A new cinnamic acid glycoside from roots of Heracleum dissectum

Article abstract of DOI:10.1080/14786419.2017.1340285

From the roots of Heracleum dissectum Lebb., one new cinnamic acid glycoside derivative named dissectumoside (1), together with eight known compounds including three phenolics, three phenolic glycosides and two phenylpropanoic glycoside were isolated using various chromatographic methods. Among them compound 2–9 was isolated from the plant for the first time. Their structures were elucidated and identified on the basis of their physicochemical properties and by extensive analyses of NMR spectroscopy and high-resolution mass spectrometry. The results of triglyceride accumulation screening in 3T3-L1 cells showed that compounds 1, 5 and 9 exhibited significantly accelerating activities of adipogenesis in adipocytes.

Full text of DOI:10.1080/14786419.2017.1340285

Natural Product Research
Formerly Natural Product Letters
ISSN: 1478-6419 (Print) 1478-6427 (Online) Journal homepage: http://www.tandfonline.com/loi/gnpl20
A new cinnamic acid glycoside from roots of
Heracleum dissectum
Zhi-Gang Wang, Jie Mi, Xin-Rui Wang, Ya-Yu Huo, Ya-Jie Peng, Hai-Min Zhang,
Yang Gao & Hai-Long Zhang
To cite this article: Zhi-Gang Wang, Jie Mi, Xin-Rui Wang, Ya-Yu Huo, Ya-Jie Peng, Hai-
Min Zhang, Yang Gao & Hai-Long Zhang (2017): A new cinnamic acid glycoside from roots of
Heracleum dissectum, Natural Product Research, DOI: 10.1080/14786419.2017.1340285
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Date: 15 June 2017, At: 20:34

Natural Product research, 2017
https://doi.org/10.1080/14786419.2017.1340285
A new cinnamic acid glycoside from roots of Heracleum
dissectum
Zhi-Gang Wanga, Jie Mib, Xin-Rui Wangb, Ya-Yu Huob, Ya-Jie Pengb, Hai-Min Zhangb,
Yang Gaob and Hai-Long Zhangb
adepartment of Pharmaceutical analysis, heilongjiang university of chinese Medicine, harbin, china; bschool
of Pharmacy, Xi’an Jiaotong university, Xi’an, china
ABSTRACT
ARTICLE HISTORY
received 13 March 2017
accepted 13 May 2017
From the roots of Heracleum dissectum Lebb., one new cinnamic
acid glycoside derivative named dissectumoside (1), together with
eight known compounds including three phenolics, three phenolic
glycosides and two phenylpropanoic glycoside were isolated using
various chromatographic methods. Among them compound 2–9
was isolated from the plant for the first time. Their structures were
elucidated and identified on the basis of their physicochemical
properties and by extensive analyses of NMR spectroscopy and high-
resolution mass spectrometry. The results of triglyceride accumulation
screening in 3T3-L1 cells showed that compounds 1, 5 and 9 exhibited
significantly accelerating activities of adipogenesis in adipocytes.
KEYWORDS
Heracleum dissectum; edible
oroqen herb; cinnamic
acid glycoside; triglycerides
accumulation; 3t3-l1
adipocytes
1. Introduction
Heracleum dissectum is a perennial herb of Apiaceae family, widely distributed in the
north-eastern region of China and Far East areas of Russia. Oroqen people, mainly live in
North-east China, have eaten the young stems and leaves of H. dissectum for a long history
not only as the delicious vegetables but also as a remedy for treatment of diabetes and
CONTACT hai-long Zhang
zhhlcrest@mail.xjtu.edu.cn
supplemental data for this article can be accessed at https://doi.org/10.1080/14786419.2017.1340285.
© 2017 Informa uK limited, trading as taylor & Francis Group

