CN103864656B - The method of astaxanthin one ester of astaxanthin odd-numbered fatty acid one ester is rich in preparation - Google Patents
The method of astaxanthin one ester of astaxanthin odd-numbered fatty acid one ester is rich in preparation Download PDFInfo
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- CN103864656B CN103864656B CN201410074779.1A CN201410074779A CN103864656B CN 103864656 B CN103864656 B CN 103864656B CN 201410074779 A CN201410074779 A CN 201410074779A CN 103864656 B CN103864656 B CN 103864656B
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Abstract
The invention discloses a kind of method of preparing astaxanthin one ester that is rich in astaxanthin odd-numbered fatty acid one ester, step is: get astaxanthin one ester, be dissolved in carrene, use capillary microcap at AgNO3On efficient lamellae, put into line, be then placed in the glass chromatography cylinder that is added with solvent and launch; After launching, take out and dry, 2 bands are scraped, ultrasonic, centrifugal, get supernatant, repeat to be extracted into the band scraping colourless, obtain respectively the each self-corresponding extract of 2 band, rotary evaporation is removed carrene, obtains 2 kinds of samples, and Article 1 red zone is astaxanthin one ester containing 7～9% astaxanthin tridecylenic acid one esters and 48～51% astaxanthin pentadecanoic acid one esters. The present invention utilizes AgNO3Efficient lamellae partition method has obtained being rich in astaxanthin one ester of odd-numbered fatty acid, the separation of astaxanthin monoesters has been advanced to major step, for the separation of astaxanthin odd-numbered fatty acid provides foundation, also for following separation and purification is again laid a good foundation.
Description
Technical field
The present invention relates to one prepares and is rich in astaxanthin odd-numbered fatty acid one ester (astaxanthin tridecylenic acid one ester and astaxanthin pentadecanoic acidOne ester) the method for astaxanthin one ester.
Background technology
Krill is the key species of Southern Oceans biological chain, be in the world biomass energy maximum, evolve the most single plant rawGoods and materials source, approximately 6～5,000,000,000 tons (because method of estimation difference has larger difference, minimum conservative estimation also has 6～1,000,000,000 tons), Nian KeQuantity of the catch reaches 1～1.5 hundred million ton, catches total amount (0.99 hundred million ton) more than whole world year fishery, and there are 1,800,000,000 mu of arable lands, grain in ChinaNearly 600,000,000 tons of eclipse year output, the year of krill can be equivalent to 3～4.5 hundred million mu of arable lands by quantity of the catch, is huge resource overseas.
Krill is containing abundant lubricant component, especially containing abundant astaxanthin, astaxanthin one ester and astaxanthin diester. AstaxanthinOne ester is that one end of astaxanthin connects a fatty acid molecule. This fatty acid molecule may be odd number may be also even number, because ofThis astaxanthin one ester is a molecular group, and each molecule wherein all plays an important role in the growing of krill.To be rich in astaxanthin tridecylenic acid one ester and astaxanthin pentadecanoic acid one ester is separated, and be conducive to advance astaxanthin odd-numbered fatty acidThe separating again of one ester, be further purified and the research of physiologically active difference, be also of value to the shrimp of the different odd of following manufactureEffective utilization of blue or green plain aliphatic acid one ester. There is no at present one and effectively from astaxanthin one ester, isolate odd-numbered fatty acid one ester (shrimpBlue or green plain tridecylenic acid one ester and astaxanthin pentadecanoic acid one ester) method.
Summary of the invention
For above-mentioned prior art, the invention provides one separation preparation from astaxanthin one ester and be rich in astaxanthin odd-numbered fatty acidThe method of astaxanthin one ester of one ester (astaxanthin tridecylenic acid one ester and astaxanthin pentadecanoic acid one ester).
