CN108047167A - A kind of method for preparing fucoxanthin cis-isomer - Google Patents
A kind of method for preparing fucoxanthin cis-isomer Download PDFInfo
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- CN108047167A CN108047167A CN201711432955.4A CN201711432955A CN108047167A CN 108047167 A CN108047167 A CN 108047167A CN 201711432955 A CN201711432955 A CN 201711432955A CN 108047167 A CN108047167 A CN 108047167A
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- C07—ORGANIC CHEMISTRY
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- C07D303/00—Compounds containing three-membered rings having one oxygen atom as the only ring hetero atom
- C07D303/02—Compounds containing oxirane rings
- C07D303/12—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms
- C07D303/32—Compounds containing oxirane rings with hydrocarbon radicals, substituted by singly or doubly bound oxygen atoms by aldehydo- or ketonic radicals
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Abstract
The present invention provides a kind of methods for preparing fucoxanthin cis-isomer.Present invention firstly discovers that the fucoxanthin cis-trans-isomer mixture being mainly made of transisomer is dissolved in ethyl acetate solvent, in solid catalyst I2‑TiO2Under the action of nano particle, pass through catalyst amount, temperature, reaction time, higher 9 cis of transisomer of content can be obtained, 13 cis and 13 ' cis fucoxanthin, the cis-trans-isomer fucoxanthin mixture can obtain mainly containing the fucoxanthin of cis-structure by preparation HPLC.Addition solid catalyst is only needed in this method preparation process, solid catalyst removal is convenient, repeats using repeatedly, and the reaction time is short, fucoxanthin less degradation, and cis fucoxanthin enantiomeric purity obtained is high.Cis fucoxanthin isomery body method is simple, at low cost made from this method, can be applied to the further research of bioactivity.
Description
Technical field
The present invention relates to a kind of methods for preparing fucoxanthin cis-isomer.
Background technology
Fucoxanthin (Fucoxanthin, FX) is diatom, chrysophyceae, yellowish green algae and brown algae photosynthesis Photosystem I I
Important pigment, is one of nature content carotenoid the abundantest, and content has accounted for carotenoid nature total content
10% or so.It is the there are allene key, 5,6- epoxy groups, conjugation carbonyl and acetyl group in fucoxanthin molecular structure
One finds the carotenoid with allene structure in marine brown.The molecular structure of fucoxanthin uniqueness is that its is a variety of
The chemical fundamentals of bioactivity.Fucoxanthin molecule contains hydroxyl, ester bond and multiple unsaturation α, β-unsaturated bond, can conduct
With many important albumen Mike's addition reaction occurs for acceptor, so as to improve the metabolic cycles of organism, plays its bioactivity
Function.Substantial amounts of cell culture and zoopery show fucoxanthin in anti-oxidant, anti-inflammatory, anticancer, antithrombotic, anti-malarial, suppression
System is fat and diabetes and liver, brain, bone, skin, eyes and cardiovascular system protective effect in terms of have it is great
Potential medical value.Compared with current similar final drug beta carotene and astaxanthin, fucoxanthin inhibit it is fat, into
There is more prominent performance in ripe T cell increment and sea in terms of strangling cancer cell development.Biological toxicological experiment shows to take rock simultaneously
Phycoxanthine has the characteristics that toxic side effect is small, does not influence lipid metaboli Xun Huan, thus fucoxanthin is that one kind has very big potential medicine
With the marine active natural products of value and economic value.
There is conjugated double bond, there are mainly four types of cis-trans-isomer (cis-trans isomers) (figures in fucoxanthin molecule
1)：All-trans Fx, 9'-cis Fx, 13-cis Fx and 13'-cis Fx.All trans isomer is sterically hindered small, fresh
Fucoxanthin almost all exists with all trans isomer in brown alga.At present, traditional fucoxanthin extracting method mainly has molten
Agent extraction, supercritical CO2Extraction, ultrasonic wave assisted extraction method etc., the fucoxanthin being prepared with these methods is main
Exist in the form of transisomer.With the further investigation to fucoxanthin activity, scientific research personnel has found different isomer pair
Activity has a great impact.Nakazawa et al et al. researchs point out that 13-cis Fx, 13'-cis Fx are to a variety of cancer cells
The inhibitory action of HL-60, Caco-2, PC-3 are significantly higher than all-trans, 9'-cis.Moreover, 13'-cis Fx are to cancer cell
The inhibitory activity of HL-60 is most strong, is significantly higher than 13-cis and other isomers.In addition, Zhang et al. et al. researchs are found
13-cis Fx and 13'-cis Fx also show stronger free radical scavenging activity.These researchs show the 13- of fucoxanthin
The all trans isomer of cis, 13'-cis ratios of the isomers naturally occurring has better exploitation prospect.Therefore, searching will be trans
Fucoxanthin isomers is converted into the method for cis fucoxanthin isomers for preferably utilizing the bioactivity of fucoxanthin
It is significant.
