全 文 ： 406 Chin J Nat Med Nov. 2011 Vol. 9 No. 6 2011 年 11 月 第 9 卷 第 6 期

Chinese Journal of Natural Medicines 2011, 9 (6): 0406−0409
doi: 10.3724/SP.J.1009.2011.00406
Chinese
Journal of
Natural
Medicines







Chemical Constituents of Boea hygrometrica
FENG Wei-Sheng1*, LI Yuan-Jing1, ZHENG Xiao-Ke2, WANG Yan-Zhi1, SU Fang-Yi1
1School of Pharmacy, Henan College of Traditional Chinese Medicine, Zhengzhou 450008, China;
2College of Basic Medicine, Henan College of Traditional Chinese Medicine, Zhengzhou 450008, China
Available online 20 Nov. 2011
[ABSTRACT] AIM: To study the chemical constituents of Boea hygrometrica (Bunge.) R. Br.. METHODS: The compounds were
isolated and purified by Diaion HP-20, Toyopearl HW-40, silica gel column chromatography and the structures were identified on the
basis of spectral data and physiochemical properties. RESULTS: Seven compounds were obtained and identified as 5,7,3′4′-tetrahy-
droxy-6-methoxy-8-C-[β-D-xylopyranosyl-(1→2)]-β-D-glucopyranosyl flavone (1), p-hydroxy phenethylalcohol (2), 3,4-dihydroxy
phenethylalcohol (3), apocynin (4), ferulic acid (5), 1′-O-β-D-(3,4-dihydroxy)-ethyl-6′-O-trans-caffeoyl-β-D-apiofuranosyl-(1→3′)-
glucopyranoside (6), gentisic acid (7). CONCLUSION: Compound 1 was a new c-glycoside flavonal and compounds 2-7 were iso-
lated from this plant for the first time.
[KEY WORDS] Boea hygrometrica (Bunge.) R.Br.; C-glycosylflavones; Phenolic acid
[CLC Number] R284.1 [Document code] A [Article ID] 1672-3651(2011)06-0406-04

1 Introduction
Boea Comm.ex Lam consists of about 20 species in the
world, among which about 3 are in China. Boea hygrometrica
(Bunge.) R. Br., a traditional Chinese herb, is widely distrib-
uted in China, and has some efficacies such as invigorating
the circulation of blood, eliminating stasis activate blood
circulation, hemostasis [1], etc. Studies on modern pharma-
cology demonstrated that it has functions such as antibiosis [2],
anti-inflammation [3]. However, few of the phytochemical
studies of the plant have been reported previously. In this
paper, seven compounds were isolated from the 50% aqueous
acetone extract of the plant.
2 Results and Discussion
Seven compounds were obtained and identified as 5, 7,
3′4′-tetrahydroxy-6-methoxy-8-C-[β-D-xylopyranosyl-
(1→2)]-β-D-glucopyranosyl flavone (1), p-hydroxy phene-
thylalcohol (2), 3, 4-dihydroxy phenethylalcohol (3), apo-
cynin (4), ferulic acid (5), 1′-O-β-D-(3,4-dihydroxy)-ethyl-

