2. 苏州大学药学院, 江苏 苏州 215123 ;
3. 创新药物与高效节能降耗制药设备国家重点实验室, 江西 南昌 330006
2. College of Pharmaceutical Science, Soochow University, Suzhou 215123, China ;
3. State Key Laboratory of Innovative Drug and Efficient Energy-Saving Pharmaceutical Equipment, Nanchang 330006, China
平卧菊三七Gynura procumbens (Lour.) Merr为菊科(Compositae)千里光族(Senecioneae Cass.)菊三七属Gynura Cass. 植物,又名蛇接骨、续命草、神仙草,味辛、微苦,性凉,为多年生草本药食两用植物,生于林间溪旁的坡地砂质土上,分布于东南亚及我国南部及西南部地区[1]。平卧菊三七具有良好的止血、镇痛、抗炎、抗疟、抗肿瘤、降血糖等药理活性,主要用于治疗跌打损伤、风湿关节痛和痛风[2-3]。文献报道其主要含有黄酮、脂肪酸、多酚和类固醇等成分[4]。为进一步研究其活性成分,本实验对平卧菊三七的化学成分进行研究,分离得到16个化合物,分别鉴定为槲皮素(quercetin,1)、芹菜素(apigenin,2)、木犀草素(luteolin,3)、山柰酚(kaempferol,4)、黄芪苷(astragaline,5)、山柰酚-5-O-(6″-O-乙酰基)-β-D-吡喃葡萄糖苷[kaempferol-5-O-(6″-O-acetyl)-β-D-glucopyranoside,6]、7-甲醚黄芩素(negletein,7)、4-甲氧基肉桂酸(4-methoxycinnamic acid,8)、苄基葡萄糖苷(benzyl- O-β-D-glucopyranoside,9)、2-苯乙基-O-β-D-吡喃葡萄糖苷(2-phenylethyl-O-β-D-glucopyranoside,10)、3,5-二咖啡酰基奎宁酸甲酯(3,5-dicaffeoyl- quinic acid methyl ester,11)、3,5-二咖啡酰基奎宁酸乙酯(3,5-dicaffeoylquinic acid ethyl ester,12)、3,4-二咖啡酰基奎宁酸甲酯(3,4-dicaffeoylquinic acid methyl ester,13)、4,5-二咖啡酰基奎宁酸甲酯(4,5-dicaffeoylquinic acid methyl ester,14)、原儿茶酸(protocatechuic acid,15)、丁香酚苷(eugenol glucoside,16)。其中,化合物7、8、12、14和16为首次从菊三七属植物中分离得到,化合物3、6、9~11和13为首次从该植物中分离得到。
1 仪器与材料Bruker AVANCE III 600核磁共振仪(德国布鲁克公司);QTrap 4500+型质谱仪(加拿大AB SCIEX);半制备高效液相色谱仪(LC-20AT,SPD-20A,日本岛津公司);C18半制备色谱柱(250 mm×10 mm,5 μm,美国Kromsil公司);Sephadex LH-20凝胶(美国GE公司);电子天平(EL204,梅特勒-托利多仪器有限公司);旋转蒸发仪(东京理化器械独资工厂);化学试剂(分析纯,国药集团化学试剂有限公司);氘代试剂(德国Merck公司);薄层色谱硅胶板(HSGF254,烟台江友硅胶开发有限公司);各种柱色谱用硅胶均为青岛海洋化工有限公司出品。
平卧菊三七采自江西省靖安县,由南昌市食品药品检验所吴蓓副主任药师鉴定为平卧菊三七Gynura procumbens (Lour.) Merr全草。
