C–NMR) in acetone-d6, and DMSO-d6 solutions. Thin 
layer chromatography was carried out on silica gel 60 (Merck, 40-63 μm) and spots were 
visualized by spraying with 10% H2SO4 solution, followed by heating. 
2.2. Plant material 
 The leaves of S. foetida were collected in Binh Thuan Province, Vietnam in October 
2017. Its scientific name was identified by botanist Dr. Dang Van Son, Institute of Tropical 
Biology. A voucher specimen (No.SFC/TUYEN-1017A) was deposited at the herbarium in 
the laboratory of Faculty of Environmental Science, Saigon University. 
2.3. Extraction and isolation 
 The powdered leaves of S. foetida (12.0 kg) were macerated with ethanol for three 
times (3 x 40 L) at room temperature. The solvent was removed from the residue under 
low pressure to obtain the crude extract (1830 g). This crude extract was successively 
applied to liquid-liquid partition giving hexane (450.5 g), chloroform (650.0 g), ethyl 
acetate (30.1 g) extracts and the aqueous partition. 
 The chloroform extract (400.0 g) was applied on a silica gel column chromatography 
with mobile phase hexane-ethyl acetate (100:0, 75:25, 50:50, 25:75, 0:100, v/v, 
respectively) and then ethyl acetate-methanol (90:10, 80:20, 70:30, 60:40, 0:100, v/v, 
respectively) to give eight fractions (SFC.I-SFC.VIII). Fraction SFC.VII (9.2 g) was 
subjected to a silica gel column chromatography with gradient solvent of chloroform-
methanol (80:20, 70:30, 60:40) to yield nine sub-fractions (SFC.VII.1-SFC.VII.9). Sub-
fraction SFC.VII.1 (2.3 g) was chromatographed on a silica gel using chloroform-methanol 
(20:1, 10:1, 5:1) as eluent to give 3 (4.9 mg). Sub-fractions SFC.VII.6 (1.6 g) was 
rechromatographed on a silica gel eluting with chloroform-methanol (95:5, 90:10, 85:15, 
80:20, 75:25) to afford 1 (5.2 mg) and 2 (7.8 mg). 
 • Hesperidin (1) (Lahmer et al., 2015). Yellow amorphous powder. The 1H-NMR 
data (500 MHz, DMSO-d6, δ ppm, J in Hertz): 12.05 (1H, brs,5-OH), 6.95 (1H, dd, 8.0, 
2.0, H-6’), 6.89 (1H, d, 2.0, H-5’), 6.81 (1H, d, 8.0, H-2’), 6.15 (1H, d, 2.0, H-6), 6.13 (1H, 
d, 2.0, H-8), 5.49 (1H, dd, 11.0, 5.0, H-2), 4.98 (1H, d, 7.5, H-1”), 4.57 (1H, brs, H-1”’), 
3.79 (3H, s, 4’-OCH3), 3.23 (1H, m, H-3ax), 2.77 (1H, d, 17.0, H-3eq) and 1.09 (3H, d, 5.5, 
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HCMUE Journal of Science Nguyen Thi Quynh Trang et al. 
 13
H-6”’). C-NMR (125 MHz, DMSO-d6): Hesperitin skeleton: 78.1 (C-2), 42.3 (C-3), 197.8 
(C-4), 163.0 (C-5), 96.4 (C-6), 165.3 (C-7), 95.6 (C-8), 162.6 (C-9), 103.5 (C-10), 131.1 
(C-1’), 114.0 (C-2’), 146.2 (C-3’), 148.2 (C-4’), 112.0 (C-5’), 117.7 (C-6’); D-
glucopyranosyl unit: 99.8 (C-1”), 72.0 (C-2”), 75.5 (C-3”), 70.7 (C-4”), 76.3 (C-5”) and 
66.0 (C-6”); L-rhamnopyranosyl moiety: 100.1 (C-1”’), 69.7 (C-2”’), 70.4 (C-3”’), 73.1 
(C-4”’), 68.3 (C-5”’) and 18.1 (C-6”’); and 55.8 (4’-OCH3). 
 • Kaempferol (2) (Li et al., 2008). Yellow amorphous powder. The 1H–NMR data 
(Acetone-d6, δ ppm, J in Hertz): 8.14 (2H, d, 8.5, H-2’, H-6’), 7.13 (2H, d, 8.5, H-3’, H-
 13
5’), 6.53 (1H, d, 2.0, H-8) and 6.26 (1H, d, 2.0, H-6). C-NMR (125 MHz, Acetone-d6): 
147.0 (C-2), 137.1 (C-3), 176.6 (C-4), 162.3 (C-5), 99.3 (C-6), 166.1 (C-7), 94.5 (C-8), 
158.2 (C-9), 104.5 (C-10), 123.6 (C-1’), 130.7 (C-2’, C-6’), 116.1 (C-3’, C-5’) and 160.1 
(C-4’). 
