A novel phenolic acid from the fruits of Rosa soulieana

Article abstract of DOI:10.1080/14786419.2014.915826

From the n-BuOH-soluble fraction of a MeOH extract of the fruits of Rosa soulieana, one new phenolic glucoside (1) was isolated along with five known compounds, comprising two lignin glycosides, two flavonoid glycosides and a phenolic glycoside. The chemical structure of the new compound was elucidated by extensive spectroscopic analyses, including ESI-MS, UV, IR, ¹H and ¹³C NMR, DEPT and 2D NMR (HSQC and HMBC). All the isolated compounds were evaluated for their antioxidant activity by using ABTS (2,2′-azino- bis(3-ethylbenzoline-6-sulfonic acid)) assay. Among these compounds, 1, 3 and 6 exhibited strong scavenging activity in ABTS^√+(SC₅₀ = 102.10, 193.85, 65.38 μol/L, respectively) compared with the positive control l-ascorbic acid (Vc) (SC50= 117.16 μol/L). 2014

Full text of DOI:10.1080/14786419.2014.915826

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A novel phenolic acid from the fruits of
Rosa soulieana
ab
ab
ac
a
Wenjun He , Chunyan Yang , Mingkui Wang & Fu Li
a
Chengdu Institute of Biology, Chinese Academy of Sciences,
Chengdu 610041, P.R. China
b
Graduate University of Chinese Academy of Sciences, Beijing
1
00049, P.R. China
c
Key Laboratory of Mountain Ecological Restoration and
Bioresource Utilization, Chinese Academy of Sciences, Chengdu
10041, P.R. China
6
Published online: 15 May 2014.
To cite this article: Wenjun He, Chunyan Yang, Mingkui Wang & Fu Li (2014) A novel phenolic acid
from the fruits of Rosa soulieana, Natural Product Research: Formerly Natural Product Letters,
28:15, 1127-1133, DOI: 10.1080/14786419.2014.915826
To link to this article: http://dx.doi.org/10.1080/14786419.2014.915826
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Natural Product Research, 2014
Vol. 28, No. 15, 1127–1133, http://dx.doi.org/10.1080/14786419.2014.915826
A novel phenolic acid from the fruits of Rosa soulieana
ab
Wenjun He , Chunyan Yang , Mingkui Wang and Fu Li *
ab
ac
a
a
b
Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, P.R. China; Graduate
c
University of Chinese Academy of Sciences, Beijing 100049, P.R. China; Key Laboratory of Mountain
Ecological Restoration and Bioresource Utilization, Chinese Academy of Sciences, Chengdu 610041,
P.R. China
(
Received 8 February 2014; final version received 13 April 2014)
From the n-BuOH-soluble fraction of a MeOH extract of the fruits of Rosa soulieana,
one new phenolic glucoside (1) was isolated along with five known compounds,
comprising two lignin glycosides, two flavonoid glycosides and a phenolic glycoside.
The chemical structure of the new compound was elucidated by extensive
1
13
spectroscopic analyses, including ESI-MS, UV, IR, H and C NMR, DEPT and 2D
NMR (HSQC and HMBC). All the isolated compounds were evaluated for their
0
assay. Among these compounds, 1, 3 and 6 exhibited strong scavenging activity in
antioxidant activity by using ABTS (2,2 -azino-bis(3-ethylbenzoline-6-sulfonic acid))
zþ
ABTS (SC50 ¼ 102.10, 193.85, 65.38 mmol/L, respectively) compared with the
positive control L-ascorbic acid (Vc) (SC ¼ 117.16 mmol/L).
5
0
Keywords: Rosa soulieana; phenolic glucoside; antioxidative; ABTS
1
. Introduction
Rosa soulieana belonging to the family of Rosaceae is widely distributed in the dry valley of
Sichuan province, China (Zhou et al. 2009). Most of the plants of the genus Rosa are rich in
triterpenoids, phenolics and essential oils with various biological activities (Liang et al.
1
989; Fang et al. 1991; Velioglu & Mazza 1991; Okuda et al. 1992; Hashidoko 1996).
