CN101177383B - Polysiphonia urceolata bromophenol compound as well as preparation method and application thereof - Google Patents
Polysiphonia urceolata bromophenol compound as well as preparation method and application thereof Download PDFInfo
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- CN101177383B CN101177383B CN200710013730A CN200710013730A CN101177383B CN 101177383 B CN101177383 B CN 101177383B CN 200710013730 A CN200710013730 A CN 200710013730A CN 200710013730 A CN200710013730 A CN 200710013730A CN 101177383 B CN101177383 B CN 101177383B
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Abstract
The invention relates to the technical field of food additives, in particular to a bromphenol compound in polysiphonia urceolata and the preparation method and purpose. The invention is characterizedin that the bromphenol compound capable of eliminating the activity of free radical can be obtained from the polysiphonia urceolata of oceanic red alga by the method of extraction and separation, theconstitutional formula (I) or (II) is shown, wherein the R1 is H, Br, OH, OCH3 or OCH2CH3; the R2 is H, Br, OH, OCH3 or OCH2CH3; the R3is H, Br, OH, OCH3 or OCH2CH3, the preparation method is characterized in that the polysiphonia urceolata is washed by seawater; the gravels and miscellaneous algae on the surface of the polysiphonia urceolata are removed, and then the leaching, solvent distribution and repeated chromatographic separation are implemented after the polysiphonia urceolata is dried in the shade and crushed, so that a monomer compound is obtained, wherein the R1 is H, Br, OH, OCH3or OCH2CH3; the R2 is H, Br, OH, OCH3 or OCH2CH3; the R3is H, Br, OH, OCH3 or OCH2CH3. The bromphenol compound which is obtained by the preparation method of the invention has the advantages that: thebromphenol compound can be used as the food additives to delay or prevent the oxidation and metamorphosis of edible oil or oil-retaining food because of the inducement of the free radical.
Description
Technical field
The present invention relates to foodstuff additive, specifically bromine phenolic compound and its production and application in the marine red alga multitube algae.
Background technology
The oxidizing reaction that free yl induction causes can cause food particularly oleaginous food become sour rotten.Moreover, oxidizing reaction can also cause that food fades, brown stain etc., thereby has a strong impact on the quality of food, reduces Nutritive value of food.On the other hand, many oxidation productss and intermediate product that free radical causes are the carcinogenss of generally acknowledging, the organic microbial film of meeting grievous injury, protein, enzyme and cell function directly or indirectly cause the generation of numerous disease such as cancer, atherosclerosis, diabetes, nerve degenerative diseases and organism aging process etc.
One of main path that prevents food oils and oleaginous food deterioration by oxidation commonly used at present is to add antioxidant, to prevent or to delay to comprise the generation of the caused oxidizing reaction of free-radical oxidn.Wherein tertiary butyl hydroxytoluene (BHT), butylhydroxy anisole (BHA) are than common chemical synthetized oxidation preventive agent, free-radical scavengers.But along with growth in the living standard, the mankind more and more pay close attention to the safety problem of synthetized oxidation preventive agent, free-radical scavengers, discover that particularly there are certain toxicity (it is also possible carcinogenic to cause that liver enlarges) in BHT, BHA, the research of natural antioxidants, free-radical scavengers is subjected to attention more and more widely.
Summary of the invention
The purpose of this invention is to provide bromine phenolic compound and its production and application in the marine red alga multitube algae.
For achieving the above object, the technical solution used in the present invention is: the bromine phenolic compound in the multitube algae, structural formula be as (I) or (II),
(I) (II)
Wherein: R
1For: H, Br, OH, OCH
3Or OCH
2CH
3, R
2Be H, Br, OH, OCH
3Or OCH
2CH
3, R
3Be H, Br, OH, OCH
3Or OCH
2CH
3
The preparation method comprises the steps:
1) rinse, dry in the shade, be crushed to marine red alga multitube algae well the 60-80 order, with organic solution leaching 2-5 time, united extraction liquid concentrates, and obtains crude extract then;
2) water of getting 2-3 times of volume of gained crude extract in the step 1) adds in the crude extract of step 1), and extract each 2-4 time respectively with described adding volume of water 2-3 sherwood oil, ethyl acetate, propyl carbinol doubly successively, extract concentrate separately corresponding extract, standby;
3) get step 2) in ethyl acetate extract carry out silica gel column chromatography, carry out gradient elution with organic solvent, collect elutriant, elutriant detects through thin-layer chromatography;
Described organic solvent is 100: 0-0: the chloroform-methanol of 100 gradients or ethyl acetate-methyl alcohol;
4) with in the step 3) with chloroform-methanol or ethyl acetate-methyl alcohol volume ratio 35-40: the component under 1 gradient elution is carried out silica gel and dextrane gel column chromatography, after collecting elutriant and concentrating target compound (I);
Or with in the step 3) with chloroform-methanol or ethyl acetate-methyl alcohol volume ratio 25-30: the component under 1 gradient elution is carried out silica gel and dextrane gel column chromatography, after collecting elutriant and concentrating target compound (II).
