CN103965157A - Preparation method for sesquiterpene lactone compound - Google Patents
Preparation method for sesquiterpene lactone compound Download PDFInfo
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Abstract
The invention discloses a preparation method for sesquiterpene lactone compound shown as a formula I. The preparation method comprises the following steps: abstracting, extracting, separating and the like, wherein the separation is that an extracting liquor is subject to column chromatography separation; the extracting liquor is further subject to gradient elution with eluents matched with the column chromatography; an elution flowing part obtained through a thin-layer chromatography is combined with the elution flowing part of two and a half times terpene lactone compound that contains a structure shown as the formula I, which is decompressed and concentrated to obtain a crude product; the crude product is dissolved in a non-polar organic solvent and subject to column chromatography separation for 1-3 times based on the previous method, and is eluted; the elution flowing part is concentrated and dried to obtain a pure product. According to the invention, the compound is obtained through abstracting and separating from valerian offcinalis for the first time; the compound obtained through the method has relatively high purity and yield.
Description
Technical field
The present invention relates to a kind of method that separates sesterterpene lactone compound of extracting from valerian.
Background technology
Valerian is the root and rhizome of Valerianaceae plant valerian (Valeriana offcinalis L.).The valerian medicinal material beginning is loaded in " medicinal herbs among the people of science ", the effect of have spasmolysis, pain relieving and calmness, calming the nerves; To wound, confused and worried, palpitation and insomnia, dysmenorrhoea, through closing, the disease such as rheumatic arthralgia can play certain therapeutic action.Valerian, containing iridoids, sesquiterpenoids, alkaloids, lignanoids, flavonoid activeconstituents, is mainly good natural pharmaceutical resources.It extensively records in pharmacopoeia of each country, and the early stage pharmacopeia of China and the local drug standard were also once recorded.
We conduct in-depth research valerian chemical composition, from valerian, extract and isolate a kind of new sesterterpene lactone compound, and this series of compounds separates and obtains first from valerian.
Summary of the invention
The object of this invention is to provide a kind of preparation method of sesterterpene lactone compound, this compound is from valerian, to extract to separate first to obtain, and the structure of compound is suc as formula shown in I:
The method comprises the following steps:
1) extract: get the valerian medicinal material crushing, with organic solvent extraction;
2) extraction: with non-polar organic solvent extraction, collect extraction liquid after extracting solution is concentrated;
3) separate: extraction liquid is carried out to column chromatography separation, and use the eluent adapting with this column chromatography to carry out gradient elution, the wash-out stream part obtaining with tlc inspection, then merge and contain the wash-out stream part of structure suc as formula the sesterterpene lactone compound shown in I, after concentrating under reduced pressure, obtain crude product, after crude product is dissolved with non-polar organic solvent, carry out again 1-3 column chromatography by preceding method and separate, wash-out, wash-out stream part is concentrated to the dry sterling that obtains.
Adopt the ordinary method that can grasp of those skilled in the art to extract valerian medicinal material, as methods such as dipping, thermal backflow, ultrasonic, seepages.Extract the organic solvent adopting and comprise ethyl acetate, butylacetate, ether, chloroform, sherwood oil, ethanol etc., the preferred organic solvent of the present invention is 50-90% (weight percent) aqueous ethanolic solution, this solvent not only cost is low, safe, and the target component rate of transform (in extract, target component total amount accounts for the ratio of target component total amount in medicinal material) of extracting is the highest, and the rate of transform is higher, illustrate that extraction is more abundant.
Preferred column chromatography filler is silica gel, and further preferably adopting particle diameter is 200-300 object silica gel.
Preferably, step 3) described in the double solvents that formed by sherwood oil (60-90 DEG C) and ethyl acetate of eluent, in described double solvents, the volume percent of ethyl acetate is 1-5%, the best is 1-2%.Thin layer test shows: adopt the separating effect of this eluent impurity and target component best (seeing accompanying drawing 8-12).