The present invention is achieved by the following technical solutions:
One is prepared the shrimp of being rich in astaxanthin odd-numbered fatty acid one ester (astaxanthin tridecylenic acid one ester and astaxanthin pentadecanoic acid one ester)The method of a blue or green plain ester, step is:
(1) prepare krill shrimp sauce: get krill, aeration-drying, to constant weight, is crushed to 20 orders at 35 DEG C～65 DEG C,At 30 DEG C, extract 3 times with No. six gasoline, each 1h, oil plant liquor ratio is 1:6(mass ratio), obtain and slightly extract oil, then use thirdKetone extracts thick extraction oily 3 times at 30 DEG C, each 0.5h, solid-liquid ratio is 1:5(mass ratio), to remove insoluble residue,Obtain krill shrimp sauce;
(2) extraction of astaxanthin one ester: by 68g200～300 object GF254Silica gel is placed in 120 DEG C of activation 12h of drying box,Then fill post with petroleum ether dissolution, for subsequent use; Be followed successively by by volume benzinum: ethyl acetate=10:1,9:1,8:1,7:1,6:1,5:1,4:1,3:1,2:1, the each 500mL of ratio preparation eluent of 1:1, for subsequent use;
The krill shrimp sauce sample introduction of getting the above-mentioned preparation of 2ml, first carries out drip washing with 100ml benzinum, then is followed successively by by volume ratioBenzinum: ethyl acetate=10:1,9:1,8:1,7:1,6:1,5:1,4:1,3:1,2:1,1:1 washesDe-liquid carries out drip washing, and collected volume ratio is benzinum: ethyl acetate=3:1,2:1, and the eluent of 1:1, merges, and rotation is steamedSend out and remove benzinum and ethyl acetate, products obtained therefrom is astaxanthin one ester;
(first two steps are prepared astaxanthin one ester, the method preparation in can also the patent application that be CN102746205A according to publication numberObtain)
(3) separation of odd-numbered fatty acid one ester: get the astaxanthin one ester 20mg of above-mentioned preparation, be dissolved in 1.5ml carreneIn, obtain astaxanthin one ester solution, get 0.5ml, use capillary microcap at AgNO3On efficient lamellae, put into line (under plateAlong 1.5cm place), be then placed in the glass chromatography cylinder [200mm × 200mm(L × H)] that is added with 24ml solvent and launch; ExhibitionOpen rear taking-up and dry, visible astaxanthin one ester is unfolded and is 2 bands, from upper (referring to solvent front) under be followed successively by: 1. firstBar red zone Rf is 0.41; 2. the yellow band of Article 2 Rf is 0.36; 2 bands are scraped, put into the test tube that fills carreneIn, test tube is placed under 40KHz, 200～500W power to ultrasonic 3～10 minutes, then centrifugal under 4000～6000r/min,Get supernatant, repeat above leaching process 3～5 times colourless to the band scraping, obtain respectively the each self-corresponding extract of 2 band,Rotary evaporation is removed carrene, obtains 2 kinds of samples, analyze after testing, and, these 2 kinds of samples are followed successively by that (each percentage is by qualityPercentage meter): Article 1 red zone is to contain 7～9% astaxanthin tridecylenic acid one esters and 48～51% astaxanthin pentadecanoic acid one estersAstaxanthin one ester; The yellow band of Article 2 is astaxanthin one ester containing 100% even number astaxanthin aliphatic acid one ester.
Described AgNO3Efficient lamellae prepares by the following method: by tlc silica gel plate H(10cm × 20cm)The AgNO that is 1～2.5% in mass concentration3In methanol solution, soak 4～16 minutes, take out, dry 0.5～2.5 hour, thenPut into 45～85 DEG C, drying box and dry 0.5～1.5 hour, to obtain final product.
Described solvent is that the benzinum, acetone and the triethylamine that are 9.5ml:3ml:10 μ l by volume ratio mix.
The described method that sample is detected is: from 2 samples, respectively get 5mg, respectively adding 0.5ml percentage by volume is 7The concentrated sulfuric acid methanol solution of %, 60 DEG C of heating water baths 15 minutes, add 1ml n-hexane after cooling, and vibration, leaves standstill and gets after 5 minutesSupernatant (n-hexane layer) is in 2ml small test tube, and 10h is to becoming solid esterification sample in fume hood volatilization; Then will prepareEsterification sample dissolution in n-hexane, on Alilent6890GC-5973MS gas chromatography mass spectrometry chromatograph, detect: chromatographic column#1, Agilent19091N-213:1538.60580HP-INNOWaxPolyethyleneGlyco, 60 DEG C of initial temperatures,Pressure 8.3239psi, flow velocity 1ml/min, average speed 36.966cm/s, 1.3653 minutes holdup times, running time 43Minute.
