CN102093322A - Application of osthole in preparation of marine antifouling paint - Google Patents
Application of osthole in preparation of marine antifouling paint Download PDFInfo
- Publication number
- CN102093322A CN102093322A CN2010106185925A CN201010618592A CN102093322A CN 102093322 A CN102093322 A CN 102093322A CN 2010106185925 A CN2010106185925 A CN 2010106185925A CN 201010618592 A CN201010618592 A CN 201010618592A CN 102093322 A CN102093322 A CN 102093322A
- Authority
- CN
- China
- Prior art keywords
- osthole
- marine
- preparation
- application
- ocean
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Abstract
The invention relates to application of osthole, and particularly provides application of osthole in the preparation of a marine antifouling paint. The molecular formula of the osthole is C15H16O3, the molecular weight is 244.29, and the chemical name is 7-methoxyl-8-isopentenyl coumarin. The osthole has obvious inhibiting effects on marine micro fouling organisms, marine macro soft fouling organisms and marine macro hard fouling organisms, indicates high-efficiency and broad-spectrum antifouling activities, and is widely applied to the preparation of the marine antifouling paint. Because the osthole is a natural compound, the marine antifouling composition prepared from the osthole does not contain toxic heavy metal compounds and can not pollute the environment. The osthole extraction and preparation process is simple and mature, thereby being beneficial to the popularization and application of the osthole in the preparation of the marine antifouling paint.
Description
Technical field
The present invention relates to the purposes of osthole, the particularly application of osthole in the preparation marine antifouling coating.
Background technology
In ocean environment, after object immersed in the seawater, its surface at first took place miniature stained, and promptly miniature organism such as bacterium is attached on the body surface, and grows thereon, breeds; Subsequently, the young of the spore of macro and marine invertebrate such as barnacle, mussel and Ascidian is attached on the body surface, and this process is called as large-scale stained.Large-scale stained can be further divided into again soft stained and rigid stained, soft stained be meant algae, careless tongue worm, Ascidian, hydra etc. biology caused stained, it is stained that the rigid stained biology that is meant secretion lime carbonate shell such as barnacle and oyster etc. are caused.These marine fouling organisms are attached to marine artificial facility surface, can strengthen ship resistance, blocking pipe and breed netting gear, influence serious harms such as the normal use of acoustic instrument and other offshore set-ups, the burden that increases marine oil and Natural gas extraction platform, acceleration metallic corrosion, cause the massive losses of ocean Military activity, sea transport, industry and aquaculture production.
Up to now, solving marine biofouling method most economical, effective and commonly used is the coating that contains marine antifoulant in marine equipment surface brushing, it mainly acts on is key ingredient by in the coating---mode such as the oozing out of marine antifoulant, diffusion or hydrolysis progressively discharges stain control agent, reaches to prevent the purpose of marine fouling organism attached to marine artificial facility surface.Present marine antifoulant kind major part contains heavy metal, the strong toxicity of tool, Marine Pollution ecotope.Once be used as marine antifoulant as organo-tin compound and be extensive use of, but forbidden on boats and ships, using by legislation because of it is hypertoxic.Though Red copper oxide is main in the market marine antifoulant, its a large amount of uses also can havoc marine ecology balance, even can jeopardize human health by the transmission of food chain.Therefore, exploitation environment-friendly type marine antifoulant has become the important topic of being badly in need of solution in the world.Natural active matter itself promptly comes from nature, possesses biodegradability, is a kind of circulation of natural resources, can not cause additional pressure to environment, if can be developed as marine antifoulant, then is expected to substitute environmentally harmful marine antifoulant.Disclose a kind of capsaicin antifouling paint as Chinese patent CN200510013553.1, as stain control agent, prevented that marine organisms from adhering to the natural active matter capsicine that from capsicum, extracts.
