A new megastigmane diglycoside from litsea glutinosa (Lour.) C. B. Rob.

Article abstract of DOI:10.1590/S0103-50532011001100030

Phytochemical study on the leaves and twigs of afforded the new megastigmane diglycoside (6S, 7E, 9R)-6, 9-dihydroxy-4, 7-megastigmadien-3-one- 9-O-[α-L-arabinofuranosyl-(l→6)]-β-D-glucopyranoside (1), along with glycosides (6S, 7E, 9R)-roseoside (2), (7'R, 8'R)-3, 5'-dimethoxy-9, 9'-dihydroxy-4, 7'-epoxylignan 4'-β-D-glucopyranoside (3), (7'R, 8'S)-dihydrodehydrodiconifenyl alcohol 9'-O-β-D-xylopyranoside (4) and pinoresinol 3-O-β-D-glucopyranoside (5). Their structures were established on the basis of extensive spectroscopic and chemical methods. Compounds 2-5 were reported for the first time in this species. Compound 1 was evaluated for cytotoxic activities against human tumor cell lines (myeloid leukemia HL-60, hepatocellular carcinoma SMMC-7721, lung cancer A-549, breast cancer MCF-7 and colon cancer SW480 cells), for which it was proved to be inactive (IC ₅₀ > 40 μM).

Full text of DOI:10.1590/S0103-50532011001100030

J. Braz. Chem. Soc., Vol. 22, No. 11, 2234-2238, 2011.
Printed in Brazil - ©2011 Sociedade Brasileira de Química
0
103 - 5053 $6.00+0.00
Short Report
S
A New Megastigmane Diglycoside from Litsea glutinosa (Lour.) C. B. Rob.
a
b
c
a
a
Yun-Song Wang, Zhen Liao, Yan Li, Rong Huang, Hong-Bing Zhang and
,
a
Jing-Hua Yang*
a
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education,
School of Chemical Science and Technology, Yunnan University, Kunming 650091, P. R. China
b
Yunnan Academy of Tobacco Science, Kunming 650031, P. R. China
c
State Key Laboratory of Phytochemistry and Plant Resources in West China,
Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P. R. China
Estudo fotoquímico das folhas e galhos de Litsea glutinosa (Lour.) C. B. Rob. forneceu
um novo diglucosídeo megastimano (6S, 7E, 9R)-6, 9-dihidroxi-4, 7-megastigmadieno-3-ona-
9
(
4
-O-[a-L-arabinofuranosil-(l→6)]-b-d-glucopiranosídeo (1), juntamente com os glicosídeos
6S, 7E, 9R)-roseosido (2), (7’R, 8’R)-3, 5’-dimetoxi-9, 9’-dihidroxi-4, 7’-epóxi lignina
’-b-D-glucopiranosídeo (3), álcool (7’R, 8’S)-dihidrodehidrodiconifenil 9’-O-b-D-
xilopiranosídeo (4) e pinoresinol 3-O-b-D-glucopiranosídeo (5). Suas estruturas foram
estabelecidas com base em métodos espectroscópicos e químicos. Compostos 2-5 são reportados
pela primeira vez nestas espécies. Composto 1 foi avaliado para atividades citotóxicas de linhagens
de células tumorais humanas (células leucemia mielóide HL-60, carcinoma hepatocelular
SMMC-7721, câncer de pulmãoA-549, câncer da mama MCF-7 e câncer do colo SW480), para
as quais provou-se ser inativo (IC > 40 mM).
5
0
Phytochemical study on the leaves and twigs of afforded the new megastigmane diglycoside
(
6S, 7E, 9R)-6, 9-dihydroxy-4, 7-megastigmadien-3-one-9-O-[a-L-arabinofuranosyl-(l→6)]-
b-D-glucopyranoside (1), along with glycosides (6S, 7E, 9R)-roseoside (2), (7’R, 8’R)-
3
, 5’-dimethoxy-9, 9’-dihydroxy-4, 7’-epoxylignan 4’-b-D-glucopyranoside (3), (7’R, 8’S)-
dihydrodehydrodiconifenyl alcohol 9’-O-b-D-xylopyranoside (4) and pinoresinol 3-O-b-D-
glucopyranoside (5). Their structures were established on the basis of extensive spectroscopic and
chemical methods. Compounds 2-5 were reported for the first time in this species. Compound 1
was evaluated for cytotoxic activities against human tumor cell lines (myeloid leukemia HL-60,
hepatocellular carcinoma SMMC-7721, lung cancerA-549, breast cancer MCF-7 and colon cancer
SW480 cells), for which it was proved to be inactive (IC > 40 mM).
50
Keywords: Lauraceae, Litsea glutinosa (Lour.) C. B. Rob., megastigmane glycosides, lignan
glycosides
Introduction
that Litsea species contain structurally diverse and
2-4
5,6
biologically active aporphine alkaloids, butanolides and
7-10
Litsea (Lauraceae) is a genus of about 200 species
mainly growing in tropical and subtropical Asia, some
distributed in Australia and from North America to
subtropical South America. In China, this genus is
represented by 72 species and mostly distributed in the
south and southwestern parts of the country, where many
of them are known for their edible fruits and medicinal
sesquiterpenes.
Litsea glutinosa (Lour.) C. B. Rob. is an evergreen tree
known in China as “Chan Gao Shu”. The leaves and twigs
of L. glutinosa (Lour.) have been used as a demulcent and
mild astringent for diarrhea and dysentery, whereas the
roots are used in local folk medicine to poultice sprains and
1
bruises. Earlier phytochemical studies on this plant have
1
11-16
properties. Previous phytochemical studies have indicated
been reported,
and these include the isolation of an
1
2
13
arabinoxylan, an abscisic acid derivative and lignans,
14
15
*
e-mail: yangjh@ynu.edu.cn
aporphine alkaloids and a flavone glycoside.

