CN102617532B - A kind of Bisabolane sesquiterpene compound and preparation method thereof and the application as marine organisms anti-fouling agent - Google Patents
A kind of Bisabolane sesquiterpene compound and preparation method thereof and the application as marine organisms anti-fouling agent Download PDFInfo
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- CN102617532B CN102617532B CN201110440011.8A CN201110440011A CN102617532B CN 102617532 B CN102617532 B CN 102617532B CN 201110440011 A CN201110440011 A CN 201110440011A CN 102617532 B CN102617532 B CN 102617532B
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- VGVOGZNGRXPFMW-HNNXBMFYSA-N CC(C)(CCC1)O[C@]1(C)c(ccc(CO)c1)c1O Chemical compound CC(C)(CCC1)O[C@]1(C)c(ccc(CO)c1)c1O VGVOGZNGRXPFMW-HNNXBMFYSA-N 0.000 description 1
Abstract
A kind of Bisabolane sesquiterpene compound and preparation method thereof and the application as marine organisms anti-fouling agent, during preparation first in bacterium culture medium to sponge endogenetic fungus Aspergillus? sp. (HM565949) carries out spawn culture, in the fermentation medium this fungus is carried out fermentation culture again, then by gained filtering fermentation liquor, remove thalline, filtrate is concentrated, is extracted with ethyl acetate; Carry out chromatographic isolation after extract concentration, gained eluent is concentrated respectively, obtains white powder, does is it aspergiterpenoid? E. The Bisabolane sesquiterpene compound that the present invention obtains from marine fungi has suppression kentrogon attachment activity, can be used for developing marine antifoulant, and raw material can carry out large-scale production, not by resource limit, therefore has a extensive future.
Description
Technical field
The present invention relates to the looped Bisabolane sesquiterpene compound of 7,11 dehydrogenations rare in a kind of nature, particularly relate to class Bisabolane sesquiterpene compound with suppression kentrogon attachment activity and preparation method thereof and application.
Background technology
Marine biofouling refer to the larva of marine fouling organism such as barnacle, bryozoan, ascidian etc. in the various marine facility surface attachment such as hull, fish box, oil well, growth so that forming group, increase the weight of the burden of equipment; Meanwhile, these fouling organisms also can secrete acidic materials corrosion facility. The economic loss that the whole world causes due to marine biofouling every year is huge. Currently used anti-fouling material mainly implements surface at hull etc. and is coated with and adds containing insecticide or organometallic organic coating, and these chemical compositions also heavy damage marine environment while playing anti-fouling effect. The research and development of environment amenable marine natural anti-fouling agent is badly in need of by this area. At present, there is not yet the marine natural anti-fouling agent obtaining significant application value from Marine microorganism.
Summary of the invention
It is an object of the invention to provide a kind of Bisabolane sesquiterpene compound deriving from sponge endogenetic fungus and preparation method thereof and application, it can meet the demand of prior art. Culture presevation information: depositary institution's title: Institute of Microorganism, Academia Sinica; Depositary institution address: Yard 1, BeiChen xi Road, Chaoyang District, Beijing City 3; Preservation date: on November 03rd, 2011; Deposit number: 5440; Classification And Nomenclature: aspergillosis Aspergillussp..
A kind of Bisabolane sesquiterpene compound, it is characterised in that its structural formula is
The preparation method of above-mentioned Bisabolane sesquiterpene compound, it is characterized in that first in bacterium culture medium, sponge endogenetic fungus Aspergillussp. (HM565949) being carried out spawn culture, in the fermentation medium this fungus is carried out fermentation culture again, then by gained filtering fermentation liquor, remove thalline, filtrate is concentrated, is extracted with ethyl acetate; Carry out chromatographic isolation after extract concentration, gained eluent is concentrated, respectively obtains white powder, be aspergiterpenoidE.
The application in preparation marine organisms anti-fouling agent of the above-mentioned Bisabolane sesquiterpene compound.
The present invention obtains a kind of Bisabolane sesquiterpene compound from marine fungi, barnacle Balanusamphitrite larva is had overt toxicity, can be used for developing anti-fouling agent, and raw material can carry out large-scale production, not by resource limit, therefore have a extensive future.
Detailed description of the invention
The preparation of the compound of the present invention
(1) culture medium used by spawn culture of sponge endogenetic fungus Aspergillussp. (HM565949) contains glucose 1.0% (percentage by weight, lower with), yeast extract 0.2%, peptone 0.2%, agar 1.0%, sodium chloride 3.0%, all the other are water, making test tube slant during use, fungal bacterial strain is cultivated 5 days at 30 DEG C.
Described bacterium culture medium contains glucose 0.1%-5.0% (percentage by weight, lower same), yeast extract 0.01%-1%, peptone 0.01%-1%, agar 0.1%-3.0%, sodium chloride 0.05%-5%, and all the other are water.
