CN102617532A - Bisabolane type sesquiterpene compound and its preparation method as well as its application as marine organism antifouling agent - Google Patents
Bisabolane type sesquiterpene compound and its preparation method as well as its application as marine organism antifouling agent Download PDFInfo
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- CN102617532A CN102617532A CN2011104400118A CN201110440011A CN102617532A CN 102617532 A CN102617532 A CN 102617532A CN 2011104400118 A CN2011104400118 A CN 2011104400118A CN 201110440011 A CN201110440011 A CN 201110440011A CN 102617532 A CN102617532 A CN 102617532A
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- sesquiterpene compound
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Abstract
The invention relates to a bisabolane type sesquiterpene compound and its preparation method as well as its application as a marine organism antifouling agent. The preparation method comprises: first conducting strain culturing on sponge endophytic fungus Aspergillus sp. (HM565949) in a strain culture medium, then carrying out fermentation culturing on the fungus in a fermentation medium, and then filtering the obtained fermentation broth to remove a thallus, concentrating the filtrate, and performing extraction with ethyl acetate; and concentrating the extracting solution and implementing chromatographic separation, and concentrating the eluents respectively so as to obtain white powder, i.e. aspergiterpenoid E. The bisabolane type sesquiterpene compound obtained from a marine fungus in the invention has the activity of inhibiting barnacle larvae from adhering, and can be used for development of marine antifouling agents. Besides, the raw materials can be produced in large scale and are not limited by resources. Therefore, the bisabolane type sesquiterpene compound provided in the invention boasts broad application prospects.
Description
Technical field
The present invention relates to 7,11 rare Bisabolane sesquiterpene compounds that are dehydrogenated to ring of a kind of occurring in nature, particularly relate to one type and have and suppress kentrogon and adhere to active Bisabolane sesquiterpene compound and preparation method thereof and application.
Background technology
The larva that marine biofouling is meant marine fouling organism such as barnacle, polyzoan, Ascidian etc. is in various maritime facilities surface attachment such as hull, fish box, oil well, growth so that form group, increases the weight of the burden of equipment; Simultaneously, these fouling organisms also can secrete acidic substance corrosion facility.The whole world is annual because the financial loss that marine biofouling causes is huge.The anti-fouling material that uses at present mainly is to add in enforcements surfaces coated such as hulls to contain sterilant or organometallic organic coating, and these chemical ingredientss when bringing into play anti-fouling effect also havoc ocean environment.The research and development of environment amenable marine natural stain control agent is badly in need of by this area.At present, do not see the marine natural stain control agent that from marine microorganism, obtains to have significant application value as yet.
Summary of the invention
The object of the present invention is to provide a kind of Bisabolane sesquiterpene compound that derives from the sponge endogenetic fungus and preparation method thereof and application, it can satisfy the demand of prior art.Culture presevation information: depositary institution's title: Institute of Microorganism, Academia Sinica; Depositary institution address: No. 3, Yard 1, BeiChen xi Road, Chaoyang District, Beijing City; Preservation date: on November 03rd, 2011; Deposit number: 5440; Classification name: aspergillus Aspergillus sp..
A kind of Bisabolane sesquiterpene compound is characterized in that its structural formula does
The preparation method of above-mentioned Bisabolane sesquiterpene compound; It is characterized in that in bacterium culture medium, sponge endogenetic fungus Aspergillus sp. (HM565949) being carried out spawn culture earlier; In fermention medium, this fungi is carried out fermentation culture again, with the gained filtering fermentation liquor, remove thalline then; To filtrate concentrates, and uses ethyl acetate extraction; Extraction liquid concentrates laggard circumstances in which people get things ready for a trip spectrum to be separated, and the gained elutriant is concentrated, and obtains white powder respectively, is aspergiterpenoid E.
The application of above-mentioned Bisabolane sesquiterpene compound in preparation sea life stain control agent.
The present invention has obtained a kind of Bisabolane sesquiterpene compound from thalassiomycetes; Barnacle Balanus amphitrite larva is had overt toxicity, can be used for developing stain control agent, and raw material can carry out scale operation; Do not receive resource limit, therefore have a extensive future.
Embodiment
The preparation of compound of the present invention
(1) the used substratum of spawn culture of sponge endogenetic fungus Aspergillus sp. (HM565949) contains glucose 1.0% (weight percent; Yeast extract paste 0.2%, peptone 0.2%, agar 1.0%, sodium-chlor 3.0% down together); All the other are water; Process the test tube slant during use, fungal bacterial strain was cultivated 5 days down at 30 ℃.
