全 文 ：Received April 5，2012;Accepted July 20，2012
Foundation Item:This work was supported by the Natural Science
Foundation of China (NSFC，No． 21162023)and Bingtuan Interna-
tional Cooperation Projects (No． 2011BC003)．
* Corresponding author Tel:86-993-2058099;E-mail:yhb tea@ shzu．
edu． cn
天然产物研究与开发 Nat Prod Res Dev 2012，24:1738-1742
文章编号:1001-6880(2012)12-1738-05
角果藜的化学成分研究
刘珊珊1，孙 文1，杨红兵1* ，孙万赋2
1新疆兵团化工绿色过程重点实验室 石河子大学化学化工学院，石河子 832003;
2新疆大学理化测试中心，乌鲁木齐 830046
摘 要:从新疆特色植物角果藜(Ceratocarpus arenarius L．)地上部分乙醇提取物的乙酸乙酯和氯仿萃取部分共
分离得到 11 个化合物，通过波谱数据结合理化性质分别鉴定为 7-酮基-β-谷甾醇(1)、β-谷甾醇(2)、豆甾-3-O-β-
D-吡喃葡萄糖苷(3)、正十六碳醇(4)、［24S］豆甾-4-烯-3-酮(5)、173-脱镁叶绿素乙酯(6)、麦黄酮(7)、穆坪马
兜铃酰胺(8)、邻苯二甲酸二(2-乙基己基)酯(9)、β-谷甾醇亚油酸酯(10)、丁香树脂酚葡萄糖苷(11)。所有化
合物均为首次从该植物中分离得到。
关键词:藜科;角果藜;黄酮;生物碱;甾醇
中图分类号:R284. 2 文献标识码:A
Chemical Constituents of Ceratocarpus arenarius L．
LIU Shan-shan1，SUN Wen1，YANG Hong-bing1* ，SUN Wan-fu2
1Xinjiang Bingtuan Key Laboratory for Green Processing of Chemical Engineering，School of Chemistry and Chemical
Engineering，Shihezi University，Shihezi 832003，China;2Analysis and Research Center，Xinjiang University，Urumqi 830046，China
Abstract:Eleven compounds were isolated and elucidated from Ceratocarpus arenarius L． (Chenopodiaceae)． Their
structures were identified as 7-Oxo-β-sitosterol (1) ，β-sitosterol (2) ，stigmasteryl-3-O-β-D-glucopyranoside (3) ，n-
hexadecanol (4) ，［24S］stigmast-4-en-3-one (5) ，173-ethoxyphaeophorbidea (6) ，tricin (7) ，moupinamide (8) ，1 2-
benzenedicarboxylic acid，bis(2-ethylhexyl)ester (9) ，β-sitosteryl linoleate (10)and syringaresinol mono-β-D-glucoside
(11)． All of these compounds were isolated from C． arenarius L． for the first time． The above compounds were individu-
ally identified by spectroscopic analyses and comparisons with reported data．
Key words:Chenopodiaceae;Ceratocarpus arenarius L．;flavone;alkaloid;steroids
Introduction
Xinjiang is the largest distribution area of Chenopodi-
aceae plants in China due to its complex geographical
environment and unique climatic conditions． Plants of
Chenopodiaceae family are closely related to human
life． For example，Beta vulgaris is the raw material for
sugar manufacture;Chenopodium ambrosioides and Sal-
sola collina are pharmaceutical raw materials;Anabasis
aphylla is raw material for agricultural insecticide man-
ufacture．
Ceratocarpus arenarius L． is an annual herb belonging
to genus Ceratocarpus of Chenopodiaceae and is only
distributed in Xinjiang in China． Current studies on C．
arenarius L． mainly focused on ecology ［1，2］，researches
on its chemical composition had not been reported．
Experimental
General
Melting point was determined on XT4-100B microelting
point apparatus and uncorrected． 1H NMR (400 MHz)
and 13C NMR (100 MHz)spectra were recorded on a
Bruker-DMX 400 spectrometer in CDCl3，DMSO-d6 and
CD3OD，with TMS as an internal standard and reported
in ppm (δ)． Column chromatograph was performed
with silica gel (200-300 mesh，Zhigao Huangwu Chem-
ical Co．，China)and Sephadex LH-20(GE healthcare
Bio-science AB)． TLC on silica gel GF254 was detected
with I2 and 5%H2SO4-EtOH solution．
Plant material
DOI:10.16333/j.1001-6880.2012.12.010
C． arenarius L． sample was collected from Manasi in