2 提取与分离平卧菊三七药材15 kg粉碎,加8倍量70%乙醇加热提取1.5 h,滤过,滤渣再用8倍量70%乙醇加热提取1.5 h,滤过。合并滤液,浓缩,蒸干,得药材乙醇提取液浸膏。用适量蒸馏水将浸膏分散,分别依次用石油醚、二氯甲烷、醋酸乙酯多次萃取,各部分萃取液经减压回收溶剂,得石油醚萃取物310 g,二氯甲烷萃取物370 g,醋酸乙酯萃取物110 g,水部位900 g。将醋酸乙酯萃取物经硅胶柱色谱,依次用二氯甲烷-甲醇(100∶0、95∶5、85∶15、70∶30、50∶50、100∶0)洗脱,得到6个部位Fr. 1~6。Fr. 2经硅胶柱色谱,依次用石油醚-醋酸乙酯(70∶30、60∶40、50∶50、40∶60、30∶70、0∶100)洗脱,得到6个部分Fr. 2-1~2-6。Fr. 2-2通过Sephadex LH-20柱色谱及半制备高效液相色谱分离得到化合物1(29 mg)、2(6 mg)、3(8 mg)、4(38 mg)、7(45 mg)和15(330 mg),Fr. 2-4通过Sephadex LH-20柱色谱及半制备高效液相色谱分离得到化合物11(15 mg)和12(11 mg),Fr. 2-5通过Sephadex LH-20柱色谱及半制备高效液相色谱分离得到化合物9(9 mg)、10(10 mg)、16(16 mg)和5(17 mg);Fr. 2-6通过Sephadex LH-20柱色谱及半制备高效液相色谱分离得到化合物6(8 mg)、8(2 mg)、13(15 mg)和14(12 mg)。
3 结构鉴定化合物1:黄色粉末(甲醇);ESI-MS m/z: 301 [M-H]−,分子式为C15H10O7。1H-NMR (600 MHz,C5D5N) δ: 8.62 (1H,d,J = 2.0 Hz,H-2′),8.13 (1H,dd,J = 8.3,2.0 Hz,H-6′),7.40 (1H,d,J = 8.4 Hz,H-5′),6.78 (1H,d,J = 2.0 Hz,H-6),6.74 (1H,d,J = 2.0 Hz,H-8);13C-NMR (150 MHz,C5D5N) δ: 94.6 (C-6′),99.6 (C-8),104.8 (C-10),117.0 (C-5′),121.4 (C-6′),138.2 (C-3),147.4 (C-2),148.1 (C-4′),157.8 (C-5),162.8 (C-9),165.9 (C-7),177.6 (C-4)。以上数据与文献报道基本一致[5],故鉴定化合物1为槲皮素。
化合物2:黄色粉末(甲醇);ESI-MS m/z: 269 [M-H]−,分子式为C15H10O5。1H-NMR (600 MHz,C5D5N) δ: 13.08,10.80,10.40 (3H,s,3×OH),7.94 (2H,d,J = 8.6 Hz,H-2′,6′),6.95 (2H,d,J = 8.6 Hz,H-3′,5′),6.50 (1H,d,J = 1.6 Hz,H-8),6.81 (1H,s,H-3),6.17 (1H,d,J = 1.6 Hz,H-6);13C-NMR (150 MHz,C5D5N) δ: 166.5 (C-2),104.6 (C-3),183.4 (C-4),159.2 (C-5),100.7 (C-6),165.2 (C-7),95.5 (C-8),163.8 (C-9),105.6 (C-10),123.0 (C-1′),129.5 (C-2′,6′),117.5 (C-3′,5′),163.3 (C-4′)。以上数据与文献报道基本一致[6],故鉴定化合物2为芹菜素。
化合物3:黄色粉末(甲醇);ESI-MS m/z: 285 [M-H]−,分子式为C15H10O6。1H-NMR (600 MHz,C5D5N) δ: 7.92 (1H,d,J = 1.8 Hz,H-2′),7.56 (1H,dd,J = 8.4,1.7 Hz,H-6′),7.30 (1H,d,J = 8.3 Hz,H-5′),6.94 (1H,s,H-3),6.78 (1H,d,J = 1.8 Hz,H-8),6.71 (1H,d,J = 1.8 Hz,H-6);13C-NMR (150 MHz,C5D5N) δ: 165.5 (C-2),104.7 (C-3),183.4 (C-4),159.2 (C-5),100.6 (C-6),166.4 (C-7),95.4 (C-8),163.8 (C-9),105.7 (C-10),123.5 (C-1′),115.3 (C-2′),148.4 (C-3′),152.3 (C-4′),117.5 (C-5′),120.2 (C-6′)。以上数据与文献报道基本一致[7],故鉴定化合物3为木犀草素。
