CN108484628A - Application of the kusulactone class compound in preventing marine biofouling - Google Patents
Application of the kusulactone class compound in preventing marine biofouling Download PDFInfo
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- CN108484628A CN108484628A CN201810516542.2A CN201810516542A CN108484628A CN 108484628 A CN108484628 A CN 108484628A CN 201810516542 A CN201810516542 A CN 201810516542A CN 108484628 A CN108484628 A CN 108484628A
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- Prior art keywords
- kusulactone
- class compound
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- marine biofouling
- preventing marine
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- LTHDJUORLSBEHK-UHFFFAOYSA-N kusulactone Natural products C1C(C23C)OC(=O)CC3C(C)(OC(C)=O)C(OC(C)=O)C(O)C2C2(C)C1C(C)C=C(OC)C2=O LTHDJUORLSBEHK-UHFFFAOYSA-N 0.000 title claims abstract description 50
- ULPUGCMMDNWWLH-UHFFFAOYSA-N picraqualide B Natural products COC1=CC(C)C2CC3OC(=O)CC4C(C)(O)C(OC(=O)C)C(OC(=O)C)C(C34C)C2(C)C1=O ULPUGCMMDNWWLH-UHFFFAOYSA-N 0.000 title claims abstract description 50
- 150000001875 compounds Chemical class 0.000 title claims abstract description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 4
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 3
- 239000000284 extract Substances 0.000 claims description 36
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 18
- 230000003373 anti-fouling effect Effects 0.000 claims description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 239000000470 constituent Substances 0.000 claims description 15
- 235000010889 Rhus javanica Nutrition 0.000 claims description 14
- 235000013399 edible fruits Nutrition 0.000 claims description 14
- 238000010828 elution Methods 0.000 claims description 13
- 239000003973 paint Substances 0.000 claims description 11
- WORJEOGGNQDSOE-UHFFFAOYSA-N chloroform;methanol Chemical compound OC.ClC(Cl)Cl WORJEOGGNQDSOE-UHFFFAOYSA-N 0.000 claims description 10
- ZZZYHIMVKOHVIH-VILODJCFSA-N Brusatol Chemical compound CC1=C(O)C(=O)C[C@]2(C)[C@@H]([C@@H](O)[C@@H]3O)[C@@]45CO[C@@]3(C(=O)OC)[C@@H]5[C@@H](OC(=O)C=C(C)C)C(=O)O[C@@H]4C[C@H]21 ZZZYHIMVKOHVIH-VILODJCFSA-N 0.000 claims description 9
- ZZZYHIMVKOHVIH-UHFFFAOYSA-N Brusatol Natural products CC1=C(O)C(=O)CC2(C)C(C(O)C3O)C45COC3(C(=O)OC)C5C(OC(=O)C=C(C)C)C(=O)OC4CC21 ZZZYHIMVKOHVIH-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 7
- 238000000605 extraction Methods 0.000 claims description 7
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- 238000004440 column chromatography Methods 0.000 claims description 6
- 238000001514 detection method Methods 0.000 claims description 6
- 239000003208 petroleum Substances 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 238000010898 silica gel chromatography Methods 0.000 claims description 6
- 235000019441 ethanol Nutrition 0.000 claims description 5
- 239000004615 ingredient Substances 0.000 claims description 5
- 239000004925 Acrylic resin Substances 0.000 claims description 4
- 229920000178 Acrylic resin Polymers 0.000 claims description 4
- 241000158621 Brucea Species 0.000 claims description 4
- 239000002245 particle Substances 0.000 claims description 4
- 229920005749 polyurethane resin Polymers 0.000 claims description 4
- 229930002875 chlorophyll Natural products 0.000 claims description 3
- 235000019804 chlorophyll Nutrition 0.000 claims description 3
- ATNHDLDRLWWWCB-AENOIHSZSA-M chlorophyll a Chemical compound C1([C@@H](C(=O)OC)C(=O)C2=C3C)=C2N2C3=CC(C(CC)=C3C)=[N+]4C3=CC3=C(C=C)C(C)=C5N3[Mg-2]42[N+]2=C1[C@@H](CCC(=O)OC\C=C(/C)CCC[C@H](C)CCC[C@H](C)CCCC(C)C)[C@H](C)C2=C5 ATNHDLDRLWWWCB-AENOIHSZSA-M 0.000 claims description 3
- 239000003480 eluent Substances 0.000 claims description 3
- 238000003810 ethyl acetate extraction Methods 0.000 claims description 3
- GBMDVOWEEQVZKZ-UHFFFAOYSA-N methanol;hydrate Chemical compound O.OC GBMDVOWEEQVZKZ-UHFFFAOYSA-N 0.000 claims description 3
- XELZGAJCZANUQH-UHFFFAOYSA-N methyl 1-acetylthieno[3,2-c]pyrazole-5-carboxylate Chemical compound CC(=O)N1N=CC2=C1C=C(C(=O)OC)S2 XELZGAJCZANUQH-UHFFFAOYSA-N 0.000 claims description 3
- 238000001035 drying Methods 0.000 claims description 2
- 239000003822 epoxy resin Substances 0.000 claims description 2
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- 229920000647 polyepoxide Polymers 0.000 claims description 2
- 229920001225 polyester resin Polymers 0.000 claims description 2
- 239000004645 polyester resin Substances 0.000 claims description 2
- 238000001953 recrystallisation Methods 0.000 claims description 2
- 239000000741 silica gel Substances 0.000 claims description 2
- 229910002027 silica gel Inorganic materials 0.000 claims description 2
- 229960001866 silicon dioxide Drugs 0.000 claims description 2
- 239000000377 silicon dioxide Substances 0.000 claims description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims 3
- 241001533159 Brucea javanica Species 0.000 claims 1
- 125000004494 ethyl ester group Chemical group 0.000 claims 1
- 241000238586 Cirripedia Species 0.000 abstract description 15