In recent years, phenolic compounds have attracted more and more attention due to their
ability to scavenge superfluous free radicals in the body which can cause oxidative damage to
biomolecules and eventually lead to many chronic diseases such as cancer, atherosclerosis,
diabetics, myocardial infarction, cardiovascular diseases, chronic inflammation and stroke
(
Uttara et al. 2009). Previous phytochemical investigation of the fruits of R. soulieana led to
the isolation of several non-polar triterpenoids which can be used to treat cardiovascular
disorders (Chen et al. 2000). We have reported the isolation and antioxidant activity of nine
phenolic compounds from the flowers of R. soulieana (Yang et al. 2013). However, phenolics
from the fruits of this plant have rarely been reported. Therefore, this study focused on
further investigation on the chemical constituent of R. soulieana fruits in order to provide a
scientific foundation for further use of this plant. Herein, we describe the isolation and
structural elucidation of one new phenolic compound, together with five known compounds.
Moreover, the antioxidant activity of the isolated phenolic compounds was evaluated by
using the ABTS assay.
*
Corresponding author. Email: lifu@cib.ac.cn
q 2014 Taylor & Francis

1
128
W. He et al.
2
2
. Results and discussion
.1. Structural elucidation of the isolated compounds
The n-BuOH part of methanol extract of R. soulieana was subjected to silica gel, Sephadex LH-
0 column chromatography (CC) and preparative HPLC to yield compounds 1–6. The structures
2
of these compounds were elucidated on the basis of spectroscopic data (1D and 2D NMR, MS)
and chemical evidences.
Compound 1 was obtained as a yellow gum. The molecular formula of 1 was determined as
þ
C H O based on the pseudo-molecular ion at m/z [M þ Na] 501.1007 (calcd for
2
2 22 12
C H O Na, 501.1003) in HR-ESI-MS, requiring 12 degrees of unsaturation. The UV spectrum
15 26 9
revealed absorption at lmax 200 nm (e 13,734) and lmax 290 nm (e 7950) in MeOH. The IR
21
2
spectrum indicated the presence of hydroxyl groups (3389 cm ), carbonyl groups (1688 cm
1
)
and CZOZC bonds (1099 and 1075 cm ). In the H NMR spectrum (Figure S1), the proton
2
1
1
0
0
0
0
signals at d 6.89 (2H, d, J ¼ 7.2 Hz, H-2 , 6 ) and d 6.46 (2H, d, J ¼ 7.2 Hz, H-3 , 5 ) indicated
H
H
an aromatic moiety in an A2B2 coupling system. While the signals at d 5.94 (1H, s, H-5) and d
H
H
5
benzene ring. The H NMR spectrum also revealed a typical anomeric proton at d 4.76 (1H, d,
.83 (1H, s, H-3) suggested the presence of a 1,2,4,6-tetrasubstituted or 1,3,4,6-tetrasubstituted
1
H
0
0
0
13
H-1 ) and two methylene protons at d 2.97 (2H, s, H-7 ). The C NMR spectrum (Figure S2)
H
presented 6 signals belonging to a hexose residue, 12 signals for 2 aromatic rings, 2 signals for 2
carboxyls and 2 signals for a carbonyl and a methylene. The hexose was determined to be D-
glucose by TLC analysis and measuring the optical rotation of the acid hydrolysis solution of 1.
The coupling constant of the anomeric proton revealed a b configuration (Li et al. 2012). The
HMBC (Figure S3) correlations between H-3 (d 5.83) and C-4, C-7, C-8 suggested that the
H
carboxyl groups were connected to C-2 and C-4, respectively (Figure 2). Furthermore, the
HMBC correlations between H-3 (d 5.83) and C-7, C-8, and the HMBC correlation between H-
H
0
5
displayed HMBC correlations with C-1 , C-6 and C-8 , indicating that the carbonyl group was
(dH 5.94) and C-8 provided further evidence that H-3 and H-5 are in meta-position. H-7
0
0
0
0
linked to C-1 and the methylene group was linked to C-1 . The glucose residue was connected to
0
0
C-6 according to the HMBC correlation between H-1 and C-6. Based on the above-mentioned
evidences, compound 1 was identified and named as soulieana acid 1 (Figure 1). The known
0
0
0
compounds were identified as (7S, 8S)-threo-7,9,9 -tetrehydroxy-3,3 -dimethoxy-8-O-4 -
neolignan-4-O-b-D-glucopyrano-side (2) (Huo et al. 2008), dihydrodehydrodiconiferyl alcohol
-O-b-D-glucopyranoside (3) (Abe & Yamauchi 1986), miquelianin (4) (Parejo et al. 2004),
0
4
kaempferol-3-O-b-D-glucopyranoside-7-O-a-L-rhamnoside (5) (Ni et al. 2012) and methyl 3-O-
b-glucopyranosyl-gallate (6) (Kuang et al. 1989; Ma et al. 2013) based on NMR data and MS
analysis, as well as by comparing the spectral data with those reported.
