CN104592798B - Application of the acetic acid orange acid amides in preventing and removing marine fouling organisms - Google Patents
Application of the acetic acid orange acid amides in preventing and removing marine fouling organisms Download PDFInfo
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- CN104592798B CN104592798B CN201410833236.3A CN201410833236A CN104592798B CN 104592798 B CN104592798 B CN 104592798B CN 201410833236 A CN201410833236 A CN 201410833236A CN 104592798 B CN104592798 B CN 104592798B
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- acetic acid
- acid amides
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- fouling
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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)
- Paints Or Removers (AREA)
Abstract
The invention belongs to biological technical field, application of the acetic acid orange acid amides in preventing and removing marine fouling organisms is specifically disclosed.Present invention discover that acetic acid orange acid amides can effectively suppress the settlement and metamorphosis process of various fouling organism larvas, the acetic acid orange acid amides of low dosage just can have significant inhibitory action to the attachment of marine organisms, and, acetic acid orange acid amides does not result in the pollution of water body environment and transmits the enrichment for causing it in organism by food chain while the attachment of marime fouling animal is suppressed.Therefore, acetic acid orange acid amides is a kind of natural, environmental protection, the compound with good antibiont attachment activity, is had a good application prospect in the fouling organism of all kinds of marine facilities is prevented and kill off.
Description
Technical field
The invention belongs to biological technical field, in particular it relates to acetic acid orange acid amides answering in preventing and removing marine fouling organisms
With.
Background technology
Marine fouling organism refers to set or perches different kind organism in ship and marine facility underwater sites, fouling organism
Two life stages are generally divided into, one is the life stage that swims, i.e., are developed to from larva abjection egg membrane and explore thing off and on
Body surface face prepares the stage of settlement and metamorphosis；Two is that set or epiphytism stage, i.e. larva choose colonization sites, in attachment base table
Face attachment, the abnormal stage for forming the young.The harm that marine fouling organism produces mainly includes：Increase resistance, reduces the speed of a ship or plane, increases
Refuelling is consumed and CO2Discharge；Seawater piping systems are blocked, changes Process of Metallic Corrosion, trigger local corrosion or pitting corrosion；
Increase dynamic load(loading) effect, causes the drift of facility, unbalance even resulting in topple；With cultivation object（Such as shellfish）Contention attachment base
And bait, hinder it to grow, reduce the quality of product.
Antifouling paint is one of technical method for being most widely used in preventing and removing marine fouling organisms.However, tradition is anti-
Dirty coating suppresses the attachment of fouling organism by discharging poison and toxic action, has the shortcomings that toxicity is big, the term of validity is short, and
And the anti-fouling agent for discharging also has the risk of the harm marine eco-environment, therefore, develop new, efficient, low toxicity, environmental protection
Anti-fouling agent turned into current urgent problem and study hotspot.
Understand fully that the antifouling mechanism of action of marine organisms native chemical can offer reference for the nuisanceless anti-fouling agent of exploitation, and ocean
Biological itself also should be the important sources of novel antifouling agent.Due to content of the antifouling activity material in marine animal and microorganism
It is fewer, it is not easy to deeply develop and extensive use, therefore natural anti-fouling agent is found from the big sea-plant of marine stock biomass, no
Only it is a kind of brand-new trial, and with important theory and realistic meaning.
Acid amides is the compound that a class has peptide bond structure and is distributed widely in marine alga, and it has anti-oxidant, anti-inflammatory, resists
The bioactivity such as bacterium and insecticidal action, however, in preventing and removing marine fouling organisms field, not having been reported that open peracetic acid orange acid amides resists
Adhewsive action prevents and kill off aspect with fouling organism is used it for.
The content of the invention
For deficiency of the prior art, the invention provides acetic acid orange acid amides answering in preventing and removing marine fouling organisms
With.
Preparing what is prevented marine organisms attachment or/and be stained another object of the present invention is to provide acetic acid orange acid amides
Application in antifouling paint.
Above-mentioned purpose of the invention is achieved by the following technical programs.
Application of the acetic acid orange acid amides in preventing and removing marine fouling organisms.
Acetic acid orange acid amides structural formula be：
, molecular formula C27H28N2O4, molecular weight is 444.Compared with other amide substances, acetic acid orange amide molecule structure is only
Spy, wherein comprising 3 phenyl ring, 1 acetoxyl group, 2 amide groups, these groups are to play key during acetic acid orange acid amides anti-soil
The group of effect.Acetic acid orange acid amides of the present invention can be natural materials that are common commercially available or being extracted from plant.