[Received on] 23-Dec.-2010
[Research funding] This project was supported by the Key Project
of Chinese Ministry of Education (No. DF2003078)
[*Corresponding author] FENG Wei-Sheng: Prof., Tel: 86-371-
65680011, Fax: 86-371-65680011, E-mail: fwsh@hactcm.edu.cn
These authors have no any conflict of interest to declare.
6′-O-trans-caffeoyl-β-D-apiofuranosyl-(1→3′)-glucopyrano-
side (6), gentisic acid (7).
Compound 1 was isolated as a yellow amorphous pow-
der, mp 154–156 °C, [α]20 D –84.33 (c 0.2, MeOH), and UV
(MeOH) λmax: 272.1 nm, 350.2 nm. The molecular formula of
1 was determined as C27H30O16 by the HR-ESI-MS (m/z
611.161 0 [M + H]+, calcd. for C27H30O16H 611.161 2). In its
IR (KBr) spectrum, absorption bands for hydroxyl (3 386
cm–1) and carbonyl (1 650 cm–1) groups, as well as aromatic
rings (1 602, 1 570, 1 523, 1 456 cm–1). 1H NMR spectrum
showed the presence of four aromatic proton signals. Three
aromatic protons resonated at δH 7.47 (1H, d, J = 1.8 Hz,
H-2′), 7.44 (1H, dd, J = 8.1, 1.8 Hz, H-6′), and 6.85 (1H, d,
J = 8.1 Hz, H-5′) as one ABX system of B-ring, and the other
one resonated at δH 6.38 (1H, s, H-3). In addition, signals of
16 other protons were found in the range of δH 2.60-5.18.
This suggested that there existed two sugars and one meth-
oxyl group at δH 3.81 (3H, s). The anomeric protons of the
two sugars at δH 5.18 (1H, d, J = 10.0 Hz, H-1′′) and 4.21
(1H, d, J = 10.0 Hz, H-1′′′) were assigned to H-1 of
β-D-glucopyranosyl and β-D-xylopyranosyl, respectively [4].
Since acid hydrolysis of 1 afforded only xylose, this indicated
that the glucose was linked to the aglycone with C-C bond.
13C NMR spectrum (Table 1) clearly showed 27 carbon sig-
nals, including 15 of flavonol aglycone, 6 of glucose, 5 of
xylose, and 1 of methoxyl.
FENG Wei-Sheng, et al. /Chinese Journal of Natural Medicines 2011, 9 (6): 406−409
2011 年 11 月 第 9 卷 第 6 期 Chin J Nat Med Nov. 2011 Vol. 9 No. 6 407

Table 1 1H NMR (400 MHz) and 13C NMR (100 MHz) data
of compound 1 (CD3OD, δ)
No. δH δc HMBC
2 165.6
3 6.38 (1H, s) 102.1 C-2, C-4, C-10, C-1
4 183.1
5 152.7
6 134.9
7 155.5
8 105.9
9 167.0
10 106.7
1 123.4
2 7.47 (1H, d, J = 1.8 Hz) 114.0
C-2, C-3, C-4,
C-6
3 147.9
4 153.0
5 6.85 (1H, d, J = 8.1 Hz) 117.0 C-1, C-3, C-4
6 7.44 (1H, dd, J = 8.1, 1.8 Hz) 120.5 C-2, C-4
OCH3 3.81 (3H, s) 60.5
Glc
1 5.18 (1H, d, J = 10.0 Hz) 74.5
C-1, C-7,
C-9, C-2
2 4.39 (1H, t, J = 9.1 Hz) 80.8 C-8
3 3.73 (1H m) 80.4
4 3.67 (1H m) 72.4
5 3.50 (1H m) 82.7
6 3.94 (m, 1H), 3.85 (m, 1H) 63.4
Xyl
1 4.21 (d, 1H, J = 10.0 Hz) 106.5 C-2
2 3.00 (d, 1H, J = 7.6 Hz) 75.0
3 3.18 (m, 1H) 77.0
4 3.16 (m, 1H) 70.6
5 3.27 (m, 1H), 2.63 (m, 1H) 66.5