Xinjiang，in September 2009，and was identified by
Professor Yan Ping of Shihezi Unverisity． A voucher
specimen had been kept in the laboratory for future ref-
erence． All plant materials were dried at room tempera-
ture and divided into small pieces before extraction．
Extraction and isolation
The air-dried aerial parts of C． arenarius L． (10 kg)
were exhaustively extracted with alcohol at room tem-
perature． The extract was evaporated under reduced
pressure． The EtOH extract (1501． 01 g)was then ex-
tracted with petroleum ether，ethyl acetate，chloroform
and n-butanol．
The ethyl acetate extract (300 g)was subjected to a
silica gel column chromatography using different sol-
vent systems and yielded 8 fractions． Fractions 1-3 were
not further purified because of low polarity． Compound
1 (8． 9 mg)was obtained from fraction 5 after subjec-
ting to column chromatography eluted with petroleum e-
ther-acetone (1 ∶ 0;6 ∶ 1)as white powder． Fraction 6
was subjected to column chromatography using petrole-
um ether-acetone (1 ∶ 0;3 ∶ 1)and Sephadex LH-20
column eluting with CHCl3-MeOH (1∶ 1) ，compound 2
(35． 8 mg)was obtained as white needle． Fraction 7
was subjected to silica gel column chromatography to
give compound 3 (30 mg)． Compound 6 (25 mg)was
obtained from fraction 8 eluted with n-hexane-EtOAc
(6∶ 1)． Compounds 4 (15 mg)and 5 (20 mg)were
obtained from fraction 4 after subjecting to repeated
column chromatography using petroleum ether-acetone
(1∶ 0;10∶ 1;5∶ 1)．
Chloroform extract (12． 06 g)was subjected to column
chromatography on silica gel，six fractions were ob-
tained by gradient elution with EtOAc-MeOH (1∶ 0;80
∶ 1-20 ∶ 1)． Fraction 1 was further separated by silica
gel column chromatography and eluted with n-hexane-
EtOAc (9∶ 1)to give compound 7 (16 mg)as yellow
powder． Similarly，Compound 8 (30． 1 mg)was isola-
ted from fraction 2 eluting with CHCl3-MeOH (7∶ 3)as
white needle． Compound 9 (20 mg)was obtained from
fraction 3 after subjecting to column chromatography e-
luted with CHCl3-MeOH (1∶ 0;80∶ 1)as colorless oil．
Repeated column chromatography of fractions 4-6 elu-
ting with CHCl3-MeOH (1 ∶ 0;15 ∶ 1;9 ∶ 1)afforded
compound 10 (11 mg)and compound 11 (14 mg)．
Structural identification
Compound 1 White powder (EtOAc) ，mp 120-123
oC;1H NMR (400 MHz，CDC13)δ:5. 69 (1H，br. s，
H-6) ，3. 68 (1H，tt，J = 5. 2，10. 8 Hz，H-3) ，2. 52
(1H，ddd，J = 2. 0，5. 1，12. 9 Hz，H-4α) ，2. 40 (1H，
ddt，J = 2. 0，11. 0，13. 2 Hz，H-4β) ，2. 24 (1H，t，J
= 12. 0 Hz，H-8) ，2. 05 (1H，dt，J = 4. 2，12. 5 Hz，
H-12β) ，1. 20 (3H，s，H-19) ，0. 94 (3H，d，J = 7. 0
Hz，H-21) ，0. 87 (3H，d，J = 6. 5 Hz，H-27) ，0. 82
(3H，t，J = 7. 0 Hz，H-29) ，0. 68 (3H，s，H-18 ) ;13C
NMR (100 MHz，CDC13)δ:202. 4 (C-7) ，165. 2 (C-
5 ) ，126. 1 (C-6) ，70. 5 (C-3) ，54. 7 (C-17) ，49. 9
(C-9，14) ，45. 8 (C-24) ，45. 4 (C-8) ，43. 1 (C-13) ，
41. 8 (C-14) ，38. 7 (C-12) ，38. 3 (C-10) ，36. 3 (C-
1) ，36. 1 (C-20) ，33. 9 (C-22) ，31. 2 (C-2) ，29. 1
(C-25) ，28. 5 (C-16) ，26. 3 (C-15) ，26. 0 (C-23) ，
23. 0 (C-28) ，21. 2 (C-11) ，19. 8 (C-27) ，19. 0 (C-
26) ，18. 9 (C-21) ，17. 3 (C-19) ，12. 0 (C-18，29)．
The spectral data were matched with literature ［3］，
hence it was identified as 7-Oxo-β-sitosterol.