From the point of view of marime fouling angle, fouling organism is started from after set or attachment to the harm that the mankind produce, the present invention
It was found that the acetic acid orange acid amides can effectively suppress the settlement and metamorphosis process of various fouling organism larvas, sea can be efficiently applied to
In the biological insect control of foreign fouling organism.Also, as naturally occurring organic compound, suppressing the attachment of marime fouling animal
Meanwhile, acetic acid orange acid amides does not result in the pollution of water body environment.Therefore, the 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 marine facilities is prevented and kill off.
Preferably, the fouling organism is that cirrus class or/and Bivalve are biological.The present invention sends out by substantial amounts of experimental study
Existing, attachment of the acetic acid orange acid amides to cirrus class and Bivalve has the effect that significantly inhibits, and cirrus class and Bivalve belong to sea
Biological species that are larger and being difficult to clean off are endangered in foreign fouling organism.
Preferably, it is that acetic acid orange acid amides is coated on body surface when preventing and kill off marine fouling organism, coated weight >=0.1 μ g/
cm2.Acetic acid orange acid amides is coated on body surface, can effectively suppress the attachment of marine fouling organism.
Preferably, the coated weight of the acetic acid orange acid amides is 0.1 ~ 1 μ g/cm2, in the range of the coated weight, acetic acid orange
Attachment of the acid amides to fouling organism produces obvious inhibiting effect, and does not have obvious toxicity to marine organisms.
Preferably, the acetic acid orange acid amides is to extract to obtain from sargassum.
Application of the acetic acid orange acid amides in the antifouling paint for preventing marine organisms attachment or/and being stained is prepared.
It is a kind of that the method for obtaining acetic acid orange acid amides is extracted from sargassum, comprise the following steps：
S1. by 95% alcoholic extraction of sargassum, extract solution is obtained；
S2. extracted with petroleum ether, ethyl acetate respectively after extract solution is concentrated under reduced pressure；
S3. petroleum ether portion is taken through silica gel column chromatography, and eluent used is n-hexane and acetone soln during chromatography；
S4. take the solution after S3 wash-outs to be purified through gel filtration chromatography again, eluent used is methanol solution during chromatography, or
It is chloroform and the mixed solution of methyl alcohol, the acetic acid orange acid amides is obtained final product after eluent recrystallization.
The method for separating and preparing is easy, raw material sources stabilization, is adapted to large-scale production and promotes.
It is highly preferred that the extracting method, comprises the following steps：
S1. by sargassum 95% alcoholic extraction three times, extract solution is obtained；
S2. it is dispersed in water after extract solution is concentrated under reduced pressure, is extracted three times with petroleum ether, ethyl acetate respectively；
S3. petroleum ether portion is taken through normal-phase silica gel column chromatography, and eluent used is n-hexane or/and third during chromatography
The gradient eluent of ketone composition, wherein n-hexane：The volume ratio of acetone is respectively 10:0、8:2、4:6、6:4、2:8、0:10, wash
It is de- to obtain 10 component F1 ~ F10；
S4. take component F7 therein to be purified through gel filtration chromatography again, eluent used is that chloroform and methyl alcohol are molten during chromatography
Liquid, wherein, chloroform：The volume ratio of methyl alcohol is 1:1, then through recrystallization purifying, obtain final product the acetic acid orange acid amides.
Compared with prior art, the beneficial effects of the present invention are：
（1）Present invention discover that acetic acid orange acid amides can effectively suppress the settlement and metamorphosis process of various fouling organism larvas, it is low
The acetic acid orange acid amides of dosage can have significant inhibitory action to the attachment of marine organisms.Also, have as naturally occurring
Machine compound, the not heavy metal element such as cupric and tin, while suppressing marime fouling animal and adhering to, acetic acid orange acid amides will not be made
Cause its enrichment in organism into the pollution of water body environment and by food chain transmission.Therefore, the acetic acid orange acid amides is
A kind of natural, environmental protection, the compound with good antibiont attachment activity, have in the fouling organism of all kinds of marine facilities is prevented and kill off
There is good application prospect.
（2）Acetic acid orange acid amides separation disclosed by the invention prepares approach simplicity, is suitable for large-scale production, and popularization and application are dived
Power is big, is had a good application prospect in preventing and removing marine fouling organisms.
Specific embodiment
The present invention is described in further details with reference to specific embodiment, but embodiment does not do any to the present invention
The restriction of form.Unless stated otherwise, the reagent for using of the invention, method and apparatus are the art conventional reagent, method
And equipment.
