Two new oleanane-type triterpene saponins from the leaves of Schefflera sessiliflora de P. V.

Article abstract of DOI:10.1016/j.phytol.2014.11.020

From the leaves of Schefflera sessiliflora De P. V., two new oleanane-type triterpene saponins, named scheffleraside A (1), scheffleraside B (2); together with two known saponins, chikusetsusaponin IVa (3), 3-O-[α-l-rhamnopyranosyl-(1 → 3)]-β-d-glucuronopyranosyl hederagenin (4) were isolated by various chromatography methods. Its chemical structure was elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D experiments and comparison of their NMR data with previous reported data.

Full text of DOI:10.1016/j.phytol.2014.11.020

Phytochemistry Letters 11 (2015) 102–105
Contents lists available at ScienceDirect
Phytochemistry Letters
journal homepage: www.elsevier.com/locate/phytol
Two new oleanane-type triterpene saponins from the leaves
of Schefflera sessiliflora De P. V.
a,
b
a
a
Nguyen Tan Phat *, Le Thi Viet Hoa , Mai Dinh Tri , Le Tien Dung ,
a
a
Phan Nhat Minh , Bui Trong Dat
a
Institute of Chemical Technology, Vietnam Academy of Science and Technology, Ho Chi Minh City, Viet Nam
University of Technology, Vietnam National University, Ho Chi Minh City, Viet Nam
b
A R T I C L E I N F O
A B S T R A C T
Article history:
From the leaves of Schefflera sessiliflora De P. V., two new oleanane-type triterpene saponins, named
scheffleraside A (1), scheffleraside B (2); together with two known saponins, chikusetsusaponin IVa (3),
Received 30 September 2014
Received in revised form 20 November 2014
Accepted 27 November 2014
Available online 9 December 2014
3-O-[
a-
L-rhamnopyranosyl-(1 ! 3)]-
b-D-glucuronopyranosyl hederagenin (4) were isolated by various
chromatography methods. Its chemical structure was elucidated by IR, UV, HR-ESI-MS, NMR 1D and 2D
experiments and comparison of their NMR data with previous reported data.
ß 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
Keywords:
Schefflera sessiliflora De P. V.
Araliaceae
Scheffleraside A
Scheffleraside B
1
. Introduction
the isolation and structure elucidation of two new triterpene
saponins (1, 2) and 2 known saponins (3, 4) from S. sessiliflora De P.
Schefflera is a large genus of the Araliaceae family with over
V. growing in Vietnam.
6
50 species (Hebbar and Nalini, 2014), which 56 species are found
in Vietnam (La et al., 2013). Some species in the Schefflera genus,
such as Schefflera actinophylla, Schefflera arboricola, Schefflera
heptaphylla, Schefflera impressa, Schefflera leucantha, and Scheffler-
akwangsiensis have been chemically investigated, which led to the
isolation of triterpenoid (Wanas et al., 2010; Zhao et al., 2010; Wu
et al., 2013; Srivastava, 1992; Pancharoen et al., 1994; Wang et al.,
2
. Results and discussion
The 75% MeOH extract from the dried leaves of S. sessiliflora De
P. V. was subjected to column chromatography over silica gel
normal-phase and reversed-phase RP-18 to give two new
triterpene saponins named scheffleraside A (3-O-[
anosyl-( 1! 3)]- -glucuronopyranosyl oleanolic acid 28-O-[
rhamnopyranosyl-(1 ! 4)]- -glucopyranosyl ester) (1) and
scheffleraside B (3-O-[
-rhamnopyranosyl-(1 ! 3)]-
methyl)glucuronopyranosyl oleanolic acid 28-O-[ -rhamnopyr-
anosyl-(1 ! 4)]- -glucopyranosyl ester) (2), and two known
saponins: 3-O- -glucuronopyranosyl oleanolic acid 28-O-
glucopyranosyl ester (chikusetsusaponin IVa) (4) (Mizui et al.,
990), 3-O-[ -glucuronopyra-
-rhamnopyranosyl-(1 ! 3)]-
nosyl hederagenin (5) (El and Morta, 1998).
