CN101935332B - 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
Great Ye lindera (Lindera umbellata Thunb.) has another name called tu guan osmanthus, dry sandalwood, the sweet Kashihara of greenery, the sweet wingceltis of leaflet, lindera, is 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 with it, cold stomachache, stomachache, wound, rheumatic arthralgia, eczema, mange etc.About its modern chemistry composition and the pharmacology activity research person's report that mostly is Japanology, systematic research is not yet goed deep into this traditional medicine by China, in our early-stage Study, finds, this plant milk extract has good anti-inflammatory and anti-oxidant activity.Instruct to separate with activity and prepared new compound 5,7,4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside and active composition thereof.This achievement in research is in China also in space state, and those skilled in the art are also in the research of being devoted in this respect, for the material effect basis of Chinese traditional herbs provides scientific basis.
Summary of the invention
The object 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 is to provide 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) the abundant crushed after being dried of great Ye lindera medicinal material, through solvent-extraction process, adopts the ethanol of 50%-100% or methyl alcohol to soak rear refluxing extraction, extract 2-3 time, united extraction liquid, reclaim under reduced pressure extracting solution to determining alcohol lower than 5%, contained crude drug concentration 20-40g/mL;
(2) in step (1), gained extracting solution is through normal hexane, sherwood oil or hexanaphthene degreasing, and the extracting solution after degreasing volatilizes remaining organic solvent;
(3) in step (2), after gained degreasing, extracting solution is through the processing of non-polar macroporous resin column chromatography, and water and methyl alcohol or ethanol gradient elution successively, obtains 60%-90% alcohol wash-out position, decompression and solvent recovery;
(4) step (3) gained alcohol washing is suspended in the aqueous solution, through the extraction of the volume ratio ethyl acetate of 1: 2～2: 1, reclaims solvent and obtains acetic acid ethyl ester extract;
(5) in above-mentioned steps (4), gained acetic acid ethyl ester extract separates through silica gel column chromatography, with chloroform, methyl alcohol or chloroform, methyl alcohol, water mixed solvent gradient elution;
(6) gained flow point, through the processing of ODS column chromatography, obtains wash-out flow point taking methanol/water or acetonitrile/water as moving phase wash-out in above-mentioned steps (5);
(7) in above-mentioned steps (6), gained flow point is through half preparation or preparation HPLC chromatographic separation, and with methanol/water, acetonitrile/water or methyl alcohol/acetonitrile/water are moving phase wash-out, obtain target new compound.
As above in preparation method, in step (2), degreasing solvent used is hexanaphthene, normal hexane or sherwood oil (30-60 DEG C or 60-90 DEG C), and the volume ratio of degreasing solvent and extracting solution is 1: 2～2: 1.
Step (3) is that after (2) gained degreasing, extracting solution is through the processing of non-polar macroporous resin column chromatography, and resin model comprises HPD100, HPD400, HPD600, D101, the versatility non-polar resins such as AB-8, the methyl alcohol that eluent is 60%-90% or ethanol.
Step (4) is suspended in (the former plant of 500～1000ml/1kg) after the aqueous solution for (3) gained alcohol eluate, extract through ethyl acetate, reclaim solvent and obtain acetic acid ethyl ester extract, extraction solvent and aqueous solution volume ratio 1: 2～2: 1.
Step (5) separates through silica gel column chromatography for (4) gained acetic acid ethyl ester extract, eluting solvent is the chloroform/methanol (20: 1～2: 1) of different ratios, chloroform/methanol/water (20: 1: 1～7: 3: 1).Chloroform/methanol blending ratio is that the flow point of 9: 1～7: 1 contains target compound, and chloroform/methanol/water blending ratio is that the flow point of 12: 3: 1～10: 3: 1 contains target compound.