 1
 • Ursolic acid (3) (Silva et al., 2008). White powder. The H-NMR data (DMSO-d6, δ 
ppm, J in Hertz): 5.14 (1H, t, 4.0.;3.5, H-12), 3.20 (1H, dd, 8.0;7.0, H-3), 1.09 (3H, s, H-
27), 0.98 (3H, s, H-25), 0.94 (3H, s, H-30), 0.92 (3H, s, H-26), 0.86 (3H, s, H-29), 
 13
0.81(3H, s, H-24) and 0.77 (3H, s, H-23). The C-NMR (125 HZ, DMSO-d6): 38.6 (C-1), 
26.9 (C-2), 78.8 (C-3), 36.9 (C-4), 55.2 (C-5), 18.3 (C-6), 31.0 (C-7), 39.4 (C-8), 47.5 (C-
9), 36.9 (C-10), 23.2 (C-11), 125.5 (C-12), 138.1 (C-13), 41.9 (C-14), 32.5 (C-15), 22.1 
(C-16), 47.7 (C-17), 52.7 (C-18), 30.0 (C-19), 38.8 (C-20), 27.8 (C-21), 36.7 (C-22), 27.9 
(C-23), 15.9 (C-24), 15.5 (C-25), 16.8 (C-26), 23.4 (C27), 180.2 (C-28), 16.9 (C-29) and 
21.0 (C-30). 
3. Results and discussion 
 Compound 1 was obtained as a yellow amorphous powder. The 1H-NMR spectrum 
of 1 displayed signals of a flavanone skeleton. Its spectrum showed a down field signal at δ 
12.05 (1H, brs), indicating the presence of a chelated hydroxyl group at C-5 position. Two 
meta–coupled doublet proton signals at δH 6.15 (1H, d, 2.0, H-6) and 6.13 (1H, d, 2.0, H-
8), each integrated for one proton, were assigned to H–6 and H–8, respectively, of a 5,7-
dihydroxy A ring system. The 1’,3’,4’-trisubstituted B ring system in flavanone skeleton, 
in addition, was determined by the presence of three aromatic proton signals on ABX 
system at δH 6.81 (1H, d, 8.0, H-2’), 6.89 (1H, d, 2.0, H-5’) and 6.95 (1H, dd, 8.0, 2.0, H-
6’). Furthermore, the flavanone skeleton was identified by the presence of one oxymethine 
proton at δH 5.49 (1H, dd, 11.0, 5.0, H-2) and two methylen protons at δH 3.23 (1H, m, H-
3ax) and 2.77 (1H, d, 16.0, H-3eq). These data indicated that 1 was a hesperitin derivative. 
 1
Moreover, the H-NMR data displayed two anomeric proton signals at δH 4.98 (1H, d, 7.5, 
H-1”) and 4.57 (1H, brs, H-1”’), which indicated 1 was a hesperitin diglycoside flavanone. 
The 13C-NMR spectra were fully supported by the presence of twenty-eight carbon signals, 
including fifteen carbons of a flavanone skeleton, twelve carbons of two sugar units and 
one methoxy carbon. The hesperitin flavanone derivative was confirmed by the presence of 
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fifteen carbons, including one carbonyl carbon at δC 197.8 (C-4), twelve aromatic carbon 
signals from 95.6 ppm to 165.2 ppm, one oxymethine carbon at δC 78.1(C-2), and one 
methylen carbon at δC 42.3 (C-3). The β-D-glucopyranosyl unit was demonstrated by the 
displaying one anomeric proton with the large coupling constant at δH 4.98 (1H, d, 7.5, H–
 1
1”) in the H–NMR spectra and the addition of one anomeric carbon signal at δC 99.8 (C–
1”) and five oxygenated carbons from 66.0 ppm to 76.3 ppm in the 13C–NMR spectrum. 
The α-L-rhamnopyranosyl moiety was identified by the presence of one singlet anomeric 
proton at δH 4.57 (1H, s, H–1”’) along with one anomeric carbon signal at δC 100.1 (C–
1”’), four oxygenated carbons from 18.1 ppm to 73.1 ppm and one typical L-
rhamnopyranosyl methyl carbon at δC 18.1 (C-6”’). HMBC correlations from aromatic 
protons at δH 6.81 (1H, d, 8.0, H-2’), and 6.95 (1H, dd, 8.0, 2.0, H-6’) to carbon at δC 78.1 
(C-2) confirmed the attachment of B benzene ring to C-2. Additionally, the methoxy 
proton signal at δH 3.79 (3H, s, 4’-OCH3) correlated with aromatic carbon at δC 148.2 (C-
4’) in the HMBC spectra which confirmed that the aglycone was herperetin skeleton. The 
β-D-glucopyranosyl unit was attached to C-7 of a herperetin skeleton by the HMBC 
correlation between the anomeric proton at δH 4.98 (1H, d, 7.5, H–1”) and oxygenated 
carbon at δC 165.3 (C-7). The α-L-rhamnopyranosyl moiety was linked to C-6 of the β-D-
glucopyranosyl unit by the HMBC correlations between the anomeric proton δH 4.57 (1H, s, 
H–1”’) and oxygenated methylene carbon at δC 66.0 (C-6”). The other COSY, HSQC and 
HMBC correlations were strongly agreed with the assignment. Based on these 
spectroscopic data and comparison with previous report (Lahmer et al., 2015), the 
chemical structure of 1 was determined as hesperitin7-O-[α-L-rhamnopyranosyl-(1 6)]-β-
D-glucopyranoside (Hesperidin). Hesperidin was isolated for the first time from Sterculia 
genus. 
