全 文 ：天然产物研究与开发 Nat Prod Res Dev 2011，23:643-646
文章编号:1001-6880(2011)04-0643-04
Received October 10，2009，Accepted November 24，2009
Foundation Item:This research project was supported by the Scientific
Foundation of Shanghai China (08DZ1971302)．
* Corresponding author Tel:86-21-34205989;E-mail:wdzhangy@ hot-
mail． com
线叶旋覆花的化学成分研究
聂利月1，金慧子1，严 岚1，覃江江1，张卫东1，2*
1上海交通大学药学院，上海 200240;2 第二军医大学药学院，上海 200433
摘 要:从线叶旋覆花(Inula lineariifolia Turcz．)地上部分的乙醇提取物中分离得到 13 个化合物，通过波谱学方
法及参考文献对照分别鉴定为泽兰黄醇素(1)、菠叶素(2)、刚毛黄酮(3)、胡萝卜苷(4)、β-谷甾醇(5)、α-菠菜
甾醇(6)、蒲公英甾醇乙酰酯(7)、(+)-丁香脂素(8)、去氢催叶萝芙叶醇(9)、安息香醛(10)、香荚兰醛(11)、4-
羟基-3，5-二甲氧基苯甲醛(12)和 4-羟基-2，6-二甲氧基苯甲醛(13)。化合物 1 ～ 13 均为首次从该植物中分离
得到。
关键词:线叶旋覆花;乙醇提取物;化学成分
中图分类号:Q946． 91;R284． 2 文献标识码:A
Chemical Constituents of Inula lineariifolia Turcz．
NIE Li-yue1，JIN Hui-zi1，YAN Lan1，QIN Jiang-jiang1，ZHANG Wei-dong1，2*
1Shanghai Jiao Tong University，Shanghai 200240，China;2Second Military Medical University，Shanghai 200433，China
Abstract:Thirteen compounds were isolated from the ethanol extract of the aerial part of Inula lineariifolia Turcz． ． On
the basis of spectral analysis and comparison with the relative literatures，their structures were identified respectively as
eupatin (1) ，spinacetin (2) ，hispidulin (3) ，daucosterol (4) ，β-sitosterol (5) ，α-spinasterol (6) ，taraxasteryl acetate
(7) ，(+)-syringaresinol (8) ，dehydrovomifoli (9) ，4-hydroxy-benzaldehyde(10) ，vanllin polymer (11) ，4-hydroxy-3，
5-dimethoxybenzaldehyde (12) ，and 4-hydroxy-2，6-dimethoxybenzaldehyde (13)． All compounds were isolated from I．
lineariifolia for the first time．
Key words:Inula lineariifolia Turcz．;ethanol extract;chemical constituents
Introduction
A number of plants in Inula genus are used as tradi-
tional herbal medicines to treat expectorant，anti-tus-
sive，diaphoretic，and bactericidal throughout the
world． Recently，much attention has been paid to Inula
genus due to their diverse biological activities，particu-
larly in anti-tumor application ［1］． Actually，the investi-
gation of the chemical constituents of Inula plants is the
major course in our group，and many bioactive com-
pounds have been reported ［2，3］． However，as far as In-
ula lineariifolia Turcz． is concerned，only a few com-
pounds have been isolated from this plant ［4］． Herein，
we report the isolation and elucidation of 13 com-
pounds:eupatin (1) ，spinacetin (2) ，hispidulin (3) ，
daucosterol (4) ，β-sitosterol (5) ，α-spinasterol (6) ，
taraxasteryl acetate (7) ，(+)-syringaresinol (8) ，de-
hydrovomifoli (9) ，4-hydroxy-benzaldehyde(10) ，vanl-
lin polymer (11) ，4-hydroxy-3，5-dimethoxybenzalde-
hyde (12) ，and 4-hydroxy-2，6-dimethoxybenzaldehyde
(13)． All compounds were isolated from I． lineariifolia
for the first time．
Experimental
General procedures
Melting points were carried out on a RY-1 micro-melt-
ing point apparatus without correction． The ESIMS were
recorded on Agilent-1100-LC /MSD-Trap (ESI-MS)
