Five lignans (-)-(7R,8S)-dihydrodehydrodiconiferyl alcohol (1), (7S,8R)-3,3¢,5-trimethoxy-4¢,7-epoxy-8,5¢-neolignan-4,9,9¢-triol (2), (+)-isolariciresinol (3), polystachyol (4), (+)-pinoresinol (5) were isolated from the mangrove plant Rhizophora stylosa Griff.. The chemical structures of these compounds were elucidated by analysis of their NMR spectra and compared with those reported references. All these compounds were isolated from this plant for the first time

Cuong, Nguyen The

Cuong, Nguyen Xuan

Diep, Chau Ngoc

Kiem, Phan Van

Minh, Chau Van

Nam, Nguyen Hoai

Thai, Tran Huy

Thanh Huong, Phan Thi

Thanh, Nguyen Van

Vietnam Academy of Science and Technology: Journals Online

 42 
VIETNAM JOURNAL OF CHEMISTRY         VOL. 53(2e) 42-47                                               APRIL 2015 
DOI: 10.15625/0866-7144.2015-2e-010 
  
 
 
FIVE LIGNANS FROM THE MANGROVE RHIZOPHORA STYLOSA GRIFF. 
 
Phan Thi Thanh Huong
1
, Nguyen Van Thanh
1*
, Chau Ngoc Diep
1
, Nguyen The Cuong
2
,  
Nguyen Xuan Cuong
1
, Nguyen Hoai Nam
1
, Tran Huy Thai
2
, Phan Van Kiem
1
, Chau Van Minh
1 
 
1
Institute of Marine Biochemistry, Vietnam Academy of Science and Technology (VAST) 
2
Institute of Ecology and Biological Resources, VAST 
Received 23 January 2015; Accepted for Publication 18 March 2015 
 
 
Abstract 
Five lignans ()-(7R,8S)-dihydrodehydrodiconiferyl alcohol (1), (7S,8R)-3,3,5-trimethoxy-4,7-epoxy-8,5-
neolignan-4,9,9-triol (2), (+)-isolariciresinol (3), polystachyol (4), (+)-pinoresinol (5) were isolated from the mangrove 
plant Rhizophora stylosa Griff.. The chemical structures of these compounds were elucidated by analysis of their NMR 
spectra and compared with those reported references. All these compounds were isolated from this plant for the first 
time.    
Keywords. Rhizophora stylosa, mangrove, lignans. 
 
1. INTRODUCTION 
 
Rhizophora stylosa Griff. (Rhizophoraceae) is a 
common mangrove plant that grows in the coastal 
areas of Vietnam, from Quang Ninh to Ba Ria – 
Vung Tau province [1]. Some Rhizophora species 
are used by the local people as folk medicines for 
many diseases. For example, the bark of R. 
mucronata is used for the treatment of diabetes in 
India [2], and when boiled in water it is used as an 
astringent for diarrhea, nausea, and vomiting and as 
an antiseptic in Thailand [3]. Previous 
phytochemical studies revealed that flavanols, 
flavanol glycosides, and triterpenes have been 
isolated from R. stylosa. In addition, bioactivity 
investigation has shown that some of these 
compounds displayed antioxidant activity [4, 5, 6]. 
In this paper, we report the isolation and structural 
elucidation of five known lignan compounds 15 
from the leaves of this plant. 
 
2. EXPERIMENTAL 
 
2.1. General experimental procedures 
 
 NMR spectra were recorded on a Bruker 
AM500 FT-NMR spectrometer (Bruker, Billerica, 
MA, U.S.A.) using TMS as an internal standard. The 
ESI-MS was measured on Agilent 1260 series single 
quadrupole LC/MS systems. Column 
chromatography (CC) was performed using a silica 
gel (Kieselgel 60, 70230 mesh and 230400 mesh, 
Merck, Darmstadt, Germany) or YMC RP-18 resins 
(30 - 50 μm, Fuji Silysia Chemical Ltd, Aichi, 
Japan). Thin layer chromatography (TLC) used pre-
coated silica gel 60 F254 (1.05554.0001, Merck, 
Darmstadt, Germany) and RP-18 F254S plates 
(1.15685.0001, Merck, Darmstadt, Germany) and 
compounds were visualized by spraying with 
aqueous 10 % H2SO4, then heating for 35 minutes. 
 