The configuration conversion of cis-trans-isomer is a chemical dynamics equilibrium process, this process generally comprise photoisomerization,
Thermotropic isomerization and isoversion.But there is presently no a kind of sides of suitable fucoxanthin cis-trans-isomer Efficient Conversion
Method.Miyashita etc. obtains 13/13'-cis isomer mixtures by low temperature dark treatment alltrans fucoxanthin, accounts for rock algae
The ratio of flavine total amount is 27% (w/w).But this method needs the reaction time up to 2 months, and conversion ratio is relatively low.Be not suitable for
Industrial production.Since cis-isomer has preferably activity and development prospect, explore and establish efficiently, quickly by alltrans rock algae
The method that flavine is converted into single cis-isomer not only has important learning value, to further promoting China superior resources sea
The food medicine value of band has important impetus.I is utilized present invention firstly discloses a kind of2-TiO2Solid catalyst is efficiently fast
Speed realizes the method that trans fucoxanthin is converted to cis fucoxanthin isomers, and this method is simple, the reaction time is short, rock algae is yellow
Plain less degradation, cis fucoxanthin enantiomeric purity at low cost, obtained are high, can be applied to largely prepare, for cis rock algae
Application of the flavine in drug, health products is significant.
The content of the invention
In view of the deficiencies of the prior art, the present invention provides a kind of quick methods for preparing fucoxanthin cis-isomer.
To achieve the above object, the technical solution adopted by the present invention is：First by the rock based on a certain amount of anti-configuration
Phycoxanthine is dissolved in ethyl acetate, is made into certain density solution.Then carry out under certain condition in the presence of a catalyst
Reaction solution finally is isolated and purified to obtain the rock algae Huang based on cis-isomer by the conversion of cis-trans-isomer with HPLC
Element.
Wherein, which is characterized in that after catalytic reaction, the fucoxanthin cis-trans-isomer cis-isomer 9-
The content of cis, 13-cis and 13 '-cis add up to 40~70%；HPLC after purification, obtained fucoxanthin cis-isomer 9-
Cis, 13-cis and 13 '-cis contents add up to 70-95%.
Wherein, the concentration of the ethyl acetate solution of the fucoxanthin based on the anti-configuration is 0.1-1mg/mL.
Wherein, the catalyst is I2-TiO2Catalyst, I2-TiO2The weight ratio of catalyst and fucoxanthin is 1:
10—1:2.Catalyst I2-TiO2It is prepared by the following method：Solution A：3--8mL butyl titanates and 0.6-1.5mL second
Acid mixing；Solution B：160-240mg potassium iodide and 7-12mg polyvinylpyrrolidones (PVP) are dissolved in 50-70mL aqueous solutions；
Solution A will be added drop-wise in solution B under stirring, be stirred at room temperature reaction 3-5 it is small when after, 100 degrees Celsius reaction 24 it is small when, then
Room temperature cools down；Filtering is collected precipitation, be dry, pulverize, and both obtains I2-TiO2Catalyst.
Wherein, the reaction condition is：Reaction solution is put into water-bath, is protected from light, is passed through N2Protection, controlling reaction temperature
50-80 DEG C, reaction time 1-5h.
Wherein, the HPLC purification conditions are：Chromatographic column：ODS-C18 (5-10m, 250cm*4.6-20mm)；Stream
Dynamic phase：Methanol：Acetonitrile=50-70:50-30=v/v；Flow velocity：3-8.0mL/min；Detector：PDA 450nm.
Wherein, the master will by the fucoxanthin that transisomer forms from kelp, sargassum thunbergii, sargassum, yellow tang,
It is prepared in the common brown alga of the Phaeophytas brown alga mesh such as bulk kelp and diatom.
Present invention firstly discloses a kind of method for efficiently quickly preparing cis fucoxanthin isomers, prepared by this method
Only solid catalyst I need to be added in journey2-TiO2, solid catalyst removal is convenient, repeats using repeatedly, the reaction time is short, rock
Phycoxanthine less degradation, cis fucoxanthin enantiomeric purity obtained are high.Cis fucoxanthin isomers made from this method
Method is simple, at low cost, can be applied to largely prepare, and has for application of the cis fucoxanthin in drug, health products important
Meaning.
Description of the drawings
The stereoisomer of Fig. 1 fucoxanthin.
In Fig. 2 kelps fucoxanthin crude extract (left side) and carry out cis-trans-isomer conversion reaction after fucoxanthin (right side) group
Into analysis.
In Fig. 3 diatoms fucoxanthin crude extract (left side) and carry out cis-trans-isomer conversion reaction after fucoxanthin (right side) group
Into analysis.