Step (6) be (5) gained flow point through the processing of ODS column chromatography, eluting solvent is methanol/water or acetonitrile/water.Methanol/water mixed solvent ratio is that 1: 9～7: 3, acetonitrile/water mixed solvent ratio are 1: 15～4: 3.Methanol/water mixed solvent ratio is that 4: 6～6: 4, acetonitrile/water mixed solvent ratio are to contain target compound in the wash-out flow point of 2: 8～4: 6.
Step (7) is for (6) gained flow point is through partly preparation or preparation HPLC further separate, moving phase is methanol/water or acetonitrile/water, is that 4: 6～6: 4, acetonitrile/water mixed solvent ratio are to separate and obtain target new compound 2: 8～4: 6 flow points from methanol/water mixed solvent ratio.
Gained acetic acid ethyl ester extract is through decolorizing resin processing in above-mentioned steps (4), and taking methyl alcohol or ethanol as eluent wash-out, gained eluate is for comprising 5,7, the active composition of 4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside.Be that step (4) gained acetic acid ethyl ester extract is processed to obtain its active composition through decolorizing resin (LSA-700B, the universal models such as LXD-762, D900).
The active composition obtaining, 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, functional food.
Embodiment
The following examples will be further described the present invention, but not thereby limiting the invention.
Embodiment 1
(1) the abundant crushed after being dried of great Ye lindera medicinal material 5kg, through solvent-extraction process, adopt 75% alcohol immersion to spend the night after refluxing extraction, extract 2 times, extract united extraction liquid at every turn 3 hours, reclaim under reduced pressure extracting solution to determining alcohol 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 degreasing;
(3) in step (2), after gained degreasing, extracting solution is through the processing of D101 non-polar macroporous resin column chromatography, and water and 90% ethanol elution successively, obtains 90% alcohol wash-out position, decompression and solvent recovery;
(4) step (3) gained alcohol washing is suspended in the aqueous solution, and through the volume ratio ethyl acetate of 1: 1 extraction three times, combining extraction liquid reclaims solvent and obtains acetic acid ethyl ester extract 99g;
(5) gained acetic acid ethyl ester extract is processed through decolorizing resin LSA-700B after with dissolve with methanol in above-mentioned steps (4), taking methyl alcohol as eluent, obtains active composition 64g.
Embodiment 2
(1) the abundant crushed after being dried of great Ye lindera medicinal material 5kg, through solvent-extraction process, adopt 90% alcohol immersion to spend the night after refluxing extraction, extract 2 times, extract united extraction liquid at every turn 2 hours, reclaim under reduced pressure extracting solution to determining alcohol 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 DEG C) backflow degreasing, the organic solvent of the extracting solution evaporate to dryness remnants after degreasing;
(3) in step (2), after gained degreasing, extracting solution is through the processing of HPD100 non-polar macroporous resin column chromatography, and water and 70% ethanol elution successively, obtains 70% alcohol wash-out position, decompression and solvent recovery;
(4) step (3) gained alcohol washing is suspended in the aqueous solution, and through the volume ratio ethyl acetate of 1: 1 extraction three times, combining extraction liquid reclaims solvent and obtains acetic acid ethyl ester extract 46g;
(5) gained acetic acid ethyl ester extract separates through silica gel column chromatography in 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) in above-mentioned steps (5) 9: 1～7: 1 flow points of gained through the processing of ODS column chromatography, with methanol/water: 1: 9,2: 8,3: 7,5: 5,7: 3 be moving phase wash-out at 6: 4, and decompression and solvent recovery obtains each wash-out flow point;
(7) in above-mentioned steps (6), gained flow point is through half preparation or preparation HPLC chromatographic separation, and with 50% methanol/water moving phase wash-out, retention time 27min obtains target new compound;
This compound is yellow powder (methyl alcohol).In FABMS spectrum, provide quasi-molecular ion peak m/z485[M+Na]
+, in HRFABMS spectrum, provide m/z 485.1044[M+Na]
+(calcd.485.1060), determine that thus molecular weight is 462, molecular formula is C
22h
22o
11.The 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 in gained active composition and embodiment 2 in embodiment 3 embodiment 1
Experimental technique:
(1) DPPH method, measures absorbancy in 515nm place.Every duplicate samples parallel running 3 times, calculation formula is: clearance rate (%)=[(A
control-A
sample)/A
control] × 100%, A in formula
controlfor the absorbancy after 3.5mLDPPH solution and 0.1mL methanol mixed, A
samplefor the absorbancy after 3.5mL DPPH solution and 0.1mL sample mix.
