全 文 ：mono terpen e glucosid es , s chizonepetoside A and B [ J ] .
Ch em Pharm Bu ll, 1981, 29( 6): 1636-1643.
[6 ]　 Munehi to M , Michihide K, Yuji S, et al . Phenylp ropenoic
acid deriv atives as antiinf lammato ry agent and i t s is olation
f rom Schizonepeta tenui fol ia [P ]. Japan Kokai Tokkyo Koko
JP 02, 306, 970 [90, 306, 9701 ( CI. C 07D307 /86) 20 Dec.
1990, Appl. 89 /127, 488, 19 M zy 1989, spp ].
Chemical Constituents of Pueraria peduncularis
ZHANG Xiao-rong , W ANG Ming-kui, PENG Shu-lin, L IU Fa-qiang , DING Li-sheng
( Chengdu Institute o f Biolog y , Chinese Academy o f Sciences, Chengdu Sichuan 610041, China )
Abstract: Object　 To investiga te the chemical consti tuents f rom the stem of Pueraria peduncularis
( Grah. ex Benth. ) Benth. Methods　 The consti tuents w ere iso la ted on si lica gel co lumn chromatog raphy.
Their st ructures w ere elucidated by chemical and spect roscopic evidence. Results　 Ten compounds w ere
comfi rmed as 3-O-[β -D-glucopy ranosyl-( 1→ 3) -β -D-6-O-methyl-g lucuronopy rano syl ]-3β , 15α, 23-trihy-
droxy-olean-12-en-16-one (Ⅰ ) , daidzein (Ⅱ ) , g enistein (Ⅲ ) , daidzin (Ⅳ ) , genistin (Ⅴ ) , 3β , 15α-dihy-
droxy-olean-12-en-16-one (Ⅵ ) , lupeo l (Ⅶ ) , betulinic acid (Ⅷ ) , α-spinastero l-glucopy ranoside (Ⅸ ) a nd
α-spinasterol (Ⅹ ) . Conclusion　 CompoundⅠ exhibi ted antimicrobial activ ity against Aspergil lus niger .
CompoundsⅡ～ Ⅹ were fi rst iso lated f rom this plant.
Key words: Pueraria peduncularis ( Grah. ex Benth. ) Benth; ch emical consti tuent; Aspergil lus niger
葛根的化学成分研究
张晓 ,王明奎 ,彭树林 ,刘发强 ,丁立生
(中国科学院成都生物研究所 ,四川 成都　 610041)
摘　要: 目的　从豆科葛属植物云南葛藤 Pueraria peduncularis中分离得到 10个化合物。方法　通过波谱和化学
方法分别进行鉴定。 结果　它们的化学结构为: 3-O-[β -D-吡喃葡萄糖 ( 1→ 3) -β -D-吡喃葡萄糖醛酸甲酯苷 ]-3β ,
15α, 23-三羟基齐墩果 -12-烯 -16-酮 (Ⅰ ) ,大豆素 (Ⅱ ) ,染料木素 (Ⅲ ) ,大豆苷 (Ⅳ ) ,染料木苷 (Ⅴ ) , 3β , 15α-二羟基齐
墩果 -12-烯 -16-酮 (Ⅵ ) ,羽扇醇 (Ⅶ ) ,桦木酸 (Ⅷ ) ,α-菠甾醇葡萄糖苷 (Ⅸ )和α-菠甾醇 (Ⅹ )。 结论　化合物Ⅰ 对黑曲
霉具有抑制活性。
关键词: 云南葛藤 ;化学成分 ;黑曲霉
中图分类号: R284. 1　　　文献标识码: A　　　文章编号: 0253 2670( 2002) 01 0011 04
　　We have repor ted[1 ] tw o new tri terpenoids and
one known compound obtained from the stem of
Pueraria peduncularis ( Grah. ex Benth. ) Benth.
( Legumino sae) af ter acid hydroly sis. In the pre-
sent study, ten compounds f rom the methano lic
ex t ract o f the stem of this plant have been investi-
ga ted, and compound Ⅰ show ed antimicrobial ac-
tivi ty ag ainst Aspergillus niger .
