CN104592798A - Application of aurantiamide acetate in preventing and removing marine fouling organisms - Google Patents
Application of aurantiamide acetate in preventing and removing marine fouling organisms Download PDFInfo
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- CN104592798A CN104592798A CN201410833236.3A CN201410833236A CN104592798A CN 104592798 A CN104592798 A CN 104592798A CN 201410833236 A CN201410833236 A CN 201410833236A CN 104592798 A CN104592798 A CN 104592798A
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- acetic acid
- acid amides
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1612—Non-macromolecular compounds
- C09D5/1625—Non-macromolecular compounds organic
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
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- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract
The invention belongs to the biotechnical field and particularly discloses an application of aurantiamide acetate in preventing and removing marine fouling organisms. According to the invention, aurantiamide acetate can effectively inhibit a setting and metamorphosing process of various larval marine fouling organisms and low dosage aurantiamide acetate has a remarkable inhibiting effect on attachment of marine organisms, and moreover, aurantiamide acetate inhibiting attachment of the marine fouling organisms does not pollute a water environment and is not enriched in living bodies due to transport through food chain. Therefore, aurantiamide acetate is a natural and environment-friendly compound which has good biofouling activity and has a good application prospect in preventing and removing marine fouling organisms for various marine facilities.
Description
Technical field
The invention belongs to biological technical field, particularly, relate to the application of acetic acid orange acid amides in preventing and removing marine fouling organisms.
Background technology
Marine fouling organism refers to set or perches the different kind organism at boats and ships and maritime facilities underwater sites, fouling organism is divided into two life stages usually, one is the life stage that swims, and namely deviates from egg membrane from larva and is developed to explore the stage that body surface prepares settlement and metamorphosis off and on; Two is set or epiphytism stage, and namely larva chooses colonization sites, in adherance surface attachment, the abnormal stage forming the young.The harm that marine fouling organism produces mainly comprises: increase resistance, reduces the speed of a ship or plane, increases fuel consumption and CO
2discharge; Blocking seawater piping systems, changes Process of Metallic Corrosion, causes local corrosion or pitting corrosion; Increase dynamic load effect, cause the drift of facility, unbalance even causing topple; Fight for adherance and bait with cultivation object (as shellfish), hinder it to grow, reduce the quality of product.
Antifouling paint is one of technological method be most widely used in preventing and removing marine fouling organisms.But, tradition antifouling paint is by discharging poison material and toxic action suppresses the attachment of fouling organism, there is the shortcomings such as toxicity is large, validity period is short, and the stain control agent discharged also also exists the risk of the harm marine eco-environment, therefore, the stain control agent of development of new, efficient, low toxicity, environmental protection has become current urgent problem and study hotspot.
Understand fully that the antifouling mechanism of action of marine organisms native chemical can be the nuisanceless stain control agent of exploitation and offers reference, and marine organisms itself also should be the important sources of novel antifouling agent.Because the comparision contents of antifouling activity material in marine animal and microorganism is few, be not easy to deep exploitation and widespread use, therefore natural anti-fouling agent is found from the large marine plant of marine stock biomass, be not only a kind of trial completely newly, and there is important theory and realistic meaning.
Acid amides is that a class has peptide bond structure and is distributed widely in the compound in marine alga, it has the biological activitys such as anti-oxidant, anti-inflammatory, antibacterial and insecticidal action, but, in preventing and removing marine fouling organisms field, there is not report to be disclosed acetic acid orange acid amides anti-attachment effect and to use it for fouling organism and prevent and kill off aspect.
Summary of the invention
For deficiency of the prior art, the invention provides the application of acetic acid orange acid amides in preventing and removing marine fouling organisms.
Another object of the present invention is to provide acetic acid orange acid amides prevents marine organisms from adhering to or/and application in stained antifouling paint in preparation.
Above-mentioned purpose of the present invention is achieved by the following technical programs.
The application of acetic acid orange acid amides in preventing and removing marine fouling organisms.
The structural formula of acetic acid orange acid amides is:
, molecular formula C
27h
28n
2o
4, molecular weight is 444.Compared with other amide substances, acetic acid orange amide molecule structure is unique, wherein comprises 3 phenyl ring, 1 acetoxyl group, 2 amide group, and these groups are the groups played a crucial role in acetic acid orange acid amides anti-soil process.Acetic acid of the present invention orange acid amides can be the common commercially available or crude substance that extracts from plant.
