全 文 :广 西 植 物 Guihaia Aug.2015,35(4):564-568 http://journal.gxzw.gxib.cn
DOI:10.11931/guihaia.gxzw201312033
黄永林,李典鹏,杨子明.红背山麻杆叶的化学成分研究 (Ⅳ)———多酚类化合物[J].广西植物,2015,35(4):564-568
Huang YL,Li DP,Yang ZM.Chemical constituents from the leaves of Alchornea trewioides(4).Polyphenols[J].Guihaia,2015,35(4):564-568
Chemical constituents from the leaves of
Alchornea trewioides(4).Polyphenols
HUANG Yong-Lin*,LI Dian-Peng,YANG Zi-Ming
(Guangxi Key Laboratory of Functional Phytochemicals Research and Utilization,
Guangxi Institute of Botany,Guilin 541006,China)
Abstract:Alchornea trewioides,as atraditional Chinese medicine,was used to aleviate ilness and discomfort in Chi-
na,but the material basis of pharmacodynamic was unknown.In order to research for the material basis of pharma-
codynamic fromA.trewioidesleaves,the fresh leaves of A.trewioides were extracted with 80%aqueous acetone
and assigned by petroleum ether and water.The petroleum ether and water extracts were subjected to the column
chromatography by MCI gel CHP 20P,Sephadex LH-20,and Toyopearl Butyl-650C,respectively,to yield nine
polyphenols.Their structures were identified by means of 1 H NMR,13C NMR,DEPT,and comparison with litera-
ture as:elagic acid(1),3-O-methylelagic acid(2),decarboxyelagic acid(3),1-O-galoyl-β-D-glucose(4),1,6-di-O-
galoyl-β-D-glucose(5),corilagin(6),phylanthusin D(7),furosonin(8),and geranin(9),respectively.Com-
pounds 2-9 were obtained fromA.trewioides for the first time.
Key words:Alchornea trewioides;chemical constituents;polyphenols;elagic acid;extraction and separation
CLC number:Q946.91,R284.1 Document code:A Article ID:1000-3142(2015)04-0564-05①
红背山麻杆叶的化学成分研究(Ⅳ)———多酚类化合物
黄永林*,李典鹏,杨子明
(广西植物功能物质研究与利用重点实验室,广西植物研究所,广西 桂林541006)
摘 要:红背山麻杆(Alchornea trewioides)为山麻杆属植物,作为传统的中药被用来减轻疾病和身体不适,
但它的药效物质基础尚未完全清楚。为了全面掌握红背山麻杆药效物质基础,采用80%丙酮对其新鲜叶进
行提取,并利用 MCI gel CHP 20P、Sephadex LH-20等色谱柱进行分离共得到9个化合物。这些化合物的结
构经氢谱与碳谱比较分析鉴定为鞣花酸(1)、3-O-甲基没食子酸(2)、decarboxyelagic acid(3)、1-O-没食子酰
基-β-D-葡萄糖(4)、1,6-二-O-没食子酰基-β-D-葡萄糖(5)、柯里拉京(6)、叶下珠鞣质D(7)、furosonin(8)、老鹳
草素(9)。其中化合物2~9均为首次从该属植物中分离得到。
关键词:红背山麻杆;化学成分;多酚;鞣花酸;提取与分离
Alchornea trewioides,as atraditional Chinese
medicine,was used to reduce ilness,discomfort,and
treated inflammation of the prostate gland,hematuria,
and other diseases in China(Jiangsu New Medical Col-
lege,1977).In previously,the polyphenols,such as
flavonoids,quinic acids,phenylethanoids,and phenol-
ic acids have been reported(Lu,2012;Qin,2012,
Huang,2013,2014,2015).However,the other main
① 收稿日期:2014-12-26 修回日期:2015-02-09
基金项目:广西自然科学基金(2011GXNSFD018038);广西科技合作与交流计划项目(桂科合1298014-10);广西植物研究所基本业务费项目(桂植业
13002);广西植物功能物质研究与利用重点实验室开放基金(ZRJJ2013-7)。
作者简介:黄永林(1974-),男,广西桂林人,博士,研究员,主要从事天然产物物质基础、生物活性及开发利用研究,(E-mail)hyl@gxib.cn。
*通讯作者
components of polyphenols have not been reported,
and the material basis of pharmacodynamic is un-
known.In order to grasp for the material basis of A.
trewioides,80%acetone extracts were subjected to the
column chromatography by MCI gel CHP 20P,Sepha-
dex LH-20,and Toyopearl Butyl-650C,respectively,
to yield nine polyphenols.Their structures were iden-
tified by means of 1 H NMR,13C NMR,DEPT and
comparison with literature.Compounds 2-9 were ob-
tained from the A.trewioides for the first time.