1　 Results and discussion
The HRFABMS o fⅠ gave a [M - H]- ion at
m /z 823. 452 9, in ag reement wi th the molecular
fo rmula C43 H68 O15 ( calcd fo r C43 H67 O15 m /z
823. 448 0) . The IR spect rum show ed the absorp-
tion bands of hydroxyl and ca rbonyl g roups at
3 419, 1 744 and 1 701 cm
- 1 . In the
1
HNMR and
13
CNMR spectra ofⅠ , the presence of sev en qua-
ter nary carbon atoms and the chemical shi f ts o f C-
12 a tδ125. 8 and C-13 atδ142. 0 w ere cha racteris-
tic of a△ 12 -o leanene skeleton. Acid hydrolysis of
Ⅰ gave aglyconeⅠ a, whose 1 HNM R and 13 CNMR
signals w ere identical w ith those o f 3β , 15α, 23-tri-
hydro xy-olean-12-en-16-one
[1 ]
. Glucose and met-
hyl g lucuronate w ere identi fied by TLC. The
EIM S of acetylatedⅠ show ed fragment ion at m /z
·11·中草药　 Chinese T raditional and Herbal Drug s　 2002年第 33卷第 1期
收稿日期: 2000-10-12
331 [ terminal glc ( O Ac) 4 ]
+ , suggested tha t glu-
cose w as terminal sugar. β -Configuraton at the
anomeric posi tio ns was inferred f rom the coupling
constants for bo th g lucopy ranose ( J= 7. 5 Hz) and
methyl glucuronate ( J= 7. 5 Hz) . In the
13
CNMR
spect rum of Ⅰ , the signal of C-3 w as shi fted
downfield to δ82. 2 as compared wi th analog ous
signal ofⅠ a , indicated that C-3 ofⅠ was linked
w ith the sugar chain. This conclusion w as further
suppo rted by the HMBC spect rum o fⅠ , in w hich
the proton at H-1 (δ5. 17) o f methyl g lucurona te
had cross-peak wi th C-3 (δ82. 2) ofⅠ ( Fig. 1) .
By analy sis o f HMQC and HMBC spect ra o f Ⅰ ,
the
1
HNMR and
13
CNMR signals could be assigned
( see Table. 1) . The HMBC co rrelation was ob-
serv ed betw een anomeric pro ton (δ5. 26) o f glu-
cose and C-3 (δ 87. 3 ) of methyl g lucurona te
( Fig. 1) . Therefo re , the sugar chain w as 6-O-Me-
g lu ( 3→ 1) glc. Except fo r C-6 o f methyl glu-
curona te, the carbon signals due to these sugar
moieties w ere in accord wi th the published data fo r
simi larly linked suga r moieties [-glu ( 3→ 1 )
g lc ]
[ 2]
.
The above ev idence led to the elucidation of the
st ructure of 3-O-[β -D-g lucopy ranosyl ( 1→ 3)-β -D-
6-O-methyl-glucuronopy ranosyl ]-3β , 15α, 23-tri-
hydroxy-olean-12-en-16-one. Acco rding to the pr-
actice encountered among the plant g lycosides, co-
mpoundⅠ may be an ar tifact during the ex traction
resul ting from 3-O-[β -D-glucopy ranosyl ( 1→ 3)-β -
D-g lucuronopyrano sy l ]-3β , 15α, 23-trihydro xy-ol-
ean-12-en-16-one which w as isolated from the
same plant befo re
[ 3] .
