Chevalierinoside B and C: Two new isoflavonoid glycosides from the stem bark of Antidesma laciniatum Muell. Arg (syn. Antidesma chevalieri Beille)

Article abstract of DOI:10.1016/j.phytol.2014.05.013

Chevalierinosides B (1) and C (2), two new isoflavonoid glycosides, characterized as biochanin A 7-O-[β-d-apiofuranosyl-(1→2)-β-d- glucopyranoside] and genistein 7-O-[β-d-apiofuranosyl-(1→2)-β-d- glucopyranoside], together with the known isoflavonoids, chevalierinoside A (3) and genistein 7-O-β-d-glucopyranoside (4), kaempferol 3-O-β-d- glucopyranoside (5) and triterpenes, friedelin (6), betulinic acid (7), 30-oxobetulinic acid (8), 30-hydroxybetulinic acid (9), were isolated from the stem bark of Antidesma laciniatum Muell. Arg. (syn. Antidesma chevalieri Beille). Their structures were established by direct interpretation of their spectral data, mainly HR-TOFESIMS, 1D-NMR (¹H, ¹³C and DEPT) and 2D-NMR (COSY, NOESY, TOCSY, HSQC and HMBC), and by comparison with the literature.

Full text of DOI:10.1016/j.phytol.2014.05.013

G Model
PHYTOL 719 1–4
Phytochemistry Letters xxx (2014) xxx–xxx
Contents lists available at ScienceDirect
Phytochemistry Letters
journal homepage: www.elsevier.com/locate/phytol
1
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Chevalierinoside B and C: Two new isoflavonoid glycosides from the
stem bark of Antidesma laciniatum Muell. Arg (syn. Antidesma chevalieri
Beille)
a
a
a
` ´
Q1 Marie Genevieve Djouossi , Florence Declaire Mabou , Perrin Lanversin Foning Tebou ,
5
6
7
David Ngnokam a, , Leon A. Tapondjou , Dominique Harakat ,
a
b
*
Laurence Voutquenne-Nazabadioko c
8
9
10
a Faculty of Science, Department of Chemistry, University of Dschang, P.O. Box 67, Dschang, Cameroon
b Service Commun d’Analyses, Institut de Chimie Mole´culaire de Reims (ICMR), CNRS UMR 7312, Bat. 18 B.P. 1039, 51687 Reims Cedex 2, France
c Groupe Isolement et Structure, Institut de Chimie Mole´culaire de Reims (ICMR), CNRS UMR 7312, Bat. 18 B.P. 1039, 51687 Reims Cedex 2, France
A R T I C L E I N F O
A B S T R A C T
Article history:
Chevalierinosides B (1) and C (2), two new isoflavonoid glycosides, characterized as biochanin A 7-O-[b-
Received 27 February 2014
Received in revised form 18 April 2014
Accepted 27 May 2014
Available online xxx
D
-apiofuranosyl-(1!2)-
pyranoside], together with the known isoflavonoids, chevalierinoside A (3) and genistein 7-O-
glucopyranoside (4), kaempferol 3-O- -glucopyranoside (5) and triterpenes, friedelin (6), betulinic
b
-
D
-glucopyranoside] and genistein 7-O-[
b
-
D
-apiofuranosyl-(1!2)-
b-D-gluco-
b-D-
b-D
acid (7), 30-oxobetulinic acid (8), 30-hydroxybetulinic acid (9), were isolated from the stem bark of
Antidesma laciniatum Muell. Arg. (syn. Antidesma chevalieri Beille). Their structures were established by
direct interpretation of their spectral data, mainly HR-TOFESIMS, 1D-NMR (1H, 13C and DEPT) and 2D-
NMR (COSY, NOESY, TOCSY, HSQC and HMBC), and by comparison with the literature.
ß 2014 Published by Elsevier B.V. on behalf of Phytochemical Society of Europe.