Vol. 22, No. 11, 2011
Wang et al.
2235
The present study resulted in the characterization
of a new megastigmane diglycoside (1), along with
known compounds (6S, 7E, 9R)-roseoside (2), (7'R, 8'R)-
eluted with CHCl -MeOH (9:1-1:1) to afford eight fractions
(I-VIII). FractionV (15 g) was further separated by reversed-
phase silica-gel column chromatography and eluted with
3
3
4
, 5'-dimethoxy-9, 9'-dihydroxy-4, 7'-epoxylignan
'-b-D-glucopyranoside (3), (7'R, 8'S)-dihydro-
H O-MeOH (7:3, 6:4, 5:5), and then Sephadex LH-20
2
column chromatography (MeOH elution) to give 2 (3 mg),
3 (5 mg) and 5 (10 mg). Fraction VI (21 g) was subjected
to silica-gel column chromatography and eluted with
CHCl -MeOH (9:1-1:1), and then to RP C-18 (H O-MeOH
dehydrodiconifenyl alcohol 9'-O-b-D-xylopyranoside
4), and pinoresinol 3-O-b-D-glucopyranoside (5), from the
EtOH extract of L. glutinosa leaves and twigs. Compound
was evaluated for cytotoxic activities against five tumor
(
3
2
1
7:3, 6:4) to yield compound 4 (6 mg). Fraction VII (14 g)
cell lines, for which it was proved to be inactive.
was rechromatographed on a silica-gel column and eluted
with CHCl containing increasing amounts of MeOH, and
3
Experimental
then to Sephadex LH-20 column chromatography (MeOH
elution) to give compound 1 (4 mg).
General
(6S, 7E, 9R)-6, 9-dihydroxy-4, 7-megastigmadien-3-one-
Commercial silica-gel plates (Qing Dao Marine Chemical
Group Co.) were used for thin layer chromatography (TLC)
analyses. Normal silica was used for normal (Qing Dao
Marine Chemical Group Co.) and reversed-phase CC (Merk).
UV spectra were measured on a Shimadzu UV-2401PC
spectrophotometer (lmax in nm). Optical rotation was
obtained on a Horiba SEAP-300 spectropolarimeter. Infrared
9-O-[a-L-arabinopyranosyl -(1→6)]-b-d-glucopyranoside
(1)
21
D
White amorphous powder; [a] -16° (c 0.55, MeOH);
-
1
IR (KBr) ν /cm 3460, 1642, 1548, 1413; UV (MeOH)
max
1
13
lmax/nm 250; H and C NMR: see Table1; HRESIMS (m/z)
-
calcd for C H O : 517.5525, found: 517.5513 [M-H] .
24
38 12
(
IR) spectra were measured on a Bio-Rad FTS-135 infrared
-1
1
13
spectrophotometer (νmax in cm ). H (500 MHz) and C NMR
125 MHz) spectra, as well as 2D-NMR spectra, were
Acid hydrolysis of compound 1
(
-
1
recorded on a Brucker DRX-500 spectrometer, chemical
shifts d in ppm related to TMS (coupling constant J in Hz).
Electrospray ionization mass spectrometry (ESI-MS) spectra
were acquired on aVG-Autospec 3000 mass spectrometers.
A solution of 1 (1 mg) in 1 mol L HCl (2 mL) was
o
heated at 80 C for 2 h. The reaction mixture was diluted
with H O and then extracted with Et O. D-glucose and
2
2
L-arabinose were identified from the aqueous phase by
TLC comparison with authentic substances.
Plant material
Bioassays
Leaves and twigs of L. glutinosa (Lour.) C. B. Rob.
were collected in Xishuangbanna in Yunnan Province
Human cancer cell lines myeloid leukemia HL-60,
hepatocellular carcinoma SMMC-7721, lung cancer
A-549, breast cancer MCF-7 and colon cancer SW480 cells
were used in the cytotoxic assay, which was performed
according to the MTT (3-(4,5-dimethylthiazol-2-yl)-
3,5-di-phenytetrazoliumromide) method in 96-well
(People’s Republic of China) in May 2003, and identified
by Professor Yu Chen of Kunming Institute of Botany. A
voucher specimen is deposited in the Key Laboratory of
Medicinal Chemistry for Natural Resource (Ministry of
Education, School of Chemical Science and Technology,
Yunnan University).
16
microplates. Cells were cultured in RPMI-1640 or DMEM
medium (Hyclone, USA) and supplemented with 10% fetal
o
Extraction and isolation
bovine serum (Hyclone, USA) in 5% CO at 37 C.
2
Powdered leaves and twigs of L. glutinosa (Lour.)
12.0 kg) were repeatedly extracted with EtOH at room
temperature. Then, the extract was concentrated under
reducedpressuretogiveabrownsyrup,whichwaspartitioned
Results and Discussion
(
2
1
Compound 1, [a]D -16° (c 0.55, CH OH) was
3
isolated as an amorphous powder. The molecular formula
in H O with solvents of increasing polarity to yield a
C H O was deduced from the high resolution fast atom
2
24 38 12
petroleum ether-fraction (80 g), an EtOAc-fraction (54g)and
a n-BuOH-fraction (108 g). The n-BuOH-soluble fraction
was subjected to silica-gel column chromatography and
bombardment mass spectrometry (HR-FABMS) exhibiting
a quasi-molecular ion at m/z 517.5513 [M-H] (calcd.
for 517.5525). Compound 1 showed UV absorption at
-