 OH
 6" H OCH
 3' 3
 O 4'
 O '
 1'" 1 B
 HO O
 H3C O H HO O
 " 2 H
 HO OH 1 7 A C
 3 H
 HO H 5 H
 OH H
 1 OH O
 ( ) 
 Figure 2. The main HMBC correlations of compound 1 
 Compound 2 was obtained as a yellow amorphous powder. Its NMR spectrum 
showed similar signals of 1, except for the appearing of one oxygenated aromatic carbon at 
δC 147.0 (C-2), one olefinic carbon at δC 137.1 (C-3), and disappearing two sugar units in 2 
which was corresponded to a flavonol framework. The para–disubstituted benzene ring 
(ring B) was determined by the displaying of two doublet proton signals with a large 
coupling constant at δH 8.14 (2H, d, 8.5 Hz, H–2’, H–6’) and 7.13 (2H, d, 8.5 Hz, H–3’, H–
5’). These data indicated that 2 was a kaempferol skeleton. The 13C–NMR spectrum were 
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HCMUE Journal of Science Nguyen Thi Quynh Trang et al. 
strongly supported by the displaying of 15 carbons in the down field, comprising one 
carbonyl carbon at δC 176.6 (C–4), and the rest fourteen carbons from 94.5 ppm to 162.3 
ppm. The good compatibility between its NMR data and those in the literature (Li et al.., 
2008) determined the structure of 4 to be kaempferol. 
 Compound 3 was obtained as a white powder. The NMR data of 3 displayed signals 
 1
of a triterpenoid skeleton. The H-NMR determined the signals of an olefinic proton at δH 
5.14 (1H, t, 4.0.;3.5, H-12), an oxygenated proton at δH 3.20 (1H, dd, 8.0;7.0, H-3) and 
seven methyl proton signals from 0.77 ppm to 1.09 ppm. The 13C-NMR exhibited thirty 
carbons, including one carboxyl carbon at δC 180.2 (C-28), two olefinic carbons at δC 
125.5 (C-12), and 138.1 (C-13) of a double bond at C-12/C-13 and the rest carbons in 
ursane skeleton. The HSQC and HMBC spectra determined this suggestion. The 
comparison NMR data of 3 with those reported in the literature, 3 were assigned as ursolic 
acid (Silva et al., 2008) 
4. Conclusions 
 From the leaves of S. foetida collected in Binh Thuan Province, three compounds, 
including one diglycoside flavanone hesperidin (1), one flavonol kaempferol (2) and one 
ursane-type triterpenoid ursolic acid (3) were isolated for the first time. Their chemical 
structures were determined by using the NMR spectroscopic method as well as comparison 
with previous studies. Compound 1, to the best of our knowledge, was isolated from 
Sterculia genus for the first time. Further studies on this species are on the progress. 
  Conflict of Interest: Authors have no conflict of interest to declare. 
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 Sterculia foetida Linn. Indian Journal of Chemiscal Section B, 20(1), 87-88. 
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 NGHIÊN CỨU THÀNH PHẦN HÓA HỌC CỦA LÁ CÂY TRÔM 
 STERCULIA FOETIDA LINN. 
 Nguyễn Thị Quỳnh Trang1, Dương Thúc Huy2, Phạm Nguyễn Kim Tuyến1* 
 1Trường Đại học Sài Gòn, Việt Nam 
 2Trường Đại học Sư phạm Thành phố Hồ Chí Minh, Việt Nam 
 *Tác giả liên hệ: Phạm Nguyễn Kim Tuyến – Email: phngktuyen@gmail.com 
 Ngày nhận bài: 18-01-2021; ngày nhận bài sửa: 23-3-2021, ngày chấp nhận đăng: 25-3-2021 
TÓM TẮT 
 Nghiên cứu hóa thực vật của loài Sterculia foetida Linn. chưa được tìm thấy nhiều. Nghiên 
cứu được thực hiện trên lá cây Trôm Sterculia foetida Linn. thu hoạch ở tỉnh Bình thuận bằng các 
phương pháp sắc kí khác nhau. Ba hợp chất hesperidin (1), kaempferol (2) và ursolic acid (3) được 
cô lập và xác định cấu trúc hóa học. Cấu trúc hóa học của các hợp chất được xác định bằng các 
phương pháp phổ nghiệm đồng thời so sánh với các dữ liệu phổ đã được công bố. Đây là lần đầu 
tiên các hợp chất này được cô lập từ lá cây Trôm Sterculia foetida Linn. Hợp chất 1 lần đầu tiên 
được biết có hiện diện trong chi Sterculia. 
 Từ khóa: hesperidin; kaempferol; Sterculia foetida Linn.; ursolic acid 
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