Aliphatic acid kind, the quantity of contained astaxanthin one ester of different crustaceans have larger difference, and the present invention is with from South Pole phosphorusAstaxanthin one ester prepared by shrimp is raw material, through containing AgNO3Efficient lamellae launch to separate, astaxanthin one ester can be divided into 2Band, two bands extract through scraper plate, concentrate to obtain product. After testing, utilize AgNO3Efficient lamellae partition method, can prepare containing 7～Astaxanthin one ester of 9% astaxanthin tridecylenic acid one ester and 48～51% astaxanthin pentadecanoic acid one esters. The present invention utilizes AgNO3EfficientlyLamellae partition method has obtained being rich in astaxanthin one ester of odd-numbered fatty acid, the separation of astaxanthin monoesters has been advanced to major step,For the separation of astaxanthin odd-numbered fatty acid provides foundation, also for following separation and purification is again laid a good foundation.
Detailed description of the invention
Below in conjunction with embodiment, the present invention is further illustrated.
Embodiment 1 separates astaxanthin odd-numbered fatty acid one ester (astaxanthin tridecylenic acid one ester and shrimp green grass or young crops from astaxanthin one esterElement pentadecanoic acid one ester)
Step is as follows:
(1) prepare krill shrimp sauce: get krill, aeration-drying, to constant weight, is crushed to 20 orders at 35 DEG C～65 DEG C,At 30 DEG C, extract 3 times with No. six gasoline, each 1h, oil plant liquor ratio is 1:6(mass ratio), obtain and slightly extract oil, then use thirdKetone extracts thick extraction oily 3 times at 30 DEG C, each 0.5h, solid-liquid ratio is 1:5(mass ratio), to remove insoluble residue,Obtain krill shrimp sauce;
(2) extraction of astaxanthin one ester: by 68g200～300 object GF254Silica gel is placed in 120 DEG C of activation 12h of drying box,Then fill post with petroleum ether dissolution, for subsequent use; Be followed successively by by volume benzinum: ethyl acetate=10:1,9:1,8:1,7:1,6:1,5:1,4:1,3:1,2:1, the each 500mL of ratio preparation eluent of 1:1, for subsequent use;
The krill shrimp sauce sample introduction of getting the above-mentioned preparation of 2ml, first carries out drip washing with 100ml benzinum, then is followed successively by by volume ratioBenzinum: ethyl acetate=10:1,9:1,8:1,7:1,6:1,5:1,4:1,3:1,2:1,1:1 washesDe-liquid carries out drip washing, and collected volume ratio is benzinum: ethyl acetate=3:1,2:1, and the eluent of 1:1, merges, and rotation is steamedSend out and remove benzinum and ethyl acetate, products obtained therefrom is astaxanthin one ester;
(3) prepare AxNO3Efficient lamellae: get 10cm × 20cm tlc silica gel plate H, being placed on mass concentration is 1%AgNO3Methanol solution in soak 10 minutes, take out and dry 1h, then put into 85 DEG C, drying box and dry 0.5h, to obtain final product, for subsequent use.
(4) from refrigerator, (26 DEG C) take out the krill astaxanthin one ester 20mg having prepared, and are dissolved in 1.5ml dichloromethaneIn alkane, obtain astaxanthin one ester solution, get 0.5ml, use capillary microcap point at AgNO3On efficient lamellae, (distance is lower to 1.5cmPlace), sample liquid is put into line, be placed on and be added with 24ml solvent (benzinum: acetone: triethylamine=9.5ml:3ml:10 μ is l)Glass chromatography cylinder [200mm × 200mm(L × H)] in launch; After launching, take out and dry, visible astaxanthin one ester is at lamellaeOn be 2 bands, from upper (referring to solvent front) under be followed successively by: 1. Article 1 red zone Rf is 0.41; 2. Article 2 yellowBand Rf is 0.36; After 2 bands are scraped respectively, put into separately 2 test tubes of carrene, 2 test tubes are simultaneously at 40KHz,Under power 200W condition, ultrasonic extraction 10 minutes, then centrifugal under 4000r/min, gets supernatant, repeats above extractionJourney 5 times is colourless to the band scraping, and each gets extract 20ml; Extract rotary evaporation is removed to carrene, obtain 2 parts of shrimp green grass or young cropsElement one ester sample.
