全 文 ：Ｒeceived:April 17，2013 Accepted:September 5，2013
Foundation Item:This work was financially supported by the National
Natural Science Foundation Project (No． 81260684)and the Ｒesearch
Fund for self-selected Topic of Beijing University of Chinese Medicine
(No． 2013-jybzz-xs-113)．
* Corresponding author Tel:86-10-84738629;E-mail:liubinyn67@ 163．
com
天然产物研究与开发 Nat Prod Ｒes Dev 2014，26:11-14，49
文章编号:1001-6880(2014)1-0011-05
秀丽莓茎中酚类成分研究
刁玉林1，热增才旦1，2，王如峰1，刘 斌1*
1北京中医药大学中药学院，北京 100102;2 青海大学医学院中藏药研究中心，西宁 810001
摘 要:秀丽莓(Ｒubus amabilis Focke)为蔷薇科悬钩子属植物，系常用藏药，已有 1300 多年历史。本实验从其
茎中分离了 8 个化合物，通过波谱法和理化性质分别鉴定为:4-乙酰氧基-3-甲氧基苯甲酸(1)、2-O-β-D-吡喃葡
萄糖基-6-羟基苯甲酸(2)、香草酸(3)、白藜芦醇(4)、2，6-二甲氧基-4-羟苯基-1-O-β-D-吡喃葡萄糖苷(5)、反式-
4-羟基桂皮酸(6)、咖啡酸(7)及没食子酸(8)。其中 1 为新天然产物，化合物 2 ～ 7 均为首次从该植物中分离得
到。
关键词:秀丽莓;悬钩子属;酚类;结构解析
中图分类号:Ｒ932 文献标识码:A
Phenolic Compounds from Stems of Ｒubus amabilis Focke
DIAO Yu-lin 1，ＲE-ZENG Cai-dan 1，2，WANG Ｒu-feng 1，LIU Bin 1*
1 School of Traditional Chinese Medicine，Beijing University of Chinese Medicine，Beijing 100102，P． Ｒ． China;
2The Ｒesearch Center of Chinese and Tibetan Medicine，Medicine College of Qinghai University，Xining 810001，P． Ｒ． China
Abstract:The constituents of Ｒubus amabilis were isolated and purified by silica gel column chromatography，Sephadex
LH-20，macroporous adsorption resin and TLC． The structures of the purified compounds were elucidated on the basis of
spectral data and physiochemical properties． Eight compounds were isolated and their structures were identified as:4-
acetoxy-3-methoxybenzoic acid (1) ，2-(β-D-glucopyranosyloxy)-6-hydroxybenzoic acid (2) ，vanillic acid (3) ，resvera-
trol (4) ，2，6-dimethoxy-4-hydroxyphenol-1-O-β-D-glucopyranoside (5) ，trans-4-hydroxy cinnamic acid (6) ，caffeic
acid (7)and gallic acid (8)． Compound 1 was a new natural product． Compounds 2-7 were isolated from Ｒubus amabilis
for the first time．
Key words:Ｒubus amabilis Focke;Ｒosaceae;phenolic compounds;structural elucidation
Introduction
Ｒubus，belonging to Ｒosaceae，is a large genus with
more than 750 known plants distributed all over the
world and mainly concentrated in North America and
East Asia． More than 200 different plants of this genus
grow in the mainland of China，especially in southwest-
ern China ［1］． Modern pharmacological study showed its
antibacterial ［2］，anti-inflammatory ［3］，anti-neoplastic
［4］，anti-allergic ［5］，anti-oxidative ［6］，anti-aging，free
radical scavenging ［7］，hepatic protective ［8］，analgesic
［9］，and hypolipidemic activities ［10］． The shortage of
further chemical basis research restricted the develop-
ment of this plant． The present article described the i-
solation and structural elucidation of a new natural
product named 4-acetoxy-3-methoxybenzoic acid (1) ，
as well as 7 known phenol derivatives，viz，2-(β-D-glu-
copyranosyloxy)-6-hydroxybenzoic acid (2) ，vanillic
acid (3) ，resveratrol (4) ，2，6-dimethoxy-4-hydroxy-
phenol-1-O-β-D-glucopyranoside (5) ，trans-4-hydroxy
cinnamic acid (6) ，caffeic acid (7)firstly obtained
from the stems of Ｒ． amabilis and gallic acid (8)．
(Fig． 1)
Materials and Methods
General experimental procedures
UV spectra were obtained on a UV 210A Shimadzu
spectrometer． 1H and 13C NMＲ spectra were recorded in
deuterated solvent with Bruker DＲX-500 spectrometers
Fig. 1 Chemical structures of phenol constituents (1-8)isolated from the stems of Ｒ． amabilis
operating at 500 MHz for 1H NMＲ experiments，and
125 MHz for 13C NMＲ experiment，respectively． Cou-
pling constants were expressed in Hertz (Hz) and
chemical shifts were given on a δ (ppm)scale with