Fig.1 The chemical structure and selected HMBC correla-
tions of compound 1

In HMBC spectrum of 1, significant correlations were
found H-2′ (δH 7.47) with C-2 (δC 165.6), C-3′ (δC 147.9),
C-4′ (δC 153.0) C-6′ (δC 120.5); H-5′ (δH 6.85) with C-1′ (δC
123.4), C-3′ (δC 147.9), C-4′ (δC 153.0); H-6′ (δH 7.44) with
C-2′ (δC 114.0), C-4′ (δC 153.0); H-3 (δH 6.38) with C-2 (δC
165.6), C-3 (δC 102.1), C-4 (δC 183.1), C-10 (δC 106.7), C-1′
(δC 123.4); H-1′′ (δH 5.18) with C-7 (δC 155.5), C-9 (δC
167.0), C-2′′ (δC 80.8), C-5′′ (δC 82.7), C-1′′′ (δC 106.5); H-2′′
(δH 4.39) with C-8 (δC 105.9); H-1′′′ (δH 4.21) with C-2′′ (δC
80.8), C-5′′′ (δC 80.8). In DEPT 135 spectrum, two signals
C-6′′ (δC 63.4) and C-6′′′ (δC 66.5) showed negative signals,
indicating that both were secondary carbons. Based on the
above data, we know that the xylose moiety was connected to
the glucosyl moiety at C-2′′ position according to the shifted
signal of C-2′′(δC 80.8) and to HMBC correlation H-1′′′ /
C-2′′, indicating that the xylose and glucose connected in
1→2 linkage mode. Furthermore the proton (H-2′′) of the
glucose was correlated to C-8 (δC 105.9) of the flavone. Thus,
according to the literature [4], the structure of 1 was deter-
mined to be 5,7,3′4′-tetrahydroxy-6-methoxy-8-C-[β-D-xylo-
pyranosyl- (1→2)]-β-D-glucopyranosyl flavone.
3 Experimental
3.1 General
Kofler micro-melting point apparatus (uncorrected),
Shimadzu PC 8201 IR spectrometer, APEX II mass spec-
trometer were employed to measure the melting points, IR
spectra and MS, respectively. NMR spectra were measured
on Bruker DPX-400 instrument with TMS as the internal
standard. Silica gel (Qingdao Marine Chemical Co., Ltd.),
Diaion HP-20 and Toyopearl HW-40 (Japanese Mitsubishi)
were used for column chromatography. All solvents were of
chemical or analytical grade (Tianjin Chem Ind. Co.).
3.2 Plant material
The fresh whole plants of Boea hygrometrica (Bunge.) R.
Br. were collected from Xixia County, Henan Province,
China, in July, 2009, and identified by Prof. DONG
Cheng-Ming of Henan University of Traditional Chinese
Medicine. The voucher specimen (JB20090725) is deposited
in our laboratory.
3.3 Extraction and isolation
The whole plants (5.0 kg) of Boea hygrometrica (Bunge.)
R.Br. were extracted by 50% aqueous acetone two times at
room temperature and filtered. The combined filtrates were
concentrated under reduced pressure in a vacuum evaporator
to obtain the gross extracts (300 g). They were dissolved in
water and then subjected to Diaion HP-20 porous polymer
resin and eluted with water, 10% MeOH, 20% MeOH, 30%
MeOH, 40% MeOH, 50% MeOH, 60% MeOH, successively.
The fraction eluted with H2O was subjected to Toyopearl
HW-40 column chromatography and eluted with H2O, 10%
MeOH, 20% MeOH, 30% MeOH, 40% MeOH, 50% MeOH,
60% MeOH successively to afford subfractions. Then the
subfractions were isolated and purified by Sephadex LH-20,
Toyopearl HW-40, silica gel column chromatography and
FENG Wei-Sheng, et al. /Chinese Journal of Natural Medicines 2011, 9 (6): 406−409
408 Chin J Nat Med Nov. 2011 Vol. 9 No. 6 2011 年 11 月 第 9 卷 第 6 期