- 230000002401 inhibitory effect Effects 0.000 abstract description 14
- 231100000252 nontoxic Toxicity 0.000 abstract description 6
- 230000003000 nontoxic effect Effects 0.000 abstract description 6
- 238000003912 environmental pollution Methods 0.000 abstract 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
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- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 4
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- 229940125782 compound 2 Drugs 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 4
- 239000012488 sample solution Substances 0.000 description 4
- 241000351387 Amphibalanus amphitrite Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000002519 antifouling agent Substances 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 230000006378 damage Effects 0.000 description 3
- 239000002024 ethyl acetate extract Substances 0.000 description 3
- 239000009969 fructus bruceae Substances 0.000 description 3
- 230000005764 inhibitory process Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
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- 229940126214 compound 3 Drugs 0.000 description 2
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- 238000011161 development Methods 0.000 description 2
- 238000007598 dipping method Methods 0.000 description 2
- 210000003608 fece Anatomy 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 238000007654 immersion Methods 0.000 description 2
- 239000010871 livestock manure Substances 0.000 description 2
- 238000005374 membrane filtration Methods 0.000 description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000012452 mother liquor Substances 0.000 description 2
- 239000013642 negative control Substances 0.000 description 2
- JUJWROOIHBZHMG-RALIUCGRSA-N pyridine-d5 Chemical compound [2H]C1=NC([2H])=C([2H])C([2H])=C1[2H] JUJWROOIHBZHMG-RALIUCGRSA-N 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000013535 sea water Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000003440 toxic substance Substances 0.000 description 2
- HBGPNLPABVUVKZ-POTXQNELSA-N (1r,3as,4s,5ar,5br,7r,7ar,11ar,11br,13as,13br)-4,7-dihydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1h-cyclopenta[a]chrysen-9-one Chemical compound C([C@@]12C)CC(=O)C(C)(C)[C@@H]1[C@H](O)C[C@]([C@]1(C)C[C@@H]3O)(C)[C@@H]2CC[C@H]1[C@@H]1[C@]3(C)CC[C@H]1C(=C)C HBGPNLPABVUVKZ-POTXQNELSA-N 0.000 description 1
- XOEFANNJIKAWGX-MQXBNGFTSA-N 10-((3,6-dihydro-6-oxo-2h-pyran-2-yl)hydroxymethyl)-4,5,8,9,10,11-hexahydro-4,8-dihydroxy-5-(1-hydroxyheptyl)-1h-cyclonona(1,2-c:5,6-c')difuran-1,3,6-trione Chemical compound C1([C@@H](O)C2CC3=C(C(OC3=O)=O)[C@@H](O)C(C3=C(C(OC3=O)O)C2)[C@@H](O)CCCCCC)CC=CC(=O)O1 XOEFANNJIKAWGX-MQXBNGFTSA-N 0.000 description 1
- PFRGGOIBYLYVKM-UHFFFAOYSA-N 15alpha-hydroxylup-20(29)-en-3-one Natural products CC(=C)C1CCC2(C)CC(O)C3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 PFRGGOIBYLYVKM-UHFFFAOYSA-N 0.000 description 1
- 238000001026 1H--1H correlation spectroscopy Methods 0.000 description 1
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000700670 Bryozoa Species 0.000 description 1
- 241001086210 Chaetoceros gracilis Species 0.000 description 1
- 241001137251 Corvidae Species 0.000 description 1
- 241001000394 Diaphania hyalinata Species 0.000 description 1
- 102000004190 Enzymes Human genes 0.000 description 1
- 108090000790 Enzymes Proteins 0.000 description 1
- LZKVXMYVBSNXER-YZPKDWIXSA-N Glaucarubin Chemical compound O[C@@H]([C@]1(C)[C@@H]23)[C@@H](O)C=C(C)[C@@H]1C[C@@H]1[C@@]43CO[C@@]2(O)[C@H](O)[C@H](C)[C@@H]4[C@@H](OC(=O)[C@@](C)(O)CC)C(=O)O1 LZKVXMYVBSNXER-YZPKDWIXSA-N 0.000 description 1
- 241001523601 Gyrodactylus Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000237536 Mytilus edulis Species 0.000 description 1
- 241000244206 Nematoda Species 0.000 description 1
- SOKRNBGSNZXYIO-UHFFFAOYSA-N Resinone Natural products CC(=C)C1CCC2(C)C(O)CC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 SOKRNBGSNZXYIO-UHFFFAOYSA-N 0.000 description 1
- 208000002474 Tinea Diseases 0.000 description 1
- 241001500087 Trichodina Species 0.000 description 1
- 241000893966 Trichophyton verrucosum Species 0.000 description 1
- 241000196252 Ulva Species 0.000 description 1
- 241000196251 Ulva arasakii Species 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 230000008827 biological function Effects 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000003628 erosive effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 239000000469 ethanolic extract Substances 0.000 description 1
- 239000002038 ethyl acetate fraction Substances 0.000 description 1
- 230000006870 function Effects 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 238000003919 heteronuclear multiple bond coherence Methods 0.000 description 1
- 238000005570 heteronuclear single quantum coherence Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000011031 large-scale manufacturing process Methods 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 244000144972 livestock Species 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 230000035800 maturation Effects 0.000 description 1
