CN102058727A - Ceramide-containing tea seed extract and preparation method thereof - Google Patents
Ceramide-containing tea seed extract and preparation method thereof Download PDFInfo
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- CN102058727A CN102058727A CN2009101145632A CN200910114563A CN102058727A CN 102058727 A CN102058727 A CN 102058727A CN 2009101145632 A CN2009101145632 A CN 2009101145632A CN 200910114563 A CN200910114563 A CN 200910114563A CN 102058727 A CN102058727 A CN 102058727A
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Abstract
The invention discloses ceramide-containing tea seed extract and a preparation method thereof. The preparation method comprises the following steps of: crushing raw materials, extracting by using water or low-carbon alcohol, and recycling an extraction solvent from the obtained extracting solution so as to obtain extract, wherein the raw materials are seeds of theaceae camellia plants, namely camellia oleifera abel, camellia or common camellia, or residues of the seeds of the plants subjected to oil component extraction; adding alkaline solution into the extract, and hydrolyzing at the temperature of between 10 and 80 DEG C for 0.5 to 20 hours; and separating the obtained hydrolyzate by using a macroporous resin column, performing chromatography through a silica gel column or a sephadex column, eluting by using 40 to 60 volume percent aqueous solution of methanol or ethanol, performing thin layer chromatography, collecting fractions, mixing the fractions, and drying to obtain the ceramide-containing tea seed extract. The raw materials are readily available and the method is environmentally-friendly; the preparation process is simple; the product quality is stable; the production cost is low; and the content of ceramide in the extract is high.
Description
Technical field
The present invention relates to extraction of active ingredients in the plant, be specifically related to camellia oleosa seed extract that contains ceramide and preparation method thereof.
Background technology
Ceramide (Ceramide) is formed by amido link and fatty acid covalent bond by the long-chain sphingol.Because the difference of the carbon chain lengths of sphingol in the ceramide molecule, the difference of degree of unsaturation and degree of hydroxylation, and the length that is connected to the fatty acid on the sphingol by amido link, the number of unsaturated bond and hydroxyl, position different and show very big difference, so the definite ceramide of saying is not a kind of material, but class material of structural similarity.Kristi JRobSon etc. once did detailed research to the ceramide in the keratodermatitis, according to the difference of structure and ceramide is divided into 7 kinds.Generally according to different Ceramide (the I)-Ceramide (VII) that are divided into of its saturation and hydroxy radical content, their structural formula is as follows for ceramide:
Ceramide is one of class lipid structural unit of bimolecular lipid layer component sphingomyelins, has important biological action, as barrier, water conservation, courier's effect and startup apoptosis etc.In recent years, it is particularly noticeable in the function of regulating aspects such as apoptosis, cell differentiation, transhipment and propagation.Someone thinks that ceramide plays a role in such as physiological process such as cancer, neurasthenia, diabetes, obesity and inflammation.Ceramide is the important composition component of skin.The outermost layer of skin is an epidermal area, and the outermost layer of epidermis is a horny layer.Though only 10～30 microns of cuticle thickness only are 1/10th of paper sheet thickness, it is the main barrier of skin, can stop the chemical substance of following contact skin to be absorbed and enter in the human body, and stop subcutaneous moisture to ooze out.Ceramide is born the key player in the barrier action of skin; In horny layer, as most important lipoid composition, ceramide and O-acyl group ceramide account for half of its lipid constituent.Studies show that ceramide can thicken horny layer, thereby play a part to water conservation and whiten.Research has confirmed also that the ceramide related substances also has and has prevented that extraneous pathogen transdermal from entering in the body and effect such as opposing allergic dermatitis.
Dark people along with ceramide research has caused the concern of more and more researchers.Present ceramide product has natural and synthetic two kinds, and natural ceramide mainly is to extract from animal brain, but because bovine spongiform encephalopathy potential hazard and animal protection ist's opposition, makes the progressively atrophy of ceramide of animal origin.Because synthetic ceramide is a chemicals, development from now on also has limitation.Therefore, from natural plants, extracting ceramide, but have broad prospects. ceramide is very limited at the content of organism, and the biomaterial of seeking to be rich in ceramide has become the focus of the exploitation and the research of ceramide.Up to now, the known plant that contains more ceramide has Semen Tritici aestivi, rice, Semen sojae atricolor and aspergillus etc.In addition, also contain more ceramide in the Rhizoma amorphophalli.
