全 文 ：Jou rnal of Ch inese Pharm aceutica l Sc iences 2006, 15(1):15-20 15　
Flavanoids from Clematis hexapetala
DONG Ca i-x ia1, 2 , WU K e-si1 , SH I She-po2 , and TU Peng-fei2*
(1. D epartm ent of Pharm aceutical Sciences, Shaanx iUniversity of Traditional Ch ineseM edicine, X ianyang 712046 , Ch ina;
2. School of Pharm aceutica l Sciences, Pek ing Un iversity, B eijing 100083 , China)
Received date:2005-11-17.
Foundat ion item:NationalN atu ral Science Foundation of Ch ina
(2004AA2Z3730).
* Ccorrespond ing author:Tel 86-10-82802750,
E-m ail pengfeitu@b jm u. edu. cn
Abstract:A mi 　To study the chem ica l constituents from the roo ts and rhizomes of Clematis
hexapeta la Pa l.l . Methods　The componentsw ere iso lated bymeans of so lvent extrac tion, repea ted
chroma tog raphyw ith silica ge l, sephadex LH-20 and prep-HPLC. The struc turesw ere dete rm ined by
spectrum analysis. Results　Twe lve f lavono ids w ere iso lated and their structures we re iden tified as
3, 5, 6, 7 , 8, 3′, 4′-heptamethoxy flavone (1), nob ile tin (2), liquiritigenin (3), hesperetin
(4), naringenin (5), liqu iritigen-7-O-β-D-g lucopyrano side (6), 5, 7, 4′-trihyd roxy-3′-me thoxy-
flavanone -7-O-α-L-rhamnopy ranosy l(1→6)-β-D-g lucopy ranoside (7), 6-hydroxyb iochain A (8),
formononetin (9), daidze in (10), genistein (11), and tectoridin (12). Conclusion　A ll the said
compounds w ere isola ted from the p lant fo r the first time.
Key words:C lematis hexapetala Pa l.l;flavono ids;struc ture determ ina tion
CLC number:R284. 1;R284. 2　Document code:A　Article ID:1003 -1057(2006)1-015-06
In troduction
Clematis hexapeta la Pal.l is one of the three spe-
cies o f genus Clematis, which have been used as the
Chinese drug ‘W ei Ling X ian’ in Chinese Pharmaco-
poe ia (2000 edition). It is distributed w idely in the
northeast o f China and has been used as an ana lgesic,
diu re tic and anti-inf lammatory agen.t Prev ious stud ies
on its chem ical constituents invo lved the Clematis
chinensis Pal.l andC lematismanshurica Rupr. . But no
reseach onClematis hexapeta la Pal.l has been reported
so far. In o rde r to compare the chem ical constituen ts of
the th ree species of Clematis, we have stud ied the
chem ical constituents of the roots and rhizomes of
Clematis hexapetala Pa l.l . A s a resu lt, twe lve fla-
vonoids have been iso lated and identified from the 50%
E tOH ex tract o f the plan.t And a ll the compoundsw ere
iso lated from the plan t for the first time.
Expe rimenta l
General Procedures　Melting po ints w ere meas-
ured on an e lectro therma lme lting po int apparatus. O p-
tical rota tions w ere measured using a Perk in E lmer
243B digita l po larime te r.
1
H and
13
C NMR spectra
w ere reco rded on an Inova-300 opera ting at 300 MHz
and 75. 5 MH z, respective ly. E I-MS was recorded on
an Trace-MS. Prep-HPLC was performed on aW aters
liquid chroma tog raph M ode l 6 CE, equipped w ith a
W aters 2487 dua lλabso rbance de tecto r, aW ate rs 600
pump and an A lltech co lumn ofODS C18(250mm ×10
mm ID , 5μm). S ilica ge l(100 - 200mesh, 200 -
300 mesh, Q ingdao M arine Chem ical Factory) was
used for co lumn chromatography.
