2. 中国科学院大学, 北京 100049
2. University of Chinese Academy of Sciences, Beijing 100049, China
刘寄奴Artemisiae Anomalae Herba,别名金寄奴、六月霜、消食草,为菊科植物奇蒿Artemisia anomala S. Moore或白苞蒿Artemisia actiflora Wall. Ex DC. 的干燥地上部分,收录于《中国药典》2010年版一部附录中;为多年生直立草本,生于林边、灌丛中、河岸旁,主产于江苏、浙江、江西、福建等地,主销华东和华南各地,所以又称南刘寄奴。其全草入药,有止血消肿、破瘀通经、清热解毒和消食化积之功效,常用于治疗经闭、痛经、产后瘀滞腹痛、跌打损伤、金疮出血、烫伤、便血、尿血、风湿痹痛、痈疮肿毒、食积腹痛、泄泻痢疾[1]。该植物含挥发油,主要成分有倍半萜内酯类、黄酮苷类、酚类、氨基酸等[2]。据文献报道,刘寄奴氯仿提取物作为其抗真菌活性组分,抗真菌作用已接近临床常规抗真菌药物效果[3];而刘寄奴醋酸乙酯提取物中的总黄酮则被确定为其抗炎活性组分[4]。为了更深入地阐明刘寄奴的药效物质基础,本实验对刘寄奴进行了系统的化学成分研究,从中分离得到15个化合物,包括7个甾体和8个黄酮类化合物,分别鉴定为β-谷甾醇(β-sitosterol,1)、β-胡萝卜苷(β-daucosterol,2)、schleicheol 2(3)、α-菠甾醇(α-spinasterol,4)、3β-羟基-5α,8α-过氧-6,22-麦角甾二烯(5α,8α-epidioxy- rgosta-6,22-dien-3β-ol,5)、3β-羟基-5α,8α-过氧-6,9(11),22-麦角甾三烯(5α,8α-epidioxy-ergosta-6,9(11),22-trien-3β-ol,6)、22E-3β,5α-二羟基-麦角甾-7,22-二烯-6-酮(22E-3β,5α-dihydroxyergosta-7,22-dien- 6-one,7)、柚皮素(naringenin,8)、木犀草素(luteolin,9)、山柰酚(kaempferol,10)、柯伊利素(chrysoeriol,11)、香叶木素(diosmetin,12)、棕矢车菊素(jaceosidin,13)、异鼠李素-3-O-葡萄糖(isorhamnetin 3-O-gluco- side,14)、橙皮素-7-O-β-D-葡萄糖(hesperetin-7- O-β-D-glucopyranoside,15)。其中化合物5、6、12~14为首次从该植物中分离得到,化合物3为首次从蒿属植物中分离得到,化合物7、15为首次从菊科植物中分离得到。
1 仪器与材料Bruker Avance—400(德国Bruker公司)和Varian Unity Inova 400核磁共振仪(美国Varian公司);制备高效液相色谱仪(江苏汉邦科技有限公司);WFH—203(ZF—1)三用紫外分析仪(上海精科实业有限公司);GMF—320A多级闪蒸器(河南金鼎科技发展有限公司),OKPURE实验室超纯水器(上海涞科仪器有限公司)。Sephadex LH-20(瑞典GE Healthcare公司),薄层色谱硅胶(GF254,10~40 μm,青岛海洋化工厂);柱色谱硅胶(200~300目,青岛海洋化工厂);ODS柱色谱硅胶(50 μm,日本YMC公司)。薄层显色剂为95%硫酸-乙醇溶液,所用试剂为分析纯或化学纯,制备HPLC和ODS反相柱色谱所用水均为超纯水。
刘寄奴饮片于2012年购于宁波德康生物制品有限公司,经中国科学院兰州化学物理研究所齐欢阳副研究员鉴定为菊科(Compositae)蒿属Artemisia L.植物奇蒿Artemisia anomala S. Moore的干燥地上部分。样本(ZY2012A001)存放于中国科学院兰州化学物理研究所西北特色植物资源化学重点实验室。