and Agilent Micro-Q-Tof in m/z． NMR spectra were
measured on a Bruker DRX-500 spectrometer with TMS
as internal standard，operating at 500 MHz for 1H and
125 MHz for 13C chemical shift (δ)was given in ppm
and coupling constants in Hz． Column chromatographies
(CC)were performed on silica gel (200-300 mesh，
DOI:10.16333/j.1001-6880.2011.04.042
Yantai，China)and sephadex LH-20 (GE Healthcare
Bio-Sciences AB，Sweden) ，and precoated silica GF254
plates were used for TLC (Qingdao Haiyang Chemical
Co．，Ltd．，China)．
Plant material
The whole plants of I． lineariifolia Turcz． were collected
in Changfeng County，Anhui Province，in late July
2007，and authenticated by Prof． Shou-Jin Liu (Anhui
University of Traditional Chinese Medicine)． A voucher
specimen (No． XX20070701) is deposited in the
School of Pharmacy，Shanghai Jiao Tong University．
Extraction and isolation
The air-dried and powdered aerial part of I． lineariifolia
Turcz (60． 0 kg)was extracted with 95% ethanol (3
× 10 L)． Then the concentrated residue was suspen-
ded in H2O and partitioned with petroleum ether
(PE) ，CHCl3，EtOAc，and n-BuOH successively． Part
of PE extract (116． 8 g from 1000． 0 g)was subjected
to silica CC eluting with a gradient of PE-EtOAc (100
∶ 1-1∶ 2)to give 14 fractions (Fr． 1-Fr． 14)based on
TLC analysis． Compounds 4 (67． 2 mg) ，5 (25． 2
mg) ，6 (30． 0 mg) ，and 7 (25 mg)were separated
from Fr． 10，Fr． 2，and Fr． 1 respectively． Part of CHCl3
extract (240 g from 600． 0 g)was chromatographed o-
ver silica gel ，eluting with increasing amounts of
MeOH (0-100%)in CH2Cl2，to afford 11 fractions (
F1-F11)． Fractions F1，F4，and F5 were further subjec-
ted to sephadex LH-20 with MeOH as eluent to give the
subfractions as follows:F1a-1d，F4a-4h，F5a-5f． The
F1c，F4b，and F4i were further purified by preparative
HPLC under MeOH-H2O system． F1c gave 10 (2． 8
mg) ，11 (5． 7 mg) ，12 (8． 3 mg) ，and 13 (15． 1 mg)
by prep-HPLC with MeOH /H2O system (20%) ，F4i
gave 9 (2． 6 mg)at MeOH /H2O (35%) ，and F4b
gave 8 (11． 0 mg)at MeOH /H2O (45%)． F5f was
subjected to sephadex LH-20 eluted with MeOH repeat-
edly to yield 1 (23． 2 mg) ，2 (40． 5 mg) ，and 3 (4． 2
mg)．
Structure identification
Compound 1 C18 H16 O8，yellow amorphous solid
(MeOH) ，mp． 206-209 ℃，ESI-MS (pos. )m/z 383. 1
［M + Na］+，ESI-MS (neg. ) m/z 359. 0［M –
H］–;1H NMR (DMSO-d6 + CDCl3，500 MHz) δ:
7. 79 (1H，d，J = 1. 5 Hz，H-6) ，7. 73 (1H，dd，J =
8. 5，1. 5 Hz，H-2) ，7. 03 (1H，d，J = 1. 5 Hz，H-5) ，
6. 91 (1H，s，H-8) ，4. 04，4. 00，3. 91 (3 × 3H，s，C-6，
C-7，C-4-OCH3) ;
13 C NMR (DMSO-d6 + CDCl3，125
MHz)δ:150. 5 (C-2) ，138. 8 (C-3) ，179. 3 (C-4) ，
150. 2 (C-5) ，131. 2 (C-6) ，156. 9 (C-7) ，91. 4 (C-
8) ，155. 2 (C-9) ，106. 6 (C-10) ，123. 2 (C-1) ，
116. 2 (C-2) ，147. 2 (C-3) ，148. 8 (C-4) ，112. 6
(C-5) ，122. 3 (C-6) ，60. 2 (7-OCH3) ，56. 7 (7-
OCH3) ，56. 3 (4-OCH3). The NMR data was in ac-
cordance with those reported in the literature ［5］，and i-
dentified 1 as eupatin.