1 Materials and Methods
1 H-and 13C-NMR spectra were measured with a
JEOL JNM-AL 400spectrometer(Tokyo,Japan),
operating at 400MHz for 1 H,and 100MHz for 13C,
or a Bruker Avance 500spectrometer(Bruker Biospin
AG,Faelanden,Switzerland),operating at 500MHz
for 1 H,and 125MHz for 13C.Coupling constants and
chemical shifts were given in Hz and on aδ(ppm)
scale,respectively.Column chromatography was used
on MCI gel CHP 20P,Sephadex LH-20and Toyopearl
Butyl-650C.TLC was carried out on silica gel 60F254
(Merck),with formic acid-formate-toluene-ethyl(2∶
8∶2,or 1∶7∶1v/v),and sports were visualized
with a 2%ethanolic FeCl3.
The leaves of Alchornea trewioides were colected
in the Guilin Botanical Garden,Guangxi,China,in
August 2011.The sample plant was identified by
Prof.WEI Fa-Nan of Guangxi Institute of Botany,
and a herbarium specimen(2011 0920N)was deposi-
ted in the Guangxi Institute of Botany.
2 Extraction and Isolation
The smal pieces,fresh leaves of(5.35kg)were
extracted with 80%acetone for three times,at room
temperature.The filtrate was evaporated by rotary e-
vaporation to give an extract.The extract(610g)was
assigned between Et2O(1L)and H2O(3L)3times.
The part of Et2O-soluble fraction(Fr.E 5.46g)was
dissolved in EtOH and applied to a Sephadex LH-20
column(3.5cm i.d.×45cm)with 100%-0EtOH
(20%stepwise elution,each 300mL)to give five
fractions.The E-3(0.67g)was applied to a MCI gel
CHP 20Pcolumn(2.5cm i.d.×25cm)with MeOH-
H2O(0∶100-100∶0)to obtain3(70mg).The part
of water-soluble fraction was dissolved in water and
appliedto a Sephadex LH-20column(10cm i.d.×40
cm),eluting successively with H2O,20%,40%,
60%,80%,100% MeOH-H2O to yield 9fractions
(Fr.1-9).The fraction 3(6.51g)was applied by a
combination of column chromatography over Sephadex
LH-20,MCI gel CHP 20P,and Toyopearl Butyl-650C
to obtain4(45mg)and5(28mg).Fraction 6(36.0g)
was separated by MCI gel CHP 20Pcolumn chroma-
tography to give seven fractions.Fraction 6-4(2.45g)
was separated by a column chromatography over Seph-
adex LH-20column (4cm i.d.×35cm)with
MeOH-H2O(0∶100)to yield 6(2.15g).Fraction 7
(43.0g)was applied by a MCI gel CHP 20Pcolumn
with MeOH-H2O (0∶100)to aford five fractions.
Fraction 7-1was further separated by MCI gel CHP
20Pand Sephadex LH-20column to give 6(4.52g),8
(116mg).Separation of fraction 7-2using Sephadex
LH-20(3cm i.d.×50cm)with MeOH-H2O(0∶
100-100∶0),and finaly with 60%acetone to aford
7(476mg).Separation of fraction 7-3used Sephadex
LH-20,Chromatorex ODS,and Toyopearl Butyl-650C
to aford 1(14mg),2(31mg),9(6.41g).
3 Results and Analysis
Elagic acid (1) amorphous white powder,
C1 4H6O8.1 H-NMR(400MHz,DMSO)β:7.50(2H,
s,H-5,5′);13C-NMR(125MHz,DMSO)β:106.8
(C-1,1′),109.7(C-5,5′),112.6(C-6,6′),136.3
(C-2,2′),140.6(C-3,3′),148.1(C-4,4′),159.1
(C-7,7′)(Khac et al.,1990).
3-O-Methylelagic acid(2) amorphous white
powder,C15H8O8.1 H-NMR(500MHz,DMSO)β:4.03
(3H,s,3-OMe),7.43(1H,s,H-5′),7.50(1H,s,H-5,
5′);13C-NMR(125MHz,DMSO)β:60.7(C-OMe),107.1
(C-6′),110.7(C-5′),111.6(C-5),111.9
(C-1),112.5(C-6),113.1(C-1′),137.0(C-2′), 134.0(C-3′),141.6(C-3),140.9(C-2),148.1(C-
665 广 西 植 物 35卷
Fig.1 Chemical structures of compounds 1-9
4′),152.2(C-4),158.6(C-7′),158.8(C-7)(Bai et
al.,2008).
