北重楼地上部分的化学成分研究

姜鹏，刘艳，潘娟，刘源，许振鹏，杨炳友

(黑龙江中医药大学，黑龙江 哈尔滨 150040)

北重楼(ParisverticillataM.Bieb.)为百合科(Liliaceae)重楼属(Paris)植物，其药用部位为根茎，临床多用于治疗高热抽搐、热病烦躁、咽喉肿痛、疔疖肿毒、毒蛇咬伤等[1-2]。近年来，因重楼具有资源分布的广泛性、生物活性的多样性使其受到国内外学者的关注[3-5]。但对于北重楼各方面的研究报道较少，从很大程度上限制了对重楼这一药用资源更深入的研究应用。北重楼主要分布在黄河以北地区，以东三省为主，资源比较丰富，但在采收期时，由于地上部分生长较快，大量被丢弃，造成了严重的资源浪费。本文对北重楼地上部分的正丁醇层进行了系统研究，通过多种色谱及波谱学方法从中分离并鉴定其化学成分。

1 仪器与材料

旋转蒸发仪(EYELA公司)；AV-600型超导核磁共振波谱仪(Bruker公司)；Q-TOF(ESI)高分辨质谱仪(Waters公司)；中压制备(布奇公司)；制备型高效液相色谱(岛津公司)；分析型高效液相色谱(Waters公司)；Shim-pack GIST C18分析柱(5 μm，20 mm×250 mm，岛津公司)；Sephadex LH-20(GE Healthcare公司)；反相ODS(YMC公司)；柱色谱硅胶(200～300目)(青岛海洋化工厂);薄层色谱硅胶(青岛海洋化工厂)；色谱甲醇(默克公司)。

北重楼地上部分药材于2019年6月采收于黑龙江省尚志市帽儿山，经黑龙江中医药大学药学院樊锐锋教授鉴定为北重楼(ParisverticillataM.Bieb.)。原植物标本(20190806)保存于黑龙江中医药大学中药化学实验室。

2 提取与分离

北重楼地上部分药材50.5 kg(干燥)，以70%乙醇为溶剂，加热回流提取3次，每次2 h，减压回收溶剂，最终得到提取物浸膏4 kg。将浸膏经水分散，分别采用乙酸乙酯和水饱和正丁醇依次进行萃取，并将得到的萃取液分别浓缩至浸膏状，最终得到正丁醇萃取部位浸膏400 g。取315 g的正丁醇层浸膏经正相硅胶柱色谱进行分离，以二氯甲烷-甲醇(100∶1→0∶1)系统为流动相进行梯度洗脱，将得到的洗脱液进行反复的TLC检识合并，最终共得到10个组分即Fr.A～Fr.J。Fr.F经ODS柱色谱，凝胶柱色谱以及制备型HPLC分离得到化合物1(5.6 mg)、3(3.5 mg)、4(3.2 mg)、9(3.0 mg)、11(3.0 mg)、12(4.5 mg)。Fr.G经ODS柱色谱，凝胶柱色谱以及制备型HPLC分离得到化合物2(2.5 mg)、5(5.0 mg)、6(4.0 mg)、7(2.5 mg)、8(5.0 mg)、10(4.2 mg)、13(3.6 mg)、14(4.4 mg)。

3 结构鉴定

3.1 化合物1

白色无定形粉末。HR-ESI-MS m/z: 373.222 6 [M+H]+，分子式为C19H32O7。1H-NMR (CD3OD, 600 MHz) δ：1.97 (1H, d, J = 17.3 Hz, H-2a), 2.46 (1H, d, J = 17.3 Hz, H-2b), 5.80 (1H, s, H-4), 1.99 (1H, m, H-6), 1.97 (1H, m, H-7), 1.64 (2H, m, H-8), 3.88 (1H, m, H-9), 1.18 (3H, d, J = 6.2 Hz, H-10), 1.00 (3H, s, H-11), 1.08 (3H, s, H-12), 2.04 (3H, d, J = 0.8 Hz, H-13), 4.32 (1H, d, J = 7.8 Hz, H-1′), 3.13 (1H, m, H-2′), 3.35 (1H, m, H-3′), 3.26 (2H, m, H-4′, H-5′), 3.85 (1H, m, H-6′a), 3.64 (1H, dd, J = 11.7,6.0 Hz, H-6′b)。13C-NMR (CD3OD, 150 MHz) δ：37.4 (C-1), 48.1 (C-2), 202.5 (C-3), 125.4 (C-4), 170.1 (C-5), 52.4 (C-6), 26.9 (C-7), 37.8 (C-8), 75.5 (C-9), 19.9 (C-10), 27.6 (C-11), 29.0 (C-12), 25.0 (C-13), 102.1 (C-1′), 75.2 (C-2′), 78.2 (C-3′), 71.8 (C-4′), 77.9 (C-5′), 62.9 (C-6′)。上述数据与文献[6]报道基本一致，故鉴定为byzantionoside B。