- 230000010534 mechanism of action Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- AICOOMRHRUFYCM-ZRRPKQBOSA-N oxazine, 1 Chemical compound C([C@@H]1[C@H](C(C[C@]2(C)[C@@H]([C@H](C)N(C)C)[C@H](O)C[C@]21C)=O)CC1=CC2)C[C@H]1[C@@]1(C)[C@H]2N=C(C(C)C)OC1 AICOOMRHRUFYCM-ZRRPKQBOSA-N 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
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- 150000002989 phenols Chemical class 0.000 description 1
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- 230000008569 process Effects 0.000 description 1
- 229930182490 saponin Natural products 0.000 description 1
- 150000007949 saponins Chemical class 0.000 description 1
- 235000017709 saponins Nutrition 0.000 description 1
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- 125000001424 substituent group Chemical group 0.000 description 1
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- 150000003505 terpenes Chemical class 0.000 description 1
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- 231100000419 toxicity Toxicity 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
- C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
- C07D493/10—Spiro-condensed systems
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
Abstract
The present invention provides application of the kusulactone class compound in preventing marine biofouling, is related to biotechnology.The structural formula of the kusulactone class compound is formula I, in formula I, R1,R2,R3,R4It is respectively selected from " H " or " OH " or " CH3" or " COOR' " or " OOCR " ", wherein R' is " H " or " CH3", R " is the aliphatic chain that carbon atom number is 3~7.The kusulactone class compound has stronger inhibiting effect to marine fouling organism especially barnacle class biology, and be nontoxic natural active compound, it can effectively degrade in water body environment, environmental pollution will not be caused, with environmental-friendly, safe feature.
Description
Technical field
The present invention relates to biotechnologies, and in particular to kusulactone class compound is in preventing marine biofouling
Using.
Background technology
Marine fouling organism is to being grown in the marine animal of ship and various artificial ocean facilities surface, plant and micro-
There is the general name of biology the representative kind that serious attachment influences to have bacterium, diatom, Enteromorpha, sea lettuce, barnacle, mussel, bryozoan
Deng.The mass propagation of fouling organism can cause great harm ship and other artificial ocean facilities, for example increase ship boat
Row resistance blocks pipeline, accelerates metal erosion, making instrument and engine failure, threat aquaculture etc. in ocean, to mankind ocean
Economic activity brings many unfavorable.The harm that marine fouling organism brings leads to huge to industries such as sea transport, aquacultures
Economic loss, the whole world be up to nearly 10,000,000,000 dollars by the economic loss caused by marine biofouling every year.
Since natural anti-fouling agent (natural product antifoulants, NPAs) being found from the eighties in last century,
Natural products is always the important sources for finding novel fouling resistance agent (or active lead compound), has chemical constitution various,
The few advantage of mechanism of action too many levels, toxic side effect.Currently, the NPAs found from ocean and terrestrial life is mainly included
Terpenes, steroidal, phenols, halide, saponins, the nitrogenous compound etc. based on amino acid derivativges.Because of marine organisms institute
There are the marine natural products of generation its specific ecological functions, the fouling resistance that scientific research personnel once tends to find marine source to live
Property natural products, but due to the materials of marine organisms are inconvenient or limited by culture technique, active material ingredients content is extremely low and
It is difficult to realize be commercialized a large amount of supplies, the commercial development utilization for eventually leading to the later stage is had difficulty in taking a step.Develop novel antifouling agent most
Big challenge is exactly long-term, sustainably provides a large amount of natural anti-fouling activity substance, and really realizes commercialization hair at present
The Marine Natural Product Antifoulants agent of exhibition is few, much cannot be satisfied Vehicles Collected from Market to the urgent of cheap novel fouling resistance agent
Demand.Therefore, under the requirement for meeting sustainable development, it is found that it is environmental-friendly more broad-spectrum high efficacies, property are stable, yield is high
Type NPAs has special importance and urgency, and the terrestrial plant of abundance is due to its distinctive biological function and enzyme work(
Can, it can also be used as the important sources of exploitation NPAs.