化合物4:黄色粉末(甲醇);ESI-MS m/z: 285 [M-H]−,分子式为C15H10O6。1H-NMR (600 MHz,C5D5N) δ: 8.12 (2H,d,J = 8.6 Hz,H-2′,6′),6.95 (2H,d,J = 8.6 Hz,H-3′,5′),6.43 (1H,d,J = 1.2 Hz,H-8),6.23 (1H,d,J = 1.2 Hz,H-6);13C-NMR (150 MHz,C5D5N) δ: 177.9 (C-4),166.1 (C-7),163.0 (C-5),161.3 (C-9),158.0 (C-4′),148.1 (C-2),138.4 (C-3),131.1 (C-2′,6′),124.0 (C-1′),116.9 (C-3′,5′),105.0 (C-10),99.8 (C-6),94.9 (C-8)。以上数据与文献报道基本一致[8],故鉴定化合物4为山柰酚。
化合物5:黄色粉末(甲醇);ESI-MS m/z: 447 [M-H]−,分子式为C21H20O11。1H-NMR (600 MHz,C5D5N) δ: 8.46 (2H,d,J = 8.6 Hz,H-2′,6′),7.21 (1H,d,J = 5.9 Hz,H-8),6.73 (2H,dd,J = 1.2,5.9 Hz,H-3′,5′),6.32 (1H,d,J = 5.9 Hz,H-6),4.44~4.02 (6H,m,sugar-H);13C-NMR (150 MHz,C5D5N) δ: 158.2 (C-2),135.2 (C-3),179.4 (C-4),157.5 (C-5),100.5 (C-6),166.6 (C-7),95.3 (C-8),163.5 (C-9),105.9 (C-10),122.6 (C-1′),132.5 (C-2′,6′),116.7 (C-3′,5′),162.3 (C-4′),104.7 (C-1″),79.7 (C-5″),79.2 (C-3″),76.7 (C-2″),72.1 (C-4″),63.3 (C-6″)。以上数据与文献报道基本一致[9],故鉴定化合物5为黄芪苷。
化合物6:黄色结晶(甲醇);ESI-MS m/z: 473 [M-H]−,分子式为C23H22O11。1H-NMR (600 MHz,C5D5N) δ: 8.05 (2H,q,J = 10.4 Hz,H-2′,6′),69.0 (2H,q,J = 10.4 Hz,H-3′,5′),6.45 (1H,d,J = 2.0 Hz,H-8),6.25 (1H,d,J = 2.0 Hz,H-6),5.18 (1H,d,J = 10.4 Hz,H-1″),3.18~4.17 (6H,m,sugar-H),4.50 (3H,s,-COCH3);13C-NMR (150 MHz,C5D5N) δ: 158.0 (C-2),135.3 (C-3),179.0 (C-4),163.1 (C-5),100.2 (C-6),166.4 (C-7),95.0 (C-8),158.1 (C-9),105.5 (C-10),122.1 (C-1′),132.2 (C-2′,6′),116.3 (C-3′,5′),162.0 (C-4′),104.4 (C-1″),76.0 (C-2″),78.6 (C-3″),71.4 (C-4″),76.3 (C-5″),64.5 (C-6″),171.0 (COCH3),20.8 (COCH3)。以上数据与文献报道基本一致[10],故鉴定化合物6为山柰酚-5-O-(6″-O-乙酰基)-β-D-吡喃葡萄糖苷。
化合物7:黄色针晶(醋酸乙酯);ESI-MS m/z: 283 [M-H]−,分子式为C16H12O5。1H-NMR (600 MHz,C5D5N) δ: 13.21 (1H,s,OH),7.90 (2H,m,Ar-2H),7.60 (3H,m,Ar-3H),7.12 (1H,s,H-8),6.66 (1H,s,H-3),3.90 (3H,s,OCH3);13C-NMR (150 MHz,C5D5N) δ: 156.2 (C-2),106.4 (C-3),184.0 (C-4),150.5 (C-5),132.8 (C-6),164.6 (C-7),92.3 (C-8),148.4 (C-9),107.5 (C-10),132.6 (C-1′),127.4 (C-2′),130.1 (C-3′),133.1 (C-4′),130.1 (C-5′),127.4 (C-6′),57.2 (OCH3)。以上数据与文献报道基本一致[11],故鉴定化合物7为7-甲醚黄芩素。
