CN104447673B - Chinese fiber crops compound and its separation method - Google Patents

Chinese fiber crops compound and its separation method Download PDF

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CN104447673B
CN104447673B CN201410759356.3A CN201410759356A CN104447673B CN 104447673 B CN104447673 B CN 104447673B CN 201410759356 A CN201410759356 A CN 201410759356A CN 104447673 B CN104447673 B CN 104447673B
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CN104447673A (en
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白乃生
张建春
刘庆超
张丽
白璐
侯宇飞
何锦凤
张海
刘雪英
张生勇
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Northwest University
Quartermaster Research Institute of General Logistics Department of CPLA
Fourth Military Medical University FMMU
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NORTHWEST UNIVERSITY
Quartermaster Research Institute of General Logistics Department of CPLA
Fourth Military Medical University FMMU
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Abstract

The invention discloses by seven kinds of noval chemical compounds and its separation method separating obtained in Chinese sesame slices, slightly carried through 95% ethanol by Chinese sesame slices, macroporous resin adsorption, extraction, silica gel column chromatography, the column chromatographies of Spheladex LH 20, CHP20P column chromatographies and high performance liquid chromatograph are separating obtained repeatedly, and utilize its structure of the technical appraisement such as a peacekeeping two-dimentional NMR, mass spectrum.

Description

汉麻化合物及其分离方法Hemp compound and its separation method

技术领域technical field

本发明涉及从汉麻叶中分离鉴定的七种新化合物及其分离方法。The present invention relates to seven new compounds isolated and identified from hemp leaves and their isolation methods.

背景技术Background technique

汉麻(Cannabis sativa L.)系大麻科(Cannabaceae)大麻属(Cannabis)植物。又名线麻，火麻，寒麻等，全国各地均有栽培，资源丰富。汉麻药用历史悠久，《本草纲目》中有关于汉麻入药的记载，麻叶、麻花、麻根提取物可入药，有麻醉、止咳止喘、解痉止痛、止血散淤、解毒安胎等功效；其成熟果实火麻仁性平，味甘，有活血、润燥滑肠、通便等作用，用于治疗血虚津亏，肠燥便秘、月经不调等病；现代药理学研究表明，汉麻还具有抗菌，抗辐射，抗氧化，抗哮喘，抗癌等作用。经查阅大量文献发现，汉麻化学成分种类繁多，先后从中分离得到大麻酚类，黄酮类，萜类，甾类，酯类等多种化学成分。Hemp (Cannabis sativa L.) is a plant of the genus Cannabis in the family Cannabaceae. Also known as thread hemp, hemp hemp, cold hemp, etc., it is cultivated all over the country and has abundant resources. Hemp has a long history of medicinal use. There are records about the use of hemp in "Compendium of Materia Medica". Hemp leaves, twists, and hemp root extracts can be used as medicines, such as anesthesia, cough and asthma, spasm and pain relief, bleeding and stasis, detoxification and miscarriage. Efficacy; the mature fruit of hemp seed is flat in nature, sweet in taste, has the functions of promoting blood circulation, moistening dryness and smoothing intestines, and laxative. , Hemp also has antibacterial, anti-radiation, anti-oxidation, anti-asthma, anti-cancer and other effects. After reviewing a large number of documents, it was found that hemp has a wide variety of chemical components, and various chemical components such as cannabinols, flavonoids, terpenoids, steroids, and esters have been isolated from it.

目前，汉麻植株中的化学成分总共超过537个，而大麻酚类物质总共有超过109个，大麻酚类物质也是研究最多的化合物，尤其是主要的精神活性物质四氢大麻酚(Tetrahydrocannabinol，THC)，然而研究显示，还有一些其他的大麻酚类物质也具有一定的药理活性，比如，不具有精神活性的大麻二酚(Cannabidiol，CBD)也表现出止痛，抗精神活性，抗痉挛，神经保护，止吐等药理特性[12]。非大麻酚类的化合物有黄酮类，萜类，甾类，酯类，糖类及其相关化合物，碳氢化合物，含氮类化合物，氨基酸等。At present, there are more than 537 chemical components in the hemp plant, and there are more than 109 cannabinoids, and the cannabinoids are also the most studied compounds, especially the main psychoactive substance Tetrahydrocannabinol (THC). ), however, studies have shown that there are some other cannabinoids that also have certain pharmacological activities. For example, cannabidiol (CBD), which is not psychoactive, also exhibits analgesic, antipsychotic, antispasmodic, neurological Protection, antiemetic and other pharmacological properties [12] . Non-cannabinol compounds include flavonoids, terpenoids, steroids, esters, sugars and their related compounds, hydrocarbons, nitrogen-containing compounds, amino acids, etc.

发明内容Contents of the invention

本发明旨在提供从汉麻中分离的七种新化合物及其分离方法。The present invention aims to provide seven new compounds isolated from hemp and their isolation methods.

为实现上述目的，本发明采取的技术方案为：In order to achieve the above object, the technical scheme that the present invention takes is:

式I的化合物C15H18O3 Compound of Formula I C 15 H 18 O 3

式II的化合物C21H30O8 Compound C 21 H 30 O 8 of formula II

式III的化合物C20H26O4 Compound C 20 H 26 O 4 of formula III

式IV的化合物C18H22O4 Compound C 18 H 22 O 4 of formula IV

式VII的化合物C20H24O4 Compound C 20 H 24 O 4 of formula VII

式VIII的化合物C25H32O4 Compound C 25 H 32 O 4 of formula VIII

式IX的化合物C25H32O4 Compound C 25 H 32 O 4 of formula IX

所述的新化合物均由汉麻中分离所得。The new compounds are all isolated from hemp.

本发明实施例还提供了上述新化合物的分离方法，包括如下步骤：The embodiment of the present invention also provides a separation method for the above-mentioned novel compound, comprising the following steps:

S1、取11.8kg汉麻(HM)，粉碎，用95％乙醇回流提取3次，料液比为1∶5，回流时间2h；在40℃下减压浓缩，得浸膏约2Kg；浸膏用水分散，用乙酸乙酯萃取3次，浓缩蒸干得1kg浸膏；S1, get 11.8kg hemp (HM), pulverize, reflux extract with 95% ethanol 3 times, solid-liquid ratio is 1: 5, reflux time 2h; Concentrate under reduced pressure at 40 ℃, obtain extractum about 2Kg; Disperse with water, extract 3 times with ethyl acetate, concentrate and evaporate to dryness to obtain 1kg extract;

