全 文 ：中国特有药用植物铁破锣中的新皂甙类成分
鞠建华1＊　刘　东1　林　耕1　许旭东1　杨峻山1＊　涂光忠2　马立斌2
(1.中国协和医科大学中国医学科学院药用植物研究所 , 北京 100094;2.北京微量化学研究所 , 北京 100060)
摘要:　从铁破锣(Beesia calthaefolia(Maxim.)Ulbr.)根茎中分离得到 5个化合物(1～ 5),经化学和波谱学方法鉴定 ,
其中2 个为有机酸———铁破锣酸(beesic acid , 9_phenyl_2E , 4E , 6E , 8E_nontetraenoic acid , 1)和香草酸(2);3 个为齐墩
果酸型三萜皂甙:oleanolic acid_3_O_α_L_arabinopyranosyl_28_O_α_L_rhamnopyranosyl_(1※4)_β_D_glucopyranosyl_(1※6)_β_
D_glucopyranosyl ester(3), hederasaponin B(oleanolic acid_3_O_α_L_rhamnopyranosyl_(1※2)_α_L_arabinopyranosyl_28_O_α_L_
rhamnopyranosyl_(1※4)_β_D_glucopyranosyl_(1※6)_β_D_glucopyranosyl ester , 4)和铁破锣皂甙 Q(beesioside Q , oleanolic
acid_3_O_β_D_glucopyranosyl_(1※3)_α_L_rhamnopy ranosyl_(1※2)_α_L_arabinopyranosyl_28_O_α_L_rhamnopyranosyl_(1※4)_β_
D_glucopyranosyl_(1※6)_β_D_glucopyranosy l ester , 5)。化合物 1系首次从自然界中分离得到 , 化合物 5 为新化合物。
关键词:　毛茛科;铁破锣;齐墩果酸型三萜皂甙;铁破锣酸;铁破锣皂甙Q
中图分类号:R914　　　文献标识码:A　　　文章编号:0577-7496(2001)09-0983-05
New Triterpenic Glucoside from Beesia calthaefolia
(Maxim.)Ulbr.Native to China
JU Jian_Hua1＊ , LIU Dong1 , LIN Geng1 , XU Xu_Dong1 , YANG Jun_Shan1＊ ,
TU Guang_Zhong2 , MA Li_Bin2
(1.Institute of Medicinal Plant Development , Chinese Academy of Medical Sciences and Peking Union Medical College , Bei jing 100094 , China;
2.Beijing Institute of Microchemistry Research , Beijing 100060, China)
Abstract:　Five compounds(1-5)were isolated from the rhizome of Beesia calthaefolia (Maxim.)Ulbr.
Based on chemical and spectral evidence , their structures were determined as beesic acid(9_phenyl_2E , 4E ,
6E , 8E_nontetraenoic acid , 1), vanillic acid (2), oleanolic acid_3_O_α_L_arabinopyranosyl_28_O_α_L_
rhamnopyranosyl_(1 ※4)_β_D_glucopyranosyl_(1 ※ 6)_β_D_glucopyranosyl ester (3), hederasaponin B(oleanolic acid_3_O_α_L_rhamnopyranosyl_(1※2)_α_L_arabinopyranosyl_28_O_α_L_rhamnopyranosyl_(1※4)_β_D_glucopyranosyl_(1※6)_β_D_glucopyranosyl ester , 4)and beesioside Q(oleanolic acid_3_O_β_D_glucopy-
ranosyl_(1※3)_α_L_rhamnopyranosyl_(1※2)_α_L_arabinopyranosyl_28_O_α_L_rhamnopyranosyl_(1※4)_β_D_
glucopyranosyl_(1※6)_β_D_glucopyranosyl ester , 5), respectively .Compound 1 was isolated from natural
sources for the first time and compound 5 was a new compound.
