查显进,石 强,邵 峰*,张普照,刘荣华,杨 明,饶倩如
泽漆化学成分研究
查显进1,石 强2,邵 峰1*,张普照1,刘荣华1,杨 明1,饶倩如1
1. 江西中医药大学 现代中药制剂教育部重点实验室,江西 南昌 330004 2. 江西中医药大学,岐黄国医书院,江西 南昌 330004
研究泽漆的化学成分。采用硅胶柱色谱、Sephadex LH-20柱色谱及制备液相色谱等方法进行分离纯化,并经理化性质与光谱数据鉴定化合物结构。从泽漆70%乙醇提取物中分离得到23个化合物,依次鉴定为β-谷甾醇(1)、euphoscopin B(2)、对羟基苯乙酮(3)、euphoscopin F(4)、euphoscopin C(5)、nepehinol(6)、4-羟基-3,5-二甲氧基苯甲醛(7)、antiquorin(8)、1-吲哚-3-甲醛(9)、7-羟基-6-甲氧基香豆素(10)、泽漆内酯A(11)、euphoheliosnoid A(12)、松脂素(13)、(+)-去氢催吐萝芙木醇(14)、loliolide(15)、1-(4-羟基-3-甲氧基苯基)-3-羟基丙-1-酮(16)、3-羟基乙酰吲哚(17)、橙皮酰胺(18)、rayalinol(19)、3--β--吡喃葡萄糖基泽漆内酯A(20)、柚皮素(21)、4′,5,7-三羟基异黄酮(22)、槲皮素(23)。化合物10、17、19、20、22为首次从大戟属植物中分离得到,化合物3、7~9、14~16、18为首次从该植物中分离得到。
大戟属;泽漆;7-羟基-6-甲氧基香豆素;3-羟基乙酰吲哚;rayalinol;3--β--吡喃葡萄糖基泽漆内酯A;4′,5,7-三羟基异黄酮
泽漆L.为大戟科(Euphorbiaceae)大戟属Linn. 植物,民间称为猫眼草、五凤灵芝、五朵云等,其干燥全草可入药[1]。中药泽漆味辛、苦,性微寒,具有利水消肿、消痰退热、散结杀虫之功效,临床常用于治疗腹水、水肿、肺结核、颈淋巴结核、痰多喘咳及癣疮等疾病[2]。迄今为止,已从泽漆中发现具有萜类、黄酮类及多酚类等结构特征的150余个化学成分。其中,有研究表明假白榄酮型二萜酯类化合物有可能成为抗肿瘤药物的先导化合物[3],黄酮类成分如heliosin具有止咳作用[4]。为进一步发掘泽漆植物化学资源,本实验从泽漆中分离鉴定了23个化学成分,其中,萜类7个、生物碱类4个、黄酮类3个、其他类9个,分别为β-谷甾醇(β-sitosterol,1)、euphoscopin B(2)、对羟基苯乙酮(4- hydroxyacetophenone,3)、euphoscopin F(4)、euphoscopin C(5)、nepehinol(6)、4-羟基-3,5-二甲氧基苯甲醛(4-hydroxy-3,5-dimethoxy- benzaldehyde,7)、antiquorin(8)、1-吲哚-3-甲醛(1-indole-3-carboxaldehyde,9)、7-羟基-6-甲氧基香豆素(7-hydroxy-6-methoxycoumarin,10)、泽漆内酯 A(helioscopinolide A,11)、euphoheliosnoid A(12)、松脂素(pinoresinol,13)、(+)-去氢催吐萝芙木醇 [(+)-dehydrovomifoliol,14]、loliolide(15)、1-(4-羟基-3-甲氧基苯基)-3-羟基丙-1-酮 [1-(4- hydroxy-3-methoxy-phenyl)-3-hydroxypropan-1-one,16]、3-羟基乙酰吲哚 [3-(hydroxyacetyl)indole,17]、橙皮酰胺(aurantiamide,18)、rayalinol(19)、3--β--吡喃葡萄糖基泽漆内酯A(3--β-- glucopyranosylhelioscopinolide A,20)、柚皮素(naringenin,21)、4′,5,7-三羟基异黄酮(4′,5,7- trihydroxyisoflavones,22)、槲皮素(quercetin,23)。化合物10、17、19、20、22为首次从该属植物中分离得到,化合物3、7~9、14~16、18为首次从该植物中分离得到。
Bruker Avance III HD 600 MHz型核磁共振波谱仪(瑞士Bruker科技有限公司),LC-3000型制备高效液相色谱仪(北京创新通恒科技有限公司),Agilent1260型高效液相色谱仪(美国Agilent公司),Sartorius BSA124S型万分之一电子天平(Sartorius(上海)贸易有限公司),薄层色谱硅胶板GF254、柱色谱硅胶100~200、200~300目(均购于青岛海洋化工有限公司),Sephadex LH-20(美国GE Healthcare公司),石油醚、二氯甲烷、醋酸乙酯、丙酮、甲醇(均为分析级,购于西陇化工股份有限公司),甲醇(色谱级,Dikma Technologies. Inc.,),双蒸水为实验室自制。
泽漆于2016年11月购自浙江丽水,经江西中医药大学石强副教授鉴定为大戟科大戟属草本植物泽漆L. 的干燥地上部分,凭证标本(20140523)存于江西中医药大学现代中药制剂教育部重点实验室标本室。
取干燥泽漆药材50.0 kg,加8倍量70%乙醇回流提取3次,每次2 h,滤过,合并滤液,减压回收溶剂,浓缩至无醇味,得浸膏3.9 kg。再加入适量水,制成混悬液,依次用石油醚、二氯甲烷、醋酸乙酯萃取,回收溶剂,得到石油醚萃取部位1.6 kg、二氯甲烷萃取部位992.3 g、醋酸乙酯萃取部位415.0 g。
石油醚萃取部位(1.56 kg)经硅胶柱色谱(100~200目),石油醚-醋酸乙酯(200∶1→1∶20)梯度洗脱,得到12个流分Fr. A~L。Fr. D(33.0 g)经硅胶柱色谱(200~300目),石油醚-丙酮(30∶1)等度洗脱,得5个流分Fr. D.1~D.5。Fr. D.1(5.94 g)经硅胶柱色谱(200~300目),石油醚-醋酸乙酯(50∶1→30∶1)梯度洗脱,得6个流分Fr. D.1.A~D.1.F。Fr. D.1.E(2.07 g)经硅胶柱色谱(200~300目),石油醚-醋酸乙酯(30∶1→20∶1)梯度洗脱,得化合物1(17. 2 mg)和2(39.2 mg)。