(5) detect: the 5mg sample of respectively asking for from 2 samples, adding respectively 0.5ml percentage by volume is 7% concentrated sulfuric acid firstAlcoholic solution, 60 DEG C of heating water baths 15 minutes, add 1ml n-hexane after cooling, vibration, leave standstill after 5 minutes, get supernatant (just oneselfAlkane layer) in 2ml small test tube, 10h is to becoming solid esterification sample in fume hood volatilization. By the esterification sample dissolution of preparationIn n-hexane, on Alilent6890GC-5973MS gas chromatography mass spectrometry chromatograph, detect: chromatographic column #1, Agilent19091N-213:1538.60580HP-INNOWaxPolyethyleneGlyco, 60 DEG C of initial temperatures, pressure8.3239psi, flow velocity 1ml/min, average speed 36.966cm/s, 1.3653 minutes holdup times, 43 minutes running times.
Testing result: after testing, Article 1 red zone is containing 7% astaxanthin tridecylenic acid one ester and 51% astaxanthin pentadecanoic acidOne ester. The yellow band of Article 2 contains 100% even number astaxanthin aliphatic acid one ester.
Embodiment 2 separates astaxanthin odd-numbered fatty acid one ester (astaxanthin tridecylenic acid one ester and shrimp green grass or young crops from astaxanthin one esterElement pentadecanoic acid one ester)
Step is as follows:
(1) prepare krill shrimp sauce: get krill, aeration-drying, to constant weight, is crushed to 20 orders at 35 DEG C～65 DEG C,At 30 DEG C, extract 3 times with No. six gasoline, each 1h, oil plant liquor ratio is 1:6(mass ratio), obtain and slightly extract oil, then use thirdKetone extracts thick extraction oily 3 times at 30 DEG C, each 0.5h, solid-liquid ratio is 1:5(mass ratio), to remove insoluble residue,Obtain krill shrimp sauce;
(2) extraction of astaxanthin one ester: by 68g200～300 object GF254Silica gel is placed in 120 DEG C of activation 12h of drying box,Then fill post with petroleum ether dissolution, for subsequent use; Be followed successively by by volume benzinum: ethyl acetate=10:1,9:1,8:1,7:1,6:1,5:1,4:1,3:1,2:1, the each 500mL of ratio preparation eluent of 1:1, for subsequent use;
The krill shrimp sauce sample introduction of getting the above-mentioned preparation of 2ml, first carries out drip washing with 100ml benzinum, then is followed successively by by volume ratioBenzinum: ethyl acetate=10:1,9:1,8:1,7:1,6:1,5:1,4:1,3:1,2:1,1:1 washesDe-liquid carries out drip washing, and collected volume ratio is benzinum: ethyl acetate=3:1,2:1, and the eluent of 1:1, merges, and rotation is steamedSend out and remove benzinum and ethyl acetate, products obtained therefrom is astaxanthin one ester;
(3) prepare AgNO3Efficient lamellae: get the tlc silica gel plate H of 10cm × 20cm, being placed on mass concentration is 1.5％AgNO3Methanol solution in soak 16 minutes, take out and dry 0.5h, then put into 60 DEG C, drying box and dry 2.5h, to obtain final product,For subsequent use.
(4) from refrigerator, (26 DEG C) take out the krill astaxanthin one ester 20mg having prepared, and are dissolved in 1.5ml dichloromethaneIn alkane, obtain astaxanthin one ester solution, get 0.5ml, use capillary microcap point at AgNO3On efficient lamellae, (distance is lower to 1.5cmPlace), sample liquid is put into line, be placed on and be added with 24ml solvent (benzinum: acetone: triethylamine=9.5ml:3ml:10 μ is l)Glass chromatography cylinder [200mm × 200mm(L × H)] in launch; After launching, take out and dry, visible astaxanthin one ester is at lamellaeOn be 2 bands, from upper (referring to solvent front) under be followed successively by: 1. Article 1 red zone Rf is 0.41; 2. Article 2 yellowBand Rf is 0.36; After 2 bands are scraped respectively, put into separately 2 test tubes of carrene, 2 test tubes are simultaneously at 40KHz,Under power 300W condition, ultrasonic extraction 5 minutes, then centrifugal under 5000r/min, gets supernatant, repeats above leaching process4 times colourless to the band scraping, and each gets extract 16ml; Extract rotary evaporation is removed to carrene, obtain 2 parts of astaxanthinsOne ester sample.