Further preferred, step 3) in, extraction liquid is carried out to column chromatography separation, the sherwood oil that is first 99: 1 by volume ratio (60-90 DEG C) and ethyl acetate double solvents wash-out, the wash-out stream part obtaining with tlc inspection, in the time occurring structure suc as formula compound shown in I in wash-out stream part, the sherwood oil that is 98: 2 by volume ratio again (60-90 DEG C) and ethyl acetate double solvents wash-out, merge and contain the wash-out stream part of structure suc as formula the sesterterpene lactone compound shown in I, after concentrating under reduced pressure, obtain crude product, after crude product is dissolved with non-polar organic solvent, carrying out 1-3 column chromatography by preceding method separates again, wash-out, wash-out stream part is concentrated, the dry sterling that obtains.
Preferably, before being also included in and extracting, first extracting solution is carried out to the step of wash-out, purifying by macroporous adsorptive resins.Increase after this step, can not only further improve the purity of product, also help the time cycle that shortens whole techniques.
Preferably, described non-polar organic solvent is sherwood oil or normal hexane or hexanaphthene.
The invention has the beneficial effects as follows:
1) adopt the method can from valerian, obtain first a kind of new sesterterpene lactone compound.
2) the sesterterpene lactone compound purity and the yield that adopt the method to obtain are high, and wherein purity is more than 98%, and the rate of transform can reach 60% left and right.
3) the method technique is simple, and the cycle is short, and production cost is low, easily realizes industrialized production.
Brief description of the drawings
Fig. 1 is the high-efficient liquid phase chromatogram of the compounds of this invention in embodiment 1.
Fig. 2 is 6,24 H-HMBC fragment Correlated Spectroscopies of the compounds of this invention.
Fig. 3 is 2,23 H-HMBC fragment Correlated Spectroscopies of the compounds of this invention.
Fig. 4 is 20 CH of the compounds of this invention
3-HMBC fragment Correlated Spectroscopy.
Fig. 5 is 11 CH of the compounds of this invention
3-HMBC fragment Correlated Spectroscopy.
Fig. 6 is 16 CH of the compounds of this invention
3-HMBC fragment Correlated Spectroscopy.
Fig. 7 is 2,4,7 H-HMBC fragment Correlated Spectroscopies of the compounds of this invention.
Fig. 8 is taking sherwood oil (60-90 DEG C) and the thin-layer chromatography photo of ethyl acetate (98: 2) as developping agent.
Fig. 9 is taking sherwood oil (60-90 DEG C) and the thin-layer chromatography photo of butylacetate (98: 2) as developping agent.
Figure 10 is the thin-layer chromatography photo taking normal hexane and ethyl acetate (98: 2) as developping agent.
Figure 11 is taking sherwood oil (60-90 DEG C) and the thin-layer chromatography photo of ethyl acetate (99: 1) as developping agent.
Figure 12 is taking sherwood oil (60-90 DEG C) and the thin-layer chromatography photo of ethyl acetate (95: 5) as developping agent.
Embodiment
With specific embodiment, the present invention will be further described below, but protection scope of the present invention is not limited to this.
Embodiment 1
A preparation method for sesterterpene lactone compound, step is as follows:
1) extract: get valerian medicinal material 20kg, after pulverizing, by 50% ethanol (referring to that weight content is 50% aqueous ethanolic solution) refluxing extraction 2 times, each 2 hours, each ethanol consumption was 120Kg.
2) extraction: merging ethanol extract and being evaporated to relative density is 1.20 clear cream, then adds n-hexane extraction, collects n-hexane extract.
3) separate: take 200-300 order silica gel 700g, dry column-packing, by sherwood oil (60-90 DEG C) wash-out balance, crosses silica gel chromatographic column using above-mentioned extraction liquid as sample solution, and the effective constituent of sample solution is adsorbed on silica gel completely.Then the sherwood oil that is first 99: 1 by volume ratio (60-90 DEG C) and ethyl acetate double solvents wash-out, under 254nm UV-light, check the wash-out stream part obtaining by tlc, the developping agent using in thin-layer chromatography is sherwood oil: ethyl acetate (7:1).In the time there is target compound component in wash-out stream part, use volume ratio instead and be the sherwood oil (60-90 DEG C) of 98: 2 with ethyl acetate double solvents as eluent wash-out, to wash-out stream part, can't detect target compound component, merge the wash-out stream part of 98:2, concentrated with Rotary Evaporators, obtain crude product;
Crude product is separated with carrying out 2 column chromatographys by preceding method after n-hexane dissolution again, and wash-out, obtains sterling after wash-out stream part is concentrated, is dried.