二氯甲烷萃取部位(992.3 g)经硅胶柱色谱(100~200目),石油醚-醋酸乙酯(100∶1→1∶50)梯度洗脱得23个流分Fr. A~W。Fr. M(8.0 g)经硅胶柱色谱(100~200目),石油醚-醋酸乙酯(20∶1→1∶2)梯度洗脱得5个流分Fr. M.1~M.5。Fr. M.3(862.0 mg)经硅胶柱色谱(200~300目,石油醚-醋酸乙酯30∶1→5∶1)梯度洗脱,得流分Fr. M.3(13-19)(25.0 mg)。Fr. M.3(13-19)经高效液相[甲醇-水(18∶82)]等度洗脱得化合物3(2.0 mg,R=19.4 min)。Fr. M.3(28-36)经高效液相[甲醇-水(72∶28)]等度洗脱得化合物4(2.0 mg,R=20.9 min)和5(3.0 mg,R=41.3 min)。Fr. O(31.5 g)经硅胶柱色谱(100~200目),二氯甲烷-甲醇(200∶1→5∶1)梯度洗脱得10个流分Fr. O.1~O.10。Fr. O.1(190.0 mg)经Sephadex LH-20凝胶柱色谱[二氯甲烷-甲醇(1∶1)]得化合物6(5.0 mg)。Fr. O.2(244.0 mg)经Sephadex LH-20凝胶柱色谱[二氯甲烷-甲醇(1∶1)]得化合物7(5.0 mg)。Fr. O.3(8.3 g)经硅胶柱色谱(200~300目),石油醚-二氯甲烷(1∶150)等度洗脱,得3个流分Fr. O.3.A~O.3.C。Fr. O.3.A(3.9 g)经硅胶柱色谱(200~300目),石油醚-醋酸乙酯(6∶1)等度洗脱得5个流分Fr. O.3.A.1~O.3.A.5。Fr. O.3.A.2(274.0 mg)经Sephadex LH-20凝胶柱色谱[二氯甲烷-甲醇(1∶1)]得化合物8(5.0 mg)。Fr. O.3.A.3(303.0 mg)经Sephadex LH-20凝胶柱色谱,二氯甲烷-甲醇(1∶1)等度洗脱得化合物9(3.0 mg)。Fr. O.3.A.4(276.0 mg)经Sephadex LH-20凝胶柱色谱,二氯甲烷-甲醇(1∶1)等度洗脱得化合物10(7.0 mg)。Fr. O.3.C(1.4 g)经硅胶柱色谱(200~300目),二氯甲烷-甲醇(300∶1→50∶1)梯度洗脱得4个流分Fr. O.3.C.1~O.3.C.4。Fr. O.3.C.2(950.0 mg)经Sephadex LH-20凝胶柱色谱,二氯甲烷-甲醇(1∶1)等度洗脱得2个流分Fr. O.3.C.2.A~O.3.C.2.B。Fr. O.3.C.2.B(509.0 mg)经Sephadex LH-20凝胶柱色谱[二氯甲烷-甲醇(1∶1)]等度洗脱得化合物11(20.0 mg)。Fr. P(22.5 g)经硅胶柱色谱(200~300目),二氯甲烷-甲醇(100∶0→25∶1)梯度洗脱得3个流分Fr. P.1~P.3。Fr. P.1(3.9 g)经硅胶柱色谱(200~300目),石油醚-醋酸乙酯(6∶1→2∶1)梯度洗脱得8个流分Fr. P.1.A~P.1.H。Fr. P.1.D(1.4 g)经硅胶柱色谱(200~300目),二氯甲烷-甲醇(100∶0→25∶1)梯度洗脱得5个流分Fr. P.1.D.1~P.1.D.5。Fr. P.1.D.4(404.0 mg)经Sephadex LH-20凝胶柱色谱[二氯甲烷-甲醇(1∶1)]等度洗脱得到化合物12(5.0 mg)和13(5.0 mg)。Fr. P.2(2.1 g)经硅胶柱色谱(200~300目),二氯甲烷-甲醇(100∶0→25∶1)梯度洗脱得到6个流分Fr. P.2.A~P.2.F。Fr. P.2.B(871.3 mg)经硅胶柱色谱(200~300目),石油醚-醋酸乙酯(16∶1→1∶1)梯度洗脱得到4个流分Fr. P.2.B.1~P.2.B.4。Fr. P.2.B.2(181.2 mg)经硅胶柱色谱(200~300目),石油醚-醋酸乙酯(15∶1)等度洗脱得2个流分 Fr. P.2.B.2.A~P.2.B.2.B。Fr. P.2.B.2.A(144.6 mg)经高效液相色谱,甲醇-水(20∶80、27∶73)分别等度洗脱得化合物14(8.7 mg,R=38.9 min)和化合物15(39.5 mg,R=48.5 min)。Fr. P.2.B.3(148.2 mg)经Sephadex LH-20凝胶柱色谱[二氯甲烷-甲醇(1∶1)]等度洗脱得化合物16(15.0 mg)和17(2.9 mg)。Fr. Q(7.2 g)经硅胶柱色谱(100~200目),二氯甲烷-甲醇(200∶1→0∶100)梯度洗脱得6个流分Fr. Q.1~Q.6。Fr. Q.3(1.48 g)经硅胶柱色谱(200~300目),石油醚-醋酸乙酯(6∶1→1∶1)梯度洗脱得到流分Fr. Q.3.A~Q.3.D。Fr. Q.3.C经高效液相色谱,甲醇-水(50∶50)等度洗脱,得到化合物18(6.1 mg,R=86.1 min)。Fr. U(20.2 g)经Sephadex LH-20凝胶柱色谱,二氯甲烷-甲醇(1∶1)等度洗脱,得到6个流分Fr. U.1~U.6。Fr. U.1(8.7 g)经硅胶柱色谱(200~300目),二氯甲烷-甲醇(50∶1→2∶1)梯度洗脱,得到流分Fr.U.1(21)(30.0 mg)。Fr. U.1(21)经高效液相色谱,甲醇-水(45∶55)等度洗脱得到化合物19(2.0 mg,R=38.1 min)。Fr. U.2(4.1 g)经硅胶柱色谱(200~300目),二氯甲烷-甲醇(50∶1→2∶1)梯度洗脱得到5个流分Fr. U.2.A~U.2.E。Fr. U.2.C(1.3 g)经硅胶柱色谱(200~300目),二氯甲烷-甲醇(100∶1→5∶1)梯度洗脱得到流分Fr. U.2.C(29-31)(40.0 mg)。Fr. U.2.C(29-31)经高效液相色谱,甲醇-水(48∶52)等度洗脱得到化合物20(4.6 mg,R=56.1 min)。
醋酸乙酯萃取部位(415.0 g)经硅胶柱色谱(100~200目),二氯甲烷-甲醇(100∶0→1∶1)梯度洗脱,得8个流分Fr. A~H。Fr. E(25.0 g)经硅胶柱色谱(100~200目),石油醚-醋酸乙酯(10∶1→1∶20)梯度洗脱得9个流分Fr. E.1~E.9。Fr. E.7(2.79 g)经硅胶柱色谱(200~300目),石油醚-丙酮(10∶1→1∶2)梯度洗脱得到3个流分Fr. E.7.A~E.7.C。Fr. E.7.C(236.8 mg)经高效液相色谱,甲醇-水(42∶58)等度洗脱得化合物21(2.0 mg,R=37.9 min)和22(2.0 mg,R=39.2 min)。Fr. F(6.4 g)经Sephadex LH-20凝胶柱色谱,二氯甲烷-甲醇(1∶1)等度洗脱得到化合物23(40.0 mg)。
化合物1:白色粉末,分子式C29H50O;1H-NMR (600 MHz, CDCl3): 5.39~5.36 (1H, m, H-6), 3.60~3.49 (1H, m, H-3), 1.03 (3H, s, CH3-19), 0.94 (3H, d,= 6.5 Hz, CH3-21), 0.87 (3H, d,= 7.4 Hz, CH3-26), 0.86~0.85 (3H, m, CH3-29), 0.84 (3H, d,= 6.8 Hz, CH3-27), 0.70 (3H, s, CH3-18);13C-NMR (150 MHz, CDCl3): 140.8 (C-5), 121.7 (C-6), 71.8 (C-3), 56.8 (C-14), 56.1 (C-17), 50.1 (C-9), 45.8 (C-24), 42.3 (C-4), 42.3 (C-13), 39.8 (C-12), 37.3 (C-1), 36.5 (C-10), 36.2 (C-20), 34.0 (C-22), 31.9 (C-7), 31.9 (C-8), 31.7 (C-2), 29.2 (C-25), 28.3 (C-16), 26.1 (C-23), 24.3 (C-15), 23.1 (C-28), 21.1 (C-11), 19.8 (C-26), 19.4 (C-19), 19.0 (C-27), 18.8 (C-21), 12.0 (C-29), 11.9 (C-18)。以上数据与文献报道一致[5],故鉴定化合物为β-谷甾醇。
