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台湾狗牙花的生物碱类化学成分

  • 谢静 1,2
  • 范春林 1,2
  • 徐杰 1,2
  • 张建 1,2
  • 叶文才 1,2,3
  • 张晓琦 1,2,3
1. 暨南大学药学院中药及天然药物研究所,广州 510632; 2. 暨南大学广东省现代中药工程技术研究中心,广州 510632; 3. 国家药品监督管理局中成药质量评价重点实验室,广州 510632

中图分类号: R284.1

最近更新:2021-06-28

DOI:10.11665/j.issn.1000-5048.20210304

  • 全文
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  • 参考文献
  • 作者
  • 出版信息
目录contents

摘要

采用硅胶、Sephadex LH-20、ODS、HPLC等色谱方法进行分离纯化,从夹竹桃科植物台湾狗牙花(Ervatamia pandacaqui Pichon)枝叶中分离得到11个生物碱类化合物,根据其理化性质与波谱数据分别鉴定为voacristine 7-hydroxyindolenine(1),iboxygaine (2),19S-hydroxyibogamine (3),3-oxotabersonine (4),派利文碱(perivine,5),佩西立文(pericyclivine,6),rhazinalinol (7),geissoschizol (8),3,14-dihydroolivacine (9),瓦莱萨明碱(vallesamine,10),conolobine A(11)。化合物1 ~ 11均为首次从该植物中分离得到。

台湾狗牙花(Ervatamia pandacaqui Pichon)为夹竹桃科(Apocynaceae)狗牙花属植物,原产于菲律宾,主要栽培于我国台湾省台南市及广东省南部岛屿;具有清热降压和消肿解毒的作用,常用于治疗高血压、咽喉肿痛、痈疽疮毒、跌打损伤等;其化学成分研究较

1。狗牙花属植物约有120种,主要分布于从印度起经中国西南部、越南、缅甸、泰国、马来西亚、印度尼西亚、菲律宾到澳大利亚地区;我国产狗牙花主要有15个种和5个变种,分布于西南到华南及台湾省等地2。狗牙花属植物中富含的生物碱结构复杂多变,生物活性显著,本课题组前期系统地对该属植物药用狗牙花、海南狗牙花和台湾狗牙花中的生物碱类成分进行研究,从中发现了一系列具有新颖骨架且生物活性好的化合3-8。本研究又从台湾狗牙花枝叶中分离得到11个生物碱类化合物,分别鉴定为:voacristine 7-hydroxyindolenine(1), iboxygaine(2), 19S-hydroxyibogamine(3), 3-oxotabersonine(4), 派利文碱(perivine, 5),佩西立文(pericyclivine,6),rhazinalinol(7),geissoschizol(8),3,14-dihydroolivacine(9),瓦莱萨明碱(vallesamine,10),conolobine A(11)。所有化合物均为首次从该植物中分离得到。

1 仪器与材料

V-550型紫外-可见光谱仪,FT/IR-480 Plus Fourier Transform型红外光谱仪(日本Jasco公司); Advantage Max质谱仪(美国Thermo Finnigan公司); 6210 ESI/TOF质谱仪,1200分析及制备型高效液相色谱仪(美国安捷伦公司); AV-400型超导核磁共振仪(美国Bruker公司)。

柱色谱用硅胶(100 ~ 200目、200 ~ 300目,青岛海洋化工厂);RP18柱色谱填料(C18,10 ~ 40 μm,德国Merck公司);Sephadex LH-20(美国Pharmacia公司)。所用试剂均为分析纯或化学纯。

台湾狗牙花植物于2015年9月采集于台湾省台南市,经香港科技大学董婷霞博士鉴定为台湾狗牙花(Ervatamia pandacaqui Pichon)的干燥枝叶。标本(No.CP2015091001)存放于暨南大学药学院植物标本室。

