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绿茎还阳参化学成分的研究



全 文 :天然产物研究与开发 Nat Prod Res Dev 2012,24:761-763,831
文章编号:1001-6880(2012)06-0761-04
收稿日期:2012-01-04 接受日期:2012-03-09
* 通讯作者 E-mail:huayan@ mail. kib. ac. cn
绿茎还阳参化学成分的研究
华 娟1,骆世洪2,黎胜红2,华 燕1*
1西南林业大学;2 中国科学院昆明植物研究所,昆明 650201
摘 要:采用柱层析和重结晶从药用植物绿茎还阳参(Crepis lignea)丙酮提取物中分离得到 7 个单体化合物,并
根据化合物的理化性质和波谱分析,分别鉴定为:3β-acetoxyurs-13(18)-ene (1) ,lupeol acetate (2) ,4-hydroxy-3-
methoxycinnamaldehyde (3) ,(Z)-2-ethylidene-3-methylsuccinic acid (4) ,olean-12-ene-11α-methoxy-3β-acetate (5) ,
α-amyrin acetate (6)和 lupeol-9(11)en-3β-acetate (7)。上述化合物均为首次从绿茎还阳参中分离得到。
关键词:菊科;还阳参属;绿茎还阳参;三萜
中图分类号:R284. 2 文献标识码:A
Chemical Constituents of Crepis lignea
HUA Juan1,LUO Shi-hong2,LI Sheng-hong2,HUA Yan1*
1Southwest Forest University;2Kunming Institute of Botany,Chinese Academy of Sciences,Kunming 650201,China
Abstract:Seven compounds were isolated from the acetone extract of the medicinal plant Crepis lignea by column chro-
matography and recrystallization. Their structures were mainly identified by their spectral and physical data as 3β-ace-
toxyurs-13(18)-ene (1) ,lupeol acetate (2) ,4-hydroxy-3-methoxycinnamaldehyde (3) ,(Z)-2-ethylidene-3-methylsuc-
cinic acid (4) ,olean-12-ene-11α-methoxy-3β-acetate (5) ,α-amyrin acetate (6)and lupeol-9(11)en-3β-acetate (7)
respectively. All compounds were obtained from Crepis lignea for the first time.
Key words:Compositae;Crepis;Crepis lignea;triterpenoids
绿茎还阳参(Crepis lignea (Vant.)Babc.)为菊
科还阳参属(Crepis)多年生草本植物,别名马尾参,
铁扫把,细草,万丈深等,生于向阳山坡,在我国主要
分布四川,贵州,云南一带[1]。还阳参属植物约 200
种,我国约有 25 种[2]。该属植物中化学成分方面研
究较多的主要是芜菁还阳参(C. napifera)、还阳参
(C. turczaniowii)、C. bocconi 等,主要为三萜、倍半萜
和酚类化合物[3-6],其中倍半萜类化合物具有广泛的
生物活性。经文献调研,绿茎还阳参具有一定的药
用价值,为民间常用草药,润肺止咳,清热解毒,消食
理气,催乳。治支气管炎,肺炎,痈疽,小儿疳积,乳
汁不足,结膜炎;补虚,治体虚头晕无力[7]。然而有
关其化学成分,国内外未见任何文献报道,为了探寻
其中的有效成分,本研究对绿茎还阳参进行了系统
的次生代谢产物研究,分离鉴定了 7 个化合物,这些
化合物均为首次从该植物中分离得到。并对这些化
合物进行抑菌活性测试,结果均未显示明显的抑菌
活性。
1 实验材料
国产 XRC-1 型显微熔点仪;VG AutoSpec 3000
及 Finnigan MAT 90 质谱仪;Bruker AM-400、DRX-
500 和 AVANCE-600 核磁共振光谱仪(TMS为内标,
δ为 ppm,J 为 Hz)。柱色谱硅胶(200 ~ 300 目)和
薄层色谱硅胶 GF254均为青岛海洋集团有限公司生
产;MCI填充材料为 MCI-gel CHP-20P;凝胶为 Seph-
adex LH-20(Pharmacia Fine Chemical Co. Ltd) ;显色
剂为 15%的 H2SO4 /EtOH 溶液。绿茎还阳参采集
于云南省陆良县(2010 年 8 月) ,由中国科学院昆明
植物研究所龚洵研究员鉴定。
2 提取分离
绿茎还阳参干燥粗粉(500 g) ,用丙酮溶液浸提
(3 × 3 L) ,浓缩后得浸膏(30 g)。将其用丙酮溶解
后,硅胶拌样,经硅胶柱层析,氯仿 /丙酮梯度洗脱,
得到五个流份:Fr. 1(氯仿) ,Fr. 2(氯仿 /丙酮 9 ∶ 1) ,
Fr. 3(氯仿 /丙酮 8 ∶ 2) ,Fr. 4(氯仿 /丙酮 5 ∶ 5)和 Fr.