The extracting method of disclosed ceramide is a lot of at present, as with rice (Agric.Biol.Chem., 49,2753 (1985)) and Semen Tritici aestivi (Agric.Biol.Chem., 49,3609 (1985)) ceramide derivatives that extracts for raw material, with the Rhizoma amorphophalli is raw material extraction separation ceramide type material (biotechnology, 2007 the 10th phases, the 17th the 5th phase of volume, 45～47 pages), and the plant of theaceae extract that contains ceramide is also disclosed among the Japan Patent JP2004189683, but these extracting method all exist technology complicated, the deficiency that cost is higher.
Summary of the invention
The technical problem to be solved in the present invention provides a kind of camellia oleosa seed extract that contains ceramide and preparation method thereof.This method is passed through to extract the ceramide type material from the seed of plant of theaceae or seed the residue after oil expression, and technology is simple, easily control, and the content of extract obtained middle ceramide can reach more than 60%.
The camellia oleosa seed extract that contains ceramide of the present invention, it is to be raw material with the residue after the oil expression of the seed of Theaceae Camellia plant oil tea, Flos Camelliae Japonicae or tea or its seed, water or low-carbon alcohols are extracted, extracting solution is through hydrolysis, resin column separation, silicagel column or polydextran gel column chromatography purification, drying and what make is the extract of main component with the ceramide, and wherein the weight content of ceramide is 0.01～90%.
The above-mentioned camellia oleosa seed preparation method of extract that contains ceramide may further comprise the steps:
1) get raw material, pulverize, water or low-carbon alcohols are extracted 1～3 time, extract 0.5～20h at every turn, and merge extractive liquid, reclaims and extracts solvent, gets extractum; Wherein, described raw material is the seed of Theaceae Camellia plant oil tea, Flos Camelliae Japonicae or tea, or the residue of the seed of above-mentioned plant after extracting lubricant component;
2) add alkaline solution in extractum and be hydrolyzed, the temperature of hydrolysis is 10～100 ℃, and the time is 0.5～20h;
3) hydrolyzed solution advances the macroporous resin column separation, and the washed resin post is colourless to effluent, is 3～5: 1 methanol-water or ethanol-water mixed solvent eluting then with volume ratio, collects eluent, concentrating under reduced pressure, and drying gets the camellia oleosa seed crude extract;
4) silicagel column or polydextran gel column chromatography on the camellia oleosa seed crude extract are 40～60% methanol or ethanol water eluting with volumetric concentration, and thin layer chromatography detects, and collect flow point, merge flow point, drying, promptly.
In the above-mentioned preparation method:
In the step 3), hydrolyzed solution can separate with advancing resin column again after petroleum ether, cyclohexane extraction or the industrial naptha extraction earlier.The consumption of described petroleum ether, cyclohexane extraction or industrial naptha can be 1～5 times of hydrolyzed solution volume.
In the step 1), described oil tea is the oil tea (C.oleifera.linn) of Theaceae Camellia, is the peculiar woody edible oil materials seeds of China, is distributed widely in southern provinces and regions such as Hunan, Guizhou, Jiangxi, Guangxi.Flos Camelliae Japonicae is the Flos Camelliae Japonicae (C.japonica.L) in the Flos Camelliae Japonicae subgenus Red Hill tea group.Tea is Camellia plant Camellia sinensis (C.sinensis O Ktze).The granularity that seed of above-mentioned plant or the seed residue after oil expression is pulverized is advisable with 20～80 orders.
