CN111937875A - Application of tetrahydroanthraquinone compound in preparation of marine fouling organism control agent - Google Patents
Application of tetrahydroanthraquinone compound in preparation of marine fouling organism control agent Download PDFInfo
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- CN111937875A CN111937875A CN202010789905.7A CN202010789905A CN111937875A CN 111937875 A CN111937875 A CN 111937875A CN 202010789905 A CN202010789905 A CN 202010789905A CN 111937875 A CN111937875 A CN 111937875A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N35/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical
- A01N35/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having two bonds to hetero atoms with at the most one bond to halogen, e.g. aldehyde radical containing keto or thioketo groups as part of a ring, e.g. cyclohexanone, quinone; Derivatives thereof, e.g. ketals
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Abstract
The invention discloses application of tetrahydroanthraquinone compounds in preparation of marine fouling organism control agents, wherein the structural formula of the tetrahydroanthraquinone compounds is shown as a formula (I). The tetrahydroanthraquinone compound has obvious effect of inhibiting marine organism adhesion when being coated on a solid surface at low dose, so that the tetrahydroanthraquinone compound can be used for preparing marine fouling organism control agents. The marine biofouling inhibitor is a naturally-occurring organic compound, does not pollute the water environment and cause the enrichment of the marine biofouling inhibitor in organisms through food chain transfer, is environment-friendly and high in safety, does not contain heavy metal elements such as copper and tin while effectively inhibiting the attachment of marine organisms, has good social benefits from the aspect of environmental protection, has large popularization and application potentials, and has good application prospects in the prevention and removal of marine biofouling organisms.
Description
The technical field is as follows:
the invention belongs to the field of natural products, and particularly relates to an application of tetrahydroanthraquinone compounds in preparation of marine fouling organism control agents.
Background art:
the marine fouling organisms refer to various organisms fixed or inhabiting underwater parts of ships and marine facilities, and the harm caused by the marine fouling organisms is mainly to increase resistance, reduce navigational speed, increase fuel consumption and CO2Discharging; blocking a seawater pipeline system, changing a metal corrosion process, and initiating local corrosion or perforation corrosion; the dynamic load effect is increased, so that the drift, unbalance and even overturn of the facility are caused; compete with the cultured objects (such as shellfish) for the attachment base and the bait, hinder the growth and development of the cultured objects and reduce the quality of the products.
The antifouling paint is one of the most widely applied technical methods in preventing and removing marine fouling organisms. However, the traditional antifouling paint takes poison release as a main way, inhibits the attachment of fouling organisms through poisoning action, has the defects of high toxicity, short effective period and the like, and the released antifouling agent also has the risk of harming the marine ecological environment, so that the development of a novel, efficient, low-toxicity and environment-friendly antifouling agent becomes a problem and a research hotspot which are urgently needed to be solved at present.
Since marine fouling organisms are composed of animals, plants and microorganisms, the more harmful and difficult to remove species are mainly limy hulls, sessile stemless vines (barnacles) and bivalve mollusks (mussels and oysters). Therefore, screening tests for antifouling compounds have mostly been performed on stemless vines and bivalves.
In tropical coastal waters, balanus reticulatus is a typical representative of sessile tendrils and is an absolutely dominant species in the biofouling organism community; perna viridis is a common bivalve mollusk in the east and south seas, and is also an important fouling organism species attached to ships, navigations (buoys) and aquaculture facilities. Therefore, the verification test of the invention adopts the balanus reticulates and the perna viridis as experimental objects, and the obtained research results have wide representativeness.
Fouling organisms are generally divided into two life stages, namely a planktonic life stage from the development of larva out of an egg membrane to the intermittent exploration of the surface of an object to prepare for attachment and metamorphosis; once the larvae are selected to be in the settlement position, the larvae are attached to the surface of the attachment base and transformed into larvae, and then the larvae are in the fixation or attachment life stage. From an insult point of view, it begins after fixation or attachment to humans. If the settlement and metamorphosis of the larvae can be effectively inhibited, the purpose of preventing and removing can be achieved. Therefore, the invention adopts the larvae of the two types of marine organisms as experimental objects to test the antifouling effect of the compound, and has scientific reasonability and representative significance.