Cirrus class barnacle that is larger and being difficult to clean off is endangered in present embodiment selection marine fouling organism and Bivalve is made a gift of
Shellfish is test object.In tropical littoral sea, barnacle is the Typical Representative of stockless cirrus class, and is fouling community
Dominant species；Mussel is then the common bivalve in the East Sea and the South Sea, is also attached to ship, boat（It is floating）Mark and aquatic products
Fouling organism species important on breeding facility.In addition, from the point of view of marime fouling angle, fouling organism produces harm to begin the mankind
After set or attachment, if effectively suppressing the settlement and metamorphosis of larva, the purpose prevented and kill off can be just reached.
Therefore, present embodiment uses the larva of reticulate pattern barnacle and the class marine organisms of Perna viridis two as experimental subjects,
Anti-fouling effect to check acetic acid orange acid amides is scientific and reasonable and representative meaning, and not as to present invention protection model
The restriction enclosed.
Embodiment 1
Acetic acid orange acid amides is extracted from the sargassum of island in Guangdong Province, is comprised the following steps：
S1. by 95% alcoholic extraction three times of island in Guangdong Province sargassum, extract solution is obtained；
S2. it is dispersed in water after extract solution is concentrated under reduced pressure, is extracted three times with petroleum ether, ethyl acetate respectively；
S3. petroleum ether portion is taken through normal-phase silica gel column chromatography, and eluent used is n-hexane and acetone group during chromatography
Into gradient eluent, wherein n-hexane：The volume ratio of acetone is respectively 10:0、8:2、4:6、6:4、2:8、0:10, elute
To 10 component F1 ~ F10；
S4. take component F7 therein to be purified through gel filtration chromatography again, eluent used is that chloroform and methyl alcohol mix during chromatography
Solution, wherein chloroform：The volume ratio of methyl alcohol is 1:1, then through recrystallization purifying, obtain final product acetic acid orange acid amides.
Extract obtain acetic acid orange acid amides can be used for marine fouling organism prevent and kill off and prepares prevent marine organisms attachment or/
With the antifouling paint being stained.
Embodiment 2
Experimental group I：Embodiment 1 is extracted the acetic acid orange acid amides chloroform dissolving for obtaining, concentration is configured to for 28.26 μ g/
The solution of ml.The 1 ml solution is added in the culture dish of a diameter of 6cm, and makes its uniform fold culture dish bottom.Treat solvent
After volatilizing completely, the acetic acid orange amide content for being coated on culture dish bottom is 1 μ g/cm2.Add 10 ml seawater.
Experimental group II：Embodiment 1 is extracted the acetic acid orange acid amides chloroform dissolving for obtaining, concentration is configured to for 2.826 μ
The solution of g/ml.The 1 ml solution is added in the culture dish of a diameter of 6cm, and makes its uniform fold culture dish bottom.Treat molten
After agent is volatilized completely, the acetic acid orange amide content for being coated on culture dish bottom is 0.1 μ g/cm2.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 does not dissolve in seawater, adds sea
The purpose of water is to cultivate marine fouling organism.
Control group：Plus 1 ml chloroform, it is uniformly distributed in culture dish bottom, it is to be evaporated to add 10 ml seawater completely.
Blank group：Add 10 ml seawater.
Experimental group, blank group and control group respectively set 5 Duplicate Samples.30 reticulate pattern barnacle Venus are separately added into each sample
Larva, is placed in the constant incubator that temperature is 29 DEG C or so and is cultivated in dark surrounds, every observation in 24 hours once.Culture
The attachment final to each group larva and death state carry out statistical analysis after 72 hours.
Table 1 lists experimental group, the attachment of control group and blank group cyprids and the death rate.Result shows, in constant temperature
After being cultivated 72 hours in incubator, the larva adhesive rate of blank group is 85%, control group 83%, blank group and control group cyprids
Adhesive rate without significant difference（p>0.05）, show that influence cyprids activity will not be left after being volatilized as the chloroform of solvent
Harmful substance.For through acetic acid orange amide-treated experimental group, adhesive rate≤10% of its cyprids, far smaller than control group,
And difference is extremely notable（p<0.01）；In addition, the larval mortality of blank group, control group and experimental group is 0, show thisization
Compound can effectively suppress the attachment of reticulate pattern barnacle cyprids and the dosage will not produce toxic action to larva.
The reticulate pattern barnacle cyprids attachment of table 1
Embodiment 3
Experimental group：Embodiment 1 is extracted the acetic acid orange acid amides chloroform dissolving for obtaining, concentration is configured to for 28.26 μ g/
The solution of ml.The 1 ml solution is added in the culture dish of a diameter of 6cm and makes its uniform fold culture dish bottom.Treat that solvent is complete
After full volatilization, the acetic acid orange amide content for being coated on culture dish bottom is 1.0 μ g/cm2.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 does not dissolve in seawater, adds sea
The purpose of water is to cultivate marine fouling organism.