S2、取步骤S1所得的乙酸乙酯部位浸膏1K g，以1.2K g硅胶拌样，1.5Kg硅胶装柱，进行硅胶柱层析，柱体积6L，用石油醚/乙酸乙酯做洗脱剂进行梯度洗脱，洗脱梯度分别为50∶1，20∶1，10∶1，5∶1，3∶1，1∶1，0∶1，每个梯度收集两个馏分，每个馏分收集两个柱体积，所得各馏分通过LCMS分析检测，合并为4个组分，分别命名为HM-E2(石油醚/丙酮50∶1-20∶1)，HM-E7(石油醚/丙酮20∶1～10∶1)，HM-E9(石油醚/丙酮10∶1～1∶1)，HM-E13(石油醚/丙酮1∶1-0∶1)；S2. Take 1K g of the ethyl acetate part extract obtained in step S1, mix the sample with 1.2K g of silica gel, pack 1.5Kg of silica gel into a column, and perform silica gel column chromatography with a column volume of 6L, eluting with petroleum ether/ethyl acetate gradient elution, the elution gradients were 50:1, 20:1, 10:1, 5:1, 3:1, 1:1, 0:1, two fractions were collected for each gradient, and each fraction Two column volumes were collected, and each fraction obtained was analyzed and detected by LCMS, and combined into 4 components, which were named as HM-E2 (petroleum ether/acetone 50:1-20:1), HM-E7 (petroleum ether/acetone 20 :1～10:1), HM-E9 (petroleum ether/acetone 10:1～1:1), HM-E13 (petroleum ether/acetone 1:1-0:1);

S3、馏分HM-E2(石油醚/丙酮50∶1～20∶1)约100g，通过Flash(ODS C18)中压色谱柱层析和制备液相色谱等分离方法分离得到HM-E2-F4-P4；S3, about 100 g of fraction HM-E2 (petroleum ether/acetone 50:1～20:1), was separated by Flash (ODS C18) medium-pressure chromatographic column chromatography and preparative liquid chromatography to obtain HM-E2-F4- P4;

S4、馏分HM-E7(石油醚/丙酮20∶1～10∶1)约40g，通过Flash(ODS C18)中压色谱柱层析，凝胶柱层析和制备液相色谱等分离方法共分离得到HM-E7-F4-P3-1、HM-E7-F4-P4-1和HM-E7-F4-P7；S4, about 40 g of fraction HM-E7 (petroleum ether/acetone 20:1～10:1), was separated by Flash (ODS C18) medium-pressure column chromatography, gel column chromatography and preparative liquid chromatography and other separation methods HM-E7-F4-P3-1, HM-E7-F4-P4-1 and HM-E7-F4-P7 were obtained;

S5、馏分HM-E9(石油醚/丙酮10∶1～1∶1)约50g，通过Flash(ODS C18)中压色谱柱层析，凝胶柱层析和制备液相色谱等分离方法得到化合物HM-E9-5-F1B-P2，HM-E9-5-F3B-P1，HM-E9-5-F3B-P2，HM-E9-5-F8A-P1，HM-E9-5-F8A-P2，HM-E9-7-S7-P1，HM-E9-7-S10-P3；S5, about 50 g of fraction HM-E9 (petroleum ether/acetone 10:1～1:1), obtained the compound by separation methods such as Flash (ODS C18) medium pressure chromatographic column chromatography, gel column chromatography and preparative liquid chromatography HM-E9-5-F1B-P2, HM-E9-5-F3B-P1, HM-E9-5-F3B-P2, HM-E9-5-F8A-P1, HM-E9-5-F8A-P2, HM-E9-7-S7-P1, HM-E9-7-S10-P3;

S6、馏分HM-E13(石油醚/丙酮1∶1～0∶1)约40g，通过Flash(ODS C18)中压色谱柱层析，凝胶柱层析和制备液相色谱等分离方法得到化合物HM-E13-F1-S11-P4，HM-E13-F1-S13-P2，HM-E13-F1-S13-P3P。S6, about 40 g of fraction HM-E13 (petroleum ether/acetone 1:1～0:1), obtained the compound by separation methods such as Flash (ODS C18) medium-pressure chromatography, gel column chromatography and preparative liquid chromatography HM-E13-F1-S11-P4, HM-E13-F1-S13-P2, HM-E13-F1-S13-P3P.

本发明从汉麻叶中分离鉴定了7种新化合物，提高了汉麻的综合利用率。The invention separates and identifies 7 new compounds from hemp leaves, and improves the comprehensive utilization rate of hemp.

具体实施方式detailed description

为了使本发明的目的及优点更加清楚明白，以下结合实施例对本发明进行 进一步详细说明。应当理解，此处所描述的具体实施例仅仅用以解释本发明，并不用于限定本发明。In order to make the objects and advantages of the present invention clearer, the present invention will be described in further detail below in conjunction with the examples. It should be understood that the specific embodiments described here are only used to explain the present invention, not to limit the present invention.

本发明实施例提供了化合物：HM-E7-F4-P3-1，5-methoxy-2，3，2′，3′-tetrahydro-2H-2′，4′a-ethanoindeno[7，4-bc]oxepin-2-ol，C15H18O3，其结构式如下：The embodiment of the present invention provides the compound: HM-E7-F4-P3-1,5-methoxy-2,3,2',3'-tetrahydro-2H-2',4'a-ethanoindeno[7,4-bc ]oxepin-2-ol, C 15 H 18 O 3 , its structural formula is as follows:

化合物：HM-E13-F1-S11-P4，7-hydroxy-5-methoxyindan-1-spiro-cyclohexan-4′-O-β-D-glucopyranose，C21H30O8其结构式如下：Compound: HM-E13-F1-S11-P4, 7-hydroxy-5-methoxyindan-1-spiro-cyclohexan-4′-O-β-D-glucopyranose, C 21 H 30 O 8 Its structural formula is as follows:

化合物：HM-E2-F4-P4，4′-n-propyl-tetrahydrocannabinoic acid，C20H26O4，其结构式如下：Compound: HM-E2-F4-P4, 4′-n-propyl-tetrahydrocannabinoic acid, C 20 H 26 O 4 , its structural formula is as follows:

化合物：HM-E9-5-P8A-P2，4′-methyl-tetrahydrocannabinoic acid，C18H22O4，其结构式如下：Compound: HM-E9-5-P8A-P2, 4′-methyl-tetrahydrocannabinoic acid, C 18 H 22 O 4 , its structural formula is as follows:

化合物：HM-E7-F4-P7，7，8-dihydro-3，5，4′-trihydroxy-4-methoxy-3′-isopentenylstilbene，C20H24O4，其结构式如下：Compound: HM-E7-F4-P7, 7,8-dihydro-3,5,4′-trihydroxy-4-methoxy-3′-isopentenylstilbene, C 20 H 24 O 4 , its structural formula is as follows:

化合物：HM-E9-5-F3B-P1，α，α′-dihydro-3，5，4′-trihydroxy-4-methoxy-2，6-diisopentenylstilbene，C25H32O4，其结构式如下：Compound: HM-E9-5-F3B-P1, α,α′-dihydro-3,5,4′-trihydroxy-4-methoxy-2,6-diisopentenylstilbene, C 25 H 32 O 4 , its structural formula is as follows:

化合物：HM-E9-5-F3B-P2，α，α′-dihydro-3，5，4′-trihydroxy-4-methoxy-6，3′-diisopentenylstilbene，C25H32O4，其结构式如下：Compound: HM-E9-5-F3B-P2, α,α′-dihydro-3,5,4′-trihydroxy-4-methoxy-6,3′-diisopentenylstilbene, C 25 H 32 O 4 , its structural formula is as follows:

其中，上述化合物的谱图数据为：Wherein, the spectrum data of the above-mentioned compounds are:

HM-E2-F4-P4.1H NMR(CDCl3)：δ6.37(1H，s，H-2)，6.24(1H，s，H-5′)，3.22(1H，d，J＝10.8Hz，H-1)，2.90(1H，m，H-1″a)，2.75(1H，m，H-1″b)，2.16(2H，m，H-4)，1.92(1H，m，H-5a)，1.68(1H，m，H-6)，1.66(3H，s，3-Me)，1.59(2H，m，H-2″)，1.42(3H，s，H-8)，1.36(1H，m，H-5b)，1.09(3H，s，H-9)，0.94(3H，t，J＝7.6Hz，H-3″).13C NMR(CDCl3)：δ176.3(C-3′-COOH)，164.7(C-2′)，159.7(C-6′)，146.6(C-4′)，133.8(C-3)，123.6(C-2)，112.7(C-5′)，109.9(C-1′)，102.4(C-3′)，78.9(C-7)，45.6(C-6)，38.6(C-1″)，33.5(C-1)，31.2(C-4)，27.4(C-8)，25.0(C-5)，24.7(C-2″)，23.3(C-3-Me)，19.5(C-9)，14.3(C-3″).HM-E2-F4-P4. 1 H NMR (CDCl 3 ): δ6.37 (1H, s, H-2), 6.24 (1H, s, H-5′), 3.22 (1H, d, J=10.8 Hz, H-1), 2.90 (1H, m, H-1″a), 2.75 (1H, m, H-1″b), 2.16 (2H, m, H-4), 1.92 (1H, m, H-5a), 1.68 (1H, m, H-6), 1.66 (3H, s, 3-Me), 1.59 (2H, m, H-2″), 1.42 (3H, s, H-8), 1.36 (1H, m, H-5b), 1.09 (3H, s, H-9), 0.94 (3H, t, J=7.6Hz, H-3″). 13 C NMR (CDCl 3 ): δ176.3 (C-3'-COOH), 164.7(C-2'), 159.7(C-6'), 146.6(C-4'), 133.8(C-3), 123.6(C-2), 112.7(C -5'), 109.9(C-1'), 102.4(C-3'), 78.9(C-7), 45.6(C-6), 38.6(C-1"), 33.5(C-1), 31.2(C-4), 27.4(C-8), 25.0(C-5), 24.7(C-2″), 23.3(C-3-Me), 19.5(C-9), 14.3(C-3 "").

HM-E7-F4-P3-1.1H NMR(CD3OD)：δ6.21(1H，s，H-4)，6.11(1H，d，J＝2.0Hz，H-6)，4.85(3H，d，J＝9.5Hz，H-5-OCH3)，2.76(2H，t，Ja＝7.6Hz，Jb＝7.2Hz，H-3)，2.43(2H，dt，Ja＝13.6Hz，Jb＝3.6Hz，H-2)，1.96(2H，m，H-6′)，1.97(2H，m，H-2′)，1.51(2H，d t，Ja＝13.6Hz，Jb＝3.6Hz，H-5′)，1.28(2H，d，J＝13.2Hz，H-3′).13C NMR(CD3OD)：δ159.9(C-5)，154.6(C-7)，145.5(C-9)，127.9(C-8)，100.3(C-4)，100.0(C-4′)，99.8(C-6)，54.3(C-5-OCH3)，47.2(C-1)，34.7(C-2)，30.6(C-3′)，30.6(C-6′)，30.3(C-3)，29.5(C-5′)，29.5(C-2′).HM-E7-F4-P3-1. 1 H NMR (CD 3 OD): δ6.21 (1H, s, H-4), 6.11 (1H, d, J=2.0Hz, H-6), 4.85 ( 3H, d, J = 9.5Hz, H-5-OCH 3 ), 2.76 (2H, t, Ja = 7.6Hz, Jb = 7.2Hz, H-3), 2.43 (2H, dt, Ja = 13.6 Hz, Jb =3.6Hz, H-2), 1.96(2H, m, H-6′), 1.97(2H, m, H-2′), 1.51(2H, dt, Ja=13.6Hz, Jb= 3.6Hz, H-5'), 1.28 (2H, d, J=13.2Hz, H-3'). 13 C NMR (CD 3 OD): δ159.9 (C-5), 154.6 (C-7) , 145.5(C-9), 127.9(C-8), 100.3(C-4), 100.0(C-4'), 99.8(C-6), 54.3(C-5-OCH3), 47.2(C- 1), 34.7(C-2), 30.6(C-3′), 30.6(C-6′), 30.3(C-3), 29.5(C-5′), 29.5(C-2′).

HM-E7-F4-P4-1.1H NMR(CD3OD)：δ1.98(1H，ddd，H-5a)，1.95(3H，s，H-10)，1.79(3H，s，H-11)，1.78(1H，ddd，H-5b)，1.32(1H，m，H-6a)，1.30(2H，m，H-7)，1.30(2H，m，H-8)，1.16(2H，m，H-6)，0.89(3H，t，H-9).13C NMR(CD3OD)：δ173.1(C-1)，159.0(C-2)，124.3(C-3)，107.8(C-4)，35.5(C-5)，31.4(C-7)，22.4(C-6)，22.1(C-8)，12.9(C-9)，9.4(C-10)，6.8(C-11).HM-E7-F4-P4-1. 1 H NMR (CD 3 OD): δ1.98 (1H, ddd, H-5a), 1.95 (3H, s, H-10), 1.79 (3H, s, H -11), 1.78(1H, ddd, H-5b), 1.32(1H, m, H-6a), 1.30(2H, m, H-7), 1.30(2H, m, H-8), 1.16( 2H, m, H-6), 0.89 (3H, t, H-9). 13 C NMR (CD 3 OD): δ173.1 (C-1), 159.0 (C-2), 124.3 (C-3 ), 107.8(C-4), 35.5(C-5), 31.4(C-7), 22.4(C-6), 22.1(C-8), 12.9(C-9), 9.4(C-10) , 6.8 (C-11).