Compound 2 C17 H14 O8，yellow needles (MeOH) ，
mp． 122-124 ℃ . ESI-MS (pos. )m/z 347. 1［M +
H］+;ESI-MS (neg. )m/z 345. 1［M-H］–;1H NMR
(DMSO-d6，500 MHz)δ:12. 37 (1H，s，H-5) ，7. 59
(1H，s，H-2) ，7. 47 (1H，d，J = 10. 0 Hz，H-6) ，
6. 91 (1H，d，J = 10. 0 Hz，H-5) ，6. 83 (1H，s，H-8) ，
3. 79，3. 90 (2 × 3H，s，C-6，C-3-OCH3) ;
13 C NMR
(DMSO-d6，125 MHz)δ:145. 7 (C-2) ，137. 5 (C-
3) ，178. 1 (C-4) ，148. 8 (C-5) ，129. 6 (C-6) ，155. 7
(C-7) ，90. 8 (C-8) ，154. 5 (C-9) ，105. 5 (C-10) ，
121. 0 (C-1) ，115. 5 (C-2) ，145. 2 (C-3) ，148. 6
(C-4) ，115. 7 (C-5) ，120. 5 (C-6) 56. 3 (3-
OCH3) ，59. 6 (6-OCH3). The NMR data was in ac-
cordance with those reported in the literature ［5，6］，and
identified 2 as spinacetin.
Compound 3 C16 H12 O6，yellow amorphous solid
(MeOH) ，mp． 244-247 ℃，ESI-MS (neg. ) m/z
299. 1［M– H］–;1H NMR (DMSO-d6，500 MHz)δ:
3. 75 (3H，s，6-OCH3) ，6. 59 (1H，s，H-3) ，6. 78
(1H，s，H-8) ，6. 93 (2H，d，J = 10. 0 Hz，H-3，5) ，
7. 93 (2H，d，J = 10. 0 Hz，H-2，6) ，10. 30 (1H，s，
4-OH) ，10. 70 (1H，s，7-OH) ，13. 10 (1H，s，5-
OH) ;13C NMR (DMSO-d6，125 MHz)δ:163. 8 (C-
2) ，102. 3 (C-3) ，182. 4 (C-4) ，152. 7 (C-5) ，131. 3
(C-6) ，157. 3 (C-7) ，94. 2 (C-8) ，152. 4 (C-9) ，
104. 0 (C-10) ，121. 2 (C-1) ，128. 4 (C-2) ，115. 9
(C-3) ，161. 1 (C-4) ，115. 9 (C-5) ，128. 4 (C-
6) ，56. 3 (6-OCH3). The NMR data was in accord-
ance with those reported in the literature ［7，8］，and i-
dentified 3 as hispidulin.
446 Nat Prod Res Dev Vol. 23
Compound 4 C35 H60 O6，white amorphous powder，
mp． 285-287 ℃，ESI-MS m/z 599. 6［M + Na］+ . TLC
behavior was in accordance with that of authentic dau-
costerol when eluted with different developing
solvents. Thus，compound 4 was determined as dau-
costerol.
