CN106755254A - A kind of method of the Enzyme catalyzed synthesis lipoic acid sterol ester in organic phase - Google Patents
A kind of method of the Enzyme catalyzed synthesis lipoic acid sterol ester in organic phase Download PDFInfo
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- CN106755254A CN106755254A CN201611242224.9A CN201611242224A CN106755254A CN 106755254 A CN106755254 A CN 106755254A CN 201611242224 A CN201611242224 A CN 201611242224A CN 106755254 A CN106755254 A CN 106755254A
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Abstract
The invention discloses a kind of method of the Enzyme catalyzed synthesis lipoic acid sterol ester in organic phase, belong to the technical fields such as food, medicine and cosmetics.The present invention uses lipase-catalyzed synthesis lipoic acid sterol ester in organic phase, and it is 71.2% to obtain the yield of lipoic acid sterol ester, and purity is 99.3%.Production by Enzymes reaction condition that the inventive method is used is gentle, step is simple, products therefrom purity and the features such as high income; without protective group, only need single step reaction, raw material, the catalysts and solvents of selection also all can safety applications in food; environmentally friendly, Product Safety is high.
Description
Technical field
The present invention relates to a kind of method of the Enzyme catalyzed synthesis lipoic acid sterol ester in organic phase, belong to food, medicine and
The technical fields such as cosmetics.
Background technology
Phytosterol is a class abundance and the natural products with different physiological roles, belongs to steroid chemical combination
Thing, molecule C-3 is connected with a hydroxyl, a C-17 hydrophobic side chain for 9-10 carbon atom composition of ining succession.Phytosterol is
The important food function factor of one class, with many important physiological functions, such as effective prevention of cardiovascular disease, anti-oxidant decline
Always, various important physiological functions such as anticancer, anti-inflammatory.
The unique chemical constitution of phytosterol determines its water-insoluble and low oil-soluble, limits it in the food industry
Application.Additionally, the absorptivity in human body to the phytosterol that dissociates is only 3%, the excessive phytosterol of intake occurs new
Illness, i.e., phytosterol mass formed by blood stasis high, so the solubility and bioavailability that how to improve phytosterol are matters of utmost importance.Not
It is modified on the premise of influence phytosterol physiological function, improving its bioavilability turns into the focus of research.Sterol
It is referred to as sterol ester after esterification, is a class of most study in phytosterol derivative, compared to phytosterol, the change of chemical constitution
Change has no effect on its physiological function, and what is had also has certain humidification.
There are many document reports to be modified research to phytosterol for the purpose of the solubility for improving sterol in recent years, such as
Sterol and laurate, glutamic acid etc. are esterified or microcapsules etc. are prepared.But there is high energy consumption, step mostly in these methods
It is cumbersome, the problems such as security is unknown, it is restricted its practical application.Therefore, if can select some can safety applications in food
The functional materials in product field carry out gentle single step reaction with phytosterol, can not only improve lacking in respective physicochemical property
Fall into, improve its bioavilability, and respective function can be retained again or acted synergistically, so as to realize that modified synergistic is carried
Matter.
Lipoic acid is a kind of very strong natural of oxidation resistance, and is risen in various metabolic processes important
Effect, therefore extensive research and application have been obtained in fields such as medicine, food, such as medicine, the antioxygen for the treatment of diabetes
Change health food etc..The lipoic acid sterol ester that sterol is produced after being esterified with lipoic acid in theory can be same after being decomposed through absorption of human body
The function of Shi Fahui both materials.Also rarely have the relevant report on lipoic acid phytosterin ester, only Samanthi at present
R.P.Madawala et al. reported the chemical preparation process of over cure octanoic acid sterol ester in 2012, and specific method is：By the steroid of 1g
After alcohol is dissolved in the DMAP of 9mL dichloromethane and 64mg, in the case where nitrogen is passed through, in the sulphur that addition 580mg is stirred at 0 DEG C
The EDCI of octanoic acid and 468mg, is then stirred at room temperature one night of reaction, and the yield for finally giving is 60%.The method it is last with
N-hexane is solvent, is isolated and purified using solid-phase extraction column, and is demonstrated by DPPH radicals scavengings experiment
The lipoic acid sterol ester of synthesis has certain inoxidizability.
