CN101935332A - Preparation method and application of 5,7,4'-trihydroxyl8-methoxyl-3-O-alpha-L-rhamnoside and active composition thereof - Google Patents
Preparation method and application of 5,7,4'-trihydroxyl8-methoxyl-3-O-alpha-L-rhamnoside and active composition thereof Download PDFInfo
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Abstract
The invention belongs to the technical field of medicines and relates to 5,7,4'-trihydroxyl8-methoxyl-3-O-alpha-L-rhamnoside as well as a preparation method and application thereof. The 5,7,4'-trihydroxyl8-methoxyl-3-O-alpha-L-rhamnoside is in a structure disclosed in the specification. The invention also provides a preparation method of 5,7,4'-trihydroxyl8-methoxyl-3-O-alpha-L-rhamnoside and an active composition thereof. The new compound and the active composition containing the new compound have activities on inflammation resistance, oxidization resistance and radical removal and can be used for development and application of inflammation-resistant medicaments, health-care products and functional foods.
Description
Technical field
The invention belongs to medical technical field, relate to new compound 5,7, the preparation method of 4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside and active composition thereof and the development and application in anti-inflammatory drug, healthcare products, functional food.
Background technology
Da Ye lindera (Lindera umbellata Thunb.) has another name called tu guan osmanthus, dried sandalwood, the sweet Kashihara of greenery, the sweet wingceltis of leaflet, lindera, is the Lauraceae medicinal plant, is used as medicine with its root.Main product is in China Ningxia, Shaanxi, Gansu, Shanxi, Henan and the middle and lower reach of Yangtze River.Among the peoplely cure mainly vomiting and diarrhoea, cold stomachache, stomachache, wound, rheumatic arthralgia, eczema, mange etc. with it.About its modern chemistry composition and the pharmacology activity research person's report that mostly is the Japanology, systematic research is not goed deep into to this traditional medicinal material as yet by China, finds in our early-stage Study, and this plant milk extract has anti-inflammatory and anti-oxidant activity preferably.Instruct separation to prepare new compound 5,7,4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside and active composition thereof with activity.This achievement in research also is in space state in China, and those skilled in the art are also in the research of being devoted in this respect, for the material effect basis of traditional herbal medicine provides scientific basis.
Summary of the invention
The purpose of this invention is to provide new compound 5,7,4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside, preparation method and the development and application in anti-inflammatory drug, healthcare products, functional food thereof.
Another object of the present invention provides and comprises 5,7, active composition of 4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside and preparation method thereof, and said composition has anti-inflammatory, anti-oxidant and removing free radical activity.
Of the present invention 5,7,4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside has following structure:
It prepares by the following method:
(1) pulverize after the Da Ye lindera medicinal material thorough drying,, adopt the ethanol of 50%-100% or methyl alcohol to soak the back refluxing extraction, extract 2-3 time through solvent-extraction process, united extraction liquid, reclaim under reduced pressure extracting solution to determining alcohol is lower than 5%, contained crude drug concentration 20-40g/mL;
(2) the gained extracting solution is through normal hexane, sherwood oil or hexanaphthene degreasing in the step (1), and the extracting solution after the degreasing volatilizes remaining organic solvent;
(3) extracting solution is through the processing of non-polar macroporous resin column chromatography after the gained degreasing in the step (2), and water and methyl alcohol or ethanol gradient elution obtain 60%-90% alcohol wash-out position, decompression and solvent recovery successively;
(4) step (3) gained alcohol washing is suspended in the aqueous solution, through 1: 2～2: 1 ethyl acetate extraction of volume ratio, reclaims solvent and gets acetic acid ethyl ester extract;
(5) the gained acetic acid ethyl ester extract separates through silica gel column chromatography in the above-mentioned steps (4), with chloroform, methyl alcohol or chloroform, methyl alcohol, water mixed solvent gradient elution;
(6) the gained flow point is handled through the ODS column chromatography in the above-mentioned steps (5), is that the moving phase wash-out obtains the wash-out flow point with methanol or acetonitrile/water;
(7) the gained flow point is through half preparation or preparation HPLC chromatographic separation in the above-mentioned steps (6), and with methanol, acetonitrile/water or methyl alcohol/acetonitrile/water are the moving phase wash-out, obtain the target new compound.
As above among the preparation method, used degreasing solvent is hexanaphthene, normal hexane or sherwood oil (30-60 ℃ or 60-90 ℃) in the step (2), and the volume ratio of degreasing solvent and extracting solution is 1: 2～2: 1.