2
236
A New Megastigmane Diglycoside from Litsea glutinosa (Lour.) C. B. Rob.
J. Braz. Chem. Soc.
1
13
Table 1. H and C NMR spectral data for compounds 1 and 2 (in MeOD)
1
2
dH / ppm (mult, integral, J / Hz)
–
Position
dH / ppm (mult, integral, J / Hz)
–
dC
dC
1
2
2
3
4
5
6
7
8
9
1
1
1
1
42.5 s
50.8 t
42.4 s
50.7 t
b
a
2.54 (d, 1H, 17.0)
2.17 (d, 1H, 17.0)
–
2.50 (d, 1H, 17.0)
2.16 (d, 1H, 17.0)
–
50.8 t
50.7 t
201.4 s
127.3 d
167.4 s
80.1 s
131.7 d
134.9 d
76.8 d
21.1 q
23.5 q
24.7 q
19.8 q
102.6 d
75.2 d
76.7 d
71.9 d
78.0 d
68.0 t
201.2 s
127.2 d
167.3 s
80.0 s
131.6 d
135.3 d
77.3 d
21.2 q
23.4 q
24.7 q
19.6 q
102.8 d
75.3 d
78.1 d
71.7 d
78.2 d
62.9 t
5.90 (s, 1H)
5.85 (s, 1H)
–
–
–
–
5.85 (d, 1H, 15.7)
5.84 (dd, 1H, 15.7, 6.4 )
4.42 (quint., 1H, 6.4)
1.29 (d, 3H, 6.4)
1.04 (s, 3H)
5.86 (1H, overlap)
5.85 (1H, overlap)
4.41 (1H, m)
1.29 (d, 3H, 6.6)
1.02 (3H, s)
0
1
2
3
1.03 (s, 3H)
1.01 (3H, s)
1.92 (d, 3H, 1.5)
4.35 (d, 1H, 7.8)
3.16 (dd, 1H, 7.9 and 9.5)
3.40 (m, 1H)
1.93 (3H, d, 1.5)
4.33 (1H, d, 7.8)
3.18 (m, 1H)
3.33 (m, 1H)
3.33 (m, 1H)
3.23 (m, 1H)
Glu-1'
Glu-2'
Glu-3'
Glu-4'
Glu-5'
Glu-6'
3.31 (m, 1H)
3.29 (m, 1H)
4.00 (m, 1H)
3.84(brd, 1H, 10.7)
3.63 (brd, 1H, 10.7)
3
.58 (dd, 1H, 5.7 and 11.2)
Ara-1"
Ara-2"
Ara-3"
Ara-4"
Ara-5"
4.94 (d, 1H, 1.7)
109.9 d
83.1 d
78.9 d
85.9 d
63.1 t
4.00 (m, 1H)
3.82 (dd, 1H, 3.3 and 6.0)
3.97 (m, 1H)
3.74 (dd, 1H, 3.2 and 11.8)
3
.64 (dd, 1H, 5.4 and 11.8)
-
1
2
50 nm and an IR band at 1642 cm , characteristic of an
The locations of the sugar residues in 1 were established
by the presence of the NOESY (nuclear Overhauser
enhancement spectroscopy) cross peak between H-1'
(d 4.35) and H-9 (d 4.42), and HMBC (heteronuclear
multiple bond correlation) correlation between H-1' and
C-9 (d 76.8). These results demonstrated the glucosyl
moiety are connected to the 9-OH group of the aglycone
a,b-unsaturated carbonyl.
1
The H NMR spectrum of 1 showed signals assignable
to a double bond proton at d 5.90 (s), two vinyl protons at
d 5.85 (d, J 15.7 Hz) and d 5.84 (dd, J 15.7 and 6.4 Hz), an
oxygenated methine at d 4.42, an isolated methylene (d 2.54
and 2.17, each d, J 17.0 Hz), a vinyl methyl (d 1.92, d,
J 1.5 Hz), a secondary methyl (d 1.29, d, J 6.4 Hz) and two
tertiary methyl singlets at d 1.04 and 1.03 (Table 1). The
C NMR spectrum of 1 showed 24 carbon signals, including
those characteristic of a disaccharide moiety. Analysis of
D and 2D NMR spectra indicated that the aglycone
portion of 1 was identical to that of the megastigmane
glycosides (6S, 7E, 9R)-roseoside (2). H and C NMR
data of the disaccharide moiety suggested the presence of
glucopyranosyl and arabinofuranosyl units.
confirmed by acid hydrolysis of 1 that afforded D-glucose
and L-arabinose, which were identified by direct comparison
with authentic samples. The J values of the anomeric
1
7
through a glycosidic linkage. Furthermore, the C-6'
signal of the inner b-D-glucopyranosyl unit was observed
13
at d 68.0, indicating the involvement of this carbon in a
C
19
glycosidic linkage. The other anomeric proton (arabinose)
at d 4.94 was also correlated with C-6' of glucose at d 68.0
(Figure 2). From the above data, compound 1 appears
to be the arabinofuranosyl-(l"→6')-glucopyranosyl
analogue of roseoside. Literature data report that most
megastigmane glycosides possesses the 1"→6' linkage in
1
17
1
13
17,18
This was
19,20
their disaccharide unit.
Stereochemical assignments of 1 could be deduced
from NOESY, COSY and CD (circular dichroism)
1
1
protons at 4.35 (d, H-1', J 7.8 Hz, d 102.6d) and d 4.94
experiments. The H- H COSY spectra showed long-
C
(
d, H-1", J 1.7 Hz, d 109.9d) established the sugar units as
range couplings between H-2b and H -11, H-2a and H-4,
C
3
b-D-glucopyranosyl and a-L-arabinofuranosyl in 1.
whereas NOE (nuclear Overhauser effect) cross-peaks