Key words:　Ranunculaceae;Beesia calthaefolia;oleanane_type glycoside;beesic acid;beesioside Q
　　Beesia calthaefolia (Maxim.)Ulbr.(Ranuncu-
laceae)is widely distributed in southwest and northwest of
China.As a well_known Chinese folk herb medicine , it
possesses the functions of anti_inflammation , antipyretic ,
analgesia , detoxification and of invigorating blood circula-
tion.Its rhizome or the whole plant is used to treat cold ,
rheumatic arthritis , dysentery , sore throat , headache ,
etc[ 1] .Previous phytochemical research resulted in the
isolation of four highly oxygenated 9 , 19_cyclolanostane
triterpenic glycosides , namely beesioside Ⅰ-Ⅳ[ 2-5] .
For a continuation of our previous study[ 6 ,7] of the
constituents such as triterpenoids , sterols , 9 ,19_cy-
clolanostane triterpenic glycosides , etc., we isolated oth-
er two organic acids and three oleanane_type triterpenic
glycosides from the ethanol extract of the dried rhizomes of
Beesia calthaefolia.We report herein the structure eluci-
dation of these compounds.
1　Results and Discussion
Beesioside Q(5)showed a quasimolecular ion peak
at m/ z 1 405(M+K)+ , 1 389(M+Na)+ , 1 367(M
+H)+ in the ESI_MS , and the molecular formula
C65H106O30 was obtained by combined analysis of
1H-NMR
and 13C-NMR spectra.The IR spectrum exhibited absorp-
tion bands at 3 600-3 100 , 1 735 , 1 640 , 1 090 , 1 050
cm-1.The 1H-NMR spectrum showed the presence of six
anomeric proton signals(δ6.17(1H , d , J =8.0 Hz),
6.12(1H , brs), 5.77(1H , brs), 5.39(1H , d , J =
5.7 Hz), 4.94(1H , d , J =8.0 Hz), 4.75(1H , d ,
J =6.8 Hz)).The 13C_NMR spectrum showed the pres-
ence of six anomeric carbon signals(δ106.48 , 105.16 ,
104.63 , 102.59 , 101.44 , 95.53).The correlation
Received:2000-12-20　Accepted:2001-03-22
Supported by the National Natural Science Foundation of China(29732040).
＊Author for correspondence.
植　物　学　报　2001 , 43(9):983-987 　 　 　 　 　 　 　
Acta Botanica Sinica
Fig.1.　Structures of compounds 1-5.
Fig.2.　Key correlations observed in HMBC of beesioside Q.
between each anomeric proton and its corresponding
anomeric carbon signal was also observed in the HMQC
spectrum.The above evidence suggested that compound 3
was a hexaglycoside.
The 1H_NMR spectrum showed the presence of seven
singlet methyl protons (δ0.83 , 1.85 , 0.86 , 1.03 ,
1.09 , 1.20 , 1.27), a trisubstituted olefinic proton (δ
5.36(t_like))and a methine proton signal(δ3.23(dd ,
J =11.0 , 4.0 Hz))in the aglycone moiety , which are
characteristic of an oleanane_type triterpene.A compari-
son of the 13C_NMR spectrum of the aglycone moiety of
compound 3 with that of oleanolic acid[ 8] revealed that C_
3 and C_28 of compound 3 exhibited remarkable glycosi-
dation shifts(δ)by +10.4 and +3.7 , indicating that
these two positions were linked with two sugar chains.
The ratio (3∶2∶1)of the three kinds of sugars(D_
glucose , L_rhamnose and L_arabinose)was established
by analysis of each group proton signals belonging to each
sugar moiety in the 1H_1H TOCSY spectrum.Two doublet
methyl protons(δ1.49 (3H , d , J =6.0 Hz , CH3),
1.63 (3H , d , J = 6.1 Hz , CH3))assignable to two
L_rhamnose moieties in the 1H_NMR spectrum supported
the above conclusion.Based on the 1H_1H COSY , 1H_1H
TOCSY , HMQC and HMQC_TOCSY spectra , all the 1H-
NMR and
13
C_NMR signals could be completely assigned(Tables 1 , 2).In the HMBC spectrum , the long_range
correlations were observed between each anomeric proton
signal and the sugar_linked carbon as shown in Fig.2.
Therefore , the sequence and binding sites of each sugar
were determined , which were substantiated by the frag-
ment ions at m/ z 1 205 (M-162+H)+ , 1 081(M-
162-146+Na)+ , 949(M-162-146-132+Na)+ ,
803(M-162-146-132-146+Na)+ in the ESI_MS.