(2) fermentation medium used by fermentation culture of sponge endogenetic fungus Aspergillussp. (HM565949) contains glucose 1.0% (percentage by weight, lower with), yeast extract 0.2%, peptone 0.2%, sodium chloride 3.0%, all the other are water, and fungal bacterial strain is cultivated 30 days in 28 DEG C.
Described fermentation medium contains glucose 0.1%-5.0% (percentage by weight, lower same), yeast extract 0.01%-1%, peptone 0.01%-1%, sodium chloride 0.05%-5%, and all the other are water.
(3) from the fermentation liquid of fungus Aspergillussp. (HM565949), separating purification compound is extracted. By gained filtering fermentation liquor, remove thalline; Fermentation liquid is extracted with ethyl acetate 5 times, after being concentrated by gained extract, carries out chromatography, and eluent concentrates respectively and obtains white powder, is and aspergiterpenoidE.
The spectral data of gained compound
AspergiterpenoidE:whitepowder; UV (MeOH) ��max198.1,236.4,280.5nm;1HNMR(CDCl3, 600MHz): 9.20 (1H, s ,-OH), 7.02 (1H, d, 9.6, H-5), 6.83 (1H, brs, H-2), 6.81 (1H, brd, 9.6, H-4), 4.63 (2H, s, H-15), 2.43 (1H, m, H-8a), 1.76 (1H, m, H-8b), 1.68 (1H, brs ,-OH), 1.67 (1H, m, H-9a), 1.60 (1H, m, H-9b), 1.52 (2H, m, H-10), 1.49 (3H, s, H-14), 1.28 (3H, s, H-13), 0.96 (3H, s, H-12);13CNMR(CDCl3, 150MHz): 157.2 (C, C-1), (141.7 C, C-3), 130.4 (C, C-6), 124.7 (CH, C-5), (117.8 CH, C-4), 115.9 (CH, C-2), 77.7 (C, C-7), (74.9 C, C-11), 65.1 (CH2, C-15), 37.0 (CH2, C-10), 34.0 (CH2, C-8), 32.0 (CH3, C-13), 31.7 (CH3, C-14), 25.1 (CH3, C-12), 16.8 (CH2, C-9); HRESIMSm/z [M-H]-249.1497.
The structural formula of compound prepared is:
The anti-barnacle attachment activity test of compound
The anti-attachment activity test of kentrogon B.amphitrite is tested by the compound of the present invention according to following literature method: ThiyagarajanV.; HarderT.; QiuJ.W.; QianP.Y.MarBiol (Berl) 2003,143,543-554.
Kentrogon B.amphitrite is had obvious anti-attachment inhibitory activity by the compound of the present invention, and wherein aspergiterpenoidE attachment suppression ratio to kentrogon B.amphitrite when concentration is 25 �� g/mL is 100%. Kentrogon attachment is had inhibitory activity by the Bisabolane sesquiterpene compound of the present invention, can be made into marine antifoulant.
Claims (2)
1. the preparation method of a Bisabolane sesquiterpene compound a spergiterpenoidE, it is characterized in that first in bacterium culture medium, sponge endogenetic fungus Aspergillussp.HM565949 being carried out spawn culture, in the fermentation medium this fungus is carried out fermentation culture again, then by gained filtering fermentation liquor, remove thalline, by filtrate heating concentration, it is extracted with ethyl acetate; Carry out chromatographic isolation after extract concentration, gained eluent is concentrated, obtains white powder, be aspergiterpenoidE; Described bacterium culture medium contains glucose 0.1%-5.0%, yeast extract 0.01%-1%, peptone 0.01%-1%, agar 0.1%-3.0%, sodium chloride 0.05%-5%, and all the other are water, and cultivation temperature is 15-35 DEG C, and incubation time is 3-10 days; Described fermentation medium contains glucose 0.1%-5.0%, yeast extract 0.01%-1%, peptone 0.01%-1%, sodium chloride 0.05%-5%, and all the other are water, and cultivation temperature is 15-35 DEG C, and incubation time is 7-40 days; Above-mentioned percent is percetage by weight; AspergiterpenoidE is structured with:
2. the Bisabolane sesquiterpene compound a spergiterpenoidE of claim 1 preparation application in preparing marine antifoulant.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101747190A (en) * | 2008-11-28 | 2010-06-23 | 复旦大学 | Bisabolane sesquiterpene compound and preparation method and application thereof |
| CN101921250A (en) * | 2009-12-24 | 2010-12-22 | 中国海洋大学 | Bisabolane sesquiterpene derivative and preparation method and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101747190A (en) * | 2008-11-28 | 2010-06-23 | 复旦大学 | Bisabolane sesquiterpene compound and preparation method and application thereof |
| CN101921250A (en) * | 2009-12-24 | 2010-12-22 | 中国海洋大学 | Bisabolane sesquiterpene derivative and preparation method and application thereof |
Non-Patent Citations (1)
| Title |
|---|
| Mark W. Sumarah 等.Antifungal metabolites from fungal endophytes of Pinus strobus.《Phytochemistry》.2011,第72卷(第14-15期), * |
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