3.2 化合物2

白色无定形粉末。HR-ESI-MS m/z: 387.201 9 [M+H]+，分子式为C19H30O8。1H-NMR (CD3OD, 600 MHz) δ：2.50 (1H, d, J = 16.8 Hz, H-2a)，2.14 (1H, d, J = 16.8 Hz, H-2b), 5.85 (1H, s, H-4), 5.86 (2H, m, H-7, H-8), 4.41 (1H, m, H-9), 1.28 (3H, d, J = 6.4 Hz, H-10), 1.03 (3H, s, H-11), 1.02 (3H, s, H-12), 1.91 (3H, s, H-13), 4.32 (1H, d, J = 7.8 Hz, H-1′), 3.15 (1H, t, J = 7.8 Hz, H-2′), 3.36 (1H, m, H-3′), 3.24 (2H, m, H-4′, H-5′), 3.84 (1H, dd, J = 12.5,2.0 Hz, H-6′a), 3.61 (1H, dd, J = 12.5,5.5 Hz, H-6′b)。13C-NMR (CD3OD, 150 MHz) δ：42.5 (C-1), 50.7 (C-2), 201.2 (C-3), 127.2 (C-4), 167.3 (C-5), 80.0 (C-6), 131.6 (C-7), 135.3 (C-8), 77.3 (C-9), 21.2 (C-10), 23.4 (C-11), 24.7 (C-12), 19.6 (C-13), 102.8 (C-1′), 75.3 (C-2′), 78.2 (C-3′), 71.7 (C-4′), 78.1 (C-5′), 62.9 (C-6′)。上述数据与文献[7]报道基本一致，故鉴定为vomifoliol 9-O-β-D-glucopyranoside。

3.3 化合物3

白色无定形粉末。HR-ESI-MS m/z: 389.217 5 [M+H]+，其分子式为C19H32O8。1H-NMR (CD3OD, 600 MHz) δ：5.82 (1H, s, H-2), 2.61 (1H, d, J = 17.9 Hz, H-6a), 2.14 (1H, d, J = 17.9 Hz, H-6b), 2.03 (1H, m, H-7a), 1.81 (1H, m, H-7b), 1.75 (1H, m, H-8a), 1.48 (1H, m, H-8b), 3.81 (1H, m, H-9), 1.17 (3H, d, J = 6.2 Hz, H-10), 1.09 (3H, s, H-11), 1.00 (3H, s, H-12), 2.03 (3H, s, H-13), 4.30 (1H, d, J = 7.9 Hz, H-1′), 3.12 (1H, dd, J = 9.2,7.9 Hz, H-2′), 3.31 (1H, o, H-3′), 3.25 (2H, m, H-4′, H-5′), 3.86 (1H, dd, J = 11.9,2.1 Hz, H-6′a), 3.64 (1H, dd, J = 11.9,5.2 Hz, H-6′b)。13C-NMR (CD3OD, 150 MHz) δ：201.1 (C-1), 126.7 (C-2), 171.7 (C-3), 79.3 (C-4), 42.9 (C-5), 51.1 (C-6), 34.9 (C-7), 33.6 (C-8), 76.2 (C-9), 20.1 (C-10), 24.1 (C-11), 24.7 (C-12), 21.7 (C-13), 102.3 (C-1′), 75.2 (C-2′), 78.2 (C-3′), 71.8 (C-4′), 78.0 (C-5′), 62.9 (C-6′)。上述数据与文献[8]报道基本一致，故鉴定为dihydrovomifoliol-O-β-D-glucopyranoside。

