全 文 ： 药学学报 Acta Pharmaceutica Sinica 2010, 45 (9): 1139−1143 · 1139 ·




A new chromone derivative from Berchemia lineata
SHEN Yu-xia1, TENG Hong-li2, YANG Guang-zhong1, MEI Zhi-nan1*, CHEN Xiao-long1
(1. College of Pharmacy, South-Central University for Nationalities, Wuhan 430074, China;
2. Institute of National Medicine of Guangxi, Nanning 530001, China)
Abstract: To study the chemical constituents from the root of Berchemia lineata (L.) DC., nine compounds
were isolated from the EtOAc extract by using silica gel, RP-C18 silica gel column chromatography and preparative
HPLC. Based on the spectroscopic analysis, their structures were identified as 5-hydroxy-7-(2-hydroxypropyl)-
2-methyl-chromone (1), (−)-(1R, 2S)-erythro-5-hydroxy-7-(1, 2-dihydroxypropyl)-2-methyl-chromone (2),
naringenin (3), eriodictyol (4), (+)-aromadendrin (5), (+)-taxifolin (6), (+)-catechin (7), (+)-epigallocatechin
(8) and quercetin (9). Among them, compound 2 is a new chromone derivative. Compound 1 is a known
chromone derivative and isolated from this genus for the first time. Compounds 3−9 are known flavonoids and
isolated from this plant for the first time.
Key words: Berchemia lineata; chromone derivative; flavonoid
CLC number: R284.1 Document code: A Article ID: 0513-4870 (2010) 09-1139-05
铁包金中一个新的色原酮衍生物
沈玉霞 1, 滕红丽 2, 杨光忠 1, 梅之南 1*, 陈小龙 1
(1. 中南民族大学药学院, 湖北 武汉 430074; 2. 广西民族医药研究院, 广西 南宁 530001)

摘要: 利用正相硅胶、反相硅胶和 HPLC 等色谱手段进行化学成分的分离, 从铁包金乙酸乙酯提取物中分离
得到 9 个化合物。化合物经波谱分析鉴定为 5-hydroxy-7-(2-hydroxypropyl)-2-methyl-chromone (1)、(−)-(1R, 2S)-
erythro-5-hydroxy-7-(1, 2-dihydroxypropyl)-2-methyl-chromone (2)、柚皮素 (3)、圣草酚 (4)、(+)-香橙素 (5)、(+)-
花旗松素 (6)、(+)-儿茶素 (7)、(+)-表没食子儿茶素 (8) 和槲皮素 (9)。其中化合物 2 为新的色原酮衍生物, 化
合物 1 为首次从该属植物中分离得到。化合物 3～9 为黄酮类化合物, 为首次从该种植物中分离得到。
关键词: 铁包金; 色原酮衍生物; 黄酮类

The genus Berchemia (Rhamnaceae) with more
than 31 species, occurs mainly in Asia. Eighteen of
them have a wide distribution in the south of China.
The root of Berchemia lineata (L.) DC. has been used
as a remedy for the treatment of gall stones, stomach-
ache, rheumatic arthritis and lumbago in Chinese folk
medicine[1]. A literature survey revealed that few
phytochemical work has been carried out on the genus

Received 2010-04-29.
Project supported by the National Science Foundation of Guangxi (0991006).
*Corresponding author Tel / Fax: 86-27-67843220,
E-mail: meizhinan@163.com
Berchemia, and only some ligans, flavones, aromatic
glycosides and quinines have so far been reported[2].
In the continuing research, the bioactive components
of the EtOAc extract of B. lineata were systematically
studied. Nine compounds were isolated from the
EtOAc extract by using silica gel, RP-C18 silica gel
column chromatography and preparative HPLC.
They were identified as 5-hydroxy-7-(2-hydroxy-
propyl)-2-methyl-chromone (1), (−)-(1R, 2S)-erythro-
5-hydroxy-7-(1, 2-dihydroxypropyl)-2-methyl-chromone
(2), naringenin (3), eriodictyol (4), (+)-aromadendrin
(5), (+)-taxifolin (6), (+)-catechin (7), (+)-epigallocate-
DOI:10.16438/j.0513-4870.2010.09.004
· 1140 · 药学学报 Acta Pharmaceutica Sinica 2010, 45 (9): 1139−1143