The clarification of the natural chemical antifouling mechanism of marine organisms can provide reference for developing pollution-free antifouling technology, and the marine organisms themselves are important sources of novel antifouling agents. The content of relevant substances in marine organisms is low, and the structure is relatively complex, so that the marine organism is inconvenient to deeply develop and widely apply. Therefore, the natural antifouling agent is searched from terrestrial plants which have large resource quantity and are convenient for planting and cultivation, and the natural antifouling agent is not only a brand new attempt, but also has important theoretical and practical significance.
The tetrahydroanthraquinone compound is named as (5S,6R,7S) -5,6,7,9, 10-hydroxy-2-methoxy-7-methyl-5, 6,7, 8-tetrahydroanthracene-1, 4-dione, the English name is (5S,6R,7S) -5,6,7,9,10-pentahydroxy-2-methoxy-7-methyl-5,6,7, 8-tetrahydroanthraquinone-1, 4-dione, and red powder is separated from a mangrove endophytic fungus Halarosellinia sp. The molecular formula is C16H16O8The molecular weight is 336, and the chemical structural formula is shown as a formula (I).
The structure of the compound has been reported (Jiangkuang, Zhoushanning, research on secondary metabolite of endophytic fungus No.1403 of south China sea mangrove, university of Zhongshan (Nature science edition), 2000,39(006):68-72.), and the compound can cause the leaf necrosis of plants such as water hyacinth, can inhibit gram-positive bacteria and has better anti-tumor activity, but in the field of preventing and controlling marine fouling organisms, no report on the anti-marine fouling organism adhesion effect and the application of the anti-marine fouling organism adhesion effect in the field of preventing and controlling the fouling organisms is found.
The invention content is as follows:
the invention aims to provide application of tetrahydroanthraquinone compounds in preparation of marine fouling organism control agents.
The coating amount of the tetrahydroanthraquinone compound is 10 mu g/cm2When compared with the control group, the compound has obvious inhibition effect on the attachment of barnacle larvae (p)<0.05). The preferred coating amount is 10. mu.g/cm2. Moreover, experiments show that the tetrahydroanthraquinone compound has no obvious toxicity to barnacle larvae under the action dosage. The coating amount of the tetrahydroanthraquinone compound is 1.0 mu g/cm2In time, the attachment rate of mussel larvae is far lower than that of the control group, and the difference is obvious (p)<0.05), indicating that the compound is effective in inhibiting the attachment of perna viridis larvae. Therefore, the tetrahydroanthraquinone compound has good inhibition effect on the adhesion of the tendrils and the bivalves.
Therefore, the invention provides an application of tetrahydroanthraquinone compounds in preparing marine fouling organism control agents, wherein the structural formula of the tetrahydroanthraquinone compounds is shown as the formula (I):
the marine biofouling organism control agent is preferably a barnacle larva control agent (such as a balanus reticulatus larva control agent) or a mussel larva control agent (such as a perna viridis epidermoid larva control agent).
Compared with the prior art, the invention has the following beneficial effects:
the tetrahydroanthraquinone compound has obvious effect of inhibiting marine organism adhesion when being coated on a solid surface at low dose, so that the tetrahydroanthraquinone compound can be used for preparing marine fouling organism control agents. The tetrahydro anthraquinone compound is a naturally-occurring organic compound, does not pollute the water environment and cause the enrichment of the tetrahydro anthraquinone compound in organisms through food chain transmission, is environment-friendly and high in safety, does not contain heavy metal elements such as copper and tin while effectively inhibiting the attachment of marine organisms, has good social benefits from the aspect of environmental protection, has large popularization and application potentials, and has good application prospects in marine fouling organism prevention and removal.
