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广西莪术的化学成分研究(英文)



全 文 : 2011 年 9 月 第 9 卷 第 5 期 Chin J Nat Med Sep. 2011 Vol. 9 No. 5 329

Chinese Journal of Natural Medicines 2011, 9(5): 0329−0333
doi: 10.3724/SP.J.1009.2011.00329
Chinese
Journal of
Natural
Medicines







Chemical Constituents from the Rhizomes of
Curcuma kwangsiensis
LI Jun1, 2, LIU Yue1, 2, LI Jian-Qiang1, 2, CHEN Li-Xia1, 2, ZHAO Feng 3, QIU Feng1, 2*
1School of Traditional Chinese Materia Medica, Shenyang Pharmaceutical University, Shenyang 110016, China;
2Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang
110016, China;
3School of Pharmacy, Yantai University, Yantai 264005, China
Available online 20 Sep. 2011
[ABSTRACT] AIM: To study the bioactive constituents of Curcuma kwangsiensis. METHODS: The compounds were isolated by
silica gel, Sephadex LH-20, and Rp-18 gel column chromatography, and preparative HPLC. The structures were elucidated by exten-
sive spectroscopic methods including 2D-NMR and HRESI-MS. RESULTS: Four new compounds, methyl p-(1-β-D-glucopyranosy-
loxy-1-methylethyl) benzoate (1), p-(1-β-D-glucopyranosyloxy-1-methylethyl) benzoic acid (2), 2, 3, 5-trihydroxy-1-(3-methoxy-4-
hydroxyphenyl)-7-(3, 5-dimethoxy-4-hydroxyphenyl) heptane (3), and 2, 3, 5-trihydroxy-1-(4-hydroxyphenyl)-7-(3, 5-dimethoxy-4-hy-
droxyphenyl) heptane (4), and three known ones, 1, 5-epoxy-3α-hydroxy-1-(3, 4-dihydroxy-5-methoxy-phenyl)-7-(3, 4-dihydroxy)
heptane (5), (3R′, 5S′)-3, 5-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(3, 4-dihydroxyphenyl) heptane (6), and 2, 4, 6-trihy-
droxyacetophenone-2, 4-di-O-β-D-glucopyranoside (7), were isolated. CONCLUSION: Compounds 1-4 were new natural compounds,
and 3–7 showed strong inhibitory effects on NO production induced by LPS in macrophages.
[KEY WORDS] Curcuma kwangsiensis; Chemical constituents; Diarylheptanoid; NO; Macrophages
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2011)05-0329-05

1 Introduction
Curcuma kwangsiensis S. G. Lee et C. F. Ling (Zingib-
eraceae), a perennial herbaceous plant of Zingiberaceae,
widely distributes in southwest China including Guangxi,
Sichuan, Guangdong, and Yunnan Provinces. Its roots are
well-known for medicinal uses in treating stomach trouble
and “Oketsu” [1], and various syndromes caused by problems
in blood circulation, such as arthralgia, psychataxia, and dys-
menorhea. The genus Curcuma has been reported to be rich
in diarylheptanoids and sesquiterpenoids [2–5]. These sub-
stances showed various bioactivities, such as estrogenic [6],
vasorelaxant [7] , heptoprotective [8], anti-inflammatory [9–10]
and antifungal effects [11]. Our previous papers reported the

[Received on] 26-Jul.-2011
[Research Funding] This project was supported by National Key
Science and Technology Special Project (No. 2009ZX09301-012)
and Program for Liaoning Excellent Talents in University (No.
LR201037).