China has abundant plant resources, common pesticide plant also to have nearly 500 kinds, non-toxic or low-toxic to find
NPAs provides abundant material base.Java brucea (Bruceajavanica) is Simarubaceae brucea plant, and one kind has
Significantly antitumor and insecticidal action frequently seen plants, have large area plantation under the economic forest of Guangxi province, there is up to ten thousand tons of crows every year
Courage is only used as under green manure feedback economic forest due to unsalable, and local abundant Java brucea resource cannot be applied adequately.Application
People has found that the characteristic component in Java brucea is kusulactone by research, is a kind of drop triterpene compound, usually with five rings or
Fourth Ring C20 type mother nucleus structures are most commonly seen, because the bioactivity that the variability of its structure assigns Java brucea kusulactone ingredient is more
Sample shows the effect for inhibiting to adhere to marine fouling organism, is especially apparent to the tachment inhibiting of barnacle class biology.Application number
For the Chinese patent of CN201610950469.0, publication date 2016.10.27 discloses a kind of Fructus Bruceae extract, extracting method
And application, it is indicated that Fructus Bruceae extract is to the inhibiting effect of nematode, to have higher antitumor activity.Application No. is
The Chinese patent of CN02139390.7, publication date 20030416 disclose a kind of aquatic livestock parasite control agent, it is indicated that crow courage
Seed extract has good inhibiting effect to Trichodina, small melonworm, ring worm and Gyrodactylus etc..But it does not point out to barnacle
The inhibiting effect of class biology, and not yet explicitly specific effective active composition in extract.
Invention content
The goal of the invention of the present invention is to prevent marine organisms dirty in view of the above-mentioned problems, providing kusulactone class compound
Application in damage, kusulactone class compound play the role of stronger inhibition marine fouling organism, especially to barnacle class biology
With good inhibiting effect, and it is the non-toxic compound of natural safety, can effectively degrades in water body environment, ring will not be caused
Border is polluted, and has environmental-friendly, safe feature.
In order to achieve the above objectives, the technical solution adopted in the present invention is：
Application of the kusulactone class compound in preventing marine biofouling, the structure of the kusulactone class compound
Formula is formula I：
In formula I, R1,R2,R3,R4It is respectively selected from "-H " or "-OH " or "-CH3" or "-COOR' " or "-OOCR " ", wherein
R' is "-H " or "-CH3", R " is the aliphatic chain that carbon atom number is 3~7.
Preferably, the kusulactone class compound is one kind or two in Brusatol, crow courage bitter principle J, crow courage bitter principle D
Kind or more, the Brusatol, crow courage bitter principle J, crow courage bitter principle D structural formula see II-formula of formula IV：
Preferably, the kusulactone class compound is extracted from brucea plant.
Preferably, the kusulactone class compound is extracted from the root of Java brucea, stem, leaf or fruit.
Preferably, the extracting method of the kusulactone class compound includes the following steps：
S1. fruit of khosam and drying, crushing are chosen, fruit particle is obtained；Then the fruit particle is soaked with ethyl alcohol
Bubble, extraction, obtain extracting solution
S2. the extracting solution is filtered, medicinal extract is concentrated under reduced pressure to obtain；The medicinal extract is dispersed in water, uses petroleum ether successively,
Ethyl acetate and n-butanol are extracted, are concentrated in vacuo extract liquor, and petroleum ether extraction medicinal extract, ethyl acetate extraction are respectively obtained
Medicinal extract and extracting n-butyl alcohol medicinal extract.
S3. thin through TLC with chloroform-methanol gradient elution by ethyl acetate extraction medicinal extract through normal-phase silica gel column chromatography
The identical flow point of analysis combining data detection principal point layer by layer, obtains E1-E11Totally 11 components.
S4. by the component E5Through normal-phase silica gel column chromatography, with chloroform-methanol gradient elution, combining data detection same principle point
Flow point obtains E5-1~E5-6Totally six subfractions；By the subfraction E5-6Recrystallization, is eluted with methanol, obtains Brusatol.
S5. by the E9MCI column chromatographies are pressed in, and chlorophyll is removed simultaneously with 30%~100% methanol-water gradient elution
Obtain E9-1~E9-10Totally 10 subfractions, by the subfraction E9-4Through Sephadex LH-20 column chromatographies, methanol is eluant, eluent,
Obtain crow courage bitter principle J.
S6. by the subfraction E9-8Through being recrystallized to give crow courage bitter principle D.
Preferably, in step S2 and S3, the normal phase silicagel column uses 200~300 mesh silica fillers.
Preferably, in step S3, chloroform-methanol by volume 95:5-40:60 ratio elution；In step S4, chloroform-
Methanol by volume 95:5-80:20 ratio elution.
Preferably, antifouling paint is prepared using the kusulactone class compound.
Preferably, the antifouling paint includes anti-pollution active constituent and film forming component, the addition of the anti-pollution active constituent
Amount is the 0.5%~25% of the weight of film forming component；The anti-pollution active constituent is the kusulactone class chemical combination that structural formula is formula I
Object；The film forming component is hydrolysable resins, soluble resin or insoluble resin.
Preferably, the film forming component be acrylic resin, epoxy resin, polyester resin, polyurethane resin one kind or
It is two or more.
Due to the adoption of the above technical scheme, the invention has the advantages that：
1. application of the kusulactone class compound of the present invention in preventing marine biofouling, kusulactone class compound
There is stronger inhibiting effect to marine fouling organism, especially there is good inhibiting effect to barnacle class biology, and as day
So existing organic compound, is non-toxic compound, can effectively degrade in the natural environment, will not cause water body environment pollution,
With environmental-friendly, safe feature.