化合物8:褐色结晶(甲醇);ESI-MS m/z: 177 [M-H]−,分子式为C10H10O3。1H-NMR (600 MHz,MeOD) δ: 7.61 (1H,d,J = 16.0 Hz,H-7),7.45 (2H,d,J = 8.6 Hz,H-2,6),6.80 (2H,d,J = 8.7 Hz,H-3,5),6.32 (1H,d,J = 15.9 Hz,H-8),3.75 (3H,s,OCH3);13C-NMR (150 MHz,MeOD) δ: 169.8 (C-9),161.3 (C-4),146.6 (C-7),131.1 (C-2,6),127.1 (C-1),116.8 (C-3,5),114.9 (C-8),52.0 (OCH3)。以上数据与文献报道基本一致[12],故鉴定化合物8为4-甲氧基肉桂酸。
化合物9:无色油状物(甲醇);ESI-MS m/z: 269 [M-H]−,分子式为C13H18O6。1H-NMR (600 MHz,C5D5N) δ: 7.53 (2H,d,J = 7.1 Hz,H-2,6),7.35 ( 2H,t,J = 7.1 Hz,H-3,5),7.27 (1H,t,J = 7.1 Hz,H-4),4.67,4.93 (2H,d,J = 11.9 Hz,H-7),4.45 (1H,d,J = 7.7 Hz,H-1′),3.66 (1H,dd,J = 11.9,4.0 Hz,H-6′a),3.90 (1H,dd,J = 11.9,2.0 Hz,H-6′b),3.24~3.64 (4H,m,H-2′~5′);13C-NMR (150 MHz,C5D5N) δ: 139.3 (C-1),128.6 (C-2,6),129.0 (C-3,5),128.1 (C-4),72.0 (C-7),104.4 (C-1′),75.6 (C-2′),79.0 (C-3′),71.2 (C-4′),79.0 (C-5′),63.2 (C-6′)。以上数据与文献报道基本一致[13],故鉴定化合物9为苄基葡萄糖苷。
化合物10:无色油状物(甲醇);ESI-MS m/z: 283 [M-H]−,分子式为C14H20O6。1H-NMR (600 MHz,MeOD) δ: 7.33~7.18 (5H,m,H-2,3,4,5,6),4.13 (1H,m,H-8a),3.70 (1H,m,H-8b),2.98 (2H,m,H-7);13C-NMR (150 MHz,MeOD) δ: 140.1 (C-1),130.0 (C-2,6),129.3 (C-3,5),127.2 (C-4),71.7 (C-8),37.2 (C-7),104.4 (C-1′),78.0 (C-3′),78.1 (C-5′),75.1 (C-2′),71.7 (C-4′),62.8 (C-6′)。以上数据与文献报道基本一致[14],故鉴定化合物10为2-苯乙基-O-β-D-吡喃葡萄糖苷。
化合物11:白色粉末(甲醇);ESI-MS m/z: 529 [M-H]−,分子式为C26H26O12。1H-NMR (600 MHz,MeOD) δ: 7.67 (1H,d,J = 15.9 Hz,H-7″),7.59 (1H,d,J = 15.9 Hz,H-7′),7.11 (2H,d,J = 1.8 Hz,H-2′,2″),7.01 (2H,d,J = 8.1 Hz,H-5′,5″),6.83 (2H,dd,J = 8.1,3.7 Hz,H-6′,6″),6.38 (1H,d,J = 15.9 Hz,H-8′),6.29 (1H,d,J = 15.9 Hz,H-8″),5.42 (1H,dd,J = 8.1,3.7 Hz,H-5),5.36 (1H,m,H-3),4.03 (1H,dd,J = 8.1,3.7 Hz,H-4),3.74 (3H,s,COOCH3),2.42~2.31 (2H,m,H-6ax,2eq),2.26 (1H,dd,J = 14.1,3.7 Hz,H-6eq),2.16 (1H,dd,J = 13.8,8.1 Hz,H-2ax);13C-NMR (150 MHz,MeOD) δ: 74.7 (C-1),35.7 (C-2),72.0 (C-3),69.7 (C-4),72.2 (C-5),36.7 (C-6),127.6,127.9 (C-1′,1″),115.2 (C-2′,2″),146.8,146.9 (C-3′,3″),149.5,149.7 (C-4′,4″),116.5,116.6 (C-5′,5″),123.0,123.1 (C-6′,6″),147.1,147.4 (C-7′,7″),114.9,115.5 (C-8′,8″),168.0,168.7 (C-9′,9″),175.6 (COOCH3),53.0 (COOCH3)。