P lantmater ial　The roo ts and rh izomes o fClem-
atis hexapeta la Pa l.l w e re collected at Hailar in Inner
M ongo lian Autonomous Reg ion o f Ch ina in Sep tember
2004. It was iden tified by Professor Tu Peng-fe.i A
vouche r specimen w as depo sited in the he rbarium o f
M odern Research Center for Traditional ChineseM edi-
cine, Peking Un iversity Hea lth Science C enter (N o:
200409011).
16　 Journa l o f Chine se Pharm aceu tical Sciences 2006, 15(1):15-20
F igure 1　Struc tures of compounds 1 - 12
　　Extraction and Isolation　D ried roo ts and rhizo-
mes(19 kg)were extrac ted 3 times a t60℃ w ith 95%
E tOH and 50% E tOH , respective ly. The m ixed fil-
trates w ere concen tra ted in a vacuum evaporator to af-
fo rd residues A and B. Residue B w as suspended in
w a ter and ex tracted successive ly w ith E tOA c and n-
BuOH. The E tOAc ex tract (100 g) was chrom ato-
graphed on a silica ge l column and e luted w ith chloro-
fo rm-me thano l in a g radien t up of me thanol to g ive
eigh t fractions (Fr. 1 - 8). F r. 3 w as sub jec ted to
silica ge l co lumn chroma tog raphy (pe troleum e ther:
ch lo ro form 1∶1→ 0∶100 and ch loroform-me thanol
100∶1→1∶2) to g ive five fractions(Fr. 3. 1 - 3. 5).
F r. 3.2 was chromatog raphed on a silica gel co lumn and
eluted w ith cyclohexane-ch loroform-acetone (8∶2∶0. 5),
and then purified by prep-HPLC (methano l-0. 05%
trifluoroace tic acid 55∶45) to g ive compounds 1 (7. 2
mg) and 2 (5. 4mg). F r. 3. 3 w as chromatog raphed
on Sephadex LH-20 and e lu ted w ith ch lo ro form-me tha-
nol (3∶1), and then purified by prep-HPLC (me tha-
nol-0. 05% trifluoroacetic ac id 48∶52) to g ive com-
pound 9 (8. 0 mg). F r. 3. 4 w as chromatographed on
a silica gel column and e lu ted w ith cyc lohexane-chloro-
fo rm-acetone (4∶1∶1→1∶1∶1), and then subjected to
prep-HPLC (methano l-0. 05% trifluoroacetic acid
40∶60) to get compound 3 (5. 0 mg), compound 4
(9. 4mg) and compound 8 (12. 0mg). F r. 3. 5 w as
purified w ith prep-HPLC (methano l-0. 05% trifluoro-
acetic acid 40∶60) to ge t compound 10 (10. 0 mg).
F r. 4 w as subjected to si lica ge l co lumn chromatogra-
phy and e luted w ith cyc lohexane-chlorofo rm-ace tone
(4∶2∶1) repeated ly, and then purified by prep-HPLC
(methano l-0. 05% trifluo roacetic acid 42∶58) to g ive
compound 5 (4. 0 mg) and compound 11 (3. 8 mg).
F r. 6 w as sub jec ted to silica gel co lumn chrom atog ra-
phy and e luted w ith ch loro form -methano l (25∶1→
5∶1) repea tedly to g ive pa le ye llow prec ip itates and
w ashed w ith me thano l repeated ly to obta in compound
12 (61. 8 mg). F r. 7 w as chromatographed on a silca
ge l co lumn and e lu ted w ith chlo rofo rm-me thano l
(25∶1→5∶1) repeated ly to ge t compound 6 (50. 8
mg). F r. 8 w as filtrated to g ive w hite prec ipita tes and
then w ashed w ith me thano l repeated ly to obtain com-
pound 7 (800. 7 mg).