In the light of direct comparison betw een pub-
lished spectral data and that of the tested samples,
the compoundsⅡ ～ Ⅹ were identified as daidzein
(Ⅱ ) [4 ] , genistein (Ⅲ ) [ 5 ] , daidzin (Ⅳ ) [6, 7 ] , geni-
stin (Ⅴ ) [ 7] , 3β , 15α-dihydroxy-o lean-12-en-16-one
(Ⅵ ) [1 ] , lupeol (Ⅶ ) [ 8] , betulinic acid (Ⅷ ) [9 ] , α-
spinastero l-g lucopy ranoside (Ⅸ ) [10 ] and α-spinas-
tero l (Ⅹ ) [10 ] respectiv ely. 13CNMR spect ral data of
compounds Ⅱ ,Ⅲ ,Ⅳ and Ⅴ , see Table 2. The
nine compounds w ere fi rst i sola ted f rom this plant.
Table 1　 1HNMR and 13CNMR spectral data of
compoundsⅠ ( in C5D5N , 125 MHz)
andⅠ a ( in CDCl3 , 75 MHz) ( J: Hz)
C, H atom Ⅰ * Ⅰ a Ⅰ HMBC ( H to C)
　　1 　38. 6( t) 　　 38. 3
2 26. 2 ( t) 26. 7
3 82. 2 ( d) 76. 8 3. 68, t, J= 8 C: 4, 24, g lu-1
4 43. 5 ( s) 41. 8
5 47. 2 ( d) 49. 6
6 18. 0 ( t) 18. 6
7 35. 6 ( t) 35. 0
8 41. 8 ( s) 41. 8
9 47. 2 ( d) 46. 7
10 36. 8 ( s) 36. 9
11 24. 1 ( t) 23. 7
12 125. 8 ( d) 125. 5 5. 45, br . s C: 11, 14, 18
13 142. 0 ( s) 141. 5
14 46. 4 ( s) 46. 0
15 72. 8 ( d) 72. 4 4. 77, s C: 16, 17, 27
16 217. 3 ( s) 271. 3
17 54. 2 ( s) 54. 1
18 53. 0 ( d) 52. 9 2. 55, dd, J= 14. 4 C13, 17, 19
19 47. 9 ( t) 47. 7
20 30. 9 ( s) 30. 5
21 35. 9 ( t) 35. 3
22 30. 9 ( t) 30. 5
23 63. 8 ( t) 72. 1 4. 30, 3. 71, d, J= 10 C: 3, 4, 5, 24
24 13. 6 ( q) 11. 4 　　　 0. 943 C: 3, 4, 23
25 16. 4 ( q) 15. 8 　　　 0. 943
26 17. 8 ( q) 17. 6 　　　 1. 18
27 21. 9 ( q) 21. 2 　　　 0. 982 C: 13, 14, 15
28 28. 1 ( q) 28. 1 　　　 1. 24 C: 17, 18
29 33. 1 ( q) 32. 9 　　　 0. 794
30 23. 3 ( q) 23. 3 　　　 0. 844
　　* : Suga r moi ety of Ⅰ : 6-OMe-glu: 106. 1 ( d) , 74. 2 ( d) , 87. 3 ( d) ,
71. 6 ( d) , 76. 7 ( d) , 170. 3 ( s) , 52. 2 ( q) ; g lc: 105. 9 ( d) , 75. 7 ( d) , 78. 3
( d) , 71. 5 ( d) , 78. 8 ( d) , 62. 5 ( t) .
2　 Experimental
2. 1　 General experimental procedures: Optical ro-
ta tion w as detected w ith a PE-241 polarimeter. IR
spect rum was detected on a Nicolet MX-1 spec-
trometer as a pressed KBr disk. NM R spect ra w ere
reco rded on Bruker AP-300 and DRX-500 MHz
spect rums wi th TM S as the internal standard. M S
spect ra w ere detected on a V G AutoSpec-3000
·12· 中草药　 Chinese T raditional and Herbal Drug s　 2002年第 33卷第 1期
mass spect rometer. 200～ 300 mesh si lica g el and
Lich roprep RP-8 w ere used fo r column chromatog-
raph y.
2. 2　 Plant material: The whole plant o f P. pe-
duncularis was collected in Liangshan, Sichuan
Province, China and identi fied by professo r Yang
Guanghui , from Sichuan Ag ricul tural Co lleg e.