2 提取与分离

台湾狗牙花枝叶5.0 kg,粉碎成粗粉,用95%乙醇渗滤提取3次,减压浓缩后得到总浸膏450 g,加水混悬后,用10% HCl调pH至2 ~ 3后,氯仿萃取,酸水层用氨水调pH至9 ~ 10,萃取液减压浓缩得到粗总生物碱12.5 g。粗总生物碱部位通过硅胶柱色谱(石油醚-丙酮,100∶0→0∶100)得到10个馏分(Fr.1 ~ 10)。Fr.5经Sephadex LH-20柱色谱(氯仿-甲醇,1∶1)得到Fr.5A ~ 5C;Fr.5B经ODS反相柱色谱、 Sephadex LH-20柱色谱(甲醇)以及制备型HPLC纯化得到化合物1[16 mg,乙腈-水(30∶70),tR = 25.0 min]、化合物2[23 mg,乙腈-水(32∶68),tR = 18.0 min]、化合物3[19 mg,乙腈-水(35∶70),tR = 15.0 min]。Fr.7经Sephadex LH-20柱色谱(氯仿-甲醇,1∶1)得到Fr.7A ~ 7C;Fr.7B经ODS反相柱色谱、 Sephadex LH-20柱色谱(甲醇)以及制备型HPLC纯化得到化合物8[21 mg,乙腈-水(50∶50),tR = 27.0 min]、化合物9[27 mg,乙腈-水(47∶53),tR = 23.0 min]、化合物11[18 mg,乙腈-水(42∶58),tR = 28.0 min]。Fr.9经Sephadex LH-20柱色谱(氯仿-甲醇,1∶1)得到Fr.9A ~ 9E;Fr.9C经ODS反相柱色谱、Sephadex LH-20柱色谱(甲醇)以及制备型HPLC纯化得到化合物4[25 mg,乙腈-水(35∶65),tR = 29.0 min]、化合物5[28 mg,乙腈-水(30∶70),tR = 27.0 min]、化合物6[17 mg,乙腈-水(28∶70),tR = 25.0 min]。Fr.10经Sephadex LH-20柱色谱(氯仿-甲醇,1∶1)得到Fr.10A ~ 10C;Fr.10B经ODS反相柱色谱、Sephadex LH-20柱色谱(甲醇)以及制备型HPLC纯化得到化合物7[23 mg,乙腈-水(35∶70),tR = 20.0 min]、化合物10[18 mg,乙腈-水(40∶70),tR = 16.0 min]。

3 结构鉴定

化合物1 黄色粉末,改良碘化铋钾反应呈阳性。UV λMaxMeOH:207,228,291 nm;IR(KBr):3 423,3 263,1 734,1 541,1 474 cm-1;ESI-MS m/z:401.5[M+H+1H NMR(CD3OD,400 MHz) δ:7.30(1H,d,J = 8.4 Hz,H-12) 6.97(1H,d,J = 2.4 Hz,H-9),6.88(1H,dd,J = 8.4,2.4 Hz,H-11),4.30(1H,s,H-21) 4.03(1H,m,H-19a),3.83(3H,s,OMe),3.68(3H,s,COOMe),3.58(1H,m,H-5α),2.96(1H,m,H-5β),2.90(1H,m,H-3a),2.84(1H,m,H-3b),2.83(1H,d,J = 13.8,H-17α),2.26(1H,m,H-6β),2.00(1H,m,H-17β),1.90(1H,m,H-14),1.65(1H,m,H-6α),1.75(1H,m,H-15α),1.50(1H,m,H-15β),1.50(1H,m,H-20),1.12(3H,d,J = 6.3,H-18)13C NMR(CD3OD,100 MHz) δ:189.5(C-2),173.7(COOMe),161.0(C-10),145.6(C-8),145.6(C-13),121.7(C-12),114.8(C-11),109.5(C-9),88.5(C-7),72.7(C-19),58.7(C-21),58.2(C-16),56.2(OMe),53.4(COOMe),49.9(C-5),48.9(C-3),40.8(C-20),38.2(C-6),34.3(C-17),28.1(C-14),25.2(C-15),20.7(C-18)。综上所述,化合物数据与文献[