Detect through HPLC, the purity of product is 98.8%, output is 5.39g, because structure in valerian medicinal material is 0.045% suc as formula the content of the sesterterpene lactone compound shown in I, calculates thus the rate of transform and is: 5.39*98.8%/20000*0.045%=59.2%.
Production cycle is 88 hours.
The testing conditions of high performance liquid chromatography is: ODS24.6*250mm, 5 μ m analytical columns; Column temperature: 30 DEG C; Moving phase: acetonitrile-deionized water (70:30, V/V), flow velocity: 0.6ml/min, detects wavelength 268nm, sample size 20ul.
Structural Identification and the parsing of embodiment 2 compounds
1) faint yellow oily matter.
2) UV (λ
meOH max) in spectrum, 269nm, has illustrated that conjugate system exists.
3)IR(νmax
KBr)cm
-1：3443.84,2929.24,2871.71,1735.32,1677.59,1622.83,1453.35,1376.10；
In this structure of above data declaration, there is the functional groups such as methyl, methylene radical, carbonyl, ethylene linkage.
4)EI-MS(me/z)：291.29，279.25，263.31，234.16，219.04(100％)，204.98，190.95，178.96，173.06，148.92，144.99，130.92，119.11，107.15，104.92，90.99，76.95，64.99，54.94；
MALDI-TOF MS(me/z)：315.1，299.1，273.0，257.0，235.0。
In spectrum, 219.04 (100%), but do not provide molecular ion peak.
5)
1H-NMR(CDCL
3，500MHz)δppm：9.28(s，1H)，6.35(d，J＝9.5Hz，1H)，5.35(dd，J＝5.5Hz，J＝11.5Hz，2H)，4.18(d，J＝12.0Hz，1H)，4.15(d，J＝12.0Hz，1H)，2.91(m，1H)，2.85(dd，1H)，2.26(m，1H，C14-H)，2.02(t，2H，C12-H)，2.00(s，3H)，1.28(s，3H，C20-CH
3)，1.18(s，3H，C11-CH
3)，1.19(s，3H，C11-CH
3)，1.02(s，3H，C16-CH
3)，1.03(s，3H，C16-CH
3)；
In spectrum, 9.28ppm place, provides the signal at the s peak of a H, is 24 aldehyde radical H signals; 6.35ppm place, provides a H, and the d peak-to-peak signal that coupling constant is 9.5Hz is 6 alkene H signals; 5.35ppm place, provides a H, and coupling constant is respectively 5.5, the dd peak-to-peak signal of 11.5Hz, is 2 alkene H signals; 4.18ppm place, provides a H, and coupling constant is respectively the d peak-to-peak signal of 12.0Hz, is 23 H signals; 4.12ppm place, provides a H, and coupling constant is respectively the d peak-to-peak signal of 12.0Hz, is 23 H signals; 2.88ppm place, provides a H, and m peak-to-peak signal is 13 H signals; 2.84ppm place, provides a H, and coupling constant is respectively the dd peak-to-peak signal of 12.0Hz, is 4 H signals; 2.02ppm place, provides 3 H, s peak-to-peak signal, for-OCOCH
3group H signal; 1.28ppm place, provides 3 H, and s peak-to-peak signal is 20 CH
3group H signal; 1.19ppm place, provides 3 H, s peak-to-peak signal, be 11 together with CH
3group H signal; 1.18ppm place, provides 3 H, s peak-to-peak signal, be 11 together with CH