2
.2. Antioxidant activity of the isolated compounds and the crude samples
The experiment was to apply an antioxidant activity-guided screening procedure to the extracts
of the fruits of R. soulieana similar to the former study of flower of R. soulieana (Yang et al.
2
013). Furthermore, we also screened antioxidants from the crude methanol extract of the fruits
of the R. soulieana, which exhibited potential antioxidant activity with 10.4% inhibition against
ABTS at 50 mg/mL (Figure 2). The study demonstrated that the n-butanol-soluble (RB) extract
contained the bioactive compounds responsible for the antioxidant activity. Bioactivity-guided
fractionation of antioxidant constituents from RB extracts led to the isolation of compounds 1–6
with different levels of antioxidant activity at 50 mg/mL (Figure 1).
In this article, the antioxidant activity of the isolated phenolic compounds was evaluated by
zþ
using the ABTS radical-scavenging assay with L-ascorbic acid (Vc) as the positive control, and
the results are shown in Table 1.

Natural Product Research
1129
Figure 1. Chemical structures of compounds 1–6.
Compound 6 displayed the most excellent antioxidant activity due to the presence of a
catechol group and its low molecular weight. It was reported that small molecules had better
access to the radical site, leading to high antioxidant activity (Huang et al. 2005). The carboxyl
Figure 2. ABTS radical scavenging activities of the crude samples and the isolated compounds from the
fruits of R. soulieana. The concentration of the tested samples was 50–mg/mL. FRT, the methanol extract;
FRW, the aqueous extract; FRP; the petroleum ether soluble extract; FRE; the ethyl acetate soluble extract;
FRB, the n-butanol-soluble extract.

1
130
W. He et al.
Table 1. ABTS radical-scavenging activity of the isolated compounds from the fruits of R. soulieana.
Compounds
Molecular weight
SC50 values (mM)
1
2
3
4
5
6
Vc
478
540
522
478
592
346
176
102.10
274.10
193.85
262.32
.500.00
65.38
117.16
groups on the aromatic ring in compound 1 may be responsible for its strong activity. Compound
exhibited better antioxidant activity than compound 5 due to the presence of the catechol group
4
0
0
at C-3 and C-4 . Moreover, the glycosylation at C-7 OH in compound 5 also reduced its activity.
As a result, compound 5 exhibited very poor antioxidant activity. Compounds 2 and 3 possessed
similar antioxidant activity because of their similar chemical structures.
3
3
. Experimental
.1. General experimental procedures
The solvents, which were used for extraction and isolation, were of analytical grade (Chengdu
Kenong Chemical Reagent Factory, Chengdu, China). Silica gel (200–300 mesh, Qingdao Marine
Chemical Factory, Qingdao, China), silica gel 60 (40–63 mm, Merck, Darmstadt, Germany) and
Sephadex LH-20 (Pharmacia, Uppsala, Sweden) were used for open CC. TLC was performed on
pre-coated silica gel plates (GF254, 0.25mm, Kang-Bi-Nuo Silysia Chemical Ltd., Yantai,
China). IR spectrum was acquired with a Perkin-Elmer 1725X-FT spectrometer (PerkinElmer
Instruments LLC, Granville, Hamilton City Metro, DE, USA) with a KBr disk. NMR spectra were
recorded on a Bruker Avance-600 spectrometer (Bruker Corporation, Stockholm, Sweden). The
chemical shift (d) values are given in ppm with TMS as internal standard, and coupling constants
DECA
(J) are in Hz. ESI-MS and HR-ESI-MS were measured on Finnigan LCQ
USA) and Bruker Apex-III mass spectrometer (Bruker Corporation, Stockholm, Sweden),
(San Jose, CA,
0
respectively. 2,2 -Azinobis(3-ethylbenzothiazoline-6-sulfonic acid) diammonium salt (ABTS),
potassium persulphate (K S O ) and all the chromatographic solvents (methanol and acetonitrile)
for analytical HPLC were purchased from Sigma (St Louis, MO, USA).