HM-E7-F4-P7.1H NMR(CD3OD)：δ6.79(1H，s，H-2′)，6.78(1H，d，J＝6.8Hz，H-6′)，6.63(1H，d，J＝8.0Hz，H-5′)，6.17(1H，s，H-2)，6.17(1H，s，H-6)，5.27(1H，t，H-8′)，3.76(3H，s，H-4-OMe)，3.23(2H，d，J＝7.2Hz，H-7′)，1.72(3H，s，H-10′)，1.69(3H，s，H-11′).13CNMR(CD3OD)：δ152.6(C-4′)，149.9(C-3)，149.9(C-5)，138.0(C-1)，133.5(C-4)，133.5，(C-1′)，131.3(C-9′)，129.2(C-2′)，127.5(C-3′)，126.1(C-6′)，122.8(C-8′)，114.2(C-5′)，107.4(C-2)，107.4(C-6)，59.4(C-4-OMe)，37.9(C-8)，36.9(C-7)，27.9(C-7′)，24.6(10′)，16.5(C-11′).HM-E7-F4-P7. 1 H NMR (CD 3 OD): δ6.79 (1H, s, H-2'), 6.78 (1H, d, J=6.8Hz, H-6'), 6.63 ( 1H, d, J=8.0Hz, H-5'), 6.17 (1H, s, H-2), 6.17 (1H, s, H-6), 5.27 (1H, t, H-8'), 3.76 (3H, s, H-4-OMe), 3.23 (2H, d, J=7.2Hz, H-7'), 1.72 (3H, s, H-10'), 1.69 (3H, s, H-11 '). 13 CNMR (CD 3 OD): δ152.6 (C-4'), 149.9 (C-3), 149.9 (C-5), 138.0 (C-1), 133.5 (C-4), 133.5 , (C-1′), 131.3(C-9′), 129.2(C-2′), 127.5(C-3′), 126.1(C-6′), 122.8(C-8′), 114.2( C-5′), 107.4(C-2), 107.4(C-6), 59.4(C-4-OMe), 37.9(C-8), 36.9(C-7), 27.9(C-7′) , 24.6(10′), 16.5(C-11′).

HM-E9-5-F1B-P2.1H NMR(CD3OD)：δ6.79(1H，d，J＝8.0Hz，H-5′)，6.64(1H，d，J＝1.6Hz，H-2′)，6.59(1H，dd，H-6′)，6.31(1H，d，J＝1.88Hz，H-2)，6.26(1H，d，H-6)，3.80(3H，s，H-4′-OMe)，3.75(3H，s，H-4-OMe)，3.74(3H，s，H-5-OMe)，2.72 (2H，brs，H-1a)，2.72(2H，brs，H-1a′).13C NMR(CD3OD)：δ152.8(C-5)，149.8(C-4′)，145.8(C-3)，145.8(C-3′)，137.9(C-1)，134.8(C-1′)，134.4(C-4)，119.3(C-6′)，115，2(C-2′)，111.4(C-5′)，108.7(C-2)，103.9(C-6)，59.6(C-4′-OMe)，55.1(C-4-OMe)，54.90(c-5-OMe)，37.8(C-1a′)，37.0(C-1a).HM-E9-5-F1B-P2. 1 H NMR (CD 3 OD): δ6.79 (1H, d, J = 8.0Hz, H-5'), 6.64 (1H, d, J = 1.6Hz, H -2'), 6.59(1H, dd, H-6'), 6.31(1H, d, J=1.88Hz, H-2), 6.26(1H, d, H-6), 3.80(3H, s, H-4′-OMe), 3.75 (3H, s, H-4-OMe), 3.74 (3H, s, H-5-OMe), 2.72 (2H, brs, H-1a), 2.72 (2H, brs , H-1a'). 13 C NMR (CD 3 OD): δ152.8 (C-5), 149.8 (C-4'), 145.8 (C-3), 145.8 (C-3'), 137.9 ( C-1), 134.8 (C-1′), 134.4 (C-4), 119.3 (C-6′), 115, 2 (C-2′), 111.4 (C-5′), 108.7 (C- 2), 103.9 (C-6), 59.6 (C-4'-OMe), 55.1 (C-4-OMe), 54.90 (c-5-OMe), 37.8 (C-1a'), 37.0 (C- 1a).

HM-E9-5-F3B-P1.1H NMR(CD3OD)：δ6.99(1H，d，J＝8.4Hz，H-10)，6.99(1H，d，J＝8.4Hz，H-14)，6.69(1H，d，J＝8.0Hz，H-11)，6.69(1H，d，J＝8.0Hz，H-13)，5.07(1H，s，H-2′)，5.07(1H，s，H-2″)，3.73(3H，s，H-4-OCH3)，3.29(2H，m，H-1′)，3.29(2H，m，H-1″)，1.73(3H，s，H-4′)，1.73(3H，s，H-4″)，1.66(3H，s，H-5′)，1.66(3H，s，H-5″).13C NMR(CD3OD)：δ155.1(C-12)，145.6(C-3)，145.6(C-5)，134.5(C-4)，134.1(C-1)，133.3(C-9)，129.3(C-3′)，129.3(C-3″)，128.7(C-10)，128.7(C-14)，124.8(C-2′)，124.8(C-2″)，118.5(C-2)，118.5(C-6)，114.7(C-11)，114.7(C-13)，59.6(C-4-OCH3)，36.1(C-8)，31.3(C-7)，24.7(C-1′)，24.7(C-1″)，24.5(C-5′)，16.8(C-4′)，16.8(C-4″).HM-E9-5-F3B-P1. 1 H NMR (CD 3 OD): δ6.99 (1H, d, J=8.4Hz, H-10), 6.99 (1H, d, J=8.4Hz, H- 14), 6.69 (1H, d, J=8.0Hz, H-11), 6.69 (1H, d, J=8.0Hz, H-13), 5.07 (1H, s, H-2′), 5.07 (1H , s, H-2″), 3.73 (3H, s, H-4-OCH 3 ), 3.29 (2H, m, H-1′), 3.29 (2H, m, H-1″), 1.73 (3H , s, H-4′), 1.73 (3H, s, H-4″), 1.66 (3H, s, H-5′), 1.66 (3H, s, H-5″). 13 C NMR (CD 3 OD): δ155.1(C-12), 145.6(C-3), 145.6(C-5), 134.5(C-4), 134.1(C-1), 133.3(C-9), 129.3( C-3'), 129.3(C-3"), 128.7(C-10), 128.7(C-14), 124.8(C-2'), 124.8(C-2"), 118.5(C-2) , 118.5(C-6), 114.7(C-11), 114.7(C-13), 59.6(C-4-OCH 3 ), 36.1(C-8), 31.3(C-7), 24.7(C- 1′), 24.7(C-1″), 24.5(C-5′), 16.8(C-4′), 16.8(C-4″).