Step (3) is that extracting solution is handled through the non-polar macroporous resin column chromatography after (2) gained degreasing, and the resin model comprises HPD100, HPD400, and HPD600, D101, versatility non-polar resins such as AB-8, eluent are methyl alcohol or the ethanol of 60%-90%.
Step (4), reclaims solvent and gets acetic acid ethyl ester extract, extraction solvent and aqueous solution volume ratio 1: 2～2: 1 through ethyl acetate extraction for (3) gained alcohol eluate is suspended in (the former plant of 500～1000ml/1kg) behind the aqueous solution.
Step (5) is separated through silica gel column chromatography for (4) gained acetic acid ethyl ester extract, and eluting solvent is the chloroform/methanol (20: 1～2: 1) of different ratios, chloroform/methanol/water (20: 1: 1～7: 3: 1).The chloroform/methanol blending ratio is that 9: 1～7: 1 flow point contains target compound, and chloroform/methanol/water blending ratio is that 12: 3: 1～10: 3: 1 flow point contains target compound.
Step (6) is that (5) gained flow point is handled through the ODS column chromatography, and eluting solvent is methanol or acetonitrile/water.Methanol mixed solvent ratio is that 1: 9～7: 3, acetonitrile/water mixed solvent ratio are 1: 15～4: 3.Methanol mixed solvent ratio is that 4: 6～6: 4, acetonitrile/water mixed solvent ratio are to contain target compound in 2: 8～4: 6 the wash-out flow point.
Step (7) is further separated through half preparation or preparation HPLC for (6) gained flow point, moving phase is methanol or acetonitrile/water, is that 4: 6～6: 4, acetonitrile/water mixed solvent ratio are to separate the flow point in 2: 8～4: 6 to obtain the target new compound from methanol mixed solvent ratio.
The gained acetic acid ethyl ester extract is handled through decolorizing resin in the above-mentioned steps (4), is the eluent wash-out with methyl alcohol or ethanol, and the gained eluate is for comprising 5,7, the active composition of 4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside.Be step (4) gained acetic acid ethyl ester extract through decolorizing resin (LSA-700B, universal models such as LXD-762, D900) handle its active composition.
Resulting active composition, its chemical constitution is as follows:
New compound 5 provided by the invention, 7,4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside and the active composition that comprises this composition have anti-inflammatory, anti-oxidant and remove the activity of free radical, can be used for the development and application in anti-inflammatory drug, healthcare products, the functional food.
Embodiment
The following examples will give further instruction to the present invention, but not thereby limiting the invention.
Embodiment 1
(1) pulverize after the Da Ye lindera medicinal material 5kg thorough drying, through solvent-extraction process, refluxing extraction after the alcohol immersion of employing 75% is spent the night, extract 2 times, extracted united extraction liquid at every turn 3 hours, reclaim under reduced pressure extracting solution to determining alcohol is lower than 3%, contained crude drug concentration 30g/mL;
(2) the middle gained extracting solution of step (1) is through 5L hexanaphthene backflow degreasing, the organic solvent of the extracting solution evaporate to dryness remnants after the degreasing;
(3) extracting solution is through the processing of D101 non-polar macroporous resin column chromatography after the gained degreasing in the step (2), and water and 90% ethanol elution obtain 90% pure wash-out position, decompression and solvent recovery successively;
(4) step (3) gained alcohol washing is suspended in the aqueous solution, and through 1: 1 ethyl acetate extraction of volume ratio three times, combining extraction liquid reclaims solvent and gets acetic acid ethyl ester extract 99g;
(5) the middle gained acetic acid ethyl ester extract of above-mentioned steps (4) after decolorizing resin LSA-700B handles, is an eluent with methyl alcohol with dissolve with methanol, gets active composition 64g.