9]报道一致,故鉴定化合物1为voacristine 7-hydroxyindolenine。

Figure 1 Chemical structures of compounds 1–11

化合物2 白色粉末,改良碘化铋钾反应呈阳性。UV λMaxMeOH:207,227,287 nm;IR(KBr):3 399,3 234,2 922,1 487,1 455,1 215,823 cm-1;ESI-MS m/z 327.3[M+H+1H NMR(CD3OD,400 MHz) δ:7.11(1H,d,J = 8.4 Hz,H-12),6.90(1H,d,J = 2.4 Hz,H-9),6.69(1H,dd,J = 8.4,2.4 Hz,H-11),4.15(1H,m,H-19),3.824(3H,s,OMe),3.35(2H,m,H-5),3.18(1H,m,H-6β),3.17(1H,m,H-16),3.11(1H,m,H-3a),3.11(1H,m,H-6α),3.11(1H,s,H-21),2.97(1H,m,H-3b),2.71(1H,dd,J = 14.6 Hz,3.6 Hz,H-17α),2.15(1H,m,H-17β),1.98(1H,m,H-14),1.91(1H,m,H-15α),1.74(1H,m,H-15β),1.66(1H,m,H-20),1.14(3H,d,J = 6.4 Hz,H-18)13C NMR(CD3OD,100 MHz) δ:154.9(C-10),143.5(C-2),131.8(C-13),131.1(C-8),111.9(C-12),111.4(C-11),108.3(C-7),101.1(C-9),73.2(C-19),61.9(C-21),56.4(OMe),54.2(C-5),50.4(C-3),43.6(C-20),41.1(C-16),35.4(C-17),27.5(C-14),24.6(C-15),21.2(C-6),20.3(C-18)。综上所述,化合物数据与文献[

10]报道一致,故鉴定化合物2为iboxygaine。

化合物3 黄色粉末,改良碘化铋钾反应呈阳性。[α]D25 -21.0°(c 0.16,CHCl3);UV λMaxMeOH:205,226,282 nm;IR(KBr):3 399,3 264,2 926,1 541,1 456,1 155,742 cm-1;ESI-MS m/z 297.4[M+H+1H NMR(CD3OD,400 MHz) δ:7.39(1H,d,J = 7.7 Hz,H-9),7.22(1H,d,J = 7.7 Hz,H-12),7.02(1H,t,J = 7.7 Hz,H-11),6.96(1H,t,J = 7.7 Hz,H-10),4.16(1H,m,H-19),3.36(1H,s,H-21),3.33(2H,m,H-5),3.16(1H,m,H-16),3.15(1H,m,H-6β),3.12(1H,m,H-3a),3.12(1H,m,H-6α),2.96(1H,m,H-3b),2.75(1H,m,H-17α),2.15(1H,m,H-17β),1.98(1H,m,H-14),1.91(1H,m,H-15α),1.76(1H,m,H-15β),1.65(1H,m,H-20),1.14(3H,d,J = 6.4 Hz,H-18)13C NMR(CD3OD,100 MHz) δ:142.6(C-2),136.7(C-13),130.7(C-8),121.6(C-11),119.4(C-10),118.5(C-9),111.2(C-12),108.4(C-7),73.20(C-19),61.9(C-21),54.2(C-5),50.4(C-3),43.6(C-20),41.0(C-16),35.4(C-17),27.5(C-14),24.6(C-15),21.2(C-6),20.3(C-18)。综上所述,化合物数据与文献[