化合物2:白色粉末,易溶于氯仿,分子式C33H42O6;1H-NMR (600 MHz, CDCl3): 7.99 (2H, brd,= 7.0 Hz, H-3′, 7′), 7.53 (1H, t,= 7.4 Hz, H-5′), 7.43 (2H, t,= 7.8 Hz, H-4′,6′), 5.92 (1H, brs, H-14), 5.66 (1H, dd,= 1.5, 8.6 Hz, H-5), 5.38 (1H, dd,= 11.5, 4.5 Hz, H-7), 5.35 (1H, d,= 16.0 Hz, H-11), 5.19 (1H, dd,= 7.4, 3.0 Hz, H-3), 5.16 (1H, dd,= 15.2, 8.0 Hz, H-12), 3.25 (1H, dd,= 8.3, 7.7 Hz, H-4), 3.14 (1H, dd,= 15.8, 11.5 Hz, H-8), 2.97 (1H, dd,= 15.2, 8.0 Hz, H-1), 2.67 (1H, dd,= 15.8, 4.5 Hz, H-8), 2.47~2.41 (1H, m, H-2), 2.22 (3H, s, 15-OCOCH3), 2.19~2.15 (1H, m, H-13), 2.15 (3H, s, 14-OCOCH3), 1.86 (3H, d,= 1.5 Hz, H-17), 1.43 (1H, dd,= 15.2, 9.2 Hz, H-1), 1.26 (3H, s, 7-OCOCH3), 1.23 (3H, s, H-19), 1.09 (3H, s, H-18), 1.09 (3H, d,= 5.0 Hz, H-20), 0.91 (3H, d,= 7.1 Hz, H-16);13C-NMR (150 MHz, CDCl3): 207.5 (C-9), 170.3 (14-OCOCH3), 170.1 (15-OCOCH3), 170.0 (7-OCOCH3), 165.4 (C-1′), 135.8 (C-6), 133.7 (C-11), 133.6 (C-12), 132.8 (C-5′), 130.7 (C-2′), 129.5 (C-3′,7′), 128.3 (C-4′, 6′), 122.6 (C-5), 92.3 (C-15), 83.3 (C-3), 75.3 (C-14), 73.4 (C-7), 49.0 (C-10), 44.2 (C-4), 43.1 (C-1), 42.9 (C-8), 37.7 (C-2), 37.7 (C-13), 25.3 (C-18), 24.9 (C-19), 23.0 (15-OCOCH3), 22.1 (14-OCOCH3), 21.0 (7-OCOCH3), 20.1 (C-20), 18.9 (C-16), 18.9 (C-17)。以上数据与文献报道一致[6],鉴定化合物2为euphoscopin B。
化合物3:淡黄色粉末,易溶于氯仿,分子式C8H8O2;1H-NMR (600 MHz, CDCl3): 9.84 (1H, s, 1-OH), 7.78 (2H, d,= 8.5 Hz, H-3, 5), 6.92 (2H, d,= 8.5 Hz, H-2, 6), 1.22 (3H, s, H-8);13C-NMR (150 MHz, CDCl3): 191.1 (CO), 160.8 (C-1), 132.2 (C-3, 5), 130.2 (C-4), 116.3 (C-2, 6), 29.4 (C-8)。以上数据与文献报道对照基本一致[7],故鉴定化合物3为对羟基苯乙酮。
化合物4:白色粉末,易溶于氯仿,分子式C31H38O6;1H-NMR (600 MHz, CDCl3): 8.04 (2H, dd,= 7.8, 1.2 Hz, H-2′, 6′), 7.54 (1H, dd,= 7.8, 1.2 Hz, H-4′), 7.46 (2H, t,= 7.8 Hz, H-3′, 5′), 5.70 (1H, dd,= 9.1, 1.5 Hz, H-5), 5.53 (1H, d,= 15.5 Hz, H-11), 5.26 (1H, dd,= 11.3, 4.8 Hz, H-7), 5.18 (1H, dd,= 6.7, 2.4 Hz, H-3), 5.03 (1H, dd,= 15.5, 9.4 Hz, H-12), 3.44 (1H, dd,= 9.4, 6.7 Hz, H-4), 3.09 (1H, dd,= 11.0, 7.8 Hz, H-8), 3.07 (1H, m, H-1), 2.69 (1H, dd,= 14.9, 4.8 Hz, H-8), 2.66 (1H, m, H-13), 2.35 (3H, s, 15-OCOCH3), 2.26 (1H, m, H-2), 2.24 (1H, m, H-1), 1.67 (3H, d,= 1.4 Hz, H-17), 1.29 (3H, s, 7-OCOCH3), 1.22 (3H, d,= 3.2 Hz, H-20), 1.21 (3H, s, H-19), 1.14 (3H, d,= 6.6 Hz, H-16), 1.10 (3H, s, H-18);13C-NMR (150 MHz, CDCl3): 211.6 (C-14), 206.6 (C-9), 170.8 (15-OCOCH3), 169.8 (7-OCOCH3), 165.2 (C-7′), 139.9 (C-6), 136.4 (C-11), 133.0 (C-4′), 132.3 (C-12), 130.5 (C-1′), 129.5 (C-2′, 6′), 128.4 (C-3′, 5′), 119.3 (C-5), 95.9 (C-15), 83.4 (C-3), 73.2 (C-7), 51.4 (C-13), 49.3 (C-10), 45.5 (C-4), 43.6 (C-1), 42.5 (C-8), 39.2 (C-2), 25.1 (C-18), 22.0 (C-20), 21.9 (15-OCOCH3), 20.1 (C-19), 19.0 (7-OCOCH3), 18.9 (C-16), 18.7 (C-17)。以上数据与文献报道一致[6],故鉴定化合物4为euphoscopin F。