Vol. 22, No. 11, 2011
Wang et al.
2237
OR
9
HO
1
2
1
1
7
1
0
6
OH
2
1
8
OH
OH
3
O
5
O
13
O
4
HO
HO
O
OMe
OMe
OH
1
2
R= Glu(6 1 )Ara
R= Glu
3
HO
OXyl
O
O
O
OH
MeO
OMe
HO
OMe
HO
OH
OH
O
OMe
O
4
5
OH
Figure 1. Chemical structures of compounds 1-5.
HO
OH
OH
OH
O
OH
O
HO
OH
OH
HO
O
OH
9
10
O
O
O
O
8
H
HO
H
OH
O
H
OH
7
2
4
O
Me
H
6
3
5
OH
HMBC
H
NOESY
O
1
Me12
Me
11
Figure 2. Key HMBC and NOESY correlations of 1.
were observed between H-7 and H-2b, H-2b and H -12,
The structures of known compounds 2-5 were identified
3
17
H-2a and H -11, H-2a and H -12 (Figure 2). These results
as (6S, 7E, 9R)-roseoside (2), (7’R, 8’R)-3, 5’-dimethoxy-
9, 9’-dihydroxy-4, 7’-epoxylignan 4’-b-D-glucopyranoside
3
3
demonstrated that the side-chain (C-7-C-10) was in a
pseudo-axial orientation to the half-chair conformation of
the cyclohexenone ring. The CD spectrum of 1 showed a
positive Cotton effect at 240 nm, similar to that of 2, thus
indicating a 6S-configuration. The absolute configuration
at C-9 of the aglycon was assigned as R on the basis of
a diagnostic chemical shift of the C-9 signal (d 76.8) in
2
1
(3), (7’R, 8’S)–dihydrodehydrodiconifenyl alcohol
2
3
9’-O-b-D- xylopyranoside (4) and pinoresinol
24
3-O-b-D-glucopyranoside (5), by comparison of physical
data and spectroscopic literature data. These glycosides are
reported for the first time from the genus Litsea.
Naturally occurring megastigmane derivatives are an
expanding class of compounds. Several oxidation steps
and glycosylation at the megastigmane scaffold afforded
several derivatives with anti-proliferative, anticancer and
1
3
21
the C NMR spectrum. Consequently, the structure
of 1 was determined to be (6S, 7E, 9R)-6,9-dihydroxy-
4
(
,7-megastigmadien-3-one-9-O-[a-L-arabinofuranosyl-
l"→6')]-b-d-glucopyranoside (Figure 1). Earlier study
reported the isolation of (6S, 7E, 9R)-6, 9-dihydroxy-
, 7-megastigmadien-3-one-9-O-[a-L-arabinopyranosyl-
l→6)]-b-d-glucopyranoside from Lonicera gracilipes
18,19,25-28
cytotoxic effects.
Compound 1 was tested for its
cytoxicity effects in the human tumor cell lines myeloid
leukemia HL-60, hepatocellular carcinoma SMMC-7721,
lung cancerA-549, breast cancer MCF-7 and colon cancer
SW480 cells, but it proved to be inactive (IC > 40 mM).
4
(
2
2
Var. glandulosa.
50