Organic solution extracting solution in the step 1) can be ethanol or the methyl alcohol of concentration at 50-100%.
The used elutriant of silica gel column chromatography can be the sherwood oil-acetone sherwood oil-acetone or the petroleum ether-ethyl acetate of 40: 60 to 0: 100 gradients in the step 4); The used elutriant of dextrane gel column chromatography can be methyl alcohol or chloroform-methanol.
Application of compound, described compound is as delaying, prevent food oils deterioration by oxidation or the oleaginous food additive that free yl induction causes.
The present invention has the following advantages:
The compound that the present invention relates to is new bromine phenolic compound, belongs to the small molecules natural organic-compound, prepares easily; The bromine phenolic compound that the present invention relates to has significant DPPH freedom (α, α-diphenyl-β-picrylhydrazyl, that is, hexichol is for the bitter taste free acyl radical) activity, can be used as foodstuff additive and delay or prevent the deterioration by oxidation that food oils and oleaginous food cause because of free yl induction.
The marine red alga multitube algae that the present invention relates to (Polysiphonia urceolata Grev.) belongs to rhodophyta, Rhodomelaceae, Polysiphonia marine alga, mainly is distributed in Huanghai Sea marine site in China.Bromine phenols natural compounds (I), (II) of the present invention by the multitube algae is obtained through extraction, separation, the experiment proved that, these compounds have significant DPPH free radical scavenging activity, its action intensity is apparently higher than synthetic BHT under identical concentration conditions, can be widely used in food oils or the oleaginous food, instead of chemical synthetized oxidation preventive agent, free-radical scavengers, the generation of the oxidizing reaction that prevents or delay to cause by free radical, thereby extend the shelf life, improve the quality of products.
Embodiment:
Below in conjunction with embodiment the present invention is further elaborated.
Embodiment 1
The preparation method of bromine phenolic compound:
Gather fresh multitube algae and clean through seawater, remove the grit and the assorted algae of surface attachment, shady and cool place airing is standby.Get the sample 6.1Kg behind the airing, be crushed to that the ethanol with 8.5 liter 95% at room temperature extracts three times behind the 60-80 order, each three days, merge ethanol extract, at 40 ℃ of left and right sides concentrating under reduced pressure of temperature, reclaim ethanol, obtain the ethanol crude extract.The distilled water that adds 2 times of gained crude extract volumes in the crude extract makes it to be suspended in the water, sherwood oil, ethyl acetate, propyl carbinol with 2 times of volumes of the distilled water of above-mentioned suspendible crude extract extracts each respectively three times successively, concentrates the back respectively and obtains corresponding sherwood oil, ethyl acetate, n-butanol extract.Ethyl acetate extract (60 gram) is carried out silica gel column chromatography, with chloroform-methanol with 100: 0,90: 1,85: 1,70: 1,50: 1,40: 1,30: 1,20: 1,10: 1,5: 1,3: 1,1: 1 to 0: 100 gradient is carried out wash-out, collect elutriant respectively, use thin-layer chromatography (TLC) to detect (using iron trichloride) again as developer, judge, merge identical or similar portions according to the Rf value, obtain 36 components.With the 18th component, its Rf=0.3-0.4 (200 milligrams) promptly carries out dextrane gel SephadexLH-20 column chromatography again with the component under 40: 1 gradient elutions of chloroform-methanol, with 1: 1 chloroform-methanol wash-out, elutriant obtained pure compound A (3.0 milligrams) through concentrating under reduced pressure, through Spectrum Analysis, the structure of compd A is defined as 7-bromo-9,10-dihydro phenanthrene-2,3,5,6-tetrol, English 7-bromo-9 by name, 10-dihydrophenanthrene-2,3,5,6-tetraol, i.e. R in the formula (worker)
1, R
2, R
3The compound of representative when being H simultaneously; With the 20th component (2 gram), promptly carry out silica gel column chromatography and dextrane gel Sephadex LH-20 column chromatography for separation again with the component under 30: 1 gradient elutions of chloroform-methanol, carry out wash-out with gradient at sherwood oil-acetone of 40: 60 to 0: 100 during silica gel column chromatography, dextrane gel Sephadex LH-20 column chromatography obtains pure compound B (2.0 milligrams) with the methanol-eluted fractions of 100% concentration, elutriant through concentrating under reduced pressure, through Spectrum Analysis, the structure of compd B is defined as 4,6-two bromo-9,10-dihydro phenanthrene-2,3,5,7-tetrol, English by name 4,6-dibromo-9,10-dihydrophenanthrene-2,3,5,7-tetraol, i.e. R in the formula (II)
1, R
2, R
3The compound of representative when being H simultaneously.The structural formula of compd A, B is as follows.