Iden tification of Structures
3, 5, 6, 7, 8, 3′, 4′-Heptamethoxyflavone
(1)　Ye llow powder, mp 125 - 127℃. EI-MSm /z
432 [M ] +. Fo r 1H and 13C NMR (in CD3OD) spec-
tral data see Tab le 1. A ll the data above are in agree-
mentw ith those o f 3, 5, 6, 7, 8 , 3′, 4′-hep tame-
thoxy flavone
[ 4]
.
Nob ile tin (2)　Co lo rless need les (in methano l).
mp 128 - 129 ℃. EI-MSm /z 402 [M ] +, 239 [A1 -
H] +, 162 [B1 ] +. 1H and 13C NMR spectral data ( in
DMSO) are g iven in Table 1. A ll the data above we re
in ag reementw ith those o f nobiletin
[ 4]
.
Liqu ir itigenin (3)　 Pale ye llow powder, mp
200 - 201℃. EI-MS m /z 256 [M ] + , 136 [ A 1 ] +,
120 [ B1 ] +. 1H and 13 C NMR ( in CD3OD) spectra l
data are presented in Tab les 2 and 3, respectively. A ll
the data above are in ag reemen tw ith those of liquiriti-
genin
[ 5]
.
Hesperetin (4)　Ye llow powde r, mp 224 -
DONG Ca i-x ia, et a l:F lavano ids from Clem atis hexapetala 17　
225℃. E I-MSm /z 302[M ] +. 1H and 13C NMR ( in
CD3OD) spectra l data are shown in Tab les 2 and 3,
respective ly.
1
H NMR spec tral da taw ere in agreement
w ith those o f hespe re tin
[ 6]
.
Naringenin (5)　Pa le ye llow powde r, mp 243 -
244℃. EI-MS m /z 272 [M ] +, 153 [ A1 +H ] + ,
120 [ B1 ] +. 1H NMR ( in DM SO) spectral data are
given in Table 2. A ll the da ta above are in agreement
w ith those of na ringenin
[ 7]
.
Liqu ir itigen-7-O-β-D-glucopyranoside (6) 　
Amorphous white pow de r, [ α] 20D - 25. 6°(c 0. 5,
DMSO), show ing a po sitive reaction in M o lish rea-
gen.t
1
H and
13
C NMR ( in DMSO) spectra l data are
g iven in Tab les 2 and 3 , respective ly. A ll the da ta a-
bove are in agree tmentw ith those o f liquiritigen-7-O-β-
D-glucopy ranoside[ 8] .
Tab le 1　300MHz NMR data of com pounds 1 and 2
No.
1
δH δC
　　 2
δH δC
2 153. 1 160. 3
3 145. 3 6. 85 (1H , s) 106. 3
4 175. 7 175. 83
5 148. 2 147. 2
6 141. 8 143. 5
7 153. 2 151. 0
8 139. 4 137. 7
9 149. 2 147. 5
10 115. 7 114. 3
1′ 124. 2 123. 1
2′ 7. 78 (1H , s) 112. 4 7. 53 (1H , d, J =2. 1) 108. 9
3′ 150. 4 149. 0
4′ 155. 5 151. 8
5′ 7. 12 (1H , d, J =8. 4) 112. 6 7. 14 (1H , d, J =8. 4) 111. 8
6′ 7. 83 (1H , d, J =8. 4) 123. 4 7. 65(1H , d, J=8. 4, 2. 1) 119. 3