2. 3　 Ex traction and isola tion: The dried stems
( 0. 5 kg ) w ere ex t racted with MeOH fo r seven
days at room temperature. This operation w as re-
pea ted three times. Af ter removal of the solv ent ,
the residue w as suspended in H2O and successiv ely
ex t racted w ith pet roleum ether ( bp 60℃～ 90℃ ) ,
EtO Ac and n-BuOH respectiv ely. The EtO Ac ex-
tracts ( 15 g ) were repeatedly chroma tog raphed on
si lica g el and eluted wi th pet ro leum ether-acetone
( 25∶ 1) to obtain compoundsⅡ ( 43 mg ) , Ⅲ ( 40
mg) , Ⅳ ( 16 mg ) , Ⅴ ( 131 mg ) , Ⅸ ( 12 mg ) and
Ⅹ ( 55 mg ) . The n-BuOH ex tracts ( 22 g ) were
chroma tog raphed on silica gel co lumn and eluted
w ith CHCl3-M eOH ( 35∶ 1) to obtain compoundⅧ
( 19 mg ) and three f ractions. Fraction 1 was chro-
ma tog raphed on silica g el co lumn and eluted wi th
CHCl3-MeOH ( 15∶ 1) to af fo rd compoundsⅥ ( 65
mg) and Ⅶ ( 13 mg ) . Fraction 2 w as repeatedly
chroma tog raphed on si lica gel and RP-8 column
and eluted wi th CHCl3-M eOH ( 10∶ 1) and M eOH-
H2O ( 80∶ 20, 500 mL; 90∶ 10, 500 mL) sepa-
ra tely to obtain compoundⅠ ( 53 mg ) .
2. 4　 Identification: Compound Ⅰ : W hi te pow-
der. mp: 207℃～ 209℃ . [α]20D : - 9. 5°( c 0. 084,
MeOH) . IRνKBrmax ( cm- 1 ): 3 420, 2 950, 1 744,
1 702, 1 458, 1 386, 1 079, 1 033. HR-FABMS
[ M - H ]
-
m /z: 823. 452 9 ( C43 H67 O15 , calcd.
823. 448 0) . FABM S ( - ) m /z: 823 [M - H ]
- ,
471 [M- { 6-O-M e-g lu-( 3→ 1) -g lc} ]- .
Hydro lysis ofⅠ : CompoundⅠ ( 18 mg ) wa s
hydroly zed w ith 4N HCl ( 5 mL) and benzene ( 5
m L) under ref lux for 6 h. The o rg anic phase was
separated and the w ater phase w as ex t racted wi th
benzene three times. Af ter removal of benzene un-
der reduced pressure the residue w as purified by
CC on si lica g el and eluted wi th pet roleum ether-
acetone ( 3∶ 1) to obtainⅠ a ( 4 mg ) . 1 HNMRδ
( 300 MHz, CDCl3 ) of Ⅰ a: 5. 51 ( 1H, br. s, H-
12) , 4. 57 ( 1H, s, H-15) , 3. 74 ( 1H, d, J= 10
Hz, H-23) , 3. 66 ( 1H, t, J= 8 Hz, H-3) , 3. 44
( 1H, d, J= 10 Hz, H-23) , 2. 54 ( 1H, dd, J= 14,
4 Hz, H-18 ) , 1. 25, 1. 22, 1. 19, 1. 03, 0. 95,
0. 87, 0. 85 ( each 3 H, s, 7× CH3 ) .
Acetylation o fⅠ : CompoundⅠ ( 5 mg ) w as
acetylated wi th Ac2O-pyridine ( 1∶ 1, 2 m L) at
room tempera tur fo r 60 h to yield acetate of Ⅰ .
EIM S ( m /z): 331, 290, 248.