2 提取与分离刘寄奴14 kg,粉碎后于55 ℃下用95%乙醇加热回流提取,每千克刘寄奴用5 L 95%乙醇提取3次,每次2 h,减压滤过,合并提取液,通过多级闪蒸器减压浓缩得乙醇浸膏(800 g)。浸膏加适量水混悬后,依次用等体积的石油醚、醋酸乙酯、正丁醇萃取,得石油醚部分154 g、醋酸乙酯部分200 g,正丁醇部分95 g。石油醚部分以石油醚-醋酸乙酯(30∶1、15∶1、8∶1、4∶1、2∶1、0∶1)进行梯度洗脱,各组分经硅胶柱色谱、ODS反相柱色谱、Sephadex LH-20柱色谱和制备HPLC等反复洗脱得到化合物1(100 mg)、3(4 mg)、4(12 mg)、5(66 mg)、6(24 mg)、7(3 mg)。醋酸乙酯部分以石油醚-丙酮(30∶1、15∶1、8∶1、4∶1、2∶1、0∶1)梯度洗脱,经反复硅胶柱色谱和Sephadex LH-20柱色谱得到化合物2(50 mg)、8(6 mg)、9(44 mg)、10(66 mg)、11和12(12 mg)、13(10 mg)、14(15 mg)、15(4 mg)。
3 结构鉴定化合物1:无色针晶(氯仿)。TLC检测紫外灯(λ254nm)下无荧光,5%硫酸-乙醇溶液显色呈紫色斑点。与β-谷甾醇对照品在多个溶剂体系下共薄层,斑点颜色及Rf值均一致,故鉴定化合物1为β-谷甾醇。
化合物2:白色粉末(丙酮)。TLC检测紫外灯(λ254)下无荧光,5%硫酸-乙醇溶液显紫红色斑点。与β-胡萝卜苷对照品在多个溶剂体系下共薄层,其色谱行为一致,故鉴定化合物2为β-胡萝卜苷。
化合物3:无色油状物(氯仿)。TLC检测紫外灯(λ254)下无荧光,5%硫酸-乙醇溶液显蓝色。1H-NMR (400 MHz,CDCl3) δ: 3.61 (1H,m,H-3),5.72 (1H,d,J = 5.2 Hz,H-6),3.25 (1H,m,H-7),0.64 (3H,s,H-18),0.96 (3H,s,H-19),0.90 (3H,d,J = 6.4 Hz,H-21),0.82 (3H,d,J = 0.8 Hz,H-26),0.78 (3H,s,H-27),0.80 (3H,d,J = 2.4 Hz,H-29);13C-NMR (100 MHz,CDCl3) δ: 36.7 (C-1),31.5 (C-2),71.4 (C-3),42.3 (C-4),146.1 (C-5),120.7 (C-6),73.9 (C-7),37.2 (C-8),42.7 (C-9),37.4 (C-10),20.8 (C-11),39.0 (C-12),42.1 (C-13),49.1 (C-14),24.3 (C-15),28.3 (C-16),55.7 (C-17),11.5 (C-18),18.3 (C-19),36.1 (C-20),18.8 (C-21),33.9 (C-22),26.0 (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),56.8 (7-OCH3)。以上数据与文献报道一致[5],故鉴定化合物3为schleicheol 2。
化合物4:白色粉末(氯仿)。TLC检测紫外灯(λ254)下无荧光,5%硫酸-乙醇溶液显紫红色。1H-NMR (400 MHz,CDCl3) δ: 3.57 (1H,m,H-3),5.13 (1H,m,H-7),5.13 (1H,dd,J = 8.8,14.8 Hz,H-22),5.01 (1H,dd,J = 8.8,14.8 Hz,H-23),0.52 (3H,s,H-18),0.78 (3H,s,H-19),1.00 (3H,d,J = 6.4 Hz,H-21),0.82 (3H,d,J = 5.6 Hz,H-26),0.79 (3H,s,H-27),0.77 (3H,s,H-29);13C-NMR (100 MHz,CDCl3) δ: 37.1 (C-1),31.5 (C-2),71.0 (C-3),38.0 (C-4),40.2 (C-5),29.6 (C-6),117.4 (C-7),139.5 (C-8),49.4 (C-9),34.2 (C-10),21.5 (C-11),39.4 (C-12),43.3 (C-13),55.0 (C-14),23.0 (C-15),28.5 (C-16),55.9 (C-17),12.0 (C-18),13.0 (C-19),40.8 (C-20),21.4 (C-21),138.1 (C-22),129.4 (C-23),51.2 (C-24),31.9 (C-25),21.1 (C-26),19.0 (C-27),25.4 (C-28),12.2 (C-29)。