The content of the invention
The purpose of the present invention is to provide one kind improving the physicochemical property of phytosterol, effect and to improve bioavilability
Prepared by enzyme process, the method for purifying lipoic acid sterol ester.This method reaction condition is gentle, step is simple, products therefrom purity and receipts
Rate is high, can safety applications in industries such as food, medicine.
The preparation method that the present invention is provided, is one kind Enzyme catalyzed synthesis lipoic acid sterol ester in organic phase, is in constant temperature
Under conditions of vibration, in organic phase, with phytosterol, lipoic acid as substrate, lipoic acid is synthesized as catalyst with lipase
Sterol ester；The organic phase is with volume ratio 1：N-hexane, the acetone of 1 mixing, or with volume ratio 1：The tert-pentyl alcohol of 1 mixing,
N-hexane；The lipase is Novozyme 435 or Candida Rugosa；The initial concentration of the phytosterol be 100~
200mmol/L, lipase addition is 60~80g/L, and acid alcohol mol ratio is (2~3)：1；Reaction temperature is 50 DEG C~60 DEG C,
Reaction time is 72~120h.
In one embodiment of the invention, the initial concentration of the phytosterol is 100~150mmol/L.
In one embodiment of the invention, the initial concentration of the phytosterol is 150mmol/L.
In one embodiment of the invention, lipase addition used is 60g/L.
In one embodiment of the invention, acid alcohol mol ratio is 2.5：1
In one embodiment of the invention, reaction density used is 55 DEG C.
In one embodiment of the invention, the molecular sieve of 0~20g/L is also added in reaction system；Molecular sieve
Species is 3A or 4A.
In one embodiment of the invention, lipase used is Candida Rugosa.
In one embodiment of the invention, molecular sieve addition used is 10g/L, and the species of molecular sieve is 4A.
In one embodiment of the invention, the reaction time used is 96h.
In one embodiment of the invention, by volume 1：The n-hexane of 1 mixing and the mixed solution of tert-pentyl alcohol
In, the Candida Rugosa of 60g/L are added, molecular sieve concentration is 10g/L, sterol initial concentration 150mmol/L, acid alcohol mole
Than being 2.5：1, react 96h under the conditions of 55 DEG C, 150rpm.
In one embodiment of the invention, also including isolating and purifying product, first go to dezymotize and molecular sieve, use
After Rotary Evaporators removal solvent, solute is dissolved with the solvent of thin-layer chromatography, then through silica gel column chromatography after, by thin-layer chromatography
Detection, collects different sections of component, you can the lipoic acid sterol ester for being purified；The silica gel column chromatography mobile phase is by volume
Than 15：The petroleum ether of 1 mixing: ethyl acetate；The solvent of thin-layer chromatography detection is by volume 15：The oil of 1 mixing
Ether: ethyl acetate.
In one embodiment of the invention, purity and yield also are determined using high-efficient liquid phase technique (HPLC), it is red
External spectrum (FT-IR) and mass spectrum (MS) identification structure.
Beneficial effects of the present invention：
(1) present invention has synthesized lipoic acid sterol ester, improves the solubility of sterol, improves the biological utilisation of sterol
Degree, and be beneficial to turn into a kind of with functional antioxidant.
(2) using the present invention in organic solvent using the lipase-catalyzed method for preparing lipoic acid sterol ester, Ke Yi great
The big conversion ratio for improving ester, more than 71.2%, purity reaches more than 99.3% to conversion ratio.
(3) the inventive method is used Production by Enzymes reaction condition is gentle, step is simple, products therefrom purity and high income
The features such as, without protective group, only need single step reaction, raw material, the catalysts and solvents of selection also all can safety applications in food
Environmentally friendly in product, Product Safety is high.