11]报道一致,故鉴定化合物3为19S-hydroxyibogamine。

化合物4 白色粉末,改良碘化铋钾反应呈阳性。[α]D25-85.0°(c 0.35,CH3OH);UV λMaxMeOH:207,293,329 nm;IR(KBr):3 423,2 947,1 717,1 661,1 610,1 461,1 382,751 cm-1;ESI-MS m/z 351.4[M+H+1H NMR(CD3OD,400 MHz) δ:4.22(1H,m,H-5β),3.45(1H,m,H-5α),1.98(1H,m,H-6β),1.86(1H,m,H-6α),7.38(1H,d,J = 7.8 Hz,H-9),7.23(1H,t,J = 7.8 Hz,H-11),7.06(1H,d,J = 7.8 Hz,H-12),6.96(1H,t,J = 7.8 Hz,H-10),6.65(1H,d,J = 9.9 Hz,H-14),5.92(1H,d,J = 9.9 Hz,H-15),4.10(1H,m,H-21),3.80(3H,s,OMe),2.68(1H,d,J = 15.1 Hz,H-17α),2.51(1H,d,J = 15.1 Hz,H-17β),1.07(2H,m,H-19),0.75(3H,d,J = 7.4 Hz,H-18)13C NMR(CD3OD,100 MHz) δ:169.4(COOMe),166.5(C-3),163.5(C-2),148.1(C-15),144.7(C-13),136.8(C-8),129.8(C-11),122.8(C-14),122.6(C-9),122.2(C-10),111.2(C-12),90.6(C-16),67.9(C-21),58.2(C-7),51.6(COOMe),44.9(C-5),44.4(C-6),41.7(C-20),27.9(C-19),27.2(C-17),7.6(C-18)。综上所述,化合物数据与文献[

12]报道一致,故鉴定化合物4为3-oxotabersonine。

化合物5 白色粉末,改良碘化铋钾反应呈阳性。UV λMaxMeOH:206,232,315 nm;IR(KBr):3 419,2 949,1 716,1 643,1 541,1 456,746 cm-1;HR-ESI-MS m/z 339.1708[M+H1H NMR(CD3OD,400 MHz) δ:7.76(1H,d,J = 7.8,H-9),7.40(1H,d,J = 7.8,H-12),7.33(1H,t,J = 7.8 Hz,H-11),7.14(1H,t,J = 7.8 Hz,H-10),5.53(1H,q,J = 6.3 Hz,H-19),4.32(1H,m,H-16),4.21(1H,d,J = 14.6 Hz,H-21β),4.10(1H,m,H-5),3.82(1H,m,H-15),3.73(1H,m,H-6β),3.53(1H,m,H-6α),3.53(1H,m,H-14β),3.26(1H,d,J = 14.6 Hz,H-21α),2.69(1H,s,COOMe),2.63(1H,m,H-14α),1.73(3H,d,J = 6.3 Hz,H-18)13C NMR(CD3OD,100 MHz) δ:192.3(C-3),172.3(COOMe),138.4(C-20),138.1(C-13),135.4(C-2),129.5(C-8),127.6(C-11),121.8(C-9),121.5(C-7),121.4(C-10),121.2(C-19),113.2(C-12),51.80(C-5),51.1(COOMe),49.2(C-16),44.1(C-21),44.0(C-14),32.2(C-15),25.7(C-6),12.2(C-18)。综上所述,化合物数据与文献[

13]报道一致,故鉴定化合物5为派利文碱(perivine)。

化合物6 黄色油状物,改良碘化铋钾反应呈阳性。UV λMaxMeOH:205,227,280 nm;IR(KBr):3 380,2 940,1 717,1 541,1 456,732 cm-1;ESI-MS m/z 323.3[M+H+1H NMR(CD3OD,400 MHz) δ:7.7(1H,d,J = 7.8 Hz,H-12),7.36(1H,d,J = 7.8 Hz,H-9),7.04(1H,t,J = 7.8 Hz,H-11),6.96(1H,t,J = 7.8 Hz,H-10),5.33(1H,q,J = 6.7 Hz,H-19),4.24(1H,m,H-5),3.79(1H,m,H-21β),3.69(1H,m,H-3),3.61(1H,m,H-21α),3.04(3H,s,COOMe),2.99(1H,m,H-15),2.89(2H,m,H-6),2.62(1H,m,H-14β),1.83(1H,m,H-14α),1.64(3H,d,J = 6.7 Hz,H-18)13C NMR(CD3OD,100 MHz) δ:174.2(COOMe),139.7(C-2),138.6(C-13),138.5(C-20),128.1(C-8),122.0(C-11),119.7(C-10),118.4(C-9),116.0(C-19),112.0(C-12),105.3(C-7),56.5(C-21),54.2(C-5),51.6(C-3),51.4(COOMe),44.8(C-16),28.3(C-15),27.8(C-14),24.8(C-6),12.9(C-18)。综上所述,化合物数据与文献[