[*Corresponding author] QIU Feng: Tel: 86-24-23986463, E-mail:
fengqiu2000@tom.com
These authors have no any conflict of interest to declare.
isolation and characterization of 23 new diarylheptanoids
from the EtOH extracts of C. kwangsiensis as well as their
anti-inflammatory activity [12–13]. In a continuous search for
bioactive consti- tuents from this plant, four new compounds
(1–4), and three known ones, 1, 5-epoxy-3α-hydroxy-1-(3,
4-dihydroxy-5-methoxyphenyl)-7-(3, 4-dihydroxy)heptane (5)
[14], (3R′, 5S′)-3, 5-dihydroxy-1-(4-hydroxy-3-methoxy-
phenyl)-7-(3, 4-dihydroxyphenyl) heptane (6) [15], 2, 4,
6-trihydroxyacetophenone-2, 4-di-O-β-D-glucopyranoside (7) [16]
were obtained (Fig. 1). This paper describes the isolation and
structure elucidation of 1–4, along with the inhibitory effects
of the isolated compounds on NO production in LPS-acti-
vated macrophages.
2 Results and Discussion
Compound 1 was isolated as a yellow oil. Its HRESI-MS
spectrum showed a significant ion [M + Na]+ peak at m/z
379.136 6, corresponding to the molecular formula C17H24O8
(calcd. 379.1363). Its 1H NMR spectrum showed resonances
for two methyl groups at δ 1.73 (s) and 1.64 (s), a methoxy
group at δ 3.93 (s), an anomeric proton at δ 4.37 (d, J = 7.2
Hz), and four aromatic protons at δ 7.99 and 7.76 (each 2H,
LI Jun, et al. /Chinese Journal of Natural Medicines 2011, 9(5): 329−333
330 Chin J Nat Med Sep. 2011 Vol. 9 No. 5 2011 年 9 月 第 9 卷 第 5 期


Fig. 1 Structures of 1-7 isolated from C. kwangsiensis
d, J = 8.4 Hz) which revealed a p-substituted benzene ring.
Acid hydrolysis of 1 produced D-glucose [17], and
β-configuration of the glucose moiety in 1 was characterized
from the coupling constant of the characteristic anomeric
proton. The 13C NMR spectrum displayed 17 signals con-
sisted of one carbonyl (δ 168.7), one methoxy (δ 52.7), one
quaternary carbon (δ 80.2), two methyls (δ 28.4 and 30.9), six
aromatic carbons (δ 153.7, 130.3, 130.0 × 2, 127.7 × 2), and
six β-D-Glc carbons (δ 99.8, 78.3, 77.8, 75.5, 71.9, 63.6 ).
The two methyls were assigned by the HMBC correlations
from H-2′ (δ 1.73) to C-3′ (δ 30.9) and C-1′ (δ 80.2), and H-3′
(δ 1.64) to C-2′ (δ 28.4) and C-1′ (δ 80.2), respectively. The
β-D-Glc moiety was located at C-1′ (δ 80.2) by the HMBC
correlations from H-1′′ (δ 4.37) to C-1′ (δ 80.2). Therefore,
the structure of 1 was determined as methyl p-(1-β-D-gluco-
pyranosyloxy-1-methylethyl) benzoate.
Compound 2, obtained as a yellow oil, was assigned the
molecular formula C16H22O8 by HRESI-MS ion m/z 365.120
5 [M + Na]+ (calcd. 365.1207). The 1H NMR spectrum of 2
indicated the presence of two methyl groups at δ 1.74 (s) and
1.89 (s), a characteristic anomeric proton at δ 5.04 (d, J = 7.2
Hz), and four aromatic protons at δ 8.47 and 8.01 (each 2H, d,
J = 8.1 Hz) which revealed a p-substituted benzene ring. Acid
hydrolysis of 2 produced D-glucose[17], and β-configuration of
the Glc moiety in 2 was characterized from the coupling con-
stant of the characteristic anomeric proton. The 13C NMR
spectrum displayed 17 signals consistent with one carbonyl
(δ 170.0), one quaternary carbon (δ 79.4), two methyls (δ
28.5 and 31.6), six aromatic carbons (δ 152.5, 130 × 2, 129.8,
127.0 × 2 ) and six β-D-Glc carbons (δ 100.2, 79.2, 78.6, 76.0,
72.2, 63.6). The two methyls were assigned by the HMBC
correlations from H-3′ (δ 1.74) to C-2′ (δ 28.5) and C-1′
(79.4), and from H-2′ (δ 1.89) to C-3′ (δ 31.6) and C-1′ (δ
79.4), respectively. The β-D-Glc moiety was attached to C-1′
(δ 79.4) by the HMBC correlations from H-1′′ (δ 5.04) to
C-1′ (δ 79.4). Thus, the structure of 2 was determined as
p-(1-β-D-glucopyranosyloxy-1-methylethyl) benzoic acid.