2
2 8
3
.2. Plant material
The fruits of R. soulieana were sampled from the dry valley in Sichuan province, China, in June
011 and identified by Professor Xinfen Gao, Chengdu Institute of Biology, Chinese Academy
2
of Sciences. A voucher specimen (20110622) has been deposited at the Natural Product
Research Center, Chengdu Institute of Biology, Chinese Academy of Sciences.
3
.3. Extraction and isolation
The dried and powdered fruits (4.5 kg) of R. soulieana were extracted with methanol at room
temperature for three times in an ultrasonic bath. The extracted solution was concentrated under
reduced pressure to yield a dark brown residue (252.6 g), which was suspended in water and
extracted with petroleum ether, ethyl acetate and n-butanol, successively. The n-BuOH fraction
(
62.1 g) was subjected to a silica gel (200–300 mesh) column, eluting with increasing polarity of
CHCl –MeOH (100:0 ! 0:100) to obtain six fractions (Fr. 1–Fr. 6) combined by TLC. Fr. 2
3
was subjected to a Sephadex LH-20 column with a step gradient of CH OH–H O (1:50, 1:40,
3
2

Natural Product Research
1131
1
:30, 1:20, 1:10), followed by preparative RP-HPLC to yield compounds 2 (40 mg) and 3
22 mg). Fr. 3 was chromatographed over a C18 column using mixtures of CH OH–H O as
(
3
2
eluent to yield compound 1 (15 mg). Fr. 4 was purified by RP-C18 column to yield three
subfractions (Fr. 4-1, Fr. 4-2 and Fr. 4-3). Fr. 4-2 was further separated by preparative RP-HPLC
to yield compounds 4 (36 mg), 5 (20 mg) and 6 (25 mg).
3
.4. Acid hydrolysis of compound 1 and measurement of optical rotation of the solution
Compound 1 (5 mg) was hydrolysed in HCl (0.5 mL)/H O (1.5 mL)/dioxane (3 mL) under reflux
2
for 2 h. After diluting with H O, the hydrolysate mixture was extracted with EtOAc. The H O
2
2
layer was neutralised with NaHCO and then concentrated to dryness under reduced pressure.
3
The residue was re-dissolved with H O (2 mL) for optical rotation measurement and TLC
2
analysis. The sugar from the water layer was identified as glucose by TLC analysis. The optical
2
0
D
rotation of the water solution was determined to be ½aꢀ þ 48.98 (c ¼ 0.09 H O), indicating that
2
the absolute configuration of the glucose was D.