2
Z.-G. WANG ET AL.
hypertension. Meanwhile, the roots are used as Oroqen folk medicine for dispelling wind
and eliminating dampness, curing rheumatoid diseases, waist or knee pain, headache, etc.
(Sun and Liu 2007). However, only a few phytochemical studies have been reported on H.
dissectum in which only essential oils (Papageorgiou et al. 1985; Montanarella et al. 1986)
and several simple coumarins (Belenovskaya et al. 1977) were isolated from this edible herb.
In our previous study, two new phenylproponoid glycosides were isolated and characterised
from the roots (Gao et al. 2014) and the antidiabetic effect of the aerial parts of H. dissectum
has also been verified in animals (Zhang et al. 2017). Herein, this paper described the isolation
and structure elucidation of one new cinnamic acid glycoside (1) and eight known com-
pounds (2–9) and TG accumulation activity in 3T3-L1 cells of all isolates from the roots of H.
dissectum.
2. Results and discussion
The ethyl acetate fraction and n-BuOH fraction of methanolic extract from the dried roots
of H. dissectum was subjected to column chromatography over silica gel normal-phase,
reversed-phase RP-18 and semi-preparative HPLC to give one new cinnamic acid glycoside
derivative, drupanin-4-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside, named dissectu-
moside (1) and eight known compounds, isovanillic acid (2) (Meng et al. 2000; Zhu et al.
2006), tyrosol (3) (Wang et al. 2015; Zhou et al. 2015), catechol (4) (Lai et al.1985), praeroside
(5) (Kong et al.1993; Nagatani et al. 2001), phenethyl-β- -glucopyranoside (6) (Xia et al. 2013;
d
Morikawa et al. 2016), tachioside (7) (Xiao et al. 2015), isotachioside (8) (Liu et al. 2014; Zhou
et al. 2016), coniferin (9) (Murata et al. 2008; She et al. 2013) (Figure 1).
Compound (1) was obtained as a white amorphous powder. The molecular formula was
established as C26H36O13 by HR–ESI–MS at m/z: 579.2070 ([M + Na]+, Calcd 579.2054). In the
1H NMR spectrum, protons at δH 7.41 (1H, dd, J = 8.5, 1.9 Hz), 7.31 (1H, d, J = 1.9 Hz) and
7.20 (1H, d, J = 8.5 Hz) revealed that there was a 1, 2, 4-trisubstituted aromatic ring in the
structure, and an E-type double bond deduced by the presence of protons at δH 7.56 (1H,
d, J = 15.9 Hz) and 6.29 (1H, d, J = 15.9 Hz). The 13C NMR and DEPT spectra of 1 showed 26
carbons including one carbonyl carbon, two quaternary aromatic carbons, one oxygenated
quaternary aromatic carbon, six olefinic methine carbons, one olefinic quaternary carbon,
eight oxymethine carbons, two oxymethylene carbons, two anomeric methine carbons,
one methylene carbon and two methyl carbons. In the 13C NMR and HMBC spectra, the
carbonyl carbon at δC 170.1 was correlated with the protons at δH 7.56 (1H, d, J = 15.9 Hz)
and 6.29 (1H, d, J = 15.9 Hz), which revealed that the occurrence of a trans-cinnamic acid
moiety. In addition, carbon at δC 133.8 (quaternary carbon) and δC 123.4 (its corresponding
proton at δH 5.32, 1H, t, J = 7.3 Hz) demonstrated the occurrence of a trisubstituted double
1
1
bond. In the H NMR and H-1H COSY spectra, protons at δH 3.38 (2H, m) correlated with
olefinic methine at δH 5.32 (1H, t, J = 7.3 Hz). Moreover, HMBC spectrum showed a crossing
peaks between two methyl protons at δH 1.71 (3H, s) and 1.73 (3H, s) and olefinic quaternary
carbon at δC 133.8. Above information revealed the presence of prenyl moiety in the mol-
ecule which attached on C-3 position of aromatic ring on the basis of observation of crossing
peak between proton at δH 3.38 (2H, m), 5.32 (1H, t, J = 7.4 Hz) and carbon at δC 132.6. The
NMR data of 1 was similar to that of drupanin (Schmitt et al. 1991; Hattori et al. 2011), that
was 3-prenyl-4-hydroxycinnamic acid.