recrystallization to yield compounds 1 (20 mg), 2 (12 mg), 3
(13 mg), 4 (17 mg), 5 (10 mg), 6 (15 mg) and 7 (10 mg).
4 Identification
Compound 1 Amorphous yellow powder, mp
154-156° C, [α]20 D -84.33 (c 0.2, MeOH), HR-ESI-MS (m/z
611.1610 [M + H]+, calcd. for C27H30O16H 611.161 2). 1H
NMR (400 MHz, CD3OD) δ: 6.38 (1H, s, H-3), 7.47 (1H, d, J
= 1.8 Hz, H-2′), 6.85 (1H, d, J = 8.1 Hz, H-5′), 7.44 (1H, dd,
J = 8.1, 1.8 Hz, H-6′), 5.18 (1H, d, J = 10.0 Hz, H-1′′) , 4.21
(1H, d, J = 10.0 Hz, H-1′′′), 3.81(3H, s, OMe); 13C NMR
(100 MHz, CD3OD) δ: 165.6 (C-2), 102.1 (C-3), 183.4
(C=O), 152.7 (C-5), 134.9 (C-6), 155.5 (C-7), 105.9 (C-8),
167.0 (C-9), 106.7 (C-10), 123.4 (C-1′), 114.0 (C-2′), 147.9
(C-3′), 153.0 (C-4′), 117.0 (C-5′), 120.5 (C-6′), 74.5 (C-1′′),
80.8 (C-2′′), 80.4 (C-3′′), 72.4 (C-4′′), 82.7 (C-5′′), 63.4
(C-6′′), 106.5 (C-1′′′), 75.0 (C-2′′′), 77.0 (C-3′′′), 70.6 (C-4′′′),
66.5 (C-5′′′), 60.5 (OMe). Compound 1 was identified as
5,7,3′4′-tetrahydroxy-6-methoxy-8-C-[β-D-xylopyranosyl-
(1→2)]-β-D-glucopyranosyl flavone.
Compound 2 Amorphous white powder, 1H NMR (400
MHz, Acetone-d6) δ: 6.74 (2H, d, J = 8.4 Hz, H-2, 6), 7.04
(2H, d, J = 8.4 Hz, H-3, 5), 2.71 (2H, t, H-7), 3.68 (2H, t,
H-8). 13C NMR (100 MHz, Acetone-d6) δ: 156.3 (C-1), 130.6
(C-4), 130.5 (C-3, 5), 115.6 (C-2, 6), 39.1 (C-7), 64.0 (C-8).
Compound 2 was identified as p-hydroxy phenethylalcohol
by comparison of the physical and spectral data with the re-
ported data [5].
Compound 3 Amorphous white powder, 1H NMR (400
MHz, Acetone-d6 ) δ: 3.68 (2H, t, J = 7.2 Hz, H-7), 2.64 (2H,
t, J = 7.2 Hz, H-8), 6.71 (1H, d, J = 8.0 Hz, H-5), 6.70 (1H, d,
J = 2.0 Hz, H-2), 6.54 (1H, dd, J = 8.0, 2.0 Hz, H-6). 13C
NMR (100 MHz, Acetone-d6) δ: 131.7 (C-1), 115.7 (C-2),
145.5 (C-3), 144.0 (C-4), 116.7 (C-5), 120.8 (C-6), 39.5
(C-7), 64.1 (C-8). Compound 3 was identified as 3,
4-dihydroxy phenethylalcoholby comparison of the physical
and spectral data with the reported data [6].
Compound 4 White needles, 1H NMR (400 MHz,
Acetone-d6 ) δ: 2.50 (3H, s), 3.90 (3H, s), 6.90 (1H, d, J = 8.2
Hz, H-5), 7.52 (1H, d, J = 1.5 Hz, H-2), 7.56 (1H, dd, J = 8.2,
1.5 Hz, H-6). 13C NMR (100 MHz, Acetone-d6) δ: 130.3
(C-1), 111.3 (C-2), 148.2 (C-3), 152.4 (C-4), 115.2
(C-5),124.2 (C-6), 196.0 (C-7), 26.1 (C-8), 56.0 (OCH3).
Compound 4 was identified as apocynin by comparison of
the physical and spectral data with the reported data [7].
Compound 5 White needles, 1H NMR (400 MHz,
Acetone-d6 ) δ: 7.17 (1H, d, J = 1.7 Hz, H-2), 6.89 (1H, d, J =
8.2 Hz, H-5), 7.06 (1H, dd, J = 8.2, 1.7 Hz, H-6), 7.57 (1H, d,
J = 15.9 Hz, H-7), 6.32 (1H, d, J = 15.9 Hz, H-8), 3.91 (3H, s,
OCH3). 13C NMR (100 MHz, Acetone-d6) δ: 127.5 (C-1),
116.2 (C-2), 146.1 (C-3), 148.3 (C-4), 123.2 (C-5), 115.8
(C-6), 145.7 (C-7), 114.9 (C-8), 167.9 (C-9). Compound 5
was identified as ferulic acid by comparison of the physical
and spectral data with the reported data [8].
Compound 6 Amorphous yellow powder, 1H NMR
(400 MHz, D2O) δ: 7.53 (1H, d, J = 16.0 Hz, H-7′) , 6.27 (1H,
d, J = 16.0 Hz, H-8′), 7.05 (1H, s, H-2′), 6.97 (1H, d, J = 8.0
Hz, H-5′), 6.73 (1H, s, H-6′), 6.81 (1H, d, J = 8.0 Hz, H-2),
6.71 (1H, s, H-5), 6.62 (1H, d, J = 8.0 Hz, H-6), 2.70 (2H, t,
H-7), 3.94 (1H, m, H-8 ), 3.63 (1H, m, H-8), 5.10 (1H, d,
H-1′′′), 4.36 (1H, d, J = 8.1 Hz, H-1′′). 13C NMR (100 MHz,
D2O) δ: 131.7 (C-1), 116.5 (C-2), 144.7 (C-3), 142.7 (C-4),
117.0 (C-5), 121.5 (C-6), 34.7 (C-7), 71.4 (C-8), 123.2 (C-1′),
116.2 (C-2′), 144.2 (C-3′), 147.7 (C-4′), 124.6 (C-5′), 127.1
(C-6′), 147.2 (C-7′), 115.4 (C-8′), 102.2 (C-1′′), 73.9 (C-2′′),
81.6 (C-3′′), 69.1 (C-4′′), 73.6 (C-5′′), 60.4 (C-6′′), 110.2
(C-1′′′), 77.4 (C-2′′′), 80.0 (C-3′′′), 73.8 (C-4′′′), 63.6 (C-5′′′).
Compound 6 was identified as 1′-O-β-D-(3,4-dihydroxy)-
ethyl-6′-O-trans-caffeoyl-β-D-apiofuranosyl-(1→3′)-glucop-
yranoside by comparison of the physical and spectral date
with the reported data [9].
Compound 7 Amorphous yellow powder (MeOH), 1H
NMR (400 MHz, Acetone-d6) δ: 7.13 (1H, d, J = 2.0 Hz,
H-6), 6.69 (1H, d, J = 8.0 Hz, H-3), 6.75 (1H, dd, J = 2.0, 8.0
Hz, H-4); 13C NMR (Acetone-d6, 100 MHz) δ: 115.6 (C-2),
149.7 (C-5), 119.4 (C-6), 117.3 (C-1), 122.2 (C-4), 117.5
(C-3). Compound 7 was identified as gentisic acid by compa-
rison of the physical and spectral data with the reported data [10].
Acknowledgments
We are grateful to Prof. DONG Cheng-Ming for collect-
ing and identifying the plant material, and thanks Prof.
KANG Jian-Xun and ZHU Wei-Guo for recording the NMR
spectra.
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Pharm Sin, 2008, 43 (12): 1208-1210.