HM-E9-5-F3B-P2.1H NMR(CD3OD)：δ6.79(1H，s，H-2′)，6.77(1H，d，J＝8.8Hz，H-6′)，6.64(1H，d，J＝8.0Hz，H-5′)，6.18(1H，s，，H-2)，5.28(1H，t，J＝7.2Hz，H-8)，5.04(1H，t，J＝5.6Hz，H-8′)，3.77(3H，s，H-4-OCH3)，3.26(2H，m，H-7)，3.26(2H，m，H-7′)，2.63(2H，s，H-α)，2.63(2H，s，H-α′)，1.73(3H，s，H-11)，1.72(3H，s，H-11′)，1.69(3H，s，H-10)，1.65(3H，s，H-10′).13C NMR(CD3OD)：δ152.6(C-4′)，147.8(C-5)，147.3(C-3)，136.1(C-1)，133.5(C-4)，132.9(C-3′)，131.3(C-9)，129.2(C-2′)，129.1(C-1′)，127.5(C-9′)，126.1(C-6′)，124.4(C-8)，122.8(C-8′)，118.1(C-6)，114.3(C-5′)，107.8(C-2)，59.5(C-4-OCH3)， 36.9(C-α′)，35.2(C-α)，27.8(C-7′)，24.6(C-7)，24.6(C-10)，24.3(C-10′)，16.8(C-11′)，16.5(C-11).HM-E9-5-F3B-P2. 1 H NMR (CD 3 OD): δ6.79 (1H, s, H-2'), 6.77 (1H, d, J=8.8Hz, H-6'), 6.64(1H, d, J=8.0Hz, H-5′), 6.18(1H, s,, H-2), 5.28(1H, t, J=7.2Hz, H-8), 5.04(1H, t , J=5.6Hz, H-8'), 3.77 (3H, s, H-4-OCH 3 ), 3.26 (2H, m, H-7), 3.26 (2H, m, H-7'), 2.63 (2H, s, H-α), 2.63 (2H, s, H-α′), 1.73 (3H, s, H-11), 1.72 (3H, s, H-11′), 1.69 (3H, s , H-10), 1.65 (3H, s, H-10′). 13 C NMR (CD 3 OD): δ152.6 (C-4′), 147.8 (C-5), 147.3 (C-3) , 136.1(C-1), 133.5(C-4), 132.9(C-3′), 131.3(C-9), 129.2(C-2′), 129.1(C-1′), 127.5(C- 9'), 126.1(C-6'), 124.4(C-8), 122.8(C-8'), 118.1(C-6), 114.3(C-5'), 107.8(C-2), 59.5 (C-4-OCH 3 ), 36.9(C-α′), 35.2(C-α), 27.8(C-7′), 24.6(C-7), 24.6(C-10), 24.3(C- 10'), 16.8(C-11'), 16.5(C-11).

HM-E9-5-F8A-P1.1H NMR(CD3OD)：δ7.50(1H，d，J＝1.9Hz，H-2′)，7.47(1H，dd，H-6′)，6.93(1H，d，J＝8.3Hz，H-5′)，6.60(1H，s，H-3)，6.48(1H，s，H-8)，5.24(1H，t，J＝7.2Hz，H-2″)，5.05(1H，t，J＝7.0Hz，H-6″)，3.96(3H，s，H-3′-OMe)，3.96(2H，s，J＝7.2Hz，H-1″)，2.05(2H，m，H-5″)，1.98(2H，m，H-4″)，1.78(3H，s，H-9″)，1.60(3H，s，H-10″)，1.55(3H，s，H-8″).13C NMR(CD3OD)：δ164.4(C-2)，162.3(C-5)，158.6(C-7)，155.8(C-9)，150.6(C-4′)，148.1(C-3′)，134.3(C-3″)，130.6(C-7″)，124.0(C-6″)，122.1(C-2″)，122.0(C-1′)，120.2(C-6′)，115.4(C-5′)，111.9(C-6)，109.2(C-2′)104.7(C-10)，102.7(C-3)，92.7(C-8)，55.2(C-O Me)，39.5(C-4″)，26.3(C-5″)，24.4(C-9″)，20.8(C-1″)，16.2(C-10″)，14.9(C-8″).HM-E9-5-F8A-P1. 1 H NMR (CD 3 OD): δ7.50 (1H, d, J=1.9Hz, H-2'), 7.47 (1H, dd, H-6'), 6.93(1H, d, J=8.3Hz, H-5′), 6.60(1H, s, H-3), 6.48(1H, s, H-8), 5.24(1H, t, J=7.2Hz, H-2″), 5.05 (1H, t, J=7.0Hz, H-6″), 3.96 (3H, s, H-3′-OMe), 3.96 (2H, s, J=7.2Hz, H- 1″), 2.05 (2H, m, H-5″), 1.98 (2H, m, H-4″), 1.78 (3H, s, H-9″), 1.60 (3H, s, H-10″ ), 1.55 (3H, s, H-8″). 13 C NMR (CD 3 OD): δ164.4 (C-2), 162.3 (C-5), 158.6 (C-7), 155.8 (C- 9), 150.6(C-4'), 148.1(C-3'), 134.3(C-3"), 130.6(C-7"), 124.0(C-6"), 122.1(C-2") , 122.0(C-1′), 120.2(C-6′), 115.4(C-5′), 111.9(C-6), 109.2(C-2′), 104.7(C-10), 102.7(C- 3), 92.7 (C-8), 55.2 (CO Me), 39.5 (C-4″), 26.3 (C-5″), 24.4 (C-9″), 20.8 (C-1″), 16.2 ( C-10″), 14.9 (C-8″).

HM-E9-5-F8A-P2.1H NMR(CD3OD)：δ6.39(1H，s，H-2)，6.14(1H，s，H-5′)，3.17(1H，d，J＝10.0Hz，H-1)，2.45(3H，s，H-4′-CH3)，2.16(2H，m，H-4)，1.90(2H，m，H-5)，1.66(3H，s，H-3-CH3)，1.42(3H，s，H-8)，1.07(3H，s，H-9).13C NMR(CD3OD)：δ158.4(C-6′)，140.8(C-4′)，132.7(C-3)，132.7(C-1′)，123.9(C-2)，112.1(C-5′)，109.3(C-3′)，77.9(C-7)，45.8(C-6)，33.4(C-1)，30.8(C-4)，26.4(C-8)，24.7(C-5)，22.8(C-4′-CH3)，22.1(C-3-CH3)，18.2(C-9).HM-E9-5-F8A-P2. 1 H NMR (CD 3 OD): δ6.39 (1H, s, H-2), 6.14 (1H, s, H-5′), 3.17 (1H, d, J=10.0Hz, H-1), 2.45(3H, s, H-4'-CH 3 ), 2.16(2H, m, H-4), 1.90(2H, m, H-5), 1.66(3H , s, H-3-CH 3 ), 1.42 (3H, s, H-8), 1.07 (3H, s, H-9). 13 C NMR (CD 3 OD): δ158.4 (C-6′ ), 140.8(C-4′), 132.7(C-3), 132.7(C-1′), 123.9(C-2), 112.1(C-5′), 109.3(C-3′), 77.9( C-7), 45.8(C-6), 33.4(C-1), 30.8(C-4), 26.4(C-8), 24.7(C-5), 22.8(C-4'- CH3 ) , 22.1 (C-3-CH 3 ), 18.2 (C-9).