Control group：Plus 1 ml chloroform, solution is uniformly distributed in culture dish bottom, treat that solvent volatilization is complete, add 10
Ml seawater.
Blank group：Add 10 ml seawater.
Larva determination of amount：The water body containing Perna viridis veliger is taken from nursery pond and concentrated with bolting silk.In three times
50 ml are respectively taken, 1-2 drops formalin solution is instilled and is killed larva after counted under microscope, averaging of income value is in water body
The density of larva.
Experimental group, blank group and control group are all provided with 5 Duplicate Samples, and about 30 Perna viridis larvas are added in each group, connect
In being cultivated under dark surrounds in temperature is about 26 DEG C of incubator, every observation in 24 hours once.It is right after cultivating 72 hours
The final attachment of each group larva and death state carry out statistical analysis.
Table 2 lists experimental group, the attachment of control group and blank group Perna viridis larva and the death rate.It can be seen that, in constant temperature
After being cultivated 72 hours in incubator, the larva adhesive rate of blank group is about 30%, control group about 31%, blank group and control group face
The adhesive rate of larva is without significant difference（p>0.05）, show that influence veliger will not be left after being volatilized as the chloroform of solvent to live
The harmful substance of property.And through the experimental group of acetic acid orange amide-treated, the adhesive rate of its larva is only 3.0%, well below control
Group, difference is extremely notable（p<0.01）, show that this compound can effectively suppress the attachment of Perna viridis larva.
The Perna viridis veliger larva attachment of table 2
Claims (6)
1. application of the acetic acid orange acid amides in preventing and removing marine fouling organisms；The acetic acid orange acid amides is to extract to obtain from sargassum
, its structural formula such as formula（I）It is shown：
Formula（I）.
2. application according to claim 1, it is characterised in that the fouling organism is that cirrus class or/and Bivalve are biological.
3. application according to claim 1, it is characterised in that be by acetic acid orange acid amides coating when preventing and kill off marine fouling organism
In body surface, coated weight >=0.1 μ g/cm2。
4. application according to claim 3, it is characterised in that the coated weight of acetic acid orange acid amides is 0.1 ~ 1 μ g/cm2。
5. application of the acetic acid orange acid amides in the antifouling paint for preventing marine organisms attachment or/and being stained is prepared, the acetic acid orange
The structural formula of acid amides such as formula（I）It is shown：
Formula（I）.
6. application according to claim 1, it is characterised in that the method bag for obtaining acetic acid orange acid amides is extracted from sargassum
Include following steps：
S1. by 95% alcoholic extraction of sargassum, extract solution is obtained；
S2. extracted with petroleum ether, ethyl acetate respectively after extract solution is concentrated under reduced pressure；
S3. petroleum ether portion is taken through silica gel column chromatography, and eluent used is n-hexane and acetone soln during chromatography；
S4. take the solution after S3 wash-outs to be purified through gel filtration chromatography again, eluent used is methanol solution during chromatography, or is chlorine
The mixed solution of imitative and methyl alcohol, obtains final product the acetic acid orange acyl after eluent recrystallization.
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| CN108124908B (en) * | 2017-12-28 | 2020-11-10 | 中国科学院南海海洋研究所 | Component C separated from sargassum henryi ethyl acetate extract, preparation method thereof and application of component C in marine fouling organism prevention and removal |
| CN108056112B (en) * | 2017-12-28 | 2021-01-19 | 中国科学院南海海洋研究所 | Component A separated from ethyl acetate extract of sargassum henryi, preparation method thereof and application of component A in marine fouling organism prevention and removal |
| CN108477224B (en) * | 2018-02-08 | 2020-12-08 | 广东海洋大学 | Component B separated from sargassum henryi ethyl acetate extract, preparation method thereof and application of component B in marine fouling organism prevention and removal |
| 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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| CN101270174B (en) * | 2008-04-28 | 2012-01-11 | 海洋化工研究院 | Antifouling paint substrate resin and application |
| CN102070485B (en) * | 2010-12-27 | 2014-01-29 | 浙江大学 | Method for separating and purifying active component aurantiamide acetate from traditional Chinese medicine clematis terniflora |
| CN102757673B (en) * | 2011-04-27 | 2015-10-14 | 香港科技大学 | Amides is preventing the purposes in marine biofouling |
| CN102389131B (en) * | 2011-11-18 | 2013-06-19 | 广东海洋大学 | Sargassum integerrimum extract with antioxidant function and preparation method thereof |
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