From marime fouling angle, after fouling organism starts from set or attachment to the harm that the mankind produce, the present invention finds that described acetic acid orange acid amides effectively can suppress the settlement and metamorphosis process of various fouling organism larva, can effectively be applied in the biocontrol of marine fouling organism.Further, as naturally occurring organic compound, while the attachment of suppression marime fouling animal, acetic acid orange acid amides can not cause the pollution of water body environment.Therefore, described acetic acid orange acid amides is a kind of natural, environmental protection, has the compound of good antibiont attachment activity, has a good application prospect in the fouling organism of all kinds of maritime facilities is prevented and kill off.
Preferably, described fouling organism is that cirrus class is or/and mussels is biological.The present invention experimental studies have found that through a large amount of, and the attachment of described acetic acid orange acid amides to cirrus class and mussels has remarkable restraining effect, and cirrus class and mussels belong in marine fouling organism and endanger comparatively large and be difficult to the biological species removed.
Preferably, be that acetic acid orange acid amides is coated on body surface, coated weight>=0.1 μ g/cm when preventing and kill off marine fouling organism
2.Described acetic acid orange acid amides is coated on body surface, effectively can suppresses the attachment of marine fouling organism.
Preferably, the coated weight of described acetic acid orange acid amides is 0.1 ~ 1 μ g/cm
2, within the scope of described coated weight, the attachment of acetic acid orange acid amides to fouling organism produces obvious restraining effect, and does not have obvious toxicity to marine organisms.
Preferably, described acetic acid orange acid amides extracts to obtain from sargassun.
Acetic acid orange acid amides prevents marine organisms from adhering to or/and application in stained antifouling paint in preparation.
From sargassun, extract the method obtaining acetic acid orange acid amides, comprise the steps:
S1. sargassun is used 95% alcoholic extraction, obtain extracting solution;
S2. sherwood oil, extraction into ethyl acetate is used respectively after extracting solution concentrating under reduced pressure;
S3. get petroleum ether portion through silica gel column chromatography, during chromatography, elutriant used is normal hexane and acetone soln;
S4. get the solution after S3 wash-out again through gel filtration chromatography purifying, during chromatography, elutriant used is methanol solution, or is the mixing solutions of chloroform and methyl alcohol, namely obtains described acetic acid orange acid amides after elutriant recrystallization.
Described method for separating and preparing is easy, and raw material sources is stablized, and is applicable to scale operation and promotes.
More preferably, described extracting method, comprises the steps:
S1. by sargassun 95% alcoholic extraction three times, extracting solution is obtained;
S2. be scattered in water after extracting solution concentrating under reduced pressure, use sherwood oil, extraction into ethyl acetate three times respectively;
S3. petroleum ether portion is got through purification on normal-phase silica gel column chromatography, during chromatography, elutriant used is that normal hexane is or/and the gradient eluent of acetone composition, wherein normal hexane: the volume ratio of acetone is respectively 10:0,8:2,4:6,6:4,2:8,0:10, wash-out obtains 10 component F1 ~ F10;
S4. get component F7 wherein again through gel filtration chromatography purifying, during chromatography, elutriant used is chloroform and methanol solution, wherein, and chloroform: the volume ratio of methyl alcohol is 1:1, then through recrystallization purifying, obtain described acetic acid orange acid amides.
Compared with prior art, beneficial effect of the present invention is:
(1) the present invention finds that acetic acid orange acid amides effectively can suppress the settlement and metamorphosis process of various fouling organism larva, and the acetic acid orange acid amides of low dosage can have significant restraining effect to halobiontic attachment.Further, as naturally occurring organic compound, the not heavy metal element such as cupric and tin, while the attachment of suppression marime fouling animal, the enrichment that acetic acid orange acid amides can not cause the pollution of water body environment and cause it in organism by food chain transmission.Therefore, described acetic acid orange acid amides is a kind of natural, environmental protection, has the compound of good antibiont attachment activity, has a good application prospect in the fouling organism of all kinds of maritime facilities is prevented and kill off.
(2) acetic acid disclosed by the invention orange acid amides is separated that to prepare approach easy, is suitable for scale operation, applies potentiality large, have a good application prospect in preventing and removing marine fouling organisms.
Embodiment
Below in conjunction with specific embodiment, the present invention is described in further details, but embodiment does not limit in any form the present invention.Unless stated otherwise, the present invention adopts reagent, method and apparatus are the art conventional reagent, method and apparatus.