Fucoxanthin crude extract (left side) and fucoxanthin (right side) after cis-trans-isomer conversion reaction is carried out in Fig. 4 sargassum thunbergiis
Composition analysis.
The preparation of cis fucoxanthin in Fig. 5 kelps.
Specific embodiment
With reference to specific embodiment, the present invention is further explained.It is to be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after present disclosure has been read, those skilled in the art can
To be made various changes or modifications to the present invention, such equivalent forms equally fall within limited range of the present invention.
Embodiment 1, transformation of the trans fucoxanthin isomers prepared in kelp to cis fucoxanthin isomers
1000g kelp algae powder is taken, adds in 1L ethanol solutions, 50 are protected from light extraction 2 times, each 2h.Merge extracting solution twice, use
Methanol phase is finally collected in petroleum ether extraction, again with methanol extraction, and low-temperature dark drying obtains fucoxanthin crude product 0.4g, leads
It will be by trans fucoxanthin structure composition (Fig. 2).The fucoxanthin solution 500mL ethyl acetate that will be obtained adds in embodiment 5 and makes
Standby I2-TiO2Reaction solution is put into water-bath by 30mg, is protected from light, and is passed through N2Protection, 60 DEG C of controlling reaction temperature, the reaction time is
2h.After reaction, filter, collect filtrate, concentration, drying.Dried fucoxanthin sample is dissolved in methanol, uses HPLC
Analysis, analysis result are shown in Fig. 2,13-cis Fx, 70% that 13'-cis and 9-cis mass contents are fucoxanthin.
Embodiment 2, transformation of the trans fucoxanthin isomers prepared in diatom to cis fucoxanthin isomers
1000g silicon algae powders are taken, add in 1L ethanol solutions, 50 are protected from light extraction 2 times, each 2h.Merge extracting solution twice, use
Methanol phase is finally collected in petroleum ether extraction, again with methanol extraction, and low-temperature dark drying obtains fucoxanthin crude product 0.5g.Will
The fucoxanthin solution 600mL ethyl acetate arrived adds in I prepared by embodiment 52-TiO2Reaction solution is put into water-bath by 15mg
In, it is protected from light, is passed through N2Protection, 50 DEG C of controlling reaction temperature, reaction time 1h.After reaction, filter, collect filtrate, it is dense
Contracting, drying.Dried fucoxanthin sample is dissolved in methanol, is analyzed with HPLC, analysis result is shown in Fig. 3,13-cis Fx,
13'-cis and 9-cis mass contents are the 40% of fucoxanthin.
Embodiment 3, the transformation of trans fucoxanthin isomers prepared by sargassum thunbergii algae to cis fucoxanthin isomers
The fresh sargassum thunbergiis of 1000g are taken, are cleaned, grinding adds in 1L ethanol solutions, and 50 are protected from light extraction 2 times, each 2h.Merge
Extracting solution twice, with petroleum ether extraction, methanol phase is finally collected in again with methanol extraction, and low-temperature dark drying obtains fucoxanthin
Crude product 0.4g.The fucoxanthin solution 500mL ethyl acetate that will be obtained adds in I prepared by embodiment 52-TiO240mg, will be anti-
Liquid is answered to be put into water-bath, is protected from light, is passed through N2Protection, 80 DEG C of controlling reaction temperature, reaction time 5h.After reaction, filter,
Collect filtrate, concentration, drying.It is analyzed with HPLC, analysis result is shown in Fig. 4,13-cis Fx, 13'-cis and 9-cis mass contents
For the 80% of fucoxanthin.
Embodiment 4, the purifying of cis fucoxanthin isomers in diatom
Cis-trans-isomer conversion in embodiment 2 is terminated dried fucoxanthin sample 0.1g to be dissolved in methanol, is used
HPLC is isolated and purified, and specific HPLC purification conditions are：Chromatographic column：Shim-packPREP-ODS (H) Kit (5 μm, 250*
2.6cm)；Mobile phase：Methanol：Acetonitrile=70:30=v/v；Flow velocity：5.0mL/min；30 DEG C of temperature, Detection wavelength 450nm.It is pure
Fucoxanthin sample after change is shown in Fig. 5, and the quality purity of 13-cis Fx, 13'-cis and 9-cis are 95%.
Embodiment 5, solid catalyst I2-TiO2Preparation
Catalyst I2-TiO2It is prepared by the following method：Solution A：5mL butyl titanates and the mixing of 1mL acetic acid；It is molten
Liquid B：242.9mg potassium iodide and 10mg polyvinylpyrrolidones (PVP) are dissolved in 60mL aqueous solutions.By under stirring by solution A
Be added drop-wise in solution B, be stirred at room temperature reaction 4 it is small when after, 100 degree reaction 24 it is small when, then room temperature cooling.Filtering, it is heavy to collect
It forms sediment, dry, pulverize, both obtain I2-TiO2Catalyst.