The compd A compd B
Compd A, B have following physics and chemistry and spectral characteristic:
Compd A: yellow powder shape solid, fusing point 147-149 ℃; Proton nmr spectra (
1H NMR, acetone-d
6, 500MHz) δ (acetone-d
6, 500MHz) 6.71 (1H, s, H-1), 8.01 (1H, s, H-4), 6.88 (1H, s, H-8), 2.63 (2H, m, H-9), 2.58 (2H, m, H-10); Carbon-13 nmr spectra (
13C NMR, acetone-d
6, 125MHz) δ 131.3 (s, C-1a), 115.4 (d, C-1), 144.9 (s, C-2), 143.6 (s, C-3), 116.9 (d, C-4), 125.2 (s, C-4a), 122.5 (s, C-5a), 144.7 (s, C-5), 141.9 (s, C-6), 107.8 (s, C-7), 122.4 (d, C-8), 133.0 (s, C-8a), 30.6 (t, C-9), 30.0 (t, C-10); Low Resolution Mass Spectra EIMSm/z (%) 324/322[M]
+(90,100), 244 (16), 242 (37), 226 (29), 225 (15), 140 (10), 139 (25), 115 (11), 113 (15), 98 (30), 89 (8), 84 (16), 70 (13), 69 (10); High resolution mass spectrum HRESIMSm/z 322.9915[M+H]
+(calcd for C
14H
12 79BrO
4, 322.9919).
Compd B: yellow powder shape solid, fusing point 132-134 ℃; Proton nmr spectra (
1H NMR, acetone-d
6, 500MHz) δ (acetone-d
6, 500MHz) 6.79 (1H, s, H-1), 6.95 (1H, s, H-8), 2.42, (2H, d, J=15.9, H-9), 2.61 (2H, m, H-10); Carbon-13 nmr spectra (
13C NMR, acetone-d
6,125MHz) δ 113.4 (d, C-1), 144.3 (s, C-2), 141,7 (s, C-2), 110.8 (s, C-4), 125.4 (s, C-4a), 121.8 (s, C-5a), 142.8 (s, C-5), 107,3 (s, C-6), 142.0 (s, C-7), 121.8 (d, C-8), 131.3 (s, C-1a), 133.0 (s, C-8a), 30.0 (t, C-9), 31.0 (t, C-10); Low Resolution Mass Spectra EIMS m/z (%) 404/402/400[M]
+(23/45/21), 324 (40), 323 (49), 322 (48), 321 (47), 305 (96), 303 (100), 242 (36), 214 (15), 213 (18), 139 (17); High resolution mass spectrum HRESIMSm/z424.8825[M+Na]
+(calcd for C
14H
10 79Br
81BrNaO
4, 424.8823).