3
.5. Spectroscopic data
2
D
0
Compound 1: C H O , yellow powder (MeOH); ½aꢀ -0.1378 (c ¼ 1.00, MeOH); UV l
2
2
22 12
max
(
MeOH) nm(e): 200 (13,734), 290 nm (7950); IR (KBr) n
3389, 2922, 1688, 1616, 1515,
max
2
1
þ
1
099, 1075 cm ; ESI-MS m/z 501 [M þ Na] ; HR-ESI-MS m/z 501.1007 (calcd for
þ
3 4
1
[
M þ Na] , 501.1003). H NMR (600 MHz, CD OD-d ) d (ppm): 5.83 (1H, s, H-3), 5.94 (1H, s,
0
0
H-5), 6.89 (1H, d, J ¼ 7.2 Hz, H-2 ), 6.46 (1H, d, J ¼ 7.2 Hz, H-3 ), 6.46 (1H, d, J ¼ 7.2 Hz, H-
0
0
00
00
5
), 6.98 (1H, d, J ¼ 7.2 Hz, H-6 ), 4.76 (1H, d, J ¼ 7.8 Hz, H-1 ), 3.41 (1H, m, H-2 ), 3.31(1H,
00 00 00 00
m, 3 ), 3.30 (1H, m, H-4 ), 3.34 (1H, t, J ¼ 9.0 Hz, H-5 ), 3.37 (1H, brs, J ¼ 12.0 Hz, H-6 -a),
00
.57 (1H, m, H-6 -b). C NMR (150 MHz, CD OD-d ) d (ppm): 106.2 (C-1), 101.8 (C-2), 91.9
3 4
13
3
0
0
(
C-3), 102.1 (C-4), 96.1 (C-5), 156.9 (C-6), 173.2 (C-7), 170.3 (C-8), 124.3 (C-1 ), 131.2 (C-2 ,
0 0 0 0 0 00 00
), 114.4 (C-3 , 5 ), 155.9 (C-4 ), 40.1 (C-7 ), 195.5 (C-8 ), 100.3 (C-1 ), 72.6 (C-2 ), 76.9 (C-
0
0
6
3
0
00
00
00
), 69.8 (C-4 ), 75.9 (C-5 ), 61.0 (C-6 ).
þ
1
Compound 2: C H O , white amorphous powder, ESI-MS m/z 563 [M þ Na] . H NMR
2
6 36 12
(
600 MHz, CD OD-d ) d (ppm): 7.12 (1H, brs, H-2), 6.99 (1H, d, J ¼ 8.2 Hz, H-5), 6.97 (1H, d,
3
4
J ¼ 8.2 Hz, H-6), 4.87 (1H, d, J ¼ 5.2 Hz, H-7), 4.24 (1H, m, H-8), 3.47 (1H, d, J ¼ 4.9 Hz, H-
0
0
9
a), 3.83 (1H, dd, J ¼ 12.0, 4.2 Hz, H-9b), 6.83 (1H, brs, H-2 ), 6.94 (1H, d, J ¼ 8.4 Hz, H-5 ),
0
0
0
6
.68 (1H, d, J ¼ 8.4 Hz, H-6 ), 2.70 (2H, t, J ¼ 8.2 Hz, H-7 ), 1.88 (2H, m, H-8 ), 3.63 (2H, t,
0
0
J ¼ 6.5 Hz, H-9 ), 3.92 (3H, s, H-3-OCH ), 3.91 (3H, s, H-3 -OCH ), 4.92 (1H, d, J ¼ 5.4 Hz, H-
3
3
00
00 00 00 00
1
), 3.49 (1H, m, H-2 ), 3.54 (1H, m, H-3 ), 3.39 (1H, m, H-4 ), 3.56 (1H, m, H-5 ), 3.57 (1H, m,
0
0
00
H-6 a), 3.76 (1H, dd, J ¼ 10.6, 2.0 Hz, H-6 b).
Compound 3: C H O , white amorphous powder, ESI-MS m/z 545 [M þ Na] . H NMR
þ
1
2
6 34 11
(
600 MHz, CD OD-d ) d (ppm): 7.02 (1H, brs, H-2), 7.14 (1H, d, J ¼ 8.3 Hz, H-5), 6.93 (1H, dd,
3
4
J ¼ 8.3, 1.8 Hz, H-6), 5.54 (1H, d, J ¼ 5.9 Hz, H-7), 3.38 (1H, m, H-8), 3.83 (1H, m, H-9a), 3.66
0
0
0
(
1H, m, H-9b), 6.72 (1H, brs, H-2 ), 6.70 (1H, brs, H-6 ), 2.61 (1H, t, J ¼ 7.7 Hz, H-7 ), 1.81 (1H,
0 0 00 00
m, H-8 ), 3.56 (1H, t, J ¼ 6.3 Hz, H-9 ), 4.89 (1H, d, J ¼ 7.3 Hz, H-1 ), 3.49 (1H, m, H-2 ), 3.48
0
0
00
00
00
(
1H, m, H-3 ), 3.45 (1H, m, H-4 ), 3.75 (1H, m, H-5 ), 3.38 (2H, d, J ¼ 4.8 Hz, H-6 ), 3.85, 3.81
(
each 3H, s, -OMe).