2. application of the kusulactone class compound of the present invention in preventing marine biofouling, the kusulactone class
Close object, be method track by bioactivity, from Java brucea separation identify, be the main component in Java brucea,
It obtains maturation simple for process, and the plant has large area plantation under the economic forest of Guangxi province, there is up to ten thousand tons of crow courage every year
Son is only used as under green manure feedback economic forest due to unsalable, is suitble to large-scale production, has reliable and stable source, is promoted and applied latent
Power is big.
3. application of the kusulactone class compound of the present invention in preventing marine biofouling, kusulactone class compound exhibition
Reveal stronger inhibition marine biofouling activity, guide's chemical combination can be provided for the exploitation of antifouling paint or other fouling resistance products
Object has good application prospect.
Specific implementation mode
In order to make the purpose , technical scheme and advantage of the present invention be clearer, with reference to embodiments, to the present invention
It is further elaborated.It should be appreciated that the specific embodiments described herein are merely illustrative of the present invention, it is not used to
Limit the present invention.
Embodiment 1
Experimental verification：The inhibitory activity that Java brucea crude extract adheres to line kentrogon
Material source：Fruit of khosam is adopted in Guangxi, is accredited as through Guangxi University associate professor Ma Zhonghui
Bruceajavanica, Saving specimen is in Guangxi University of Chinese Medicine's scientific tcm experimental center.
The preparation of Fructus Bruceae extract：After dry fruit of khosam is crushed four are extracted with 95% alcohol solution dipping
It is secondary, first time 5d, after 3d three times, extracting solution is concentrated under reduced pressure without ethanol extract after merging.Add water at suspension, uses oil successively
Ether, ethyl acetate and extracting n-butyl alcohol, are concentrated to dryness to obtain petroleum ether extraction medicinal extract, and ethyl acetate extracts medicinal extract, n-butanol
Medicinal extract is extracted, it is spare that water extracts medicinal extract.
Using the different portions for inhibiting the experimental model of line barnacle cyprids attachment to test brucea plant Java brucea
Position extract inhibits the ability of kentrogon attachment.Line barnacle (Balanus amphitrite) adult picks up from Guangxi Beilun Estuary
On the mangrove trunk of mangrove swamps protected area.
Specific cultural method is as follows：It is fed with diatom at 28 DEG C after obtaining barnacle naupiar larva, is developed to after about 4d
The cyprids stage.Cyprids are filtered and are stored in the seawater of 0.22 μm of membrane filtration, 4 DEG C of refrigerator overnights is placed in and waits for
With.Sample to be tested is configured to the mother liquor of 10mg/mL with DMSO, is then configured to the use of various concentration sample to be tested again.By 24 holes
1mL testing sample solutions are placed in each hole in plate, and each testing sample solution includes 3 repetitions, then by 15 kentrogons
It is lightly transferred in each hole containing solution to be measured and is tested.1 μ L DMSO are added in the filtering sea of 1mL, per hole
15 larvas are put as negative control.It is bright that 24 orifice plates handled well are placed on 15h in 28 DEG C of incubators：9h light cultures 48h.It waits training
After supporting, 24 orifice plates are placed in microscopically observation, and record the larva number of travelling, attachment and death.The larva of attachment
Number and total larva number ratio are adhesive rate.The ratio of dead larvae number and total larva number is the death rate, and ratio is used respectively
Percentage indicates.Each sample tests 3 repetitions under each concentration.It is analyzed by Probit softwares and calculates EC50And LC50, knot
Fruit is shown in Table 1.
Anti-fouling activity and toxicity assessment of the 1. Java brucea different parts extract of table to line barnacle (B.amphitrite)
The present embodiment has carried out anti-marine fouling organism larva attachment to fruit of khosam alcohol extract and each extraction position and has lived
Property Preliminary Determination, the results show that the crude extract of different parts to selected marine fouling organism represent line kentrogon have difference
The inhibiting effect of degree, wherein the anti-fouling activity with ethyl acetate extract is best.As seen from the results in Table 1, organic phase position
EC50Value is most of to be both less than the fixed natural anti-fouling agent standard (EC of USN50≤ 25 μ g/mL), and EC50Value is below LC50
Value shows to can be used as anti-containing low toxicity or nontoxic anti-line kentrogon attachment activity substance, announcement Java brucea in extract
The efficient resource for controlling marine fouling organism further is developed and used.The especially anti-fouling activity of Ethyl acetate fraction
Highest.
Embodiment 2 detaches the kusulactone class compound for preventing marine biofouling from fruit of khosam
The extracting method of the kusulactone class compound includes the following steps：
S1. it is extracted four times with 95% alcohol solution dipping after dry fruit of khosam being crushed, for the first time immersion 5d, rear three
Secondary each immersion 3d merges 4 extracting solutions.
S2. medicinal extract is concentrated under reduced pressure to obtain in the extracting solution after merging.Add water at suspension the medicinal extract, uses oil successively
Ether, ethyl acetate and extracting n-butyl alcohol, are concentrated to dryness to obtain petroleum ether extraction medicinal extract (138.8g), and ethyl acetate extracts medicinal extract
(200.0g), extracting n-butyl alcohol medicinal extract (189.0g), water section.