Osthole belongs to coumarin kind compound, and the main fruit that extracts from the samphire cnidium monnieri has effects such as antitumor, desinsection, antibiotic, relieving inflammation and relaxing pain, anticoagulation, anti-ageing, anti-arrhythmia, hypertension, osteoporosis disease.It is reported (Chinese invention patent 03132336.7), osthole can be applicable to medically, diseases such as cardiovascular, reproductive system there is therapeutic action, also can be used as food preservative and sanitas, and can be used as insecticidal bactericide and be applied to agricultural and go up anti-insect pest such as eliminate aphis.Publication number is that the Chinese invention patent application of CN101780071A discloses the new purposes of osthole in preparation control myocardial fibrosis medicine.Publication number is that the Chinese invention patent application of CN101720765A discloses osthole and kills application in the fall webworms preparation in preparation; the preparation of this invention preparation has the effect of tagging preferably to fall webworms; and, compare with general chemical pesticide and more to help environment protection people and animals and other mammalian safe.Up to now, yet there are no the report of in the preparation marine antifouling coating, using about osthole.
Summary of the invention
The object of the present invention is to provide the application of osthole in the preparation marine antifouling coating.
The molecular formula of described osthole is C
15H
16O
3, molecular weight is 244.29, and chemical name is 7-methoxyl group-8-isopentene group tonka bean camphor, and chemical structural formula is:
Described osthole can obtain from the fruit Fructus Cnidii of cnidium monnieri in separation and purification, and is water insoluble, is dissolved in organic solvents such as acetone, methyl alcohol, ethanol, chloroform, ether, ethyl acetate.
Described osthole demonstrates antifouling activity efficient, wide spectrum to the miniature fouling organism in ocean, the equal tool significant inhibitory effect of the large-scale rigid fouling organism of large-scale soft fouling organism in ocean and ocean, has widely in the preparation marine antifouling coating and uses.
The invention has the advantages that: osthole is naturally occurring compound, with not containing the toxicity heavy metal compound in the marine antifoulant of its preparation, can not pollute environment.Osthole can effectively suppress adhering to of the miniature fouling organism in ocean, the large-scale soft fouling organism in ocean and the large-scale rigid fouling organism in ocean, demonstrates the antifouling usefulness of wide spectrum.Osthole is insoluble in water, and lipophilicity is good, and good compatibility is arranged in coating, its release rate easy to control.The extracting and preparing technique of osthole is simply ripe at present, also helps its applying in the preparation marine antifouling coating.
Embodiment
Embodiment 1 osthole detects the restraining effect of the miniature fouling organism in ocean
The biological detection model of the miniature fouling organism in ocean adopts topmost miniature fouling organism---marime fouling bacterium in the ocean.Marime fouling bacterium pseudomonas (Pseudomonas sp.) can also can be used the surface of steel plate of conventional microorganism separation method from be dipped in Xiamen sea area to separate and obtain available from DSMZ of Institute of Microorganism, Academia Sinica.
Pseudomonas is inoculated in the 2216E liquid nutrient medium, centrifugal collection bacterium after the shaking table overnight incubation, with aseptic seawer washing and make suspension, bacterial concentration reaches 10 approximately
7～10
9Individual/ml.Osthole is dissolved in earlier in the ethyl acetate of trace, mixes with the bacterial suspension that makes by the concentration of 0.1,1,10 and 50 μ g/ml then, add in the culture dish.To add bacterium suspension and micro-acetic acid ethyl ester but the culture dish that does not add osthole is a control group.Each experimental group is all established 3 parallel cups with control group, after cultivating 3h under 30 ℃, washs culture dish repeatedly gently with aseptic seawater.
Soak culture dish with 4% formaldehyde, with distilled water flushing, then with the DAPI of 0.5 μ g/mL (4 ', 6-diamidino-2-phenylindone, 4 ', 6-diamidino-2-phenylindole) dyeing 5min.Under fluorescent microscope, get 9 visual field countings at random, obtain the quantity of adhering to of bacterium.Experimental result has confirmed that osthole can significantly suppress adhere to (referring to table 1) of marime fouling bacterium under lower concentration, and concentration (EC is adhered in its half inhibition
50Value refers to suppress the effective concentration that 50% detection of biological is adhered to, and this value is low more, shows that antifouling activity is high more) only be 10.74 ± 0.68 μ g/ml.