Keywords:
Antidesma laciniatum/Antidesma chevalieri
Phyllantaceae
Isoflavonoid glycosides
Chevalierinosides
Triterpene
Structure elucidation
11
12
1. Introduction
laciniatum Muell. Arg. (syn. Antidesma chevalieri Beille), used in 28
Africa to prevent miscarriage and to treat intestinal complaints 29
13
14
15
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21
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23
24
25
26
27
Isoflavonoids represent a group of secondary metabolites
widely distributed in higher plants. They often occurred in plants
as glycosides in which one or more of the phenolic hydroxyl groups
or aromatic carbons are combined with sugar residues (Mackova
et al., 2006; Veitch, 2007; Botta et al., 2009; Yao-Kouassi et al.,
2008; Farag et al., 2001; Wang et al., 2006; Tang et al., 2008).
Isoflavonoids have attracted considerable interest because of a
large variety of biological activities, such as antioxidant
(Komiyama et al., 1989; Harper et al., 1999), antiplasmodial
(Yenesew et al., 2003; Kraft et al., 2000), cytotoxic (Cottiglia et al.,
2005; Nkengfack et al., 2001), anti-inflammatory (Laupattaraka-
sem et al., 2004; Rahman et al., 2003) and antimicrobial (Sato et al.,
2003; Redko et al., 2007). Recently, we reported the isolation of one
new isoflavonoid glycoside named chevalierinoside A (Djouossi
et al., 2014), from the stem bark of a small tree, Antidesma
(Schmelzer, 2008). During phytochemical investigation of the 30
methanol extract of the stem bark of this small tree (Phyllanta- 31
ceae), we found some minor compounds that were difficult to 32
separate due to the small quantity of the extract. As an extension of 33
our previous work, we now report the isolation of two new 34
isoflavonoid glycosides, chevalierinosides B (1) and C (2), together 35
with the known chevalierinoside
A
(3), genistein 7-O-
b
-D
-
36
glucopyranoside (4), kaempferol 3-O-
b
-D
-glucopyranoside (5), 37
friedelin (6), betulinic acid (7), 30-oxobetulinic acid (8), 30- 38
hydroxybetulinic acid (9), from the methanol extract of the stem 39
bark of the same highest and oldest species, founded in the same 40
Region during another fieldtrip collection.
41
2. Results and discussion
42
Compound 1 was obtained as a yellowish gum. Its molecular 43
formula C27H30O14 was determined on the basis of its HR- 44
TOFESIMS spectrum exhibiting a pseudo-molecular ion peak at 45
m/z 601.1537 [M+Na]+ (calcd. 601.1533) and confirmed by 13C 46
*
Corresponding author. Tel.: +237 96932925.
E-mail address: dngnokam@yahoo.fr (D. Ngnokam).
http://dx.doi.org/10.1016/j.phytol.2014.05.013
1874-3900/ß 2014 Published by Elsevier B.V. on behalf of Phytochemical Society of Europe.
Please cite this article in press as: Djouossi, M.G., et al., Chevalierinoside B and C: Two new isoflavonoid glycosides from the stem bark of
Antidesma laciniatum Muell. Arg (syn. Antidesma chevalieri Beille). Phytochem. Lett. (2014), http://dx.doi.org/10.1016/j.phy-
tol.2014.05.013

G Model
PHYTOL 719 1–4
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M.G. Djouossi et al. / Phytochemistry Letters xxx (2014) xxx–xxx
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NMR and DEPT analysis. This was in accord with an isoflavone
having one hydroxyl, one methoxyl, and one pentosyl-hexosyl
substitutions. The IR spectrum showed absorption bands for
hydroxyl (3500–3200 cmꢀ1), carbonyl (1656 cmꢀ1) and aromatic
(1614 and 1581 cmꢀ1) functionalities. The NMR spectral data for
the aglycon moiety were in agreement with those of 5,7-
dihydroxy -40-methoxyisoflavone (biochanin A) (Santos et al.,
identification of one terminal
b
-apiofuranosyl (Api) and one
79
80
81
82
83
84
85
86
87
88
89
90
91
92
93
94
inner -glucopyranosyl (Glc) units. The D-configuration for
b
glucose and apiose was suggested by comparison of the NMR
data of 1 with those of chevalierinoside A (3) (Djouossi et al.,
2014), and, was confirmed by GC –MS after derivatization.