Brief description of the drawings
Fig. 1 is the structural formula of lipoic acid phytosterin ester.
Fig. 2 is the HPLC collection of illustrative plates of lipoic acid stigmasterol ester.
Fig. 3 is the infrared spectrogram of lipoic acid stigmasterol ester.
Fig. 4 is the mass spectrogram of lipoic acid stigmasterol ester.
Specific embodiment
The authentication method of product：Using Fourier transform infrared spectroscopy and the structure of Mass Spectrometric Identification lipoic acid sterol ester.FT-
IR analyses use Thermo Scientific Nicolet i S10 FTISs, from KBr pressed disc methods,
Scanning times：32 times, resolution ratio：4cm-1.Mass spectral analysis uses Waters UPLC-TQD mass spectrographs, the sample that will be isolated and purified
The sample introduction after 0.22 μm of miillpore filter, ion gun is electron spray (ESI) ion gun, capillary voltage 3.5kV, desolventizing temperature
250 DEG C, Desolvention gas velocity 500L/h, taper hole gas velocity 50L/h, taper hole voltage 20V, collision energy 6V, detector voltage
1700V, 50~1000m/z of mass range.
The computational methods of esterification yield and product purity：The present invention using HPLC determine lipoic acid phytosterin ester purity and
Yield, HPLC-ELSD analysis systems include Waters1525 high performance liquid chromatographs, Alltech3300 Evaporative light scattering detectors
Device (ELSD) and Empower data processing softwares.Chromatographic column is Waters symmetry C18 reversed-phase columns (4.6 × 250mm, 5 μ
M), column temperature：45 DEG C, mobile phase: 100% methyl alcohol, flow velocity：1mL/min, constant speed wash-out, sample size：10μL；ELSD parameters：Temperature
It it is 55 DEG C, carrier gas is nitrogen, flow velocity is 1.5L/min, and gain is 1.
The computational methods of specific esterification rate are：The lipoic acid sterol ester that will be isolated and purified prepares a series of various concentrations respectively
Solution, determine each peak area using HPLC, the linear relationship system of the logarithm value according to sample peak area and the logarithm value of concentration
Make standard curve, obtain equation for lgA=1.41lgC+6.77.After by the reaction solution sample introduction after esterification, further according to peak area meter
The concentration of lipoic acid phytosterin ester in reaction solution is calculated, esterification yield can be calculated further according to following equation.
XPSE(%)=CPSE/CPS× 100, X in formulaPSEIt is the esterification yield of lipoic acid sterol ester, CPSEIt is lipoic acid sterol ester
Concentration (mol/L), CPSStart the concentration (mol/L) of phytosterol for reaction.
Total peak area × 100 of the peak area/all samples of purity (the %)=lipoic acid sterol ester of lipoic acid sterol ester
Influence of the species of the reaction dissolvent of embodiment 1 and enzyme to synthesis lipoic acid sterol ester
In the tert-butyl alcohol, tert-pentyl alcohol, n-hexane, acetone/n-hexane, (volume ratio is 1 respectively:1), the n-hexane/tert-butyl alcohol (body
Product is than being 1:1) (volume ratio is 1 with tert-pentyl alcohol/n-hexane:1) in, the Novozyme 435 of 20g/L is added respectively
(10000PLU/g, purchased from Beijing Gao Ruisen Science and Technology Ltd.s), Lipase from Candida Rugosa (847U/mg, purchase
From Sigma), Lipozyme TL IM (250IUN/g, purchased from Beijing Gao Ruisen Science and Technology Ltd.s), Lipozyme RM IM
(275IUN/g, purchased from Beijing Gao Ruisen Science and Technology Ltd.s), the 4A molecular sieves of 40g/L, the phytosterol of 50mmol/L, acid alcohol
Mol ratio is 1.5：1, react 72h under the conditions of 45 DEG C, 150rpm.Esterification yield is as shown in table 1 below：
Influence of the species of the reaction dissolvent of table 1 and enzyme to synthesis lipoic acid sterol ester
Influence of the phytosterol initial concentration of embodiment 2 to synthesis lipoic acid sterol ester
It is n-hexane/tert-pentyl alcohol from organic phase on the basis of embodiment 1, enzyme is Candida Rugosa, then is distinguished
The initial concentration of phytosterol is adjusted to 25mmol/L, 50mmol/L, 100mmol/L, 150mmol/L and 200mmol/L, is tied