Described bacterium culture medium contains glucose 0.1%-5.0% (weight percent, down together), yeast extract paste 0.01%-1%, peptone 0.01%-1%, agar 0.1%-3.0%, sodium-chlor 0.05%-5%, and all the other are water.
(2) the used fermention medium of fermentation culture of sponge endogenetic fungus Aspergillus sp. (HM565949) contains glucose 1.0% (weight percent; Yeast extract paste 0.2%, peptone 0.2%, sodium-chlor 3.0% down together); All the other are water, and fungal bacterial strain was cultivated 30 days in 28 ℃.
Described fermention medium contains glucose 0.1%-5.0% (weight percent, down together), yeast extract paste 0.01%-1%, peptone 0.01%-1%, sodium-chlor 0.05%-5%, and all the other are water.
(3) extraction separation compound from the fermented liquid of fungi Aspergillus sp. (HM565949).With the gained filtering fermentation liquor, remove thalline; Fermented liquid is with ethyl acetate extraction 5 times, after the gained extraction liquid is concentrated, carries out chromatographic separation, and elutriant concentrates respectively and obtains white powder, is the E with aspergiterpenoid.The spectral data of gained compound
Aspergiterpenoid?E：white?powder；UV(MeOH)λ
max?198.1，236.4，280.5nm；?
1H?NMR(CDCl
3，600MHz)：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(CDCl
3，150MHz)：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(CH
2，C-15)，37.0(CH
2，C-10)，34.0(CH
2，C-8)，32.0(CH
3，C-13)，31.7(CH
3，C-14)，25.1(CH
3，C-12)，16.8(CH
2，C-9)；HRESIMS?m/z[M-H]
-249.1497.
The structural formula of compound that makes is:
The anti-barnacle of compound adheres to active testing
Compound of the present invention adheres to activity test to kentrogon B.amphitrite anti-to be tested according to following literature method: Thiyagarajan V.; Harder T.; Qiu J.W.; Qian P.Y.Mar Biol (Berl) 2003,143,543-554.
Compound of the present invention has the significantly anti-inhibition activity of adhering to kentrogon B.amphitrite, and wherein aspergiterpenoid E inhibiting rate that adheres to kentrogon B.amphitrite when concentration is 25 μ g/mL is 100%.Bisabolane sesquiterpene compound of the present invention adheres to have to kentrogon and suppresses active, can be made into marine antifoulant.
Claims (3)
1. a Bisabolane sesquiterpene compound is characterized in that structural formula does
2. the preparation method of the described Bisabolane sesquiterpene compound of claim 1; It is characterized in that in bacterium culture medium, sponge endogenetic fungus Aspergillus sp. (HM565949) being carried out spawn culture earlier; In fermention medium, this fungi is carried out fermentation culture again, with the gained filtering fermentation liquor, remove thalline then; The heating of will filtrating concentrates, and uses ethyl acetate extraction; Extraction liquid concentrates laggard circumstances in which people get things ready for a trip spectrum to be separated, and the gained elutriant is concentrated respectively, gets white powder, is aspergiterpenoid E.Described bacterium culture medium contains glucose 0.1%-5.0% (weight percentage; Yeast extract paste 0.01%-1%, peptone 0.01%-1%, agar 0.1%-3.0%, sodium-chlor 0.05%-5% down together); All the other are water, and culture temperature is 15-35 ℃, and incubation time is 3-10 days; Described fermention medium contains glucose 0.1%-5.0%, yeast extract paste 0.01%-1%, peptone 0.01%-1%, sodium-chlor 0.05%-5%, and all the other are water, and culture temperature is 15-35 ℃, and incubation time is 7-40 days.
3. the application of the described Bisabolane sesquiterpene compound of claim 1 in the preparation marine antifoulant.
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|---|---|---|---|
| CN201110440011.8A CN102617532B (en) | 2011-12-03 | 2011-12-03 | A kind of Bisabolane sesquiterpene compound and preparation method thereof and the application as marine organisms anti-fouling agent |
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| CN201110440011.8A CN102617532B (en) | 2011-12-03 | 2011-12-03 | A kind of Bisabolane sesquiterpene compound and preparation method thereof and the application as marine organisms anti-fouling agent |
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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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Patent 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 |
Non-Patent Citations (1)
| Title |
|---|
| MARK W. SUMARAH 等: "Antifungal metabolites from fungal endophytes of Pinus strobus", 《PHYTOCHEMISTRY》 * |
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