Embodiment 2
(1) pulverize after the Da Ye lindera medicinal material 5kg thorough drying, through solvent-extraction process, refluxing extraction after the alcohol immersion of employing 90% is spent the night, extract 2 times, extracted united extraction liquid at every turn 2 hours, reclaim under reduced pressure extracting solution to determining alcohol is lower than 3%, contained crude drug concentration 20g/mL;
(2) the middle gained extracting solution of step (1) is through 2L sherwood oil (30～60 ℃) backflow degreasing, the organic solvent of the extracting solution evaporate to dryness remnants after the degreasing;
(3) extracting solution is through the processing of HPD100 non-polar macroporous resin column chromatography after the gained degreasing in the step (2), and water and 70% ethanol elution obtain 70% pure wash-out position, decompression and solvent recovery successively;
(4) step (3) gained alcohol washing is suspended in the aqueous solution, and through 1: 1 ethyl acetate extraction of volume ratio three times, combining extraction liquid reclaims solvent and gets acetic acid ethyl ester extract 46g;
(5) the gained acetic acid ethyl ester extract separates through silica gel column chromatography in the above-mentioned steps (4), with chloroform, methyl alcohol 20: 1, and 15: 1,12: 1,9: 1,7: 1,5: 1,3: 1 gradient elutions;
(6) 9: 1～7: 1 flow points of gained are handled through the ODS column chromatography in the above-mentioned steps (5), and with methanol: 1: 9,2: 8,3: 7,5: 5,6: 4, be moving phase wash-out at 7: 3, and decompression and solvent recovery obtains each wash-out flow point;
(7) the gained flow point is through half preparation or preparation HPLC chromatographic separation in the above-mentioned steps (6), and with 50% methanol moving phase wash-out, retention time 27min obtains the target new compound;
This compound is yellow powder (methyl alcohol).Provide quasi-molecular ion peak m/z485[M+Na in the FABMS spectrum]
+, provide m/z 485.1044[M+Na in the HRFABMS spectrum]
+(calcd.485.1060), determine that thus molecular weight is 462, molecular formula is C
22H
22O
11The NMR data (table 1) of binding compounds identify that its structure is:
The NMR data of table 1 compound
The antioxidation activity in vitro of gained new compound test among gained active composition and the embodiment 2 among embodiment 3 embodiment 1
Experimental technique:
(1) DPPH method is measured absorbancy in the 515nm place.Every duplicate samples parallel running 3 times, calculation formula is: clearance rate (%)=[(A
Control-A
Sample)/A
Control] * 100%, A in the formula
ControlBe the absorbancy after 3.5mLDPPH solution and the 0.1mL methanol mixed, A
SampleBe the absorbancy after 3.5mL DPPH solution and the 0.1mL sample mix.
(2) ABTS method is measured absorbancy in the 734nm place.Every duplicate samples parallel running 3 times, calculation formula is: clearance rate (%)=[(A
Control-A
Sample)/A
Control] * 100%.AControl is 2.85mL ABTS in the formula
+Absorbancy after solution and the 0.15mL methanol mixed, ASamp le is 2.85mL ABTS
+Absorbancy after solution and the 0.15mL sample mix.
(3) statistical procedures method
Experiment records data, according to the clearance rate that above-mentioned formula calculates, uses the SPSS13.0 software processes, obtains the IC that sample is removed DPPH free radical and ABTS free radical
50Value.
Experimental result: see Table 2
The antioxidation activity in vitro experimental result of table 2 embodiment 1 gained living-article composition and embodiment 2 gained new compounds
BHA, the positive contrast of BHT
The anti-inflammatory activity of gained new compound test among gained active composition and the embodiment 2 among embodiment 4 embodiment 1
Adopt dimethylbenzene inductive mice ear model, the anti-inflammatory activity of test compounds 1.
Laboratory animal: the male mouse of kunming of body weight 28 ± 3g
Test method: mouse is divided into 3 groups at random by body weight, every group 10, after each organized the mouse etherization, the two sides was coated with each the 40 μ l of xylene solution that contain each compound 1 or positive drug (acetylsalicylic acid) 1mg/ml before and after the Yu Zuoer, and model control group directly is coated with 40 μ l dimethylbenzene.2.5 after hour the mouse dislocation is put to death, lay the ear sheet with diameter 7mm punch tool in left and right sides ear same position, to weigh, the weight difference of left and right sides ear sheet is as the swelling degree, and comparative group differences significance.
Experimental result: see Table 3
The influence of table 3 compound 1 p-Xylol inducing mouse ear swelling degree
Compare with model control group
*: P＜0101, significantly different from control group
Claims (11)
1. have 5,7 of following structure, 4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside:
One kind as claimed in claim 15,7, the preparation method of 4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside is characterized in that, comprises the steps:
(1) pulverize after the Da Ye lindera medicinal material thorough drying,, adopt the ethanol of 50%-100% or methyl alcohol to soak the back refluxing extraction, extract 2-3 time through solvent-extraction process, united extraction liquid, reclaim under reduced pressure extracting solution to determining alcohol is lower than 5%, contained crude drug concentration 20-40g/mL;
(2) the gained extracting solution is through normal hexane, sherwood oil or hexanaphthene degreasing in the step (1), and the extracting solution after the degreasing volatilizes remaining organic solvent;
(3) extracting solution is through the processing of non-polar macroporous resin column chromatography after the gained degreasing in the step (2), and water and methyl alcohol or ethanol gradient elution obtain 60%-90% alcohol wash-out position, decompression and solvent recovery successively;
(4) step (3) gained alcohol washing is suspended in the aqueous solution, through 1: 2～2: 1 ethyl acetate extraction of volume ratio, reclaims solvent and gets acetic acid ethyl ester extract;
(5) the gained acetic acid ethyl ester extract separates through silica gel column chromatography in the above-mentioned steps (4), with chloroform, methyl alcohol or chloroform, methyl alcohol, water mixed solvent gradient elution;
(6) the gained flow point is handled through the ODS column chromatography in the above-mentioned steps (5), is that the moving phase wash-out obtains the wash-out flow point with methanol or acetonitrile/water;
(7) the gained flow point is through half preparation or preparation HPLC chromatographic separation in the above-mentioned steps (6), and with methanol, acetonitrile/water or methyl alcohol/acetonitrile/water are to obtain behind the moving phase wash-out.