Really show when sterol concentration is 150mmol/L, esterification yield highest.Esterification yield such as following table under different phytosterol concentration conditions
Shown in 2：
Influence of the phytosterol initial concentration of table 2 to synthesis lipoic acid sterol ester
| Sterol initial concentration (mmol/L) | Esterification yield (%) |
| 25 | 5.6 |
| 50 | 6.8 |
| 100 | 8.6 |
| 150 | 10.2 |
| 200 | 7.8 |
Influence of the acid alcohol mol ratio of embodiment 3 to synthesis lipoic acid sterol ester
It is 150mmol/L from sterol concentration on the basis of embodiment 2, then respectively by lipoic acid and phytosterol
Mol ratio is adjusted to 1：1.5、1：1、1.5：1、2：1、2.5：1、3：1 and 3.5：1.At the beginning with the increase of acid alcohol mol ratio,
Conversion ratio is constantly raised, but when acid alcohol mol ratio is more than 2.5：When 1, yield is declined slightly.Under different acid alcohol molar ratios
Esterification yield is as shown in table 3 below：
Influence of the acid alcohol mol ratio of table 3 to synthesis lipoic acid sterol ester
| Acid alcohol mol ratio | Esterification yield (%) |
| 1:1.5 | 8.3 |
| 1:1 | 5.6 |
| 1.5:1 | 9.7 |
| 2:1 | 13.1 |
| 2.5:1 | 16.1 |
| 3:1 | 11.3 |
The influence of the molecular sieve species of embodiment 4 and addition to synthesis lipoic acid sterol ester
It is 2.5 from acid alcohol mol ratio on the basis of embodiment 3：1, then respectively by the molecular sieve concentration of 3A and 4A types
0g/L, 10g/L, 20g/L, 30g/L and 40g/L are adjusted to respectively.The sample esterification yield for adding 3A type molecular sieves will be significantly lower than
The sample of 4A type molecular sieves is added, and when 4A type molecular sieves concentration is 10g/L, yield highest, with molecular sieve addition
Increase, reaction conversion ratio is gradually reduced.Esterification yield under the conditions of different molecular sieve addition is as shown in table 4 below：
The influence of the molecular sieve species of table 4 and addition to synthesis lipoic acid sterol ester
Influence of the lipase addition of embodiment 5 to synthesis lipoic acid sterol ester
It is 10g/L from molecular sieve addition, then lipase addition is adjusted to respectively on the basis of embodiment 4
20g/L, 40g/L, 60g/L and 80g/L.Result shows that lipase addition is more, and conversion ratio is higher, when addition is more than
During 60g/L, yield tends towards stability.Esterification yield under the conditions of different enzyme additions is as shown in table 5 below：
Influence of the lipase addition of table 5 to synthesis lipoic acid sterol ester
Influence of the reaction temperature of embodiment 6 to synthesis lipoic acid sterol ester
On the basis of embodiment 5, from lipase addition be 60g/L, then reaction temperature is adjusted to respectively 40 DEG C,
45 DEG C, 50 DEG C, 55 DEG C and 60 DEG C, as a result find conversion ratio highest at 55 DEG C.Esterification yield under differential responses temperature conditionss is as follows
Shown in table 6：
Influence of the reaction temperature of table 6 to synthesis lipoic acid sterol ester
| Reaction temperature (DEG C) | Esterification yield (%) |
| 40 | 41.8 |
| 45 | 46.7 |
| 50 | 51.4 |
| 55 | 56.2 |
| 60 | 50.3 |
Influence of the reaction time of embodiment 7 to synthesis lipoic acid sterol ester
On the basis of embodiment 6, from reaction temperature be 55 DEG C, then will be adjusted to respectively in the reaction time 24h, 48h,
72h, 96h and 120h, when as a result finding to reach 96h, reaction gradually tends to balance.Esterification yield under differential responses time conditions is such as
Shown in table 7 below：
Influence of the reaction time of table 7 to synthesis lipoic acid sterol ester
| Reaction time (h) | Esterification yield (%) |
| 24 | 21.6 |
| 48 | 42.5 |
| 72 | 55.6 |
| 96 | 71.2 |
| 120 | 68.9 |
Embodiment 8
By volume 1：In the n-hexane of 1 mixing and the mixed solution of tert-pentyl alcohol, the Candida of 60g/L is added
The molecular sieve of Rugosa, 10g/L, the phytosterol of 150mmol/L, acid alcohol mol ratio are 2.5：1, in 55 DEG C, 150rpm conditions
Lower reaction 96h.