chin (8) and quercetin (9) by spectral analysis (Figure 1).
Among them, compound 2 is a new chromone derivative.
Compound 1 is a known chromone derivative and
isolated from this genus for the first time. Compounds
3−9 are known flavonoids and isolated from this plant
for the first time. In this paper, the isolation and
structural elucidation of the new compound and one
known chromone derivative and seven known flavonoids
are presented.

Results and discussion
Compound 1 was structurally elucidated as the
known compound, 5-hydroxy-7-(2-hydroxypropyl)-2-
methyl-chromone[3].
Compound 2 was obtained as colorless needle
crystals, [α] 22D = −50.2 (c 0.22, MeOH); The HR-ESI-
MS of 2 showed a molecular ion peak at m/z: 273.073 7
indicating a molecular formula C13H14O5Na. The
1H NMR spectra showed two meta coupled aromatic
protons (δ 6.68 (1H, s), 6.73 (1H, s)), one olefinic
proton (δ 6.65 (1H, s)), two oxygenated methines
(δ 4.62 (1H, d, J = 5.4 Hz), 4.37 (1H, m)), one singlet
signal for methyl group (δ 2.72 (3H, s)) and one methyl
group attached to a oxygenated methine (δ 1.35 (3H,
d, J = 6.3 Hz)). The 13C NMR and DEPT spectra
displayed the presence of two methyl groups (δ 19.5,
23.4), five CH groups including two oxygenated
methines (δ 69.7, 76.3) and three sp2 CH signals
(δ 102.0, 111.3, 117.9), six quaternary carbon signals
including one carbonyl carbon signal (δ 180.0) and five
sp2 carbon signals (δ 116.5, 143.1, 160.6, 162.9, 168.7).
All the above NMR data (Table 1) indicated that
compound 2 is a chromone derivative[4]. Comparing
the molecular formula and 13C NMR data of compound
2 with those of compound 1, it was found that compound
2 had one extra hydroxyl group and the chemical
shift of C-1 moved obviously toward downfield.
Thus, the hydroxyl group should locate at C-1. The
coupling constant of H-1 and H-2 was less than 6.0
Hz, it could be deduced that H-1 and H-2 were
erythro-form[5]. Additionally, compound 2 exhibited
negative optical rotation, C-1 and C-2 could be
determined as 1R, 2S configuration[6]. From the
above evidences, the molecular structure of 2 was
elucidated as (−)-(1R, 2S)-erythro-5-hydroxy-7-(1,
2-dihydroxypropyl)-2-methyl-chromone, which was
further confirmed by HMBC and NOESY (Figure 2)
experiments.


Figure 2 Key HMBC and NOESY of compound 2

Experimental
General NMR spectra were run on Varian
INOVA-300/600 MHz and Bruker DRX-500 MHz
spectrometers with TMS as internal standard. ESI-MS
and HR-ESI-MS were measured on a VG AutoSpec
3000 mass spectrometer. The optical rotation was
measured on a Jasco P-1020 polarimeter. Column
chromatography (CC) was carried using silica gel


Figure 1 Structures of compounds 1 − 9
SHEN Yu-xia, et al: A new chromone derivative from Berchemia lineata · 1141 ·