Compound 2 White needle (EtOAc) ，mp 137-139
oC;TLC and IR spectrum were identical to those of au-
thentic sample;1H NMR (400 MHz，CDCl3)δ:5. 33
(1H，br. d，J = 5. 2 Hz，H-6) ，3. 50 (1H，m，H-3) ，
0. 99 (3H，s，H-19) ，0. 90 (3H，d，J = 6. 6 Hz，H-
21) ，0. 84 (3H，t，J = 7. 5 Hz，H-29) ，0. 80 (3H，d，J
= 6. 9 Hz，H-27) ，0. 78 (3H，d，J = 6. 9 Hz，H-26) ，
0. 69 (3H，s，H-18) ;13C NMR (100 MHz，CDCl3)δ:
140. 8 (C-5) ，121. 7 (C-6) ，71. 8 (C-3) ，56. 8 (C-
14) ，56. 0 (C-17) ，50. 1 (C-9) ，45. 8 (C-24) ，42. 3
(C-13) ，42. 2 (C-4) ，39. 8 (C-12) ，37. 2 (C-1) ，
36. 5 (C-10) ，36. 1 (C-20) ，33. 9 (C-22) ，31. 9 (C-
8) ，31. 9 (C-7) ，31. 7 (C-2) ，29. 1 (C-23) ，28. 2
(C-16) ，26. 1 (C-25) ，24. 3 (C-15) ，23. 1 (C-28) ，
21. 2 (C-11) ，19. 8 (C-27) ，19. 4 (C-19) ，19. 0 (C-
21) ，18. 8 (C-26) ，11. 9 (C-18) ，11. 8 (C-29). The
data were in accordance with β-sitosterol ［4，5］.
Compound 3 White amorphous powder (EtOAc) ，
mp 264-266 oC;Liebermann-Burchard reaction showed
blue-green result;1H NMR (400 MHz，DMSO-d6)δ:
9371Vol. 24 LIU Shan-shan，et al:Chemical Constituents of Ceratocarpus arenarius L．
5. 33 (2H，br. d，J = 5. 2 Hz，H-22，23) ，5. 16 (1H，
m，H-6) ，4. 90 (1H，d，J = 4. 8 Hz，H-1) ，4. 43
(1H，t，J = 5. 6 Hz，H-4) ，0. 95 (3H，s，H-19) ，
0. 90 (3H，d，J = 6. 4 Hz，H-21) ，0. 83 (3H，dd，J
= 2. 8，7. 2 Hz，H-29) ，0. 78 (3H，d，J = 4. 0 Hz，H-
27) ，0. 66 (3H，d，J = 8. 0 Hz，H-26) ，0. 62 (3H，s，
H-18) ;13C NMR (100 MHz，DMSO-d6)δ:140. 7 (C-
5) ，138. 3 (C-22) ，129. 0 (C-23) ，121. 4 (C-6) ，
100. 8 (C-1) ，77. 1 (C-3) ，76. 9 (C-3) ，76. 7 (C-
5) ，73. 7 (C-2) ，70. 3 (C-4) ，61. 3 (C-6) ，56. 4
(C-14) ，55. 6 (C-17) ，49. 8 (C-9) ，45. 4 (C-24) ，
41. 9 (C-13) ，39. 1 (C-12) ，38. 5 (C-4) ，37. 0 (C-
1) ，36. 4 (C-10) ，35. 7 (C-20) ，31. 6 (C-7) ，31. 3
(C-8) ，29. 4 (C-2) ，28. 9 (C-25) ，27. 7 (C-16) ，
24. 0 (C-15) ，22. 8 (C-28) ，20. 8 (C-11) ，19. 9 (C-
26) ，19. 3 (C-19) ，19. 1 (C-27) ，18. 8 (C-21) ，12. 0
(C-29) ，11. 9 (C-18). Compound 3 was identified as
stigmasteryl-3-O-β-D-glucopyranoside by a comparison
of its spectral data and physical properties with those
reported ［6，7］.