Described low-carbon alcohols is methanol, ethanol or n-butyl alcohol, and its volumetric concentration is 50～100%.Extracting temperature is 10～100 ℃, and the solid-liquid ratio during extraction is 1: 1～10 (W/V), and preferred 2～5: 1 (W/V), extracting mode can be and stir extraction, immersion extraction, microwave or ultrasonic assisted extraction, reflux, extract,, Soxhlet is extracted or percolation extracts.Wherein the supersonic frequency of microwave or ultrasonic assisted extraction is 40～100MHz, and the speed that percolation extracts is 1～4BV/h.
Step 2) in, described alkaline solution is that mass concentration is 10～40% sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, sodium bicarbonate or sodium hydrogen phosphate aqueous solution, and its addition is 0.5～10 times of raw material weight.
In the step 3), the model of described macroporous resin is D101, D102, AB-8 or DM131.The consumption of eluant methanol-water or ethanol-water mixed solvent is 1～5 times of bed volume.
The applicant finds, contains a large amount of lipid components (accounting for more than 20% of dry matter weight) in the camellia oleosa seed of above-mentioned plant or the residue of camellia oleosa seed after oil expression, wherein is the ceramide type material that can be applicable to cosmetics and pharmaceutical raw material greatly.Because camellia oleosa seed is Chinese edible oil materials raw material, and the residue of camellia oleosa seed after oil expression is the by-product in the edible vegetable oil material production process, it is as a kind of hair washing, hair care articles, among the peoplely is widely used in China, historical remote, and its safety and supply all can be protected.Simultaneously because ceramide content is higher in camellia oleosa seed and the camellia oleosa seed residue after oil expression, with as the natural ceramide of raw material production, have great cost advantage.
Compared with prior art, the present invention is by extracting the ceramide type material from plant of theaceae, and raw material is easy to get, environmental protection, simple, the easily control of preparation technology, constant product quality, production cost is low, and the content of extract obtained middle ceramide can reach (HPLC-ELSD method mensuration) more than 60%.
Description of drawings
The HPLC-ELSD collection of illustrative plates of ceramide in the extract that Fig. 1 prepares for embodiment 1;
The HPLC-ELSD collection of illustrative plates of ceramide in the extract that Fig. 2 prepares for embodiment 2.
The specific embodiment
The invention will be further described with embodiment below, but the present invention is not limited to these embodiment.
Embodiment 1
1) extract, concentrate: with the residue of oil tea seed after lubricant component is extracted in squeezing is raw material, is crushed to 20 orders, puts into extraction vessel, add 95% (v/v) ethanol that is equivalent to 3 times of raw material weights, the control temperature is at 80 ℃, and reflux, extract, 30min isolates medicinal liquid for the first time; Add 95% (v/v) ethanol that is equivalent to 4 times of raw material weights for the second time again, reflux, extract, 30min under 80 ℃ of conditions, merge extractive liquid,, decompression recycling ethanol gets extractum;
2) hydrolysis: adding in extractum and being equivalent to 5 times of raw material weights, mass concentration is that 10% sodium hydroxide solution is hydrolyzed, and the temperature of hydrolysis is 25 ℃, and the time is 15h;
3) extraction: hydrolyzed solution petroleum ether extraction 2 times merge extraction phase; The consumption of petroleum ether is 5 times of hydrolyzed solution volume during extraction;
4) the gained extract advances the separation of D101 type macroporous resin column, and the washed resin post is colourless to effluent, uses ethanol-water mixed solvent (volume ratio is 4: the 1) eluting of 3 times of bed volumes then, collects eluent, concentrating under reduced pressure, and drying gets the camellia oleosa seed crude extract;
5) the camellia oleosa seed crude extract is gone up silica gel column chromatography with suitable quantity of water dissolving back, is 50% methanol solution eluting with volumetric concentration, and thin layer chromatography detects, and collects flow point, the merging flow point, and drying promptly gets the camellia oleosa seed extract that contains ceramide.