2.2. Plant material 
 
The samples of the mangrove plant Rhizophora 
stylosa Griff. were collected in July 2013 at Xuan 
Thuy national park, Nam Dinh province, Vietnam 
and were identiﬁed by Dr. Nguyen The Cuong, 
Institute of Ecology and Biological Resources, 
VAST.  A voucher specimen (No. XT_CB05C) was 
maintained at the IMBC, VAST. 
 
2.3. Extraction and isolation 
 
Dried leaves of R. stylosa (1.8 kg) were 
powdered and extracted with hot MeOH (three times 
at 50
o
C for 6 h each) to give a MeOH residue (200 g, 
A) after removal of the solvent in vacuum. This 
extract was suspended in water and partitioned in 
turn with n-hexane and CH2Cl2 to provide the 
corresponding extracts: n-hexane (H, 80 g), CH2Cl2
 43 
VJC, Vol. 53(2e), 2015                                                                                                Nguyen Van Thanh, et al. 
(C, 20 g), and a water layer. 
Extracts H and C were combined and crudely 
separated by silica gel CC using a gradient 
concentration of MeOH in CH2Cl2 (0-100 %) to 
obtain seven fractions (H1H7). Fraction H4 (4.1 g) 
was further separated by YMC RP-18 CC and eluted 
with MeOHwater (2.5:1, v/v), followed by silica 
gel CC with n-hexaneEtOAc (1:1, v/v) to give 
compound 5 (7.0 mg). Fraction H5 (5.2 g) was 
subjected to column chromatography on a silica gel 
column and eluting with CH2Cl2/MeOH (15:1, v/v) 
to afford five subfractions H5A-H-5E. Subfraction 
H5B was separated by YMC using MeOH/H2O (1:2) 
as eluent to give four subfractions H5B1-H5B4. 
Subfraction H5B1 was purified further by silica gel 
CC and eluted with CH2Cl2/MeOH/H2O (20:1:0.1) 
to obtain compound 3 (5.0 mg) and compound 4 (5.5 
mg). Separation of subfractions H5B2 through 
Sephadex LH-20 CC eluted with MeOH/H2O (1:2) 
to give compound 1 (4.5 mg) and compound 2 (5.0 
mg). 
()-(7R,8S)-dihydrodehydrodiconiferyl alcohol 
(1): Yellowish oil; 
1
H-NMR (500 MHz, CD3OD) 
and 
13
C-NMR (125 MHz, CD3OD) see table 1; 
Positive ESI-MS: m/z 361 [M+H]
+
. 
(7S,8R)-3,3,5-trimethoxy-4,7-epoxy-8,5-
neolignan-4,9,9-triol (2): Colorless amorphous 
solid; 
1
H-NMR (500 MHz, CD3OD) and 
13
C-NMR 
(125 MHz, CD3OD) see table 1. Positive ESI-MS: 
m/z 391 [M+H]
+
. 
(+)-isolariciresinol (3): white amorphous 
powder; 
1
H-NMR (500 MHz, CD3OD) and 
13
C-
NMR (125 MHz, CD3OD) see table 2. Positive ESI-
MS: m/z 383 [M+Na]
+
. 
Polystachyol (4): white amorphous powder; 
1
H-
NMR (500 MHz, CD3OD) and 
13
C-NMR (125 MHz, 
CD3OD) see table 2. Positive ESI-MS: m/z 421 
[M+H]
+
. 
(+)-pinoresinol (5): Colorless oil; 
1
H-NMR 
(500 MHz, CD3OD) and 
13
C-NMR (125 MHz, 
CD3OD) see table 3. Positive ESI-MS: m/z 381 
[M+Na]
+
. 
 