Compound 4 Colorless solid (EtOAc) ;1H NMR
(400 MHz，CDCl3)δ:3. 64 (2H，t，J = 13. 2 Hz，H-
1) ，1. 57 (2H，t，J = 6. 4 Hz，H-2) ，1. 38-1. 19
(26H，br. s，H-3 ～ H-14) ，0. 89 (3H，t，J = 8. 4 Hz，
H-16) ;13C NMR (100 MHz，CDCl3)δ:63. 1 (C-1) ，
32. 8 (C-2) ，31. 9 (C-14) ，29. 7 (C-5，13) ，29. 7 (C-
6 ～ C-12) ，29. 4 (C-4) ，25. 8 (C-3) ，22. 7 (C-15) ，
14. 1 (C-16). The spectral data were matched with the
reported ［8］，hence it was identified as n-hexadecanol.
Compound 5 White needle crystal (EtOAc) ;1H
NMR (400 MHz，CDCl3)δ:5. 72 (1H，br. s，H-4) ，
1. 18 (3H，s，H-19) ，0. 91 (3H，d，J = 6. 4 Hz，H-
21) ，0. 84 (3H，t，J = 7. 2 Hz，H-29) ，0. 81 (3H，d，J
= 7. 2 Hz，H-26) ，0. 73 (3H，d，J = 6. 6 Hz，H-27
) ，0. 71 (3H，s，H-18 ) ;13C NMR (400 MHz，CDC13)
δ:199. 7 (C-3) ，171. 8 (C-5) ，123. 8 (C-4) ，56. 0
(C-17) ，55. 9 (C-14) ，53. 8 (C-9) ，45. 8 (C-24) ，
42. 4 (C-13) ，39. 6 (C-12) ，38. 6 (C-10) ，36. 1 (C-
20) ，35. 7 (C-8) ，35. 6 (C-1) ，34. 0 (C-22) ，33. 9
(C-2) ，33. 0 (C-6) ，32. 1 (C-7) ，29. 7 (C-25) ，29. 1
(C-16) ，28. 2 (C-23) ，26. 1 (C-15) ，24. 2 (C-28) ，
23. 1 (C-11) ，21. 0 (C-26) ，19. 8 (C-27) ，19. 0 (C-
19) ，18. 7 (C-21) ，17. 4 (C-29) ，11. 9 (C-18). The
spectral data were matched with literature ［9］，hence it
was identified as［24S］stigmast-4-en-3-one.
Compound 6 Black-green solid (EtOAc) ;1H NMR
(400 MHz，CDCl3) δ:9. 50 (1H，s，H-10) ，9. 35
(1H，s，H-5) ，8. 56 (1H，s，H-20) ，7. 97 (1H，dd，J
= 11. 6，18. 0 Hz，H-31) ，6. 30 (1H，d，J = 1. 6 Hz，
H-32(E) ) ，6. 27 (1H，s，H-132) ，6. 19 (1H，d，J =
1. 2 Hz，H-32(Z) ) ，4. 40 (1H，m，H-18) ，4. 23 (1H，
m，H-17) ，4. 05 (2H，m，H-174) ，3. 89 (3H，s，H-
134) ，3. 69 (3H，s，H-121) ，3. 66 (2H，q，J = 5. 6
Hz，H-81) ，3. 40 (3H，s，H-21) ，3. 21 (3H，s，H-71) ，
1. 82 (3H，d，J = 7. 2 Hz，H-181) ，1. 69 (3H，t，J =
7. 6 Hz，H-82) ，1. 11 (3H，t，J = 7. 2 Hz，H-175) ;13C
NMR (100 MHz，CDCl3)δ:189. 6 (C-13
1) ，172. 9
(C-133) ，172. 1 (C-173) ，169. 6 (C-19) ，161. 2 (C-
16) ，155. 6 (C-6) ，151. 0 (C-9) ，149. 6 (C-14) ，
145. 2 (C-8) ，142. 1 (C-1) ，137. 9 (C-11) ，136. 5
(C-3) ，136. 3 (C-4) ，136. 1 (C-7) ，131. 9 (C-2) ，
129. 0 (C-13) ，129. 0 (C-12) ，129. 0 (C-31) ，122. 8
(C-32) ，105. 1 (C-15) ，104. 4 (C-10) ，97. 5 (C-5) ，
93. 1 (C-20) ，64. 7 (C-132) ，60. 5 (C-174) ，52. 9
(C-134) ，51. 1 (C-17) ，50. 1 (C-18) ，31. 1 (C-172) ，
29. 8 (C-171) ，23 (C-181) ，19. 4 (C-81) ，17. 4 (C-
82) ，14. 0 (C-175) ，12. 1 (C-21) ，12. 1 (C-121) ，
11. 2 (C-71). Compound 8 was identified as 173 –
ethoxyphaeophorbidea by comparison of its spectral da-
ta and physical properties with those reported ［10，11］.