以上数据与文献报道一致[6],故鉴定化合物4为α-菠甾醇。
化合物5:白色粉末(氯仿)。TLC检测紫外灯(λ254)下无荧光,5%硫酸-乙醇溶液显棕灰色。1H-NMR (400 MHz,CDCl3) δ: 3.95 (1H,m,H-3),6.22 (1H,d,J = 8.4 Hz,H-6),6.48 (1H,d,J = 8.4 Hz,H-7),5.20 (1H,dd,J = 7.2,15.2 Hz,H-22),5.11 (1H,dd,J = 8.4,15.2 Hz,H-23),0.78 (3H,s,H-18),0.79 (3H,s,H-19),0.97 (3H,d,J = 6.4 Hz,H-21),0.86 (3H,d,J = 6.4 Hz,H-26),0.81 (3H,d,J = 6.8 Hz,H-27),0.88 (3H,d,J = 6.8 Hz,H-28);13C-NMR (100 MHz,CDCl3) δ: 36.9 (C-1),30.1 (C-2),66.3 (C-3),51.0 (C-4),79.4 (C-5),130.7 (C-6),135.3 (C-7),82.1 (C-8),34.7 (C-9),36.9 (C-10),20.6 (C-11),39.3 (C-12),44.5 (C-13),51.7 (C-14),28.6 (C-15),23.4 (C-16),56.2 (C-17),12.9 (C-18),18.2 (C-19),39.7 (C-20),19.6 (C-21),135.2 (C-22),132.3 (C-23),42.7 (C-24),33.0 (C-25),20.9 (C-26),19.9 (C-27),17.5 (C-28)。以上数据与文献报道一致[7],故鉴定化合物5为3β-羟基-5α,8α-过氧-6,22-麦角甾二烯。
化合物6:白色粉末(氯仿)。TLC检测紫外灯(λ254)下无荧光,5%硫酸-乙醇溶液显紫红色。1H-NMR (400 MHz,CDCl3) δ: 4.01 (1H,m,H-3),6.29 (1H,d,J = 8.8 Hz,H-6),6.60 (1H,d,J = 8.8 Hz,H-7),5.43 (1H,d,J = 4.4 Hz,H-11),5.24 (1H,dd,J = 7.6,15.2 Hz,H-22),5.16 (1H,dd,J = 8.0,15.2 Hz,H-23),0.74 (3H,s,H-18),1.09 (3H,s,H-19),1.00 (3H,d,J = 6.4 Hz,H-21),0.82 (3H,d,J = 6.8 Hz,H-26),0.84 (3H,d,J = 6.8 Hz,H-27),0.92 (3H,d,J = 6.8 Hz,H-28);13C-NMR (100 MHz,CDCl3) δ: 32.6 (C-1),30.6 (C-2),66.3 (C-3),36.1 (C-4),82.7 (C-5),135.3 (C-6),130.7 (C-7),78.3 (C-8),142.7 (C-9),40.0 (C-10),119.7 (C-11),41.2 (C-12),43.6 (C-13),48.2 (C-14),20.9 (C-15),28.6 (C-16),55.9 (C-17),13.0 (C-18),25.5 (C-19),39.9 (C-20),20.7 (C-21),135.1 (C-22),132.5 (C-23),42.8 (C-24),33.1 (C-25),19.6 (C-26),19.9 (C-27),17.5 (C-28)。以上数据与文献报道一致[8],故鉴定化合物6为3β-羟基-5α,8α-过氧-6,9(11),22-麦角甾三烯。