Present embodiment is selected to endanger in marine fouling organism comparatively large and is difficult to the cirrus class barnacle removed and mussels mussel is tested object.At tropical littoral sea, barnacle is the Typical Representative of stockless cirrus class, and is the dominant species in fouling community; Mussel is then the common bivalve in the East Sea and the South Sea, is also to be attached to fouling organism kind important on boats and ships, boat (floating) mark and aquaculture installation.In addition, from marime fouling angle, fouling organism produces harm to the mankind and starts from set or after adhering to, if effectively suppress the settlement and metamorphosis of larva, just can reach the object of preventing and kill off.
Therefore, present embodiment adopts reticulate pattern barnacle and the halobiontic larva of Perna uiridis (Linnaeus) two class as experimental subjects, and the anti-fouling effect checking acetic acid orange acid amides is scientific and reasonable and representative meaning, and not as limiting the scope of the present invention.
embodiment 1
From the sargassun of island in Guangdong Province, extract acetic acid orange acid amides, comprise the steps:
S1. by 95% alcoholic extraction three times of island in Guangdong Province sargassun, extracting solution is obtained;
S2. be scattered in water after extracting solution concentrating under reduced pressure, use sherwood oil, extraction into ethyl acetate three times respectively;
S3. petroleum ether portion is got through purification on normal-phase silica gel column chromatography, during chromatography, elutriant used is the gradient eluent of normal hexane and acetone composition, wherein normal hexane: the volume ratio of acetone is respectively 10:0,8:2,4:6,6:4,2:8,0:10, wash-out obtains 10 component F1 ~ F10;
S4. get component F7 wherein again through gel filtration chromatography purifying, during chromatography, elutriant used is chloroform and methanol mixed solution, wherein chloroform: the volume ratio of methyl alcohol is 1:1, then through recrystallization purifying, obtains acetic acid orange acid amides.
Extract the acetic acid orange acid amides obtained to can be used for preventing and kill off of marine fouling organism and prepare preventing marine organisms from adhering to or/and stained antifouling paint.
embodiment 2
Experimental group I: embodiment 1 is extracted the acetic acid orange acid amides chloroform obtained and dissolve, be mixed with the solution that concentration is 28.26 μ g/ml.Be add this solution of 1 ml in the culture dish of 6cm at diameter, and make bottom its uniform fold culture dish.After solvent volatilizees completely, the acetic acid orange amide content be coated on bottom culture dish is 1 μ g/cm
2.Add 10 ml seawater.
Experimental group II: embodiment 1 is extracted the acetic acid orange acid amides chloroform obtained and dissolve, be mixed with the solution that concentration is 2.826 μ g/ml.Be add this solution of 1 ml in the culture dish of 6cm at diameter, and make bottom its uniform fold culture dish.After solvent volatilizees completely, the acetic acid orange amide content be coated on bottom culture dish is 0.1 μ g/cm
2.Add 10 ml seawater.
Acetic acid orange acid amides of the present invention forms coating in the bottom of culture dish, and acetic acid orange acid amides is insoluble to seawater, and the object adding seawater is to cultivate marine fouling organism.
Control group: add 1 ml chloroform, makes it be uniformly distributed in bottom culture dish, to be evaporatedly adds 10 ml seawater completely again.
Blank group: add 10 ml seawater.
Experimental group, blank group and control group respectively establish 5 Duplicate Samples.In each sample, add 30 reticulate pattern barnacle cyprids respectively, being placed in temperature is cultivate in dark surrounds in the constant incubator of about 29 DEG C, observes once every 24 hours.Cultivate attachment final to each group of larva after 72 hours and death state carries out statistical study.
Table 1 lists attachment and the mortality ratio of experimental group, control group and blank group cyprids.Result shows, cultivate in constant incubator after 72 hours, the larva adhesive rate of blank group is 85%, control group 83%, the adhesive rate of blank group and control group cyprids, without significant difference (p>0.05), can not leave over the objectionable impurities affecting cyprids activity after showing the chloroform volatilization as solvent.For the experimental group through acetic acid orange amide-treated, adhesive rate≤10% of its cyprids, is far smaller than control group, and difference extremely significantly (p<0.01); In addition, blank group, the larval mortality of control group and experimental group is 0, shows that this compound can suppress the attachment of reticulate pattern barnacle cyprids effectively and this dosage can not produce toxic action to larva.
Table 1 reticulate pattern barnacle cyprids attachment
embodiment 3
Experimental group: embodiment 1 is extracted the acetic acid orange acid amides chloroform obtained and dissolve, be mixed with the solution that concentration is 28.26 μ g/ml.Be add this solution of 1 ml in the culture dish of 6cm and make bottom its uniform fold culture dish at diameter.After solvent volatilizees completely, the acetic acid orange amide content be coated on bottom culture dish is 1.0 μ g/cm
2.Add 10 ml seawater.