Compound 7 Yellow powder (chloroform) ，mp:291-
292 oC;1H NMR (400 MHz，DMSO-d6) δ:12. 96
(1H，s，H-5) ，10. 84 (1H，s，H-7) ，9. 28 (1H，s，H-
4) ，7. 32 (2H，s，H-2，6) ，6. 96 (1H，s，H-3) ，6. 56
(1H，d，J = 1. 6 Hz，H-8) ，6. 21 (1H，d，J = 2. 0
Hz，H-6) ，3. 89 (6H，s，2 × OMe) ;13 C NMR (100
MHz，DMSO-d6) δ:181. 7 (C-4) ，164. 0 (C-2) ，
163. 5 (C-7) ，161. 3 (C-5) ，157. 2 (C-9) ，148. 1 (C-
3，5) ，139. 8 (C-4) ，120. 3 (C-1) ，104. 3 (C-2，
6) ，103. 6 (C-10) ，103. 5 (C-3) ，98. 7 (C-6) ，94. 1
(C-8) ，56. 3 (C-OMe). The data were in accordance
with tricin ［12，13］.
Compound 8 White needle (chloroform) ，mp:87-89
oC;IR (KBr)cm-1:3340，3230，3020，1650，1590，
1550，1510，1460，1380，1360，1280，1160，1120，
1030，980，805;1H NMR (400 MHz，CD3OD)δ:7. 43
0471 Nat Prod Res Dev Vol. 24
(1H，d，J = 15. 6 Hz，H-7) ，7. 06 (1H，br. s，-
NH-) ，7. 05 (1H，d，J = 2. 0 Hz，H-2) ，7. 00 (2H，
d，J = 8. 0 Hz，H-2，6) ，6. 76 (1H，dd，J = 2. 0，8. 1
Hz，H-6) ，6. 69 (1H，d，J = 8. 2 Hz，H-5) ，6. 43
(2H，d，J = 8. 6 Hz，H-3，5) ，6. 40 (1H，d，J =
15. 6 Hz，H-8) ，3. 81 (3H，s，3-OMe) ，3. 45 (2H，t，
J = 7. 2 Hz，H-8) ，2. 72 (2H，t，J = 7. 5 Hz，H-7)．
The data were in accordance with those of reported
［14，15］，hence compound 8 was identified as moupi-
namide.
Compound 9 Colorless oil (chloroform) ;GC-MS
(70 eV)m/z:41，57，83，113，131，149，167，279，
390;1H NMR (400 MHz，CDCl3)δ:7. 69 (2H，dd，J
= 3. 2，5. 6 Hz，H-3，6) ，7. 50 (2H，dd，J = 3. 2，5. 6
Hz，H-4，5) ，4. 21 (4H，m，H-2，2) ，1. 67 (2H，m，
H-3，3) ，1. 35 (16H，m，H-4，5，6，8，4，5，
6，8) ，0. 89 (12H，m，H-7，7，9，9) ;13 C NMR
(100 MHz，CDCl3)δ:167. 8 (C-1，1) ，132. 5 (C-
1，2) ，130. 9 (C-4，5) ，128. 8 (C-3，6) ，68. 2 (C-2，
2) ，38. 8 (C-3，3) ，30. 4 (C-5，5) ，28. 9 (C-
4，4) ，23. 7 (C-8，8) ，23. 0 (C-6，6) ，14. 1
(C-9，9) ，10. 9 (C-7，7). Compound 9 was iden-
tified as 1，2-benzenedicarboxylic acid，bis(2-ethylhex-
yl)ester by comparison of its spectral data with litera-
ture ［16］.