The HMBC spectrum correlations between H-1 (
and C-7 ( 163.3) of the aglycon indicated that Glc was linked at C-7
of the aglycon. Furthermore, the HMBC correlation between H-1 (
5.48) of Api and C-2 ( 77.3) of Glc established the connectivity
d
5.16) of Glc
d
1995). The 1H NMR spectrum of 1 exhibited signals at
d
8.20 (H-2,
d
s), 6.71 (H-8, d, J = 2.3 Hz), 6.52 (H-6, d, J = 2.3 Hz), 7.52 (H -20/H-
60, d, J = 8.9 Hz) and 7.02 (H -30/H-50, d, J = 8.9 Hz) indicative of
substitutions on carbons 5, 7 and 40 of the isoflavone. The signal
d
between Api and Glc. This was supported in comparison between
13C data of 1 with those of eriosemaside C (Ma et al., 1999)
possessing the same glycosidic linkage and lanceolarin (Rao et al.,
1989) possessing the apiose unit linked in position 6 of the glucose
unit. Therefore, the oligosaccharide at C-7 of the aglycon was
at
d
3.86 (s) correlated to the 13C NMR signal at
d
159.7 in the
HMBC spectrum (Table 1), confirming that the methoxyl group
was located at C -40 in biochanin A as observed with chevalierino-
side A (3) (Djouossi et al., 2014) and lanceolarin (Rao et al., 1989)
and not at C-5 as in eriosemaside C (Ma et al., 1999). After acid
hydrolysis of 1, only two sugar units, glucose and apiose were
detected by TLC while the aglycon was also identified to
biochanin A as previously described (Djouossi et al., 2014;
Santos et al., 1995). The difference between chevalierinoside A
(3) and 1 was the absence of the rhamnosyl moiety in 1. This was
supported by the 1H NMR spectrum of 1 which displayed only
established as O-[
On the basis of the above evidences, the structure of compound 1
was determined as biochanin A 7-O-[
-apiofuranosyl-(1!2)-
-glucopyranoside], a new isoflavonoid glycoside named cheva-
lierinoside B.
b
-D
-apiofuranosyl-(1!2)-
b-
D-glucopyranoside].
b
-D
b
-
95
96
97
98
D
Compound 2, a yellowish gum, had a pseudo-molecular ion
peak at m /z 587.1379 [M+Na]+ (calcd. for C26H28O14Na,
587.1377) in the HR-TOFESIMS, one methyl fewer than com-
pound 1. Comparison of their NMR spectroscopic data revealed
that 2 differed only in ring B of the aglycon moiety. The shielding
99
100
101
102
103
104
105
106
107
108
109
110
two sugar anomeric protons at
J = 1.7 Hz) giving correlations with two anomeric carbon at
and 109.5 respectively in the HSQC spectrum (Table 1). The
chemical shift of the terminal oxymethylene carbon (C-6; 61.0)
d
5.16 (d, J = 7.5 Hz) and 5.48 (d,
d
98.8
of C -40 ( 157.5) and H-30/H-50 (
C -30/C-50
(d 114.9) indicated the absence of methyl on the
d
d 6.88), and the deshielding of
d
of the glucopyranosyl moiety also confirmed the absence of
substitution at this position (Djouossi et al., 2014). Complete
assignments of each sugar proton system were achieved by
analysis of 1H –1H COSY, TOCSY and NOESY spectra while
carbons were assigned from HSQC and HMBC spectra. Evaluation
of the spin-spin couplings and chemical shifts allowed the
hydroxyl at C -40 (Table 1). These NMR spectral data were in
agreement with those of 5,7,40-trihydroxyisoflavone (genistein)
( Chaturvedula and Prakash, 2013). Acid hydrolysis of 2 also
afforded apiose and glucose, detected by TLC, analysis of 1D- and
2D-NMR spectral data of 2 permitted the identification of one
terminal
b-apiofuranosyl (Api) and one inner b-glucopyranosyl
Table 1
1H (600 MHz) DEPT and 13C (150 MHz) NMR data of compounds 1 and 2 in CD3OD, and some HMBC correlations of 1 and 2.