Acetic acid orange acid amides of the present invention forms coating in the bottom of culture dish, and acetic acid orange acid amides is insoluble to seawater, and the object adding seawater is to cultivate marine fouling organism.
Control group: add 1 ml chloroform, makes dissolution homogeneity be distributed in bottom culture dish, treats that solvent evaporates is complete, then adds 10 ml seawater.
Blank group: add 10 ml seawater.
The determination of larva quantity: get the water body containing Perna uiridis (Linnaeus) veliger from nursery pond and concentrate with bolting silk.Point respectively get 50 ml three times, instillation 1-2 drips formalin solution and kills in counted under microscope after larva, and averaging of income value is the density of larva in water body.
Experimental group, blank group and control group all establish 5 Duplicate Samples, add about 30 Perna uiridis (Linnaeus) larvas, be then about in temperature in the incubator of 26 DEG C and cultivate under dark surrounds in each group, observe once every 24 hours.Cultivate attachment final to each group of larva after 72 hours and death state carries out statistical study.
Table 2 lists experimental group, control group and blank attachment and the mortality ratio organizing Perna uiridis (Linnaeus) larva.Visible, cultivate in constant incubator after 72 hours, the larva adhesive rate of blank group is about 30%, control group about 31%, the adhesive rate of blank group and control group veliger, without significant difference (p>0.05), can not leave over the objectionable impurities affecting veliger activity after showing the chloroform volatilization as solvent.And through the experimental group of acetic acid orange amide-treated, the adhesive rate of its larva is only 3.0%, and well below control group, difference extremely significantly (p<0.01), shows that this compound can suppress the attachment of Perna uiridis (Linnaeus) larva effectively.
Table 2 Perna uiridis (Linnaeus) veliger larva attachment
Claims (7)
1. the application of acetic acid orange acid amides in preventing and removing marine fouling organisms.
2. application according to claim 1, is characterized in that, described fouling organism is that cirrus class is or/and mussels is biological.
3. application according to claim 1, is characterized in that, is acetic acid orange acid amides is coated on body surface, coated weight>=0.1 μ g/cm when preventing and kill off marine fouling organism
2.
4. application according to claim 3, is characterized in that, the coated weight of described acetic acid orange acid amides is 0.1 ~ 1 μ g/cm
2.
5. application according to claim 1, is characterized in that, described acetic acid orange acid amides extracts to obtain from sargassun.
6. acetic acid orange acid amides prevents marine organisms from adhering to or/and application in stained antifouling paint in preparation.
7. application according to claim 5, is characterized in that, extracts the method obtaining acetic acid orange acid amides and comprise the steps: from sargassun
S1. sargassun is used 95% alcoholic extraction, obtain extracting solution;
S2. sherwood oil, extraction into ethyl acetate is used respectively after extracting solution concentrating under reduced pressure;
S3. get petroleum ether portion through silica gel column chromatography, during chromatography, elutriant used is normal hexane and acetone soln;
S4. get the solution after S3 wash-out again through gel filtration chromatography purifying, during chromatography, elutriant used is methanol solution, or is the mixing solutions of chloroform and methyl alcohol, namely obtains described acetic acid orange acid amides after elutriant recrystallization.
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Cited By (4)
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| CN108056112A (en) * | 2017-12-28 | 2018-05-22 | 中国科学院南海海洋研究所 | Sargassum henslowianum acetic acid ethyl ester extract separation component A and preparation method thereof and the application in preventing and removing marine fouling organisms |
| CN108124908A (en) * | 2017-12-28 | 2018-06-08 | 中国科学院南海海洋研究所 | Sargassum henslowianum acetic acid ethyl ester extract separation component C and preparation method thereof and the application in preventing and removing marine fouling organisms |
| CN108308199A (en) * | 2018-02-08 | 2018-07-24 | 广东海洋大学 | Sargassum henslowianum acetic acid ethyl ester extract separation component D and preparation method thereof and the application in preventing and removing marine fouling organisms |
| CN108477224A (en) * | 2018-02-08 | 2018-09-04 | 广东海洋大学 | Sargassum henslowianum acetic acid ethyl ester extract separation component B and preparation method thereof and the application in preventing and removing marine fouling organisms |
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| CN108308199B (en) * | 2018-02-08 | 2020-12-08 | 广东海洋大学 | Component D separated from sargassum henryi ethyl acetate extract, preparation method thereof and application of component D in marine fouling organism prevention and removal |
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