2014, Vol. 45
引用本文 | doi: 10.7501/j.issn.0253-2670.2014.15.006 |
兔儿风属Ainsliaea DC. 隶属于菊科（Compositae）帚菊木族（Mutisieae Cass.），全世界约有70种，分布于亚洲东南部。我国有44种4个变种，除1种产于东北外，其余均产于长江流域及其以南各省[1]。到目前为止，从本属植物分到的化合物主要有倍半萜内酯及其苷、三萜、甾体和黄酮等[2]。宽叶兔儿风Ainsliaea latifolia (D. Don) Sch. -Bip. 为菊科兔儿风属植物，分布于我国西藏、云南、四川、贵州、广西及海南等地，民间主要用于治疗风寒咳嗽、肠炎、痢疾、跌打损伤等[3]。目前尚未有关于该植物化学成分及生物活性方面的研究报道。为了从中寻找更多结构新颖的生物活性成分，本实验对宽叶兔儿风的化学成分进行了研究，从其全草80%乙醇提取物中得到了13个化合物，分别鉴定为木栓酮（friedelin，1）、蒲公英萜醇乙酸酯（taraxeryl acetate，2）、3β-hydroxy-11α,12α-epoxy-friedoolean- 14-ene（3）、careborin（4）、cis-careborin（5）、3α-E-feruloyltaraxerol（6）、3α-Z-feruloyltaraxerol（7）、3-oxo-11α-methoxyolean-12-ene（8）、diaspanolide A（9）、diaspanolide B（10）、ainsliaolide A（11）、豆甾醇（stigmasterol，12）、β-谷甾醇（β-sitosterol，13）。化合物1～13均为首次从该植物中分离得到，其中包括8个三萜类（1～8），3个倍半萜类（9～11），2个甾体类化合物（12～13）。部分结构见图 1。
 | 图 1 化合物2～11的结构 Fig. 1 Structures of compounds 2－11 |
Bruker DRX—500型核磁共振谱仪（德国Bruker公司）；Agilent LC/MSD Trap XCT质谱仪（美国Agilent公司）；SK5200H型超声发生器（上海科导超声仪器有限公司）；Sephadex LH-20（Pharmacia公司）；反相硅胶C18（Merck公司）；薄层色谱硅胶和HSGF254硅胶预制板（烟台江友硅胶开发有限公司）；提取用乙醇为工业级，质谱用试剂为色谱级，其余试剂均为分析纯。
宽叶兔儿风全草于2013年9月采自贵州贵阳，经贵阳医学院生药教研室龙庆德教授鉴定为宽叶兔儿风Ainsliaea latifolia (D. Don) Sch. -Bip.，植物标本（20130905）现保存在第二军医大学药学院天然药化教研室。
2 提取与分离宽叶兔儿风全草（15 kg）粉碎后用80%乙醇浸泡4次，每次48 h，提取液回流蒸干后得80%乙醇提取物2 kg。依次用石油醚、氯仿、醋酸乙酯、甲醇进行固相萃取，取氯仿部位（105 g）进行硅胶柱色谱，石油醚-醋酸乙酯（100∶1→50∶1→30∶1→10∶1→5∶1→0∶1）梯度洗脱，得到7个流分（Fr. 1～7）。其中Fr. 2（21 g）经硅胶柱分离，以石油醚- 丙酮（50∶1→0∶1）梯度洗脱，再经Sephadex LH-20 柱色谱与制备薄层分离纯化得到化合物1（1.6 g）、2（24.5 mg）、12（75.6 mg）、13（43.8 mg）。Fr. 3（17 g）用硅胶柱分离，以石油醚-醋酸乙酯（50∶1→0∶1）进行梯度洗脱，再经Sephadex LH-20柱色谱与制备薄层分离纯化得到化合物9（43.6 mg）、10（350 mg）、11（11.6 mg）。Fr. 5（13 g）用开放硅胶柱分离，以石油醚-醋酸乙酯（50∶1→0∶1）进行梯度洗脱，再经Sephadex LH-20柱色谱、制备薄层分离纯化得到化合物3（2.3 mg）、8（2.4 mg）。Fr. 6（26 g）用ODS柱色谱分离，以甲醇-水进行梯度洗脱，再经Sephadex LH-20柱色谱、制备薄层、高压液相制备分离纯化得到化合物4（6.6 mg）、5（6.0 mg）、6（15 mg）、7（44 mg）。