13]报道一致,故鉴定化合物6为佩西立文(pericyclivine)。

化合物7 黄色粉末,改良碘化铋钾反应呈阳性。UV λMaxMeOH:207,288,335 nm;IR(KBr):3 418,3 216,2 942,1 733,1 649,1 541,1 456,752 cm-1;ESI-MS m/z 353.4[M+H+1H NMR(CD3OD,400 MHz) δ:7.82(1H,d,J = 7.5 Hz,H-9),7.47(1H,d,J = 7.5 Hz,H-12),7.26(1H,t,J = 7.5 Hz,H-11),7.14(1H,t,J = 7.5 Hz,H-10),5.64(1H,q,J = 6.8 Hz,H-19),4.47(1H,m,H-3),4.41(1H,m,H-17a),4.34(1H,m,H-17b),4.08(1H,d,J = 17.3 Hz,H-21α),3.21(1H,d,J = 17.3 Hz,H-21β),3.16(3H,s,COOMe),3.15(1H,m,H-6β),2.66(1H,m,H-5α),2.55(1H,m,H-5β),2.45(1H,m,H-14α),2.37(1H,m,H-14β),3.28(1H,m,H-15),1.80(1H,m,H-6α),1.75(3H,d,J = 6.8 Hz,H-18)13C NMR(CD3OD,100 MHz) δ:191.5(C-2),173.8(COOMe),156.1(C-13),148.3(C-8),139.2(C-20),128.5(C-11),127.0(C-9),126.6(C-10),122.9(C-19),120.7(C-12),65.0(C-16),64.2(C-17),58.9(C-7),55.7(C-3),53.6(C-21),52.0(COOMe),51.8(C-5),36.3(C-6),35.8(C-15),32.2(C-14),14.7(C-18)。综上所述,化合物数据与文献[

14]报道一致,故鉴定化合物7为rhazinalinol。

化合物8 黄色粉末;改良碘化铋钾反应呈阳性。αD25 -18.5°(c 0.72,CH3OH);UV λMaxMeOH:207,223,281 nm;HR-ESI-MS m/z 297.196 9[M+H 1H NMR(CD3OD,400 MHz) δ:7.41(1H,d,J = 7.8 Hz,H-9),7.33(1H,d,J = 7.8 Hz,H-12),7.07(1H,t,J = 7.8 Hz,H-11),6.99(1H,t,J = 7.8 Hz,H-10),5.59(1H,q,J = 6.8 Hz,H-19),4.29(1H,s,H-3),3.67(1H,m,H-21α),3.43(2H,m,H-17),3.25(1H,m,H-5α),3.12(1H,m,H-5β),3.04(1H,m,H-6α),3.04(1H,m,H-21β),2.97(1H,m,H-15),2.68(1H,m,H-6β),2.27(2H,t,J = 5.1 Hz,H-14),1.69(3H,q,J = 6.8 Hz,H-18),1.59(1H,m,H-16a),1.42(1H,m,H-16b)13C NMR(CD3OD,100 MHz) δ:137.8(C-13),137.5(C-20),134.4(C-2),128.5(C-8),122.8(C-19),122.1(C-11),119.8(C-10),118.6(C-9),112.0(C-12),107.0(C-7),61.0(C-17),54.70(C-3),54.0(C-21),51.90(C-5),36.9(C-16),33.3(C-14),32.2(C-15),18.70(C-6),13.2(C-18)。综上所述,化合物数据与文献[

15]报道一致,故鉴定化合物8为geissoschizol。

化合物9 黄色粉末;改良碘化铋钾反应呈阳性;UV λMaxMeOH:203,241,285,306,339 nm; ESI-MS m/z 249.3[M+H+1H NMR(CD3OD,400 MHz) δ:8.18(1H,s,H-21),8.11(1H,d,J = 7.8 Hz,H-9),7.52(1H,d,J = 7.8 Hz,H-12),7.41(1H,t,J = 7.8 Hz,H-11),7.22(1H,t,J = 7.8 Hz,H-10),4.11(2H,m,H-3),3.29(2H,m,H-14),2.65(3H,s,H-18),2.55(3H,s,H-17)13C NMR(CD3OD,100 MHz) δ:150.0(C-19),142.5(C-2),142.0(C-13),129.2(C-15),127.1(C-11),124.7(C-8),122.8(C-7),121.7(C-20),121.2(C-9),120.7(C-10),118.5(C-16),117.6(C-21),112.2(C-12),57.5(C-3),25.7(C-14),13.9(C-18),13.0(C-17)。综上所述,化合物数据与文献[