Present invention firstly discloses a kind of method for efficiently quickly preparing cis fucoxanthin isomers, prepared by this method
New chemical reagent need not be added in journey, solid catalyst removal is convenient, repeats using repeatedly, the reaction time is short, rock algae
Flavine less degradation, cis fucoxanthin enantiomeric purity obtained are high.Cis fucoxanthin isomers side made from this method
Method is simple, at low cost, can be applied to the further research of bioactivity.
It is above the description to the embodiment of the present invention, by the foregoing description of the disclosed embodiments, makes this field special
Industry technical staff can realize or use the present invention.A variety of modifications of these embodiments carry out those skilled in the art
It says and will be apparent, the general principles defined herein can not depart from the situation of the spirit or scope of the present invention
Under, it realizes in other embodiments.Therefore, the present invention is not intended to be limited to the embodiments shown herein, but to accord with
Close the most wide scope consistent with the principles and novel features disclosed herein.
Claims (7)
- A kind of 1. method for preparing fucoxanthin cis-isomer, which is characterized in that rock algae of this method based on anti-configuration Flavine is raw material, follows these steps to carry out：(1) fucoxanthin based on anti-configuration is dissolved in ethyl acetate, is made into the solution that concentration is 0.1-1mg/mL；(2) I is added in the fucoxanthin ethyl acetate solution described in (1)2-TiO2Catalyst, I2-TiO2Catalyst is yellow with rock algae The weight ratio of element is 1:10—1:2；Reaction solution is protected from light, is passed through N2Protection, 50-80 DEG C of controlling reaction temperature, the reaction time is 1-5h；(3) after reaction, filter, filtrate is isolated and purified with preparation HPLC, you can obtain mainly containing cis different The fucoxanthin of structure body.
- 2. according to the method described in claim 1, it is characterized in that, fucoxanthin in fucoxanthin raw material based on anti-configuration Cis-trans-isomer transisomer mass content adds up to 85~98%.
- 3. according to the method described in claim 1, it is characterized in that, (2) step after reaction, the fucoxanthin is along anti- The content of isomer cis isomers 9-cis, 13-cis and 13 '-cis add up to 40~70%.
- 4. the according to the method described in claim 1, it is characterized in that, fucoxanthin syn-isomerism that (3) step after purification, obtains Body 9-cis, 13-cis and 13 '-cis content adds up to 70-95%.
- 5. the according to the method described in claim 1, it is characterized in that, fucoxanthin being mainly made of transisomer used From one kind in the common brown alga of the Phaeophytas brown alga mesh such as kelp, sargassum thunbergii, sargassum, yellow tang, bulk kelp and diatom or two kinds with The upper fucoxanthin prepared for raw material.
- 6. the according to the method described in claim 1, it is characterized in that, catalyst I added in during the reaction2-TiO2It is to pass through Prepared by following methods：Solution A：3--8mL butyl titanates and the mixing of 0.6-1.5mL acetic acid；Solution B：160-240mg potassium iodide and 7-12mg polyvinylpyrrolidones (PVP) are dissolved in 50-70mL aqueous solutions；Solution A will be added drop-wise in solution B under stirring, be stirred at room temperature reaction 3-5 it is small when after, 100 degrees Celsius reaction 24 it is small when, Then room temperature cools down；Filtering is collected precipitation, be dry, pulverize, and both obtains I2-TiO2Catalyst.
- 7. according to the method described in claim 1, it is characterized in that, preparation HPLC purification condition is used after reaction It is：Chromatographic column：ODS-C18 (5-10m, 250cm*4.6-20mm)；Mobile phase：Methanol：Acetonitrile=50-70:50-30=v/v；Stream Speed：3-8.0mL/min；Detector：PDA 450nm.
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| CN106478553A (en) * | 2015-08-27 | 2017-03-08 | 中国海洋大学 | High-purity fucoxanthin technology of preparing |
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| WO2007094430A1 (en) * | 2006-02-16 | 2007-08-23 | National University Corporation Hokkaido University | Cancer inhibitor, cancer inhibitor-containing product and process for producing cancer inhibitor |
| CN104475134A (en) * | 2014-12-05 | 2015-04-01 | 江南大学 | Preparation method of iodine-doped titanium dioxide nano catalyst and use of catalyst in heterogeneous catalysis of configuration inversion of trans-carotenoids |
| US20160158736A1 (en) * | 2014-12-05 | 2016-06-09 | Jiangnan University | Method for preparing iodine-doped tio2 nano-catalyst and use thereof in heterogeneously catalyzing configuration transformation of trans-carotenoids |
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Application publication date: 20180518 |