NATURAL PRODUCT RESEARCH
3
Figure 1. chemical structures of compounds 1–9.
In the1H and 13C NMR spectra, two anomeric protons at δH 4.94 (1H, d, J = 7.3 Hz) and 4.35
(1H, d, J = 7.7 Hz) and their corresponding carbons at δC 101.9 and 104.7 indicated there
were two sugar units in the molecule. Acid hydrolysis of compound 1 followed by GC analysis
showed the sugar is D-glucose and the configuration of glucose was β-orientation deduce
from the coupling constant of their anomeric protons (J = 7.3 and 7.7 Hz, respectively). The
outer glucose unit attached to the 6′ position of the inner glucose unit by interpretation of
HMBC spectrum, in which proton at δH 4.35 (1H, d, J = 7.7 Hz, H-1″) correlated with carbon
at δC 69.8 (C-6′). Meanwhile, HMBC spectrum of 1 also showed a correlation between proton
at δH 4.94 (1H, d, J = 7.3 Hz, H-1′) and carbon at δC 158.4 (C-4) which indicated that the inner
glucose linked to the C-4 position of aromatic ring. Other connections were confirmed by
comprehensive analysis of 2D NMR spectroscopic methods, including HMQC, HMBC, 1H–1H
COSY and ROESY. Thus, compound 1 was identified as drupanin-4-O-β-d-glucopyranosyl-
(1→6)-β-d-glucopyranoside, and we named compound 1 as dissectumoside.
So far, phytochemical investigation on this plant is few. Only several simple coumarins
and essential oil have been isolated and identified from the whole plant of H. dissectum
(Belenovskaya et al. 1977; Papageorgiou et al. 1985; Montanarella et al. 1986) in the previous
study. In this present and our previous study, apart from coumarins, many phenolics and
phenylpropenoids including two new lignans and one new cinnamic acid glycoside deriv-
ative in this study have been isolated from the aerial parts and the roots of H. dissectum for
the first time (Gao et al. 2014). These results advance scientific knowledge of chemical con-
stituents of H. dissectum.
All compounds 1–9 were evaluated for their triglycerides accumulation activity in 3T3-L1
adipocytes (Table 1). Among them, compounds 1, 5 and 9 showed comparatively potent
activity of TG accumulation in cells. Additionally, compounds 6 and 8 also exhibited some
accelerating activity at a high concentration (30 μM), while other compounds exhibited weak
activity of adipogenesis. In the previous study, the antidiabetic effects of H. dissectum