3 结构鉴定化合物1：白色固体，ESI-MS m/z: 449 [M＋Na]+,425 [M－H]-，分子式为C30H50O。1H-NMR (500 MHz,CDCl3) δ: 2.39 (1H,m,H-2),2.26 (2H,m,H-2,4),1.95 (1H,m,H-1),1.75 (1H,m,H-6),1.66 (1H,m,H-1),1.17 (3H,s,H-28),1.04 (3H,s,H-27),1.00 (3H,s,H-26),0.99 (3H,s,H-27),0.94 (3H,s,H-29),0.87 (3H,d,J = 6.6 Hz,H-23),0.86 (3H,s,H-25),0.71 (3H,s,H-24)；13C-NMR (125 MHz,CDCl3) δ: 22.2 (C-1),41.5 (C-2),213.1 (C-3),58.2 (C-4),42.1 (C-5),41.3 (C-6),18.2 (C-7),53.1 (C-8),37.4 (C-9),59.4 (C-10),35.6 (C-11),30.5 (C-12),39.7 (C-13),38.3 (C-14),32.4 (C-15),36.0 (C-16),30.0 (C-17),42.8 (C-18),35.3 (C-19),28.1 (C-20),32.7 (C-21),39.2 (C-22),6.8 (C-23),14.6 (C-24),17.9 (C-25),20.2 (C-26),18.6 (C-27),32.1 (C-28),35.0 (C-29),31.8 (C-30)。以上数据与文献报道一致[4]，故鉴定化合物1为木栓酮。
化合物2：白色固体，ESI-MS m/z: 491 [M＋Na]+,467 [M－H]-，分子式为C32H52O2。1H-NMR (500 MHz,CDCl3) δ: 5.52 (1H,dd,J = 8.2,3.2 Hz,H-15),4.45 (1H,dd,J = 10.6,5.6 Hz,H-3),2.04 (3H,s,H-2′),1.09 (3H,s,H-26),0.95 (6H,s,H-24,29),0.91 (6H,s,H-30,27),0.87 (3H,s,H-23),0.86 (3H,s,H-25),0.82 (3H,s,H-28)；13C-NMR (125 MHz,CDCl3) δ: 37.9 (C-1),25.9 (C-2),81.0 (C-3),37.7 (C-4),55.6 (C-5),18.7 (C-6),33.1 (C-7),39.0 (C-8),49.2 (C-9),37.5 (C-10),17.5 (C-11),35.8 (C-12),36.6 (C-13),158.0 (C-14),116.9 (C-15),33.3 (C-16),35.1 (C-17),48.7 (C-18),41.2 (C-19),29.7 (C-20),33.7 (C-21),37.4 (C-22),28.8 (C-23),16.6 (C-24),15.5 (C-25),28.0 (C-26),29.8 (C-27),29.9 (C-28),23.4 (C-29),21.3 (C-30),171.0 (C-1′),21.3 (C-2′)。以上数据与文献报道一致[5]，故鉴定化合物2为蒲公英萜醇乙酸酯。
化合物3：白色固体；ESI-MS m/z: 463 [M＋Na]+,439 [M－H]-；分子式为C30H48O2。1H-NMR (500 MHz,CDCl3) δ: 5.55 (1H,dd,J = 8.1,3.0 Hz,H-15),4.12 (1H,d,J = 7.1 Hz,H-3),3.25 (1H,m,H-11),3.12 (1H,t,J = 5.1 Hz,H-12),2.81 (1H,d,J = 4.6 Hz,H-9),1.08 (6H,s,H-25,26),1.01 (3H,s,H-24),0.99 (3H,s,H-29),0.97 (3H,s,H-27),0.86 (3H,s,H-23),0.82 (3H,s,H-28,30)；13C-NMR (125 MHz,CDCl3) δ: 38.2 (C-1),26.8 (C-2),79.0 (C-3),38.6 (C-4),54.6 (C-5),18.9 (C-6),33.1 (C-7),38.9 (C-8),52.0 (C-9),37.5 (C-10),53.6 (C-11),58.3 (C-12),36.6 (C-13),157.1 (C-14),118.9 (C-15),35.2 (C-16),35.4 (C-17),48.1 (C-18),40.3 (C-19),28.7 (C-20),36.5 (C-21),38.2 (C-22),27.9 (C-23),16.9 (C-24),15.4 (C-25),27.0 (C-26),30.2 (C-27),29.9 (C-28),33.6 (C-29),19.5 (C-30)。以上数据与文献报道一致[6]，故鉴定化合物3为3β-hydroxy-11α,12α- epoxy-friedoolean-14-ene。