OCH3 4. 09 (3H , s) 62. 3 4. 01 (3H , s) 61. 9
3. 99 (3H , s) 61. 9 3. 96 (3H , s) 61. 8
3. 91 (3H , s) 61. 8 3. 87 (3H , s) 61. 5
3. 91 (3H , s) 61. 7 3. 84 (3H , s) 61. 4
3. 91 (3H , s) 59. 9 3. 83 (3H , s) 55. 7
3. 90 (3H , s) 56. 0 3. 77 (3H , s) 55. 7
3. 81 (3H , s) 55. 9
Tab le 2　300MHz 1H NMR data of compounds 3 - 7
No. 3 4 5 6 7
2 5. 72 (1H, dd, J=12. 8, 2. 7) 5. 30 (1H, dd, J=12. 6, 3. 0) 5. 48 (1H, dd, J=12. 9, 3. 0) 5. 55 (1H, dd, J=12. 9, 2. 7) 5. 50 (1H , dd, J =12. 0, 2. 7)
3a 2. 95 (1H, dd, J=16. 8, 12. 8) 3. 14 (1H, dd, J=17. 1, 12. 6) 3. 29 (1H, dd, J=17. 4, 12. 9) 2. 87 (1H, dd, J=16. 5, 12. 9) 3. 33 (1H , dd, J =17. 4, 12. 0)
3b 2. 95 (1H, dd, J=16. 8, 2. 7) 2. 69 (1H, dd, J=17. 1, 3. 0) 2. 67 (1H, dd, J=17. 4, 3. 0) 2. 67 (1H, dd, J=16. 5, 2. 7) 2. 77 (1H , dd, J =17. 4, 2. 7)
5 7. 62 (1H, d, J=8. 7) 7. 65 (1H, d, J=8. 7)
6 6. 39 (1H, dd, J=8. 7, 1. 8) 6. 82 - 6. 94 (4H , m, 6, 2′, 5′, 6′) 5. 88 (2H, s) 6. 51 (1H, dd, J=8. 7, 2. 1) 6. 14 (1H , d, J=2. 1)
8 6. 24 (1H, d, J=1. 8) 5. 88 (1H, s ) 5. 88 (2H, s) 6. 35 (1H, d, J=2. 1) 6. 12 (1H , d, J=2. 1)
2′ 7. 22 (2H, d, J=8. 4) 6. 82 - 6. 94 (4H , m, 6, 2′, 5′, 6′) 7. 32 (2H, d, J =8. 4) 7. 45 (2H, d, J=8. 7) 6. 92 (3H ,m)
3′ 6. 72 (2H, d, J=8. 4) 6. 79 (2H, d, J =8. 4) 7. 06 (2H, d, J=8. 7)
5′ 6. 72 (2H, d, J=8. 4) 6. 82 - 6. 94 (4H , m, 6, 2′, 5′, 6′) 6. 70 (2H, d, J =8. 4) 7. 06 (2H, d, J=8. 7) 6. 92 (3H ,m)
6′ 7. 22 (2H, d, J=8. 4) 6. 82 - 6. 94 (4H , m, 6, 2′, 5′, 6′) 7. 32 (2H, d, J =8. 4) 7. 45 (2H, d, J=8. 7) 6. 92 (3H ,m)
-OCH 3 3. 85 (3H, s) 3. 77 (3H , s)
G lc
1 4. 89 (1H, d, J=6. 9) 4. 98 (1H , d, J=7. 5)
Rha
1 4. 52 (1H , s)
*O ther protons of the sugarswere not assigned ow ing to occurrence of strange overlap s
18　 Journa l o f Chine se Pharm aceu tical Sciences 2006, 15(1):15-20
　　( 5, 7, 4′-Trihydroxy-3′-methoxyflavanone-7-O-
α-L-rhamnopyranosyl)-β-D-glucopyranosideA (7)　
Amorphous white powder, mp 259 - 261 ℃, show ing a
positive reaction inM olish reagen.t
1
H and
13
C NMR (in
DM SO) spectral data are presented in Tab les 2 and 3, re-
spective ly. A ll the data above are in agreementw ith those
of (5, 7, 4′-trihydroxy-3′-me thoxyflavanone-7-O-α-L-rh-
amnopy ranosy l)-β-D-glucopy ranoside[ 9] .