化合物5:白色粉末,易溶于氯仿,分子式C38H44O9;1H-NMR (600 MHz, CDCl3): 7.85 (2H, d,= 7.1 Hz, H-2′′, 6′′), 7.56 (2H, d,= 8.0 Hz, H-2′, 6′), 7.46 (1H, t,= 7.4 Hz, H-4′′), 7.31 (1H, m, H-4′), 7.28 (2H, t,= 7.7 Hz, H-3′′, 5′′), 6.96 (2H, t,= 7.8 Hz, H-3′, 5′), 5.94 (1H, d,= 0.7 Hz, H-14), 5.86 (1H, d,= 9.8 Hz, H-5), 5.70 (1H, dd,= 11.4, 4.2 Hz, H-3), 5.39 (1H, d,= 16.0 Hz, H-11), 5.21 (1H, dd,= 16.0, 9.0 Hz, H-7), 5.13 (1H, dd,= 6.5, 2.2 Hz, H-12), 3.32 (1H, dd,= 10.9, 6.4 Hz, H-4), 3.29 (1H, dd,= 10.5, 4.6 Hz, H-8a), 2.99 (1H, dd,= 15.5, 8.4 Hz, H-8b), 2.85 (1H, dd,= 15.7, 4.2 Hz, H-1a), 2.45 (1H, m, H-13), 2.20 (3H, s, 15-OCOCH3), 2.17 (3H, s, 14-OCOCH3), 2.13 (1H, m, H-1b), 1.95 (3H, s, H-17), 1.49 (1H, m, H-2), 1.30 (3H, s, H-19), 1.13 (3H, s, H-18), 1.09 (3H, d,= 7.2 Hz, H-20), 0.93 (3H, d,= 7.1 Hz, H-16);13C-NMR (150 MHz, CDCl3): 207.6 (C-9), 170.1 (15-OCOCH3), 170.0 (14-OCOCH3), 165.9 (C-7′′), 165.4 (C-7′), 135.5 (C-6), 133.7 (C-11), 133.6 (C-4′), 132.7 (C-4′′), 132.4 (C-12), 130.4 (C-1′), 129.9 (C-1′′), 129.3 (C-2′, 6′), 129.2 (C-2′′, 6′′), 128.2 (C-3′, 5′), 128.0 (C-3′′, 5′′), 122.7 (C-5), 92.4 (C-15), 84.3 (C-3), 75.6 (C-14), 74.2 (C-7), 49.1 (C-10), 44.0 (C-4), 43.6 (C-1), 42.8 (C-8), 38.0 (C-2), 37.8 (C-13), 25.5 (C-19), 24.9 (C-18), 22.9 (C-20), 22.1 (15-OCOCH3), 21.1 (14-OCOCH3), 19.3 (C-16), 18.9 (C-17)。以上数据与文献报道一致[8],故鉴定化合物5为euphoscopin C。
化合物6:白色粉末,易溶于氯仿,分子式C30H50O;1H-NMR (600 MHz, CDCl3): 4.71 (1H, brs, H-29a), 4.63 (1H, brs, H-29b), 3.19 (1H, dd,= 11.5, 4.7 Hz, H-3), 2.54 (1H, ddd,= 15.6, 9.3, 5.5 Hz, H-19), 1.68 (3H, s, H-30), 1.05(3H, s, H-26), 0.97 (3H, s, H-27), 0.91 (3H, s, H-23), 0.91 (3H, s, H-28), 0.84 (3H, s, H-25), 0.77 (3H, s, H-24);13C-NMR (150 MHz, CDCl3): 150.6 (C-20), 108.9 (C-29), 79.0 (C-3), 55.4 (C-5), 50.6 (C-9), 50.6 (C-18), 44.8 (C-19), 43.1 (C-17), 41.8 (C-14), 41.4 (C-22), 41.0 (C-8), 38.8 (C-4), 37.2 (C-10), 36.9 (C-1), 34.8 (C-13), 34.2 (C-7), 30.6 (C-16), 29.7 (C-21), 28.0 (C-23), 27.6 (C-2), 27.4 (C-15), 25.2 (C-12), 25.1 (C-28), 20.9 (C-11), 20.6 (C-30), 18.4 (C-6), 16.1 (C-25), 16.0 (C-26), 15.4 (C-24), 14.4 (C-27)。以上数据与文献报道一致[9],故鉴定化合物6为nepehinol。
化合物7:淡黄色粉末,易溶于氯仿,分子式C9H10O4;1H-NMR (600 MHz, CDCl3): 9.82 (1H, s, H-7), 7.15 (2H, s, H-2, 6), 3.97 (6H, s, 2×OCH3);13C-NMR (150 MHz, CDCl3): 190.8 (C=O, C-7), 147.4×2 (C-3, 5), 140.8 (C-4), 128.4 (C-1), 106.7 (C-2, 6), 56.5 (2×OCH3)。以上数据与文献报道一致[10],故鉴定化合物7为4-羟基-3,5-二甲氧基苯甲醛。
化合物8:淡黄色粉末,易溶于氯仿,分子式C20H28O3;1H-NMR (600 MHz, CDCl3): 5.04 (1H, brs, H-17), 4.89 (1H, brs, H-17′), 3.90 (1H, d,= 3.0 Hz, H-13), 2.84 (1H, dt,= 3.8, 2.8 Hz, H-12), 2.57(1H, ddd,= 15.9, 13.2, 6.4 Hz, H-2), 2.44 (1H, dt,= 13.6, 3.4 Hz, H-7), 2.39~2.35 (1H, m, H-2′), 2.37~2.34 (1H, m, H-15), 2.04 (1H, ddd,= 14.1, 11.6, 3.8 Hz, H-11), 1.89 (1H, ddd,= 13.4, 6.5, 3.2 Hz, H-1), 1.78 (1H, ddd,= 14.1, 6.2, 2.5 Hz, H-11′), 1.68 (1H, dd,= 11.5, 6.2 Hz, H-9), 1.55~1.50 ( 2H, m, H-2~6), 1.42(1H, dt,= 13.3, 5.5 Hz, H′-1), 1.35~1.26 (2H, m, H-5, 15′), 1.11 (3H, s, CH3-4α), 1.03 (3H, s, CH3-4β), 0.99~0.95 (1H, m, H-7′), 0.87 (3H, s, CH3-10);13C-NMR (150 MHz, CDCl3): 218.0 (C-14), 216.1 (C-3), 142.2 (C-16), 111.1 (C-17), 75.1 (C-13), 55.2 (C-5), 51.1 (C-9), 47.5 (C-8), 47.3 (C-4), 44.8 (C-12), 43.7 (C-15), 37.6 (C-10), 36.7 (C-1), 34.1 (C-2), 30.4 (C-7), 26.2 (CH3-4α), 25.3 (C-11), 21.9 (CH3-4β), 20.0 (C-6), 13.7 (CH3-10)。以上数据与文献报道一致[11],故鉴定化合物8为古柯碱。