HM-E9-7-S7-P1.1H NMR(CD3OD)：δ7.85(1H，s，H-2′)，7.72(1H，d，J＝8.4Hz，H-6′)，6.93(1H，d，J＝8.8Hz，H-5′)，6.43(1H，s，H-6)，5.24(1H，t，J＝6.8Hz，H-10)，3.93(3H，s，H-3′-OMe)，1.79(3H，s，H-12)，1.67(3H，s，H＝13).13CNMR(CD3OD)：δ162.1(C-7)，157.7(C-5)，154.8(C-8a)，148.4(C-3′)，147.4(C-4′)，146.1(C-2)，135.9(C-3)，130.6(C-11)，122.8(C-1′)，121.3(C-6′)，122.1(C-10)，114.9(C-5′)，111.1(C-2′)，110.9(C-4a)，103.0(C-8)，92.2(C-6)，55.1(C-3′-OMe)，24.6(C-12)，20.8(C-9)，16.5(C-13).HM-E9-7-S7-P1. 1 H NMR (CD 3 OD): δ7.85 (1H, s, H-2'), 7.72 (1H, d, J=8.4Hz, H-6'), 6.93(1H, d, J=8.8Hz, H-5′), 6.43(1H, s, H-6), 5.24(1H, t, J=6.8Hz, H-10), 3.93(3H, s, H-3′-OMe), 1.79 (3H, s, H-12), 1.67 (3H, s, H=13). 13 CNMR (CD 3 OD): δ162.1 (C-7), 157.7 (C -5), 154.8(C-8a), 148.4(C-3′), 147.4(C-4′), 146.1(C-2), 135.9(C-3), 130.6(C-11), 122.8( C-1'), 121.3(C-6'), 122.1(C-10), 114.9(C-5'), 111.1(C-2'), 110.9(C-4a), 103.0(C-8) , 92.2 (C-6), 55.1 (C-3′-OMe), 24.6 (C-12), 20.8 (C-9), 16.5 (C-13).

HM-E9-7-S10-P3.1H NMR(CD3OD)：δ7.84(1H，d，J＝8.8Hz，H-2′)，7.84(1H，d，J＝8.8Hz，H-6′)，6.93(1H，d，J＝8.8Hz，H-3′)，6.93(1H，d，J＝8.8Hz，H-5′)，6.58(1H，s，H-8)，6.49(1H，s，H-3)，5.24(1H，t，H-2″)，5.05(1H，t，J＝6.8Hz，H-6″)，3.96(2H，s，H-1″)，2.05(2H，m，H-5″)，1.98(2H，m，H-4″)，1.78(3H，s，H-9″)，1.60(3H，s，H-10″)，1.55(3H，s，H-8″).13C NMR(CD3OD)：δ164.5(C-6)，162.3(C-2)，161.2(C-4)，158.6(C-8)，155.8(C-3′)，134.3(C-3″)，130.6(C-7″)，130.6(C-5′)，124.0(C-6″)，122.1(C-2″)，122.0(C-4a)，115.6(C-2′)，115.6(C-4′)，111.9(C-5)，109.2(C-1′)，103.8(C-8a)，102.4(C-3)，92.7(C-7)，39.5(C-4″)，26.3(C-5″)，24.4(C-8″)，20.8(C-1″)，16.3(C-10″)，14.8(C-9″).HM-E9-7-S10-P3. 1 H NMR (CD 3 OD): δ7.84 (1H, d, J = 8.8Hz, H-2'), 7.84 (1H, d, J = 8.8Hz, H -6'), 6.93(1H, d, J=8.8Hz, H-3'), 6.93(1H, d, J=8.8Hz, H-5'), 6.58(1H, s, H-8), 6.49 (1H, s, H-3), 5.24 (1H, t, H-2″), 5.05 (1H, t, J=6.8Hz, H-6″), 3.96 (2H, s, H-1″ ), 2.05 (2H, m, H-5″), 1.98 (2H, m, H-4″), 1.78 (3H, s, H-9″), 1.60 (3H, s, H-10″), 1.55(3H, s, H-8″). 13 C NMR(CD 3 OD): δ164.5(C-6), 162.3(C-2), 161.2(C-4), 158.6(C-8) , 155.8(C-3′), 134.3(C-3″), 130.6(C-7″), 130.6(C-5′), 124.0(C-6″), 122.1(C-2″), 122.0 (C-4a), 115.6(C-2'), 115.6(C-4'), 111.9(C-5), 109.2(C-1'), 103.8(C-8a), 102.4(C-3) , 92.7(C-7), 39.5(C-4″), 26.3(C-5″), 24.4(C-8″), 20.8(C-1″), 16.3(C-10″), 14.8( C-9″).

HM-E13-F1-S11-P4.1H NMR(CDCl3)：δ6.54(1H，s，H-6)，6.44(1H，s，H-4)，4.79(1H，d，J＝7.2Hz，H-1″)，3.72(1H，s，H-10)，3.50-4.06(5H，s，H-2″，H-3″，H-4″，H-5″，H-6″)，2.81(1H，m，H-3)，2.63(H，s，H-4′)，2.24(H，m，H-2′)，2.05(H，m，H-2)，1.67(4H，m，H-2′，H-3′，H-5′，H-6′)，1.66(H，m，H-2)， 1.16(2H，m，H-3′，H-5′).13C NMR(CDCl3)：δ159.9(C-5)，155.1(C-7)，145.5(C-9)，132.0(C-8)，103.7(C-4)，101.9(C-1″)，101.2(C-6)，75.6(C-4′)，75.0(C-2″)，73.7(C-3″)，69.1(C-5″)，66.1(C-4″)，61.3(C-6″)，55.3(C-10)，48.1(C-1)，35.1(C-2)，31.0(C-3)，29.3(C-3′)，29.1(C-5′)，28.8(C-2′)，27.3(C-6′).HM-E13-F1-S11-P4. 1 H NMR (CDCl 3 ): δ6.54 (1H, s, H-6), 6.44 (1H, s, H-4), 4.79 (1H, d, J= 7.2Hz, H-1″), 3.72 (1H, s, H-10), 3.50-4.06 (5H, s, H-2″, H-3″, H-4″, H-5″, H- 6″), 2.81(1H, m, H-3), 2.63(H, s, H-4′), 2.24(H, m, H-2′), 2.05(H, m, H-2), 1.67(4H, m, H-2′, H-3′, H-5′, H-6′), 1.66(H, m, H-2), 1.16(2H, m, H-3′, H -5'). 13 C NMR (CDCl 3 ): δ159.9 (C-5), 155.1 (C-7), 145.5 (C-9), 132.0 (C-8), 103.7 (C-4), 101.9 (C-1″), 101.2 (C-6), 75.6 (C-4′), 75.0 (C-2″), 73.7 (C-3″), 69.1 (C-5″), 66.1 (C -4″), 61.3 (C-6″), 55.3 (C-10), 48.1 (C-1), 35.1 (C-2), 31.0 (C-3), 29.3 (C-3′), 29.1 (C-5'), 28.8(C-2'), 27.3(C-6').