(2) ABTS method, measures absorbancy in 734nm place.Every duplicate samples parallel running 3 times, calculation formula is: clearance rate (%)=[(A
control-A
sample)/A
control] × 100%.In formula, AControl is 2.85mL ABTS
+absorbancy after solution and 0.15mL methanol mixed, ASamp le is 2.85mL ABTS
+absorbancy after solution and 0.15mL sample mix.
(3) statistical procedures method
Experiment data measured, the clearance rate calculating according to above-mentioned formula, uses SPSS13.0 software processes, obtains the IC of sample removing DPPH free radical and ABTS free radical
50value.
Experimental result: in 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 in gained active composition and embodiment 2 in embodiment 4 embodiment 1
Adopt the mice ear model of dimethylbenzene induction, 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 group mouse etherization, before and after Yu Zuoer, two sides is coated with the each 40 μ l of xylene solution that contain each compound 1 or positive drug (acetylsalicylic acid) 1mg/ml, and model control group is directly coated with 40 μ l dimethylbenzene.After 2.5 hours, mouse dislocation is put to death, lay ear sheet with diameter 7mm punch tool in left and right ear same position, weigh, the weight difference of left and right ear sheet is as swelling, and the significance of difference between comparative group.
Experimental result: in table 3
The impact of table 3 compound 1 p-Xylol inducing mouse ear swelling degree
With model control group comparison
*: P < 0101, significantly different from control group
Claims (11)
1. there is 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) the abundant crushed after being dried of great Ye lindera medicinal material, through solvent-extraction process, adopt the ethanol of 50%-100% or methyl alcohol to soak after refluxing extraction, extract 2-3 time, united extraction liquid, reclaim under reduced pressure extracting solution to determining alcohol lower than 5%, contained crude drug concentration 20-40g/mL;
(2) in step (1), gained extracting solution is through normal hexane, sherwood oil or hexanaphthene degreasing, and the extracting solution after degreasing volatilizes remaining organic solvent;
(3) in step (2), after gained degreasing, extracting solution is through the processing of non-polar macroporous resin column chromatography, and water and methyl alcohol or ethanol gradient elution successively, obtains 60%-90% alcohol wash-out position, decompression and solvent recovery;
(4) step (3) gained alcohol washing is suspended in the aqueous solution, through the ethyl acetate extraction of volume ratio 1:2～2:1, reclaims solvent and obtains acetic acid ethyl ester extract;
(5) in above-mentioned steps (4), gained acetic acid ethyl ester extract separates through silica gel column chromatography, with chloroform, methyl alcohol or chloroform, methyl alcohol, water mixed solvent gradient elution, the chloroform/methanol that eluting solvent is 20:1～2:1 or chloroform/methanol/water of 20:1:1～7:3:1;
(6) gained flow point, through the processing of ODS column chromatography, obtains wash-out flow point taking methanol/water or acetonitrile/water as moving phase wash-out in above-mentioned steps (5), and methanol/water mixed solvent ratio is that 1:9～7:3, acetonitrile/water mixed solvent ratio are 1:15～4:3;
(7) in above-mentioned steps (6), gained flow point is through half preparation or preparation HPLC chromatographic separation, and with methanol/water, acetonitrile/water or methyl alcohol/acetonitrile/water are to obtain after moving phase wash-out.
3. preparation method according to claim 2, it is characterized in that, in described step (2), degreasing solvent used is hexanaphthene, normal hexane or sherwood oil, and the boiling range of described sherwood oil is 30-60 DEG C or 60-90 DEG C, 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) be after (2) gained degreasing extracting solution through the processing of non-polar macroporous resin column chromatography, the methyl alcohol that eluent is 60%-90% or ethanol.