化合物9:白色粉末,分子式C9H7NO;1H-NMR (600 MHz, CD3OD): 9.86 (1H, s, 3-CHO), 8.14 (1H, d,= 7.7 Hz, H-4), 8.07 (1H, s, H-2), 7.45 (1H, d,= 8.0 Hz, H-7), 7.25 (1H, t,= 7.5 Hz, H-5), 7.21 (1H, t,= 7.5 Hz, H-6);13C-NMR (150 MHz, CD3OD): 186.0 (3-CHO), 138.3 (C-7a), 137.5 (C-2), 124.3 (C-3a), 123.6 (C-6), 122.2 (C-5), 121.0 (C-4), 118.7 (C-3), 111.7 (C-7)。以上数据与文献报道一致[12],故鉴定化合物9为1-吲哚-3-甲醛。
化合物10:白色粉末,易溶于氯仿,分子式C10H8O4;1H-NMR (600 MHz, CDCl3): 7.62 (1H, d,= 9.6 Hz, H-4), 6.94 (1H, s, H-5), 6.87 (1H, s, H-8), 6.29 (1H, d,= 9.4 Hz, H-3), 6.19 (1H, s, OH), 3.98 (3H, s, OCH3);13C-NMR (150 MHz, CDCl3): 161.6 (C-2), 150.4 (C-7), 149.8 (C-9), 144.1 (C-6), 143.4 (C-4), 113.6 (C-10), 111.6 (C-5), 107.6 (C-3), 103.3 (C-8), 56.6 (OCH3)。以上数据与文献报道一致[13],故鉴定化合物10为7-羟基-6-甲氧基香豆素。
化合物11:白色粉末, 易溶于氯仿,分子式C20H28O3;1H-NMR (600 MHz, CDCl3): 6.29 (1H, s, H-14), 4.87 (1H, dd,= 13.4, 6.2 Hz, H-12), 3.29 (1H, dd,= 8.0, 3.7 Hz, H-3), 2.59~2.54 (1H, m, H-11eq), 2.54~2.50 (1H, m, H-7eq), 2.25~2.19 (1H, m, H-7ax), 2.20~2.14 (1H, m, H-9), 2.00~1.94 (1H, m, H-1eq), 1.90~1.85 (1H, m, H-6eq), 1.84 (3H, s, H-20), 1.80~1.74 (1H, m, H-2eq), 1.68~1.61 (1H, m, H-2ax), 1.56~1.49 (1H, m, H-11ax), 1.49~1.42 (1H, m, H-6ax), 1.30~1.23 (1H, m, H-1ax), 1.20~1.14 (1H, m, H-5), 1.05 (3H, s, H-17), 0.94 ( 3H, s, H-19), 0.84 (3H, s, H-18);13C-NMR (150 MHz, CDCl3): 175.3 (C-16), 156.0 (C-13), 151.4 (C-8), 116.6 (C-15), 114.2 (C-14), 78.6 (C-3), 75.9 (C-12), 54.4 (C-5), 51.6 (C-9), 41.2 (C-10), 39.1 (C-4), 37.4 (C-1), 37.0 (C-7), 28.7 (C-17), 27.6 (C-2), 27.6 (C-11), 23.5 (C-6), 16.7 (C-19), 15.6 (C-18), 8.3 (C-20)。以上数据与文献报道一致[14],故鉴定化合物11为泽漆内酯A。
化合物12:白色粉末,易溶于氯仿,分子式C37H43NO9;1H-NMR (600 MHz, CDCl3): 8.86 (1H, d,= 1.6 Hz, H-3′′), 8.55 (1H, dd,= 4.8, 1.6 Hz, H-5′′), 7.75 (2H, d,= 7.0 Hz, H-3′, 7′), 7.73 (1H, m, H-7′′), 7.40 (1H, t,= 7.4 Hz, H-5′), 7.22 (2H, t,= 7.8 Hz, H-4′, 6′), 6.90 (1H, dd,= 7.9, 4.8 Hz, H-6′′), 5.97 (1H, s, H-14), 5.82 (1H, dd,= 8.7, 1.4 Hz, H-5), 5.65 (1H, dd,= 11.5, 4.4 Hz, H-7), 5.42 (1H, d,= 16.0 Hz, H-11), 5.23 (1H, dd,= 16.0, 8.9 Hz, H-12), 5.16 (1H, dd,= 6.7, 2.6 Hz, H-3), 3.37 (1H, dd,= 15.6, 11.5 Hz, H-8α), 3.32 (1H, dd,= 8.6, 6.9 Hz, H-4), 2.99 (1H, dd,= 15.5, 8.3 Hz, H-1α), 2.85 (1H, dd,= 15.6, 4.3 Hz, H-8β), 2.46 (1H, m, H-13), 2.23 (3H, s, H-15-OCOCH3), 2.19 (3H, s, 14-OCOCH3), 2.14 (1H, m, H-2), 2.00 (3H, d,= 1.3 Hz, H-17), 1.50 (1H, dd,= 15.5, 8.0 Hz, H-1β), 1.33 (3H, s, H-19), 1.15 (3H, s, H-18), 1.08 (3H, d,= 7.2 Hz, H-16), 0.95 (3H, d,= 7.1 Hz, H-20);13C-NMR (150 MHz, CDCl3): 207.5 (C-9), 170.1 (14-OCOCH3), 170.1 (15-OCOCH3), 165.4 (C-1′), 164.4 (C-1′′), 152.9 (C-5′′), 150.6 (C-3′′), 136.6 (C-7′′), 136.0 (C-6), 133.8 (C-11), 133.8 (C-12), 132.8 (C-5′), 130.2 (C-2′), 129.2 (C-3′, 7′), 128.3 (C-4′, 6′), 125.9 (C-2′′), 123.0 (C-5), 123.0 (C-6′′), 92.4 (C-15), 84.1 (C-3), 75.6 (C-14), 75.0 (C-7), 49.3 (C-10), 44.1 (C-4), 43.6 (C-1α, 1β), 43.1 (C-8α, 8β), 38.0 (C-13), 37.8 (C-2), 25.4 (C-18), 25.1 (C-19), 23.1 (C-20), 22.2 (15-OCOCH3), 21.2 (14-OCOCH3), 19.3 (C-16), 19.0 (C-17)。