HM-E13-F1-S13-P2.1H NMR(DMSO-d6)：δ13.16(1H，s，5-OH)，8.00(2H，d，J＝8.8Hz，H-2′，H-6′)，6.86(2H，d，J＝8.8Hz，H-3′，H-5′)，6.75(1H，s，H-3)，6.25(1H，s，H-6)，4.66(2H，d，J＝9.6Hz，H-1″)，3.32-3.83(5H，s，H-2″，H-3″，H-4″，H-5″，H-6″).13C NMR(DMSO-d6)：δ182.6(C-4)，164.4(C-2)，163.0(C-7)，161.6(C-4′)，160.9(C-9)，156.5(C-5)，129.4(C-2′，C-6′)，116.3(C-3′，C-5′)，105.1(C-8)，104.5(C-10)，103.6(C-3)，98.6(C-6)，82.3(C-5″)，79.1(C-1″)，73.8(C-2″)，71.3(C-3″)，70.9(C-4″)，61.7(C-6″).HM-E13-F1-S13-P2. 1 H NMR (DMSO-d 6 ): δ13.16 (1H, s, 5-OH), 8.00 (2H, d, J=8.8Hz, H-2′, H -6'), 6.86 (2H, d, J=8.8Hz, H-3', H-5'), 6.75 (1H, s, H-3), 6.25 (1H, s, H-6), 4.66 (2H, d, J=9.6Hz, H-1″), 3.32-3.83 (5H, s, H-2″, H-3″, H-4″, H-5″, H-6″). 13 C NMR (DMSO-d 6 ): δ182.6 (C-4), 164.4 (C-2), 163.0 (C-7), 161.6 (C-4′), 160.9 (C-9), 156.5 ( C-5), 129.4 (C-2′, C-6′), 116.3 (C-3′, C-5′), 105.1 (C-8), 104.5 (C-10), 103.6 (C-3 ), 98.6 (C-6), 82.3 (C-5″), 79.1 (C-1″), 73.8 (C-2″), 71.3 (C-3″), 70.9 (C-4″), 61.7 (C-6″).

HM-E13-F1-S13-P3P.1H NMR(CD3OD)：δ7.64(1H，d，J＝7.6Hz，H-6′)，7.54(1H，s，H-2′)，7.07(1H，d，J＝8.4Hz，H-5′)，6.57(1H，s，H-3)，6.26(1H，s，H-6)，5.00(1H，s，H-1″)，3.98(1H，s，4′-OCH3).13C NMR(DMSO-d6)：δ182.5(C-4)，164.2(C-2)，160.9(C-7)，156.5(C-9)，156.1(C-4′)，147.2(C-5)，147.1(C-3′)，123.9(C-6′)，119.6(C-1′)，114.0(C-2′，C-5′)，112.3(C-8)，105.0(C-10)，104.5(C-3)，103.6(C-6)，82.5(C-5″)，79.1(C-1″)，73.8(C-2″)，71.2(C-3″)，71.1(C-4″)，62.1(C-6″)，56.3(4′-OCH3).HM-E13-F1-S13-P3P. 1 H NMR (CD 3 OD): δ7.64 (1H, d, J=7.6Hz, H-6'), 7.54 (1H, s, H-2'), 7.07(1H, d, J=8.4Hz, H-5'), 6.57(1H, s, H-3), 6.26(1H, s, H-6), 5.00(1H, s, H-1") , 3.98 (1H, s, 4′-OCH 3 ). 13 C NMR (DMSO-d 6 ): δ182.5 (C-4), 164.2 (C-2), 160.9 (C-7), 156.5 (C -9), 156.1(C-4′), 147.2(C-5), 147.1(C-3′), 123.9(C-6′), 119.6(C-1′), 114.0(C-2′, C-5′), 112.3(C-8), 105.0(C-10), 104.5(C-3), 103.6(C-6), 82.5(C-5″), 79.1(C-1″), 73.8 (C-2″), 71.2 (C-3″), 71.1 (C-4″), 62.1 (C-6″), 56.3 (4′-OCH 3 ).

所述的化合物均由汉麻中分离所得。The compounds are all isolated from hemp.

还提供了上述化合物的分离方法，包括如下步骤：Also provided is the separation method of the above-mentioned compound, comprising the steps of:

S1、取11.8kg汉麻(HM)粉碎，用95％乙醇回流提取3次，料液比为1∶5， 回流时间2h；在40℃下减压浓缩，得浸膏约2Kg；浸膏用水分散，用乙酸乙酯萃取3次，浓缩蒸干得1kg浸膏；S1, get 11.8kg of hemp (HM) and pulverize, and extract 3 times with 95% ethanol under reflux, the ratio of solid to liquid is 1:5, and the reflux time is 2h; Concentrate under reduced pressure at 40°C to obtain about 2Kg of extract; water for extract Disperse, extract 3 times with ethyl acetate, concentrate and evaporate to dryness to obtain 1kg extract;

S2、取步骤S1所得的乙酸乙酯部位浸膏1K g，以1.2K g硅胶拌样，1.5Kg硅胶装柱，进行硅胶柱层析，柱体积6L，用石油醚/乙酸乙酯做洗脱剂进行梯度洗脱，洗脱梯度分别为50∶1，20∶1，10∶1，5∶1，3∶1，1∶1，0∶1，每个梯度收集两个馏分，每个馏分收集两个柱体积，所得各馏分通过LCMS分析检测，合并为4个组分，分别命名为HM-E2(石油醚/丙酮50∶1-20∶1)，HM-E7(石油醚/丙酮20∶1～10∶1)，HM-E9(石油醚/丙酮10∶1～1∶1)，HM-E13(石油醚/丙酮1∶1-0∶1)；S2. Take 1K g of the ethyl acetate part extract obtained in step S1, mix the sample with 1.2K g of silica gel, pack 1.5Kg of silica gel into a column, and perform silica gel column chromatography with a column volume of 6L, eluting with petroleum ether/ethyl acetate gradient elution, the elution gradients were 50:1, 20:1, 10:1, 5:1, 3:1, 1:1, 0:1, two fractions were collected for each gradient, and each fraction Two column volumes were collected, and each fraction obtained was analyzed and detected by LCMS, and combined into 4 components, which were named as HM-E2 (petroleum ether/acetone 50:1-20:1), HM-E7 (petroleum ether/acetone 20 :1～10:1), HM-E9 (petroleum ether/acetone 10:1～1:1), HM-E13 (petroleum ether/acetone 1:1-0:1);