3.4 化合物4

白色无定形粉末。HR-ESI-MS m/z: 389.217 5 [M+H]+，分子式为C19H32O8。1H-NMR (CD3OD, 600 MHz) δ：2.15 (1H, d, J = 17.3 Hz, H-2a), 2.57 (1H, d, J = 17.3 Hz, H-2b), 2.17 (1H, d, J = 17.3 Hz, H-4a), 2.53 (1H, d, J = 17.3 Hz, H-4b), 1.73 (1H, m, H-6), 1.49 (1H, m, H-7a), 1.84 (1H, m, H-7b), 1.70 (1H, m, H-8a), 1.78 (1H, m, H-8b), 3.94 (1H, m, H-9), 1.21 (3H, d, J = 6.2 Hz, H-10), 1.08 (3H, s, H-11), 3.55 (1H, dd, J = 7.8,2.5 Hz, H-12a), 3.57 (1H, d, J = 7.8 Hz, H-12b), 1.31 (3H, s, H-13), 4.33 (1H, d, J = 7.8 Hz, H-1′), 3.14 (1H, dd, J = 9.2,7.8 Hz, H-2′), 3.36 (1H, o, H-3′), 3.25 (2H, m, H-4′, H-5′), 3.85 (1H, dd, J = 11.5,1.3 Hz, H-6′a), 3.61 (1H, dd, J = 11.5,5.6 Hz, H-6′b)。13C-NMR (CD3OD, 150 MHz) δ：44.8 (C-1), 49.9 (C-2), 212.4 (C-3), 50.6 (C-4), 85.6 (C-5), 54.8 (C-6), 22.1 (C-7), 37.7 (C-8), 75.9 (C-9), 20.0 (C-10), 20.9 (C-11), 79.5 (C-12), 25.2 (C-13), 102.3 (C-1′), 75.2 (C-2′), 78.2 (C-3′), 71.9 (C-4′), 78.0 (C-5′), 63.0 (C-6′)。上述数据与文献[9]报道基本一致，故鉴定为macarangioside F。

3.5 化合物5

白色无定形粉末。HR-ESI-MS m/z: 391.233 2 [M+H]+，其分子式为C19H34O8。1H-NMR (CD3OD, 600 MHz) δ：1.67 (1H, t, J = 12.0 Hz, H-2a), 1.56 (1H, m, H-2b), 3.95 (1H, m, H-3), 1.80 (1H, m, H-4a), 1.49 (1H, m, H-4b), 1.94 (1H, m, H-5), 5.55 (1H, dd, J = 15.7,1.0 Hz, H-7), 5.72 (1H, dd, J = 15.7,6.0 Hz, H-8), 4.28 (1H, m, H-9), 1.23 (3H, d, J = 6.4 Hz, H-10), 0.97 (3H, s, H-11), 0.90 (3H, s, H-12), 0.81 (3H, d, J = 6.7 Hz, H-13), 4.34 (1H, d, J = 7.9 Hz, H-1′), 3.12 (1H, dd, J = 9.1,7.9 Hz, H-2′), 3.36 (1H, o, H-3′), 3.25 (2H, m, H-4′, H-5′), 3.86 (1H, dd, J = 11.9,2.1 Hz, H-6′a), 3.64 (1H, dd, J = 11.9,5.2 Hz, H-6′b)。13C-NMR (CD3OD, 150 MHz) δ：40.5 (C-1), 42.6 (C-2), 75.7 (C-3), 38.2 (C-4), 35.6 (C-5), 78.3 (C-6), 133.8 (C-7), 135.6 (C-8), 69.3 (C-9), 24.2 (C-10), 25.1 (C-11), 25.9 (C-12), 16.5 (C-13), 102.7 (C-1′), 75.2 (C-2′), 78.1 (C-3′), 71.8 (C-4′), 77.9 (C-5′), 62.9 (C-6′)。上述数据与文献[10]报道基本一致，故鉴定为turpinionoside A。