化合物4：白色固体，ESI-MS m/z: 595 [M＋Na]+,571 [M－H]-，分子式为C39H56O3。1H-NMR (500 MHz,CDCl3) δ: 7.60 (1H,d,J = 15.9 Hz,H-3′),7.43 (2H,d,J = 8.5 Hz,H-6′,8′),6.84 (2H,d,J = 8.5 Hz,H-5′,9′),6.30 (1H,d,J = 15.9 Hz,H-2′),5.54 (1H,dd,J = 8.1,3.1 Hz,H-15),4.60 (1H,dd,J = 10.9,5.4 Hz,H-3),1.10 (3H,s,H-26),0.98 (3H,s,H-25),0.95 (6H,s,H-24,29),0.91 (6H,s,H-30,27),0.90 (3H,s,H-23),0.82 (3H,s,H-28)；13C-NMR (125 MHz,CDCl3) δ: 37.5 (C-1),23.6 (C-2),81.0 (C-3),39.0 (C-4),55.6 (C-5),18.7 (C-6),33.1 (C-7),37.7 (C-8),49.2 (C-9),37.4 (C-10),17.5 (C-11),36.6 (C-12),37.9 (C-13),158.0 (C-14),116.9 (C-15),33.7 (C-16),35.8 (C-17),48.7 (C-18),41.2 (C-19),28.8 (C-20),35.1 (C-21),37.9 (C-22),28.0 (C-23),16.8 (C-24),15.5 (C-25),25.9 (C-26),29.9 (C-27),29.8 (C-28),33.3 (C-29),21.3 (C-30),167.4 (C-1′),116.2 (C-2′),144.0 (C-3′),127.3 (C-4′),129.9 (C-5′,9′),115.8 (C-6′,8′),157.6 (C-7′)。以上数据与文献报道一致[7]，故鉴定化合物4为careborin。
化合物5：白色固体，ESI-MS m/z: 595 [M＋Na]+,571 [M－H]-，分子式为C39H56O3。1H-NMR (500 MHz,CDCl3) δ: 7.61 (2H,d,J = 7.4 Hz,H-6′,8′),6.84 (1H,d,J = 12.7 Hz,H-3′),6.77 (2H,d,J = 8.6 Hz,H-5′,9′),5.84 (1H,dd,J = 8.1,12.6 Hz,H-2′),5.54 (1H,dd,J = 8.1,3.2 Hz,H-15),4.52 (1H,dd,J = 11.0,4.9 Hz,H-3),1.09 (3H,s,H-26),0.96 (6H,s,H-24,29),0.91 (6H,s,H-30,27),0.87 (3H,s,H-25),0.85 (3H,s,H-23),0.82 (3H,s,H-28)；13C-NMR (125 MHz,CDCl3) δ: 37.5 (C-1),23.4 (C-2),81.2 (C-3),39.0 (C-4),55.6 (C-5),18.7 (C-6),33.1 (C-7),37.7 (C-8),49.1 (C-9),37.4 (C-10),17.5 (C-11),36.6 (C-12),37.9 (C-13),158.0 (C-14),116.9 (C-15),33.7 (C-16),35.8 (C-17),48.8 (C-18),41.2 (C-19),28.8 (C-20),35.1 (C-21),37.9 (C-22),28.0 (C-23),16.6 (C-24),15.5 (C-25),25.9 (C-26),29.9 (C-27),29.8 (C-28),33.3 (C-29),21.3 (C-30),166.7 (C-1′),116.9 (C-2′),143.4 (C-3′),127.4 (C-4′),132.2 (C-5′,9′),115.1 (C-6′,8′),156.8 (C-7′)。以上数据与文献报道一致[8]，故鉴定化合物5为cis-careborin。