Compound (1) was obtained as a white amorphous powder. The
a-L-rhamnopyr-
2
014), sterol (Hansen and Boll, 1986), polyacetylene (Hansen and
Boll, 1986), phenolic (Li et al., 2005), antraquinone (Srivastava,
992), trisaccharide (Tran et al., 1991). Schefflera sessiliflora De P. V.
Araliaceae) is a new species in Viet Nam, it were discovered and
b
-D
a-L-
b
-D
1
(
0
b-D-(6 -O-
a-L
a
-L
indentified in 2004 (Nguyen et al., 2004). Pharmacological of
extracts from this species possessed antistress, enhanced physical
strength (Nguyen et al., 2004; Huynh et al., 2005); antioxidant
activities in DPPH and MDA test (Vo et al., 2008); the androgenic
effects (Tran et al., 2012). However, only two sapogenins: oleanolic
acid and hederagenin from the hydrolyzed product of total
saponins were isolated (Vo et al., 2003, 2004). This paper reports
b
-D
b-
D
b-D-
1
a-
L
b-D
molecular formula was established as C54
H
86
O
22 by HR-ESI-MS
ꢀ
+
data ([MꢀH] m/z: 1085.5521, calcd. 1085.5527 and [M+Na] m/z
1109.5533, calcd. 1109.5503). The IR spectrum of 1 showed
ꢀ1
ꢀ1
absorptions of hydroxyl (3418 cm ) and carbonyl (1726 cm )
groups. The C NMR and DEPT spectrum (Table 1), showed 1 has
*
Corresponding author. Tel.: +84 916 360 751; fax: +84 838293889.
1
3
E-mail addresses: phat_nguyentan88@yahoo.com, ntphat@ict.vast.vn
(N.T. Phat).
fifty four carbons including: one carbonyl carbon, two olefinic
http://dx.doi.org/10.1016/j.phytol.2014.11.020
874-3900/ß 2014 Phytochemical Society of Europe. Published by Elsevier B.V. All rights reserved.
1

N.T. Phat et al. / Phytochemistry Letters 11 (2015) 102–105
103
Table 1
1
13
5
H (500 Hz) and C (125 Hz) NMR spectral data for compounds 1 and 2 in pyridine-d .
Aglycone
1
2
Sugar
GlcA
1
2
d
H
d
C
d
H
d
C
d
H
d
C
d
H
d
C
1
2
3
4
5
6
7
8
9
0.77, 1.30
1.74, 2.24
3.26 br d (7.5)
–
38.6
26.4
89.1
39.4
55.6
18.4
33.1
39.8
47.9
36.8
23.7
0.78, 1.28
38.6
26.4
89.3
39.5
55.7
18.4
33.1
39.9
48.0
36.9
23.7
0
1.72, 2.04
1
4.78 d (6.5)
4.00
106.8
75.9
82.1
72.0
4.86 d (7.5)
4.03
107.0
75.7
82.0
71.4
77.1
170.7
52.1
0
3.26 dd (4.0, 11.5)
2
0
–
3
4.37
4.39
0
0.69
0.72
4
4.28
4.39
0
1.21, 1.40
1.30, 1.40
–
1.20, 1.41
1.28, 1.41
–
5
0
4.37
76.9
4.48
a
6
0
6 -OMe
3.76 s
1.53
1.56
Rha I
0
0
0
0
0
0
0
0
0
0
0
0
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
–
–
1
2
3
4
5
6
6.28 br s
4.71 br s
4.56 d (8.0)
4.28
102.5
72.5
72.6
74.1
69.6
18.6
6.28 br s
4.73 d (1.5)
4.54
102.9