Table 2　 13CNMR spectral data of compoundsⅡ ,
Ⅲ , Ⅳ andⅤ ( in DMSO-d6 , 75 MHz)
C Ⅱ Ⅲ Ⅳ Ⅴ
2 152. 7 　　 153. 8 　　 153. 2 　　 153. 2
3 122. 4 122. 2 123. 6 122. 5
4 174. 6 180. 1 174. 6 180. 4
5 127. 2 161. 9 126. 8 161. 6
6 115. 0 98. 8 115. 5 99. 8
7 162. 4 164. 1 161. 3 163. 0
8 102. 2 93. 5 99. 9 94. 5
9 157. 3 157. 3 157. 1 157. 3
10 116. 5 104. 4 118. 4 106. 0
1′ 123. 4 121. 1 122. 2 120. 9
2′ 130. 0 130. 0 130. 0 130. 1
3′ 114. 8 114. 9 114. 8 114. 9
4′ 157. 0 157. 5 156. 9 157. 0
5′ 114. 8 114. 9 114. 8 114. 9
6′ 130. 0 130. 0 130. 0 130. 1
g lc-1 103. 0 99. 8
g lc-2 73. 0 73. 0
g lc-3 76. 3 76. 3
g lc-4 69. 5 69. 5
g lc-5 77. 1 77. 1
g lc-6 60. 5 60. 5
　　 CompoundⅡ : Whi te powder. 1 HNMRδ( 300
M Hz, DM SO-d6 ): 10. 82 ( 1H, s, 7-OH) , 9. 57
( 1H, s, 4′-OH) , 8. 30 ( 1H, s, H-2) , 7. 96 ( 1H,
d, J= 9 Hz, H-5) , 7. 38 ( 2H, d, J= 9 Hz, H-2′,
6′) , 6. 95 ( 1H, d, J= 2 Hz, H-8) , 6. 87 ( 1H, dd,
J= 9, 2 Hz, H-6) , 6. 81 ( 2H, d, J= 9 Hz, H-3′,
5′) .
CompoundⅢ : Whi te powder. 1 HNMRδ( 300
M Hz, DM SO-d6 ): 12. 97 ( 1H, s, 5-OH) , 10. 89
( 1H, s, 7-OH) , 9. 63 ( 1H, s, 4′-OH) , 8. 32 ( 1H,
s, H-2) , 7. 37 ( 2H, d, J= 9 Hz, H-2′, 6′) , 6. 82
( 2H, d, J= 9 Hz, H-3′, 5′) , 6. 38 ( 1H, d, J= 2
Hz, H-8) , 6. 22 ( 1H, d, J= 2 Hz, H-6) .
CompoundⅣ: Whi te powder. 1 HNMRδ( 300
M Hz, DM SO-d6 ): 9. 55 ( 1H, s, 4′-OH) , 8. 38
( 1H, s, H-2) , 8. 05 ( 1H, d, J= 9 Hz, H-5) , 7. 40
·13·中草药　 Chinese T raditional and Herbal Drug s　 2002年第 33卷第 1期
( 2H, d, J= 9 Hz, H-2′, 6′) , 7. 23 ( 1H, d, J= 2
Hz, H-8) , 7. 14 ( 1H, dd, J= 9, 2 Hz, H-6) , 6. 82
( 2H, d, J= 9 Hz, H-3′, 5′) , 5. 09 ( 1H, d, J= 7
Hz, H-1glc ) . ( See Table 3)
　　 CompoundⅤ : White pow der. 1HNM Rδ( 300
MHz, DM SO-d6 ) : 1 2. 94 ( 1H , s , 5-OH ) , 9. 6 1
Table 3　 13CNMR spectral data of compounds Ⅵ ,
Ⅶ , Ⅷ , Ⅸ andⅩ ( in CDCl3 , 75 MHz)
C Ⅵ 　 Ⅶ 　 Ⅷ 　 Ⅸ * 　 Ⅹ 　
　　 1 　 39. 0 　 38. 7 　 38. 8 　 37. 3 　 37. 2
2 27. 2 27. 4 27. 2 30. 0 31. 4
3 78. 9 79. 0 79. 1 77. 0 71. 1
4 38. 7 38. 9 38. 9 34. 7 37. 9
5 54. 9 55. 3 55. 4 40. 1 40. 3