Table 1 NMR spectral data of compound 1 (CD3OD, J in Hz) and compound 2 (pyridine-d5, J in Hz)
1 2
Position
δH δC δH δC HMBC (H→C) ROESY
2 161.6 160.6
3 5.96 (s) 118.1 6.65 (s) 117.9 C-4, C-5, C-10
4 182.1 180.0
5 167.2 168.7
6 6.53 (d, J = 2.0) 112.6 6.68 (s) 111.3 C-4, C-5, C-7, C-8, C-9, C-10
7 143.8 143.1
8 6.56 (d, J = 2.0) 101.8 6.73 (s) 102.0 C-2, C-4, C-9, C-10
9 163.1 162.9
10 116.0 116.5
1 2.62 (dd, J = 5.1, 14.4) 44.3 4.62 (d, J = 5.4) 76.3 C-2, C-3, C-5, C-6 H-3
2.55 (dd, J = 7.9, 14.4)
2 4.10 (m) 66.5 4.37 (m) 69.7 C-1, C-3
3 1.18 (d, J = 6.2) 23.2 1.35 (d, J = 6.3) 19.5 C-1, C-2 H-1
2-CH3 2.62 (s) 23.6 2.72 (s) 23.4 C-2, C-3, C-4

(200−300 mesh), and thin-layer chromatography (TLC)
was performed on silica gel GF254 from Qingdao
Haiyang Chemical Group Co., China. RP-C18 silica
gel was purchased from YMC Co., Ltd., Japan. All
organic solvents were of analytical purity and were
purchased from Tianjin Bodi Chemical Reagent Co.,
Ltd., China. HPLC was performed on an Ultimate 3000
apparatus using 5C18-MS-II column (ODS, 250 mm ×
10 mm) and monitored with a UV detector.
Plant material The root of B. lineata was
collected in Yulin (Guangxi Province) in July, 2008, and
authenticated by professor WAN Ding-rong, College of
Pharmacy, South-Central University for Nationalities.
Extraction and isolation The dried root of B.
lineata (20.0 kg) was powdered and then extracted
with 95% EtOH for three times per 24 hours at room
temperature. The EtOH extract was then concentrated
under reduced pressure to give a residue (1.2 kg), which
was suspended with a mixture of MeOH/H2O (9∶1),
and the suspension was then extracted with petroleum
ether, EtOAc and n-BuOH. The EtOAc extract (100.0 g)
was chromatographed over a silica gel column eluting
with cyclohexane/acetone (in gradient), followed by
MeOH to yield seven fractions (F01−F07). Fraction
F04 (5.0 g) was subjected to CC on a silica gel column
using a gradient of increasing polarity with petroleum
ether/ethyl acetate to give five subfractions (F0401−
F0405). F0403 was chromatographed over a silica gel
column eluting with a gradient mixture of cyclohexane/
ethyl acetate from 95∶5 to 30∶70 to give four
subfractions (F040301−F040304). F040302 was
crystallized in acetone to give compound 9 (20 mg) as
yellow amorphous powder. F040303 was purified
over a RP-C18 silica gel column eluting with 70%
MeOH/H2O to afford compounds 4 (49 mg) and 5 (23
mg). Compound 3 (6 mg) was crystallized in acetone
as white needle crystals from F040304. Fraction F05
(4.1 g) was chromatographed over a silica gel column,
using a gradient of increasing polarity with cyclohexane
and ethyl acetate as solvents, and afforded five
subfractions (F0501−F0505). F0502 was purified
by reversed-phase preparative HPLC and yielded
compounds 6 (20 mg) and 7 (45 mg). F0505 was
purified over a RP-C18 silica gel column eluting with
MeOH/H2O (in gradient) to give four subfractions
and then F050502 was crystallized in acetone to give
compound 2 (22 mg) as colorless needle crystals.
Fraction F06 (6.0 g) was repeatedly chromatographed
over a silica gel, then purified on a RP-C18 silica gel
column to afford compounds 1 (53 mg) and 8 (30 mg).
Identification
Compound 1 Pink powders, ESI-MS m/z: 257
[M+Na]+; 1H NMR (500 MHz, CD3OD) and 13C NMR
(125 MHz, CD3OD) data see Table 1.
Compound 2 Colorless needle crystals, [α] 22D =
−50.2 (c 0.22, MeOH), ESI-MS m/z: 273 [M+Na]+,
HR-ESI-MS m/z: 273.073 7 [M+Na]+ (25) (calcd. for
C13H14O5Na, 273.0738), 400.1759 (50), 341.135 2 (58),
· 1142 · 药学学报 Acta Pharmaceutica Sinica 2010, 45 (9): 1139−1143