The specific implementation mode is as follows:
the following examples are further illustrative of the present invention and are not intended to be limiting thereof.
Example 1:
a quantitative amount of the tetrahydroanthraquinone was dissolved in methanol to give a solution having a concentration of 282.6. mu.g/mL, and 1mL of the solution was added to a 6 cm-diameter petri dish so as to uniformly cover the bottom of the dish. After the solvent is completely volatilized, the content of the tetrahydroanthraquinone compound coated at the bottom of the culture dish is 10 mu g/cm2. 13ml of filtered sterile seawater was added.
Control group: adding 1ml of solvent methanol to uniformly distribute the methanol at the bottom of the culture dish, and adding 13ml of filtered and sterilized seawater when the methanol is completely volatilized.
Blank group: 13ml of filtered sterile seawater was added.
Each of the experimental, blank and control groups was provided with 4 replicates. In the adhesion test process, barnacle larvae are randomly distributed to a blank group, a control group and an experimental group, about 30 larvae are placed in each parallel sample, and the sample is placed in a constant-temperature incubator at the temperature of 30 ℃ to be cultured in a dark environment. After 120 hours of culture, the number of attached larvae in each parallel sample was recorded, the attachment rate of larvae (number of attached larvae/number of inserted larvae) in each parallel sample was calculated, the average attachment rate of larvae in each group (i.e., blank group, control group, and experimental group) [ (attachment rate of parallel sample 1 + attachment rate of parallel sample 2 + attachment rate of parallel sample 3 + attachment rate of parallel sample 4)/4 ] was counted, and the significance of differences between groups was examined to confirm the effect of the related compound in inhibiting the attachment of pot larvae. The adhesion rate calculation method of example 2 was also calculated with reference to this method.
Table 1 lists the attachment and mortality rates of the cyprids of the experimental, control and blank groups. It can be seen that, after 120 hours of culture in the incubator, the attachment rate of larvae of the blank group is 37.5%, that of larvae of the control group is 37.1%, and that there is no significant difference (p >0.05) between the attachment rates of larvae of Venus asiatica of the blank group and the control group, indicating that no harmful substance affecting the activity of larvae of Venus asiatica is left after the methanol as the solvent is volatilized, and the compound is suitable for dissolving the compound. As for the experimental group treated by the tetrahydroanthraquinone compound, the attachment rate of the cyprids of the avenae is 24.5 percent, which is lower than that of the control group, and the difference is obvious (p is less than 0.05); in addition, the larval mortality rates of the blank group, the control group and the experimental group are all 0, which indicates that the compound can effectively inhibit the attachment of cyprids of balanus reticulatus and the dosage does not have toxic effect on the larvas.
Table 1: attachment status of cyprids of balanus reticulates
| Group of | Test dose | Adhesion Rate (%) | Mortality (%) |
| Blank group | － | 37.5 | 0 |
| Control group | － | 37.1 | 0 |
| Experimental group | 10μg/cm2 | 24.5 | 0 |
Example 2
Experimental groups: dissolving the tetrahydroanthraquinone compound with methanol to prepare a solution with the concentration of the tetrahydroanthraquinone compound being 28.26 mu g/mL. 1mL of this solution was added to a 6cm diameter dish and allowed to cover the bottom of the dish uniformly. After the solvent is completely volatilized, the content of the tetrahydroanthraquinone compound coated at the bottom of the culture dish is 1.0 mu g/cm2. 13mL of filtered sterile seawater was added.
Control group: adding 1mL of solvent methanol to uniformly distribute the solution at the bottom of the culture dish, and adding 13mL of filtered and sterilized seawater when the solvent is completely volatilized.
Blank group: 13mL of filtered sterile seawater was added.