Table 1
Embodiment 2 ostholes detect the restraining effect of the large-scale soft fouling organism in ocean
The biological detection model of the large-scale soft fouling organism in ocean adopts it to represent biological careless tongue worm.Bugula neritina (Bugulaneritina) adult picks up from the steck aquaculture net cage of Xiamen west marine site, puts into the glass jar that fills fresh seawater after taking back the laboratory, and induces floating larva to discharge with the source of artificial light direct irradiation above glass jar.Adhering to of its floating larva causes careless tongue worm to turn to epiphytism by the life of swimming just, and therefore suppressing adhering to of floating larva is that provable compound has antifouling activity.
With osthole with acetic acid ethyl dissolution, concentration gradient is set to 0.5,5,10 and 25 μ g/ml, getting each solution of 10ml respectively joins in the culture dish, the ethyl acetate that other gets 10ml is added in the barren culture dish, be made as corresponding control group, treat that solvent evaporates fully, after each extract is evenly distributed on culture dish bottom surface and side, the membrane filtration seawater (via hole diameter is the membrane filtration of 0.22 μ m) that adds 10ml is in each glass culture dish.Each experimental group is all established 3 parallel cups with control group, and every glass adds several 30～80 of careless tongue worm floating larva.
After dropping into careless tongue worm floating larva 24h, with the adhesion condition of stereomicroscope observation floating larva.Experimental result has confirmed that osthole can significantly suppress adhere to (referring to table 2) of careless tongue worm under lower concentration, and it suppresses to adhere to concentration EC to half of the large-scale soft fouling organism grass tongue worm in ocean
50Value only is 3.71 ± 0.07 μ g/ml.
Table 2
Embodiment 3 ostholes detect the restraining effect of the large-scale rigid fouling organism in ocean
The biological detection model of the large-scale rigid fouling organism in ocean adopts it to represent biological barnacle.White ridge barnacle (Balanusalbicostatus) adult is gathered on the reef of Baicheng, Xiamen City seashore and bridge pier and is obtained, and its cypris larva obtains at the experiment indoor cultivation.Adhering to of cypris larva causes barnacle to turn to epiphytism by the life of swimming just, and therefore suppressing adhering to of cypris larva is that provable compound has antifouling activity.
With osthole with acetic acid ethyl dissolution, concentration gradient is set to 0.5,2.5,5 and 10 μ g/ml, getting each solution of 10ml respectively joins in the culture dish, the ethyl acetate that other gets 10ml is added in the barren culture dish, be made as corresponding control group, treat that solvent evaporates fully, after each extract is evenly distributed on culture dish bottom surface and side, the membrane filtration seawater that adds 10ml is in each glass culture dish.Each experimental group is all established 3 parallel cups with control group, and every glass adds several 30～80 of cypris larva.
After dropping into cypris larva 48h, with the adhesion condition of stereomicroscope observation cypris larva.Experimental result has confirmed that osthole can significantly suppress adhere to (referring to table 3) of barnacle under lower concentration, and it suppresses to adhere to concentration EC to half of the large-scale rigid fouling organism barnacle in ocean
50Value also only is 4.64 ± 0.04 μ g/ml.
Table 3
The anti-fouling effect evaluation of embodiment 4 ostholes in natural sea area
With reference to national standard " antifouling varnish model shallow sea soak test method " (GB/T 5370-2007), the check osthole is as the antifouling usefulness of marine antifoulant in the sea area, Xiamen.Carry out the link plate experiment summer that the Yu Haiyang fouling organism is flouring, at natural sea area link plate after 4 months, calculate the fouling organism coverage on the plate, find 6 biodeterioration coverage average out to 4.5% that have been coated with the test piece surface of osthole, significantly be lower than the contrast model, the biodeterioration coverage average out to 98.6% of contrast model shows the anti-fouling effect that the osthole tool is good.