以上数据与文献报道基本一致[15],故鉴定化合物11为3,5-二咖啡酰基奎宁酸甲酯。
化合物12:白色粉末(甲醇);ESI-MS m/z: 543 [M-H]−,分子式为C27H28O12。1H-NMR (600 MHz,MeOD) δ: 7.64 (1H,d,J = 15.9 Hz,H-8″),7.60 (1H,d,J = 15.9 Hz,H-8′),7.14 (1H,d,J = 1.9 Hz,H-2″),7.09 (1H,d,J = 1.9 Hz,H-2′),7.04 (1H,dd,J = 8.1,1.9 Hz,H-5″),7.02 (1H,dd,J = 8.1,1.9 Hz,H-5′),6.89 (1H,d,J = 8.1 Hz,H-6″),6.84 (1H,d,J = 8.1 Hz,H-6′),6.39 (1H,d,J = 15.9 Hz,H-7′),6.27 (1H,d,J = 15.9 Hz,H-7″),5.49~5.43 (1H,m,H-3),5.36 (1H,m,H-5),4.20 (2H,q,J = 7.1 Hz,H-8),4.03 (1H,dd,J = 6.3,2.9 Hz,H-4),2.38 (2H,m,H-2),2.27~2.16 (2H,m,H-6),1.29 (3H,t,J = 7.1 Hz,H-9);13C-NMR (150 MHz,MeOD) δ: 74.6 (C-1),36.7 (C-2),72.0 (C-3),69.8 (C-4),72.3 (C-5),35.6 (C-6),127.6,127.9 (C-1′,1″),116.6,116.8 (C-2′,2″),115.5,116.5 (C-3′,3″),149.5,149.7 (C-4′,4″),147.1,147.4 (C-5′,5″),114.9,115.2 (C-6′,6″),123.0 (C-7′,7″),146.8,146.9 (C-8′,8″),168.0,168.7 (C-9′,9″),175.2 (COOR),62.6 (OCH2),14.3 (OCH2CH3)。以上数据与文献报道基本一致[16],故鉴定化合物12为3,5-二咖啡酰基奎宁酸乙酯。
化合物13:白色粉末(甲醇);ESI-MS m/z: 529 [M-H]−,分子式为C26H26O12。1H-NMR (600 MHz,C5D5N) δ: 7.60 (1H,d,J = 8.1 Hz,H-7′),7.54 (1H,d,J = 8.1 Hz,H-7″),7.15 (1H,d,J = 1.7 Hz,H-2′),7.06 (1H,d,J = 1.7 Hz,H-2″),6.65 (1H,dd,J = 8.1,2.5 Hz,H-6′),6.61 (1H,dd,J = 8.1,2.5 Hz,H-6″),6.58 (2H,d,J = 2.5 Hz,H-5′,5″),6.15 (1H,d,J = 8.1 Hz,H-8′),6.06 (1H,d,J = 8.1 Hz,H-8″),5.41 (1H,m,H-3),4.97 (1H,dd,J = 8.1,1.7 Hz,H-4),4.22 (1H,m,H-5),3.73 (3H,s,OCH3),2.23 (2H,m,H-2),2.14 (2H,m,H-6);13C-NMR (150 MHz,C5D5N) δ: 75.5 (C-1),38.9 (C-2),68.9 (C-3),74.9 (C-4),68.2 (C-5),38.9 (C-6),126.9 (C-1′,1″),116.0,116.1 (C-2′,2″),146.8,146.9 (C-3′,3″),150.8,150.9 (C-4′,4″),116.9,117.0 (C-5′,5″),122.5 (C-6′,6″),147.8,147.9 (C-7′,7″),114.7,114.9 (C-8′,8″),167.0,167.5 (C-9′,9″),174.9 (COOCH3),52.6 (-OCH3)。以上数据与文献报道基本一致[17],故鉴定化合物13为3,4-二咖啡酰基奎宁酸甲酯。