化合物7:白色粉末(氯仿)。(nm): 253。5%硫酸-乙醇溶液显姜黄色。1H-NMR (400 MHz,CDCl3) δ: 4.03 (1H,m,H-3),5.66 (1H,s,H-7),5.25 (1H,dd,J = 7.2,15.2 Hz,H-22),5.16 (1H,dd,J = 8.4,15.2 Hz,H-23),0.61 (3H,s,H-18),0.96 (3H,s,H-19),1.04 (3H,s,H-21),0.83 (3H,s,H-26),0.83 (3H,s,H-27),0.92 (3H,s,H-28);13C-NMR (100 MHz,CDCl3) δ: 30.4 (C-1),30.3 (C-2),67.5 (C-3),38.9 (C-4),77.9 (C-5),198.2 (C-6),119.7 (C-7),165.2 (C-8),44.0 (C-9),40.5 (C-10),22.0 (C-11),36.6 (C-12),44.8 (C-13),55.8 (C-14),22.5 (C-15),27.8 (C-16),56.1 (C-17),12.7 (C-18),17.6 (C-19),40.2 (C-20),19.7 (C-21),135.0 (C-22),132.6 (C-23),42.9 (C-24),33.1 (C-25),21.1 (C-26),20.0 (C-27),16.4 (C-28)。以上数据与文献报道一致[9],故鉴定化合物7为22E-3β,5α-二羟基-麦角甾-7,22-二烯-6-酮。
化合物8:橘红色粉末(甲醇)。(nm): 331,288。5%硫酸-乙醇溶液先显黄色,后变成桔黄色。1H-NMR (400 MHz,DMSO-d6) δ: 5.44 (1H,dd,J = 2.0,12.8 Hz,H-2),2.66 (1H,dd,J = 2.4,17.2 Hz,H-3a),3.26 (1H,dd,J = 13.2,17.2 Hz,H-3b),5.87 (2H,s,H-6,8),7.30 (2H,d,J = 8.4 Hz,H-2′,6′),6.78 (2H,d,J = 8.4 Hz,H-3′,5′),12.15 (1H,s,5-OH),9.61 (1H,s,4′-OH);13C-NMR (100 MHz,DMSO-d6) δ: 78.4 (C-2),42.0 (C-3),196.4 (C-4),163.5 (C-5),95.0 (C-6),166.7 (C-7),95.8 (C-8),162.9 (C-9),101.7 (C-10),128.8 (C-1′),128.3 (C-2′,6′),115.1 (C-3′,5′),157.7 (C-4′)。以上数据与文献报道一致[10],故鉴定化合物8为柚皮素。
化合物9:黄色粉末(甲醇)。(nm): 353,267,254。5%硫酸-乙醇溶液显黄色。1H-NMR (400 MHz,DMSO-d6) δ: 6.68 (1H,s,H-3),6.20 (1H,s,H-6),6.45 (1H,s,H-8),7.41 (1H,d,J = 2.0 Hz,H-2′),6.90 (1H,d,J = 6.4 Hz,H-5′),7.41 (1H,dd,J = 2.0,8.0 Hz,H-6′),12.99 (1H,s,5-OH);13C-NMR (100 MHz,DMSO-d6) δ: 164.4 (C-2),103.4 (C-3),182.1 (C-4),157.8 (C-5),99.3 (C-6),164.6 (C-7),94.3 (C-8),162.0 (C-9),104.2 (C-10),122.0 (C-1′),113.9 (C-2′),146.2 (C-3′),150.2 (C-4′),116.5 (C-5′),119.4 (C-6′)。以上数据与文献报道一致[11],故鉴定化合物9为木犀草素。