Above-mentioned extract obtained NMR detects data:
[α]
25 D-7.9 ° of (C=0.1CHCl
3),
1H-NMR (in pyridine-ds) δ: 8.38 (1H, d, J=8.5Hz ,-NH), 4.79 (1H, brs, H-2), 4.71 (1H, dd, J=10.4,6.1Hz, H-3), 4.60 (1H, br s, H-1), 4.51 (1H, brs, H-2 ') are the ceramide characteristic group by analysis.Wherein the content of ceramide is 80% (HPLC-ELSD method mensuration).
Embodiment 2
1) extract, concentrate: with the residue behind the camellia seeds extraction lubricant component is raw material, is crushed to 40 orders, puts into extraction vessel, adds 90% (v/v) methanol that is equivalent to 5 times of raw material weights, and the control temperature stirs and extracts 90min at 60 ℃, isolates medicinal liquid; Repeat above-mentioned condition and carry out stirring the second time extraction again; Merge extractive liquid,, reclaim under reduced pressure methanol gets extractum;
2) hydrolysis: adding in extractum and being equivalent to 5 times of raw material weights, mass concentration is that 10% potassium hydroxide solution is hydrolyzed, and the temperature of hydrolysis is 50 ℃, and the time is 3h;
3) extraction: hydrolyzed solution merges extraction phase with cyclohexane extraction extraction 2 times; The consumption of cyclohexane extraction is 1 times of hydrolyzed solution volume during extraction;
4) the gained extract advances the separation of DM131 type macroporous resin column, and the washed resin post is colourless to effluent, uses ethanol-water mixed solvent (volume ratio is 3: the 1) eluting of 5 times of bed volumes then, collects eluent, concentrating under reduced pressure, and drying gets the camellia oleosa seed crude extract;
5) the camellia oleosa seed crude extract being gone up the polydextran gel column chromatography with suitable quantity of water dissolving back, is 40% alcoholic solution eluting with volumetric concentration, and thin layer chromatography detects, and collects flow point, the merging flow point, and drying promptly gets the camellia oleosa seed extract that contains ceramide.
The content of above-mentioned extract obtained middle ceramide is 69%, and Fig. 2 detects the HPLC-ELSD collection of illustrative plates that obtains for this extract with HPLC, and as we know from the figure, ceramide component retention time is 9.17min and 9.84min.
Embodiment 3
1) extract, concentrate: with the Camellia sinensis seed is raw material, is crushed to 80 orders, puts into extraction vessel, adds the water that is equivalent to 10 times of raw material weights, is heated to 80 ℃ and carries out the lixiviate first time, and the time is 10h, isolates medicinal liquid; Add the water that is equivalent to 5 times of raw material weights for the second time again, be heated to 100 ℃ and carry out the lixiviate second time, the time is 3h, isolates medicinal liquid; Add the water that is equivalent to 1 times of raw material weight for the third time again, be heated to 60 ℃ and carry out lixiviate for the third time, the time is 1h, merge extractive liquid,, and concentrating under reduced pressure gets extractum;
2) hydrolysis: adding in extractum and being equivalent to 0.5 times of raw material weight, mass concentration is that 30% sodium carbonate liquor is hydrolyzed, and the temperature of hydrolysis is 80 ℃, and the time is 1h;
3) the gained hydrolyzed solution advances the separation of AB-8 type macroporous resin column, and the washed resin post is colourless to effluent, uses methanol-water mixed solvent (volume ratio is 5: the 1) eluting of 4 times of bed volumes then, collects eluent, concentrating under reduced pressure, and drying gets the camellia oleosa seed crude extract;
4) the camellia oleosa seed crude extract being gone up silica gel column chromatography with suitable quantity of water dissolving back, is 60% alcoholic solution eluting with volumetric concentration, and thin layer chromatography detects, and collects flow point, the merging flow point, and drying promptly gets the camellia oleosa seed extract that contains ceramide.
The content of above-mentioned extract obtained middle ceramide is 75% (HPLC-ELSD method mensuration).