3. preparation method according to claim 2 is characterized in that, used degreasing solvent is hexanaphthene, normal hexane or sherwood oil (30-60 ℃ or 60-90 ℃) in the described step (2), and the volume ratio of degreasing solvent and extracting solution is 1: 2～2: 1.
4. preparation method according to claim 2 is characterized in that, described step (3) is that extracting solution is handled through the non-polar macroporous resin column chromatography after (2) gained degreasing, and eluent is methyl alcohol or the ethanol of 60%-90%.
5. preparation method according to claim 2, it is characterized in that, described step (4) is after (3) gained alcohol eluate is suspended in the aqueous solution, its concentration is the former plant of 500～1000ml/1kg, through ethyl acetate extraction, reclaim solvent and get acetic acid ethyl ester extract, extraction solvent and aqueous solution volume ratio 1: 2～2: 1.
6. preparation method according to claim 2, it is characterized in that, described step (5) is separated through silica gel column chromatography for (4) gained acetic acid ethyl ester extract, and eluting solvent is 20: 1～2: 1 chloroform/methanol or chloroform/methanol/water of 20: 1: 1～7: 3: 1; In the chloroform/methanol blending ratio is that 9: 1～7: 1, chloroform/methanol/water blending ratio are that 12: 3: 1～10: 3: 1 flow point contains target compound.
7. preparation method according to claim 2, it is characterized in that, to be (5) gained flow point handle through the ODS column chromatography described step (6), and eluting solvent is methanol or acetonitrile/water, and methanol mixed solvent ratio is that 1: 9～7: 3, acetonitrile/water mixed solvent ratio are 1: 15～4: 3; In methanol mixed solvent ratio is that 4: 6～6: 4, acetonitrile/water mixed solvent ratio are to contain target compound in 2: 8～4: 6 the wash-out flow point.
8. preparation method according to claim 2, it is characterized in that, described step (7) is that (6) gained flow point is through half preparation or preparation HPLC chromatographic separation, moving phase is methanol or acetonitrile/water, is that 4: 6～6: 4, acetonitrile/water mixed solvent ratio are to separate the flow point in 2: 8～4: 6 to obtain the target new compound from methanol mixed solvent ratio.
9. preparation method according to claim 2 is characterized in that, the gained acetic acid ethyl ester extract is handled through decolorizing resin in the step (4), with methyl alcohol or ethanol is the eluent wash-out, the gained eluate is for containing 5,7, the active composition of 4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside.
10. preparation method according to claim 9 is characterized in that, described active composition is made up of following component:
11.5,7,4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside and active composition thereof are at preparation anti-inflammatory, anti-oxidant and remove application in the medicine of free radical.
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Cited By (2)
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| CN103613623A (en) * | 2013-11-28 | 2014-03-05 | 江苏科技大学 | Application of multistage solvent extraction method in enzymatic synthesis of isoquercitrin |
| CN113413391A (en) * | 2021-06-19 | 2021-09-21 | 山西医科大学 | Pharmaceutical application of rhamnosine-3-O-alpha-rhamnoside and anti-inflammatory drug |
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Cited By (3)
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|---|---|---|---|---|
| CN103613623A (en) * | 2013-11-28 | 2014-03-05 | 江苏科技大学 | Application of multistage solvent extraction method in enzymatic synthesis of isoquercitrin |
| CN103613623B (en) * | 2013-11-28 | 2016-05-11 | 江苏科技大学 | The application of multiple-stage solvent extraction in the synthetic isoquercitrin of enzymatic |
| CN113413391A (en) * | 2021-06-19 | 2021-09-21 | 山西医科大学 | Pharmaceutical application of rhamnosine-3-O-alpha-rhamnoside and anti-inflammatory drug |
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