72.5
72.7
74.1
69.8
18.6
1.81
1.83
5.38 br s
–
122.9
144.1
42.0
28.2
23.3
47.0
41.7
46.1
30.7
34.0
32.5
28.1
16.9
15.4
17.4
26.0
176.4
33.1
23.6
5.38 br s
–
122.9
144.1
42.1
28.2
23.3
47.0
41.7
46.1
30.7
34.0
32.5
28.0
16.8
15.5
17.4
26.1
176.4
33.1
23.6
4.32
–
–
5.06
5.06
1.14, 1.30
1.89, 2.05
–
1.14, 1.26
1.90, 2.04
–
1.68 d (5.0)
1.68 d (6.5)
Glc-28
0
0
0
0
0
0
00
00
00
00
00
00
1
2
3
4
5
6
6.18 d (8.0)
4.10
95.3
74.2
77.0
77.8
77.8
60.9
6.20 d (8.0)
4.12
95.4
74.2
77.1
77.9
77.9
61.0
3.14 br d (10.0)
1.21, 1.74
–
3.16 br d (13.0)
1.20, 1.72
–
4.18
4.20
4.47
4.52
1.03, 1.30
1.68, 1.74
1.21 s
0.92 s
0.77 s
1.03 s
1.24 s
–
1.04, 1.28
1.72, 1.72
1.21 s
0.91 s
0.78 s
1.04 s
1.24 s
–
3.76 d (9.5)
4.04, 4.18
3.78 d (9.5)
4.05, 4.20
Rha II
0
0
0
0
0
0
000
000
000
000
000
000
1
2
3
4
5
6
5.85 br s
4.63 br s
4.47
102.6
72.5
72.7
73.8
70.3
18.4
5.87 br s
4.64 d (1.5)
4.52
102.7
72.5
72.7
73.9
70.4
18.5
4.28
4.32
4.86
4.90
0.89 s
0.86 s
0.90 s
0.87 s
1.65 d (6.0)
1.66 d (6.5)
a
Not determined.
000
C
d 77.8 (C-4 ) of Glc; between oxygenated methine
carbons, four anomeric carbons, seventeen oxygenated methine
carbons, one oxygenated methylene carbon, six quaternary
carbons, three methine carbons, ten methylene carbons, and nine
methyl carbons. The presence of seven tertiary methyl groups, two
with carbon at
0000
C
proton at 4.47 (m, H-4 ) and carbon acetal at d 102.6 (C-1 ).
0
00
d
H
These connectivities were also confirmed by correlations observed
0
in the NOESY spectrum between H-3 (
d
H
3.26) of aglycone and H-1
00
0
olefinic carbons at
d
C
144.0 (C-13) and 122.8 (C-12), and one
(d
H
4.78) of GlcA; between H-1 (
d
H
6.28) of RhaI and H-3 (
d
H
4.37)
carbonyl carbon 176.4 (C-28) which indicated an olean-12-en-28-
oic acid as an aglycone (Tran et al., 1991). Thus 1 was an oleanane-
type triterpenoid saponin bearing four sugar (six carbons) units.
of GlcA. Based on data of HR-ESI-MS, 1D, 2D-NMR and compared
with previous published data (Tapondjou et al., 2006; Wang et al.,
2014), the structure of 1 was identified as 3-O-[a-L-rhamnopyr-
1
The H NMR data (Table 1) also indicated aglycone of 1 was
anosyl-(1 ! 3)]-
b
-
D
-glucuronopyranosyl oleanolic acid 28-O-[a-L-
oleanolic acid with: one olefinic proton at
d
H
5.38 (br s, H-12); one
rhamnopyranosyl-(1 ! 4)]-
b-D-glucopyranosyl ester, and named
oxygenated methine proton at 3.26 (br d, 7.5, H-3); one methine
d
H
scheffleraside A.
