CN103518722A - Application of 17-oxymethyl-7-hydroxy-benzene-furan-chalcone in preparing marine fouling organism control agent - Google Patents
Application of 17-oxymethyl-7-hydroxy-benzene-furan-chalcone in preparing marine fouling organism control agent Download PDFInfo
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- CN103518722A CN103518722A CN201310499561.6A CN201310499561A CN103518722A CN 103518722 A CN103518722 A CN 103518722A CN 201310499561 A CN201310499561 A CN 201310499561A CN 103518722 A CN103518722 A CN 103518722A
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- chalcone
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Abstract
The invention discloses an application of 17-oxymethyl-7-hydroxy-benzene-furan-chalcone in preparing a marine fouling organism control agent. The 17-oxymethyl-7-hydroxy-benzene-furan-chalcone has a structural formula shown as a formula (I) in the description. When a low dosage of 17-oxymethyl-7-hydroxy-benzene-furan-chalcone is coated on a solid surface, an obvious effect on inhibition of marine organism adhesion is achieved, and therefore, the 17-oxymethyl-7-hydroxy-benzene-furan-chalcone can be used for preparing the marine fouling organism control agent. The 17-oxymethyl-7-hydroxy-benzene-furan-chalcone is a natural organic compound, does not pollute water environments, is enriched in living organisms through food chain transportation, is environment-friendly, high in safety, free of heavy metal elements such as copper and tin while effectively inhibiting marine organism adhesion, simple and convenient in separation and preparation ways and suitable for large-scale production, and has good social benefit in the aspect of environmental protection, great popularization and application potentials and good application prospects for marine fouling organism control.
Description
Technical field:
The invention belongs to natural products field, be specifically related to the application of 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone in preparing preventing and removing marine fouling organisms agent.
Background technology:
Marine fouling organism refers to set or perches the different kind organism in boats and ships and marine facility underwater sites, and the harm of its generation is mainly increase resistance, reduces the speed of a ship or plane, increases fuel consumption and CO
2discharge; Stop up seawater pipeline system, change Process of Metallic Corrosion, cause local corrosion or pitting corrosion; Increase dynamic load(loading) effect, cause the drift of facility, unbalance even causing to topple; With cultivation object (as shellfish) contention adherance and bait, hinder it to grow, reduce the quality of product.
Antifouling paint is one of technical method being most widely used in preventing and removing marine fouling organisms.Yet, tradition antifouling paint is released to main path with poison material, by toxic action, suppress adhering to of fouling organism, there is toxicity large, the defects such as the term of validity is short, the antifouling composition discharging also exists the risk of the harm marine eco-environment, and therefore, development of new, efficient, low toxicity, environment-friendly antifouling agent have become current urgent problem and study hotspot.
Because marine fouling organism is by animal, plant and the composition of the microorganism, wherein harm kind large and that be difficult to remove is mainly stockless cirrus class (barnacle) and the bivalve (mussel and oyster) of tool calcium carbonate shell, battalion's set life.Therefore, the work of anti-fouling compound filler test is tested object mainly with stockless cirrus class and Bivalve.
At tropical littoral sea, reticulate pattern barnacle is the Typical Representative of stockless cirrus class, and is the kind having comparative advantage in fouling community; Perna viridis is the common bivalve in the East Sea and the South Sea, is to be also attached to important fouling organism kind on boats and ships, boat (floating) mark and aquaculture facility.Therefore, demonstration test of the present invention adopts reticulate pattern barnacle and Perna viridis as experimental subjects, and the achievement in research obtaining will have representative widely.
Fouling organism is divided into two life stages conventionally, till deviating from egg membrane and be developed to explore off and on body surface and prepare settlement and metamorphosis, is the life stage that swims from larva; Once larva is chosen, settling down position, adherance surface attachment, abnormal formation after the young, is set or epiphytism stage.From stained angle, it produces after harm starts from set or adhere to the mankind.If effectively suppress the settlement and metamorphosis of larva, just can reach the object of preventing and kill off.Therefore, it is the anti-fouling effect that experimental subjects is checked compound that the present invention adopts the halobiontic larva of this two class, has scientific rationality and representative meaning.
Understand fully that the antifouling mechanism of action of marine organisms native chemical can be the nuisanceless anti-soil technology of exploitation and offers reference, and marine organisms itself should be also the important sources of novel antifouling agent.Content based on related substances in marine organism is fewer, and structure relative complex, is not easy to deep exploitation and extensive use.Therefore large from stock number, be convenient to find natural anti-fouling agent in the terrestrial plant of growing and cultivation, be not only a kind of brand-new trial, and there is important theory and realistic meaning.
Chalcone be molecule amount less, there is benzchromones mother nucleus structure, be distributed widely in the compound in plant, it has the biologically actives such as anti-oxidant, antitumor, antibiotic and insecticidal action, yet, in preventing and removing marine fouling organisms field, have no any and disclosed its anti-adhewsive action and used it for fouling organism and prevent and kill off aspect about reporting.