3.6 化合物6

白色无定形粉末。HR-ESI-MS m/z: 405.212 5 [M+H]+，其分子式为C19H32O9。1H-NMR (CD3OD, 600 MHz) δ：1.73 (1H, ddd, J = 13.0,3.2,1.2 Hz, H-2a), 1.41 (1H, dd, J = 13.0,10.0 Hz, H-2b), 3.91 (1H, m, H-3), 2.40 (1H, dd, J = 14.7,4.9 Hz, H-4a), 1.80 (1H, dd, J = 14.7,8.3 Hz, H-4b), 7.15 (1H, d, J = 15.8 Hz, H-7), 6.18 (1H, d, J = 15.8 Hz, H-8), 2.28 (3H, s, H-10), 0.95 (3H, s, H-11), 1.20 (3H, s, H-12), 1.18 (3H, s, H-13), 4.33 (1H, d, J = 7.9 Hz, H-1′), 3.11 (1H, dd, J = 8.9,7.9 Hz, H-2′), 3.36 (1H, o, H-3′), 3.26 (2H, m, H-4′, H-5′), 3.84 (1H, dd, J = 11.9,2.1 Hz, H-6′a), 3.66 (1H, dd, J = 11.9,5.2 Hz, H-6′b)。13C-NMR (CD3OD, 150 MHz) δ：36.0 (C-1), 45.2 (C-2), 72.8 (C-3), 38.2 (C-4), 68.4 (C-5), 71.2 (C-6), 145.3 (C-7), 133.9 (C-8), 200.3 (C-9), 27.5 (C-10), 25.5 (C-11), 29.5 (C-12), 20.2 (C-13), 103.0 (C-1′), 75.2 (C-2′), 77.9 (C-3′), 71.6 (C-4′), 78.2 (C-5′), 62.7 (C-6′)。上述数据与文献[11]报道基本一致，故鉴定为5β,6α-dihydroxy-3β-(β-D-glucoyranosyloxy)-7-megastigmen-9-one。

3.7 化合物7

白色无定形粉末。HR-ESI-MS m/z: 387.201 9 [M+H]+，其分子式为C19H30O8。1H-NMR (CD3OD, 600 MHz) δ：2.03 (2H, d, J = 12.7 Hz, H-2), 4.34 (1H, m, H-3), 2.32 (2H, d, J = 12.7 Hz, H-4), 5.90 (1H, s, H-8), 2.27 (3H, s, H-10), 1.12 (3H, s, H-11), 1.43 (3H, s, H-12), 1.37 (3H, s, H-13), 4.42 (1H, d, J = 7.9 Hz, H-1′), 3.14 (1H, dd, J = 8.9,7.9 Hz, H-2′), 3.36 (1H, o, H-3′), 3.25 (2H, m, H-4′, H-5′), 3.86 (1H, m, H-6′a), 3.68 (1H, m, H-6′b)。13C-NMR (CD3OD, 150 MHz) δ：36.9 (C-1), 48.1 (C-2), 72.6 (C-3), 46.8 (C-4), 72.5 (C-5), 120.2 (C-6), 211.1 (C-7), 101.4 (C-8), 202.2 (C-9), 27.0 (C-10), 32.5 (C-11), 29.3 (C-12), 30.9 (C-13), 102.7 (C-1′), 75.1 (C-2′), 78.2 (C-3′), 71.7 (C-4′), 77.9 (C-5′), 62.8 (C-6′)。上述数据与文献[12]报道基本一致，故鉴定为austroside B。

3.8 化合物8

白色无定形粉末。HR-ESI-MS m/z: 197.117 8 [M+H]+，其分子式为C11H16O3。1H-NMR (CD3OD, 600 MHz) δ：1.52 (1H, dd, J = 14.4,3.7 Hz, H-2a), 1.98 (1H, dt, J = 14.4,2.7 Hz, H-2b), 4.20 (1H, m, H-3), 1.73 (1H, br.d, J = 4.0 Hz, H-4a), 2.40 (1H, dt, J = 13.4,2.7 Hz, H-4b), 5.74 (1H, s, H-7), 1.46 (3H, s, H-9), 1.26 (3H, s, H-10), 1.75 (3H, s, H-11)。13C-NMR (CD3OD, 150 MHz) δ：37.2 (C-1), 48.0 (C-2), 67.3 (C-3), 46.5 (C-4), 89.0 (C-5), 185.7 (C-6), 113.4 (C-7), 174.5 (C-8), 27.0 (C-9), 31.0 (C-10), 27.5 (C-11)。上述数据与文献[13]报道基本一致，故鉴定为loliolide。