6 18. 4 18. 3 18. 3 30. 0 29. 8
7 35. 3 34. 3 34. 4 117. 9 117. 5
8 41. 3 40. 9 40. 7 139. 5 139. 6
9 46. 7 50. 5 50. 6 49. 6 49. 5
10 36. 6 37. 2 37. 2 34. 5 34. 0
11 23. 7 20. 9 20. 9 21. 7 21. 6
12 125. 6 25. 2 25. 6 39. 6 39. 5
13 141. 5 38. 1 38. 3 43. 5 43. 3
14 46. 0 42. 8 42. 5 55. 3 55. 1
15 72. 7 27. 5 30. 6 23. 3 23. 0
16 217. 4 35. 6 32. 3 28. 9 28. 5
17 54. 0 43. 0 56. 3 56. 0 55. 9
18 52. 9 48. 3 47. 0 12. 6 12. 1
19 47. 7 48. 0 49. 3 13. 1 13. 1
20 30. 8 151. 0 150. 7 41. 1 40. 8
21 35. 2 29. 9 29. 7 21. 3 21. 1
22 30. 5 40. 0 37. 2 138. 7 138. 2
23 28. 0 28. 0 28. 0 129. 6 129. 5
24 15. 6 15. 4 15. 4 51. 4 51. 3
25 16. 6 16. 1 16. 0 32. 2 31. 9
26 17. 6 16. 0 16. 1 21. 6 21. 4
27 21. 3 14. 6 14. 7 19. 2 19. 0
28 28. 0 18. 0 179. 4 25. 7 25. 4
29 32. 9 109. 3 109. 6 12. 2 12. 3
30 23. 3 19. 3 19. 4
　　* in C5D5N; glc: 102. 2, 75. 3, 78. 6, 71. 7, 78. 5, 62. 9
( 1H, s, 4′-OH) , 8. 42 ( 1H, s, H-2) , 7. 40 ( 2H,
d, J= 9 Hz, H-2′, 6′) , 6. 83 ( 2H, d, J= 9 Hz, H-
3′, 5′) , 6. 72 ( 1H, br. s, H-8) , 6. 48 ( 1H, br. s,
H-6) , 5. 06 ( 1H, d, J= 7 Hz, H-1″) .
Compound Ⅵ : White needles. mp 194℃～
195℃ . 1 HNM Rδ( 300 MHz, CDCl3 ): 5. 50 ( 1H,
br. s, H-12) , 4. 57 ( 1H, s, H-15) , 1. 22, 1. 17,
1. 02, 1. 02, 0. 975, 0. 863, 0. 850, 0. 819 ( each
3H, s, 8× CH3 ) .
References:
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[6 ]　Ohshima Y, Oku yama T, Takahashi K, et al . Is olation and
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2355.
栝楼化学成分的研究及其α-菠菜甾醇的含量测定 (Ⅰ )
时岩鹏 ,姚庆强* ,刘拥军 ,韦兴光 ,王保国* * ,栾　杨
(山东省医学科学院药物研究所 ,山东 济南　 250062)
摘　要: 目的　研究栝楼 Trichosanthes k irilowii Maxim. 的化学成分并建立栝楼中α-菠菜甾醇的含量测定方法。方
法　采用反复硅胶柱层析分离纯化 ,通过理化常数测定和光谱分析鉴定其化学结构。 采用双波长薄层扫描法研究
·14· 中草药　 Chinese T raditional and Herbal Drug s　 2002年第 33卷第 1期
收稿日期: 2001-04-20基金项目:山东省自然科学基金研究课题资助 ( No. Q99C08)作者简介:时岩鹏 ( 1973-) ,男 ,河北邢台人 ,助理研究员 , 1995年毕业于河北医科大学获学士学位 , 1998年毕业于山东省医学科学院获硕士学位 , 1998年至今在山东省医学科学院药物研究所工作 ,主要研究方向为心血管药物和抗肿瘤药物的研究与开发。 Tel:
2919970　　 E-mail: ypshi@ yeah. n et
* 课题负责人
* * 山东医科大学 99级本科实习生