3group H signal; 1.03ppm place, provides 3 H, s peak-to-peak signal, be 16 together with CH
3group H signal; 1.02ppm place, provides 3 H, s peak-to-peak signal, be 16 together with CH
3group H signal;
6)
13c-NMR (CDCL
3, 125MHz) and δ ppm:193.80 (d, C-24, aldehyde radical carbon), 170.89 (s ,-OCOCH3, middle acyl group carbon), 175.32 (s, C-22 ,-O-C=O), 155.88 (d, C-6 ,=CH), 142.64 (
s, C-5 ,=C-), 132.94 (s, C-1 ,=C-), 130.23 (d, C-2 ,=CH), 85.59 (s, C-20 ,-O-C-), 60.76 (t, C-23 ,-OCH
2), 48.87 (d, C-13 ,-C-COO), 41.37 (d, C-19 ,-CH-), 40.65 (t, C-21 ,-CH
2-), 40.43 (d, C-14 ,-CH-), 37.01 (d, C-8 ,-CH-), 35.03 (d, C-10 ,-CH
2), 29.85 (q, C20-CH
3), 29.05 (s, C11), 28.52 (q, C11-CH
3), 28.38 (q, C16-CH
3), 27.77 (t, C-3 ,-CH
2), 26.52 (t, C-7 ,-CH
2), 25.31,24.38 (t, C-9 ,-CH
2), 23.94 (d, C-17 ,-CH), 23.75 (t, C-18 ,-CH
2), 23.31 (t, C-4 ,-CH
2), 21.07 (t, C-15 ,-CH
2), 20.96 (q, C-23-OCOCH
3), 20.55 (t, C-12 ,-CH
2), 15.86 (q, C11-CH
3), 15.81 (q, C16-CH
3);
In spectrum, provide 31 signals, wherein 193.80 (d, C-24, aldehyde radical carbon), 170.89 (s ,-OCOCH3, middle acyl group carbon), 175.32 (s, C-22 ,-O-C=O) signal is very weak, is carbonyl carbon signal; 155.88 (d, C-6 ,=CH) are quaternary carbon signal for containing H proton signal and 142.64 (s, C-5 ,=C-), and the two is carbon signal on the two keys of ethylene linkage, and has conjugate system with group; 132.94 (s, C-1 ,=C-) be quaternary carbon signal and 130.23 (d, C-2 ,=CH) for containing H proton signal, the two is carbon signal on the two keys of ethylene linkage; 85.59 (s, C-20 ,-O-C-) are oxygen containing saturated quaternary carbon signal, 60.76 (t, C-23 ,-OCH
2) be oxygen containing saturated secondary carbon signal; The tertiary carbon signal of 48.87 (d, C-13 ,-C-COO) for containing electron-withdrawing group; 41.37 (d, C-19 ,-CH-), 40.65 (t, C-21 ,-CH
2-), 40.43 (d, C-14 ,-CH-), 37.01 (d, C-8 ,-CH-), 35.03 (d, C-10 ,-CH
2), 29.85 (q, C20-CH
3) be primary carbon signal, 29.05 (s, C11), 28.52 (q, C11-CH
3) be primary carbon signal, 28.38 (q, C16-CH
3) be primary carbon signal, 27.77 (t, C-3 ,-CH
2), 26.52 (t, C-7 ,-CH
2), 25.31,24.38 (t, C-9 ,-CH
2), 23.94 (d, C-17 ,-CH), 23.75 (t, C-18 ,-CH
2), 23.31 (t, C-4 ,-CH
2), 21.07 (t, C-15 ,-CH
2), 20.96 (q, C-23-OCOCH
3) be primary carbon signal, 20.55 (t, C-12 ,-CH
2), 15.86 (q, C11-CH
3) be primary carbon signal, 15.81 (q, C16-CH
3) be primary carbon signal.
7) in H-H cosy spectrum, provide 6.35 (d, J=9.5Hz, 1H, C6-H) and 1.48 (m, 1H), 5.35 (dd, J=5.5Hz, J=11.5Hz, 1H, C2-H) and 2.36,2.00,2.88,2.84 (dd, 1H, C4-H) and 5.35 (dd, J=5.5Hz, J=11.5Hz, 1H, C2-H), 2.91 (m, 1H, C13-H) and 2.26 (m, 1H, C14-H), 2.02 (t, 2H, C12-H) exist and be correlated with.