化合物10:黄色粉末(甲醇)。(nm): 365,267。5%硫酸-乙醇溶液显桔黄色。1H-NMR (400 MHz,DMSO-d6) δ: 6.20 (1H,s,H-6),6.45 (1H,s,H-8),8.06 (1H,d,J = 7.2 Hz,H-2′,6′),6.94 (1H,d,J = 7.2 Hz,H-3′,5′),12.49 (1H,s,5-OH);13C-NMR (100 MHz,DMSO-d6) δ: 147.3 (C-2),136.1 (C-3),176.4 (C-4),156.7 (C-5),98.7 (C-6),164.4 (C-7),94.0 (C-8),161.2 (C-9),103.5 (C-10),122.2 (C-1′),130.0 (C-2′,6′),115.9 (C-3′,5′),159.7 (C-4′)。以上数据与文献报道一致[12],故鉴定化合物10为山柰酚。
化合物11:黄色粉末(甲醇)。(nm): 343,268,252。5%硫酸-乙醇溶液显浅红色。1H-NMR (400 MHz,DMSO-d6) δ: 6.89 (1H,s,H-3),6.18 (1H,d,J = 2.0 Hz,H-6),6.50 (1H,d,J = 2.0 Hz,H-8),7.41 (1H,d,J = 2.4 Hz,H-2′),7.06 (1H,d,J = 8.8 Hz,H-5′),6.75 (1H,s,H-6′),12.96 (1H,s,5-OH),10.91 (1H,s,7-OH),9.51 (1H,s,4′-OH),3.88 (3H,s,3′-OCH3);13C-NMR (100 MHz,DMSO-d6) δ: 163.7 (C-2),103.5 (C-3),181.7 (C-4),157.3 (C-5),98.9 (C-6),164.2 (C-7),93.9 (C-8),161.4 (C-9),103.2 (C-10),120.4 (C-1′),110.2 (C-2′),150.7 (C-3′),148.0 (C-4′),115.8 (C-5′),121.5 (C-6′),56.0 (3′-OCH3)。以上数据与文献报道一致[13],故鉴定化合物11为柯伊利素。
化合物12:黄色粉末(甲醇)。(nm): 343,268,252。5%硫酸-乙醇溶液显浅红色。1H-NMR (400 MHz,DMSO-d6) δ: 6.75 (1H,s,H-3),6.18 (1H,d,J = 2.0 Hz,H-6),6.45 (1H,d,J = 2.0 Hz,H-8),7.54 (1H,m,H-2′),6.90 (1H,d,J = 8.0 Hz,H-5′),6.75 (1H,s,H-6′),12.93 (1H,s,5-OH),10.91 (1H,s,7-OH),9.51 (1H,s,3′-OH),3.85 (3H,s,4′-OCH3);13C-NMR (100 MHz,DMSO-d6) δ: 163.5 (C-2),103.8 (C-3),181.8 (C-4),157.3 (C-5),98.9 (C-6),164.2 (C-7),94.0 (C-8),161.5 (C-9),103.7 (C-10),118.7 (C-1′),113.0 (C-2′),146.8 (C-3′),151.1 (C-4′),112.1 (C-5′),123.0 (C-6′),55.8 (4′-OCH3)。以上数据与文献报道一致[14],故鉴定化合物12为香叶木素。