Compound 3, obtained as a yellow oil, showed the mo-
lecular formula C22H30O8, as determined by HRESI-MS m/z
445.183 7 [M + Na]+ (calcd. 445.183 3) and NMR data. The
1H NMR spectrum of 3 revealed a 1, 3, 4-trisubstituted [δ
6.78 (1H, d, J = 2.0 Hz), δ 6.64 (1H, d, J = 8.0 Hz), δ 6.62
(1H, dd, J = 8.0, 2.0 Hz)] and a 1, 3, 4, 5-tetrasubstituted [δH
6.41 (2H, br. s) H-2′′ and H-6′′] benzene rings. The 13C NMR
spectrum displayed 22 signals consistent of four methylenes
[δ 33.0, 40.2, 40.9, 41.1], three oxygenated methines [δ 70.7,
73.0, 76.5], three methoxys [δ 56.5, 56.8 (×2)], and 12 aro-
matic carbons [δ 132.2, 114.2, 148.9, 145.9, 116.1, 123.0,
134.6, 106.7 (× 2), 149.3 (× 2) and 135.6] attributed to two
oxygenated aromatic rings. The three hydroxyl groups were
assigned to C-2, C-3 and C-5 by HMBC correlations from
H-2 (δ 3.57) to C-1′ (δ 132.2), C-4 (δ 40.9), and H-3 (δ 3.63 )
to C-1 (δ 40.2), C-5 (δ 70.7), and H-5 (δ 3.73 ) to C-3 (δ
73.0), C-7(δ 33.0), respectively. Furthermore, the methoxy
group was attached to C-3′ by the NOESY correlations be-
tween δ 3.77(3H, s)and H-2′ (δ 6.78, d, J = 2.0 Hz). On the
other aromatic ring, the two methoxys should be located at
C-3′′ and C-5′′, which was supported by the HMBC correla-
tions from δ 3.75 (6H, s) to C-3′′ (δ 149.3) and C-5′′ (δ 149.3),
and also by the NOESY correlations between δ 3.75 (6H, s)
and H-2′′ (6′′). Compound 3 was therefore assigned as 2, 3,
5-trihydroxy-1-(3-methoxy-4-hydroxyphenyl)-7-(3, 5-dime-
thoxy-4- hydroxy phenyl) heptane.
Compound 4, obtained as a yellow oil. Its molecular
formula of 4 was determined to be C21H28O7 on the basis of
HRESI-MS (m/z 415.1727 [M + Na]+) and NMR data. The
1H NMR spectrum revealed a 1, 4-disubstituted [δ 6.65, 2H,
d, J = 8.5 Hz ; 7.01, 2H, d, J = 8.5 Hz], and 1, 3, 4,
5-tetrasubstituted [δ 6.41, 2H, br s, H-2′′ and H-6′′] benzene
rings. The 13C NMR spectrum displayed 21 signals consistent
of four methylenes [δ 33.0, 40.0, 40.9, 41.1], three oxyme-
thines [δ 70.8, 73.8, 77.0], two methoxys [δ 56.8 (×2)], and
12 aromatic ring carbons [δ 131.5, 116.2 (× 2), 131.5 (× 2),
156.9, 134.5, 106.7 (× 2), 149.3 (× 2), 145.6] attributed to
two oxygenated aromatic rings, suggesting a diarylheptanoid
structure. The three hydroxyl groups were assigned to C-2,
LI Jun, et al. /Chinese Journal of Natural Medicines 2011, 9(5): 329−333
2011 年 9 月 第 9 卷 第 5 期 Chin J Nat Med Sep. 2011 Vol. 9 No. 5 331

C-3 and C-5 by HMBC correlations from H-2 (δ 3.55) to C-1′
(δ 131.5), C-4 (δ 40.9), and H-3 (δ 3.61) to C-1 (δ 40.0), C-5
(δ 70.8) , and H-5 (δ 3.73 ) to C-3 (δ 73.0), C-7(δ 33.0), re-
spectively. The two methoxy groups should be located at
C-3′′ and C-5′′, which was supported by the HMBC correla-
tions from δ 3.75 (6H, s) to C-3′′ (149.3) and C-5′′ (149.3),
and also by the NOESY correlations between δ 3.75 (6H, s)
and H-2′′ (6′′). Compound 4 was therefore formulated as 2, 3,
5-trihydroxy-1-(4-hydroxyphenyl)-7-(3, 5-dimethoxy-4-hy-
droxyphenyl) heptane.