S3、馏分HM-E2(石油醚/丙酮50∶1～20∶1)约100g，通过Flash(ODS C18)中压色谱柱层析和制备液相色谱等分离方法分离得到HM-E2-F4-P4；S3, about 100 g of fraction HM-E2 (petroleum ether/acetone 50:1～20:1), was separated by Flash (ODS C18) medium-pressure chromatographic column chromatography and preparative liquid chromatography to obtain HM-E2-F4- P4;

S4、馏分HM-E7(石油醚/丙酮20∶1～10∶1)约40g，通过Flash(ODS C18)中压色谱柱层析，凝胶柱层析和制备液相色谱等分离方法共分离得到HM-E7-F4-P3-1、HM-E7-F4-P4-1和HM-E7-F4-P7；S4, about 40 g of fraction HM-E7 (petroleum ether/acetone 20:1～10:1), was separated by Flash (ODS C18) medium-pressure column chromatography, gel column chromatography and preparative liquid chromatography and other separation methods HM-E7-F4-P3-1, HM-E7-F4-P4-1 and HM-E7-F4-P7 were obtained;

S5、馏分HM-E9(石油醚/丙酮10∶1～1∶1)约50g，通过Flash(ODS C18)中压色谱柱层析，凝胶柱层析和制备液相色谱等分离方法得到化合物HM-E9-5-F1B-P2，HM-E9-5-F3B-P1，HM-E9-5-F3B-P2，HM-E9-5-F8A-P1，HM-E9-5-F8A-P2，HM-E9-7-S7-P1，HM-E9-7-S10-P3；S5, about 50 g of fraction HM-E9 (petroleum ether/acetone 10:1～1:1), obtained the compound by separation methods such as Flash (ODS C18) medium pressure chromatographic column chromatography, gel column chromatography and preparative liquid chromatography HM-E9-5-F1B-P2, HM-E9-5-F3B-P1, HM-E9-5-F3B-P2, HM-E9-5-F8A-P1, HM-E9-5-F8A-P2, HM-E9-7-S7-P1, HM-E9-7-S10-P3;

S6、馏分HM-E13(石油醚/丙酮1∶1～0∶1)约40g，通过Flash(ODS C18)中压色谱柱层析，凝胶柱层析和制备液相色谱等分离方法得到化合物HM-E13-F1-S11-P4，HM-E13-F1-S13-P2，HM-E13-F1-S13-P3PS6, about 40 g of fraction HM-E13 (petroleum ether/acetone 1:1～0:1), obtained the compound by separation methods such as Flash (ODS C18) medium-pressure chromatography, gel column chromatography and preparative liquid chromatography HM-E13-F1-S11-P4, HM-E13-F1-S13-P2, HM-E13-F1-S13-P3P

以上所述仅是本发明的优选实施方式，应当指出，对于本技术领域的普通技术人员来说，在不脱离本发明原理的前提下，还可以作出若干改进和润饰，这些改进和润饰也应视为本发明的保护范围。The above is only a preferred embodiment of the present invention, it should be pointed out that for those of ordinary skill in the art, without departing from the principle of the present invention, some improvements and modifications can also be made, and these improvements and modifications should also be It is regarded as the protection scope of the present invention.

Claims (1)

1. the separation method of compound in a kind of Chinese fiber crops, it is characterised in that comprise the following steps：
S1, take the 11.8kg Chinese numb (HM), crush, extracted 3 times with 95% alcohol reflux, solid-liquid ratio 1: 5, return time 2h； It is concentrated under reduced pressure at 40 DEG C, obtains medicinal extract about 2Kg；Medicinal extract is water-dispersible, is extracted with ethyl acetate 3 times, and concentration is evaporated to obtain 1kg medicinal extract；
S2, ethyl acetate extract medicinal extract 1Kg obtained by step S1 is taken, with 1.2Kg silica gel mixed samples, 1.5Kg silica gel dress post, carry out silicon Plastic column chromatography, column volume 6L, make eluant, eluent with petrol ether/ethyl acetate and carry out gradient elution, gradient is respectively 50: 1,20 : 1,10: 1,5: 1,3: 1,1: 1,0: 1, each gradient collects two cuts, each two column volumes of fraction collection, and gained respectively evaporates Divide and detected by lcms analysis, merge into 4 components, 50: 1~20: 1 cut being collected into is named as HM-E2 respectively, by 20 : 1~10: 1 cut being collected into is named as HM-E7,10: 1~1: 1 cut being collected into is named as into HM-E9, by 1: 1~0: 1 The cut being collected into is named as HM-E13；
S3, cut HM-E2 are 100g, by pressing column chromatography and preparative liquid chromatography separation method isolated in Flash HM-E2-F4-P4, wherein, HM-E2-F4-P4 chemical formula is C20H26O4, structural formula is
S4, cut HM-E7 are 40g, by pressing column chromatography, gel filtration chromatography and preparative liquid chromatography separation side in Flash Method isolates to obtain HM-E7-F4-P3-1 and HM-E7-F4-P7；Wherein
HM-E7-F4-P3-1 chemical formula is C15H18O3, structural formula is
HM-E7-F4-P7 chemical formula is C20H24O4, structural formula is
S5, cut HM-E9 are 50g, by pressing column chromatography, gel filtration chromatography and preparative liquid chromatography separation side in Flash Method obtains compound HM-E9-5-F3B-P1, HM-E9-5-F3B-P2, HM-E9-5-F8A-P2, wherein, HM-E9-5-F3B-P1 Chemical formula be C25H32O4, structural formula is
HM-E9-5-F3B-P2 chemical formula is C25H32O4, structural formula is
HM-E9-5-F8A-P2 chemical formula is C18H22O4, structural formula is
S6, cut HM-E13 are 40g, by pressing column chromatography, gel filtration chromatography and preparative liquid chromatography separation side in Flash Method obtains compound HM-E13-F1-S11-P4, wherein, HM-E13-F1-S11-P4 chemical formula is C21H30O8, structural formula is：
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