A β_configuration at the anomeric position could be
inferred from the coupling constants for the three glucopy-
ranosyl units(J =5-8 Hz), whereas the α_configuration
at the anomeric position could be deduced from the cou-
pling constants for both the two rhamnopyranosyl units(J=0 Hz)and arabinopyranosyl unit (J =6.8 Hz).Ac-
cordingly , compound 5 was established to be oleanolic
acid_3_O_β_D_glucopyranosyl_(1 ※3)_α_L_rhamnopyra-
nosyl_(1※2)_α_L_arabinopyranosyl_28_O_α_L_rhamnopy-
ranosyl_(1 ※4)_β_D_glucopyranosyl_(1 ※6)_β_D_glu-
copyranosyl ester , named beesioside Q.
Beesic acid (1)was obtained as yellow powder(Me2CO), with mp of 220-224 ℃.Its IR spectrum in-
dicated the presence of hydroxy (3 600-3 300 cm-1),
conjugated carboxy (1 675 cm-1), conjugated double
bond (1 615 cm-1)and mono_substituted benzene ring
(1 595 , 1 565 , 1 445 , 750 , 690 cm-1).The UV spec-
trum of compound 1 exhibited absorption bands at λMeOHmax
342 , 350 , 368 nm , which suggested that compound 1
was an unsaturated aromatic acid.The EI_MS gave the
peak of molecular ion at m/ z 226(M+ , 100)consistent
with a molecular formula of C15H14O2 , confirmed by 1H-
NMR and
13
C_NMR spectra (Table 3).
984　 植　物　学　报　　Acta Botanica Sinica 43 卷
Table 1　1H_NMR(500MHz)and 13C_NMR(125 MHz)spectral
data of the aglycone moieties of compounds 3-5 in pyridine_d5
Position
Compound 3 Compound 4 Compound 5
δH (J in Hz) δC δH (J in Hz) δC δH (J in Hz) δC
1 38.85 38.92 38.89
2 26.59 26.43 26.54
3 3.31(dd ,
11.6 , 4.3)
88.71 3.16(dd ,
11.0 , 4.0)
88.79 3.23(dd ,
11.0 , 4.0)
88.69
4 39.52 39.44 39.50
5 55.91 55.92 55.94
6 18.53 18.54 18.46
7 33.11 33.09 33.06
8 39.92 39.89 39.84
9 48.09 48.06 48.01
10 37.04 37.01 36.98
11 23.38 23.36 23.31
12 5.39
(t_like)
122.87 5.35
(t_like)
122.82 5.36
(t_like)
122.77
13 144.10 144.08 144.05
14 42.14 42.13 42.07
15 28.24 28.25 28.20
16 23.80 23.77 23.72
17 47.04 47.03 46.98
18 3.15
br dd
41.69 3.10
br dd
41.66 3.12
br dd
41.60
19 46.26 46.24 46.19
20 30.73 30.71 30.67
21 34.02 34.00 33.95
22 32.53 32.52 32.46
23 1.23 s 28.24 1.20 s 28.10 1.27 s 28.16
24 0.94 s 16.90 1.01 s 16.91 1.10 s 17.05
25 0.88 s 15.59 0.83 s 15.60 0.83 s 15.57
26 1.06 s 17.51 0.98 s 17.48 1.03 s 17.41
27 1.22 s 26.05 1.22 s 26.02 1.20 s 26.00
28 176.48 176.47 176.44
29 0.88 s 33.11 0.85 s 33.09 0.86 s 33.06
30 0.88 s 23.70 0.84 s 23.68 0.85 s 23.68
The 1H_NMR spectrum of compound 1 showed a sig-
nal assignable to a carboxyl group (δ12.15 (1H , br.
s)), five aromatic signals due to a mono_substituted ben-
zene moiety (δ7.48(2H , d , J =7.6Hz), 7.33(2H ,
t , J =7.6 Hz), 7.24 (1H , t , J =7.6 Hz)), along
with another eight olefinic proton signals indicative of the
presence of four conjugated double bonds , as shown in
Table 3.The 13C_NMR spectrum displayed a total of 15
sp2 hybridized carbon signals(including two overlapped).