Figure 1: Structures of compounds 15 
 
3. RESULTS AND DISCUSSION 
 
Compound 1 was obtained as yellowish oil. The 
mass spectrometry gave an [M + H]
+
 ion at m/z 361 
indicating a mass 360 compatible with the molecular 
formula of C20H24O6. The 1D and 2D-NMR spectra 
of 1 revealed that 1 was a derivative of a 
dihydrobenzofuran-type neolignan. The 
13
C-NMR 
and DEPT spectra showed signals for seven 
aromatic quaternary carbons, four of which are oxy-
quaternary; seven methines including five aromatic 
methines; two oxy-methylenes; two methylenes; and 
two methoxy carbons. The 
1
H-NMR spectrum 
displayed signals for an ABX coupling system at δ 
 44 
VJC, Vol. 53(2e), 2015                                                                                  Five lignans from the mangrove… 
6.97 (1H, d, 2.0, H-2), δ 6.78 (1H, d, 8.0, H-5), δ 
6.84 (1H, dd, 2.0, 8.0, H-6) of the 1,3,4-
trisubstituted benzene A ring which were connected 
to a C7 unit belonging to the signals at δ 5.51 (1H, d, 
7.0, H-7), 3.48 (1H, m, H-8), and 3.78 (1H, m, Ha-
9)/3.85 (1H, m, Hb-9). The 
1
H-NMR spectrum also 
supported the presence of a 1,3,4,5-tetrasubstituted 
benzen B ring with the signals of a pair of meta-
coupled at δ 6.75 (1H, br s, H-2) and 6.75 (1H, br s, 
H-6). In the aliphatic region, the signals of two 
benzylic proton at δ 2.65 (2H, t, 7.5, H-7), two 
aliphatic proton at δ 1.84 (2H, m, H-8’) and two 
oxygenated methylene protons at δ 3.60 (2H, t, 7.0, 
H-9) were assigned to a n-propanol moiety, that was 
a C3 unit of the B ring. Moreover, two singlet signals 
of two methoxy groups were also observed at δ 3.84 
(3H, s, 3-OMe) and 3.87 (3H, s, 3-OMe). In the 
HMBC spectrum, the correlations (Fig. 2) from H-7 
to C-1, C-2, C-6, C-8, C-9, C-4, C-5 and from H-8 
to C-9, C-7, C-1, C-4, C-5 indicated that 
dihydrobenzofuran moiety was attached to C-1 of 
the aromatic A ring. Similarly, the HMBC cross 
peaks between H-7 and C-1, C-2, C-6, C-8, C-9 
revealed the n-propanol moiety was linked to C-1 of 
the aromatic B ring. The coupling constant (J = 7.0 
Hz) between H-7 and H-8 indicated the relative 
trans-vicinal coupling of 7-aryl, 8-hydroxymethyl to 
the dihydrobenzofuran ring. On the basis of the 
above evidence, the structure of 1 was identified as 
()-(7R,8S)-dihydrodehydrodiconiferyl alcohol by 
comparison of spectral data with those reported in 
the literature [7]. 
Compound 2, a colorless amorphous solid, 
exhibited a molecular ion peak [M + H]
+
 at m/z 391 
in ESI-MS, suggesting a molecular formula of 
C21H26O7. The data of 
1
H- and 
13
C-NMR spectra of 2 
were very similar to those of compound 1 except for 