proton at
groups at
anomeric protons at
d
d
H
3.14 (br d, 10.0, H-18) and seven tertiary methyl
0.76–1.24 (Maeda et al., 1994). Moreover, four
Compound (2) was obtained as a white amorphous powder. The
molecular formula was established as C55 22 by HR-ESI-MS data
([M+Na] m/z 1123.5633, calcd. 1123.5659). The H and C NMR
data (Table 1) demonstrated that 2 has the same aglycone and sugar
H
88
H O
0
000
+
1
13
d
H
4.78 (d, 6.5, H-1 ); 6.18 (d, 8.0, H-1 ); 6.28
0
0
0000
(
(
br s, H-1 ); 5.85 (br s H-1 ) to four anomeric carbons at
d
C
106.8
0
000
00
0000
C-1 ), 95.3 (C-1 ), 102.5 (C-1 ), 102.6 (C-1 ) were assigned to
b
-
chains as 1, except for presence of an oxygenated methyl group [
3.76 (s); 52.1]. Further, the HMBC spectrum (Fig. 1) showed
correlation between thisoxygenatedmethylat 3.76(s)andcarbon
carbonyl of glucuronic unit at 170.7. Based on data of HR-ESI-MS,
d
H
D
-glucuronic (GlcA), -glucose (Glc) and two -rhamnose (Rha)
b
-D
a
-L
d
C
units, respectively. It was completely appropriated with HR-ESI-
d
H
+
MS data, a peak [M+2NaꢀH] m/z 1131.5492 was indicated the
d
C
presence of a sugar acid (Madl et al., 2006). The COSY, HSQC and
NOESY spectrum, allowed analysis of their spin systems and
assigned of their proton resonances to determine clearly every
sugar unit. Beside, through acid hydrolysis followed by co-TLC in
comparison with standard sugars the identification of the sugars
was determined to be D for Glc, GlcA and L for Rha (see Section 3).
1D, 2D-NMR and compared with previous published data (Tapond-
jou etal., 2006; Wang et al., 2014), the structure of2 was identified as
0
3-O-[
pyranosyl oleanolic acid 28-O-[
glucopyranosyl ester, and named scheffleraside B.
a
-
L
-rhamnopyranosyl-(1 ! 3)]-
b
-
D
-(6 -O-methyl)glucurono-
a-L
-rhamnopyranosyl-(1 ! 4)]-
b-D-
Some species in the Schefflera genus, such as S. actinophylla
(Wanas et al., 2010), S. arboricola (Zhao et al., 2010), S. impressa
(Srivastava, 1992), S. leucantha (Pancharoen et al., 1994) are
reported as a rich source of saponins which possessed lupane-type
and/or ursane-type aglycones. Whereas, the genins of S. hepta-
phylla (Maeda et al., 1994), S. kwangsiensis (Wang et al., 2014) as
well as S. sessiliflora were oleanolic acid and hederagenin. However,
all compounds were isolated for the first time from the genus
Schefflera.
The HMBC spectrum (Fig. 1), showed correlations between
anomeric proton at
0
d
H
4.78 (d, 6.5, H-1 ) of GlcA and carbons at
C H
d 89.1 (C-3) of aglycone; between anomeric proton at d 6.28 (br s,
00
0
0
H-1 ) of Rha I unit and carbons at
oxygenated methine proton at
d
C
82.1 (C-3 ) of GlcA; between
d
H
4.37 (m, H-3 ) and carbon acetal
0
0
at
d
C
102.5 (C-1 ). On the other hands, anomeric proton at
d
H
6.18
176.4 (C-
H
8); anomeric proton at d 5.85 (br s, H-1 ) of Rha II correlated
000
(
d, 8.0, H-1 ) of Glc correlated with carbonyl carbon at d
C
0
000
2

1
04
N.T. Phat et al. / Phytochemistry Letters 11 (2015) 102–105
Fig. 1. Chemical structures and selected HMBC, COSY and NOESY correlations of 1 and 2.
3
. Experimental
seven subfractions (IV.1–IV.7). Fraction IV.2 (15 g), was eluted with
solvent system CHCl –MeOH–H
O (85:15:0.1 ! 75:25:0.3, v/v),
then, separated by RP-18 using gradient mixtures of MeOH–H
gave 3 (15 mg) and 4 (8 mg). Similar, Fraction IV.3 (20 g) was eluted
with solvent system CHCl –MeOH–H
O (80:20:0.2 ! 70:30:0.5,
v/v), then, separated by RP-18 using gradient mixtures of MeOH–
O gave 1 (12 mg) and 2 (16 mg).