In the lowest field , a carboxyl group that appeared at δ
167.40 could be easily discerned , which was supported
by the presence of a peak at m/ z 181 ((M-COOH)+ ,
87)in the EI_MS spectrum.
The 1H-NMR and 13C_NMR signals were attributed
by using 1H_1H COSY and HMQC spectra.In the high-
field of the 1H-NMR spectrum , doublet signal (δ5.90(1H , d , J =15.2 Hz))can be assigned to H_2 , which
was adjacent to the carboxyl group(Fig.3).In the 1H_1H
COSY spectrum , the correlations among H_2/H_3 , H_3/
H_4 , H_4/H_5 , H_5/H_6 , H_6/H_7 , H_7/H_8 and H_
8/H_9 were observed(Fig.3).These findings , together
Table 2　1H-NMR and 13C_NMR spectral data(500 MHz)of the
sugar moieties of compounds 3-5 in pyridine_d5
Position
Compound 31) Compound 41) Compound 51)
δH (J in Hz) δC δH (J in Hz) δC δH (J in Hz) δC
At C_3
1 4.73
(7.0)
107.27 4.82
(4.0)
104.56 4.75
(6.8)
105.16
2 4.37 72.85 75.94 4.43 75.66
3 4.12 74.54 73.962) 4.15 74.10
4 4.28 69.36 68.34 4.19 69.13
5 3.78 , 4.27 66.64 64.27 4.22 , 3.75
(brd 10.5)
65.40
Sugar at C_2 of inner sugar
1 5.94
(br.s)
101.64 6.12
(br.s)
101.44
2 72.43 4.90 71.51
3 72.76 4.73 83.05
4 73.66 4.40 72.76
5 69.83 4.55 69.69
6 18.47 1.49
(6.0)
18.37
Sugar at last
1 5.39(5.7)106.48
2 4.04 75.72
3 4.18 78.31
4 4.18 71.41
5 4.16 78.34
6 4.28 , 4.40 62.43
At C_28
1 6.18
(8.1)
95.60 6.10
(8.0)
95.58 6.17
(8.0)
95.53
2 4.07 73.73 73.802) 4.07 73.76
3 4.15 78.66 78.63 4.15 78.55
4 4.24 70.91 70.87 4.24 70.79
5 4.04 77.96 77.95 4.03 77.89
6 4.27 ,
4.60
69.23 69.22 4.25 ,
4.60
69.06
Sugar at C_6 of inner sugar
1 4.94
(7.8)
104.75 4.89
(7.5)
104.72 4.94
(8.0)
104.63
2 3.87 75.25 75.23 3.86 75.18
3 4.08 76.49 76.46 4.06 76.41
4 4.32 78.45 78.40 4.31 78.34
5 3.62 77.06 77.03 3.58 76.96
6 4.04 ,
4.16
61.35 61.36 4.01 ,
4.13
61.26
Sugar at last
1 5.77
(br.s)
102.69 5.69
(br.s)
102.66 5.77
(br.s)
102.59
2 4.60 72.47 72.24 4.60 72.37
3 4.47 72.69 72.50 4.45 72.60
4 4.25 73.89 73.882) 4.25 73.82
5 4.85 70.27 70.24 4.88 70.20
6 1.62
(6.2)
18.43 18.41 1.63
(6.1)
18.37
1)Signals were assigned by 1H_1H COSY , HMQC , HMBC , 1H_1H TOCSY ,
HMQC_TOCSY spectra.2)Values in any vertical columnmay be reversed al-
though those given here are prefered.
with consideration of the coupling constants of each pro-
ton , led us to conclude that compound 1 possessed a 9_
substituted 2E ,4E ,6E , 8E_nontetraenoic acid moiety.