Embodiment 4
1) extract, concentrate: with the oil tea seed is raw material, is crushed to 50 orders, puts into percolator, adds 50% (v/v) n-butyl alcohol that is equivalent to 9 times of raw material weights, be heated to 50 ℃ of beginning percolation, percolation speed is 1BV/h, time 20h, collect percolate, concentrate, get extractum;
2) hydrolysis: adding in extractum and being equivalent to 8 times of raw material weights, mass concentration is that 20% aqua calcis is hydrolyzed, and the temperature of hydrolysis is 60 ℃, and the time is 10h;
3) the gained hydrolyzed solution advances the separation of D102 type macroporous resin column, and the washed resin post is colourless to effluent, uses methanol-water mixed solvent (volume ratio is 3.5: the 1) eluting of 4 times of bed volumes then, collects eluent, concentrating under reduced pressure, and drying gets the camellia oleosa seed crude extract;
4) the camellia oleosa seed crude extract being gone up silica gel column chromatography with suitable quantity of water dissolving back, is 55% methanol solution eluting with volumetric concentration, and thin layer chromatography detects, and collects flow point, the merging flow point, and drying promptly gets the camellia oleosa seed extract that contains ceramide.
The content of above-mentioned extract obtained middle ceramide is 83% (HPLC-ELSD method mensuration).
1) extract, concentrate: with the camellia seeds is raw material, is crushed to 80 orders, puts into extraction vessel, adds the water that is equivalent to 8 times of raw material weights, and supersound extraction 50min under 20 ℃, 80MHz condition isolates medicinal liquid; Add the water that is equivalent to 6 times of raw material weights for the second time again, be heated to 70 ℃, supersound extraction 30min under the 70MHz condition, merge extractive liquid,, concentrating under reduced pressure gets extractum;
2) hydrolysis: adding in extractum and being equivalent to 10 times of raw material weights, mass concentration is that 40% sodium bicarbonate solution is hydrolyzed, and the temperature of hydrolysis is 40 ℃, and the time is 20h;
3) the gained hydrolyzed solution advances the separation of AB-8 type macroporous resin column, and the washed resin post is colourless to effluent, uses ethanol-water mixed solvent (volume ratio is 5: the 1) eluting of 5 times of bed volumes then, collects eluent, concentrating under reduced pressure, and drying gets the camellia oleosa seed crude extract;
4) the camellia oleosa seed crude extract being gone up silica gel column chromatography with suitable quantity of water dissolving back, is 45% methanol solution eluting with volumetric concentration, and thin layer chromatography detects, and collects flow point, the merging flow point, and drying promptly gets the camellia oleosa seed extract that contains ceramide.
The content of above-mentioned extract obtained middle ceramide is 80% (HPLC-ELSD method mensuration).
Claims (9)
1. the camellia oleosa seed extract that contains ceramide, it is characterized in that: it is to be raw material with the residue after the oil expression of the seed of Theaceae Camellia plant oil tea, Flos Camelliae Japonicae or tea or its seed, water or low-carbon alcohols are extracted, extracting solution is through hydrolysis, resin column separation, silicagel column or polydextran gel column chromatography purification, drying and what make is the extract of main component with the ceramide, and wherein the weight content of ceramide is 0.01～90%.
2. the described camellia oleosa seed preparation method of extract that contains ceramide of claim 1 is characterized in that may further comprise the steps:
1) get raw material, pulverize, water or low-carbon alcohols are extracted 1～3 time, extract 0.5～20h at every turn, and merge extractive liquid, reclaims and extracts solvent, gets extractum; Wherein, described raw material is the seed of Theaceae Camellia plant oil tea, Flos Camelliae Japonicae or tea, or the residue of the seed of above-mentioned plant after extracting lubricant component;
2) add alkaline solution in extractum and be hydrolyzed, the temperature of hydrolysis is 10～100 ℃, and the time is 0.5～20h;
3) hydrolyzed solution advances the macroporous resin separation, and the washed resin post is colourless to effluent, is 3～5: 1 methanol-water or ethanol-water mixed solvent eluting then with volume ratio, collects eluent, concentrating under reduced pressure, and drying gets the camellia oleosa seed crude extract;
4) silicagel column or polydextran gel column chromatography on the camellia oleosa seed crude extract are 40～60% methanol or ethanol water eluting with volumetric concentration, and thin layer chromatography detects, and collect flow point, merge flow point, drying, promptly.