S3. ethyl acetate is taken to extract medicinal extract (200.0g) through 200~300 mesh normal-phase silica gel column chromatographies, with chloroform-methanol body
Product is than being 95:5-40:60 ratio gradient elution obtains E through the identical flow point of TLC thin-layer chromatography combining data detection principal points1-E11
Totally 11 components.
S4. by the component E5(10.0g) is through 200~300 mesh normal-phase silica gel column chromatographies, with chloroform-methanol volume ratio
95:5-80:20) ratio gradient elution, combining data detection same principle point flow point, obtains E5-1~E5-6Totally six subfractions.It will be sub-
Component E5-6It recrystallizes, is eluted with methanol repeatedly, obtain compound 1.
S5. by the E9MCI column chromatographies are pressed in, and chlorophyll is removed simultaneously with 30%~100% methanol-water gradient elution
Obtain E9-1~E9-10Totally 10 subfractions, by the subfraction E9-4Through Sephadex LH-20 column chromatographies, methanol is eluant, eluent,
Obtain compound 2；
S6. by the subfraction E9-8Through being recrystallizing repeatedly so as to obtain to obtain compound 2.
By compound 1, compound 2, the chemical constitution of compound 3 with nuclear magnetic resoance spectrum (1HNMR,13CNMR, DEPT,
HSQC, HMBC, 1H-1H COSY), the identification of the wave spectrograms such as ESI-MS.
The physicochemical data of compound 1：White amorphous powder, Mp 276-278 DEG C, molecular formula C26H32O11；ESI-MS
m/z:521[M+H]+,543.3[M+Na]+,559[M+K]+,519[M–H]–555[M+Cl]-；1H NMR(400MHz,DMSO):δ
7.87 (1H, s, 3-OH), 5.62 (1H, s, H-2'), 4.92 (1H, s, H-7), 4.87 (1H, d, J=4.8Hz, 11-OH), 4.48
(1H, d, J=7.2Hz, H-17a), 4.09 (1H, d, J=4.5Hz, H-12), 3.97 (1H, t, J=4.2Hz, H-11), 3.60
(4H,m,H-17b,21-OCH3), 3.29 (1H, m, 12-OH), 2.89 (1H, d, J=12.9Hz, H-5), 2.63 (2H, s, H-
1), 2.16 (1H, d, J=4.3Hz, H-9), 2.10 (3H, s, 4'-CH3),2.07(1H,m,H-6a),1.90(3H,s,5'-
CH3),1.76–1.66(4H,overlapped,H-6b,18-CH3),1.22(3H,s,19-CH3)；13C NMR(100MHz,
DMSO):δ192.8(C-2),170.0(C-20),167.3(C-16),164.1(C-1'),158.3(C-3'),144.2(C-3),
128.3(C-4),114.8(C-2'),82.5(C-7),81.2(C-12),74.6(C-12),72.2(C-17),71.4(C-11),
67.2(C-15),52.1(21-OCH3),48.7(C-1),44.7(C-10),41.1(C-5),40.5(C-8),28.6(C-6),
26.9(4'-CH3),19.9(5'-CH3),15.0(19-CH3),13.2(18-CH3)。
The physicochemical data of compound 2：Water white transparency needle, Mp 224-227 DEG C, molecular formula C25H32O11；ESI-MS m/
z:509[M+H]+,531[M+Na]+,547[M+K]+,507[M–H]–,543[M+Cl]-；1H NMR(400MHz,C5D5N):δ7.94
(1H,br s,3-OH),5.12(1H,overlapped,H-15),5.11(1H,overlapped,H-17b),5.05(1H,s,
), H-12 4.81 (1H, d, J=4.3Hz, H-11), 4.03 (1H, s, H-7), 3.96 (1H, d, J=6.4Hz, H-17a), 3.29
(1H, d, J=16.0Hz, H-5), 3.02 (1H, br s, H-1ax), 2.60 (1H, d, J=4.2Hz, H-9), 2.49 (1H, d, J
=15.6Hz, H-1eq), 2.34-2.25 (3H, m, H-2'a, H-2'b, H-6ax), 2.19 (1H, dt, J=13.7,6.8Hz, H-
3'),1.94(3H,s,18-CH3), 1.73 (1H, t, J=12.8Hz, H-6eq), 1.63 (3H, s, 19-CH3),0.84(3H,d,J
=6.5Hz, 4'-CH3), 0.81 (3H, d, J=6.5Hz, 5'-CH3)；13C NMR(100MHz,C5D5N):δ193.2(C-2),
174.1(C-20),172.0(C-1'),168.5(C-16),146.1(C-3),128.4(C-4),84.0(C-7),82.8(C-
13),76.5(C-12),73.8(C-11),73.0(C-17),68.7(C-15),50.2(C-14),49.7(C-1),46.3(C-
8),43.4(C-5),42.5(C-2'),42.4(C-9),41.5(C-10),29.7(C-6),25.7(C-3'),22.5(4'-
CH3),22.5(5'-CH3),15.8(19-CH3),13.5(18-CH3)。
The physicochemical data of compound 3：Water white transparency needle, Mp 294-296 DEG C, molecular formula C20H26O9；ESI-MS m/
z:411.2[M+H]+,433.3[M+Na]+,449[M+K]+,409[M–H]–445[M+Cl]-；1H NMR(400MHz,DMSO):δ
5.98 (1H, s, H-3), 5.35 (1H, d, J=5.1Hz, 12-OH), 5.34 (1H, d, J=6.1Hz, 15-OH), 5.25 (1H, d,
J=3.2Hz, 1-OH), 5.12 (1H, s, 1H, 14-OH), 4.96 (1H, d, J=6.1Hz, H-15), 4.92 (1H, br s, H-
7), 4.39 (1H, t, J=5.3Hz, H-11), 4.30 (1H, d, J=6.9Hz, H-17 α), 4.26 (1H, d, J=3.2Hz, H-
1), 3.68 (1H, d, J=5.7Hz, 11-OH), 3.60 (1H, d, J=6.9Hz, H-17 β), 3.54 (1H, d, J=5.1Hz, H-
12), 2.89 (1H, br d, J=12.6Hz, H-5), 2.32 (1H, d, J=4.7Hz, H-9), 2.18-2.10 (1H, dt, J=
14.8,2.8Hz, H-6 α), 1.74-1.64 (1H, ddd, J=14.8,2.8Hz, H-6 β), 1.89 (s, 3H, 18-CH3),1.24
(s,3H,19-CH3),1.04(s,3H,20-CH3)；13C NMR(100MHz,DMSO):δ198.4(C-2),173.8(C-16),