化合物6：白色固体，ESI-MS m/z: 625 [M＋Na]+,601 [M－H]-，分子式为C40H58O4。1H-NMR (500 MHz,CDCl3) δ: 7.59 (1H,d,J = 15.9 Hz,H-3′),7.08 (1H,dd,J = 8.0,1.5 Hz,H-9′),7.06 (1H,d,J = 1.5 Hz,H-5′),6.91 (1H,d,J = 8.1 Hz,H-8′),6.29 (1H,d,J = 15.9 Hz,H-2′),5.57 (1H,dd,J = 8.1,3.2 Hz,H-15),4.52 (1H,dd,J = 11.0,4.9 Hz,H-3),3.92 (3H,s,H-10′),1.10 (3H,s,H-26),0.98 (3H,s,H-25),0.95 (6H,s,H-24,29),0.91 (6H,s,H-30,27),0.90 (3H,s,H-23),0.82 (3H,s,H-28)；13C-NMR (125 MHz,CDCl3) δ: 37.5 (C-1),23.5 (C-2),80.7 (C-3),39.0 (C-4),55.7 (C-5),18.7 (C-6),33.1 (C-7),37.7 (C-8),49.1 (C-9),37.4 (C-10),17.5 (C-11),36.6 (C-12),37.9 (C-13),158.0 (C-14),116.9 (C-15),33.7 (C-16),35.8 (C-17),48.8 (C-18),41.2 (C-19),28.8 (C-20),35.1 (C-21),37.9 (C-22),28.0 (C-23),16.6 (C-24),15.5 (C-25),25.9 (C-26),29.9 (C-27),29.8 (C-28),33.3 (C-29),21.3 (C-30),167.1 (C-1′),116.9 (C-2′),143.3 (C-3′),127.1 (C-4′),109.2 (C-5′),146.7 (C-6′),147.8 (C-7′),114.6 (C-8′),123.0 (C-9′),56.0 (C-10′)。以上数据与文献报道一致[9]，故鉴定化合物6为3α-E- feruloyltaraxerol。
化合物7：白色固体，ESI-MS m/z: 625 [M＋Na]+,601 [M－H]-，分子式为C40H58O3。1H-NMR (500 MHz,CDCl3) δ: 7.78 (1H,d,J = 1.8 Hz,H-5′),7.10 (1H,dd,J = 8.2,1.7 Hz,H-9′),6.87 (1H,d,J = 8.2 Hz,H-8′),6.77 (1H,d,J = 13 Hz,H-3′),5.82 (1H,d,J = 14.7 Hz,H-2′),5.54 (1H,dd,J = 8.1,3.2 Hz,H-15),4.52 (1H,dd,J = 11.0,4.9 Hz,H-3),3.92 (3H,s,H-10′),1.10 (3H,s,H-26),0.98 (3H,s,H-25),0.95 (6H,s,H-24,29),0.91 (6H,s,H-30,27),0.90 (3H,s,H-23),0.82 (3H,s,H-28)；13C-NMR (125 MHz,CDCl3) δ: 37.5 (C-1),23.5 (C-2),80.7 (C-3),39.0 (C-4),55.7 (C-5),18.7 (C-6),33.1 (C-7),37.7 (C-8),49.1 (C-9),37.4 (C-10),17.5 (C-11),36.6 (C-12),37.9 (C-13),158.0 (C-14),116.9 (C-15),33.7 (C-16),35.8 (C-17),48.8 (C-18),41.2 (C-19),28.8 (C-20),35.1 (C-21),37.9 (C-22),28.0 (C-23),16.6 (C-24),15.5 (C-25),25.9 (C-26),29.9 (C-27),29.8 (C-28),33.3 (C-29),21.3 (C-30),166.5 (C-1′),116.9 (C-2′),143.3 (C-3′),127.3 (C-4′),112.8 (C-5′),145.9 (C-6′),146.9 (C-7′),113.8 (C-8′),125.5 (C-9′),56.0 (C-10′)。以上数据与文献报道一致[9]，故鉴定化合物7为3α-Z- feruloyltaraxerol。