þ
1
Compound 4: C H O , yellow amorphous powder, ESI-MS m/z 501 [M þ Na] . H NMR
2
1 18 13
0
400 MHz, DMSO-d ) d (ppm): 6.22 (1H, s, H-6), 6.42 (1H, s, H-8), 7.56 (1H, s, H-2 ), 6.85 (1H,
6
d, J ¼ 8.4 Hz, H-5 ), 7.61 (1H, d, J ¼ 8.4 Hz, H-6 ), 5.50 (1H, d, J ¼ 7.2 Hz, H-1 ), 3.50 (1H, m,
(
0
0
00
0
0
00
00
00
H-2 ), 3.43 (1H, m, H-3 ), 3.57 (1H, m, H-4 ), 3.58 (1H, d, J ¼ 9.6 Hz, H-5 ).

1
132
W. He et al.
þ
1
Compounds 5: C H O , yellow amorphous powder, ESI-MS m/z 615 [M þ Na] . H NMR
2
7 30 15
0
400 MHz, DMSO-d ) d (ppm): 12.59 (1H, s, 5-OH), 10.20 (1H, s, 4 -OH), 8.05 (2H, d,
6
(
0
0
0
0
J ¼ 8.9 Hz, H-2 , 6 ), 6.90 (2H, d, J ¼ 8.9 Hz, H-3 , 5 ), 6.80 (1H, d, J ¼ 2.0 Hz, H-8), 6.43 (1H,
0
00
000
d, J ¼ 2.0 Hz, H-6), 5.55 (1H, d, J ¼ 1.2 Hz, H-Rha-1 ), 1.22 (3H, d, J ¼ 8.2 Hz, H-Rha-6 ),
00
5
.43 (1H, d, J ¼ 6.0 Hz, H-Glc-1 ).
þ
1
Compounds 6: C H O , pale yellow powder, ESI-MS m/z 369 [M þ Na] . H NMR
1
4 18 10
(
400 MHz, DMSO-d ) d (ppm): 7.45, 7.25 (each 1H, d, J ¼ 1.7 Hz, aromatic H), 4.85 (1H, d,
6
J ¼ 7.2 Hz, anomeric H), 3.85 (3H, s, -OMe).
3
.6. ABTS free radical-scavenging activities
zþ
The scavenging activity of the tested samples on ABTS radical was measured according to the
method as previously described (Chung et al. 2011). L-Ascorbic acid was used as the positive
zþ
zþ
control. Briefly, ABTS radical cation was prepared by mixing 10 mL of 2 mM ABTS water
solution with 100 mL of 70 mM potassium persulphate, and the mixture was allowed to stand in
the dark at room temperature for 12 h before use. Prior to the assay, the solution was diluted with
ethanol to give an absorbance at 734 nm of 0.70 ^ 0.02 in a 96-well flat-bottom microtitre plates
zþ
and was equilibrated at 258C. The ABTS solution (110 mL) was added to the sample solution
(total volume: 200 mL) and incubated at room temperature for 10 min, and the absorbance of AA
fractions (A ) were read at 734 nm. Measurements were performed at least in triplicate. The
i
zþ
blank absorbance (A ) was measured using ethanol. The ABTS radical cation solution was
0
zþ
prepared daily. The scavenging activity was expressed as percentage inhibition of the ABTS
radical cation and was determined by the following equation:
AAð%Þ ¼ ½1 2 ðAi=A0Þꢀ £ 100%:
zþ
The SC50 values (the concentration of sample required to scavenge 50% of ABTS radicals)
were obtained through extrapolation from linear regression analysis.
Supplementary material
Supplementary material relating to this article is available online, alongside Figures S1–S3.
Acknowledgements
This study was finally supported by the Main Direction Program of the Knowledge Innovation Project of
CAS (Grant No. KSCX2-EW-J-22) and the National Eleventh-Five Year Research Program of China
(
Grant No. 2011BAC09B04).
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