No
1
2
HMBC (H ! C)
dC
dH (mult; J)
dC
dH (mult; J)
2
154.1
123.1
181.1
162.0
99.6
8.20 (s)
153.9
123.7
181.8
162.2
99.5
8.17 (s)
3, 4, 9, 10
3
4
5
6
6.52 (d, 2.3)
6.71 (d, 2.3)
6.52 (d, 2.2)
6.71 (d, 2.2)
5, 7, 8, 10
6, 7, 9, 10
7
163.3
94.4
163.2
94.4
8
9
157.9
107.0
122.9
130.0
113.5
159.7
113.5
130.0
54.3
157.9
106.6
121.9
130.0
114.9
157.5
114.9
130.0
10
10
20
7.52 (d, 8.9)
7.02 (d, 8.9)
7.42 (d, 8.8)
6.88 (d, 8.8)
3, 40
10, 40, 50
30
40
50
7.02 (d, 8.9)
7.52 (d, 8.9)
3.86 (s)
6.88 (d, 8.8)
7.42 (d, 8.8)
–
10, 40
3, 40
40
60
40-OMe
Glc
1
98.8
77.3
77.0
69.8
76.9
61.0
5.16 (d, 7.5)
98.8
77.3
77.0
69.8
76.9
61.0
5.16 (d, 7.5)
7, Glc-3
2
3.70 (dd, 8.8, 7.5)
3.65 (t, 8.8)
3.69 (dd, 9.2, 7.5)
3.65 (t, 9.2)
Glc-1, Api-1
Glc-2, Glc-4
Glc-5, Glc-6
3
4
3.43 (dd, 9.6, 8.8)
3.52 (m)
3.43 (t, 9.3)
5
3.53 (m)
6
3.73 (dd, 12.3, 5.9)
3.92 (dd, 12.3, 2.2)
3.73 (dd, 12.2, 5.8)
3.92 (dd, 12.2, 2.2)
Glc-4
Glc-4
Api
1
109.5
76.7
79.3
74.0
5.48 (d, 1.7)
3.97 (d, 1.7)
109.5
76.7
79.3
74.0
5.47 (d, 1.7)
3.97 (d, 1.7)
Api-3, Api-4, Glc-2
Api-5
2
3
4
3.83 (d, 9.6)
4.04 (d, 9.6)
3.56 (s)
3.83 (d, 9.6)
4.04 (d, 9.6)
3.55 (s)
Api-1, Api-2, Api-3, Api5
Api-2, Api-3, Api4
5
64.4
64.4
Please cite this article in press as: Djouossi, M.G., et al., Chevalierinoside B and C: Two new isoflavonoid glycosides from the stem bark of
Antidesma laciniatum Muell. Arg (syn. Antidesma chevalieri Beille). Phytochem. Lett. (2014), http://dx.doi.org/10.1016/j.phy-
tol.2014.05.013

G Model
PHYTOL 719 1–4
M.G. Djouossi et al. / Phytochemistry Letters xxx (2014) xxx–xxx
3
111
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(Glc) units, as in 1. The D-configuration for glucose and apiose
was determined by GC –MS after derivatization. The HMBC
purified on silica gel CC eluted with n-hexane-EtOAc (19:1 and 9:1) 170
and 32 fractions (25 mL each) were collected. Re-crystallization of 171
fractions [12–24] gave friedelin (6) (34.5 mg). Fraction F2 was 172
purified on silica gel CC eluted with n-hexane-EtOAc (4:1, 3:2 and 173
1:1) and 33 sub-fractions (25 mL each) were collected. Re- 174
crystallization of fractions [5–11], [16–20] and [25–29] afford 175
betulinic acid (7) (52 mg), 30-oxobetulinic acid (8) (12 mg) and 30- 176
hydroxybetulinic acid (9) (10.5 mg), respectively. Fractions F3 and 177
F4 were respectively passed through sephadex LH-20 CC eluted 178
with methanol. 42 fractions of 10 mL each were collected from F3 179
and 37 others from F4. Fractions [23–40] from F3 (3 g) and [10–25] 180
from F4 (2.5 g) were combined and passed through silica gel CC 181
eluted with EtOAc-MeOH (1:0, 19:1 and 9:1). 46 fractions (50 mL 182
each), were collected and combined on the basis of their TLC 183
profiles. The fractions [1–13] (1.2 g), [14–21] (0.7 g) and [22–46] 184
(1.3 g) were purified separately through sephadex LH-20, eluted 185
correlation between H-1 (
aglycon and H-1 ( 5.47) of Api and C-2 (
the same diglycloside moity as in 1. Thus, compound 2 was
established as genistein 7-O-[ -glu-
-apiofuranosyl-(1!2)-
copyranoside], named chevalierinoside C.