化合物8：无色油状物，ESI-MS m/z: 477 [M＋Na]+,453 [M－H]-，分子式为C31H50O2。1H-NMR (500 MHz,CDCl3) δ: 5.36 (1H,d,J = 3.1 Hz,H-12),3.93 (1H,dd,J = 9.4,3.1 Hz,H-11),3.24 (3H,s,H-1′),1.22 (3H,s,H-27),1.15 (3H,s,H-25),1.11 (3H,s,H-23),1.07 (3H,s,H-24),1.06 (3H,s,H-26),0.90 (3H,s,H-30),0.89 (3H,s,H-29),0.84 (3H,s,H-28)；13C-NMR (125 MHz,CDCl3) δ: 40.3 (C-1),34.4 (C-2),218.1 (C-3),47.7 (C-4),55.5 (C-5),19.7 (C-6),32.9 (C-7),42.9 (C-8),50.3 (C-9),37.7 (C-10),76.3 (C-11),121.6 (C-12),149.3 (C-13),42.0 (C-14),26.2 (C-15),26.8 (C-16),32.4 (C-17),47.2 (C-18),46.4 (C-19),31.1 (C-20),34.7 (C-21),36.9 (C-22),26.7 (C-23),21.5 (C-24),16.4 (C-25),18.1 (C-26),25.1 (C-27),28.5 (C-28),33.2 (C-29),23.6 (C-30),53.7 (C-1′)。以上数据与文献报道一致[10]，故鉴定化合物8为3-oxo-11α-methoxyolean-12-ene。
化合物9：黄色油状物，ESI-MS m/z: 355 [M＋Na]+,331 [M－H]-，分子式为C20H28O4。1H-NMR (500 MHz,CDCl3) δ: 5.54 (1H,m,H-3),5.39 (1H,t,J = 2.0 Hz,H-15),5.25 (1H,t,J = 2.0 Hz,H-15),4.89 (2H,d,J = 9.0 Hz,H-14),4.08 (1H,t,J = 9.8 Hz,H-6),2.89 (1H,m,H-1),2.83 (1H,m,H-5),2.67 (1H,m,H-7),2.46 (3H,m,H-2,9),1.15 (3H,d,J = 7.8 Hz,H-13),0.96 (6H,d,J = 6.6 Hz,H-4′,5′)；13C-NMR (125 MHz,CDCl3) δ: 43.7 (C-1),36.2 (C-2),74.4 (C-3),148.9 (C-4),50.1 (C-5),83.7 (C-6),45.7 (C-7),28.7 (C-8),36.2 (C-9),148.4 (C-10),39.2 (C-11),179.6 (C-12),11.4 (C-13),113.4 (C-14),113.2 (C-15),172.8 (C-1′),43.6 (C-2′),25.7 (C-3′),22.4 (C-4′),22.4 (C-5′)。以上数据与文献报道一致[11]，故鉴定化合物9为diaspanolide A。
化合物10：黄色油状物，ESI-MS m/z: 353 [M＋Na]+,329 [M－H]-，分子式为C20H26O4。1H-NMR (500 MHz,CDCl3) δ: 6.21 (1H,d,J = 3.5 Hz,H-13),5.56 (1H,m,H-3),5.49 (1H,d,J = 3.1 Hz,H-13),5.45 (1H,t,J = 2.0 Hz,H-15),5.27 (1H,t,J = 2.1 Hz,H-15),4.97 (2H,d,J = 6.4 Hz,H-14),4.06 (1H,dd,J = 16.9,7.6 Hz,H-6),2.94 (1H,m,H-1),2.85 (2H,m,H-5,7),2.46 (2H,m,H-9),1.78 (1H,m,H-2),0.96 (6H,d,J = 6.6 Hz,H-4′,5′)；13C-NMR (125 MHz,CDCl3) δ: 44.6 (C-1),34.6 (C-2),74.3 (C-3),147.8 (C-4),50.2 (C-5),83.9 (C-6),45.2 (C-7),30.6 (C-8),36.6 (C-9),148.2 (C-10),139.5 (C-11),170.0 (C-12),120.3 (C-13),114.3 (C-14),113.4 (C-15),172.8 (C-1′),43.6 (C-2′),25.8 (C-3′),22.4 (C-4′),22.4 (C-5′)。以上数据与文献报道一致[12]，故鉴定化合物10为diaspanolide B。