5(丙酮)。Fr. 1 反复硅胶柱层析(石油醚 /乙酸乙酯
8 ∶ 11) ,Sephadex LH-20 凝胶柱层析(丙酮)以及重
结晶得到化合物 1(10 mg)和 2(7 mg) ,Fr. 2 经 MCI
柱层析(70%甲醇 /水-甲醇)梯度洗脱,得到四个亚
流份(Fr. 2-1 到 Fr. 2-5) ,Fr. 2-1 依次经过 Sephadex
LH-20 凝胶柱层析(丙酮) ,硅胶柱层析(石油醚 /乙
酸乙酯 5 ∶ 1)得到化合物 3(2 mg)和 4(1. 5 mg) ,Fr.
2-3 依次经过 Sephadex LH-20 凝胶柱层析(丙酮) ,
反复硅胶柱层析(石油醚 /乙酸乙酯 20:1)得到化合
物 5(13 mg) ,Fr. 2-4 经过反复硅胶柱层析(石油醚 /
乙酸乙酯 70 ∶ 1)得到化合物 6(15 mg)和 7(12
mg)。
3 结构鉴定
化合物 1 白色簇状结晶(氯仿) ,mp. 204 ~
205 ℃,分子式为 C32 H52 O2,
1H NMR (400 MHz,
CDCl3)δ:4. 55 (1H,dd,J = 4. 6,11. 7 Hz,H-3) ,
2. 06 (3H,s,3-OAc) ,1. 05 (3H,s,H-23) ,1. 00
(3H,s,H-25) ,0. 99 (3H,d,J = 7. 0 Hz,H-29) ,
0. 98 (3H,s,H-26) ,0. 90 (3H,d,J = 6. 0 Hz,H-
30) ,0. 88 (3H,s,H-27) ,0. 87 (3H,s,H-28) ,0. 84
(3H,s,H-24)。13C NMR (100 MHz,CDCl3)δ:170. 2
(s,3-OAc) ,134. 5 (s,C-18) ,134. 0 (s,C-13) ,80. 9
(d,C-3) ,52. 3 (d,C-5) ,50. 5 (d,C-19) ,40. 9 (s,
C-17) ,38. 1 (s,C-4) ,37. 7 (t,C-22) ,37. 6 (s,C-
14) ,37. 4 (s,C-8) ,35. 9 (d,C-9) ,34. 7 (t,C-12) ,
33. 1 (t,C-22) ,31. 9 (d,C-20) ,31. 7 (s,C-10) ,
29. 6 (t,C-1) ,29. 0 (t,C-21) ,28. 2 (q,3-OAc) ,
27. 9 (q,C-23) ,27. 2 (t,C-15) ,25. 2 (t,C-16) ,
25. 1 (q,C-28) ,24. 2 (t,C-2) ,22. 4 (q,C-27) ,22. 2
(q,C-30) ,21. 3 (q,C-29) ,20. 5 (t,C-11) ,19. 9
(q,C-26) ,19. 0 (t,C-6) ,16. 6 (q,C-25) ,15. 6 (q,
C-24)。EI-MS m/z (%) :468 (52) [M]+,453
(34) ,410 (47) ,393 (51) ,289 (100) ,255 (32) ,
205 (62) ,189 (67) ,69 (96)。以上波谱数据与文
献[8]比较,可鉴定化合物为 3β-acetoxyurs-13(18)-
ene。
化合物 2 白色针状结晶(丙酮) ,mp. 201 ~
203 ℃,分子式为 C32 H52 O2,
1H NMR (400 MHz,
CDCl3)δ:4. 68 (1H,s,H-29b) ,4. 57 (1H,s,H-
29a) ,4. 47 (1H,dd,J = 5. 7,10. 6 Hz,H-3) ,2. 37
(1H,dt,J = 5. 8,11. 0 Hz,H-19) ,2. 04 (3H,s,
OAc) ,1. 91 (1H,dt,J = 10. 1,13. 5 Hz,H-2a) ,1. 68
(3H,s,H-30) ,1. 02 (3H,s,H-25) ,0. 93 (3H,s,H-
28) ,0. 85 (3H,s,H-23) ,0. 84 (3H,s,H-24) ,0. 83
(3H,s,H-26) ,0. 78 (3H,s,H-27)。13 C NMR (100
MHz,CDCl3)δ:171. 0 (s,3-OAc) ,150. 9 (s,C-20) ,