329.131 2 (11), 302.153 0 (58), 281.205 8 (8), 279.150 2
(15), 273.073 7 (25), 271.263 3 (7), 265.406 5 (6);
1H NMR (500 MHz, pyridine-d5) and 13C NMR (125
MHz, pyridine-d5) data see Table 1.
Compound 3 White needle crystals, ESI-MS
m/z: 295 [M+Na]+; 1H NMR (500 MHz, CD3OD) δ:
7.14 (2H, d, J = 7.0 Hz, H-2, 6), 6.65 (2H, d, J = 7.0
Hz, H-3, 5), 5.73 (1H, s, H-8), 5.70 (1H, s, H-6), 5.14
(1H, dd, J = 13.5, 3.0 Hz, H-2), 2.93 (1H, dd, J = 13.5,
19.5 Hz, H-3), 2.51 (1H, dd, J = 19.5, 3.0 Hz, H-3);
13C NMR (100 MHz, CD3OD) δ: 81.9 (C-2), 45.4 (C-3),
199.2 (C-4), 166.8 (C-5), 97.6 (C-6), 169.7 (C-7), 97.6
(C-8), 166.3 (C-9), 104.7 (C-10), 132.5 (C-1), 130.5
(C-2, 6), 160.4 (C-4), 117.7 (C-3, 5). These data
were in basic agreement with those of naringenin[7],
thus compound 3 was elucidated as naringenin.
Compound 4 White powders, ESI-MS m/z: 311
[M+Na]+; 1H NMR (600 MHz, CD3OD) δ: 6.75 (1H, s,
H-2), 6.63 (1H, d, J = 9.0 Hz, H-6), 5.71 (1H, d, J =
9.0 Hz, H-5), 5.10 (1H, dd, J = 13.2, 3.0 Hz, H-2), 2.90
(1H, dd, J = 16.8, 13.2 Hz, H-3), 2.52 (1H, dd, J = 16.8,
3.0 Hz, H-3); 13C NMR (75 MHz, CD3OD) δ: 80.7
(C-2), 44.2 (C-3), 197.9 (C-4), 165.0 (C-5), 96.3 (C-6),
169.8 (C-7), 96.3 (C-8), 165.6 (C-9), 103.4 (C-10),
131.9 (C-1), 114.8 (C-2), 147.0 (C-3), 146.6 (C-4),
116.3 (C-5), 119.4 (C-6). These data were in basic
agreement with those of eriodictyol[8], thus compound 4
was elucidated as eriodictyol.
Compound 5 Brown cluster crystals, ESI-MS
m/z: 311 [M+Na]+; 1H NMR (600 MHz, CD3OD) δ:
7.34 (2H, d, J = 7.8 Hz, H-2, 6), 6.82 (2H, d, J = 7.8
Hz, H-3, 5), 5.67 (2H, s, H-6, 8), 4.86 (1H, d, J = 11.4
Hz, H-2), 4.43 (1H, d, J = 11.4 Hz, H-3); 13C NMR (75
MHz, CD3OD) δ: 85.1 (C-2), 73.8 (C-3), 198.6 (C-4),
164.7 (C-5), 96.5 (C-6), 169.1 (C-7), 96.5 (C-8), 165.4
(C-9), 102.0 (C-10), 130.5 (C-1), 129.4 (C-2, 6), 159.3
(C-4), 116.3 (C-3, 5). These data were in good
agreement with those of aromadendrin[9], thus compound
5 was elucidated as aromadendrin.
Compound 6 Yellow oil, ESI-MS m/z: 327
[M+Na]+; 1H NMR (600 MHz, CD3OD) δ: 6.83 (1H, d,
J = 2.0 Hz, H-2), 6.66 (1H, dd, J = 2.0, 7.8 Hz, H-6),
5.78 (1H, d, J = 7.8 Hz, H-5), 5.77 (1H, s, H-8), 5.74
(1H, s, H-6), 4.88 (1H, d, J = 11.4 Hz, H-2), 4.37 (1H, d,