化合物11：黄色油状物，ESI-MS m/z: 351 [M＋Na]+,327 [M－H]-，分子式为C20H24O4。1H-NMR (500 MHz,CDCl3) δ: 6.22 (1H,d,J = 3.5 Hz,H-13),5.72 (1H,m,H-2′),5.59 (1H,m,H-3),5.49 (1H,d,J = 3.1 Hz,H-13),5.47 (1H,t,J = 2.0 Hz,H-15),5.30 (1H,t,J = 2.0 Hz,H-15),4.97 (2H,d,J = 12.7 Hz,H-14),4.07 (1H,dd,J = 16.9,7.6 Hz,H-6),2.94 (1H,m,H-1),2.85 (2H,m,H-5,7),2.46 (2H,m,H-9),2.19 (3H,d,J = 0.9 Hz,H-5′),1.91 (3H,d,J = 1.0 Hz,H-4′),1.78 (1H,m,H-2),0.96 (6H,d,J = 6.6 Hz,H-4′,5′)；13C-NMR (125 MHz,CDCl3) δ: 44.7 (C-1),34.6 (C-2),73.7 (C-3),147.9 (C-4),50.3 (C-5),84.0 (C-6),45.2 (C-7),30.7 (C-8),36.8 (C-9),148.4 (C-10),139.6 (C-11),170.0 (C-12),120.3 (C-13),114.4 (C-14),113.2 (C-15),166.3 (C-1′),115.9 (C-2′),157.4 (C-3′),20.3 (C-4′),27.4 (C-5′)。以上数据与文献报道一致[13]，故鉴定化合物11为ainsliaolide A。
化合物12：白色固体，ESI-MS m/z: 435 [M＋Na]+,411 [M－H]-，分子式为C29H48O。1H-NMR (500 MHz,CDCl3) δ: 5.36 (1H,d,J = 5.2 Hz,H-6),5.14 (1H,m,H-22),5.01 (1H,m,H-23),3.53 (1H,m,H-3),0.82 (3H,t,J = 7.2 Hz,H-29),0.71 (3H,s,H-18)；13C-NMR (125 MHz,CDCl3) δ: 37.2 (C-1),31.7 (C-2),71.8 (C-3),42.3 (C-4),140.7 (C-5),121.7 (C-6),31.9 (C-7),31.9 (C-8),50.2 (C-9),36.5 (C-10),21.1 (C-11),39.7 (C-12),42.2 (C-13),55.9 (C-14),24.4 (C-15),28.9 (C-16),56.9 (C-17),12.0 (C-18),19.4 (C-19),40.5 (C-20),21.2 (C-21),138.3 (C-22),129.3 (C-23),51.2 (C-24),31.9 (C-25),19.0 (C-26),21.1 (C-27),25.4 (C-28),12.2 (C-29)。以上数据与文献报道一致[14]，故鉴定化合物12为豆甾醇。
化合物13：白色固体，ESI-MS m/z: 437 [M＋Na]+,413 [M－H]-，分子式为C29H50O。1H-NMR (500 MHz,CDCl3) δ: 5.36 (1H,m,H-6),3.53 (1H,m,H-3),1.02 (3H,s,H-19),0.92 (3H,d,J = 6.6 Hz,H-21)；13C-NMR (125 MHz,CDCl3) δ: 37.2 (C-1),31.7 (C-2),71.8 (C-3),42.3 (C-4),140.8 (C-5),121.7 (C-6),31.9 (C-7),31.9 (C-8),50.1 (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),56.0 (C-17),11.8 (C-18),19.4 (C-19),36.1 (C-20),18.8 (C-21),33.9 (C-22),26.1 (C-23),45.8 (C-24),29.1 (C-25),19.8 (C-26),19.0 (C-27),23.1 (C-28),12.0 (C-29)。以上数据与文献报道一致[15]，故鉴定化合物13为β-谷甾醇。
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