4
Z.-G. WANG ET AL.
Table 1. activity of the isolated compounds 1–9 from the roots of H. dissectum on triglyceride levels in
3t3-l1 adipocytes.
Increase (%) in TG levels
Compounds
0
1
3
10
30 (μM)
1
0.0 1.2
0.0 2.5
0.0 3.1
0.0 2.4
0.0 4.0
0.0 3.4
0.0 1.3
0.0 4.5
0.0 2.8
0.0 1.3
7.8 1.2
1.8 1.0
−2.0 1.2
−4.2 2.4
6.9 1.6
−1.9 1.1
−3.9 2.8
4.7 3.0
17.9 2.0**
4.6 1.3
32.1 2.5**
6.2 1.1
4.8 2.1
−12.2 2.5
19.8 3.1**
10.8 2.7
7.8 2.2
9.2 1.4
18.2 3.0**
43.6 1.9**
40.1 2.4**
5.4 1.6
8.6 2.5
5.4 3.4
25.4 3.6**
12.1 3.9*
9.4 1.6
13.4 4.6*
17.6 1.8**
–
2
3
−3.2 1.5
−9.6 3.8
11.5 2.3**
−6.5 3.4
−8.2 3.0
6.3 3.3
4
5
6
7
8
9
8.2 3.2
28.6 1.8**
16.3 2.8**
37.2 2.2**
Troglitazone
Notes: Values represent means seM of % increase in tG levels (n = 4). significantly different from the control group.
*p < 0.05; **p < 0.01.
methnolic extract (HdME) were consolidated in vivo, in which HdME could significantly
improve glucose tolerance in mice and reduce the elevation of blood glucose in STZ-induced
diabetic mice (Zhang et al. 2017). Additionally, the compound exhibiting accelerating activity
onTG accumulation in vitro might provide antidiabetic effect in vivo (Zhang et al. 2007, 2009),
because this compound could effectively transport the glucose from the medium into the
adipocytes and dispose the glucose into triglyceride. Based on these results, we deduce the
new compound, dissectumoside (1), might possess antidiabetic effect in vivo which needs
further evaluation in the future study.
As regards to the structure-activity relationship, as shown in Table 1 and Figure 1, firstly,
the activity of glycosides (1, 5, 6, 7, 8 and 9) is better than that of non-glycosides (2, 3 and 4)
which demonstrated that glucosyl moiety in molecules is essential for this activity. Secondly,
among these glycosides (1, 5, 6, 7, 8 and 9), the activity of compounds (1, 5 and 9) is better
than that of others (6, 7 and 8), which reveals that 4-hydroxy phenpropyl moiety in aglycones
is important.
3. Experimental
3.1. General experimental procedures
The HR-ESI-MS was run on a Bruker microTOF-Q II mass spectrometer (Bruker Daltonics,
Billerica, MA). Nuclear magnetic resonance (NMR) spectra were measured and recorded on
a Bruker Avance III-400 spectrometer (Bruker, Rheinstetten, Germany). Tetramethylsilane
(TMS) was used as an internal standard. Chemical shifts are reported in δ (ppm), and coupling
constants (J) are expressed in hertz. Column chromatography (CC) was preformed over silica
gel (200–300 mesh, Qingdao Haiyang Chemical Co., Qingdao, China), ODS (100–200 mesh,
Fuji Silysia Chemical, Japan) or Sephadex LH-20 (GE Healthcare Bio-Sciences AB, Sweden).
Shimadzu semi-preparative HPLC (Shimadzu, Kyoto, Japan), Merges C18 column (250 × 10 mm
inner diameter, 5 μm, Hanbon, Suzhou, China) was used for the purification of compounds.
Triglyceride (TG) test kits were purchased from Beijing BHKT clinical reagent Co., Ltd (Beijing,
China) and their measurements were conducted on a multiplate reader (Synergy HT, BioTek,
USA).