Compound 5 C29 H50 O，white needles (MeOH) ;
mp. 139-140 ℃;ESI-MS m/z 437. 4［M + Na］+;13 C
NMR (CDCl3，125 MHz)δ:37. 3 (C-1) ，31. 7 (C-
2) ，71. 8 (C-3) ，42. 3 (C-4) ，140. 8 (C-5) ，121. 7
(C-6) ，31. 7 (C-7) ，31. 9 (C-8) ，50. 2 (C-9) ，36. 5
(C-10) ，21. 1 (C-11) ，39. 8 (C-12) ，42. 3 (C-13) ，
56. 8 (C-14) ，24. 3 (C-15) ，28. 2 (C-16) ，56. 1 (C-
17) ，11. 9 (C-18) ，19. 1 (C-19) ，36. 1 (C-20) ，18. 8
(C-21) ，34. 0 (C-22) ，26. 1 (C-23) ，45. 9 (C-24) ，
29. 2 (C-25) ，19. 8 (C-26) ，19. 4 (C-27) ，23. 1 (C-
28) ，12. 0 (C-29). The above data were in accordance
with those reported in the lierature ［9］. Therefore，com-
pound 5 was identified as β-sitosterol.
Compound 6 C29 H48 O，white needle crystal
(CH2Cl2) ，mp． 160-162 ℃;ESI-MS m/z 413［M +
H］+ . Compound 6 showed the same color and equal Rf
value with standard substance of α-spinasterol when
applied on TLC and eluted with different developing
solvents. So compound 6 was characterized as α-spinas-
terol.
Compound 7 C32 H52 O2，white lamellar solid(PE) ，
mp． 237-239 ℃，ESI-MS (neg. )m/z 935. 5 ［2M –
H］–;1H NMR (CDCl3，500 MHz)δ:4. 62 (2H，m，
H-30) ，4. 48 (1H，dd，J = 12. 5，3. 0 Hz) ，2. 04 (3H，
s，CH3CO) ，1，01 (3H，d，J = 8. 5 Hz，H-29) ，1. 00
(3H，s，H-26) ，0. 90 (3H，s，H-27) ，0. 85 (3H，s，H-
23) ，0. 82 (3H，s，H-25) ，0. 82 (3H，s，H-25) ，0. 82
(3H，s，H-28) ，0. 81 (3H，s，H-24) ;13 C NMR
(CDCl3，125 MHz)δ:38. 5 (C-1) ，26. 7 (C-2) ，81. 0
(C-3) ，37. 8 (C-4) ，55. 5 (C-5) ，18. 2 (C-6) ，34. 0
(C-7) ，40. 9 (C-8) ，50. 4 (C-9) ，37. 1 (C-10) ，21. 5
(C-11) ，25. 6 (C-12) ，39. 2 (C-13) ，42. 0 (C-14) ，
26. 2 (C-15) ，38. 3 (C-16) ，34. 5 (C-17) ，48. 7 (C-
18) ，39. 4 (C-19) ，154. 6 (C-20) ，23. 7 (C-21) ，
38. 9 (C-22) ，27. 9 (C-23) ，15. 9 (C-24) ，16. 3 (C-
25) ，16. 5 (C-26) ，14. 7 (C-27) ，19. 5 (C-28) ，
107. 1 (C-29) ，25. 4 (C-30) ，171. 0 (CH3CO) ，21. 3
(CH3CO ). The NMR data was in accordance with
those reported in the literature ［10］，and identified 7 as
taraxasteryl acetate.
Compound 8 C22 H26 O8，white powder (MeOH) ，
mp. 118-120 ℃，ESI-MS (pos. )m/z 441. 2 ［M +
Na］+;1H NMR (CDCl3，500 MHz)δ:6. 58 (4H，s，
H-2，H-8，H-2，H-8) ，4. 73 (2H，d，J = 3. 75 Hz，H-
7，H-7) ，4. 27 (2H，m，He-9，He-9) ，3. 92 (2H，m，
Ha-9，Ha-9) ，3. 89 (12H，s，4 × OCH3) ，3. 09 (2H，
m，H-8，H-8) ;13C NMR (CDCl3，125 MHz)δ:132. 1
(C-1，C-1) ，102. 7 (C-2，C-2) ，147. 1 (C-3，C-3) ，
134. 3 (C-4，C-4) ，86. 1(C-7，C-7) ，71. 8 (C-9，C-
9) ，56. 4 (4 × OCH3) ，54. 3 (C-8，C-8). The spec-
tral data was identical with those reported in the litera-
ture ［11］，and 8 was determined as (+ )-syringares-
inol.