Detection method is with embodiment 1.
Testing result: after testing, Article 1 red zone is containing 9% astaxanthin tridecylenic acid one ester and 50% astaxanthin pentadecanoic acidOne ester. The yellow band of Article 2 contains 100% even number astaxanthin aliphatic acid one ester.
Embodiment 3 separates astaxanthin odd-numbered fatty acid one ester (astaxanthin tridecylenic acid one ester and shrimp green grass or young crops from astaxanthin one esterElement pentadecanoic acid one ester)
Step is as follows:
(1) prepare krill shrimp sauce;
(2) extraction of astaxanthin one ester;
First two steps are prepared astaxanthin one ester, the method for embodiment 1 preparation in the patent application that is CN102746205A according to publication numberObtain;
(3) prepare AgNO3Efficient lamellae: get the tlc silica gel plate H of 10cm × 20cm, being placed on mass concentration is 2.5％AgNO3Methanol solution in soak 4 minutes, take out and dry 2.5h, then put into 45 DEG C, drying box and dry 1h, to obtain final product, for subsequent use.
(4) from refrigerator, (26 DEG C) take out the krill astaxanthin one ester 20mg having prepared, and are dissolved in 1.5ml dichloromethaneIn alkane, obtain astaxanthin one ester solution, get 0.5ml, use capillary microcap point at AgNO3On efficient lamellae, (distance is lower to 1.5cmPlace), sample liquid is put into line, be placed on and be added with 24ml solvent (benzinum: acetone: triethylamine=9.5ml:3ml:10 μ is l)Glass chromatography cylinder [200mm × 200mm(L × H)] in launch; After launching, take out and dry, visible astaxanthin one ester is at lamellaeOn be 2 bands, from upper (referring to solvent front) under be followed successively by: 1. Article 1 red zone Rf is 0.41; 2. Article 2 yellowBand Rf is 0.36; After 2 bands are scraped respectively, put into separately 2 test tubes of carrene, 2 test tubes are simultaneously at 40KHz,Under power 500W condition, ultrasonic extraction 3 minutes, then centrifugal under 6000r/min, gets supernatant, repeats above leaching process3 times colourless to the band scraping, and each gets extract 12ml; Extract rotary evaporation is removed to carrene, obtain 2 parts of astaxanthinsOne ester sample.
Detection method is with embodiment 1.
Testing result: after testing, Article 1 red zone is containing 9% astaxanthin tridecylenic acid one ester and 48% astaxanthin pentadecanoic acidOne ester. The yellow band of Article 2 contains 100% even number astaxanthin aliphatic acid one ester.