17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone, its molecular formula is C
18h
14o
4molecular weight is 294, chemical structural formula is suc as formula shown in (I), this compound is first disclosed as succinctly, separation and the crystal structure [J] of the refined .17-methoxyl group-7-of Huang Ren hydroxyl-benzofuran chalcone (being 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone of the present invention). Agriculture of Anhui science, 2011,39 (15): 8920-8921,8993.
Formula (I).
Summary of the invention:
The object of this invention is to provide the application of 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone in preparing preventing and removing marine fouling organisms agent.
17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone of the present invention is 0.1 μ g/cm at coated weight<sup TranNum="75">2</sup>when above, adhering to of kentrogon produced to obvious inhibitory action.Its preferred coated weight is 0.1～1 μ g/cm<sup TranNum="76">2</sup>.Test shows, in the scope of this Dosages under, 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone does not have obvious toxicity to kentrogon.17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone is being 1 μ g/cm at coated weight<sup TranNum="77">2</sup>time, the adhesive rate of Mytilus Edulis Larva is only 6.0%, well below control group, difference is (p<0.01) extremely significantly, shows that 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone can suppress adhering to of Perna viridis larva effectively.17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone is to the good inhibitory action of being attached with of cirrus class and Bivalve as can be seen here.
Therefore, the invention provides the application of 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone in preparing preventing and removing marine fouling organisms agent.
Described preventing and removing marine fouling organisms agent is preferably kentrogon agent for preventing and eliminating or Mytilus Edulis Larva agent for preventing and eliminating.
Compared with prior art, the present invention has following beneficial effect:
17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone of the present invention is when low dosage is coated on the surface of solids, and the effect that has obvious inhibition marine organisms to adhere to, therefore can be used in and prepare preventing and removing marine fouling organisms agent.And 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone is naturally occurring organic compound, can polluted-water environment and cause its enrichment in organism by food chain transmission, environmentally friendly, safe, when effectively inhibition marine organisms adhere to, the heavy metal element such as cupric and tin not, from environmental protection angle, there is good social benefit, and it is easy that approach is prepared in its separation of 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone, be suitable for large-scale production, apply potentiality large, in preventing and removing marine fouling organisms, have a good application prospect.
Embodiment:
Following examples are to further illustrate of the present invention, rather than limitation of the present invention.
Embodiment 1:
Experimental group I: 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone is dissolved with chloroform, and compound concentration is the solution of 28.26 μ g/ml.In the culture dish that is 6cm at diameter, add this solution of 1ml, and make its uniform fold culture dish bottom.After solvent volatilizees completely, the content that is coated on 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone of culture dish bottom is 1 μ g/cm
2.Add 10ml seawater.
Experimental group II: 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone is dissolved with chloroform, and compound concentration is the solution of 2.826 μ g/ml.In the culture dish that is 6cm at diameter, add this solution of 1ml, and make its uniform fold culture dish bottom.After solvent volatilizees completely, the 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone content that is coated on culture dish bottom is 0.1 μ g/cm
2.Add 10ml seawater.
Control group: add 1ml chloroform, make it be uniformly distributed in culture dish bottom, treat that volatilization adds 10ml seawater completely again.
Blank group: add 10ml seawater.
Experimental group, blank group and control group are respectively established 5 Duplicate Samples.In each sample, add respectively 30 reticulate pattern barnacle cyprids.Be placed in temperature and be in the constant incubator of 29 ℃ of left and right and cultivate in dark surrounds.Every 24 hours, observe once.Cultivate after 72 hours final the adhering to death state of each group larva carried out to statistical analysis.
Table 1 has been listed adhering to and lethality of experimental group, control group and blank group cyprids.Visible, in constant incubator, cultivate 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 is without significant difference (p > 0.05), show can not leave over the harmful substance that affects cyprids activity after the chloroform volatilization as solvent, be suitable for dissolving this compound.As for the experimental group of processing through 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone, the adhesive rate of its cyprids, lower than 25%, is far smaller than control group, and difference extremely significantly (p < 0.01); In addition, the larval mortality of blank group, control group and experimental group is 0, shows that this compound can suppress adhering to of reticulate pattern barnacle cyprids effectively and this dosage can not produce toxic action to larva.
Table 1: reticulate pattern barnacle cyprids attachment
| Group | Proof load | Adhesive rate (%) | Lethality (%) |
| Blank group | － | 85.0 | 0 |
| Control group | － | 83.0 | 0 |
| Experimental group I | 1μg/cm 2 | 21.0 | 0 |
| Experimental group II | 0.1μg/cm 2 | 19.0 | 0 |
Embodiment 2
Experimental group: 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone is dissolved with chloroform, and compound concentration is the solution of 28.26 μ g/ml.In the culture dish that is 6cm at diameter, add this solution of 1ml and make its uniform fold culture dish bottom.After solvent volatilizees completely, the 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone content that is coated on culture dish bottom is 1.0 μ g/cm
2.Add 10ml seawater.
