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

Chinese fiber crops compound and its separation method
Technical field
The present invention relates to the seven kinds of noval chemical compounds and its separation method that identification is separated from Chinese sesame slices.
Background technology
Chinese fiber crops (Cannabis sativa L.) are Cannabaceae (Cannabaceae) Cannabis (Cannabis) plant.Again Name hemp, fire fiber crops, tremble with fear fiber crops etc., and there are cultivation, aboundresources in all parts of the country.Chinese anaesthetic with a long history,《Compendium of Materia Medica》In have The record being used as medicine on Chinese fiber crops, sesame slices, fried dough twist, snippings extract can be used as medicine, and have anesthesia, cough-relieving Zhichuan, relieving spasm and pain, styptic powder Become silted up, detoxify it is antiabortive and other effects；Its ripening fruits fructus cannabis is mild-natured, sweet, has the effect such as promoting blood circulation, moisturize laxation, defaecation, for controlling Treat the disease such as blood deficiency and depleted fluid, dry constipation of intestines, irregular menstruation；Modern pharmacology research shows that Chinese fiber crops also have antibacterial, radioresistance, resist The effect such as oxidation, anti-asthma, anticancer.Find that Chinese fiber crops chemical composition species is various, successively therefrom separates through consulting lot of documents To a variety of chemical compositions such as cannabinoids, flavonoids, terpene, steroid, esters.
At present, the chemical composition in Chinese fiber crops plant is altogether more than 537, and cannabinoids material is a total of more than 109, Cannabinoids material is also the compound of most study, especially main psychoactive drug substance THC (Tetrahydrocannabinol, THC), but studies have shown that also has some other cannabinoids materials also to have necessarily Pharmacological activity, such as, the cannabidiol (Cannabidiol, CBD) without psychotropic activity also shows to relieve pain, anti-spirit The pharmacological properties such as activity, anti-spasm, neuroprotection, antiemetic[12].The compound of non-cannabinoids has a flavonoids, terpene, steroid, Esters, carbohydrate and its related compound, hydrocarbon, containing nitrogen compound, amino acid etc..
The content of the invention
The present invention is intended to provide the seven kinds of noval chemical compounds and its separation method that are separated from Chinese fiber crops.
To achieve the above object, the technical scheme taken of the present invention is：
The compound C of Formulas I15H18O3
The compound C of Formula II21H30O8
The compound C of formula III20H26O4
The compound C of formula IV18H22O4
The compound C of Formula VII20H24O4
The compound C of Formula VIII25H32O4
The compound C of Formula IX25H32O4
Described noval chemical compound is by separating obtained in Chinese fiber crops.
The embodiment of the present invention additionally provides the separation method of above-mentioned noval chemical compound, comprises 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 1K g obtained by step S1 are taken, with 1.2K g silica gel mixed samples, 1.5Kg silica gel dress post, Silica gel column chromatography is carried out, column volume 6L, eluant, eluent is made with petrol ether/ethyl acetate and carries 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, institute Obtain each cut to detect by lcms analysis, merge into 4 components, be respectively designated 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, cut HM-E2 (petroleum ether/acetone 50: 1~20: 1) about 100g, pass through pressure chromatogram in Flash (ODS C18) The isolated HM-E2-F4-P4 of the separation method such as column chromatography and preparative liquid chromatography；
S4, cut HM-E7 (petroleum ether/acetone 20: 1~10: 1) about 40g, pass through pressure chromatographic column in Flash (ODS C18) Chromatography, the separation method such as gel filtration chromatography and preparative liquid chromatography isolate to obtain HM-E7-F4-P3-1, HM-E7-F4-P4-1 And HM-E7-F4-P7；
S5, cut HM-E9 (petroleum ether/acetone 10: 1~1: 1) about 50g, pass through pressure chromatographic column in Flash (ODS C18) Chromatography, the separation method such as gel filtration chromatography and preparative liquid chromatography obtain compound 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, cut HM-E13 (petroleum ether/acetone 1: 1~0: 1) about 40g, pass through pressure chromatographic column in Flash (ODS C18) Chromatography, the separation method such as gel filtration chromatography and preparative liquid chromatography obtain compound HM-E13-F1-S11-P4, HM-E13-F1- S13-P2, HM-E13-F1-S13-P3P.
Present invention separation from Chinese sesame slices identifies 7 kinds of noval chemical compounds, improves the comprehensive utilization ratio of Chinese fiber crops.
Embodiment
In order that objects and advantages of the present invention are more clearly understood, enter traveling one to the present invention with reference to embodiments Step describes in detail.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not used to limit this hair It is bright.