the appearance of a methoxy group at C-5 position. 
So, the 
1
H-NMR spectrum of 2 showed the presence 
of an AB coupling system in the aromatic A ring, 
represented by a pairs of broad singlet at δ 6.70 (2H, 
br s, H-2, 6). Moreover, the HMBC correlations 
were observed from proton of 5-OMe to C-5 
indicating that methoxy group attached at the C-5. 
Thus, 2 was identified to be (7S,8R)-3,3,5-
trimethoxy-4,7-epoxy-8,5-neolignan-4,9,9-triol by 
comparison with the reported chemical data [8].
Table 1: The NMR data of compounds 1 and 2 
C 
1 2 
#C C
a, b H
a, c
 (J = Hz) ##C C
a, b H
a, c
 (J = Hz) 
1 134.8 134.83 - 132.2 134.06 - 
2 110.5 110.57 6.97 (1H, d, 2.0) 103.1 104.17 6.70 (1H, br s) 
3 149.1 149.10 - 147.1 147.34 - 
4 147.5 147.50 - 134.6 136.36 - 
5 116.1 116.14 6.78 (1H, d, 8.0) 147.1 147.34 - 
6 119.7 119.71 6.84 (1H, dd, 2.0, 8.0) 103.1 104.17 6.70 (1H, br s) 
7 89.0 88.99 5.51 (1H, d, 7.0) 88.1 89.10 5.52 (1H, d, 6.5) 
8 55.4 55.45 3.48 (1H, m) 53.8 55.56 3.49 (1H, m) 
9 65.0 65.78 
3.78 (1H, m) 
3.85 (1H, m) 
63.7 65.00 
3.78 (1H, m) 
3.85 (1H, m) 
3-OMe 56.4 56.39 3.84 (3H, s) 56.3 56.78 3,83 (3H, s) 
5-OMe - - - 56.3 56.78 3,83 (3H, s) 
1 136.9 136.92 - 135.5 137.01 - 
2 115.8 114.15 6.75 (1H, br s) 112.4 114.16 6.75 (1H, br s) 
3 145.2 145.21 - 144.2 146.20 - 
4 147.5 147.55 - 146.5 147.50 - 
5 129.9 129.91 - 127.7 129.81 - 
6 117.9 117.94 6.75 (1H, br s) 115.9 117.94 6.75 (1H, br s) 
7 32.9 32.91 2.65 (2H, t, 7.5) 32.0 32.88 2.65 (2H, t, 7.5) 
8 35.8 35.81 1.84 (2H, m) 34.6 35.77 1.84 (2H, m) 
9 62.2 62.24 3.60 (2H, t, 7.0) 62.2 62.23 3.59 (2H, t, 7.0) 
3-OMe 56.7 56.78 3.87 (3H, s) 56.0 56.81 3.88 (3H, s) 
a
recored in CD3OD, 
b
125 MHz, 
c
500 MHz, 
#C of ()-(7R,8S)-dihydrodehydrodiconiferyl alcohol in CD3OD [7],  
##C of (7S,8R)-3,3,5-trimethoxy-4,7-epoxy-8,5-neolignan-4,9,9-triol in CDCl3 [8]. 
 45 
VJC, Vol. 53(2e), 2015                                                                                                Nguyen Van Thanh, et al. 
Compound 3 was isolated as a white amorphous 
powder. A molecular formula of C20H24O6 was 
determined for compound 3 on the basis of the 
observation of a molecular ion peak [M+Na]
+ 
at m/z 
383 in ESI-MS. The 
13
C-NMR and DEPT 
spectroscopic data showed signals for seven 
aromatic quaternary carbons, four of which are oxy-
quaternary; eight methines including ﬁve aromatic 
methines; one methylene; two oxy-methylenes and 
two methoxy carbons. The 
1
H-NMR spectrum 
displayed signals for a 1,3,4-trisubstituted aromatic 
ring at δ 6.70 (1H, d, 2.0, H-2), δ 6.76 (1H, d, 8.0, 