Found through experiments, osthole suppresses adhewsive action significantly to the miniature fouling organism in ocean, the equal tool of the large-scale rigid fouling organism of large-scale soft fouling organism in ocean and ocean under lower concentration, demonstrate antifouling activity efficient, wide spectrum, can be used as the broad spectrum type marine antifoulant.Wherein, osthole effectively suppresses to dwell at the bottom of the miniature fouling organism ocean, ocean adhering to of pseudomonas, and it half suppresses to adhere to concentration EC
50Only be 10.74 ± 0.68 μ g/ml; Osthole suppresses to adhere to concentration EC to half of the large-scale soft fouling organism grass tongue worm in ocean
50Only be 3.71 ± 0.07 μ g/ml; Osthole suppresses to adhere to concentration EC to half of the large-scale rigid fouling organism barnacle in ocean
50Also only be 4.64 ± 0.04 μ g/ml.As seen, the present invention marine organisms of being suitable for controlling comprise the miniature fouling organism in ocean, the large-scale rigid fouling organism of large-scale soft fouling organism in ocean and ocean.
Osthole can ordinary method be prepared into marine antifouling coating, shows the tangible anti-fouling effect of its tool through natural sea area board experiment, and the marine fouling organism that visible osthole can be applied to natural sea area is antifouling, has verified laboratory detection effect.Osthole among the present invention not only can be used to prepare marine antifouling coating as stain control agent separately, also can with the use that is mixed of other stain control agent, reduce the toxicity of antifouling paint.
Claims (2)
1. osthole is characterized in that its molecular formula is C
15H
16O
3, molecular weight is 244.29, and chemical name is 7-methoxyl group-8-isopentene group tonka bean camphor, and chemical structural formula is:
2. the application of osthole as claimed in claim 1 in the preparation marine antifouling coating.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010106185925A CN102093322A (en) | 2010-12-31 | 2010-12-31 | Application of osthole in preparation of marine antifouling paint |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN2010106185925A CN102093322A (en) | 2010-12-31 | 2010-12-31 | Application of osthole in preparation of marine antifouling paint |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN102093322A true CN102093322A (en) | 2011-06-15 |
Family
ID=44126609
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN2010106185925A Pending CN102093322A (en) | 2010-12-31 | 2010-12-31 | Application of osthole in preparation of marine antifouling paint |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN102093322A (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103190405A (en) * | 2013-04-16 | 2013-07-10 | 江苏省中国科学院植物研究所 | Use of natural compound as agricultural bactericide or pesticide |
| CN103819983A (en) * | 2013-12-11 | 2014-05-28 | 青岛海洋新材料科技有限公司 | Novel ocean antifouling paint |
| CN103858874A (en) * | 2013-04-16 | 2014-06-18 | 江苏省中国科学院植物研究所 | Application of natural compound as agricultural bactericide |
| CN104230874A (en) * | 2013-09-11 | 2014-12-24 | 中国海洋大学 | Preparation method of isocoumarin compound and application of isocoumarin compound as antibacterial agent |
| CN104230873A (en) * | 2013-09-11 | 2014-12-24 | 中国海洋大学 | Isocoumarin compound as well as preparation method and application of isocoumarin compound as natural marine organism antifouling agent |
| CN104327035A (en) * | 2013-12-14 | 2015-02-04 | 于跃 | Marine fungi secondary metabolite derivative and application of marine fungi secondary metabolite derivative as marine biological antifoulant |