Determination of the number of larvae: taking water containing perna viridis facial disc larvae from the nursery pond and concentrating by bolting silk. Taking 50mL of the water body after three times, dripping 1-2 drops of formalin solution to kill the larvae, and counting under a microscope to obtain an average value, namely the density of the larvae in the water body.
Experiment group, blank group and control group all establish 4 parallel appearance, absorb a certain amount of water that contains emerald mussel faceplates larva according to the density of larva in above-mentioned water for add about 30 larvae in each sample. Culturing in dark environment in an incubator at a temperature of about 26 ℃. Statistical analysis of the final attachment and death status of each group of larvae was performed after 72 hours of culture.
Table 2 lists the attachment and mortality rates of perna viridis larvae in the experimental, control and blank groups. It can be seen that, after the compound is cultured in the incubator for 72 hours, the attachment rate of the larvae of the blank group is 39.0%, the attachment rate of the larvae of the control group is 39.6%, and the attachment rates of the larvae of the dough plates of the blank group and the control group are not obviously different (p is more than 0.05), which indicates that the methanol used as the solvent does not leave harmful substances which affect the activity of the larvae of the dough plates after volatilization, and the compound is suitable for dissolving the compound. The experimental group treated by the tetrahydroanthraquinone compound has the larva attachment rate of 18.8 percent, and has obvious difference (p is less than 0.05) with the control group, which shows that the compound can effectively inhibit the attachment of the perna viridis larva.
Table 2: emerald mussel face plate larva attachment condition
| Group of | Test dose | Percentage of adhesion% | Mortality (%) |
| Blank group | － | 39.0 | 0 |
| Control group | － | 39.6 | 0 |
| Experimental group | 1.0μg/cm2 | 18.8 | 0 |
Claims (5)
1. The application of tetrahydroanthraquinone compounds in preparing marine fouling organism control agents is that the structural formula of the tetrahydroanthraquinone compounds is shown as the formula (I):
2. use according to claim 1, wherein the marine biofouling organism control agent is a barnacle larva control agent.
3. Use according to claim 2, wherein the barnacle larvae control agent is a balanus reticulatus avenae larvae control agent.
4. The use according to claim 1, wherein the marine biofouling organism control agent is a mussel larva control agent.
5. The use as claimed in claim 4, wherein the mussel larvae control agent is emerald mussel faceplates larvae control agent.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112694507A (en) * | 2020-12-31 | 2021-04-23 | 中山大学 | Tetrahydro anthraquinone glycoside compound and application thereof in preparation of antitumor drugs |
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| CN101416623A (en) * | 2000-02-17 | 2009-04-29 | 加尼特有限公司 | Method of controlling zoological and aquatic plant growth |
| CN101862314A (en) * | 2010-06-18 | 2010-10-20 | 中山大学 | Application of quinine compound in preparing anti-tubercle bacillus drugs |
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| CN101416623A (en) * | 2000-02-17 | 2009-04-29 | 加尼特有限公司 | Method of controlling zoological and aquatic plant growth |
| CN102482188A (en) * | 2009-05-29 | 2012-05-30 | 海洋生命学医药有限公司 | Novel anthraquinone derivatives |
| CN101862314A (en) * | 2010-06-18 | 2010-10-20 | 中山大学 | Application of quinine compound in preparing anti-tubercle bacillus drugs |
| CN103518722A (en) * | 2013-10-22 | 2014-01-22 | 中国科学院南海海洋研究所 | Application of 17-oxymethyl-7-hydroxy-benzene-furan-chalcone in preparing marine fouling organism control agent |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112694507A (en) * | 2020-12-31 | 2021-04-23 | 中山大学 | Tetrahydro anthraquinone glycoside compound and application thereof in preparation of antitumor drugs |
| CN112694507B (en) * | 2020-12-31 | 2022-03-29 | 中山大学 | Tetrahydro anthraquinone glycoside compound and application thereof in preparation of antitumor drugs |
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