d
5.16) of Glc and C-7 (
d 163.2) of the
d
d
77.3) of Glc, confirmed
b
-
D
b-D
Structures of known compounds were determined as two
isoflavonoids, one flavonoid and four triterpenes by means of Co-
TLC, and by comparative analysis of their physical and spectral data
with those reported in the literature for chevalierinoside A (3)
(Djouossi et al., 2014), genistein 7-O-
b
-
D-glucopyranoside (4)
(Fedoreyev et al., 2008), kaempferol 3-O-
b
-D-glucopyranoside (5)
(Shahat et al., 2005), friedelin (6) (Chandler and Hooper, 1979),
betulinic acid (7) (Sholichin et al., 1980), 30-oxobetulinic acid (8)
(Macias et al., 1998) and 30-hydroxybetulinic acid (9) (Mayer,
1996).
with methanol, yielding genistein 7-O-
(12 mg) and kaempferol 3-O- -glucopyranoside (5) (6 mg) from 187
[1–13], compounds 1 (15 mg) and 2 (17 mg) from [14–21], and 188
chevalierinoside (3) (29 mg) from [22–46]. Attempts of 189
b-D-glucopyranoside (4) 186
b-D
128
129
3. Experimental
A
3.1. General experimental procedures
purification of fraction F5 failed.
3.4. New compounds information
Chevalierinoside B (1): yellowish gum; [
190
130
131
132
133
134
135
136
137
138
139
140
141
142
143
144
145
146
147
148
149
150
151
Optical rotations were measured on a Perkin-Elmer 341
polarimeter. 1H and 13C NMR spectra were recorded on a Bruker
Avance III 600 spectrometer equipped with a cryoplatform (1H at
600 MHz and 13C at 150 MHz). 2D-NMR experiments were
performed using standard Bruker microprograms (Xwin-NMR
191
23
a
]
D
ꢀ49.5 (c = 3.3, 192
MeOH); IR (NaCl) nmax (cmꢀ1): 3500–3200 (OH); 2925; 1656 (C– 193
O), 1614, 1581 (aromatic); 1440; 1290; 1249; 1180; 1068; 1H and 194
13C NMR data, see Table 1; HR-TOFESIMS m/z: 601.1537 [M+Na]+ 195
version 2.1 software). Chemical shifts (
million (ppm) with the solvent signals as reference relative to
TMS ( = 0) as internal standard, while the coupling constants (J
d) are reported in parts per
(calcd. for C27H30O14Na, 601.1533).
196
23
d
Chevalierinoside C (2): yellowish gum; [
a
]
D
ꢀ36.0 (c = 0.50, 197
values) are given in Hertz (Hz). The IR spectra were recorded with
a Shimadzu FT-IR-8400S spectrophotometer. UV spectra were
MeOH); IR (NaCl) nmax (cmꢀ1): 3500–3200 (OH); 2920; 1656 (C– 198
O), 1612, 1575 (aromatic); 1251; 1180; 1072; 1H and 13C NMR 199
data, see Table 1; HR-TOFESIMS m/z: 587.1379 [M+Na]+ (calcd. for 200
determined as methanol solution with
a Cary 50 UV/VIS
Spectrophotometer. HR-TOFESIMS experiments were performed
using a Micromass Q-TOF micro instrument (Manchester, UK)
with an electrospray source. The samples were introduced by
C26H28O14Na, 587.1377).
201
3.5. Acid hydrolysis and GC–MS analysis of 1 and 2
202
direct infusion in a solution of MeOH at a rate of 5
m
L minꢀ1. GC –
MS experiments were carried out on an MD 800 instrument.