| CN105331168A (en) * | 2015-12-02 | 2016-02-17 | 厦门大学 | Application of cardiac glycoside compound in marine biofouling prevention |
| CN105602322A (en) * | 2016-02-26 | 2016-05-25 | 蚌埠赛尔时代工贸有限公司 | External protective paint for artificial marble |
| CN105647341A (en) * | 2016-02-26 | 2016-06-08 | 蚌埠赛尔时代工贸有限公司 | Inner protection coating for manufacture of waterproof fabric |
| CN105670445A (en) * | 2016-02-26 | 2016-06-15 | 蚌埠赛尔时代工贸有限公司 | Outer-layer protective coating for manufacturing plastic barrel |
| CN105778707A (en) * | 2016-02-26 | 2016-07-20 | 蚌埠赛尔时代工贸有限公司 | Inner-wall protective coating for manufacturing faucet |
| CN107474547A (en) * | 2017-09-12 | 2017-12-15 | 吉林大学 | Application of the elastomeric material in biodeterioration is prevented |
| CN115851110A (en) * | 2022-12-21 | 2023-03-28 | 浙江大学 | Preparation method of coumarin-based photoresponse long-acting super-lubricating antifouling paint |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55130905A (en) * | 1979-04-02 | 1980-10-11 | Nippon Paint Co Ltd | Agent for preventing adhesion of aquatic life |
| JPS5640601A (en) * | 1979-09-10 | 1981-04-16 | Nippon Paint Co Ltd | Deposition inhibitor for living thing in water |
-
2010
- 2010-12-31 CN CN2010106185925A patent/CN102093322A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55130905A (en) * | 1979-04-02 | 1980-10-11 | Nippon Paint Co Ltd | Agent for preventing adhesion of aquatic life |
| JPS5640601A (en) * | 1979-09-10 | 1981-04-16 | Nippon Paint Co Ltd | Deposition inhibitor for living thing in water |
Non-Patent Citations (1)
| Title |
|---|
| 魏文军: "蛇床子素衍生物的合成及生物活性研究", 《华中农业大学硕士学位论文》, 31 December 2009 (2009-12-31) * |
Cited By (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103858874A (en) * | 2013-04-16 | 2014-06-18 | 江苏省中国科学院植物研究所 | Application of natural compound as agricultural bactericide |
| CN103190405A (en) * | 2013-04-16 | 2013-07-10 | 江苏省中国科学院植物研究所 | Use of natural compound as agricultural bactericide or pesticide |
| CN104230874B (en) * | 2013-09-11 | 2017-02-01 | 中国海洋大学 | Preparation method of isocoumarin compound and application of isocoumarin compound as antibacterial agent |
| CN104230873B (en) * | 2013-09-11 | 2017-02-01 | 中国海洋大学 | Isocoumarin compound as well as preparation method and application of isocoumarin compound as natural marine organism antifouling agent |
| CN104230873A (en) * | 2013-09-11 | 2014-12-24 | 中国海洋大学 | Isocoumarin compound as well as preparation method and application of isocoumarin compound as natural marine organism antifouling agent |
| CN104230874A (en) * | 2013-09-11 | 2014-12-24 | 中国海洋大学 | Preparation method of isocoumarin compound and application of isocoumarin compound as antibacterial agent |
| CN103819983A (en) * | 2013-12-11 | 2014-05-28 | 青岛海洋新材料科技有限公司 | Novel ocean antifouling paint |
| CN104327035A (en) * | 2013-12-14 | 2015-02-04 | 于跃 | Marine fungi secondary metabolite derivative and application of marine fungi secondary metabolite derivative as marine biological antifoulant |
| CN104327035B (en) * | 2013-12-14 | 2017-03-22 | 于跃 | Marine fungi secondary metabolite derivative and application of marine fungi secondary metabolite derivative as marine biological antifoulant |
| CN105331168A (en) * | 2015-12-02 | 2016-02-17 | 厦门大学 | Application of cardiac glycoside compound in marine biofouling prevention |
| CN105778707A (en) * | 2016-02-26 | 2016-07-20 | 蚌埠赛尔时代工贸有限公司 | Inner-wall protective coating for manufacturing faucet |
| CN105670445A (en) * | 2016-02-26 | 2016-06-15 | 蚌埠赛尔时代工贸有限公司 | Outer-layer protective coating for manufacturing plastic barrel |
| CN105647341A (en) * | 2016-02-26 | 2016-06-08 | 蚌埠赛尔时代工贸有限公司 | Inner protection coating for manufacture of waterproof fabric |