5. preparation method according to claim 2, it is characterized in that, described step (4) is suspended in after the aqueous solution for (3) gained alcohol eluate, its concentration is the former plant of 500～1000ml/1kg, extract through ethyl acetate, reclaim solvent and obtain acetic acid ethyl ester extract, extraction solvent and aqueous solution volume ratio 1:2～2:1.
6. preparation method according to claim 2, is characterized in that, described step (5) is that the flow point that 9:1～7:1, chloroform/methanol/water blending ratio are 12:3:1～10:3:1 contains target compound in chloroform/methanol blending ratio.
7. preparation method according to claim 2, is characterized in that, described step (6) is to contain target compound in 4:6～6:4, the acetonitrile/water mixed solvent ratio wash-out flow point that is 2:8～4:6 in methanol/water mixed solvent ratio.
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/water or acetonitrile/water, is that 4:6～6:4, acetonitrile/water mixed solvent ratio are to separate and obtain target new compound 2:8～4:6 flow point from methanol/water mixed solvent ratio.
9. preparation method according to claim 2, it is characterized in that, in step (4), gained acetic acid ethyl ester extract is through decolorizing resin processing, taking methyl alcohol or ethanol as eluent wash-out, 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. is claimed in claim 15,7, and 4 '-trihydroxy-8-methoxyl group-3-O-alpha-L-rhamnoside or active composition claimed in claim 10 are preparing anti-inflammatory, anti-oxidant and remove the application in the medicine of free radical.
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| 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 |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1724552A (en) * | 2005-07-08 | 2006-01-25 | 南京大学 | Preparation method of astilbin |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1724552A (en) * | 2005-07-08 | 2006-01-25 | 南京大学 | Preparation method of astilbin |
Non-Patent Citations (11)
| Title |
|---|
| Astilbin inhibits the adhesion of T lymphocytes via decreasing TNF-α and its associated MMP-9 activity and CD44 expression;Hong-wei Yi,等;《International Immunopharmacology》;20081031;第8卷(第10期);第1467-1474页 * |
| Hong-wei Yi,等.Astilbin inhibits the adhesion of T lymphocytes via decreasing TNF-α and its associated MMP-9 activity and CD44 expression.《International Immunopharmacology》.2008,第8卷(第10期),第1467-1474页. |
| Hossein BABAEI，等.Antioxidant and Vasorelaxant Activities of Flavonoids from Amygdalus lycioides var. horrida.《Turk J Biol》.2008,第32卷(第3期),第203-208页. * |
| JP特开平8-188791A 1996.07.23 |
| Mingjian Fei，等.Astilbin inhibits contact hypersensitivity through negative cytokine regulation distinct from cyclosporin A.《J ALLERGY CLIN IMMUNOL》.2005,第116卷(第6期),第1350-1356页. * |
| Paola Montoro,等.Structure–antioxidant activity relationships of flavonoids isolated from different plant species.《Food Chemistry》.2005,第92卷(第2期),第349–355页. * |
| Qing-Feng Zhang，等.Antioxidant activity of Rhizoma Smilacis Glabrae extracts and its key constituent-astilbin.《Food Chemistry》.2009,第115卷(第1期),第297-303页. * |
| Xiao Wei Wang,等.A New Phloroglucinol Diglycoside Derivative from Hypericum japonicum Thunb..《Molecules》.2008,第13卷(第11期),第2796-2803页. * |
| 李敬芬.黄酮类化合物的作用.《黄酮类衍生物的合成和性质》.2008,(第1版),第4页. * |
| 王晓丹.花旗松素和落新妇苷体外转运和大鼠体内药物代谢动力学研究.《浙江大学博士学位论文》.2009,第2-4,106,115页. |
| 花旗松素和落新妇苷体外转运和大鼠体内药物代谢动力学研究;王晓丹;《浙江大学博士学位论文》;20091015;第2-4,106,115页 * |
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