Control group: add 1ml chloroform, make solution be uniformly distributed in culture dish bottom, treat that solvent evaporates is complete, then add 10ml seawater.
Blank group: add 10ml seawater.
Determining of larva quantity: get containing the water body of Perna viridis veliger and concentrate with bolting silk from nursery pond.Minute respectively get 50ml three times, splash into 1-2 and drip after formalin solution kills larva and count under microscope, averaging of income value is the density of larva in water body.
Experimental group, blank group and control group are all established 5 Duplicate Samples, add approximately 30 larvas in each sample.In being about the incubator of 26 ℃, temperature cultivates under dark surrounds.Every 24 hours, observe once.Cultivate after 72 hours final the adhering to death state of each group larva carried out to statistical analysis.
Table 2 has been listed adhering to and lethality of experimental group, control group and blank group Perna viridis larva.Visible, in constant incubator, cultivate after 72 hours, the larva adhesive rate of blank group is about 30%, control group approximately 31%, the adhesive rate of blank group and control group veliger is without significant difference (p > 0.05), show can not leave over the harmful substance that affects veliger activity after the chloroform volatilization as solvent, be suitable for dissolving this compound.And the experimental group of processing through 17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone, the adhesive rate of its larva is only 6.0%, well below control group, difference is (p < 0.01) extremely significantly, shows that this compound can suppress adhering to of Perna viridis larva effectively.
Table 2: Perna viridis veliger attachment
| Group | Proof load | Adhesive rate % | Lethality % |
| Blank group | － | 30.0 | 0 |
| Control group | － | 31.2 | 0 |
| Experimental group | 1.0μg/cm 2 | 6.0 | 0 |
Claims (2)
- The application of 1.17-oxygen methyl-7-hydroxyl-benzene-furans-chalcone in preparing preventing and removing marine fouling organisms agent, described 17-oxygen firstThe structural formula of base-7-hydroxyl-benzene-furans-chalcone is suc as formula shown in (I):
Formula (I). - 2. application according to claim 1, is characterized in that, described preventing and removing marine fouling organisms agent is that kentrogon is prevented and kill offAgent or Mytilus Edulis Larva agent for preventing and eliminating.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279082A (en) * | 2016-08-02 | 2017-01-04 | 浙江大学 | Substituted furan chalcone derivant and preparation method thereof |
| CN111937875A (en) * | 2020-08-07 | 2020-11-17 | 中国科学院南海海洋研究所 | Application of tetrahydroanthraquinone compound in preparation of marine fouling organism control agent |
Citations (4)
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| CA2029263C (en) * | 1989-11-10 | 1995-09-05 | Mayara Easwaran Narayanan Nambudiry | Cosmetic composition |
| JP2001064294A (en) * | 1999-08-30 | 2001-03-13 | Pola Chem Ind Inc | Pongamor glucoside and preparation for external use for skin containing the same |
| CN102617529A (en) * | 2012-02-27 | 2012-08-01 | 云南民族大学 | Application for isobenzofuran type compounds in marine biofouling prevention and preparation method thereof |
| CN102775870A (en) * | 2012-06-14 | 2012-11-14 | 天长市银狐漆业有限公司 | Biocidal antifouling paint |
-
2013
- 2013-10-22 CN CN201310499561.6A patent/CN103518722B/en active Active
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA2029263C (en) * | 1989-11-10 | 1995-09-05 | Mayara Easwaran Narayanan Nambudiry | Cosmetic composition |
| JP2001064294A (en) * | 1999-08-30 | 2001-03-13 | Pola Chem Ind Inc | Pongamor glucoside and preparation for external use for skin containing the same |
| CN102617529A (en) * | 2012-02-27 | 2012-08-01 | 云南民族大学 | Application for isobenzofuran type compounds in marine biofouling prevention and preparation method thereof |
| CN102775870A (en) * | 2012-06-14 | 2012-11-14 | 天长市银狐漆业有限公司 | Biocidal antifouling paint |
Non-Patent Citations (2)
| Title |
|---|
| PREM P Y ET AL: "An efficient route for commercially viable syntheses of furan- and thiophene-annelated β-hydroxychalcones", 《TETRAHEDRON LETTERS》, no. 46, 7 July 2005 (2005-07-07), pages 5621 - 5624 * |
| 简洁等: "17-甲氧基-7-羟基-苯并呋喃查尔酮的分离及晶体结构", 《安徽农业科学》, vol. 39, no. 15, 31 December 2011 (2011-12-31) * |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN106279082A (en) * | 2016-08-02 | 2017-01-04 | 浙江大学 | Substituted furan chalcone derivant and preparation method thereof |
| CN106279082B (en) * | 2016-08-02 | 2019-02-01 | 浙江大学 | Substituted furans chalcone derivative and preparation method thereof |
| CN111937875A (en) * | 2020-08-07 | 2020-11-17 | 中国科学院南海海洋研究所 | Application of tetrahydroanthraquinone compound in preparation of marine fouling organism control agent |
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