J = 11.4 Hz, H-3); 13C NMR (75 MHz, CD3OD) δ: 85.2
(C-2), 73.8 (C-3), 198.5 (C-4), 164.6 (C-5), 97.4 (C-6),
168.8 (C-7), 96.4 (C-8), 165.4 (C-9), 102.0 (C-10),
130.0 (C-1), 116.0 (C-2), 147.3 (C-3), 146.4 (C-4),
116.2 (C-5), 121.0 (C-6). These data were in basic
agreement with those of taxifolin[10], thus compound 6
was elucidated as taxifolin.
Compound 7 Yellow oil, ESI-MS m/z: 313
[M+Na]+; 1H NMR (600 MHz, CD3OD) δ: 6.83 (1H, d,
J = 1.8 Hz, H-2), 6.65 (1H, dd, J = 1.8, 8.4 Hz, H-6),
6.61 (1H, d, J = 8.4 Hz, H-5), 5.81 (1H, s, H-8), 5.78
(1H, s, H-6), 4.66 (1H, s, H-2), 4.02 (1H, br s, H-3),
2.72 (1H, dd, J = 16.2, 4.8 Hz, H-4), 2.60 (1H, dd, J =
16.2, 1.8 Hz, H-4); 13C NMR (75 MHz, CD3OD) δ:
80.0 (C-2), 67.6 (C-3), 29.4 (C-4), 157.5 (C-5), 96.5
(C-6), 158.1 (C-7), 96.0 (C-8), 157.8 (C-9), 100.2
(C-10), 132.4 (C-1), 115.4 (C-2), 146.1 (C-3), 146.0
(C-4), 116.0 (C-5), 119.5 (C-6). These data were in
agreement with those of catechin[11], thus compound 7
was elucidated as catechin.
Compound 8 Yellow oil, ESI-MS m/z: 329
[M+Na]+; 1H NMR (600 MHz, CD3OD) δ: 6.37 (2H, s,
H-2, 6), 5.80 (1H, s, H-8), 5.77 (1H, s, H-6), 4.61 (1H,
s, H-2), 4.02 (1H, br s, H-3), 2.70 (1H, dd, J = 16.8,
4.8 Hz, H-4), 2.59 (1H, dd, J = 16.8, 1.8 Hz, H-4);
13C NMR (75 MHz, CD3OD) δ: 79.9 (C-2), 67.6 (C-3),
29.2 (C-4), 157.4 (C-5), 96.5 (C-6), 158.0 (C-7), 96.0
(C-8), 157.7 (C-9), 100.2 (C-10), 131.6 (C-1), 107.1
(C-2), 146.8 (C-3), 133.7 (C-4), 146.7 (C-5), 107.2
(C-6). These data were in agreement with those of
epigallocatechin[11], thus compound 8 was elucidated as
epigallocatechin.
Compound 9 Yellow powders, ESI-MS m/z: 325
[M+Na]+; 1H NMR (600 MHz, CD3OD) δ: 7.56 (1H,
d, J = 1.8 Hz, H-2), 7.46 (1H, dd, J = 1.8, 8.4 Hz,
H-6), 6.71 (1H, d, J = 8.4 Hz, H-5), 6.21 (1H, s, H-8),
6.00 (1H, s, H-6); 13C NMR (75 MHz, CD3OD) δ:
148.1 (C-2), 137.4 (C-3), 177.4 (C-4), 158.4 (C-5), 99.5
(C-6), 166.0 (C-7), 94.6 (C-8), 162.6 (C-9), 104.6
(C-10), 124.3 (C-1), 116.1 (C-2), 146.4 (C-3), 149.0
(C-4), 116.1 (C-5), 121.8 (C-6). These data were in
agreement with those of quercetin[12], thus compound 9
was elucidated as quercetin.
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