3. the camellia oleosa seed preparation method of extract that contains ceramide according to claim 2 is characterized in that: in the step 3), hydrolyzed solution with petroleum ether, cyclohexane extraction or industrial naptha extraction, advances resin column again and separates earlier.
4. according to claim 2 or the 3 described camellia oleosa seed preparation method of extract that contain ceramide, it is characterized in that: in the step 1), low-carbon alcohols is methanol, ethanol or n-butyl alcohol, and its volumetric concentration is 50～100%.
5. according to claim 2 or the 3 described camellia oleosa seed preparation method of extract that contain ceramide, it is characterized in that: in the step 1), extracting temperature is 10～100 ℃, solid-liquid ratio during extraction is 1: 1～10 (W/V), and extracting mode extracts, soaks extraction, microwave or ultrasonic assisted extraction, reflux, extract, for stirring, Soxhlet is extracted or percolation extracts.
6. according to claim 2 or the 3 described camellia oleosa seed preparation method of extract that contain ceramide, it is characterized in that: step 2) in, described alkaline solution is that mass concentration is 10～40% sodium hydroxide, potassium hydroxide, calcium hydroxide, sodium carbonate, sodium bicarbonate or sodium hydrogen phosphate aqueous solution, and its addition is 0.5～10 times of raw material weight.
7. according to claim 2 or the 3 described camellia oleosa seed preparation method of extract that contain ceramide, it is characterized in that: in the step 3), the model of described macroporous resin is D101, D102, AB-8 or DM131.
8. according to claim 2 or the 3 described camellia oleosa seed preparation method of extract that contain ceramide, it is characterized in that: in the step 3), the consumption of methanol-water or ethanol-water mixed solvent is 1～5 times of bed volume.
9. the camellia oleosa seed preparation method of extract that contains ceramide according to claim 2 is characterized in that: the consumption of described petroleum ether, cyclohexane extraction or industrial naptha is 1～5 times of hydrolyzed solution volume.
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| CN103060080A (en) * | 2013-01-06 | 2013-04-24 | 湖南金浩茶油股份有限公司 | Preparation method of blood-fat-reducing camellia oil |
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Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2732680B1 (en) * | 1995-04-05 | 1997-05-09 | Oreal | CERAMID-LIKE COMPOUNDS, PROCESS FOR THEIR PREPARATION AND THEIR USE |
| JP2004189683A (en) * | 2002-12-12 | 2004-07-08 | Nagase & Co Ltd | Ceramide production promoter |
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| US11464247B2 (en) | 2006-09-07 | 2022-10-11 | Guilin Gfs Monk Fruit Corp. | Sweetening compositions and processes for preparing them |
| CN103060080A (en) * | 2013-01-06 | 2013-04-24 | 湖南金浩茶油股份有限公司 | Preparation method of blood-fat-reducing camellia oil |
| CN103060080B (en) * | 2013-01-06 | 2013-11-20 | 湖南金浩茶油股份有限公司 | Preparation method of blood-fat-reducing camellia oil |
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| CN108947864A (en) * | 2018-06-08 | 2018-12-07 | 三原利华生物技术有限公司 | A kind of preparation method of ceramide |
| CN109692131A (en) * | 2019-01-25 | 2019-04-30 | 江南大学 | The preparation method and product of ceramide extract in a kind of sapindaceous plant seed |
| CN109692131B (en) * | 2019-01-25 | 2021-08-10 | 江南大学 | Preparation method of ceramide extract in sapindaceae plant seeds and product |
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Address after: No. 19 Renmin South Road, Lingui District, Guilin City, Guangxi Zhuang Autonomous Region, 541100 Patentee after: GUILIN LAYN NATURAL INGREDIENTS Corp. Address before: 541100 Yangtang Industrial Park, Lingui Town, Lingui County, Guilin City, Guangxi Zhuang Autonomous Region Patentee before: GUILIN LAYN NATURAL INGREDIENTS Corp. |
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