Claims (5)
1. a method of preparing astaxanthin one ester that is rich in astaxanthin odd-numbered fatty acid one ester, is characterized in that: step is:
(1) prepare krill shrimp sauce: get krill, extract with No. six gasoline, obtain and slightly extract oil, more slightly extract oil with acetone extraction, obtain krill shrimp sauce;
(2) extraction of astaxanthin one ester: 68g200～300 object GF254 silica gel is placed in to 120 DEG C of activation 12h of drying box, then fills post with petroleum ether dissolution, for subsequent use; Be followed successively by by volume benzinum: ethyl acetate=10:1,9:1,8:1,7:1,6:1,5:1,4:1,3:1,2:1, the each 500mL of ratio preparation eluent of 1:1, for subsequent use; The krill shrimp sauce sample introduction of getting the above-mentioned preparation of 2ml, first carries out drip washing with 100ml benzinum, then is followed successively by benzinum by volume ratio: ethyl acetate=10:1,9:1,8:1,7:1,6:1,5:1,4:1,3:1,2:1, the eluent of 1:1 carries out drip washing, collected volume is than being benzinum: ethyl acetate=3:1,2:1, the eluent of 1:1, merge, rotary evaporation is removed benzinum and ethyl acetate, and products obtained therefrom is astaxanthin one ester;
(3) separation of odd-numbered fatty acid one ester: get the astaxanthin one ester 20mg of above-mentioned preparation, be dissolved in 1.5ml carrene, obtain astaxanthin one ester solution, get 0.5ml, use capillary microcap at AgNO3On efficient lamellae, put into line, be then placed in the glass chromatography cylinder that is added with 24ml solvent and launch; After launching, take out and dry, visible astaxanthin one ester is unfolded and is 2 bands, is followed successively by from top to bottom: 1. Article 1 red zone Rf is 0.41; 2. the yellow band of Article 2 Rf is 0.36; 2 bands are scraped, put into the test tube that fills carrene, test tube is placed under 40KHz, 200～500W power to ultrasonic 3～10 minutes, then centrifugal under 4000～6000r/min, get supernatant, repeat above leaching process 3～5 times colourless to the band scraping, obtain respectively the each self-corresponding extract of 2 band, rotary evaporation is removed carrene, obtain 2 kinds of samples, Article 1 red zone is astaxanthin one ester containing 7～9% astaxanthin tridecylenic acid one esters and 48～51% astaxanthin pentadecanoic acid one esters; The yellow band of Article 2 is astaxanthin one ester containing 100% even number astaxanthin aliphatic acid one ester.
2. the method for astaxanthin one ester of astaxanthin odd-numbered fatty acid one ester is rich in preparation according to claim 1, it is characterized in that: described step (1) is specific as follows:
(1) prepare krill shrimp sauce: get krill, at 35 DEG C～65 DEG C, aeration-drying is to constant weight, be crushed to 20 orders, at 30 DEG C, extract 3 times with No. six gasoline, each 1h, oil plant liquor ratio is 1:6, obtain and slightly extract oil, then at 30 DEG C, extract thick extraction oily 3 times, each 0.5h with acetone, solid-liquid ratio is 1:5, obtains krill shrimp sauce.
3. the method for astaxanthin one ester of astaxanthin odd-numbered fatty acid one ester is rich in preparation according to claim 1, it is characterized in that: described AgNO3Efficient lamellae prepares by the following method: the AgNO that is 1～2.5% in mass concentration by tlc silica gel plate H3In methanol solution, soak 4～16 minutes, take out, dry 0.5～2.5 hour, then put into 45～85 DEG C, drying box and dry 0.5～1.5 hour, to obtain final product.
4. the method for astaxanthin one ester of astaxanthin odd-numbered fatty acid one ester is rich in preparation according to claim 1, it is characterized in that: described solvent is that the benzinum, acetone and the triethylamine that are 9.5ml:3ml:10 μ l by volume ratio mix.
5. the method for astaxanthin one ester of astaxanthin odd-numbered fatty acid one ester is rich in preparation according to claim 1, it is characterized in that: the described method that sample is detected is: from 2 samples, respectively get 5mg, respectively adding 0.5ml percentage by volume is 7% concentrated sulfuric acid methanol solution, 60 DEG C of heating water baths 15 minutes, after cooling, add 1ml n-hexane, vibration, leaves standstill and gets supernatant in 2ml small test tube after 5 minutes, and 10h is to becoming solid esterification sample in fume hood volatilization; Then by preparation esterification sample dissolution in n-hexane, on Alilent6890GC-5973MS gas chromatography mass spectrometry chromatograph, detect: chromatographic column #1, Agilent19091N-213:1538.60580HP-INNOWaxPolyethyleneGlyco, 60 DEG C of initial temperatures, pressure 8.3239psi, flow velocity 1ml/min, average speed 36.966cm/s, 1.3653 minutes holdup times, 43 minutes running times.
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| CN109813830A (en) * | 2018-11-29 | 2019-05-28 | 云南中烟工业有限责任公司 | A kind of preparative thin-layer chromatography instrument and its application method |
| CN114989631B (en) * | 2021-03-02 | 2023-06-30 | 西南大学 | Separation and purification method of orange fruit white skin layer blue-changing substance |
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