Compounds 3-7 were evaluated for their inhibitory ef-
fects on NO production induced by LPS in macrophages
(Table 3). Cell viability was determined by the MTT method
to find whether inhibition of NO production was due to the
cytotoxicity of the test compounds. As shown in Table 3,
indomethacin (IC50 12.96 ± 1.16 μmol·L-1) and hydrocorti-
sone (IC50 40.64 ± 3.22 μmol·L-1) were used as the positive
controls. Compounds 3, 4, 5, and 7 showed strong inhibitory
activity on NO production with IC50 values of 8.99, 8.14,
11.81 and 12.28 μmol·L-1, respectively.
3 Experimental
3.1 Apparatus and reagents
NMR experiments were performed on a BrukerAV-600
(600 MHz for 1H, 150 MHz for 13C) spectrometer, using
TMS as an internal standard. HRESI-MS were recorded on a
Table 1 1H NMR (600 MHz) and 13CNMR (150 MHz) Data
for Compounds 1 and 2
1 2 Posi-
tion δH (J in Hz) δC δH (J in Hz) δC
1 130.0 129.8
2,6 7.99 (2H, d, 8.4 ) 130.3 8.47 (2H, d, 8.1) 130.0
3,5 7.76 (2H, d, 8.4 ) 127.7 8.01 (2H, d, 8.1) 127.0
4 153.7 152.5
7 168.7 170.0
8 3.93 (3H, s) 52.7
1′ 80.2 79.4
2′ 1.73 (3H, s) 28.4 1.89 (3H, s) 28.5
3′ 1.64 (3H, s) 30.9 1.74 (3H, s) 31.6
1′′ 4.37 (1H, d, 7.2 ) 99.8 5.04 (1H, d, 7.2) 100.2
2′′ 3.41 (1H, o) 75.5 4.10 (1H, o) 76.0
3′′ 3.43 (1H, o) 78.3 4.18 (1H, o) 79.2
4′′ 3.45 (1H, o) 71.9 4.24 (1H, o) 72.2
5′′ 3.20 (1H, m) 77.8 3.80 (1H, m) 78.6
6′′ 3.79 (1H, dd, 11.4, 2.4) 3.65 (1H, dd, 11.4, 5.8 ) 63.6
4.49 (1H, br d,11.0)
4.34 (1H, dd,11.0, 5.6) 63.6
Measured in CD3OD for compoud 1 and in C5D5N for compoud 2;
“o” means overlapped
Table 2 1H NMR (600 MHz) and 13C NMR (150 MHz) Data
for Compounds 3 and 4
3 4
Position
δH (J in Hz) δC δH (J in Hz) δC
1a
1b
2.60 (1H, m)
2.75(dd,5.2,13.8) 40.2
2.59 (1H, m)
2.74(dd,5.3,13.8) 39.8
2 3.57 (1H, m) 76.5 3.55 (1H, m) 77.0
3 3.63 (1H, m) 73.0 3.61 (1H, m) 73.0
4 1.66 (2H, m) 40.9 1.67 (2H, m) 40.9
5 3.73 (1H, m) 70.7 3.73 (1H, m) 70.8
6 1.66 (2H, m) 41.1 1.67 (2H, m) 41.1
7a
7b
2.52 (1H, m)
2.61(1H, m) 33.0
2.52(1H, m)
2.61(1H, m) 33.0
1′ 132.2 131.5
2′ 6.78 (1H, d, 2.0) 114.2 7.01 (1H, d, 8.5) 131.5
3′ 148.9 6.65 (1H, d, 8.5) 116.2
4′ 145.9 156.9
5′ 6.64 (1H, d, 8.4) 116.1 6.65 (1H, d, 8.5) 116.2