Embodiment 2
Difference from Example 1 is:
With the multitube algae of drying and crushing with the extraction using alcohol of concentration 80% 4 times, each three days, united extraction liquid, concentrating under reduced pressure obtains crude extract under the room temperature, ethanol reclaims simultaneously.Crude extract is suspended in the water of 3 times of crude extract volumes, sherwood oil, ethyl acetate, propyl carbinol with 2 times of volumes of the distilled water of above-mentioned suspendible crude extract respectively extracts three times successively, concentrates the back respectively and obtains corresponding sherwood oil, ethyl acetate, n-butanol extract.Ethyl acetate extract is carried out silicagel column (220 grams, the 200-300 order) chromatography, ethyl acetate-the methyl alcohol that with gradient is 100: 0 to 0: 100 gradient carries out gradient elution, collect elutriant respectively, detect (using iron trichloride) with thin-layer chromatography (TLC), judge, merge identical or similar portions according to the Rf value as developer; Will be with the elutriant of ethyl acetate-methyl alcohol under 40: 1 to 30: 1 gradient elutions, Rf=0.25-0.4 wherein, carry out silica gel column chromatography again and separate and dextrane gel Sephadex LH-20 column chromatography, silica gel column chromatography employing gradient is carried out wash-out at 20: 80 to 0: 100 petroleum ether-ethyl acetate; The used eluent of dextrane gel column chromatography is that gradient is that 50: 50 chloroform-methanol carries out wash-out, obtains pure compound behind the elutriant concentrating under reduced pressure, and structural formula is as (I) or (II),
(I) (II)
Wherein: R
1For: H, Br, OH, OCH
3Or OCH
2CH
3, R
2Be H, Br, OH, OCH
3Or OCH
2CH
3, R
3Be H, Br, OH, OCH
3Or OCH
2CH
3
For example: pure compound C and Compound D, through Spectrum Analysis, the structure of Compound C is defined as 4,7-two bromo-9,10-dihydro phenanthrene-2,3,5,6, the 8-amylalcohol, English is called 4,7-dibromo-9,10-dihydrophenanthrene-2,3,5,6,8-pentaol, i.e. R in the formula (I)
1Be H, R
2Be Br, R
3The compound of representative during for OH; The structure of compd B is defined as 1,4,6-three bromo-9, and 10-dihydro phenanthrene-2,3,5,7, the 8-amylalcohol, English is called 1,4,6-tribromo-9,10-dihydrophenanthrene-2,3,5,7,8-pentaol, i.e. R in the formula (II)
1Be Br, R
2The compound of representative during for OH.The structural formula of Compound C, D is as follows.
The Compound C Compound D
Above general formula compound of while all can further be derived by compd A and B and be formed.
Embodiment 3
The experiment of DPPH free radical scavenging activity:
DPPH is a kind of stable free radical, is purple in organic solvent, and strong absorption is arranged near 517nm, and behind the adding antioxidant, a part of free radical is eliminated, and makes to absorb and weakens, and can estimate the power of its anti-oxidant activity, free radical scavenging activity whereby.This method is easy and simple to handle, favorable reproducibility.
Experimental technique:
In 2mL embodiment 1, add in the gained sample 2mL DPPH (methanol solution, 0.16mmol/L) mix after, after 50min is placed in the room temperature dark place, in 517nm place its absorbance A of mensuration
Sample
In 2mL embodiment 1, add the 2mL methanol solution in the gained sample and measure its absorbance A in the 517nm place
SamplebankAdd 2mL methyl alcohol chloroform mixed solvent among the 2mLDPPH and measure its absorbance A in the 517nm place
ControlAdd 2mL methyl alcohol chloroform mixed solvent in the 2mL methyl alcohol and measure its absorbance A in the 517nm place
Blank
The calculating of free radical scavenging activity:
Clearance rate %=100-(A
Sample-A
Sample blank) * 100/ (A
Control-A
Blank).The sample that embodiment 1 obtains is tested respectively under 0.1 μ g/mL, 0.25 μ g/mL, 1.0 μ g/mL, 2.5 μ g/mL, 5.0 μ g/mL, 10.0 μ g/mL, 25.0 μ g/mL different concns, each concentration replicate(determination) three times, averaging is the sample clearance rate, and calculates IC
50Value.All tests all are that standard substance are as positive control with BHT.
Experimental result: referring to table 1, data show the bromine phenolic compound of above-mentioned acquisition have significant DPPH remove active, at the activity intensity of lower concentration bromine phenolic compound under the high density all apparently higher than positive control BHT.In addition, experiment shows, the IC of BHT
50Be 83.3 μ M, and the IC of bromine phenolic compound A, B
50Be respectively 6.78 and 6.13 μ M, 1/12nd or 1/13rd of only positive contrast BHT, show compd A, B free radical scavenging activity be significantly higher than positive control BHT.