| CN105602322A (en) * | 2016-02-26 | 2016-05-25 | 蚌埠赛尔时代工贸有限公司 | External protective paint for artificial marble |
| CN107474547A (en) * | 2017-09-12 | 2017-12-15 | 吉林大学 | Application of the elastomeric material in biodeterioration is prevented |
| CN115851110A (en) * | 2022-12-21 | 2023-03-28 | 浙江大学 | Preparation method of coumarin-based photoresponse long-acting super-lubricating antifouling paint |
| CN115851110B (en) * | 2022-12-21 | 2023-08-15 | 浙江大学 | Preparation method of light response long-acting super-lubricating anti-fouling paint based on coumarin |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN102093322A (en) | Application of osthole in preparation of marine antifouling paint | |
| CN101715770B (en) | Application of loop proline-3-hydroxy-2-aminobutyric acid in preventing and removing marine fouling organisms | |
| Armstrong et al. | Prevention of marine biofouling using natural compounds from marine organisms | |
| Feng et al. | The plant alkaloid camptothecin as a novel antifouling compound for marine paints: Laboratory bioassays and field trials | |
| Bazes et al. | Active substances from Ceramium botryocarpum used as antifouling products in aquaculture | |
| CN103289461B (en) | Camptothecin analogues is as the application of anti-fouling agent | |
| CN104356730B (en) | Application of class of butenolide compounds in preparation of marine biofouling prevention coating material | |
| CN110724403B (en) | Application of quinazolinone alkaloid compound derived from marine fungi in preventing and removing marine fouling organisms | |
| CN102757677A (en) | Application of class of indole alkaloids to preparation of marine biofouling prevention coating material | |
| CN101724305B (en) | Application of cycle (proline-alanine) in preventing and removing marine fouling organism | |
| Li et al. | Investigation on the efficiency of a silicone antifouling coating in controlling the adhesion and germination of Ulva prolifera micro-propagules on rafts | |
| JP2008504377A (en) | Environmentally friendly antifouling agent | |
| CN102093770B (en) | Application of the myrica extract in marine antifouling coating is prepared | |
| Iyapparaj et al. | Evidence for the antifouling potentials of marine macroalgae Sargassum wightii | |
| CN102771484A (en) | Berberine.artemisinin composite algicide | |
| CN106810926B (en) | A kind of application of aporphine alkaloid | |
| JP2007045811A (en) | Antisticking for attaching diatom | |
| CN102613201B (en) | Isoflavanone compound for protecting underwater structure surface and application thereof | |
| CN105331168A (en) | Application of cardiac glycoside compound in marine biofouling prevention | |
| Ma et al. | Inhibition of common fouling organisms in mariculture by epiphytic bacteria from the surfaces of seaweeds and invertebrates | |
| CN101485321B (en) | Application of oleanolic acid in preparing sea environment-friendly antifouling agent | |
| CN111269603B (en) | Application of pyrazine quinazolinedione alkaloid compound in preparation of marine fouling organism control agent | |
| CN110724149B (en) | Indole alkaloid dimer compound derived from marine fungi, preparation method and application of indole alkaloid dimer compound in marine fouling organism resistant control agent | |
| CN103642299A (en) | Application of benzoheterocycle alkaloids in preparation of marine organism stain preventing coatings | |
| CN102321089A (en) | Screw ring alkaloid compound, preparation method thereof and application in the aspect of marine organism fouling resistance |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C12 | Rejection of a patent application after its publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20110615 |