tetramethylsilane as internal standard． Negative ion
ESI-MS and HＲ-ESI-MS were recorded on a VG-20-
250 and VG-ZAB-HS spectrometer (VG，Manchester，
UK)． Column chromatography separations were per-
formed using Diaion HP 2MGL (Mitsubishi Chem，Bei-
jing，China) ，AB-8 (The Chemical Plant of NanKai U-
niversity，Tianjin，China) and Silica gel (Qingdao
Haiyang Chemical Co．，Qingdao，China)as stationary
phase． TLC was carried on silica gel G precoated plates
(Qingdao Haiyang Chemical Co．，Qingdao，China)．
The TLC plate was monitored by spraying with 10%
H2SO4 solution in ethanol followed by heating．
Fungal material
The dried stems of Ｒ． amabilis were collected from
Huzhubeishan in Qinghai，China and identified by
Prof． Chunsheng Liu (Beijing University of Chinese
Medicines)． An authentic sample was kept in School of
Chinese Pharmacy，Beijing University of Chinese Medi-
cines．
Extraction and isolation
The dried stems of Ｒ． amabilis (10． 0 and 15． 0 Kg)
were powdered and extracted exhaustively with 70%
EtOH and water，respectively，under reflux． The extract
(extracted with 70% EtOH)was concentrated to the
small volume (1 g crude herbal per mL) ，and applied
on extraction with petroleum ether，chloroform，ethyl
acetate，n-butanol and water． The ethyl acetate fraction
was concentrated under reduced pressure，and the resi-
due (200 g)was subjected to column chromatography
(CC，20 × 100 cm)on macroporous adsorption resin
gradient eluted with CHCl3-MeOH to obtain two frac-
tions (Fraction 1 ∶ CHCl3-MeOH = 45 ∶ 55-30 ∶ 70 and
Fraction 2∶ CHCl3-MeOH =25∶ 75-10∶ 90)． Fraction 1，
was further fractionated on silica gel gradient eluted
with CHCl3-MeOH-H2O (9∶ 1∶ 0． 1，8． 5∶ 1． 5∶ 0． 1，8∶ 2
∶ 0． 2，7． 5∶ 2． 5 ∶ 0． 3，7∶ 3 ∶ 0． 5，6． 5 ∶ 3． 5 ∶ 0． 8，6 ∶ 4 ∶ 1
and 5∶ 5 ∶ 1) ，and ODS eluted with a step gradient of
H2O-MeOH (1∶ 0-0 ∶ 1)to give 2(10 mg)and 5(10
mg)． Fraction 2 was fractionated repeatedly on silica
gel gradient eluted with CHCl3-CH3OH (10∶ 1-0 ∶ 1) ，
to obtain 4(20 mg)from Fr 2. The residue (300 g)
extracted with water and fractioned with ethyl acetate
was subjected was subjected to CC (10 × 150cm)on
silica gel (CHCl3-MeOH，1∶ 0-0∶ 1) ，and recrystallized
to obtain 1(20 mg) ，3(50 mg) ，6 (40 mg) ，7 (15mg)
and 8(37 mg).
Structural identification
4-acetoxy-3-methoxybenzoic acid (1) was obtained
as a pale white crystal (MeOH). Bromocresol green re-
action showed yellow points in TLC indicated carboxyl
contained in the structure. UV (MeOH)λmax (log
ε) :246sh (2. 83)nm. Its mass spectrum showed a
molecular ion peak at m/z 211( ［M + H］+)consist-
ent with the molecular formula C10 H10 O5 elucidated
from 1H NMＲ，13 C NMＲ，HSQC and HMBC re-
sults. The 1H NMＲ spectrum of 1 displayed characteris-
tic signals for a substituted aromatic ring in the form of
ABX system at δ 7. 44 (1H，d，J = 1. 5 Hz，H-2) ，
7. 34 (1H，dd，J = 8. 0，1. 5 Hz，H-6)and 6. 72 (1H，
d，J = 7. 8 Hz，H-5). Two three-proton signals as a sin-
glet at δ 1. 76 (3H，s)and 3. 50 (3H，s)were attribu-
21 Nat Prod Ｒes Dev Vol. 26
ted to the protons of methyl and methoxyl，respective-
ly. The 13C NMＲ spectrum of 1 exhibited signals for a
aromatic ring at δC 113. 3 (C-2) ，114. 2 (C-5) ，122. 5
(C-6) ，129. 5 (C-1) ，146. 4 (C-3)and 148. 3 (C-4)
. The carbonyl signals appeared at δC 170. 0 and
173. 8，respectively，and one of them might be assigned
to an ester carbonyl group. In addition，the signals at δC
23. 4 and 55. 4 were assigned to -CH3 and -OCH3 car-
bons，respectively. Based on above evidence，two possi-
ble similar structures could be deduced as shown in
Fig. 2.