H-5), δ 6.63 (1H, dd, 2.0, 8.0, H-6), and signals for 
a 1,3,4,5-tetrasubstituted benzene ring at δ 6.68 (1H, 
s) and 6.21 (1H, s). It further showed two methoxy 
groups at δ 3.83 (3H, s, 3-OMe), δ 3.80 (3H, s,       
3-OMe), two oxygenated methylene group with
overlapped signals at δ 3.69 (1H, Ha-9)/3.72 (1H, 
Hb-9), δ 3.70 (1H, Ha-9)/3.42 (1H, dd, 4.0, 11.0, Hb-
9), a methylene group at δ 2.79 (2H, d, 7.5, H-7), 
three methine group at δ 3.82 (1H, H-7’), 2.02 (1H, 
m, H-8), 1.80 (1H, m, H-8). The 1H- and 13C-NMR 
spectra strongly implied that compound 3 could be a 
lignan. In the HMBC spectrum, the correlations 
between H-7 and C-1, C-2, C-6, C-8, C-9, C-8, and 
between H-7 and C-1, C-2, C-6, C-8, C-1, C-2, C-
6, C-8, C-9 revealed 3 to be an aryl-tetralin type 
lignan. The HMBC correlation (Fig. 2) from proton 
3-OMe to C-3 and from proton 3-OMe to C-3 
confirmed the positions of two methoxy group. The 
absolute configuration of 3 was determined on the 
basis of the good agreement of NMR spectral data 
with those of (+)-isolariciresinol [9]. Therefore, 
compound 3 was identified to be (+)-isolariciresinol.
Table 2: The NMR data of compounds 3 and 4 
C 
3 4 
#C C
a, b H
a, c
 (J = Hz) ##C C
a, b H
a, c
 (J = Hz) 
1 129.0 129.04 - 130.2 130.20 - 
2 112.4 112.41 6.68 (1H, s) 126.2 126.25 - 
3 147.2 147.22 - 147.7 147.70 - 
4 145.3 145.29 - 138.9 138.89 - 
5 117.3 117.36 6.21 (1H, s) 148.7 148.67 - 
6 134.2 134.18 - 107.8 107.81 6.61 (1H, s) 
7 33.6 33.57 2.79 (2H, d, 7.5) 33.6 33.55 
2.59 (1H, dd, 11.5, 15.0) 
2.72 (1H, dd, 5.0, 15.0) 
8 40.0 40.01 2.02 (1H, m) 40.9 40.89 1.65 (1H, m) 
9 65.9 65.97 
3.69
d
 (1H) 
3.72
d 
(1H) 
66.8 66.80 
3.51
d
 (1H) 
3.62 (1H, dd, 5.0, 12.0) 
1 138.6 138.63 - 139.3 139.31 - 
2 113.8 113.83 6.70 (1H, d, 2.0) 106.8 106.90 6.40 br (1H, s) 
3 149.0 149.03 - 149.0 148.99 - 
4 145.9 145.95 - 134.5 134.54 - 
5 115.9 115.99 6.76 (1H, d, 8.0) 149.0 148.99 - 
6 123.2 123.11 6.63 (1H, dd, 2.0, 8.0) 106.8 106.90 6.40 (1H, s) 
7 48.1 48.05 3.82
d
 (1H) 42.3 42.29 4.33 (1H, d, 5.5) 
8 48.0 48.02 1.80 (1H, m) 49.6 49.50 2.00 (1H, m) 
9 62.2 62.25 
3.70
d
 (1H) 
3.42 (1H, dd, 4.0, 11.0) 
64.1 64.20 3.51
d
 (2H) 
3-OMe 56.4 56.41 3.83 (3H, s) 60.1 60.17 3.40 (3H, s) 
5-OMe - - - 56.6 56.62 3.88 (3H, s) 
3-OMe 56.3 56.37 3.80 (3H, s) 56.7 56.78 3.76 (3H, s) 
5-OMe - - - 56.7 56.78 3.76 (3H, s) 
a
recored in CD3OD, 
b
125 MHz, 
c
500 MHz, 
d
overlapped signal, 
#C of (+)-isolariciresinol in CD3OD [9],  
##C of polystachyol in CD3OD [10]. 
 46 
VJC, Vol. 53(2e), 2015                                                                                  Five lignans from the mangrove… 
 