以上数据与文献报道一致[15],故鉴定化合物12为euphoheliosnoid A。
化合物13:白色粉末,易溶于氯仿,分子式C20H22O6;1H-NMR (600 MHz, CDCl3): 6.88 (2H, d,= 2.1 Hz, H-2, 2′), 6.87 (2H, d,= 8.2 Hz, H-5, 5′), 6.81 (2H, dd,= 8.1, 1.8 Hz, H-6, 6′), 4.72 (2H, d,= 4.3 Hz, H-7, 7′), 4.23 (2H, dd,= 9.1, 6.9 Hz, H-9e, 9′e), 3.89 (6H, s, 2×OCH3), 3.86 (2H, dd,= 9.2, 3.7 Hz, H-9a, 9′a), 3.09 (2H, m, H-8, 8′);13C-NMR (151 MHz, CDCl3): 146.5 (C-3, 3′), 145.1 (C-4, 4′), 132.4 (C-1, 1′), 118.6 (C-6, 6′), 114.2 (C-5, 5′), 108.8 (C-2, 2′), 84.9 (C-7, 7′), 71.7 (C-9, 9′), 55.5 (2×OCH3), 53.2 (C-8, 8′)。以上数据与文献报道一致[16],故鉴定化合物13为松脂素。
化合物14:淡黄色粉末,易溶于甲醇,分子式C13H18O3;1H-NMR (600 MHz, CH3OD): 6.97 (1H, d,= 16.9 Hz, H-7), 6.41 (1H, d,= 15.8 Hz, H-8), 5.94~5.90 (1H, m, H-4), 2.58 (1H, d,= 17.3 Hz, H-2a), 2.28 (1H, s, 10-CH3), 2.25 (1H, d,= 16.0 Hz, H-2b), 1.88 (3H, d,= 4.6 Hz, 13-CH3), 1.04 (3H, s, 11-CH3), 0.99 (3H, s, 12-CH3)。13C-NMR (150 MHz, CH3OD): 199.3 (C-9), 199.0 (C-3), 163.1 (C-5), 146.6 (C-7), 130.5 (C-8), 126.4 (C-4), 78.9 (C-6), 49.1 (C-2), 41.1 (C-1), 26.3 (C-10), 23.8 (C-11), 22.2 (C-12), 17.7 (C-13)。以上数据与文献对照一致[17],故鉴定化合物14为(+)-去氢催吐萝芙木醇。
化合物15:淡黄色粉末,易溶于甲醇,分子式C11H16O3;1H-NMR (600 MHz, CD3OD): 5.74 (1H, s, H-7), 4.28~4.15 (1H, m, H-3), 2.46~2.37 (1H, m, H-4a), 2.02~1.94 (1H, m, H-2a), 1.75 (3H, s, H-11), 1.73 (1H, d,= 4.0 Hz, H-2b), 1.52 (1H, dd,= 14.4, 3.7 Hz, H-4b), 1.45 (3H, s, H-9), 1.26 (3H, s, H-10);13C-NMR (150 MHz, CD3OD)185.8 (C-6), 174.6 (C-8), 113.5 (C-7), 89.1(C-5), 67.4 (C-3), 48.1 (C-4), 46.6 (C-2), 37.7 (C-1), 31.2 (C-11), 27.6 (C-10), 27.1 (C-9)。以上数据与文献报道一致[18],故鉴定化合物15为loliolide。
化合物16:淡黄色固体,易溶于氯仿,分子式C10H12O4;1H-NMR (600 MHz, CDCl3): 7.54 (1H, dd,= 8.2, 1.9 Hz, H-6), 7.53 (1H, d,= 1.8 Hz, H-2), 6.95 (1H, d,= 8.1 Hz, H-5), 6.23 (1H, s, 4-OH), 4.02 (2H, dt,= 5.1 Hz, H-9), 3.95 (3H, s, OCH3), 3.18 (2H, t,= 5.3 Hz, H-8), 2.80 (1H, s, 9-OH);13C-NMR (150 MHz, CDCl3): 199.5 (C-7), 151.2 (C-4), 147.1 (C-3), 130.0 (C-1), 124.0 (C-6), 114.3 (C-5), 109.9 (C-2), 58.7 (C-9), 56.4 (OCH3), 40.1 (C-8)。以上数据与文献报道一致[19],故鉴定化合物16为1-(4-羟基-3-甲氧基苯基)-3-羟基丙-1-酮。
化合物17:灰色粉末,易溶于氯仿,分子式C10H9O2N;1H-NMR (600 MHz, CDCl3): 8.31~8.26 (1H, m, H-4), 7.93 (1H, d,= 3.1 Hz, H-2), 7.48~7.45 (1H, m, H-7), 7.38~7.32 (2H, m, H-5, 6), 4.79 (2H, s, CH2OH);13C-NMR (150 MHz, CDCl3): 193.1 (C=O), 136.1 (C-7a), 130.5 (C-2), 124.9 (C-3a), 124.1(C-4), 123.1 (C-5), 121.9 (C-6), 114.2 (C-3), 111.6 (C-7), 65.3 (CH2OH)。以上数据与文献报道一致[20],故鉴定化合物17为化合物3-羟基乙酰吲哚。