Decarboxyelagic acid(3) amorphous white
powder,C13H8O7.1 H-NMR(400MHz,CD3OD)
β:6.73(1H,d,J=8.1Hz,H-5′),7.41(1H,s,
H-5),8.42(1H,d,J=8.1Hz,H-6′);13 C-NMR
(100MHz,CD3OD)β:108.1(C-5),112.1(C-6),
112.4(C-5′),112.8(C-1′),118.5(C-1),119.1(C-
6′),133.3(C-3′),141.1(C-3),141.8(C-2′),
144.0(C-2),146.4(C-4),146.8(C-4′),163.8(C-
6)(Pfundstein et al.,2010).
1-O-Galoyl-β-D-glucose (4) amorphous
brown powder,C13H16O10.1 H-NMR(500MHz,
acetone-d6)β:3.18(1H,t,J=8.8Hz,H-4),
3.21-3.55(3H,m,H-2,3,5),3.46(1H,dd,J
=6.1,12.0Hz,H-6ax),3.64(1H,dd,J=3.9,
7654期 黄永林等:红背山麻杆叶的化学成分研究(Ⅳ)———多酚类化合物
12.0Hz,H-6eq),5.53(1H,d,J=8.5Hz,H-
1),7.23(2H,s,H-2′,6′);13C-NMR(125MHz,
acetone-d6)β:60.3(C-6),69.6(C-4),72.3(C-2),
75.6(C-5),76.1(C-3),93.4(C-1),108.9(2C,C-
2′,6′),119.4(C-1′),137.0(C-4′),144.0(2C,C-
3′,5′),165.2(C-7′)(El-Ekkawy et al.,1995).
1,6-Di-O-galoyl-β-D-glucose(5) amorphous
brown powder,C20H20O14.1 H-NMR(500MHz,
acetone-d6)β:3.21-3.75(4H,m,H-2,3,4,5),
4.42(1H,dd,J=6.5,12.0Hz,H-6ax),4.58
(1H,dd,J=2.7,12.0Hz,H-6eq),5.67(1H,
d,J=7.5Hz,H-1),7.08,7.15(each 2H,s,H-
2′,6′and 2″,6″);13 C-NMR(125MHz,acetone-
d6)β:63.3(C-6),70.3(C-4),73.6(C-2),75.1(C-
5),76.8(C-3),95.7(C-1),107.9,108.0(each
2C,C-2′,6′and 2′,6″),119.3,119.4(C-1′,1″),
136.9,137.4(C-4′,4″),143.9,144.0(each 2C,
C-3′,5′and 3″,5″),165.1,165.1(C-7′,7″)(Yan
et al.,2007).
Corilagin(6) amorphous brown powder,
C27H22O18.1 H-NMR(500 MHz,acetone-d6)β:
4.08(1H,br s,H-2),4.13(1H,dd,J=8.5,11.
0Hz,H-6ax),4.46(1H,br s,H-4),4.52(1H,
t,J=8.5Hz,H-5),4.83(1H,br s,H-3),4.91
(1H,t,J=11.0Hz,H-6eq),6.38(1H,s,H-
1),6.70(1H,s,H-ring B-5),6.84(1H,s,H-
ring C-5),7.12(2H,s,H-ring A-2,6);1 3C-
NMR(125MHz,acetone-d6)β:61.3(C-4),63.5
(C-6),68.1(C-2),69.9(C-3),74.7(C-5),93.5
(C-1),107.1(C-ring B-5),109.1(C-ring C-5),
109.8(2C,C-ring A-2,6),115.1(C-ring B-1),
115.8(C-ring C-1),119.8(C-ring A-1),124.7(C-
ring C-2),124.8(C-ring B-2),135.7(C-ring C-3),
136.3(C-ring B-3),138.5(C-ring A-4),143.9(C-
ring C-4),144.0(C-ring B-4),144.1(C-ring C-6),
144.5(C-ring B-6),145.0(2C,C-ring A-3,5),
164.6(C-ring A-7),166.5(C-ring C-6),167.9(C-
ring B-7)(Chung et al.,2003;Thitilertdecha et
al.,2010).
Phylanthusin D (7) amorphous brown
powder,C44H32O27.1 H-NMR(500MHz,acetone-
d6)β:2.19(3H,s,H-ring E-9′),2.98(1H,d,J
=15.5Hz,H-ring E-7ax′),3.47(1H,d,J=15.
5Hz,H-ring E-7eq′),4.40(1H,dd,J=7.5,10.