Question response terminates, and first goes to dezymotize and molecular sieve, after removing solvent using Rotary Evaporators, with the expansion of thin-layer chromatography
Agent (petroleum ether: ethyl acetate=volume ratio 15：1) dissolving solute, then after silica gel column chromatography (mobile phase condition is petroleum ether:
Ethyl acetate=volume ratio 15：1), detected by thin layer, collect different sections of component, you can the lipoic acid plant for being purified
Sterol ester.With this understanding, product yield is 71.2%, and purity is 99.3%.
The infrared spectrum of lipoic acid sterol ester is as shown in Fig. 2 be analyzed as follows：2949cm-1For-CH3Asymmetric flexible shake
It is dynamic to absorb (νas-CH3), 2866cm-1For-CH2- symmetrical stretching vibration absorb (νs-CH2-), 1732cm-1Strong absworption peak is ester
The stretching vibration of C=O absorbs (ν C=O) in base functional group, 1462cm-1For-CH2Flexural vibrations absworption peak, 1366cm-1For-
CH3Flexural vibrations absorb (ν-CH3), 1173cm-1And 1131cm-1For the stretching vibration of C-O absorbs (ν C-O).
The mass-spectrogram of lipoic acid sterol ester is as shown in figure 4, be analyzed as follows：The relative molecular mass of stigmasterol is
412.69, the relative molecular mass of lipoic acid is 206.32, therefore the relative molecular mass of lipoic acid sterol ester is 601.Sulphur is pungent
Tamarind sterol ester is under ES+ ionization, it is understood that there may be [M+H] of lipoic acid sterol ester+[M+Na]+Molecular ion peak, in Fig. 3
601.4 is the mass signal of lipoic acid stigmasterol ester, and 624.4 is [M+Na] of lipoic acid stigmasterol ester+Mass signal.Cause
This, product is lipoic acid stigmasterol ester.
Although the present invention is disclosed as above with preferred embodiment, it is not limited to the present invention, any to be familiar with this skill
The people of art, without departing from the spirit and scope of the present invention, can do various changes with modification, therefore protection model of the invention
Enclose being defined of being defined by claims.
Claims (9)
1. a kind of method for preparing lipoic acid sterol ester, it is characterised in that be in organic phase, to be with phytosterol, lipoic acid
Substrate, lipoic acid sterol ester is synthesized with lipase as catalyst；The organic phase is with volume ratio 1：The n-hexane of 1 mixing,
Acetone, or with volume ratio 1：Tert-pentyl alcohol, the n-hexane of 1 mixing；The lipase is Novozyme 435 or Candida
Rugosa；The initial concentration of the phytosterol is 100~200mmol/L, and lipase addition is 60~80g/L, and acid alcohol rubs
You are than being (2~3)：1；Reaction temperature is 50 DEG C~60 DEG C, and the reaction time is 72~120h.
2. a kind of method for preparing lipoic acid sterol ester according to claim 1, it is characterised in that the phytosterol
Initial concentration is 100~150mmol/L, and acid alcohol mol ratio is 2.5：1.