化合物18:白色粉末,易溶于甲醇,分子式C25H26N2O3;1H-NMR (600 MHz, CD3OD): 7.68 (2H, d,= 9.4 Hz, H-3′, 7′), 7.52 (1H, t,= 7.4 Hz, H-5′), 7.42 (2H, t,= 7.7 Hz, H-4′, 6′), 7.28~7.19 (5H, m, H-5~9), 7.19~7.16 (2H, m, H-5′′, 7′′), 7.13 (2H, d,= 7.8 Hz, H-4′′, 8′′), 7.06 (1H, t,= 7.3 Hz, H-6′′), 4.78 (1H, dd,= 9.0, 6.1 Hz, H-2), 4.09~4.03 (1H, m, H-1′′), 3.50~3.35(2H, m, H-9′′), 3.14 (1H, dd,= 13.8, 6.1 Hz, H-3), 2.97 (1H, dd,= 13.8, 9.0 Hz, H-3), 2.90 (1H, dd,= 13.7, 6.0 Hz, H-2′′), 2.70 (1H, dd,= 13.7, 8.2 Hz, H-2′′);13C-NMR (150 MHz, CD3OD): 173.0 (C-1), 169.7 (C-1′), 139.3 (C-4), 138.4 (C-3′′), 135.0 (C-2′), 132.6 (C-5′), 130.1 (C-6, 8), 130.1 (C-5′′, 7′′), 129.2 (C-4′′, 8′′), 129.1 (C-5, 9), 129.0 (C-3′, 7′), 128.2 (C-7), 127.5 (C-4′, 6′), 127.0 (C-6′′), 63.6 (C-9′′), 56.4 (C-2), 53.9 (C-1′′), 38.5 (C-3), 37.6 (C-2′′)。以上数据与文献报道一致[21],故鉴定化合物18为橙皮酰胺。
化合物19:白色粉末,易溶于氯仿,分子式C22H26O8;1H-NMR (600 MHz, CDCl3): 6.96 (1H, brs, H-2), 6.86 (1H, d,= 8.1 Hz, H-5), 6.73 (1H, dd,= 8.2, 1.7 Hz, H-6), 6.63 (2H, s, H-2′, 6′), 4.99 (1H, brs, H-9), 4.79 (1H, brs, H-7′), 4.34 (1H, dd,= 6.7, 4.8 Hz, H-9′a), 4.13 (1H, brs, H-7), 3.97 (1H, dd,= 9.3, 2.4 Hz, H-9′b), 3.92 (1H, dd,= 6.7, 3.4 Hz, Ha-9a), 3.90 (9H, s, OCH3×3), 3.47 (1H, dd,= 12.1, 9.2 Hz, Hb-9a), 3.14 (1H, brs, H-8′), 3.09 (1H, brs, H-8);13C-NMR (150 MHz, CDCl3): 153.5 (C-5′), 146.6 (C-3), 144.8 (C-4), 137.6 (C-4′), 134.3 (C-1), 131.2 (C-1′), 118.7 (C-6), 114.1 (C-5), 108.3 (C-2), 102.8 (C-2′), 102.7 (C-6′), 87.0 (C-7), 85.6 (C-7′), 72.5 (C-9), 72.0 (C-9′), 60.6 (C-9a), 56.3 (2×OCH3), 56.0 (OCH3), 54.5(C-8), 54.4 (C-8′), 53.5 (C-3′)。以上数据与文献报道一致[22],故鉴定化合物19为rayalinol。
化合物20:白色粉末,易溶于甲醇,分子式C26H38O8;1H-NMR (600 MHz, CD3OD): 6.38 (1H, s, H-14), 4.96 (1H, dd,= 13.6, 6.1 Hz, H-12), 4.32 (1H, d,= 7.8 Hz, H-1′), 3.84 (1H, dd,= 11.7, 2.2 Hz, H-6′β), 3.65 (1H, dd,= 11.8, 5.7 Hz, H-6′α), 3.40 (1H, dd,= 11.9, 4.2 Hz, H-3), 3.35 (1H, t,= 9.0 Hz, H-3′), 3.27~3.23 (1H, m, H-4′), 3.23~3.20 (1H, m, H-5′), 3.17~3.12 (1H, m, H-2′), 2.59 (1H, d,= 13.4, 6.3 Hz, H-11β), 2.56~2.52 (1H, m, H-7β), 2.30~2.25 (1H, m, H-7α), 2.25~2.19 (1H, m, H-9), 2.04~1.98 (1H, m, H-1β), 1.90~1.87 (1H, m, H-6β), 1.87~1.84 (1H, m, H-2β), 1.78 (3H, s, H-17), 1.69~1.62 (1H, m, H-2α), 1.52~1.47 (1H, m, H-6α), 1.47~1.44 (1H, m, H-11α), 1.34-1.28 (1H, m, H-1α), 1.23~1.20 (1H, m, H-5), 1.06 (3H, s, H-18), 0.97 (3H, s, H-20), 0.85 (3H, s, H-19);13C-NMR (150 MHz, CH3OD): 176.3 (C-16), 157.6 (C-13), 152.9 (C-8), 115.5 (C-15), 113.4 (C-14), 100.5 (C-1′), 84.1 (C-3), 76.8 (C-3′), 76.5 (C-5′), 76.4 (C-12), 73.7 (C-2′), 70.5 (C-4′), 61.6 (C-6′), 54.6 (C-5), 51.4 (C-9), 40.9 (C-10), 38.1 (C-4), 36.9 (C-1), 36.5 (C-7), 27.9 (C-18), 27.3 (C-11), 23.3 (C-6), 23.1 (C-2), 15.7 (C-19), 15.7 (C-20), 6.7 (C-17)。以上数据与文献报道一致[23],故鉴定化合物20为3--β--吡喃葡萄糖基泽漆内酯A。
化合物21:白色粉末,易溶于甲醇,分子式C15H12O5;1H-NMR (600 MHz, CD3OD): 7.30 (2H, d,= 8.4 Hz, H-2′, 6′), 6.80 (2H, d,= 8.6 Hz, H-3′, 5′), 5.86~5.87 (2H, d,= 2.2 Hz, H-6, 8), 5.33 (1H, dd,= 12.9, 3.0 Hz H-2a), 3.10 (1H, dd,= 17.1, 13.0 Hz, H-3a), 2.68 (1H, dd,= 17.0, 2.9 Hz, H-3e);13C-NMR (150 MHz, CH3OD): 196.3 (C-4), 167.4 (C-7), 164.1 (C-5), 163.6 (C-9), 157.6 (C-4′), 129.7 (C-1′), 127.7 (C-2′, 6′), 114.9 (C-3′, 5′), 101.7 (C-10), 95.8 (C-8), 94.9 (C-6), 79.1 (C-2), 42.6 (C-3)。以上数据与文献报道一致[24],故鉴定化合物21为柚皮素。