109. 3 (t,C-29) ,80. 9 (d,C-3) ,55. 3 (d,C-5) ,50. 3
(d,C-9) ,48. 2 (d,C-18) ,48. 0 (d,C-19) ,41. 2 (s,
C-17) ,41. 1 (s,C-14) ,40. 3 (s,C-4) ,40. 0 (t,C-
16) ,38. 3 (t,C-7) ,38. 0 (d,C-13) ,37. 8 (s,C-10) ,
35. 8 (s,C-8) ,35. 5 (t,C-21) ,34. 2 (t,C-15) ,29. 8
(t,C-12) ,27. 9 (q,3-OAc) ,27. 4 (t,C-2) ,25. 0 (t,
C-11) ,23. 7 (t,C-2) ,21. 3 (q,C-23) ,20. 9 (t,C-
6) ,19. 5 (q,C-30) ,18. 2 (t,C-1) ,18. 0 (q,C-28) ,
16. 5 (q,C-24) ,16. 1 (q,C-25) ,15. 9 (q,C-26) ,
14. 5 (q,C-27)。以上波谱数据与文献[9]比较,鉴定
化合物为 lupeol acetate。
化合物 3 白色粉末,分子式为 C10 H10 O3,
1H
NMR (600 MHz,CDCl3)δ:9. 65 (1H,d,J = 7. 8 Hz,
H-9) ,7. 40 (1H,d,J = 15. 8 Hz,H-7) ,7. 13 (1H,
dd,J = 1. 8,8. 2 Hz,H-6) ,7. 07 (1H,d,J = 1. 8 Hz,
H-2) ,6. 96 (1H,d,J = 8. 2 Hz,H-5) ,6. 60 (1H,
dd,J = 7. 8,15. 8 Hz,H-8) ,5. 99 (1H,s,4-OH) ,
3. 95 (3H,s,3-OAc)。13 C NMR (150 MHz,CDCl3)
δ:193. 8 (d,C-9) ,153. 2 (d,C-7) ,148. 9 (s,C-4) ,
146. 9 (s,C-3) ,126. 4 (s,C-1) ,126. 4 (d,C-8) ,
124. 1 (d,C-6) ,114. 9 (d,C-5) ,109. 3 (d,C-2) ,
56. 0 (q,3-OAc)。以上波谱数据与文献[10]比较,鉴
定化合物为 4-hydroxy 3-methoxycinnamaldehyde。
化合物 4 白色粉末,分子式为 C7H10 O4,
1H
NMR (600 MHz,CDCl3)δ:6. 88 (1H,dd,J = 2. 1,
7. 3 Hz,H-5) ,3. 37 (1H,d,J = 7. 4 Hz,H-3) ,1. 92
(3H,dd,J = 1. 1,7. 4 Hz,H-6) ,1. 45 (3H,d,J = 7. 5
Hz,H-7)。13C NMR (150 MHz,CDCl3)δ:177. 9 (s,
C-4) ,169. 0 (s,C-1) ,135. 4 (d,C-5) ,132. 6 (s,C-
2) ,38. 5 (d,C-3) ,15. 6 (q,C-7) ,14. 8 (q,C-6)。
结合 2D NMR数据,并与文献[11]比较得出化合物为
(Z)-2-ethylidene-3-methylsuccinic acid。
化合物 5 白色固体,分子式为 C33 H54 O3,
1H
NMR (500 MHz,CDCl3)δ:5. 46 (1H,d,J = 3. 6 Hz,
H-12) ,4. 45 (1H,dd,J = 4. 8,11. 7 Hz,H-3) ,3. 19
(3H,s,11-OMe) ,1. 99 (3H,s,3-OAc) ,1. 24 (3H,
s,H-27) ,1. 09 (3H,s,H-25) ,1. 03 (3H,s,H-26) ,
0. 91 (3H,s,H-29) ,0. 89 (3H,s,H-30) ,0. 89 (3H,
s,H-24) ,0. 88 (3H,s,H-23) ,0. 86 (3H,s,H-28)。
13C NMR (125 MHz,CDCl3)δ:171. 1 (s,3-OAc) ,