化合物14:白色粉末(甲醇);ESI-MS m/z: 529 [M-H]−,分子式为C26H26O12。1H-NMR (600 MHz,MeOD) δ: 7.55 (1H,d,J = 6.6 Hz,H-7′),7.53 (1H,d,J = 6.5 Hz,H-7″),7.02 (2H,m,H-2′,2″),6.90 (1H,dd,J = 8.1,1.7 Hz,H-6′),6.87 (1H,dd,J = 8.2,1.5 Hz,H-6″),6.75 (1H,d,J = 8.2 Hz,H-5′),6.73 (1H,d,J = 8.1 Hz,H-5″),6.27 (1H,d,J = 3.3 Hz,H-8′),6.24 (1H,d,J = 3.3 Hz,H-8″),5.61 (1H,m,H-5),5.02 (1H,dd,J = 8.2,3.1 Hz,H-4),4.35 (1H,m,H-3),3.74 (3H,s,OCH3);13C-NMR (150 MHz,MeOD) δ: 75.2 (C-1),41.3 (C-2),69.8 (C-3),75.2 (C-4),66.0 (C-5),36.8 (C-6),127.7 (C-1′,1″),115.1 (C-2′,2″),146.8 (C-3′,3″),149.6 (C-4′,4″),116.5 (C-5′,5″),123.1,123.3 (C-6′,6″),147.4 (C-7′,7″),114.8,115.0 (C-8′,8″),168.5,168.6 (C-9′,9″),176.2 (COOCH3),53.0 (-OCH3)。以上数据与文献报道基本一致[18],故鉴定化合物14为4,5-二咖啡酰基奎宁酸甲酯。
化合物15:无色针晶(甲醇);ESI-MS m/z: 153[M-H]−,分子式为C7H6O4。1H-NMR (600 MHz,MeOD) δ: 7.48 (1H,s,H-2),7.44 (1H,d,J = 6.1 Hz,H-6),6.83 (1H,d,J = 6.1 Hz,H-5);13C-NMR (150 MHz,MeOD) δ: 170.4 (C=O),151.4 (C-4),145.9 (C-3),124.0 (C-6),123.0 (C-1),117.7 (C-5),115.8 (C-2)。以上数据与文献报道基本一致[19],故鉴定化合物15为原儿茶酸。
化合物16:白色粉末(甲醇);ESI-MS m/z: 325 [M-H]−,分子式为C16H22O7。1H-NMR (600 MHz,MeOD) δ: 7.13 (1H,d,J = 8.2 Hz,H-6),6.87 (1H,s,H-3),6.77 (1H,d,J = 8.2 Hz,H-5),6.00 (1H,m,H-8),5.12 (1H,d,J = 19.4 Hz,H-9b),5.08 (1H,d,J = 19.4 Hz,H-9a),4.91 (1H,d,J = 8.0 Hz,H-1′),3.91 (1H,dd,J = 12.0,1.8 Hz,H-6b′),3.88 (3H,s,H-10),3.74 (1H,dd,J = 11.3,3.5 Hz,H-6a′),3.45~3.35 (6H,m,H-2′,3′,4′,5′,7);13C-NMR (150 MHz,MeOD) δ: 150.8 (C-2),146.3 (C-1),139.0 (C-8),136.5 (C-4),122.1 (C-5),118.3 (C-6),115.9 (C-9),114.2 (C-3),103.1 (C-1′),78.2 (C-3′),77.83 (C-5′),74.9 (C-2′),71.4 (C-4′),62.5 (C-6′),56.7 (C-10),40.7 (C-7)。以上数据与文献报道基本一致[20],故鉴定化合物16为丁香酚苷。
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