化合物22:白色粉末,易溶于甲醇,分子式C15H10O5;1H-NMR (600 MHz, CD3OD): 8.04 (1H, s, H-2), 7.36 (2H, d,= 8.7 Hz, H-2′, 6′), 6.83 (2H, d,= 8.7 Hz, H-3′, 5′), 6.32 (1H, d,= 2.2 Hz, H-8), 6.20 (1H, d,= 2.1 Hz, H-6);13C-NMR (150 MHz, CD3OD): 181.1 (C-4), 163.9 (C-7), 162.8 (C-5), 158.4 (C-8a), 157.5 (C-4′), 153.4 (C-2), 129.8 (C-2′, 6′), 123.4 (C-3), 122.1 (C-1′), 114.7 (C-3′, 5′), 104.9 (C-4a), 98.8 (C-6), 93.4 (C-8)。以上数据与文献对照一致[25],故鉴定化合物22为4′,5,7-三羟基异黄酮。
化合物23:黄色粉末,易溶于甲醇,分子式C15H10O7;1H-NMR (600 MHz, CD3OD): 7.75 (1H, d,= 2.2 Hz, H-2′), 7.65 (1H, dd,= 8.5, 2.2 Hz, H-6′), 6.90 (1H, d,= 8.5 Hz, H-5′), 6.41 (1H, d,= 2.1 Hz, H-8), 6.20 (1H, d,= 2.1 Hz, H-6);13C-NMR (150 MHz, CD3OD): 175.9 (C-4), 161.1 (C-5), 156.8 (C-9), 147.4 (C-4′), 146.6 (C-2), 144.8 (C-3′), 135.8 (C-3), 122.7 (C-1′), 120.3 (C-6′), 114.8 (C-5′), 114.6 (C-2′), 103.1 (C-10), 93.0 (C-8), 64.2 (C-7), 7.8 (C-6)。以上数据与文献报道一致[26],故鉴定化合物23为槲皮素。
利益冲突 所有作者均声明不存在利益冲突
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Chemical constituents of
ZHA Xian-jin1, SHI Qiang2,SHAO Feng1,ZHANG Pu-zhao1,LIU Rong-hua1,YANG Ming1,RAO Qian-ru1
1. Key Laboratory of Modern Preparation of TCM, Ministry of Education, JiangxiUniversity of Traditional Chinese Medicine, Nanchang 330004, China 2. Qihuang Academy of Traditional Chinese Medicine, Jiangxi University of Traditional Chinese Medicine, Nanchang 330004, China
To study the chemical constituents of.The compounds were isolated and purified by silica gel, SephadexLH-20 column chromatography and preparative HPLC, and their structures wereidentified by analysis of physicochemical properties and spectroscopic evidences.Twenty-three compounds were isolated from the 70% EtOH extract of. Their structures were identified as β-sitosterol (1), euphoscopin B (2), 4-hydroxyacetophenone(3), euphoscopin F(4), euphoscopin C(5), nepehinol(6), 4-hydroxy-3,5-dimethoxybenzaldehyde (7), antiquorin (8), 1-indole-3-carboxaldehyde (9), 7-hydroxy-6-methoxycoumarin (10), helioscopinolide A (11), euphoheliosnoid A(12), pinoresinol (13), (+)-dehydrovomifoliol (14), loliolide(15), 1-(4-hydroxy-3-methoxy-phenyl)-3-hydroxypropan-1-one(16), 3-(hydroxyacetyl)indole (17), aurantiamide (18), rayalinol(19), 3--β--glucopyranosylhelioscopinolide A(20), naringenin(21), 4′,5,7-trihydroxyisoflavones(22) and quercetin(23).Compounds 10,17,19, 20,22 are isolated fromgenus for the first time, 3, 7—9,14—16,18 are isolated fromfor the first time.
Linn.;L.; 7-hydroxy-6-methoxycoumarin; 3-(hydroxyacetyl)indole;rayalinol; 3--β--glucopyranosylhelioscopinolideA; 4′,5,7-trihydroxy isoflavones
R284.1
A
0253 - 2670(2021)02 - 0341 -08
10.7501/j.issn.0253-2670.2021.02.006
2020-05-12
国家自然科学基金资助项目(82060698);国家自然科学基金资助项目(81560637);江西省自然科学基金资助项目(20161BAB205216)
查显进(1994—),男,硕士,研究方向为中药活性成分与质量评价。E-mail: 724543064@qq.com
邵 峰(1980—),男,副教授,硕士生导师,主要从事中药活性成分与质量评价研究。E-mail: shaofeng0729@163.com
[责任编辑 王文倩]