Fig. 2 The possible structures of compound 1: (a)4-
acetoxy-3-methoxybenzoic acid;(b)3-acetoxy-4-
methoxybenzoic acid.
The HMBC spectrum of 1 showed correlations of C-4
with δH 7. 44，7. 34 and 6. 72，and -OCH3 with δC
146. 4 and 148. 3. This demonstrated that the structure
of this compound should be structure a because there
would be no correlation of δH 7. 34 (H-6)with δC
148. 3 observed in structure b. This structure was fur-
ther confirmed by the stronger correlation signal of δH
3. 75 (-OCH3)with δC 146. 4 (Fig. 3). Additionally，
the isolation of compound 3 could further prove the given
structure. Finally，the spectra data were given in Table 1.
Table 1 1H NMＲ(500 MHz，DMSO-d6) ，
13C NMＲ (125
MHz，DMSO-d6)
* and HMBC data of compound 1
Position δH(J，Hz) δC HMBC
1 － 129. 5 －
2 7. 44 (1H，d，1. 5) 113. 3 C-4，6
3 － 146. 4 －
4 － 148. 3 －
5 6. 72 (1H，d，7. 8) 114. 2 C-1，3，4
6 7. 34 (1H，dd，8. 0，1. 5) 122. 5 C-2，4
C = O of -COOH － 173. 8 －
C = O of -COCH3 － 170. 0 －
-OCH3 3. 50 (3H，s) 55. 4 C-3，4
-CH3 1. 76 (3H，s) 23. 4 －
* Assignments were confirmed by HSQC and HMBC experiments
Fig. 3 Selective HMBC correlations for 1 and 2 (H→C)
2-(β-D-glucopyranosyloxy)-6-hydroxybenzoic acid
(2) was obtained as yellowish powder (MeOH)with
positive FeCl3 and Molish reaction results，which indi-
cated this compound may be a phenolic glycoside. The
ESI-MS (m/z 315［M-H］-，653［2M + Na］-)in com-
bination with HＲ-ESI-MS (m/z) :315. 0714［M-H］-，
calcd 315. 0716 revealed a molecular formula C14 H18
O8，suggesting the presence of six degrees of unsatura-
tion. In the 1H NMＲ spectrum of 2，three downfield
peaks at δH 6. 64 (1H，d，J = 7. 8 Hz) ，7. 07 (1H，t，J
= 7. 8 Hz)and 6. 43 (1H，d，J = 7. 8 Hz)were attrib-
uted to H-3，H-4 and H-5 in an ABC spin coupling sys-
tem，respectively. One single-proton signal at δ 4. 43
with a coupling constant of 7. 2 Hz showed the exist-
ence of a β oriented glucosyl group. Five multiplets at
δH 3. 25-3. 74 were assignable to the glucosyl group.
The 13C NMＲ spectrum of 2 exhibited the presence of
aromatic carbons at δC 112. 0 (C-1) ，160. 0 (C-2) ，
108. 9 (C-3) ，131. 3 (C-4) ，112. 1 (C-5)and 164. 0
(C-6) ，carbonyl carbon at δC 170. 9 (C = O) ，anomer-
ic carbon of the glucosyl group at δC 106. 5 (C-1)and
the remaining five carbons of glucosyl group at between
δC 61. 5 and 78. 0. The HMBC spectrum of 2 showed
correlations of H-1 with δC 160. 0，78. 0 and 76. 3，
which indicated that the glucosyl group linked the car-
bon at δC 160. 0 of the aromatic ring to form glyco-
side. The HMBC correlations showed the linkages as il-
lustrated in Fig. 3.
The 1H-1H COSY spectrum of 2 showed two sets of op-
tional spin coupling proton correlation signals (δH 4-H /
3-H and 4-H /5-H)in the aromatic ring，which con-
firmed the structure given above. Complete 1H and 13C
NMＲ assignments were accomplished by a combination
of 2D NMＲ techniques，including HMQC，HMBC，and
1H-1H COSY.