16]报道一致,故鉴定化合物9为3,14-dihydroolivacine。

化合物10 黄色粉末,改良碘化铋钾反应呈阳性。UV λMaxMeOH:221,283;IR(KBr):3 396,3 261,2 945,1 716,1 646,1 620,1 541,1 459,744 cm-1;HR-ESI-MS m/z 341.186 6[M+H 1H NMR(CD3OD,400 MHz) δ:7.43(1H,d,J = 7.8 Hz,H-9),7.33(1H,d,J = 7.8 Hz,H-12),7.11(1H,t,J = 7.8 Hz,H-11),7.01(1H,t,J = 7.8 Hz,H-10),5.60(1H,q,J = 6.6 Hz,H-19),4.70(1H,d,J = 16.8 Hz,H-17a),4.18(2H,m,H-5),4.17(1H,d,J = 10.1 Hz,H-21α),4.04(1H,d,J = 16.8 Hz,H-17b),3.81(1H,d,J = 10.1 Hz,H-21β),3.77(3H,s,COOMe),3.59(1H,m,H-3a),3.50(1H,m,H-3b),2.86(1H,d,J = 8.7 Hz,H-15),2.28(1H,m,H-14a),1.93(1H,m,H-14b),1.77(3H,d,J = 6.6 Hz,H-18)13C NMR(CD3OD,100 MHz) δ:176.1(COOMe),136.7(C-13),134.5(C-2),134.3(C-20),129.3(C-8),125.5(C-19),122.9(C-11),119.7(C-10),118.6(C-9),111.6(C-12),108.7(C-7),70.6(C-17),60.2(C-16),54.6(C-21),53.1(COOMe),51.3(C-5),48.4(C-3),37.2(C-15),24.9(C-14),14.2(C-18)。综上所述,化合物数据与文献[

17]报道一致,故鉴定化合物10为瓦莱萨明碱(vallesamine)。

化合物11 黄色粉末,改良碘化铋钾反应呈阳性。αD25 +24.1°(c 0.21,CHCl3);UV λMaxMeOH:209,313 nm;IR(KBr):3 420,2 931,1 672,1 547,1 457,1 385,748 cm-1;HR-ESI-MS m/z 283.144 7[M+H1H NMR(CD3OD,400 MHz) δ:7.60(1H,d,J = 7.8 Hz,H-9),7.42(1H,d,J = 7.8 Hz,H-12),7.32(1H,t,J = 7.8 Hz,H-11),7.09(1H,t,J = 7.8 Hz,H-10),4.84(1H,m,H-6a),4.51(1H,m,H-6b),3.71(1H,d,J = 15.3 Hz,H-21α),3.36(1H,m,H-3a),3.24(1H,d,J = 6.6 Hz,H-15),3.20(1H,m,H-3b);2.98(1H,q,J = 5.4 Hz,H-19),2.66(1H,d,J = 15.3 Hz,H-21β),2.23(1H,m,H-14a),2.12(1H,m,H-14b),1.29(3H,d,J = 5.4 Hz,H-18)13C NMR(CD3OD,100 MHz) δ:193.3(C-16),138.5(C-13),132.5(C-2),128.9(C-8),127.3(C-11),121.4(C-9),121.0(C-10),113.2(C-12),119.3(C-7),60.9(C-20),57.9(C-19),55.7(C-21),54.4(C-6),47.4(C-15),44.5(C-3),23.6(C-14),13.3(C-18)。综上所述,化合物数据与文献[

10]报道一致,故鉴定化合物11为conolobine A。

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