Column chromatography (CC) was performed on silica gel 60
(70–230 mesh, Merck) and gel permeation on Sephadex LH-20
while TLC was carried out on silica gel GF254 pre-coated plates
with detection accomplished by spraying with 50% H2SO4
followed by heating at 100 8C, or by visualizing with an UV
lamp at 254 and 365 nm.
Each of compound 1 (10 mg) and 2 (10 mg) was respectively 203
dissolved in MeOH-2N HCl (1:4) (10 mL) and refluxed at 80 8C for 204
3 h. After removal of MeOH under reduced pressure, the aqueous 205
layer was extracted with CH2Cl2 (3ꢁ 5 mL). The combined CH2Cl2 206
extracts were washed with H2O and evaporated to dryness to 207
afford biochanin A (1.5 mg) (Santos et al., 1995) from 1, and 208
genistein (2 mg) (Chaturvedula and Prakash, 2013) from 2. Each 209
aqueous layer was neutralized by dilute NaOH. The sugar 210
components were analyzed by co-TLC with the mixture CHCl3/ 211
MeOH/H2O (70:30:2). After spraying, apiose gave a weak yellow 212
152
3.2. Plant material
153
154
155
156
157
158
The stem bark of Antidesma laciniatum Muell. Arg. (syn.
Antidesma chevalieri Beille) was collected at Bansoa, Menoua
Division, West Region of Cameroon, in January 2013. Authentica-
tion was done by Mr Victor Nana, a botanist of the Cameroon
spot at Rf 0.79, and glucose gave a blue spot at Rf 0.71.
213
Each previous aqueous layer was concentrated to dryness. The 214
residue obtained was dissolved in pyridine (1 mL), then 215
(CH3)3SiNHSi(CH3)3 (1 mL) was added. After 10 min at room 216
temperature, the solution was blown to dryness with a stream of 217
nitrogen. The residue was dissolved in diethyl ether then subjected 218
´
National Herbarium, Yaounde, where the voucher specimen (No.
9667/SRF/Cam) is deposited.
to GC–MS analysis.
219
159
3.3. Extraction and isolation
Trimethylsilyl ether derivatives were separated using an HP Ac- 220
5 capillary column (0.25 m ꢁ 30 m). Nitrogen was used as the 221
carrier gas. The initial column oven temperature was 180 8C, then 222
increased at 5 8C minꢀ1 to a final value of 240 8C. The sugars were 223
determined by comparison of retention times (tR) with standard 224
160
161
162
163
164
165
166
167
168
169
The dried and powdered plant material (7 kg) was extracted by
percolation with methanol (3ꢁ 15 L, 72 h) at room temperature
affording 120 g of crude extract after evaporation of the solvent
under vacuum.
A portion (90 g) of this extract was subjected to silica gel
column chromatography (CC) eluting with gradient mixtures of n-
hexane-EtOAc (1:0, 9:1, 4:1, 7:3, 1:1, 3:7 and 0:1) followed by
EtOAc-MeOH (19:1, 9:1, 17:3, 4:1, 1:1 and 0:1). 57 fractions, each
300 mL, were collected and combined on the basis of their TLC
profiles to give five fractions noted F1 to F5. Fraction F1 was
sugars: tR (min) Glc 6.86, Api 2.78.
225
Acknowledgments
226
´
The authors are grateful to Conseil Regional Champagne Q23227
´
´
Ardenne, Conseil General de la Marne and EU-programme FEDER 228
to the PlANET CPER project. 229
Please cite this article in press as: Djouossi, M.G., et al., Chevalierinoside B and C: Two new isoflavonoid glycosides from the stem bark of
Antidesma laciniatum Muell. Arg (syn. Antidesma chevalieri Beille). Phytochem. Lett. (2014), http://dx.doi.org/10.1016/j.phy-
tol.2014.05.013

G Model
PHYTOL 719 1–4
4
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Mackova, Z., Koblovska, R., Lapcik, O., 2006. Distribution of isoflavonoids in non-
230
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Please cite this article in press as: Djouossi, M.G., et al., Chevalierinoside B and C: Two new isoflavonoid glycosides from the stem bark of
Antidesma laciniatum Muell. Arg (syn. Antidesma chevalieri Beille). Phytochem. Lett. (2014), http://dx.doi.org/10.1016/j.phy-
tol.2014.05.013