8) in HMQC spectrum, provide 9.28 (s, 1H) and 193.80 (d, C-24, aldehyde radical carbon), 6.35 (d, J=9.5Hz, 1H) and 155.88 (d, C-6 ,=CH), 5.35 (dd, J=5.5Hz, J=11.5Hz, 2H) and 130.23 (d, C-2 ,=CH), 4.18 (d, J=12.0Hz, 1H) and 4.12 (d, J=12.0Hz, 1H) with 60.76 (t, C-23 ,-OCH
2), 2.91 (m, 1H) and 48.87 (d, C-13 ,-CH-COO), 2.85 (dd, 1H) and 23.94 (d, C-17 ,-CH), 2.00 (s, 3H) and 20.96 (q, C-23-OCOCH
3), 1.02 (s, 3H) and 15.81 (q, C16-CH
3), 1.03 (s, 3H) and 28.38 (q, C16-CH
3), 1.18 (s, 3H) and 15.86 (q, C11-CH
3), 1.19 (s, 3H) and 28.52 (q, C11-CH
3), 1.28 (s, 3H) and 29.85 (q, C20-CH
3) etc. be connected.
9) in HMBC spectrum, provide 9.28 (s, 1H) and 155.88 (d, C-6 ,=CH), 142.64 (s, C-5 ,=C-), 23.31 (t, C-4 ,-CH
2) relevant; 6.35 (d, J=9.5Hz, 1H) and 193.80 (d, C-24, aldehyde radical carbon), 142.64 (s, C-5 ,=C-), 23.31 (t, C-4 ,-CH
2) relevant, to sum up derive following fragment, see Fig. 2.5.35 (dd, J=5.5Hz, J=11.5Hz, 1H) and 60.76 (t, C-23 ,-OCH
2), 35.03 (t, C-10 ,-CH
2-), 27.77 (t, C-3 ,-CH
2) relevant; 4.18 (d, J=12.0Hz, 1H) and 4.12 (d, J=12.0Hz, 1H) and 170.89 (
s,-OCOCH3, middle acyl group carbon), 130.23 (d, C-2 ,=CH), 35.03 (t, C-10 ,-CH
2-) relevant, to sum up derive following fragment, see Fig. 3.2.91 (m, 1H) and 26.52 (t, C-12 ,-CH
2-) relevant; 1.28 (s, 3H, C20-CH
3) and 41.37 (d, C-19 ,-CH-), 40.65 (t, C-21 ,-CH
2-), 85.59 (s, C-20 ,-O-C-) are relevant, to sum up derive following fragment, see Fig. 4.1.18 (s, 3H, C11-CH
3) and 1.19 (s, 3H, C11-CH
3) and 37.01 (d, C-8 ,-CH-), 20.55 (t, C-12 ,-CH
2), 29.05 (s, C11), relevant, to sum up derive following fragment, see Fig. 5.1.02 (s, 3H, C16-CH
3) and 1.03 (s, 3H, C16-CH
3) and 21.07 (t, C-15 ,-CH
2), 23.94 (d, C-17 ,-CH),, relevant, to sum up derive following fragment, see Fig. 6.27.77 (t, C-3 ,-CH
2) and 5.35 (dd, J=5.5Hz, J=11.5Hz, 1H), 2.84 (dd, 1H, C4-H) relevant, 1.48 (m, 1H) and 142.64 (s, C-5 ,=C-), 37.01 (d, C-8 ,-CH-) relevant, to sum up and in conjunction with H-H cosy compose, derive following fragment, see Fig. 7.
Comprehensive above analysis, show that its molecular formula is C
31h
46o
5, confirm this compound structure as shown in Equation 1, this structure is that 2 sesquiterpenes link together, one of them,, for the sesquiterpene lactones structure of variation, meets isoprene rule from source of students approach.
Embodiment 3
A preparation method for sesterterpene lactone compound, step is as follows:
1) extract: get valerian medicinal material 20kg, after pulverizing, carry out diacolation with 200Kg85% ethanol, collect percolate;
2) purifying: by D101 macroporous adsorptive resins on percolate, first use the pure water rinsing removal of impurity, then use 80% ethanol elution of 4 times of column volumes, collect elutriant.