163.5(C-4),124.1(C-3),83.2(C-14),81.5(C-12),80.9(C-1),79.9(C-11),78.7(C-13),
73.8(C-7),69.1(C-17),68.6(C-15),48.8(C-8),47.7(C-10),43.8(C-5),42.4(C-9),27.2
(C-6),22.2(C-18),18.4(C-20),11.0(C-19)。
According to the spectral data of analysis of compounds 1~3 Brusatol, crow courage bitter principle are identified respectively as in conjunction with bibliography
J, crow courage bitter principle D.
Measure the anti-kentrogon attachment activity of the kusulactone class compound：
Inhibit barnacle using inhibiting the experimental model of line barnacle cyprids attachment to test the kusulactone class compound
The ability of larva attachment.
Line adult barnacle picks up from the mangrove trunk of Beilun Estuary mangrove swamps protected area, Guangxi.Cultural method is：It will obtain
Barnacle naupiar larva after fed with diatom Chaetoceros gracilis Schutt at 28 DEG C, be developed to after about 4d
The cyprids stage.Cyprids are filtered and are stored in the seawater of 0.22 μm of membrane filtration, 4 DEG C of refrigerator overnights is placed in and waits for
With.Sample to be tested is configured to 10 μM of mother liquor with DMSO, is then configured to the use of various concentration sample to be tested again.It will be in 24 orifice plates
1mL testing sample solutions are placed in each hole, and each testing sample solution includes 3 repetitions, then gently by 15 kentrogons
Ground is transferred in each hole containing solution to be measured and is tested.1 μ L DMSO are added in the filtering sea of 1mL, 15 are put per hole
A larva is as negative control.It is bright that 24 orifice plates handled well are placed on 15h in 28 DEG C of incubators：9h light cultures 48h.Wait for culture knot
24 orifice plates are placed in microscopically observation by Shu Hou, and record the larva number of travelling, attachment and death.The larva number of attachment and
Total larva number ratio is adhesive rate.The ratio of dead larvae number and total larva number is the death rate, and ratio uses percentage respectively
Than indicating.Each sample tests 3 repetitions under each concentration.It is analyzed by Probit softwares and calculates EC50And LC50, as a result see
Table 2.
Anti-pollution activity rating of the 2 kusulactone class compound of table to line barnacle (B.amphitrite) cyprids
The present embodiment detaches the extraction part of ethyl acetate, and carries out Test Identification and anti-marine fouling organism children
Worm attachment activity is tested.Show toxic effect ratio LC according to bibliography50/EC50Anti-fouling activity compound more than 15 or more is nothing
Malicious anti-fouling activity compound, 2 data of table can be seen that test compound has high inhibition effect to the attachment of line kentrogon,
The toxic effect ratio LC of middle Brusatol, crow courage bitter principle J and crow courage bitter principle D50/EC50Value is all higher than 15, shows that these ingredients are to pass through
Non-acute toxic effect inhibits the attachment of marine fouling organism larva, is safe and non-toxic to environment.It was found that main component crow courage
Picrol, crow courage bitter principle J and crow courage bitter principle D all have " significant inhibiting effect, EC to kentrogon attachment50Value is below 10 μM,
But its toxic effect is different, illustrates that different substituents have a very big impact work to the anti-fouling activity of kusulactone
With.It is found by the preliminary structure-activity relationship of kusulactone constituents (SAR) analysis, there are one α, beta unsaturated ketone base junctions for tool in A rings
The anti-pollution activity of kusulactone class, while 15 side chains can be remarkably reinforced in hydroxyl (3-OH) on the positions α of structure and/or carbonyl C
Kusulactone class can be influenced with the different substitutions in different degrees of lipophilic ester group structure and 21 ester carbonyl group C-structure
Close the anti-pollution activity of object.