6′ 6.62 (1H, dd, 8.4, 2.0) 123.0 7.01 (1H, d, 8.5) 131.5
1″ 134.6 134.5
2″ 6.41 (1H, s) 106.7 6.41 (1H, s) 106.7
3″ 149.3 149.3
4″ 134.6 134.6
5″ 149.3 149.3
6″ 6.41 (1H, s) 106.7 6.41 (1H, s) 106.7
3′-OCH3 3.77 (3H, s) 56.5
3″,5″-OCH3 3.75 (3H, s) 56.8 3.75 (3H, s) 56.8
1H NMR and 13C NMR signals were assigned unambiguously by
analyses of 1H NMR, 13C NMR, HSQC, NOESY and HMBC spectra
(in CD3OD).
Table 3 Inhibitory effect of compounds isolated from Cur-
cuma kwangsiensis on NO production induced by LPS in
macrophages a
Compound IC50 (μmol·L-1) Compound IC50 (μmol·L-1)
3 8.99 ± 0.73 indomethacinb 12.96 ± 1.16
4c 8.14 ± 0.80 hydrocortisoneb 40.64 ± 3.22
5 11.81 ± 1.08
6 25.79 ± 2.15
7 12.28 ± 1.12
a NO concentration of control group: 3.24 ± 0.21 μmol·L-1;
NO concentration of LPS-treated group: 33.46 ± 2.13 μmol·L-1;
b Positive control;
cCytotoxicity (100 μmol·L-1);
Other compounds show no cytotoxicity

Micro TOF-Q Bruker mass spectrometer. Silica gel GF254
prepared for TLC and silica gel (200-300 mesh) for column
chromatography (CC) were obtained from Qingdao Marine
Chemical Factory (Qingdao, China). Sephadex LH-20 was a
product of Pharmacia. Octadecyl silica gel was purchased
from Merck Chemical Company Ltd. RP-HPLC separations
were conducted using a PU-986 intelligent prep. pump
(JASCO, Japan), equipped with a UV-975 intelligent UV/VIS
LI Jun, et al. /Chinese Journal of Natural Medicines 2011, 9(5): 329−333
332 Chin J Nat Med Sep. 2011 Vol. 9 No. 5 2011 年 9 月 第 9 卷 第 5 期

detector (JASCO, Japan), and performed with a Inertsil
Prep-ODS C18 column (20 × 250 mm, 10 μm) (GL. Sciences
Inc. USA). All reagents were of HPLC or analytical grade
and were purchased from Tianjin Damao Chemical Company.
Spots were detected on TLC plates under UV lighter by
heating after spraying with anisaldehyde-H2SO4 reagent.
3.2 Plant material
The rhizomes of C. kwangsiensis were collected in Oc-
tober, 2006 in Guangxi, China, and identified by Professor
SUN Qi-Shi, of the School of Traditional Chinese Materia
Medica, Shenyang Pharmaceutical University. A voucher
specimen (AG-20061015) has been deposited in the
Herbarium of the Department of Natural Product Chemistry,
Shenyang Pharmaceutical University.