Compound 10 Pale yellow oil jelly (chloroform) ;1H
NMR (400 MHz，CDCl3)δ:5. 41 (5H，m，H-6，9，
10，12，13) ，4. 17 (1H，m，H-3) ，2. 33 (2H，t，J =
7. 5 Hz，H-11) ，2. 01 (2H，t，J = 14. 0 Hz，H-2) ，
2. 00 (4H，m，H-8，14) ，1. 62 (16H，m，H-3-7，
15-17) ，1. 04 (3H，s，H-19) ，1. 02 (3H，s，H-21) ，
0. 89 (3H，t，J = 6. 3 Hz，H-18) ，0. 88 (3H，m，H-
29) ，0. 85 (3H，s，H-26) ，0. 84 (3H，s，H-27) ，0. 69
(3H，s，H-18) ;13C NMR (100 MHz，CDCl3)δ:173. 5
(C-1) ，146. 3 (C-5) ，138. 3 (C-10) ，129. 3 (C-
12) ，128. 9 (C-13) ，125. 4 (C-9) ，123. 8 (C-6) ，
73. 4 (C-3) ，65. 4 (C-14) ，56. 0 (C-17) ，51. 5 (C-
9) ，49. 4 (C-24) ，42. 8 (C-13) ，41. 7 (C-12) ，39. 2
(C-4) ，37. 5 (C-1) ，37. 1 (C-10) ，37. 0 (C-20) ，
34. 2 (C-2) ，34. 0 (C-22) ，32. 0 (C-7) ，31. 9 (C-
8) ，31. 9 (C-6) ，31. 6 (C-16) ，29. 7 (C-7) ，29. 7
(C-15) ，29. 5 (C-4) ，29. 5 (C-5) ，29. 4 (C-25) ，
28. 8 (C-16) ，28. 0 (C-2) ，27. 7 (C-14) ，27. 4 (C-
8) ，26. 4 (C-23) ，25. 9 (C-11) ，25. 5 (C-3) ，24. 9
(C-15) ，23. 1 (C-28) ，22. 7 (C-17) ，21. 2 (C-11) ，
21. 0 (C-27) ，19. 6 (C-19) ，19. 2 (C-21) ，19. 0 (C-
26) ，14. 1 (C-18) ，12. 3 (C-29) ，12. 0 (C-18)
. Compound 10 was identified as β-sitosteryl linoleate
by comparison of its spectral data with literature ［17］.
Compound 11 Amorphous solid (chloroform) ;TLC
reaction detected glucose;1H NMR (400 MHz，DMSO-
d6)δ:6. 66 (2H，s，H-2，6) ，6. 60 (2H，s，H-2″，
6″) ，5. 80 (1H，dd，J = 4. 0，7. 0 Hz，Glc-1) ，4. 90
(2H，t，J = 4. 5 Hz，H-2，6) ，4. 24 (7H，m，H-4 or H-
8，Glc-2，3，4，6) ，4. 05 (2H，m，H-8 or H-4) ，3. 93
(1H，m，Glc-5) ，3. 82 (6H，m，2 × OMe) ，3. 79 (6H，
m，2 × OMe) ，3. 11 (2H，m，H-1，5) ;13 C NMR (100
MHz，DMSO-d6)δ:152. 8 (C-3，C-5) ，148. 1 (C-
3″，C-5″) ，137. 3 (C-1) ，135. 0 (C-4″) ，133. 8 (C-
4) ，131. 5 (C-1″) ，104. 3 (C-G1) ，103. 8 (C-2，
6) ，102. 8 (C-2″，6″) ，85. 5 (C-6) ，85. 3 (C-2) ，
77. 4 (C-G5) ，76. 7 (C-G3) ，74. 3 (C-G2) ，71. 4 (C-
4，8) ，71. 3 (C-G4) ，61. 1 (C-G6) ，56. 6 (C-1) ，
53. 8 (C-5). From the analysis of NMR spectra and by
comparison with reported spectral data ［18，19］，com-
pound 11 was identified as syringaresinol mono-β-D-
glucoside.
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