150. 4 (s,C-13) ,123. 3 (d,C-12) ,81. 4 (d,C-3) ,
267 天然产物研究与开发 Vol. 24
76. 6 (d,C-11) ,56. 4 (d,C-5) ,54. 2 (q,11-OMe) ,
53. 0 (d,C-9) ,48. 1 (d,C-18) ,47. 8 (t,C-19) ,42. 5
(s,C-8) ,41. 6 (s,C-14) ,38. 2 (C-4) ,40. 7 (t,C-
1) ,38. 1 (t,C-22) ,38. 0 (s,C-10) ,35. 7 (t,C-21) ,
34. 7 (t,C-7) ,32. 1 (s,C-17) ,31. 0 (s,C-20) ,33. 9
(q,C-29) ,21. 5 (q,3-OAc) ,24. 4 (q,C-30) ,28. 8
(q,C-28) ,27. 3 (q,C-27) ,17. 8 (q,C-26) ,17. 5
(q,C-25) ,17. 4 (q,C-24) ,28. 8 (q,C-23) ,27. 9
(t,C-16) ,27. 4 (t,C-15) ,19. 4 (t,C-6) ,23. 9 (t,C-
2)。EI-MS m/z (%) :498 (95) [M]+,482 (32) ,
466 (51) ,451 (21) ,407 (25) ,293 (29) ,273
(49) ,248 (100) ,232 (47)。以上波谱数据与文
献[12]比较,故鉴定化合物为 olean-12-ene-11α-me-
thoxy-3β-acetate。
化合物 6 白色簇状结晶(丙酮) ,mp. 231 ~
232 ℃,分子式为 C32 H52 O2,
1H NMR (400 MHz,
CDCl3)δ:5. 70 (1H,t,J = 4. 8 Hz,H-12) ,4. 48
(1H,dd,J = 4. 1,11. 4 Hz,H-3) ,2. 04 (3H,s,3-
OAc) ,1. 05 (3H,s,H-23) ,1. 03 (3H,d,J = 6. 5 Hz,
H-29) ,1. 02 (3H,s,H-25) ,0. 97 (3H,s,H-26) ,
0. 95 (3H,s,H-27) ,0. 93 (3H,d,J = 7. 0 Hz,H-
30) ,0. 90 (3H,s,H-28) ,0. 87 (3H,s,H-24)。13 C
NMR (100 MHz,CDCl3)δ:170. 8 (s,3-OAc) ,142. 9
(s,C-13) ,124. 8 (d,C-12) ,80. 4 (d,C-3) ,53. 1
(d,C-18) ,52. 0 (d,C-5) ,39. 9 (d,C-9) ,34. 9 (d,
C-19) ,31. 9 (d,C-20) ,39. 1 (s,C-14) ,38. 8 (s,C-
8) ,37. 6 (s,C-4) ,37. 5 (t,C-22) ,36. 9 (t,C-21) ,
35. 8 (s,C-10) ,35. 7 (t,C-7) ,35. 0 (s,C-17) ,31. 2
(t,C-15) ,29. 1 (t,C-16) ,27. 9 (q,3-OAc) ,27. 8
(q,C-23) ,25. 1 (q,C-28) ,24. 1 (t,C-1) ,24. 1 (t,
C-11) ,23. 7 (q,C-27) ,22. 5 (t,C-6) ,22. 4 (q,C-
30) ,22. 0 (t,C-2) ,21. 3 (q,C-24) ,17. 9 (q,C-
29) ,17. 8 (q,C-26) ,17. 2 (q,C-25)。EI-MS m/z
(%) :468 (8) [M]+,453 (9) ,424 (12) ,423
(49) ,422 (100) ,407 (51) ,394 (25) ,393 (28) ,
379 (30)。以上波谱数据与文献[13,14]比较,故鉴定
化合物为 α-amyrin acetate。
化合物 7 白色针状结晶(丙酮) ,mp. 105 ~
107 ℃,分子式 C32 H52 O2,
1H NMR (400 MHz,
CDCl3)δ:5. 54 (1H,m,H-11) ,4. 51 (1H,dd,J = 5.