NATURAL PRODUCT RESEARCH
5
3.2. Chemicals
Recombinant insulin, 3-isobutyl-1-methylxanthine (IBMX), dexamethasone and the other
chemicals were obtained from Sigma (St. Louis, MO, USA). Foetal calf serum (FCS), penicillin,
and streptomycin were obtained from Gibco (Invitrogen).
3.3. Plant material
The roots of H. dissectum Ledeb. were collected in September 2015, Tongbei, Heilongjiang
Province and authenticated by professor Xiaofeng Niu (The School of Pharmacy, Health
Science Center, Xi′an Jiaotong University, Xi′an China). The voucher specimen (KKL 150916)
was deposited in the school of Pharmacy, Health Science Center, Xi′an Jiaotong University.
3.4. Extraction and isolation
The air-dried roots of H. dissectum (6.5 kg) were extracted three times with methanol (3 × 40 L)
under reflux. After filtration, the solvent was evaporated under reduced pressure to yield a
crude methanol extract (HdME, 1.02 kg, 15.6%). A part of the residue (560.5 g) was suspended
in water (2 L) and successively partitioned with petroleum ether (PE, 4 × 2 L), CHCl3 (4 × 2 L),
EtOAc (4 × 2 L) and n-BuOH (4 × 2 L) to obtain PE fraction (68.3 g, 12.2%), CHCl3 fraction
(94.5 g, 16.8%), EtOAc fraction (9.4 g, 1.7%), n-BuOH fraction (130.1 g, 23.2%) and aqueous
fraction (253.9 g, 45.3%), respectively.
The EtOAc fraction (9.4 g) was chromatographed on a silica gel column (100–200 mesh)
using CHCl3/MeOH (1:0, 50:1, 20:1, 10:1, 5:1, 3:1, 1:1, 0:1, v/v) to give 19 fractions FrE1-FrE19
based on TLC analysis.
Fr.E4 (1 g) was divided into two subfractions (FrE4.1–FrE4.2) through a silica gel column
(50 g, 2.5 × 50 cm) gradiently eluted with CHCl3/MeOH (100:1, 50:1, 20:1, 1:0, v/v) according
to the TLC profiles. FrE4.1 was further separated by semi-preparative HPLC with a Megres
C18 column (30% MeOH in 1% CH3COOH with a flow rate of 3.0 mL/min) to give compound
2 (10 mg). FrE4.2 was further chromatographed over semi-preparative HPLC with a Megres
C18 column (15% MeOH in 1% CH3COOH, 3.0 mL/min) to give compound 3 (9 mg) and
compound 4 (5 mg).
The n-BuOH extract (111.6 g) was separated to silica gel column chromatography and
eluted with CHCl3/MeOH (1:0, 100:1, 50:1, 20:1, 10:1, 8:1, 6:1, 3:1, 2:1, 1:1, 0:1, v/v). The col-
lected fractions were combined based on their TLC characteristics to afford 30 fractions
FrB1-FrB30.
FrB12 (300 mg) was applied to ODS column eluting with MeOH/H2O (30:70, 50:50, 70:30,
100:0, v/v) to give two subfractions FrB12.1–FrB12.2. FrB12.1 was further subjected to
semi-preparative HPLC with a Thermo C18 column, which was eluted with 20% MeOH in
0.5% CH3COOH (3.0 mL/min) to give compound 5 (4 mg). FrB12.2 was purified by semi-
preparative HPLC with a Thermo C18 column (25% MeOH in 0.5% CH3COOH, 3.0 mL/min) to
give compound 6 (15 mg).
FrB20 (5 g) was chromatographed on ODS column, successively eluted with MeOH/H2O
(30:70, 45:55, 70:30, 100:0, v/v) to yield four subfractions FrB20.1–FrB20.4. FrB20.1 was sep-
arated to Sephadex LH-20 column, eluted with MeOH/H2O (3:7, v/v), to obtain two fractions
FrB20.1.1–FrB20.1.2. Then FrB20.1.2 was further chromatographed on semi-preparative HPLC