Tab le 3　13C NMR data of compounds 3 - 12 (300MHz)
No. 3 4 6 7 8 9 10 11 12
2 78. 9 80. 2 78. 7 78. 4 155. 0 153. 0 152. 4 154. 1 152. 9
3 43. 2 44. 0 43. 2 42. 1 123. 3 123. 1 123. 3 121. 2 121. 1
4 190. 1 197. 4 189. 9 197. 1 182. 6 174. 6 174. 6 180. 2 180. 8
5 129. 3 169. 0 132. 4 162. 5 158. 8 127. 3 127. 0 162. 0 157. 5
6 110. 6 103. 2 110. 6 96. 4 132. 8 115. 3 115. 5 99. 0 132. 4
7 164. 9 165. 4 164. 7 163. 0 158. 9 162. 8 164. 7 164. 3 156. 6
8 102. 6 96. 4 113. 5 95. 6 95. 0 102. 1 101. 9 93. 7 94. 2
9 163. 2 149. 3 163. 1 165. 1 154. 6 157. 5 157. 7 157. 4 152. 5
10 113. 4 103. 2 102. 6 103. 3 106. 3 116. 5 116. 0 104. 5 106. 5
1′ 130. 1 119. 0 128. 4 130. 9 124. 2 124. 3 122. 7 122. 3 122. 1
2′ 128. 4 112. 5 128. 0 118. 0 131. 4 130. 1 130. 0 130. 2 130. 2
3′ 115. 1 133. 2 116. 2 146. 4 116. 2 113. 6 114. 9 115. 1 115. 1
4′ 157. 6 147. 8 157. 4 148. 0 155. 0 158. 9 157. 1 157. 6 154. 8
5′ 115. 1 114. 5 116. 2 112. 0 116. 2 113. 6 114. 9 115. 1 115. 1
6′ 128. 4 131. 4 128. 0 114. 1 131. 4 130. 1 130. 0 130. 2 130. 2
-OCH3 56. 4 55. 7 60. 9 55. 1 60. 3
G lc
1 100. 3 99. 4 100. 1
2 73. 2 73. 0 73. 1
3 77. 1 76. 3 77. 3
4 69. 7 69. 6 69. 6
5 76. 6 75. 5 76. 7
6 60. 7 66. 0 60. 6
Rha
1 100. 6
2 70. 7
3 70. 3
4 72. 1
5 72. 1
6 17. 8
Tab le 4　300MHz 1H NMR data of compouds 8 - 12
No. 8 9 10 11 12
2 8. 01 (1H , s) 8. 34(1H , s) 8. 23 (1H , s) 8. 32(1H , s) 8. 45 (1H , s)
5 7. 97(1H , d, J=8. 7) 7. 91 (1H , d, J =8. 7)
6 6. 94(1H , dd, J =8. 7, 2. 1) 6. 87(1H , dd, J=8. 7, 1. 8) 6. 39(1H , d, J=1. 8)
8 6. 40 (1H , s) 6. 87(1H , d, J=2. 1) 6. 76 (1H , d, J =1. 8) 6. 23(1H , d, J=1. 8) 6. 89 (1H , s)
2′ 7. 34 (2H , d, J =8. 4) 7. 51(2H , d, J=8. 7) 7. 32 (2H , d, J =8. 4) 7. 37(2H , d, J=8. 4) 7. 50 (2H , d, J =9. 0)
3′ 6. 85 (2H , d, J =8. 4) 6. 99(2H , d, J=8. 7) 6. 80 (2H , d, J =8. 4) 6. 82(2H , d, J=8. 4) 6. 83 (2H , d, J =9. 0)
5′ 6. 85 (2H , d, J =8. 4) 6. 99(2H , d, J=8. 7) 6. 80 (2H , d, J =8. 4) 6. 82(2H , d, J=8. 4) 6. 83 (2H , d, J =9. 0)
6′ 7. 34 (2H , d, J =8. 4) 7. 51(2H , d, J=8. 7) 7. 32 (2H , d, J =8. 4) 7. 37(2H , d, J=8. 4) 7. 50 (2H , d, J =9. 0)
OCH3 3. 85 (3H , s) 3. 79(3H , s) 3. 78 (3H , s)
5-OH 12. 96 (1H , s) 12. 94 (1H , s)
7-OH 9. 62(1H , s) 9. 62 (1H , s)
G lc
1 5. 10 (1H , d, J =7. 5)
*O ther protons of the sugar w ere not assigned for curious overlapped
DONG Ca i-x ia, et a l:F lavano ids from Clem atis hexapetala 19　
　　6-Hydroxybiochain A (8) 　Co lorless needles (in
methanol), EI-MS m /z 300 [M ] + , show ing a positive
reaction in G ibbs reagen.t
1
H and
13
C NMR (in CD3OD)
spectral data are given in Tab les 4 and 3, respectively.