3.3 Extraction and isolation
The rhizomes of C. kwangsiensis (10 kg) were cut into
approximately 2 cm pieces and extracted with 70% EtOH
(100 L) for 2 h. The resulting EtOH extract was concentrated
in vacuo, suspended in H2O, and then partitioned succes-
sively with cyclohexane, EtOAc, and n-BuOH. The aqueous
extract (100 g) was subjected to macroporous resin D101
with EtOH-H2O (0 : 100 to 100 : 1) to obtain five fractions
CW1-CW5. Fraction CW2 was purified by ODS column
chromatography [MeOH-H2O (1 : 9 to 8 : 2)], followed by
RP-HPLC with MeOH-H2O ( 5 : 95) to afford compounds 2
(8 mg), 1 (10 mg) and 7 (10 mg). Fraction CW3 was sub-
jected to ODS column chromatography [MeOH-H2O (1 : 1)]
to afford three fractions CW31, CW32 and CW33. Fraction
CW31 was purified by prep. HPLC [MeOH–H2O, (55:45)] to
yield compounds 3 (6 mg) and 4 (4 mg). Fraction CW32 was
purified by prep. HPLC [MeOH–H2O, (45 : 55)] to yield
compounds 5 (8 mg) and 6 (11 mg).
Compound 1, pale yellow oil. ESI-MS: m/z 379 [M +
Na]+. HRESI-MS m/z 379.136 6 ([M + Na]+, C17H24O8Na;
calcd. 379.136 3); 1H and 13CNMR data see Table 1.
Compound 2, pale yellow oil. ESI-MS m/z 365 [M +
Na]+. HRESI-MS m/z 365.120 5 ([M + Na]+, C16H22O8Na;
calcd. 365.120 7); 1H and 13C NMR data see Table 1.
Compound 3, pale yellow oil. [α]25D +10.5 (c 0.1,
MeOH); ESI-MS m/z 445 [M + Na]+. HRESI-MS m/z
445.183 7 ([M + Na]+, C22H30O8Na; calcd. 445.183 3); 1H
and 13C NMR data see Table 2.
Compound 4, pale yellow oil. [α]25D +9.6 (c 0.1, MeOH);
ESI-MS m/z 415 [M + Na]+. HRESI-MS m/z 415.172 3 ([M +
Na]+, C21H28O7Na; calcd. 415.172 7); 1H and 13C NMR data
see Table 2.
Acid Hydrolysis of Compounds 1 and 2. A solution of
each compound (2.0 mg) in 1 mol·L-1 HCl (1 mL) was stirred
at 90 °C in a stoppered vial for 2 h. The solution after cooling
was evaporated under a stream of N2. Anhydrous pyridine
solutions (0.1 mL) of each residue and L-cysteine methyl
ester hydrochloride (0.06 mol·L-1) were mixed, and warmed
at 60 °C for 1 h. The trimethylsilylation reagent trimethylsilyl
imidazole (0.15 mL) was added, and warming at 60 °C for
another 30 min. After drying, the residue was partitioned
between H2O and cyclohexane. The cyclohexane layer was
concentrated, dissolved in 200 μL acetone, and analyzed by
GC using a DB-1701 column. Temperatures of the injector
and detector were 270 °C and 280 °C respectively. A tem-
perature gradient system was used for the oven, starting at
160 °C for 1 min and increasing up to 230 °C at a rate of 5 °C
/ min. The peak of the hydrolysate was detected at 23.92 min.
The peaks of authentic samples of D- and L-Glc after treat-
ment in the same manner were detected at 23.88 and 25.10
min, respectively.
NO Production Bioassay. Mouse monocyte-macro-
phage RAW 264.7 cells (ATCC TIB-71) were purchased
from the Chinese Academy of Sciences. RPMI 1640 medium,
penicillin, streptomycin, and fetal bovine serum were pur-
chased from Invitrogen (New York). Lipopolysaccharide
(LPS), dimethylsufoxide (DMSO), 3-(4, 5-dimethyl-2-thia-
zolyl)-2, 5-diphenyltetrazolium bromide (MTT), indo-
methacin, and hydrocortisone were obtained from Sigma Co.