6
Z.-G. WANG ET AL.
with a Megres C18 column (5% MeOH-H2O with a flow rate of 3.0 mL/min) to give compound
7 (6 mg) and compound 8 (6 mg). Fr.B20.2 was subjected to Sephadex LH-20 column, eluted
with MeOH/H2O (3:7, v/v), to give two fractions FrB20.2.1–FrB20.2.2. And FrB20.2.1 was puri-
fied by semi-preparative HPLC with a Megres C18 column using MeOH/H2O (25:75, v/v) as
the eluent to give compound 9 (28 mg).
FrB25 (7 g) was applied to ODS column eluting with MeOH/H2O (40:70, 60:50, 75:30, 100:0,
v/v) to give three subfractions FrB25.1–FrB25.3. FrB25.2 was further chromatographed on
semi-preparative HPLC with a Megres C18 column (45% MeOH in 0.5% CH3COOH, 3.0 min)
to give compound 1 (16 mg).
3.4.1. Drupanin-4-O-β-d-glucopyranosyl-(1→6)-β-d-glucopyranoside (1)
White amorphous powder; IR (KBr) νmax: 3323, 2982, 1650 cm−1; HR-ESI MS at m/z 579.2070
[M + Na]+ (Calcd for C26H36O13: 579.2054). 1H NMR (400 MHz, CD3OD), δH: 7.31 (1H, d, J = 1.9 Hz,
H-2), 7.20 (1H, d, J = 8.5 Hz, H-5), 7.41 (1H, dd, J = 8.5, 1.9 Hz,H-6), 7.56 (1H, d, J = 15.9 Hz,
H-7), 6.28 (1H, d, J = 15.9 Hz, H-8), 3.38 (2H, m, H-10), 5.32 (1H, t, J = 7.4 Hz, H-11), 1.71 (3H,
s, H-13), 1.73 (1H, s, H-14), 4.94 (1H, d, J = 7.3 Hz, H-1′), 3.48 (1H, m, H-2′), 3.46 (1H, m, H-3′),
3.38 (1H, m, H-4′), 3.69 (1H, m, H-5′), 4.15 (1H, d, J = 10.4 Hz, H-6′), 3.80 (1H, m, H-6′), 4.35 (1H,
d, J = 7.7 Hz, H-1″), 3.19 (1H, m, H-2″), 3.28 (1H, m, H-3″), 3.26 (1H, m, H-4″), 3.17 (1H, m, H-5″),
3.62 (1H, dd, J = 12.0, 5.6 Hz, H-6″), 3.81 (1H, m, H-6″); 13C NMR (100 MHz, CD3OD), δC: 129.8
(C-1), 130.1 (C-2), 132.6 (C-3), 158.4 (C-4), 116.3 (C-5), 128.8 (C-6), 146.3 (C-7), 117.3 (C-8), 170.1
(C-9), 29.3 (C-10), 123.4 (C-11), 133.8 (C-12), 18.0 (C-13), 26.0 (C-14), 101.9 (C-1′), 74.9 (C-2′),
78.2 (C-3′), 71.4 (C-4′), 77.6 (C-5′), 69.8 (C-6′), 104.7 (C-1″), 75.5 (C-2″), 77.9 (C-3″), 71.6 (C-4″),
77.9 (C-5″), 62.7 (C-6″).
3.5. Adipogenesis in 3T3-L1 cells
3T3-L1 fibroblasts were seeded into 48-well multiplates (5.0 × 104 cells/well). After incubation
for 24 h, the cells were differentiated by changing to a differentiation medium (high glucose
DMEM supplemented with 10% FCS, 1 μM dexamethasone, 0.5 mM 3-isobutyl-1-methylx-
anthine, and 5 μg/mL insulin). After incubation for 3 days, the differentiation medium was
replaced by a maintenance medium (high glucose DMEM supplemented with 10% FCS and
5 μg/mL insulin). After another 4 days incubation (the fresh maintenance medium was
exchanged every other day), the cells were sonicated in H2O (200 μL/well). The triglyceride
concentration was measured using a commercial kit. The test compounds dissolved in DMSO
were added when the medium was changed every time and troglitazone was as a reference
compound in this assay.
3.6. Acid hydrolysis of new compound (1)
Compound 1 (3 mg) was heated in 5 mL of 2 M CF3COOH at 110°C. After 6 h, the reaction
mixture was diluted with 15 mL H2O and extracted with 5 mL EtOAc for three times. The
aqueous layer was evaporated, dissolved in anhydrous pyridine (100 μL), cysteine methyl
ester hydrochloride (200 μL) was added, and the mixture was warmed at 60°C for 1 h. Then
the trimethysilylation reagent HMDS-TMCS (2:1:10) was added and warmed at 60°C for
30 min. The supernatant was subjected to GC for sugar identification. The D-glucose was
confirmed by comparison of its retention time (tR 12.5 min) with that of authentic
standard.

NATURAL PRODUCT RESEARCH
7
4. Conclusion
To conclude, in the course of our continuous search for bioactive components from natural
resources, one new cinnamic acid glycoside derivative, drupanin-4-O-β-d-glucopyranosyl-
(1→6)-β-d-glucopyranoside (1) and eight known compounds (2–9) have been isolated from
the ethyl acetate and n-butanol fractions of methanol extract of the roots of H. disecctum.
This study indicated that phenolic glycosides are the main components of n-butanol fraction
of H. disecctum. Moreover, we investigated the accumulating activity on adipogenesis in
3T3-L1 adipocytes. As a result, the compound 1, as well as compounds 5 and 9, exhibited
significantly accelerating effects on accumulation of triglycerides in 3T3-L1 cells.
Disclosure statement
No potential conflict of interest was reported by the authors.
Funding
This work was supported by Natural Science Foundation of China [grant number 81673564]; the Natural
Science Foundation of Shaanxi Province [grant number 2015JM8413]; the start scientific research
fund for returned overseas students of Ministry of Education of China [grant number [2012] No. 940].
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