0Hz,H-6ax),4.78(1H,t,J=7.5Hz,H-6eq),
4.81(1H,t,J=7.5Hz,H-5),4.91(1H,br s,
H-ring E-1′),5.43(1H,br s,H-4),5.53(1H,br
s,H-3),5.56(1H,br s,H-2),6.30(1H,s,H-
ring E-3′),6.57(1H,br s,H-glc-1),6.65(1H,
s,H-ring B-3),7.07(1H,s,H-ring C-3),7.17
(2H,s,H-ring A-2,6),7.23(1H,s,H-ring D-
3);1 3C-NMR(125MHz,acetone-d6)β:31.0(C-
ring E-9′),49.1(C-ring E-7′),51.1(C-ring E-1′),
61.5(C-3),63.0(C-6),65.8(C-4),69.5(C-2),
72.3(C-5),80.0(C-ring E-5′),91.0(C-1),107.0
(C-ring C-3),108.8(C-ring E-6′),109.5(C-ring
B-3),109.8(2C,C-ring A-2,6),112.5(C-ring D-
3),114.5(C-ring C-1),116.0(C-ring D-1),116.4
(C-ring C-1),119.3(C-ring A-1),119.3(C-ring
D-2),123.5(C-ring B-2),124.5(C-ring C-2),
126.0(C-ring E-3),135.6(C-ring C-5),136.5(C-
ring D-5),136.9(C-ring B-5),139.6(C-ring A-
4),143.8(C-ring B-4),144.1(C-ring B-6),144.4
(C-ring C-6),144.6(C-ring C-4),144.7(C-ring E-
2′),145.2(2C,C-ring A-3,5),146.1(C-ring D-
6),146.8(C-ring D-4),163.9(C-ring E-10′),
164.3(C-ring D-7),164.6(C-ring A-7),165.4(C-
ring B-7),167.7(C-ring C-7),196.8(C-ring E-
4′),205.3(C-ring E-8′)(Foo et al.,1992;Yo-
shind et al.,1992).
Furosonin(8) amorphous brown powder,
C46H36O31.1 H-NMR(500 MHz,acetone-d6)β:
1.63(1H,d,J=14.0Hz,H-ring E-3ax),2.73
(1H,d,J=14.0Hz,H-ring E-3eq),3.93(1H,
dd,J=2.5,9.5Hz,H-ring F-1ax),4.09(1H,
m,H-ring F-2),4.12(1H,dd,J=5.5,9.5Hz,
H-ring F-1eq),4.16(1H,d,J=1.5Hz,H-ring
F-3),4.44(1H,t,J=10.0Hz,H-6ax),4.73
(1H,m,H-6eq),4.75(1H,s,H-ring E-1),4.91
(1H,t,J=9.0Hz,H-5),5.05(1H,s,H-ring
F-5),5.36(1H,br s,H-4),5.61(1H,br s,H-
2),5.66(1H,br s,H-3),6.53(1H,br s,H-1),
6.64(1H,s,H-ring B-3),7.07(1H,s,H-ring C-
3),7.21(2H,s,H-ring A-2,6),7.33(1H,s,
H-ring D-3);1 3C-NMR(125MHz,acetone-d6)β:
31.6(C-ring E-3),51.2(C-ring E-1),52.5(C-ring
865 广 西 植 物 35卷
书E-2),62.1(C-3),63.2(C-6),65.4(C-4),69.7
(C-2),72.6(C-5),74.4(C-ring F-1),76.4(C-ring
F-5),76.5(C-ring F-2),80.7(C-ring F-3),90.9
(C-1),97.7(C-ring E-4),98.1(C-ring E-6),98.2
(C-ring E-5),106.8(C-ring C-3),108.9(C-ring F-
4),109.6(C-ring C-3),109.8(2C,C-ring A-2,
6),110.6(C-ring D-1),113.9(C-ring D-3),114.8
(C-ring B-1),116.3(C-ring C-1),118.3(C-ring D-
2),119.0(C-ring A-1),123.5(C-ring B-2),124.6
(C-ring C-2),135.6(C-ring B-5),137.1(C-ring C-
5),138.1(C-ring D-5),139.4(C-ring A-4),144.0
(C-ring B-4),144.1(C-ring C-4),144.4(C-ring D-
6),144.5(C-ring B-6),144.7(C-ring C-6),145.1
(C-ring D-4),145.2(2C,C-ring A-3,5),164.7
(C-ring B-7),165.1(C-ring D-7),165.8(C-ring
A-7),168.1(C-ring C-7),169.9(C-ring E-7)
(Taniguchi et al.,2012).