旋蒴苣苔的化学成分
冯卫生 1*，李原京 1，郑晓珂 2，王彦志 1，苏芳谊 1
1河南中医学院药学院，郑州 450008;
2河南中医学院基础医学院，郑州 450008
【摘 要】 目的：研究旋蒴苣苔全草(Boea hygrometrica (Bunge.) R.Br.) 的化学成分。方法：利用 Diaion HP-20，Toyopearl
HW-40，硅胶等柱色谱技术进行分离纯化，根据化合物的光谱数据和理化性质鉴定结构。结果：分离并鉴定了 7 个化合物的结
构，即 5,7,3,4-四羟基-6-甲氧基-8-C-[β-D-木糖-(1→2)]-β-D-葡萄糖黄酮碳苷(1)，对羟基苯乙醇(2)，3,4-二羟基苯乙醇(3)，罗布
麻宁(4)，阿魏酸(5)，1′-O-β-D-(3,4-二羟基苯乙基)-6′-O-咖啡酰基-β-D-芹菜糖(1→3′)-葡萄糖苷(6)，龙胆酸(7)。结论：化合物 1
为新化合物，化合物 2-7 为首次从该植物中分离得到。
【关键词】 旋蒴苣苔；黄酮碳苷；酚酸

【基金项目】 教育部科学技术研究重点项目（No. DF2003078）



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