Figure 2: Key HMBC correlations of compounds 1 and 3 
 
Compound 4 was obtained as a white amorphous 
powder. The ESI-MS spectra of 4 exhibited an ion 
peak [M + H]
+
 at m/z 421, which is in agreement 
with the molecular formula C22H28O8. Its NMR data 
is very similar to those of 3, except for the 
appearance of two methoxy group at C-5 and C-5 
position. The 
1
H-NMR spectrum showed an 
aromatic proton signal at δ 6.61 (1H, s, H-6) 
attributed to benzene A ring, and a singlet signal of 
two other aromatic protons at δ 6.40 (2H, s, H-2, 6) 
were due to benzene B ring. The small coupling 
constant (J = 5.5 Hz) between H-7 and H-8 
observed in the 
1
H-NMR spectrum, established that 
the relative configuration of H-7 and H-8 was cis. 
Moreover, the absolute configuration of 4 was 
determined on the basis of the good agreement of 
NMR spectral data with those of polystachyol [10]. 
Thus, 4 was deduced as polystachyol. 
Compound 5 was isolated as colorless oil. Its 
molecular formula was established as C20H22O6 on the 
basis of an ion peak [M+Na]
+ 
at m/z 381 in ESI-MS. 
In the 
13
C-NMR there were signals for only ten 
carbons, suggested that 5 might be a symmetrical 
structure. The 
1
H-NMR spectrum showed signals for 
six aromatic protons of an ABX spin system at δ 6.97 
(2H, d, 2.0, H-2, 2), δ 6.79 (2H, d, 8.0, H-5, 5), δ 
6.83 (2H, dd, 8.0; 2.0, H-6, 6), six protons of two 
methoxy group at δ 3.88 (6H, s, 3, 3-OMe), two 
protons of two oximethine group at δ 4.73 (2H, d, 4.0, 
H-7, 7), two protons of two methine group at δ 3.17 
(2H, m, H-8, 8), and four protons of two 
oxymethylene groups at δ 3.86 (2H, dd, 9.0, 3.5, Ha-9, 
9) and 4.25 (2H, dd, 9.0, 7.0, Hb-9, 9). The above 
data indicated that compound 5 was assigned to be a 
lignan of the furofurane type. By comparing the NMR 
spectral data with those reported in literature, the 
structure of 5 was determined as (+)-pinoresinol [11].
Table 3: The NMR data of compound 5 
C
 #δC δC
a,b
 δH
a,c
 (J = Hz) C
 #δC δC
a,b
 δH
a,c
 (J = Hz) 
1, 1 134.62 133.82 - 6, 6 120.07 120.07 6.83 (2H, dd, 8.0; 2.0) 
2, 2 111.05 111.02 6.97 (2H, d, 2.0) 7, 7 87.08 87.55 4.73 (2H, d, 4.0) 
3, 3 148.78 149.14 - 8, 8 55.68 55.37 3.17 (2H, m) 
4, 4 147.31 147.33 - 9, 9 72.66 72.62 
3.86 (2H, dd, 9.0, 3.5) 
4.25 (2H, dd, 9.0, 7.0) 
5, 5 116.00 116.10 6.79 (2H, d, 8.0) 3, 3-OMe 56.70 56.44 3.88 (6H, s) 
a
recored in CD3OD, 
b
125 MHz, 
c
500 MHz, 
#C of (+)-pinoresinol in acetone-d6 [11]. 
 
4. CONCLUSION 
 
From the MeOH extract of the fruit of 
Rhizophora stylosa, using column chromatography, 
five lignan compounds ()-(7R,8S)-
dihydrodehydrodiconiferyl alcohol (1), (7S,8R)-
3,3,5-trimethoxy-4,7-epoxy-8,5-neolignan-4,9,9-
triol (2), (+)-isolariciresinol (3), polystachyol (4), 
(+)-pinoresinol (5) were isolated. Based on 1D-
NMR and 2D-NMR as well as comparison with 
published data, their chemical structures were 
elucidated. This is the first report of these 
compounds from this species.  
 
Acknowledgements. This work was financially 
supported by Vietnam Academy of Science and 
 47 
VJC, Vol. 53(2e), 2015                                                                                                Nguyen Van Thanh, et al. 
Technology, project code: VAST.ĐTCB 02/13-14. 
The authors are grateful to Institute of Chemistry, 
VAST for measuring NMR spectra. 
 
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Corresponding author:  Nguyen Van Thanh 
Institute of Marine Biochemistry, Vietnam Academy of Science and Technology 
18 Hoang Quoc Viet, Cau Giay, Hanoi, Vietnam 
E-mail: thanhcmgu@yahoo.com 
Tel. 0988091377. 
 


Five lignans from the mangrove Rhizophora stylosa Griff.

http://vjs.ac.vn/index.php/vjchem/article/download/0866-7144.2015-2e-010/5519

Five lignans from the mangrove Rhizophora stylosa Griff.

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