The spectra data were given as follows:1H NMＲ (in
DMSO-d6，500 MHz)δ:6. 64 (1H，d，J = 7. 8 Hz，H-
31Vol. 26 DIAO Yu-lin，et al:Phenolic Compounds from Stems of Ｒubus amabilis Focke
3) ，6. 43 (1H，d，J = 7. 8 Hz，H-5) ，7. 07 (1H，t，J =
7. 8 Hz，H-4) ，4. 43 (1H，d，J = 7. 2 Hz，H-1) ，3. 25
(1H，m，H-2) ，3. 51 (1H，m，H-3) ，3. 39 (1H，m，
H-4) ，3. 49 (1H，m，H-5) ，3. 74，3. 65 (2H，m，H-
6). 13C NMＲ (in DMSO-d6，125 MHz)δ:112. 0 (C-
1) ，160. 0 (C-2) ，108. 9 (C-3) ，131. 3 (C-4) ，112. 1
(C-5) ，164. 0 (C-6) ，170. 9 (C = O) ，106. 5 (C-1) ，
73. 9 (C-2) ，76. 4 (C-3) ，70. 4 (C-4) ，78. 0 (C-
5) ，61. 5 (C-6). ESI-MS (m/z) (negative mode) :
315［M-H］-，653 ［2M + Na］-. HＲ-ESI-MS:m/z
315. 0714 ［M-H］-(calculated for C14 H18 O8，
315. 0716).
Vanillic acid (3) was obtained as colourless needle
crystal (MeOH). 1H NMＲ (CD3OD，500 MHz)δ:
7. 56 (1H，brs，H-2) ，7. 54 (1H，d，J = 8. 8 Hz，H-6) ，
6. 82 (1H，d，J = 8. 8 Hz，H-5) ，3. 88 (3H，s，-
OCH3) ;
13C NMＲ (CD3OD，125 MHz)δ:123. 1 (C-
1) ，113. 9 (C-2) ，152. 7 (C-3) ，148. 7 (C-4) ，115. 8
(C-5) ，125. 3 (C-6) ，170. 0 (C = O) ，56. 4 (-
OCH3)．
Ｒesveratrol (4) was obtained as white crystal
(MeOH). 1H NMＲ (500 MHz，CD3OD) δ:7. 34
(2H，d，J = 8. 4 Hz，H-2，H-6) ，6. 96 (1H，d，J =
16. 2 Hz，H-α) ，6. 80 (1H，d，J = 16. 2 Hz，H-β) ，
6. 76 (2H，d，J = 8. 4 Hz，H-3，H-5) ，6. 43 (2H，d，J
=1. 8 Hz，H-2，H-6) ，6. 15 (1H，t，J = 2. 1 Hz，H-
4) ;13C NMＲ (125 MHz，CD3OD)δ:138. 6 (C-1) ，
103. 1 (C-2，6) ，157. 0 (C-3，5) ，100. 0 (C-4) ，
127. 7 (C-1) ，126. 1 (C-2，6) ，113. 9 (C-3，5) ，
155. 8 (C-4) ，124. 3 (C-α) ，126. 7 (C-β). ESI-MS
m/z 227［M-H］-.
2，6-dimethoxy-4-hydroxyphenol-1-O-β-D-glucopyr-
anoside (5) was obtained as white powder (MeOH)
with positive FeCl3 and Molish reaction.
1H NMＲ (500
MHz，CD3OD) δ:3. 69 (6H，s，2 × -OCH3) ，4. 43
(1H，d，J = 9. 0 Hz，H-1) ，6. 13 (2H，s，H-3，5) ;13 C
NMＲ(125 MHz，CD3OD)δ:129. 3 (C-1) ，154. 7 (C-
2，6) ，94. 6 (C-3，5) ，156. 3 (C-4) ，106. 2 (C-1) ，
75. 7 (C-2) ，77. 8 (C-3) ，71. 4 (C-4) ，78. 2(C-
5) ，62. 7(C-6) ，56. 8 (2 × -OCH3). ESI-MS m/z
331［M-H］-.