Compound 9 C13H18O3，light yellow gum (MeOH) ，
ESI-MS (pos. )m/z 245. 1 ［M + Na］+;1H NMR
(CDCl3，500 MHz)δ:1. 01，1. 09 (each 3H，each s，
H3-1，H3-2) ，1. 89 (3H，d，J = 1. 5 Hz，H-5) ，2. 31
(3H，s，H-9) ，5. 96 (1H，s，H-4) ，6. 47 (1H，d，J =
15. 5 Hz，H-8) ，6. 82 (1H，d，J = 15. 5 Hz，H-7) ;13 C
NMR (CDCl3，125 MHz)δ:41. 4 (C-1) ，49. 6 (C-
2) ，196. 9 (C-3) ，144. 9 (C-4) ，160. 2 (C-5) ，79. 3
(C-6) ，127. 8 (C-7) ，130. 4 (C-8) ，197. 3 (C-9) ，
18. 6 (C-10) ，22. 9 (C-11) ，24. 32 (C-12) ，28. 4 (C-
13). The spectral data was identical with those reported
in the literature ［12，13］，and identified as dehydrovomifo-
li.
Compound 10 C7H6O2，colorless oil (CH2Cl2) ，ESI-
MS m/z 245. 3［2M + H］+;121. 1［M – H］–;1H
NMR (CDCl3，500 MHz)δ:9. 61 (1H，m，H-1) ，7. 68
(2H，d，J = 9. 0 Hz，H-2，H-6) ，6. 77 (2H，d，J = 9. 0
Hz，H-3，H-5). Compound 10 was characterized as 4-
hydroxy-benzaldehyde by spectral analysis and compar-
ison with standard substance of 4-hydroxy-benzalde-
hude when applied on TLC and eluted with different
developing solvents.
Compound 11 C8H8O3，colorless oil，ESI-MS m/z
175. 2［M + Na］+;151. 0［M – H］–;1H NMR
(CDCl3，500 MHz) δ:9. 59 (1H，m，H-1) ，7. 38
(2H，m，H-2，H-6) ，6. 79 (1H，d，J = 3. 0 Hz) ，3. 88
546Vol. 23 NIE Li-yue，et al:Chemical Constituents of Inula lineariifolia Turcz．
(3H，s，3-OCH3). Compound 11 was characterized as
vanllin polymer by spectral analysis and comparison
with standard substance when applied on TLC and elu-
ted with different developing solvents.
Compound 12 C9H10O4，light yellow oil，ESI-MS m/
z 205. 2［M + Na］+;1H NMR (CD3OD，500 MHz)δ:
9. 70 (1H，m，H-1) ，7. 21 (2H，s，H-2，H-6) ，3. 91
(6H，s，3，5-OCH3). Compound 12 was characterized
as 4-hydroxy-3，5-dimethoxy-benzaldehyde by spectral
analysis and comparison with standard substance when
applied on TLC and eluted with different developing
solvents.
Compound 13 C9H10O4，light yellow oil，ESI-MS m/
z 205. 2 ［M + Na］+;181. 1 ［M-H］–;1H NMR
(CDCl3，500 MHz)δ:5. 86 (2H，s，H-2，H-6) ，3. 83
(6H，s，2，4-OCH3). Compound 13 was characterized
as 4-hydroxy-2，6-dimethoxy-benzaldehyde by spectral
analysis and comparison with standard substance when
applied on TLC and eluted with different developing
solvents.
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