The embodiments of the invention provide compound：HM-E7-F4-P3-1,5-methoxy-2,3,2 ', 3 '- Tetrahydro-2H-2 ', 4 ' a-ethanoindeno [7,4-bc] oxepin-2-ol, C15H18O3, its structural formula is as follows：
Compound：HM-E13-F1-S11-P4,7-hydroxy-5-methoxyindan-1-spiro-cyclohexan- 4 '-O- β-D-glucopyranose, C21H30O8Its structural formula is as follows：
Compound：HM-E2-F4-P4,4 '-n-propyl-tetrahydrocannabinoic acid, C20H26O4, it is tied Structure formula is as follows：
Compound：HM-E9-5-P8A-P2,4 '-methyl-tetrahydrocannabinoic acid, C18H22O4, its Structural formula is as follows：
Compound：HM-E7-F4-P7,7,8-dihydro-3,5,4 '-trihydroxy-4-methoxy-3 '- Isopentenylstilbene, C20H24O4, its structural formula is as follows：
Compound：HM-E9-5-F3B-P1, α, α '-dihydro-3,5,4 '-trihydroxy-4-methoxy-2,6- Diisopentenylstilbene, C25H32O4, its structural formula is as follows：
Compound：HM-E9-5-F3B-P2, α, α '-dihydro-3,5,4 '-trihydroxy-4-methoxy-6,3 '- Diisopentenylstilbene, C25H32O4, its structural formula is as follows：
Wherein, the spectral data of above-claimed cpd is：
HM-E2-F4-P4.1H NMR(CDCl3)：δ 6.37 (1H, s, H-2), 6.24 (1H, s, H-5 '), 3.22 (1H, d, J =10.8Hz, H-1), a), 2.75 2.90 (1H, m, H-1 " (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-E7-F4-P3-1.1H NMR(CD3OD)：δ 6.21 (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)：δ 159.9 (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)：δ 1.98 (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)：δ 173.1 (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)：δ 6.79 (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 ')13C NMR(CD3OD)：δ 152.6 (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)：δ 6.79 (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)：δ 152.8 (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)：δ 6.99 (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)：δ 155.1 (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-P2.1H NMR(CD3OD)：δ 6.79 (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)：δ 152.6 (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-F8A-P1.1H NMR(CD3OD)：δ 7.50 (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)：δ 164.4 (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), and 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-P2.1H NMR(CD3OD)：δ 6.39 (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)：δ 158.4 (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-E9-7-S7-P1.1H NMR(CD3OD)：δ 7.85 (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)：δ 162.1 (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)：δ 7.84 (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)：δ 164.5 (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)：δ 6.54 (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)：δ 159.9 (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)：δ 13.16 (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)：δ 182.6 (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)：δ 7.64 (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 "), The 3.98 (- OCH of 1H, s, 4 '3).13C NMR(DMSO-d6)：δ 182.5 (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).
Described compound is by separating obtained in Chinese fiber crops.
The separation method of above-claimed cpd is additionally provided, is comprised the following steps：
S1, take the 11.8kg Chinese numb (HM) to 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 1K g obtained by step S1 are taken, with 1.2K g silica gel mixed samples, 1.5Kg silica gel dress post, Silica gel column chromatography is carried out, column volume 6L, eluant, eluent is made with petrol ether/ethyl acetate and carries 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, institute Obtain each cut to detect by lcms analysis, merge into 4 components, be respectively designated 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, cut HM-E2 (petroleum ether/acetone 50: 1~20: 1) about 100g, pass through pressure chromatogram in Flash (ODS C18) The isolated HM-E2-F4-P4 of the separation method such as column chromatography and preparative liquid chromatography；
S4, cut HM-E7 (petroleum ether/acetone 20: 1~10: 1) about 40g, pass through pressure chromatographic column in Flash (ODS C18) Chromatography, the separation method such as gel filtration chromatography and preparative liquid chromatography isolate to obtain HM-E7-F4-P3-1, HM-E7-F4-P4-1 And HM-E7-F4-P7；
S5, cut HM-E9 (petroleum ether/acetone 10: 1~1: 1) about 50g, pass through pressure chromatographic column in Flash (ODS C18) Chromatography, the separation method such as gel filtration chromatography and preparative liquid chromatography obtain compound 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, cut HM-E13 (petroleum ether/acetone 1: 1~0: 1) about 40g, pass through pressure chromatographic column in Flash (ODS C18) Chromatography, the separation method such as gel filtration chromatography and preparative liquid chromatography obtain compound HM-E13-F1-S11-P4, HM-E13-F1- S13-P2, HM-E13-F1-S13-P3P
Described above is only the preferred embodiment of the present invention, it is noted that for the ordinary skill people of the art For member, under the premise without departing from the principles of the invention, some improvements and modifications can also be made, these improvements and modifications also should It is considered as 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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