3.9 化合物9

白色无定形粉末。HR-ESI-MS m/z: 263.149 5 [M+H]+，分子式为C12H22O6。1H-NMR (CD3OD, 600 MHz) δ：3.53 (2H, m, H-1), 2.37 (2H, q, J = 7.2 Hz, H-2), 5.37 (1H, m, H-3), 5.45 (1H, m, H-4), 2.07 (2H, q, J = 7.5 Hz, H-5), 0.96 (3H, t, J = 7.5 Hz, H-6), 4.25 (1H, d, J = 7.8 Hz, H-1′), 3.14 (1H, dd, J = 9.0,7.9 Hz, H-2′), 3.34 (1H, o, H-3′), 3.25 (2H, m, H-4′, H-5′), 3.86 (1H, m, H-6′a), 3.66 (1H, m, H-6′b)。13C-NMR (CD3OD, 150 MHz) δ：70.5 (C-1), 28.8 (C-2), 134.5 (C-3), 125.9 (C-4), 21.6 (C-5), 14.6 (C-6), 104.4 (C-1′), 75.1 (C-2′), 78.0 (C-3′), 71.7 (C-4′), 78.2 (C-5′), 62.8 (C-6′)。上述数据与文献[14]报道基本一致，故鉴定为(Z)-3-hexenyl β-D-glucopyranoside。

3.10 化合物10

白色无定形粉末。HR-ESI-MS m/z: 417.176 1 [M+H]+，分子式为C19H28O10。1H-NMR (CD3OD, 600 MHz) δ：7.25 (4H, m, H-2, H-3, H-5, H-6), 7.16 (1H, m, H-4), 2.93 (2H, m, H-7), 3.75 (2H, m, H-8), 4.28 (1H, d, J = 7.8 Hz, H-1′), 3.16 (1H, dd, J = 8.9,7.8 Hz, H-2′), 3.38 (1H, m, H-3′), 3.25 (2H, m, H-4′, H-5′), 3.88 (1H, d, J = 2.3 Hz, H-6′a), 3.68 (1H, m, H-6′b), 4.99 (1H, d, J = 2.4 Hz, H-1″), 4.04 (1H, m, H-2″), 3.96 (2H, m, H-4″), 3.55 (2H, s, H-5″)。13C-NMR (CD3OD, 150 MHz) δ：140.1 (C-1), 129.4 (C-2, C-6), 130.1 (C-3, C-5), 127.2 (C-4), 37.3 (C-7), 71.9 (C-8), 104.5 (C-1′), 75.0 (C-2′), 78.0 (C-3′), 71.7 (C-4′), 76.9 (C-5′), 68.7 (C-6′), 111.0 (C-1″), 78.1 (C-2″), 80.6 (C-3″), 75.1 (C-4″), 65.6 (C-5″)。上述数据与文献[15]报道基本一致，故鉴定为icariside D1。

3.11 化合物11

白色无定形粉末。HR-ESI-MS m/z: 403.160 4 [M+H]+, 分子式为C18H26O10。1H-NMR (CD3OD, 600 MHz) δ：7.41 (2H, m, H-2, H-6), 7.32 (2H, m, H-3, H-5), 7.26 (1H, m, H-4), 4.64 (1H, d, J = 11.8 Hz, H-7a), 4.88 (1H, d, J = 11.8 Hz, H-7b), 4.32 (1H, d, J = 7.8 Hz, H-1′), 3.14 (1H, dd, J = 8.9,7.8 Hz, H-2′), 3.38 (1H, m, H-3′), 3.25 (2H, m, H-4′, H-5′), 3.88 (1H, m, H-6′a), 3.68 (1H, m, H-6′b), 5.04 (1H, d, J = 2.5 Hz, H-1″), 4.01 (1H, m, H-2″), 3.98 (2H, m, H-4″), 3.58 (2H, s, H-5″)。13C-NMR (CD3OD, 150 MHz) δ：139.0 (C-1), 129.3 (C-2, C-3, C-5, C-6), 128.7 (C-4), 71.6 (C-7), 103.2 (C-1′), 75.0 (C-2′), 78.0 (C-3′), 71.9 (C-4′), 77.0 (C-5′), 68.7 (C-6′), 111.0 (C-1″), 78.1 (C-2″), 80.6 (C-3″), 75.1 (C-4″), 65.6 (C-5″)。上述数据与文献[16]报道基本一致，故鉴定为icariside F2。