Table 1
Embodiment 4
The application of bromine phenolic compound in food oils are anti-oxidant:
Get 1 kilogram of food oils, the weight ratio according to 0.02% adds bromine phenolic compound A or the B that obtains among the foregoing description 1-2, mixes, and makes the food oils of Green Tea Extract oxidation.Compare with the food oils that do not contain bromine phenolic compound, its preservation period of food oils that contains bromine phenolic compound be the former 2-3 doubly more than.
Bromine phenolic compound involved in the present invention can be applicable in any food oils, to prevent or to delay the deterioration by oxidation that free radical causes, extends the shelf life.
Claims (3)
1. the bromine phenolic compound in the multitube algae is characterized in that: structural formula is as (I) or (II),
Wherein: R
1For: H, R
2Be H, R
3Be H.
2. the preparation method of the described sea weed bromophenol compound of claim 1 is characterized in that, comprises the steps:
1) rinse, dry in the shade, be crushed to marine red alga multitube algae well the 60-80 order, with organic solution leaching 2-5 time, united extraction liquid concentrates, and obtains crude extract then; Described organic solution is ethanol or the methyl alcohol of concentration at 50-100%;
2) water of getting 2-3 times of volume of gained crude extract in the step 1) adds in the crude extract of step 1), and extract each 2-4 time respectively with described adding volume of water 2-3 sherwood oil, ethyl acetate, propyl carbinol doubly successively, extract concentrate separately corresponding extract, standby;
3) get step 2) in ethyl acetate extract carry out silica gel column chromatography, carry out gradient elution with organic solvent, collect elutriant, elutriant detects through thin-layer chromatography;
Described organic solvent is 100: 0-0: the chloroform-methanol of 100 gradients or ethyl acetate-methyl alcohol;
4) with in the step 3) with chloroform-methanol or ethyl acetate-methyl alcohol volume ratio 35-40: the component under 1 gradient elution is carried out silica gel and dextrane gel column chromatography, after collecting elutriant and concentrating target compound (I);
Or with in the step 3) with chloroform-methanol or ethyl acetate-methyl alcohol volume ratio 25-30: the component under 1 gradient elution is carried out silica gel and dextrane gel column chromatography, after collecting elutriant and concentrating target compound (II); The used elutriant of described silica gel column chromatography is sherwood oil-acetone or petroleum ether-ethyl acetate; The used elutriant of dextrane gel column chromatography is methyl alcohol or chloroform-methanol.
3. the application of the described sea weed bromophenol compound of claim 1 is characterized in that: described compound is used to delay or prevent food oils or the oleaginous food deterioration by oxidation that free yl induction causes as foodstuff additive.
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|---|---|---|---|
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|---|---|---|---|
| CN200710013730A CN101177383B (en) | 2007-02-17 | 2007-02-17 | Polysiphonia urceolata bromophenol compound as well as preparation method and application thereof |
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|---|---|
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| CN101177383B true CN101177383B (en) | 2010-05-19 |
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|---|---|---|---|
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Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101643442B (en) * | 2008-08-07 | 2011-05-18 | 中国科学院海洋研究所 | Seaweed bromphenol urea compounds, preparation method and application thereof |
| DE102009022309A1 (en) * | 2009-05-22 | 2010-11-25 | Merck Patent Gmbh | liquid-crystal display |
| WO2016201559A1 (en) * | 2015-06-16 | 2016-12-22 | Oceans Ltd. | Seaweed extracts with anti-cancer activity |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1202334A (en) * | 1998-05-28 | 1998-12-23 | 中国科学院海洋研究所 | Preparation of seeweed polyphenol antioxidation agent and its applying method |
| CN1287158A (en) * | 2000-10-09 | 2001-03-14 | 汕头大学 | Natural composition used as fish oil antioxidant |
-
2007
- 2007-02-17 CN CN200710013730A patent/CN101177383B/en not_active Expired - Fee Related
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1202334A (en) * | 1998-05-28 | 1998-12-23 | 中国科学院海洋研究所 | Preparation of seeweed polyphenol antioxidation agent and its applying method |
| CN1287158A (en) * | 2000-10-09 | 2001-03-14 | 汕头大学 | Natural composition used as fish oil antioxidant |
Non-Patent Citations (2)
| Title |
|---|
| 魏安池等.天然抗氧化剂研究概况.郑州工程学院学报Vol.21 No.4.2000,Vol.21(No.4),62-66. * |
| 魏安池等.天然抗氧化剂研究概况.郑州工程学院学报Vol.21No.4.2000 Vol.21(No.4) |
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