3
2
3.1. General experimental procedures
2
O
The high resolution electrospray ionization mass spectroscopy
3
2
(HR-ESI-MS) was recorded on a Bruker MicrOTOF-QII spectrome-
1
13
ter. The H NMR (500 MHz), C NMR (125 MHz), DEPT, COSY,
HSQC and HMBC spectra were recorded on a Bruker AM500 FT-
NMR spectrometer using tetramethylsilane (TMS) as internal
standard. Column chromatography was carried out using Merck
Silica gel normal-phase (230–240 mesh) and reversed-phase C18
H
2
3.3.1. Scheffleraside A (1)
2
D
5
Amorphous powder (MeOH); ½
a
ꢁ
ꢀ17.0 (c 0.10, MeOH); IR
ꢀ1
(KBr) ymax: 3418, 2927, 1726, 1615, 1075, 1030 cm ; UV (MeOH)
ꢀ
(
Merck). Analytical TLC was carried out in silica gel plates (Merck
DC-Alufolien 60 F254). Compounds were visualized by spraying
with aqueous 10% H SO and heating for 3–5 min.
l
max: 206 and 220 nm; HR-ESI-MS m/z 1085.5521 [MꢀH] (calcd
+
for C54
H
O
85
O
22, 1085.5527) and m/z 1109.5533 [M+Na] (calcd for
1
13
2
4
C
54
H
86
22Na, 1109.5503); H and C NMR data (pyridine-d
5
), see
Table 1.
3.2. Plant material
3
.3.2. Scheffleraside B (2)
Amorphous powder (MeOH); ½
2
D
5
The leaves of S. sessiliflora De P. V. were provided by Center
a
ꢁ
ꢀ13.5 (c 0.10, MeOH); IR
ꢀ1
Cultivation and Processing of Medicinal Plants Da Lat, No. 18 Hoang
Van Thu Street, Da Lat City, Viet Nam and identified by Dr. Phan
Van De – Department of Medicinal Resources, The Research Center
of Ginseng and Medicinal Materials, Ho Chi Minh City, Viet Nam. A
voucher specimen was deposited in Bioactive Compounds
Laboratory, Institute of Chemical Technology, Vietnam Academy
of Science and Technology, Viet Nam.
(KBr) ymax: 3423, 2924, 1741, 1635, 1067, 1039 cm ; UV (MeOH)
l
C H O22Na, 1123.5659; H and C NMR data (pyridine-d ), see
58 88 5
+
max: 240 nm; HR-ESI-MS m/z 1123.5633 [M+Na] , calcd for
1
13
Table 1.
3.4. Acid hydrolysis
The leaves were collected, washed, dried, and powdered.
3
Each saponin (2 mg) was refluxed with 2 N aq. CH COOH (5 ml)
for 2 h at 100 8C. After extraction with CH
layer was repeatedly evaporated to dryness with MeOH until
neutral, and then analyzed by TLC over silica gel (MeCOEt–isoPrOH–
3
Cl (3ꢂ 5 ml), the aqueous
3.3. Extraction and isolation
Powder of leaves S. sessiliflora De P. V. (5 kg) were extracted with
Me
2
CO–H
2
O 20:10:7:6) by comparison with authentic samples (
L-
9
6% EtOH (v/v), filtered residue, removed solvents under low
rhamnose Rf 0.65;
D
-glucose Rf 0.40; -glucuronic acid Rf 0.05)
D
pressure, obtained crude extract (890 g). Then, crude extract was
added water and extracted with n-hexane, ethyl acetate, obtained
extracts respectively. The aqueous portion was eluted by Diaion HP-
(Haddad et al., 2013; Voutquenne-Nazabadioko et al., 2013).
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respectively. Fraction IV (80 g) was subjected by column chroma-
tography with mobile phase (EtOAc–MeOH) gradient (0–100%) gave

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