3) extraction: by extracting with sherwood oil (60-90 DEG C) after elutriant concentrating under reduced pressure, collect extraction liquid;
4) separate: take 200-300 order silica gel 500g dry column-packing, wash-out balance, above-mentioned extraction liquid is crossed to silica gel chromatographic column as sample solution, the sherwood oil (60-90 DEG C) that is first 1% by the volume ratio of ethyl acetate and ethyl acetate double solvents wash-out, the wash-out stream part obtaining with tlc inspection, in the time occurring structure suc as formula compound shown in I in wash-out stream part, the sherwood oil (60-90 DEG C) that is 2% by the volume ratio of ethyl acetate again and ethyl acetate double solvents wash-out, merge and contain the wash-out stream part of structure suc as formula the sesterterpene lactone compound shown in I, after concentrating under reduced pressure, obtain crude product, after sherwood oil for crude product (60-90 DEG C) is dissolved, carrying out 2 column chromatographys by preceding method separates again, wash-out, wash-out stream part is concentrated, the dry sterling that obtains.
Detect through HPLC, the purity of product is 99.3%, and output is 5.74g, calculates the rate of transform to be: 5.74*99.3%/20000*0.045%=63.3%.
Production cycle is 56 hours.
Claims (9)
1. structure, suc as formula a preparation method for the sesterterpene lactone compound shown in I, is characterized in that comprising the following steps:
1) extract: get the valerian medicinal material crushing, with organic solvent extraction;
2) extraction: with non-polar organic solvent extraction, collect extraction liquid after extracting solution is concentrated;
3) separate: extraction liquid is carried out to column chromatography separation, and use the eluent adapting with this column chromatography to carry out gradient elution, the wash-out stream part obtaining with tlc inspection, then merge and contain the wash-out stream part of structure suc as formula the sesterterpene lactone compound shown in I, after concentrating under reduced pressure, obtain crude product, after crude product is dissolved with non-polar organic solvent, carry out again 1-3 column chromatography by preceding method and separate, wash-out, wash-out stream part is concentrated to the dry sterling that obtains
2. preparation method as claimed in claim 1, is characterized in that: step 1) described in extraction refer to that dipping extracts or thermal backflow extraction or supersound extraction or seepage are extracted.
3. preparation method as claimed in claim 1, is characterized in that: step 1) described in organic solvent be 50-90% aqueous ethanolic solution.
4. preparation method as claimed in claim 1, is characterized in that: the filler of described column chromatography is that particle diameter is 200-300 object silica gel.
5. preparation method as claimed in claim 1, is characterized in that: step 3) described in the double solvents that formed by sherwood oil (60-90 DEG C) and ethyl acetate of eluent, in described double solvents, the volume ratio of ethyl acetate is 1-5%.
6. preparation method as claimed in claim 5, it is characterized in that: step 3) in, extraction liquid is carried out to column chromatography separation, the sherwood oil (60-90 DEG C) that is first 1% by the volume ratio of ethyl acetate and ethyl acetate double solvents wash-out, the wash-out stream part obtaining with tlc inspection, in the time occurring structure suc as formula compound shown in I in wash-out stream part, the sherwood oil (60-90 DEG C) that is 2% by the volume ratio of ethyl acetate again and ethyl acetate double solvents wash-out, merge and contain the wash-out stream part of structure suc as formula the sesterterpene lactone compound shown in I, after concentrating under reduced pressure, obtain crude product, after crude product is dissolved with non-polar organic solvent, carrying out 1-3 column chromatography by preceding method separates again, wash-out, wash-out stream part is concentrated, the dry sterling that obtains.
7. preparation method as claimed in claim 1, is characterized in that: before being also included in and extracting, first extracting solution is carried out to the step of wash-out, purifying by macroporous adsorptive resins.
8. as the preparation method of claim 1-7 as described in any one, it is characterized in that: described non-polar organic solvent is sherwood oil or normal hexane or hexanaphthene.
Valerian preparation structure suc as formula the purposes in the sesterterpene lactone compound shown in I,
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