A kind of 3 antifouling paint of embodiment
The addition of a kind of antifouling paint, including anti-pollution active constituent and film forming component, the anti-pollution active constituent is into
The 5% of the weight of film component；It is 1 that the anti-pollution active constituent, which is mass ratio,:1:1 Brusatol, crow courage bitter principle J and crow courage are bitter
Plain D；The film forming component is polyurethane resin.
Preparation method：The anti-pollution active constituent is mixed with polyurethane resin in proportion, and coalescents, dispersion is added
Then agent, antifoaming agent carry out dispersion and the antifouling paint are made.
A kind of 4 antifouling paint of embodiment
The addition of a kind of antifouling paint, including anti-pollution active constituent and film forming component, the anti-pollution active constituent is into
The 15% of the weight of film component；The anti-pollution active constituent is that the ethyl acetate prepared in embodiment 1 extracts medicinal extract.The film forming
Ingredient is acrylic resin.
Preparation method：The anti-pollution active constituent is mixed with acrylic resin in proportion, and coalescents, dispersion is added
Then agent, antifoaming agent carry out dispersion and the antifouling paint are made.
Above description is the detailed description for the present invention preferably possible embodiments, but embodiment is not limited to this hair
Bright patent claim.The same changes or modifications change completed under technical concept suggested by all present invention, should all belong to
In the covered the scope of the claims of the present invention.
Claims (10)
1. application of the kusulactone class compound in preventing marine biofouling, which is characterized in that the kusulactone class
The structural formula for closing object is formula I：
In formula I, R1,R2,R3,R4It is respectively selected from "-H " or "-OH " or "-CH3" or "-COOR' " or "-OOCR " ", wherein R' is
"-H " or "-CH3", R " is the aliphatic chain that carbon atom number is 3~7.
2. application of the kusulactone class compound according to claim 1 in preventing marine biofouling, feature exist
In, the kusulactone class compound be one or more of Brusatol, crow courage bitter principle J, crow courage bitter principle D, it is described
Brusatol, crow courage bitter principle J, crow courage bitter principle D structural formula see II-formula of formula IV：
3. application of the kusulactone class compound according to claim 1 or 2 in preventing marine biofouling, feature
It is, the kusulactone class compound is extracted from brucea plant.
4. application of the kusulactone class compound according to claim 3 in preventing marine biofouling, feature exist
In the kusulactone class compound is extracted from the root of Java brucea, stem, leaf or fruit.
5. application of the kusulactone class compound according to claim 4 in preventing marine biofouling, feature exist
In the extracting method of the kusulactone class compound includes the following steps：
S1. fruit of khosam and drying, crushing are chosen, fruit particle is obtained；Then the fruit particle ethyl alcohol impregnated, carried
It takes, obtains extracting solution；
S2. the extracting solution is filtered, medicinal extract is concentrated under reduced pressure to obtain；The medicinal extract is dispersed in water, uses petroleum ether, acetic acid successively
Ethyl ester and n-butanol are extracted, are concentrated in vacuo extract liquor, and petroleum ether extraction medicinal extract, ethyl acetate extraction medicinal extract are respectively obtained
With extracting n-butyl alcohol medicinal extract；
S3. the ethyl acetate is extracted into medicinal extract through normal-phase silica gel column chromatography, with chloroform-methanol gradient elution, through TLC thin layers
The identical flow point of combining data detection principal point is analysed, E is obtained1-E11Totally 11 components；
S4. by the component E5Through normal-phase silica gel column chromatography, with chloroform-methanol gradient elution, combining data detection same principle point flow point,
Obtain E5-1~E5-6Totally six subfractions；By the subfraction E5-6Recrystallization, is eluted with methanol, obtains Brusatol；
S5. by the E9MCI column chromatographies are pressed in, and chlorophyll is removed with 30%~100% methanol-water gradient elution and are obtained
E9-1~E9-10Totally 10 subfractions, by the subfraction E9-4Through Sephadex LH-20 column chromatographies, methanol is eluant, eluent, obtains crow
Courage bitter principle J；
S6. by the subfraction E9-8Through being recrystallized to give crow courage bitter principle D.
6. application of the kusulactone class compound according to claim 5 in preventing marine biofouling, feature exist
In in step S2 and S3, the normal phase silicagel column uses 200~300 mesh silica fillers.
7. application of the kusulactone class compound according to claim 5 in preventing marine biofouling, feature exist
In, in step S3, chloroform-methanol by volume 95:5-40:60 ratio elution；In step S4, chloroform-methanol is by volume
95:5-80:20 ratio elution.
8. application of the kusulactone class compound in preventing marine biofouling according to claims 1 or 2 or 4 or 5,
It is characterized in that, preparing antifouling paint using the kusulactone class compound.
9. application of the kusulactone class compound according to claim 8 in preventing marine biofouling, feature exist
In the antifouling paint includes anti-pollution active constituent and film forming component, and the addition of the anti-pollution active constituent is film forming component
Weight 0.5%~25%；The anti-pollution active constituent is the kusulactone class compound that structural formula is formula I；The film forming
Ingredient is hydrolysable resins, soluble resin or insoluble resin.
10. application of the kusulactone class compound according to claim 9 in preventing marine biofouling, feature exist
In the film forming component is the one or more of acrylic resin, epoxy resin, polyester resin, polyurethane resin.
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