The mono_substituted benzene moiety was further
9 期 鞠建华等:中国特有药用植物铁破锣中的新皂甙类成分(英) 985　
Table 3　1H_NMR(500MHz)and 13C_NMR(125MHz)spectral data of beesic acid(1)in DMSO_d6
Position 　　　δH (J in Hz) δC (HMQC) 1H_1H COSY
1(COOH) 12.15(1H , br.s) 167.40
2 5.90(1H , d , J =15.2Hz) 121.44 H_3
3 7.25(1H , dd , J=15.2 , 11.3 Hz) 127.86 H_2 , H_4
4 6.48(1H , dd , J=14.6 , 11.3 Hz) 130.20 H_3 , H_5
5 6.78(1H , dd , J=14.6 , 11.1 Hz) 140.36 H_4 , H_6
6 6.51(1H , dd , J=14.7 , 11.1 Hz) 132.47 H_5 , H_7
7 6.64(1H , dd , J=14.7 , 10.8 Hz) 137.10 H_6 , H_8
8 7.01(1H , dd , J=15.7 , 10.8 Hz) 128.79 H_7 , H_9
9 6.72(1H , d , J =15.7Hz) 134.39 H_8
1′ 136.68
2′, 6′ 7.48(2H , d , J =7.6 Hz) 126.47 H_3′(5′), H_4′
3′, 5′ 7.33(2H , t , J =7.6 Hz) 128.62 H_2′(6′), H_4′
4′ 7.24(1H , t , J =7.6 Hz) 143.94 H_3′(5′), H_2′(6′)
Fig.3.　1H_1H COSY of compound 1.
supported by the presence of a series of fragment ions at
m/ z 77(35), 63 (15), 51(20), and 39(15)in the
EI_MS spectrum.It was linked at C_9 of the above moiety
as the only possible site.An HMQC experiment was per-
formed and enabled complete assignment of all NMR sig-
nals(Table 3).Thus , the above evidence unambiguously
allowed us to establish the structure of compound 1 as 9_
phenyl_2E , 4E , 6E , 8E_nontetraenoic acid.Although
this compound has been reported by synthesized
method
[ 9] , as far as we could exhaust from the literature ,
compound 1 was isolated from natural sources for the first
time , named beesic acid.
Vanillic acid (2)[ 10] , oleanolic acid_3_O_α_L_ara-
binopyranosyl_28_O_α_L_rhamnopyranosyl_(1 ※ 4)_β_D_
glucopyranosyl_(1※6)_β_D_glucopyranosyl ester (3)[ 11]
and hederasaponin B(4)[ 8] were identified by IR , MS ,
1H_NMR , 13C_NMR , HMQC , HMBC , 1H_1H COSY ,
1H_1H TOCSY and HMQC_TOCSY spectral evidence.
2　Experimental
2.1　General experimental procedures
Melting points were determined on Fisher_Johns and
uncorrected.Optical rotations were measured with a
Perkin_Elmer 241 polarimeter.IR spectra were measured
with a Peking_Elmer 983G spectrometer.NMR spectra
were measured in pyridine_d5 with the Bruker AM_500
MHz spectrometers using TMS as internal standard.Au-
tospec_Ultima ETOF spectrometer was used to record ESI_
MS and FAB_MS spectra.Silica gel (400-500 mesh)
and D_101 resin were used for column chromatography.
2.2　Plant material
The rhizomes of Beesia calthaefolia(Maxim.)Ulbr.
were collected in Wen County , Gansu Province , China ,
in August 1998 and identified by Dr.CHEN Si_Bao , In-
stitute of Medicinal Plant Development , Chinese Academy
of Medical Sciences and Peking Union Medical College.
2.3　Extraction and isolation
The dried and pulverized rhizomes were extracted
with 95%EtOH and 50%EtOH each for two times.Af-
ter removal of solvent , the residue (950 g)was succes-
sively fractionated with CHCl3 and n_BuOH.The CHCl3
extract(292 g)was chromatographed on a column of sili-
ca gel(100-200 mesh)gradient eluting with petroleum
ether_EtOAc_MeOH (9∶1∶0-6∶3∶1)to give fractions 1-16.The fractions 1 -4 were combined and chro-
matographed on silica gel(400-500 mesh)eluting with
petroleum ether_EtOAc (10∶0-1∶9)and Sephadex_LH_
20(eluting with CHCl3_MeOH 1∶1)to yield compound 1(10 mg)and 2(0.75 g).The n_BuOH extract(105 g)
was chromatographed on D_101 resin and eluted succes-
sively with H2O and 95%EtOH.The fraction eluted with
95%EtOH was subjected to low pressure column chro-
matography over silica gel(400-500 mesh)by gradient
elution with CHCl3_MeOH_H2O(9∶1∶0.1-7∶3∶0.3)to
give fractions A-E.Fractions C , D and E were repeat-
edly chromatographed over silica gel under the above con-
ditions and Sephadex_LH20(eluting with MeOH_H2O 1∶
0.1), respectively , to afford compound 3 (60 mg), 4(3.5 g)and 5(4.5 g).