2
238
A New Megastigmane Diglycoside from Litsea glutinosa (Lour.) C. B. Rob.
J. Braz. Chem. Soc.
Supplementary Information
11. Mandal, S. C.; Kumar, C. K. A.; Majumder, A.; Majumder, R.;
Maity, B. C.; Fitoterapia 2000, 71, 439.
1
13
1
1
H and C NMR, H- H COSY, HSQC, HMBC,
12. Herath, H. M. T. B.; Kumar, N. S.; Wimalasiri, K. M. S.;
Carbohydr. Res. 1990, 198, 343.
NOESY NMR spectra of compound 1 are available free
of charge at http://jbcs.sbq.org.br as PDF file.
13. Pan, J.Y.; Zhang, S.; Wu, J.; Li, Q. X.; Xiao, Z. H.; Helv. Chim.
Acta 2010, 93, 951.
Acknowledgements
14. Yang, J. H.; Li, L.; Wang, Y. S.; Huang, R.; Zhao, J. F.; Luo,
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This work was supported by the National Nature
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007B0006Z and 2007PY01-23).
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Submitted: July 21, 2011
Published online: September 29, 2011

J. Braz. Chem. Soc., Vol. 22, No. 11, S1-S3, 2011.
Printed in Brazil - ©2011 Sociedade Brasileira de Química
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Supplementary Information
SI
A New Megastigmane Diglycoside from Litsea glutinosa (Lour.) C. B. Rob.
a
b
c
a
a
Yun-Song Wang, Zhen Liao, Yan Li, Rong Huang, Hong-Bing Zhang and
,
a
Jing-Hua Yang*
a
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education,
School of Chemical Science and Technology, Yunnan University, Kunming 650091, P. R. China
b
Yunnan Academy of Tobacco Science, Kunming 650031, P. R. China
c
State Key Laboratory of Phytochemistry and Plant Resources in West China,
Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650204, P. R. China
1
Figure S1. H NMR spectrum (500 MHz, MeOD) of compound 1.
13
Figure S2. C NMR spectrum (125 MHz, MeOD) of compound 1.
*e-mail: yangjh@ynu.edu.cn

S2
A New Megastigmane Diglycoside from Litsea glutinosa (Lour.) C. B. Rob.
J. Braz. Chem. Soc.
1
1
Figure S3. H- H COSY NMR spectrum (500 MHz, MeOD) of compound 1.
Figure S4. HSQC spectrum (MeOD) of compound 1.

Vol. 22, No. 11, 2011
Wang et al.
S3
Figure S5. HMBC spectrum (MeOD) of compound 1.
Figure S6. NOESY spectrum (MeOD) of compound 1.