(St. Louis, MO). RAW 264.7 cells were suspended in RPMI
1640 medium supplemented with penicillin (100 U·mL-1),
streptomycin (100 μg·mL-1), and 10% heat-inactivated fetal
bovine serum. The cells were harvested with trypsin and
diluted to a suspension in fresh medium. The cells were
seeded in 96-well plates with 1 × 105 cells / well and allowed
to adhere for 2 h at 37 °C in 5% CO2 in air. Then, the cells
were treated with 1 μg·mL-1 of LPS for 24 h with or without
various concentrations of test compounds. DMSO was used
as a solvent for the test compounds, which were applied at a
final concentration of 0.2% (V/V) in cell culture supernatants.
NO production was determined by measuring the accumu-
lation of nitrite in the culture supernatant using Griess re-
agent [18]. Briefly, 100 μL of the supernatant from incubates
was mixed with an equal volume of Griess reagent (0.1%
N-[1-naphthyl]ethylenediamine and 1% sulfanilamide in 5%
H3PO4). Cytotoxicity was determined by the MTT colorimet-
ric assay, after 24 h incubation with the test compounds. The
concentration of NO2– was calculated by a working line from
0, 1, 2, 5, 10, 20, 50, and 100 μmol·L-1 sodium nitrite solu-
tions, and the inhibitory rate on NO production induced by
LPS was calculated by the NO2– levels as follows:
[NO2–] LPS − [NO2–]LPS+sampleInhibitory rate (%)=100×
[NO2–] LPS − [NO2–]untreated
Experiments were performed in triplicate, and the data
are expressed as the x ± s of three independent experiments.
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广西莪术的化学成分研究
李 军 1, 2, 刘 越 1, 2, 李建强 1, 2, 陈丽霞 1, 2, 赵 锋 3, 邱 峰 1, 2*
1沈阳药科大学中药学院, 沈阳 110016
2沈阳药科大学基于靶点的药物设计与研究教育部重点实验室, 沈阳 110016
3烟台大学药学院, 烟台 264005
【摘 要】 目的:对广西莪术(Curcuma kwangsiensis)的根茎进行化学成分研究。方法:运用硅胶、Sephadex LH-20 柱色谱、
ODS 柱色谱和制备 HPLC 等分离手段进行化学成分的分离纯化, 根据其波谱数据鉴定其结构。结果:从广西莪术中分离得到 7
个化合物, 分别鉴定为:[4-(1′-hydroxy-1′-methylethyl) benzoate-1′-O-β-D-glucopyranoside] (1), [4-(1′-hydroxy-1′-methylethyl) ben-
zoic acid-1′-O-β-D-glucopyranoside] (2), 2, 3, 5-trihydroxy-1-(3-methoxy-4-hydroxyphenyl)-7-(3, 5-dimethoxy-4-hydroxyphenyl) hep-
tane (3) and 2, 3, 5-trihydroxy-1-(4-hydroxyphenyl)-7-(3, 5-dimethoxy-4-hydroxyphenyl)heptane (4), 以及 1, 5-epoxy-3α-hydroxy- 1-(3,
4-dihydroxy-5-methoxyphenyl)-7-(3, 4-dihydroxy)heptane (5), (3R′, 5S′)-3, 5-dihydroxy-1-(4-hydroxy-3-methoxyphenyl)-7-(3,
4-dihydroxyphenyl) heptane (6), 2, 4, 6-trihydroxyacetophenone-2, 4-di-O-β-D-glucopyranoside (7)。结论:化合物 1-4 为新化合物,化
合物 3-7 对脂多糖所致巨噬细胞产生一氧化氮表现出强的抑制活性。
【关键词】 广西莪术; 化学成分; 二苯庚烷类; 一氧化氮; 巨噬细胞

【基金项目】 国家重大科技攻关项目(No. 2009ZX09301-012), 辽宁省高校杰出人才项目(No. LR201037)