化合物13:黄色油状物(甲醇)。(nm): 339,274。5%硫酸-乙醇溶液显黄色。1H-NMR (400 MHz,DMSO-d6) δ: 6.61 (1H,s,H-3),6.88 (1H,s,H-8),7.54 (1H,s,H-2′),6.90 (1H,d,J = 8.8 Hz,H-5′),7.55 (1H,s,H-6′),13.08 (1H,s,5-OH),3.74 (3H,s,6-OCH3),3.88 (3H,s,4′-OCH3);13C-NMR (100 MHz,DMSO-d6) δ: 163.7 (C-2),102.7 (C-3),182.2 (C-4),152.7 (C-5),131.4 (C-6),152.4 (C-7),94.3 (C-8),157.4 (C-9),104.0 (C-10),121.5 (C-1′),110.2 (C-2′),150.7 (C-3′),148.0 (C-4′),115.8 (C-5′),120.3 (C-6′),55.9 (6-OCH3),59.9 (4′-OCH3)。以上数据与文献报道一致[15],故鉴定化合物13为棕矢车菊素。
化合物14:黄色颗粒状固体(甲醇)。 (nm): 348,266,257。5%硫酸-乙醇溶液显黄色。1H-NMR (400 MHz,DMSO-d6) δ: 6.20 (1H,d,J = 2.0 Hz,H-6),6.43 (1H,d,J = 2.0 Hz,H-8),7.94 (1H,d,J = 2.0 Hz,H-2′),6.91 (1H,d,J = 8.4 Hz,H-5′),7.48 (1H,dd,J = 2.0,8.4 Hz,H-6′),5.56 (1H,d,J = 7.2 Hz,H-1″),12.61 (1H,s,5-OH),10.87 (1H,s,7-OH),9.81 (1H,s,4′-OH),3.83 (3H,s,3′-OCH3);13C-NMR (100 MHz,DMSO-d6) δ: 156.4 (C-2),132.9 (C-3),177.4 (C-4),161.2 (C-5),98.8 (C-6),164.2 (C-7),93.7 (C-8),156.3 (C-9),104.1 (C-10),121.1 (C-1′),115.2 (C-2′),149.4 (C-3′),146.9 (C-4′),113.5 (C-5′),122.0 (C-6′),100.7 (C-1″),74.3 (C-2″),77.5 (C-3″),69.8 (C-4″),76.4 (C-5″),60.6 (C-6″),55.7 (3′-OCH3)。以上数据与文献报道一致[16],故鉴定化合物14为异鼠李素-3-O-葡萄糖。
化合物15:白色颗粒状固体(甲醇)。 (nm): 331,284。5%硫酸-乙醇溶液不显色。1H-NMR (400 MHz,DMSO-d6) δ: 5.50 (1H,dd,J = 3.2,12.4 Hz,H-2),2.77 (1H,dd,J = 3.2,17.2 Hz,H-3a),3.19 (1H,m,H-3b),6.13 (1H,d,J = 2.0 Hz,H-6),6.15 (1H,d,J = 2.0 Hz,H-8),6.93 (1H,s,H-2′),6.88 (1H,d,J = 2.0,8.0 Hz,H-5′),6.95 (1H,d,J = 8.0 Hz,H-6′),4.97 (1H,d,J = 7.2 Hz,H-1″),12.05 (1H,s,5-OH),9.13 (1H,s,3′-OH),3.77 (3H,s,4′-OCH3);13C-NMR (100 MHz,DMSO-d6) δ: 78.4 (C-2),42.1 (C-3),197.0 (C-4),162.9 (C-5),96.4 (C-6),165.3 (C-7),95.4 (C-8),162.6 (C-9),103.2 (C-10),130.9 (C-1′),114.1 (C-2′),146.5 (C-3′),147.9 (C-4′),112.0 (C-5′),117.8 (C-6′),55.7 (4′-OCH3),99.6 (C-1″),73.0 (C-2″),77.1 (C-3″),69.5 (C-4″),76.3 (C-5″),60.5 (C-6″)。以上数据与文献报道一致[17],故鉴定化合物15为橙皮素-7-O-β-D-葡萄糖。
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