2.4　Identification
Beesic acid (1)　IRνKBrmax cm-1:3 600-3 300 ,
3 015 , 1 675 , 1 615 , 1 595 , 1 565 , 1 445 , 1 415 ,
1 305 , 1 270 , 1 160 , 1 140 , 1 130 , 1 010 , 985 , 955 ,
940 , 750 , 690.UV λMeOHmax nm:342 , 350 , 368.EI_MS
m/z(%):226 (M+)(100), 181 (M -45)+(87),
165(60), 154(28), 141(43), 128(35), 115(54),
103(30), 91(70), 77(35), 63 (15), 51(20), 39
(15).1H_NMR and 13C_NMR data see Table 3.
Vanillic acid (2)　Colorless needles.Mp 206-
208 ℃(Me2CO).IRνKBrmax cm-1:3 480(OH), 3 090 ,
3 000-2 500(COOH), 1 680(C O), 1 595 , 1 520 ,
1 470(Ar), 1 430 , 1 375 , 1 300 , 1 280 , 1 240 ,
986　 植　物　学　报　　Acta Botanica Sinica 43 卷
1 200 , 1 185 , 1 165 , 1 110 , 1 015 , 910 , 880 , 810 ,
805 , 760.1H_NMR (DMSO_d6)δ:3.80 (3H , s ,
OCH3), 6.84(1H , d , J =8.7 Hz , C5_H), 7.44(2H ,
m , C2 ,6_H), 9.72 (1H , br.s , C4_OH), 12.20 (1H ,
br.s , COOH).EI_MS m/ z (%):168 (M+)(100),
153(M-CH3)+(77), 151(M-OH)+(19), 123(M
-COOH)+(9), 108 (10), 97 (40), 79 (18), 51(22), 39(12).
Oleanolic acid_3_O_α_L_arabinopyranosyl_28_O_α_L_rhamnopyranosyl_(1※4)_β_D_glucopyranosyl_(1※6)_β_D_glucopyranosyl ester (3)　White powder.
Mp 214-216 ℃(MeOH).[ α] 20D -6.70°(MeOH , c
0.15).IRνKBrmax cm-1:3 600-3 100 , 1 740 , 1 635 ,
1 060 , 1 035.FAB_MS m/ z:1 081 (M +Na)+.1H-
NMR and 13C-NMR data see Table 1 and Table 2.
Hederasaponin B(4)　White powder.Mp 220-
222 ℃(MeOH).[α] 20D -19.40°(MeOH , c 0.34).IR
νKBrmax cm-1:3 600-3 100 , 1 735 , 1 635 , 1 090 , 1 060.
ESI_MS m/ z:1 081(M-146+Na)+ , 949(M-146-
132+Na)+ , 803(M-146-132-146+Na)+ , 749 ,
617 , 471 , 439.1H-NMR and 13C_NMR data see Table 1
and Table 2.
Beesioside Q (5)　White powder.Mp 226-230
℃(MeOH).[α] 20D -19.20°(MeOH , c 0.19).IRνKBrmax
cm-1:3 600-3 100 , 1 735 , 1 640 , 1 090 , 1 050.
ESI_MS m/ z:1 205(M-162+H)+ , 1 081(M-162
-146+Na)+ , 949(M-162-146-132+Na)+ , 803
(M-162-146-132-146+Na)+ , 749 , 617 , 471 ,
439.1H-NMR and 13C_NMR data see Table 1 and Table
2.
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P G.Studies on the constituents of Beesia calthaefolia and
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[ 4] 　Inoue T , Sakurai T , Nagai M , Xiao P G.Beesioside Ⅲ , a
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9 期 鞠建华等:中国特有药用植物铁破锣中的新皂甙类成分(英) 987