3.12 化合物12

白色无定形粉末。HR-ESI-MS m/z: 268.104 6 [M+H]+，分子式为C10H13N5O4。1H-NMR (C5D5N, 600 MHz) δ：8.61 (1H, s, H-2), 8.36 (1H, s, H-8), 6.71 (1H, d, J = 5.8 Hz, H-1′), 5.06 (1H, m, H-2′), 5.49 (1H, t, J = 5.5 Hz, H-3′), 4.76 (1H, dd, J = 5.5,2.7 Hz, H-4′), 4.31 (1H, dd, J = 12.4,2.7 Hz, H-5′a), 4.13 (1H, dd, J = 12.4,2.7 Hz, H-5′b)。13C-NMR (C5D5N, 150 MHz) δ：153.2 (C-2), 150.0 (C-4), 121.3 (C-5), 157.5 (C-6), 140.4 (C-8), 90.7 (C-1′), 75.4 (C-2′), 72.3 (C-3′), 87.7 (C-4′), 62.9 (C-5′)。上述数据与文献[17]报道基本一致，故鉴定为adenosine。

3.13 化合物13

白色无定形粉末。HR-ESI-MS m/z: 267.102 1 [M+H]+, 分子式为C17H14O3。1H-NMR (CD3OD, 600 MHz) δ：7.64 (1H, d, J = 15.9 Hz, H-1), 6.37 (1H, d, J = 15.9 Hz, H-2), 5.81 (1H, d, J = 12.8 Hz, H-4), 6.90 (1H, d, J = 12.8 Hz, H-5), 7.47 (2H, d, J = 8.6 Hz, H-2′, H-6′), 6.80 (2H, d, J = 8.6 Hz, H-3′, H-5′), 7.65 (2H, d, J = 8.6 Hz, H-2″, H-6″), 6.72 (2H, d, J = 8.6 Hz, H-3″, H-5″)。13C-NMR (CD3OD, 150 MHz) δ：147.3 (C-1), 115.8 (C-2), 173.2 (C-3), 160.2 (C-4), 143.5 (C-5), 127.2 (C-1′), 131.3 (C-2′), 115.8 (C-3′), 161.2 (C-4′), 115.8 (C-5′), 131.3 (C-6′), 127.2 (C-1″), 133.9 (C-2″, C-6″), 114.6 (C-3″, C-5″), 116.8 (C-4″)。上述数据与文献[18]报道基本一致，故鉴定为kinsenone。

3.14 化合物14

白色无定形粉末。HR-ESI-MS m/z: 282.279 7 [M+H]+，分子式为C18H35NO。1H-NMR (CD3OD, 600 MHz) δ：2.18 (2H, t, J = 7.4 Hz, H-2), 1.59 (2H, t, J = 7.4 Hz, H-3), 1.29 (20H, m, H-4～H-7, H-12～H-17), 2.01 (2H, m, H-8), 5.33 (1H, t, J = 4.6 Hz, H-9), 5.33 (1H, t, J = 4.6 Hz, H-10), 2.01 (2H, m, H-11), 0.89 (3H, t, J = 7.0 Hz, H-18)。13C-NMR (CD3OD, 150 MHz) δ：179.3 (C-1), 36.5 (C-2), 26.9 (C-3), 30.3 (C-4), 30.4 (C-5, C-6), 30.8 (C-7), 28.1 (C-8), 130.8 (C-9), 130.8 (C-10), 28.1 (C-11), 30.6 (C-12, C-13, C-15), 30.7 (C-14), 33.1 (C-16), 23.7 (C-17), 14.4 (C-18)。上述数据与文献[19]报道基本一致，故鉴定为9(Z)-octadecenamide。

4 结果与讨论

本研究对北重楼地上部分正丁醇层进行了系统的化学成分分离，共得到14个化合物，包括8个萜类化合物byzantionoside B (1)、vomifoliol 9-O-β-D-glucopyranoside (2)、dihydrovomifoliol-O-β-D-glucopyranoside (3)、macarangioside F (4)、turpinionoside A (5)、5β,6α-dihydroxy-3β-(β-D-glucoyranosyloxy)-7-megastigmen-9-one (6)、austroside B (7)、loliolide (8)，4个糖苷类化合物(Z)-3-hexenyl β-D-glucopyranoside (9)、icariside D1 (10)、icariside F2 (11)、adenosine (12)和2个其他类化合物kinsenone (13)、9(Z)-octadecenamide (14)。其中化合物1～7、10、11、14为首次从百合科植物中分离得到，化合物8、9为首次从重楼属植物中分离得到。本研究进一步丰富了北重楼地上部分的化学成分，为深入挖掘北重楼的药效物质基础，合理利用其药用资源提供了科学依据。