Geranin (9) amorphous brown powder,
C41H28O27.1 H-NMR(500 MHz,acetone-d6)β:
4.33[1H,dd,J=6.0,10.5Hz,H(a)-6ax],4.
44[1H,dd,J=8.0,10.5Hz,H(b)-6ax],4.76
[1H,d,J=1.6Hz,H(b)-ring E-1′],4.80[1H,
m,H(a)-5],4.80[1H,m,H(b)-5],4.91[1H,
m,H(b)-6eq],4.94[1H,t,J=10.5Hz,H(a)-
6eq],5.19[1H,s,H(a)-ring E-1′],5.54[1H,
br s,H(a)-4],5.44[1H,br s,H(b)-4],5.50
[1H,br s,H(a)-3],5.57[1H,br s,H(b)-3],
5.58[1H,br s,H(a)-2],5.58[1H,br s,H(b)-
2],6.27[1H,d,J=1.6Hz,H(b)-ring E-3′],
6.54[1H,br s,H(b)-1],6.58[1H,s,H(a)-
1],6.58[1H,s,H(a)-ring E-3′],6.67[1H,s,
H(b)-ring C-3],6.68[1H,s,H(a)-ring C-3],
7.10[1H,s,H(b)-ring B-3],7.16[1H,s,H
(a)-ring B-3],7.21[2H,s,H(a)-ring A-2,6],
7.21[2H,s,H(b)-ring A-2,6],7.23[1H,s,H
(a)-ring D-3],7.27[1H,s,H(b)-ring D-3];1 3C-
NMR(125MHz,acetone-d6)β:46.2[C(a)-ring
E-1′],52.0[C(b)-ring E-1′],62.5[C(b)-3],
63.8[C(a)-6],63.8[C(b)-6],63.9[C(a)-3],
65.9[C(a)-4],66.0[C(b)-4],70.2[C(a)-2],
70.6[C(b)-2],72.7[C(a)-5],73.3[C(b)-5],
90.9[C(a)-1],91.8[C(b)-1],91.9[C(b)-ring
E-5′],91.9[C(b)-ring E-6′],92.4[C(a)-ring E-
6′],96.3[C(a)-ring E-5′],107.9[C(b)-ring C-
3],108.0[C(a)-ring C-3],109.8[C(b)-ring B-
3],110.6[C(a)-ring B-3],110.7[2C,C(b)-ring
A-2,6],110.9[2C,C(a)-ring A-2,6],113.4[C
(b)-ring D-3],113.5[C(a)-ring D-3],115.2[C
(b)-ring C-1],115.3[C(a)-ring C-1],115.9[C
(a)-ring D-1],117.0[C(b)-ring B-1],117.1[C
(b)-ring D-2],117.2[C(a)-ring B-1],119.5[C
(a)-ring D-2],120.1[C(b)-ring A-1],120.2[C
(b)-ring D-1],120.7[C(a)-ring A-1],124.7[C
(b)-ring B-2],124.8[C(a)-ring B-2],125.1[C
(b)-ring E-3′],125.5[C(b)-ring C-2],125.7[C
(a)-ring C-2],128.7[C(a)-ring E-3′],136.4[C
(b)-ring C-5],136.5[C(a)-ring C-5],137.2[C
(b)-ring D-5],137.7[C(b)-ring B-5],137.8[C
(a)-ring B-5],139.0[C(a)-ring D-5],139.9[C
(a)-ring A-4],140.0[C(b)-ring A-4],143.5[C
(a)-ring D-6],144.6[C(b)-ring B-4],144.9[C
(a)-ring C-6],144.9[C(b)-ring B-6],145.0[C
(a)-ring B-6],145.2[C(b)-ring C-6],145.3[C
(a)-ring B-4],145.4[C(b)-ring C-4],145.5[C
(a)-ring C-4],145.8[C(a)-ring D-4],145.9[2C,
C(a)-ring A-3,5],145.9[2C,C(b)-ring A-3,
5],147.0[C(b)-ring D-6],147.6[C(b)-ring D-
4],149.3[C(b)-ring E-2′],154.7[C(a)-ring E-
2′],164.7[C(a)-ring A-7],164.9[C(b)-ring A-
7],165.4[C(b)-ring D-7],165.5[C(a)-ring D-
7],165.6[C(a)-ring E-7′],165.8[C(b)-ring B-
7],165.9[C(b)-ring E-7′],166.2[C(a)-ring B-
7],168.4[C(b)-ring C-7],168.5[C(a)-ring C-
7],194.6[C(b)-ring E-4′],191.9[C(a)-ring E-
4′](Yoshind et al.,1992).
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