A ll the data above are in ag reetment w ith those of 6-
hydroxybiochain A
[ 10]
.
Formononetin (9)　Co lo rless need les ( in metha-
no l), mp 257 - 258 ℃. E I-MS m /z 268 [M ] +, 136
[A1 ] +, 132 [ B1 ] +. 1H and 13 C NMR ( in DM SO )
spectral data are presented in Tables 4 and 3, respective-
ly. A ll the da ta above are in agreementw ith those o f for-
mononetin
[ 11]
.
Daidze in (10)　Ye llow powder, E I-MS m /z 254
[M ] +, 137 [A1 +H] +, 118 [B1 ] +. 1H and 13 C NMR
(in CD3OD ) spectral data are shown in Tables 4 and 3,
respective ly. A ll the data above are in agreement w ith
those of daidzein
[ 12]
.
Genistein (11)　White needles(in me thano l), mp
287 -289 ℃. EI-MSm /z 270 [M ] +, 153 [A1 +H ] +,
152 [A1 ] +, 118 [B1 ] +. 1H and 13C NMR (in DMSO)
spectral data are given in Tab les 4 and 3, respectively.
A ll the data above ware in agreement w ith those of
genistein
[ 11]
.
Tector id in (12)　Amorphous white powder. mp
274 -275℃, show ing a positive reac tion in bo thM o l-
ish reagent and G ibbs reagen.t
1
H and
13
C NMR ( in
DM SO) spec tral data are p resented in Tables 4 and 3,
respective ly. A ll the data above are in agreement w ith
those o f tec to ridin
[ 13]
.
Resu lts and D iscussion
Compound 1 show ed a negative reac tion on spra-
y ing of fe rric chlo ride-potassium ferricy anide so lution,
suggesting that 1 has no pheno l-hydroxy l g roup. Its 13
CNMR spectrum showed 15 arom atic carbon signals,
one of wh ich a tδ175. 7, suggesting that 1 is a fla-
vone. Fu rthermo re, its 1H and 13 C NMR spectra
show ed the signa ls attributed to sevenmethoxy g roups:
δH 4.09 (3H , s), 3.99 (3H , s), 3.91 (9H , s),
3.90 (3H , s), 3.81 (3H , s) and δC 62.3, 61.9,
61.8, 61.7, 59.9, 56.0, 55.9 . A ll the above-men-
tioned data indicate that 1 is a flavone substituted w ith
seven methoxy ls. M oreove r, the 1H NMR spectrum
show ed the resonance s of an ABX system protons at:
δ7. 83 (1H , d, J =8. 4H z, 6′-H), 7. 12 (1H , d,
J =8. 4 H z, 5′-H), and 7. 18 (1H , s, 2′-H ),
wh ich are assigned to B-ring. The NMR data of 1 are
in ag reetment w ith 3, 5, 6, 7, 8, 3′, 4′-hep tame-
thoxy flavone
[ 4] , so 1 was de term ined as 3, 5, 6, 7,
8, 3′, 4′-heptamethoxy flavone.