Trans-4-hydroxy cinnamic acid (6) was obtained
as white crystal (acetone)with positive FeCl3 and bro-
mophenol blue reaction results and mp 210 ～ 212
℃ ． 1H NMＲ(acetone-d6，500 MHz)δ:7. 55 (2H，d，J
= 8. 5 Hz，H-2，6) ，6. 90 (2H，d，J = 8. 5 Hz，H-3，
5) ，7. 61 (1H，d，J = 16. 0 Hz，H-β) ，6. 33 (1H，d，J
= 16. 0 Hz，H-α) ;13 C NMＲ (acetone-d6，125 MHz)
δ:126. 8 (C-1) ，130. 6 (C-2，6) ，116. 4 (C-3，5) ，
160. 2 (C-4) ，115. 5 (C-α) ，145. 3 (C-β) ，167. 9 (C
= O of COOH).
Caffeic acid (7) was obtained as yellow cubic crys-
tal (MeOH)with mp 223-225 ℃ . 1H NMＲ (500
MHz，DMSO-d6)δ:7. 40 (1H，d，J = 16 Hz，H-7) ，
7. 01 (1H，d，J = 1. 5 Hz，H-2) ，6. 95 (1H，dd，J =
8. 0，1. 5 Hz，H-6) ，6. 75 (1H，d，J = 8. 0 Hz，H-5) ，
6. 16 (1H，d，J = 16 Hz，H-8) ;13 C NMＲ (125 MHz，
DMSO-d6)δ:125. 7 (C-1) ，114. 6 (C-2) ，144. 6 (C-
3) ，148. 1 (C-4) ，115. 1 (C-5) ，121. 1 (C-6) ，145. 6
(C-7) ，115. 8 (C-8) ，167. 9 (C-9).
Gallic acid (8) was obtained as colourless needle
crystal (CHCl3-MeOH)with mp 235-238 ℃ . Positive
FeCl3-K3Fe(CN)6 and bromocresol green reaction re-
sults showed the existence of phenolic hydroxyl group
and carboxyl group. The same Ｒ f values were obtained
with gallic acid reference substance in different solvent
systems. 1H NMＲ (500 MHz，CD3OD)δ:7. 05 (2H，
s，H-2，6) ;13 C NMＲ (125 MHz，CD3OD)δ:121. 9
(C-1) ，110. 3 (C-2，6) ，146. 3 (C-3，5) ，139. 5 (C-
4) ，170. 4 (C = O of COOH).
Ｒeferences
1 Chinese Herbal Editorial Committee． Flora of China． Beijing:
Beijing Science and Technology Press，1985． Vol 37:210-
218．
2 Puupponen PＲ，Nohynek L，Alakomi HL，et al． The action of
berry phenolics against human intestinal pathogens． BioFac-
tors，2005，23:243-251．
3 Choi J，Lee KT，Ha J，et al． Antinociceptive and antiinflam-
matory effects of Niga-ichigoside F1 and 23-hydroxytormentic
acid obtained from Ｒubus coreanus． Biol Pharm Bull，2003，
26:1436-1441．
4 Lee JH，Ham YA，Choi SH，et al． Activity of crude extract of
Ｒubus crataegifolius roots as a potent apoptosis inducer and
DNA topoisomerase I inhibitor． Arch Pharmacol Ｒes，2000，
23:338-343．
( 下转第 49 页)
41 Nat Prod Ｒes Dev Vol. 26
呈阳性。1H NMＲ (400 MHz，DMSO-d6) δ:12. 21
(1H，s，1-COOH) ，9. 16 (2H，s，3，5-OH) ，8. 82
(1H，s，4-OH) ，6. 91 (2H，s，2，6-H)。上述理化性
质、波谱数据与文献［10］报道的 3，4，5-三羟基苯甲酸基
本一致，故鉴定该化合物为 3，4，5 -三羟基苯甲酸。
化合物 8 无色针晶，三氯化铁-铁氰化钾反应
呈阳性。1H NMＲ (400 MHz，DMSO-d6) δ:9. 15
(3H，s，1，3，5-OH) ，6. 92 (3H，s，2，4，6-H)。上述
理化性质、波谱数据与文献［11］报道的间苯三酚基本
一致，故鉴定该化合物为间苯三酚(phloroglucinol)。
化合物 9 白色针状结晶，Liebermann- Bur-
chard反应阳性。与对照品 β-谷甾醇共 TLC，三种溶
剂系统展开 Ｒf 一致，混合后测定熔点不下降。故该
化合物鉴定为 β-谷甾醇 (β-sitosterol)。
化合物 10 白色粉末，Liebermann-Burchard 反
应及 Molish 反应均为阳性。与胡萝卜苷对照品共
TLC，三种溶剂系统展开 Ｒf 都一致，混合后测定熔
点不下降。故该化合物鉴定为胡萝卜苷 (daucoste-
rol)。
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94Vol. 26 王业玲等:红背桂花化学成分研究