3. a kind of method for preparing lipoic acid sterol ester according to claim 1 and 2, it is characterised in that the plant steroid
The initial concentration of alcohol is 150mmol/L.
4. a kind of method for preparing lipoic acid sterol ester according to claim 1 and 2, it is characterised in that lipase is added
It is 60g/L to measure, and lipase is the lipase from Candida Rugosa.
5. a kind of method for preparing lipoic acid sterol ester according to claim 1 or 4, it is characterised in that reaction density is
55 DEG C, the reaction time is 96h.
6. according to any a kind of described method for preparing lipoic acid sterol ester of Claims 1 to 5, it is characterised in that reactant
The molecular sieve of 0~20g/L is also added in system；The species of molecular sieve is 3A or 4A.
7. a kind of method for preparing lipoic acid sterol ester according to claim 6, it is characterised in that molecular sieve used adds
Dosage is 10g/L, and the species of molecular sieve is 4A.
8. a kind of method for preparing lipoic acid sterol ester according to claim 1, it is characterised in that by volume 1：1
In the n-hexane of mixing and the mixed solution of tert-pentyl alcohol, the lipase from Candida Rugosa of 60g/L, addition are added
The molecular sieve of 10g/L, sterol initial concentration 150mmol/L, acid alcohol mol ratio is 2.5：1, reacted under the conditions of 55 DEG C, 150rpm
96h。
9. a kind of method for preparing lipoic acid sterol ester according to claim 1, it is characterised in that also including to product
Isolate and purify, first go to dezymotize and molecular sieve, after removing solvent using Rotary Evaporators, dissolve molten with the solvent of thin-layer chromatography
Matter, then through silica gel column chromatography after, detected by thin-layer chromatography, collect different sections of component, you can the lipoic acid steroid for being purified
Alcohol ester；The silica gel column chromatography mobile phase is by volume 15：The petroleum ether of 1 mixing: ethyl acetate；The thin-layer chromatography detection
Solvent be by volume 15：The petroleum ether of 1 mixing: ethyl acetate.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112226480A (en) * | 2020-09-14 | 2021-01-15 | 河南工业大学 | Method for preparing hydrophilic phytosterol dibasic acid sugar ester in organic phase by holoenzyme method |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101845473A (en) * | 2010-06-03 | 2010-09-29 | 江南大学 | Method for effectively synthesizing phytosterol ester |
| CN103352067A (en) * | 2013-08-04 | 2013-10-16 | 中国农业科学院油料作物研究所 | Method for preparing functional grease rich in phytosterol ester and diglyceride |
-
2016
- 2016-12-29 CN CN201611242224.9A patent/CN106755254B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101845473A (en) * | 2010-06-03 | 2010-09-29 | 江南大学 | Method for effectively synthesizing phytosterol ester |
| CN103352067A (en) * | 2013-08-04 | 2013-10-16 | 中国农业科学院油料作物研究所 | Method for preparing functional grease rich in phytosterol ester and diglyceride |
Non-Patent Citations (2)
| Title |
|---|
| S.R.P. MADAWALA ET AL.: "Phytosterol and α-Lipoic Acid Conjugates: Synthesis, Free Radical Scavenging Capacity and RP-LC-MS-APCI Analysis", 《POLISH JOURNAL OF FOOD AND NUTRITION SCIENCES》 * |
| TAN: "Optimization of Enzymatic Synthesis of Phytosteryl Caprylates Using Response Surface MethodologyZhuliang", 《JOURNAL OF THE AMERICAN OIL CHEMISTS》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112226480A (en) * | 2020-09-14 | 2021-01-15 | 河南工业大学 | Method for preparing hydrophilic phytosterol dibasic acid sugar ester in organic phase by holoenzyme method |
| CN112226480B (en) * | 2020-09-14 | 2021-12-24 | 河南工业大学 | Method for preparing hydrophilic phytosterol dibasic acid sugar ester in organic phase by holoenzyme method |
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