C ompound 6 show ed a positive reaction w ith spra-
y ing o f ferric chloride-po tassium ferricyan ide solution
and a positive reaction in M o lish reagen t, indicating
tha t 6may be a pheno lic g lycoside. Its
13
C NMR spec-
trum exh ib ited the resonances o f 15 carbons and the
signals due to a g lucopy ranosyl un it of wh ich the ano-
meric ca rbon w as observed at 100. 3 co rresponding to
the anome ric proton at 4. 89 (1H , d, J =6. 9 Hz);
the large coup ling constant suggested that the g lucose
exists in β position. M o reove r, its 13C NMR spectrum
show ed a carbony l carbon a t δ189.9 (C-4), one
methy l carbon atδ78. 7 (C-2), and one me thy lene
carbon atδ43. 2 (C-3), suggesting tha t 6 is a flava-
none g lucoside. Its
1
H NMR spectrum showed anABX
type a roma tic p ro tons atδ7. 65 (1H , d , J =8. 7H z,
5-H), δ6. 51 (1H , dd, J =8. 7, 2. 1 H z, 6-H),
δ6. 35 (1H , d , J =2. 1 Hz, 8-H ) and A2 B2 type
aroma tic p ro tons atδ7. 45 (2H , d, J =8. 4H z, 2′,
6′-H) and δ7. 06 (2H , d, J =8. 4H z, 3′, 5′-H).
The NMR da ta of 6 are in agree tmen t w ith those o f
liquiritigen-7-O-β-D-g lucopy ranoside[ 8] , so 6 was de-
term ined as liquiritigen-7-O-β-D-g lucopyranoside.
C ompound 12 show ed a positive reaction w ith
spray ing o f ferric ch loride-po tassium fe rricyanide so lu-
tion and a positive reaction inM o lish reagen t, indica-
ting that 12 is a pheno lic g lycoside. Its
13
C NMR spec-
trum exh ib ited the resonances o f 15 carbons and the
signals due to a g lucopyrano se unit of w hich the ano-
meric ca rbon w as obse rved a tδ100. 1 and the corre-
sponding anomeric proton w as presen ted at δ5. 10
(1H , d, J = 7. 5 H z); the large coupling constan t
sugge sted tha t the g lucose ex ists in β position. Its 1H
NMR spectrum show ed one arom atic pro ton atδ8. 45
(1H , s, 2-H) and 13C NMR spec trum show ed a car-
bony l carbon atδ180. 8 (C-4 ), suggesting tha t 12 is
a isoflavone g luco side. M o reove r, its 1H NMR spec-
trum show ed an A2B2 type a roma tic protons a tδ7. 50
(2H , d, J =9. 0 Hz, 2′, 6′-H) and δ6. 83 (2H ,
20　 Journa l o f Chine se Pharm aceu tical Sciences 2006, 15(1):15-20
d, J =9. 0 Hz, 3′, 5′-H) and one arom atic pro ton
sing le t a tδ6. 89 (1H , s, 8-H). A nd 12 show ed a
positive reaction in G ibbs reagent, sugge sting the pro-
ton a tδ6. 89 (1H , s)must be H-8. TheNMR data of
12 are in ag reetmentw ith tho se o f tectoridin
[ 13] , so 12
was determ ined as tectoridin.
A cknow ledgem ents
This pro jectw as supported byNa tionalNaturalSci-
ence Founda tion of China (2004AA2Z3730). Thanks to
Q iao Liang and TaoHa i-yan (theAnaly ticC enter of Pe-
k ing Unive rsity) for providing the NMR and E I-MS
spec tra.
Re ferences
[ 1] Song ZH , Zhao YY, Duan JL. Rev iew of chem ica l con-
stituents and pha rm aco log ica l ac tions o f Clem atis species
[ J] . Nat P rod ResD ev, 1995, 7 (2):66-72.
[ 2] H uangWW. Advance s in studies on chem ica l constituen ts
and pharm aco log ical effect o fClema tis L [ J] . Chin Tradit
Herb D rugs, 2002, 33 (3):285-288.
[ 3] Chirva YY, Kony ikhov VP, Cheban PL, et a l. Kh im B io-
khim Ug levodovMa ter VsesKonf [ M ] , In:Kochetkov NK
edMoscow:N auka 1967, 14:98-100.