8,10. 4 Hz,H-3) ,2. 05 (3H,s,3-OAc) ,1. 08 (3H,
d,J = 5. 9 Hz,H-30) ,1. 01 (3H,s,H-25) ,0. 92
(3H,s,H-28) ,0. 90 (3H,d,J = 6. 4 Hz,H-29) ,0. 85
(3H,s,H-23) ,0. 84 (3H,s,H-24) ,0. 83 (3H,s,H-
26) ,0. 78 (3H,s,H-27)。13 C NMR (100 MHz,
CDCl3)δ:170. 8 (s,3-OAc) ,157. 0 (s,C-9) ,118. 9
(d,C-11) ,80. 6 (d,C-3) ,58. 7 (d,C-5) ,58. 2 (d,
C-13) ,54. 5 (d,C-18) ,53. 7 (d,C-19) ,41. 1 (t,C-
12) ,41. 0 (s,C-14) ,39. 8 (s,C-4) ,39. 6 (t,C-16) ,
38. 3 (t,C-7) ,37. 8 (s,C-10) ,35. 8 (s,C-8) ,35. 5
(t,C-21) ,35. 1 (d,C-20) ,34. 9 (t,C-1) ,34. 1 (t,
C-15) ,29. 8 (t,C-12) ,27. 9 (q,3-OAc) ,27. 4 (t,C-
2) ,25. 0 (t,C-11) ,23. 2 (t,C-2) ,22. 2 (q,C-23) ,
22. 1 (q,C-30) ,21. 2 (q,C-28) ,19. 5 (q,C-24) ,
19. 4 (t,C-6) ,18. 9 (q,C-25) ,16. 8 (q,C-26) ,16. 6
(q,C-27)。以上波谱数据与文献[15]比较,故鉴定化
合物为 lupeol-9(11)en-3β-acetate。
4 结论
从绿茎还阳参中分离得到了 7 个化合物,包括
5 个三萜、1 个酚类和 1 个小分子化合物。目前从绿
茎还阳参中分离得到的主要次生代谢产物为三萜类
化合物,而同属其它植物(如:芜菁还阳参、还阳参、
C. bocconi)中主要次生代谢产物为倍半萜类化合
物。因此,从化学角度上该属植物的同源性还有待
进一步研究。
参考文献
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(下转第 831 页)
367Vol. 24 华 娟等:绿茎还阳参化学成分的研究
肪酸等活性物质发挥的作用,使血脂代谢达到平衡。
目前,心脑血管疾病是世界最大的难题,其发病
率、死亡率、用药额均占首位[1]。心脑血管病的发
生主要原因是血管壁硬化,而血管壁硬化的原因是
脂物质的沉积。实验证明,林蛙卵酶解液可以明显
改善去卵巢大鼠的高血脂症状,有效的抑制肝细胞
受损,并且可以降低大鼠的脂肪系数和肝脏系数,这
说明林蛙卵可以很好的预防心脑血管疾病。
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138Vol. 24 芦红艳等:林蛙卵对去卵巢大鼠血清生化指标的影响