[ 4] Chen J, Mon tanari AM , W idme rWW. Tw o new po lym e-
thoxy la ted flavones, a c la ss o f com pounds w ith po tential
anticance r ac tiv ity, iso la ted from co ld pressed dancy Tan-
gerine pee l o il so lids [ J] . J AgricFood Chem , 1997, 45:
364-368.
[ 5] YangGZ, Zhao S, Li YC. Studies on the chem ica l constit-
uents o f Lycian thes biflora. [ J] . Acta Pharm S in , 2002,
37(6):437-439.
[ 6] L in LD, Qin GW , Xu RS. Studies on chem ica l constitu-
en ts of I lex centrochinensis [ J] . Acta Bot Sin, 1994, 36
(5):393-397.
[ 7] Zhang T, Zhang CF, W ang ZT, et a l. Studies on chem ica l
constituents o fD endrobium trigonopusRchbf [ J] . Chin J
NatM ed, 2005, 3 (1):28-30.
[ 8] L i J, Sh ige to sh i K, Yukio K, et a l. Constituents o f the
roo ts o fCynanchum bungeiDecne:iso la tion and structu res
of fou r new g lucosides, bunge iside-A, -B, -C, and -D
[ J] . Chem Pharm Bull, 1992, 40(12):3133-3137.
[ 9] Chen YF, L iu J, Dav idson ST, et al. Iso lation and struc-
ture o f C lem a tine. a new flavanone g lyco side from Clem a-
tis armanii F ranch [ J] . Tetrahedron, 1993, 49 (23):
5169-5176.
[ 10] DeanWR, Daniel RD, Mona IC, et al. Inhibition of ex-
trahepatic human cy tochromes P450 A and B by m etabo-
lism o f isoflavone s found in Trifolium pra tense [ J] . J Ag-
ricFood Chem , 2004, 52:6623-6632.
[ 11] Huang SY, Tu PF. Iso lation and identifica tion of iso fla-
vones from Triflium pratense [ J] . Acta Sci Na t Univ Pe-
k in, 2004, 40 (4):544-549.
[ 12] Ak ira K , Kazush i K, M iano ru I, et al. F irst finding of
da idze in 7-O-pho sphate and geniste in 7-O-phospha te tha t
are hydro ly zed by su lfa ta se [ J] . Tetrahedron , 2001, 57:
8801-8805.
[ 13] L i L, Q inM J. Chem ica l constituents o f Irits cathayensis
M igo [ J] . J Chin Pharm Univ, 2005, 36 (2):111-113.
棉团铁线莲黄酮类成分研究
董彩霞1, 2 , 武可泗 1 , 史社坡2 , 屠鹏飞 2
(1. 陕西中医学院 药学系 , 陕西 咸阳 712046;2. 北京大学 药学院 , 北京 100083)
摘要:目的　研究棉团铁线莲 Clematis hexapeta la Pa l.l的干燥根及根茎的化学成分。方法　利用溶剂提取 , 硅胶柱色谱
和高效液相色谱等手段进行分离 、纯化 , 根据理化性质和波谱数据进行结构鉴定。结果　分离鉴定了 12个黄酮类化合物 ,分
别为:3, 5, 6, 7, 8, 3′, 4′-七甲氧基黄酮(1), nob iletin(2), liqu iritigen in(3), 橙皮素 (4),柚皮素(5), 7, 4′-二羟基-二氢
黄酮-7-O-β-D -葡萄糖苷(6), 5, 7, 4′-三羟基-3′-甲氧基黄酮醇-7-O-α-L-鼠李糖(1→ 6)-β-D-葡萄糖苷(7), 6-hydroxyb io chain
A(8), 芒柄花素(9),大豆素(10),染料木素(11),鸢尾苷(12)。结论　以上化合物均为首次从该植物中分离得到。
关键词:　棉团铁线莲;黄酮;结构鉴定